Organic electroluminescent device configured to emit light with high luminous efficiency
11489121 · 2022-11-01
Assignee
Inventors
- Satomi Tasaki (Sodegaura, JP)
- Kazuki Nishimura (Sodegaura, JP)
- Masatoshi Saito (Sodegaura, JP)
- Tetsuya Masuda (Sodegaura, JP)
- Yuki Nakano (Sodegaura, JP)
- Masato Nakamura (Sodegaura, JP)
Cpc classification
H10K2101/30
ELECTRICITY
H10K85/631
ELECTRICITY
H10K85/6574
ELECTRICITY
H10K85/626
ELECTRICITY
H10K85/6572
ELECTRICITY
H10K85/633
ELECTRICITY
H10K85/615
ELECTRICITY
H10K85/6576
ELECTRICITY
International classification
Abstract
An organic electroluminescence device includes an anode, a cathode, a first emitting layer and a second emitting layer that are interposed between the anode and the cathode and are in a direct contact with each other, and a first electron transporting layer between the cathode and the first emitting layer and the second emitting layer being in a direct contact with each other. The first emitting layer contains a first compound represented by a formula (1) as a first host material, the first compound having at least one group represented by a formula (11). The second emitting layer contains a second compound represented by a formula (2) as a second host material. The first electron transporting layer contains a third compound represented by a formula (3). ##STR00001##
Claims
1. An organic electroluminescence device comprising: an anode; a cathode; a first emitting layer and a second emitting layer interposed between the anode and the cathode; and a first electron transporting layer between the first and second emitting layers and the cathode, wherein the first emitting layer comprises a first compound as a first host material, the second emitting layer comprises a second compound as a second host material, the first host material and the second host material are different from each other, the first emitting layer at least comprises a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less, the second emitting layer at least comprises a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less, the compound that is contained in the first emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less and the compound that is contained in the second emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less are mutually the same or different, a triplet energy T.sub.1(H1) of the first host material and a triplet energy T.sub.1(H2) of the second host material satisfy a numerical formula below (Numerical Formula 1A), and the first electron transporting layer comprises a third compound represented by a formula (3) below,
T.sub.1(H1)>T.sub.1(H2) (Numerical Formula 1A) ##STR00688## where: A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; L is a single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or a (n+1)-valent group having a structure in which two or three different groups selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms are bonded to each other; C is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms; n is 1, 2 or 3; when n is 2 or more, L is not a single bond; and when n is 2 or more, a plurality of C are mutually the same or different.
2. The organic electroluminescence device according to claim 1, wherein the first emitting layer and the second emitting layer are in a direct contact with each other.
3. The organic electroluminescence device according to claim 1, wherein the first host material comprises, in a molecule, a linking structure comprising a benzene ring and a naphthalene ring linked to each other with a single bond, the benzene ring and the naphthalene ring in the linking structure are each independently fused or not fused with a further monocyclic ring or fused ring, and the benzene ring and the naphthalene ring in the linking structure are further linked to each other by cross-linking at at least one site other than the single bond.
4. The organic electroluminescence device according to claim 3, wherein the cross-linking comprises a double bond.
5. The organic electroluminescence device according to claim 1, wherein the first host material comprises, in a molecule, a biphenyl structure in which a first benzene ring and a second benzene ring are linked to each other with a single bond, and the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking at at least one site other than the single bond.
6. The organic electroluminescence device according to claim 5, wherein the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking at one site other than the single bond.
7. The organic electroluminescence device according to claim 5, wherein the cross-linking comprises a double bond.
8. The organic electroluminescence device according to claim 5, wherein the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking at two sites other than the single bond, and the cross-linking does not comprise a double bond.
9. The organic electroluminescence device according to claim 1, wherein the first compound is a compound represented by a formula (1) below, ##STR00689## where: in the formula (1): R.sub.101 to R.sub.110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or the group represented by a formula (11) above; at least one of R.sub.101 to R.sub.110 is the group represented by the formula (11); when a plurality of groups represented by the formula (11) are present, the plurality of groups represented by the formula (11) are mutually the same or different; L.sub.101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; Ar.sub.101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; mx is 0, 1, 2, 3, 4 or 5; when two or more L.sub.101 are present, two or more L.sub.101 are mutually the same or different; when two or more Ar.sub.101 are present, two or more Ar.sub.101 are mutually the same or different; * in the formula (11) represents a bonding position to a pyrene ring in the formula (1); in the first compound represented by the formula (1), R.sub.901, R.sub.902, R.sub.903, R.sub.904, R.sub.905, R.sub.801 and R.sub.802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different; when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different; when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different; and when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different.
10. The organic electroluminescence device according to claim 1, wherein the second compound is a compound represented by a formula (2) below, ##STR00690## where: R.sub.201 to R.sub.208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; L.sub.201 and L.sub.202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; Ar.sub.2O.sub.1 and Ar.sub.2O.sub.2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; in the second compound represented by the formula (2), R.sub.901, R.sub.902, R.sub.903, R.sub.904, R.sub.905, R.sub.906, R.sub.907, R.sub.801 and R.sub.802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different; when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different; when a plurality of R.sub.906 are present, the plurality of R.sub.906 are mutually the same or different; when a plurality of R.sub.907 are present, the plurality of R.sub.907 are mutually the same or different; when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different; and when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different.
11. The organic electroluminescence device according to claim 1, wherein the third compound is a compound represented by a formula (31) or a formula (310), ##STR00691## where: in the formula (31): A, B and C represent the same as A, B and C defined in the formula (3); at least one combination of adjacent two or more of R.sub.31 to R.sub.34 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and R.sub.31 to R.sub.34 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; ##STR00692## where: in the formula (310): A and B represent the same as A and B defined in the formula (3); X.sub.30 is CR.sub.51R.sub.52, NR.sub.53, an oxygen atom, or a sulfur atom; when X.sub.30 is CR.sub.51R.sub.52, a combination of R.sub.51 and R.sub.52 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; at least one combination of adjacent two or more of R.sub.300 to R.sub.304 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; R.sub.53, and R.sub.51, R.sub.52, and R.sub.300 to R.sub.304 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; na is 3; and three R.sub.300 are mutually the same or different; in the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
12. The organic electroluminescence device according to claim 11, wherein the third compound is a compound represented by a formula (32) below, ##STR00693## where: in the formula (32): A and B represent the same as A and B defined in the formula (3); X.sub.30 is CR.sub.51R.sub.52, NR.sub.53, an oxygen atom, or a sulfur atom; when X.sub.30 is CR.sub.51R.sub.52, a combination of R.sub.51 and R.sub.52 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; at least one combination of adjacent two or more of R.sub.301 to R.sub.304 and R.sub.306 to R.sub.308 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and R.sub.53, and R.sub.51, R.sub.52, R.sub.301 to R.sub.304 and R.sub.306 to R.sub.308 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
13. The organic electroluminescence device according to claim 1, wherein the third compound is a compound represented by a formula (36) below, ##STR00694## where: in the formula (36): A, B and C represent the same as A, B and C defined in the formula (3); at least one combination of adjacent two or more of R.sub.32 to R.sub.39 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; R.sub.32 to R.sub.39 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; in the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
14. The organic electroluminescence device according to claim 1, wherein C is a substituted or unsubstituted heterocyclic group having 13 to 35 ring atoms.
15. The organic electroluminescence device according to claim 1, wherein C is a substituted or unsubstituted aryl group having 14 to 24 ring carbon atoms.
16. The organic electroluminescence device according to claim 1, wherein the third compound is a compound represented by a formula (37) below, ##STR00695## where: in the formula (37): A, B and L represent the same as A, B and L defined in the formula (3); Cz is a group represented by a formula (Cz1), (Cz2), or (Cz3); n is 1, 2 or 3; and when n is 2 or 3, a plurality of Cz are mutually the same or different, ##STR00696## where: in the formulae (Cz1), (Cz2), and (Cz3): at least one combination of adjacent two or more of R.sub.311 to R.sub.318 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; at least one combination of adjacent two or more of R.sub.320 to R.sub.324 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; at least one combination of adjacent two or more of R.sub.330 to R.sub.334 and Rx are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; at least one combination of adjacent two or more of R.sub.340 to R.sub.344 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; at least one combination of adjacent two or more of R.sub.351 to R.sub.358 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; R.sub.311 to R.sub.318, R.sub.320 to R.sub.324, R.sub.330 to R.sub.334, R.sub.X, R.sub.340 to R.sub.344 and R.sub.351 to R.sub.358 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; n1, n2 and n3 are 3; three R.sub.320 are mutually the same or different; three R.sub.330 are mutually the same or different; three R.sub.340 are mutually the same or different; and * in the formulae (Cz1), (Cz2), and (Cz3) is bonded to L, in the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
17. The organic electroluminescence device according to claim 1, wherein the compound represented by the formula (3) is a compound represented by a formula (38) below, ##STR00697## where: in the formula (38): A and B represent the same as A and B defined in the formula (3); La is a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms; and Ac is a group represented by one of formulae (Ac1), (Ac2), and (Ac3) below, ##STR00698## where: in the formula (Ac1): X.sub.31 to X.sub.36 are each independently a nitrogen atom, a carbon atom bonded to La, or a carbon atom bonded to Ry; at least one of X.sub.31 to X.sub.36 is a nitrogen atom; one of X.sub.31 to X.sub.36 is a carbon atom bonded to La; Ry is a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and when a plurality of Ry are present, the plurality of Ry are mutually the same or different; in the formula (Ac2): X.sub.21 to X.sub.28 are each independently a nitrogen atom, a carbon atom bonded to La, or a carbon atom bonded to Rz; at least one of X.sub.21 to X.sub.28 is a nitrogen atom; one of X.sub.21 to X.sub.28 is a carbon atom bonded to La; when a plurality of Rz are present, at least one combination of adjacent two or more of the plurality of Rz are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; Rz neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring is each independently a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, in the formula (Ac3): n4 is 1, 2, 3, 4, 5, 6, 7, 8 or 9; D is an aryl group having a cyano group whose number is n4 and having 6 to 18 ring carbon atoms, or a heterocyclic group having a cyano group whose number is n4 and having 5 to 13 ring atoms; D has a substituent other than a cyano group or does not have a substituent other than a cyano group; and * in the formula (Ac3) is bonded to La; in the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
18. The organic electroluminescence device according to claim 1, further comprising: a second electron transporting layer between the first electron transporting layer and the cathode.
19. The organic electroluminescence device according to claim 1, wherein the first emitting layer is interposed between the anode and the second emitting layer.
20. The organic electroluminescence device according to claim 1, further comprising: a hole transporting layer between the anode and the first and second emitting layers, wherein the hole transporting layer comprises a compound represented by a formula (C1) or a formula (D1), ##STR00699## where: in the formula (C1): L.sub.A, L.sub.B, and L.sub.C are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms; A.sub.A, B.sub.B, and C.sub.C are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a group represented by —Si(R′.sub.901)(R′.sub.902)(R′.sub.903); R′.sub.901 to R′.sub.903 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms; when a plurality of R′.sub.901 are present, the plurality of R′.sub.901 are mutually the same or different; when a plurality of R′.sub.902 are present, the plurality of R′.sub.902 are mutually the same or different; and when a plurality of R′.sub.903 are present, the plurality of R′.sub.903 are mutually the same or different, ##STR00700## where: in the formula (D1): A.sub.41 and A.sub.42 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; L.sub.41 and L.sub.42 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; at least one combination of adjacent two or more of Ra.sub.410 to Ra.sub.414 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; at least one combination of adjacent two or more of Ra.sub.420 to Ra.sub.424 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; Ra.sub.410 to Ra.sub.414 and Ra.sub.420 to Ra.sub.424 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a halogen atom, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; m1 and m2 are 3; three Ra.sub.410 are mutually the same or different; and three Ra.sub.420 are mutually the same or different, in the compound represented by the formula (D1), R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
21. The organic electroluminescence device according to claim 1, wherein a substituent for a substituted or unsubstituted group is at least one group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.
22. The organic electroluminescence device according to claim 1, wherein a substituent for a substituted or unsubstituted group is an alkyl group having 1 to 5 carbon atoms.
23. The organic electroluminescence device according to claim 1, wherein in the first compound, the second compound and the third compound, all groups described as substituted or unsubstituted groups are unsubstituted groups.
24. The organic electroluminescence device of claim 1, wherein neither the first emitting layer, nor the second emitting layer contains a phosphorescent material.
25. The organic electroluminescent device of claim 1, wherein the compound that is contained in the first emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less and the compound that is contained in the second emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less are mutually the same.
26. An organic electroluminescence device comprising: an anode; a cathode; a first emitting layer and a second emitting layer interposed between the anode and the cathode, and a first electron transporting layer between the first and second emitting layers and the cathode, wherein the first emitting layer comprises a first compound represented by a formula (1) below as a first host material, the first compound comprises at least one group represented by a formula (11) below, the second emitting layer comprises a second compound represented by a formula (2) below as a second host material, the first electron transporting layer comprises a third compound represented by a formula (3) below, and a triplet energy T.sub.1(H1) of the first host material and a triplet energy T.sub.1(H2) of the second host material satisfy a numerical formula below (Numerical Formula 1A),
T.sub.1(H1)>T.sub.1(H2) (Numerical Formula 1A) ##STR00701## where: in the formula (1): R.sub.101 to R.sub.110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or the group represented by a formula (11) above; at least one of R.sub.101 to R.sub.110 is the group represented by the formula (11); when a plurality of groups represented by the formula (11) are present, the plurality of groups represented by the formula (11) are mutually the same or different; L.sub.101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; Ar.sub.101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; mx is 0, 1, 2, 3, 4 or 5; when two or more L.sub.101 are present, two or more L.sub.101 are mutually the same or different; when two or more Ar.sub.101 are present, two or more Ar.sub.101 are mutually the same or different; and * in the formula (11) represents a bonding position to a pyrene ring in the formula (1), ##STR00702## where: in the formula (2): R.sub.201 to R.sub.208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; L.sub.201 and L.sub.202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and Ar.sub.2O.sub.1 and Ar.sub.2O.sub.2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, ##STR00703## where: in the formula (3): A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms; L is a single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or a (n+1)-valent group having a structure in which two or three different groups selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms are bonded to each other; C is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms; n is 1, 2 or 3; when n is 2 or more, L is not a single bond; and when n is 2 or more, a plurality of C are mutually the same or different; in the first compound represented by the formula (1) and the second compound represented by the formula (2): R.sub.901, R.sub.902, R.sub.903, R.sub.904, R.sub.905, R.sub.906, R.sub.907, R.sub.801 and R.sub.802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different; when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different; when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different; when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different; when a plurality of R.sub.906 are present, the plurality of R.sub.906 are mutually the same or different; when a plurality of R.sub.907 are present, the plurality of R.sub.907 are mutually the same or different; when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different; and when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different.
27. The organic electroluminescence device according to claim 26, wherein the first emitting layer and the second emitting layer are in a direct contact with each other.
28. An organic electroluminescence device comprising: an anode; a cathode; a first emitting layer and a second emitting layer interposed between the anode and the cathode; and a first electron transporting layer between the first and second emitting layers and the cathode, wherein the first emitting layer comprises a first compound as a first host material, the second emitting layer comprises a second compound as a second host material, the first host material and the second host material are different from each other, the first emitting layer at least comprises a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less, the second emitting layer at least comprises a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less, the compound that is contained in the first emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less and the compound that is contained in the second emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less are mutually the same or different, a triplet energy T.sub.1(H1) of the first host material and a triplet energy T.sub.1(H2) of the second host material satisfy a numerical formula below (Numerical Formula 1A), and the first electron transporting layer comprises an azine derivative,
T.sub.1(H1)>T.sub.1(H2) (Numerical Formula 1A).
29. The organic electroluminescence device of claim 28, wherein neither the first emitting layer, nor the second emitting layer contains a phosphorescent material.
30. The organic electroluminescent device of claim 28, wherein the compound that is contained in the first emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less and the compound that is contained in the second emitting layer and emits fluorescence having the maximum peak wavelength of 500 nm or less are mutually the same.
Description
BRIEF EXPLANATION OF DRAWING(S)
(1)
(2)
(3)
(4)
DESCRIPTION OF EMBODIMENT(S)
Definitions
(5) Herein, a hydrogen atom includes isotope having different numbers of neutrons, specifically, protium, deuterium and tritium.
(6) In chemical formulae herein, it is assumed that a hydrogen atom (i.e. protium, deuterium and tritium) is bonded to each of bondable positions that are not annexed with signs “R” or the like or “D” representing a deuterium.
(7) Herein, the ring carbon atoms refer to the number of carbon atoms among atoms forming a ring of a compound (e.g., a monocyclic compound, fused-ring compound, crosslinking compound, carbon ring compound, and heterocyclic compound) in which the atoms are bonded with each other to form the ring. When the ring is substituted by a substituent(s), carbon atom(s) contained in the substituent(s) is not counted in the ring carbon atoms. Unless otherwise specified, the same applies to the “ring carbon atoms” described later. For instance, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. Further, for instance, 9,9-diphenylfluorenyl group has 13 ring carbon atoms and 9,9′-spirobifluorenyl group has 25 ring carbon atoms.
(8) When a benzene ring is substituted by a substituent in a form of, for instance, an alkyl group, the number of carbon atoms of the alkyl group is not counted in the number of the ring carbon atoms of the benzene ring. Accordingly, the benzene ring substituted by an alkyl group has 6 ring carbon atoms. When a naphthalene ring is substituted by a substituent in a form of, for instance, an alkyl group, the number of carbon atoms of the alkyl group is not counted in the number of the ring carbon atoms of the naphthalene ring. Accordingly, the naphthalene ring substituted by an alkyl group has 10 ring carbon atoms.
(9) Herein, the ring atoms refer to the number of atoms forming a ring of a compound (e.g., a monocyclic compound, fused-ring compound, crosslinking compound, carbon ring compound, and heterocyclic compound) in which the atoms are bonded to each other to form the ring (e.g., monocyclic ring, fused ring, and ring assembly). Atom(s) not forming the ring (e.g., hydrogen atom(s) for saturating the valence of the atom which forms the ring) and atom(s) in a substituent by which the ring is substituted are not counted as the ring atoms. Unless otherwise specified, the same applies to the “ring atoms” described later. For instance, a pyridine ring has 6 ring atoms, a quinazoline ring has 10 ring atoms, and a furan ring has 5 ring atoms. For instance, the number of hydrogen atom(s) bonded to a pyridine ring or the number of atoms forming a substituent are not counted as the pyridine ring atoms. Accordingly, a pyridine ring bonded with a hydrogen atom(s) or a substituent(s) has 6 ring atoms. For instance, the hydrogen atom(s) bonded to a quinazoline ring or the atoms forming a substituent are not counted as the quinazoline ring atoms. Accordingly, a quinazoline ring bonded with hydrogen atom(s) or a substituent(s) has 10 ring atoms.
(10) Herein, “XX to YY carbon atoms” in the description of “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represent carbon atoms of an unsubstituted ZZ group and do not include carbon atoms of a substituent(s) of the substituted ZZ group. Herein, “YY” is larger than “XX,” “XX” representing an integer of 1 or more and “YY” representing an integer of 2 or more.
(11) Herein, “XX to YY atoms” in the description of “substituted or unsubstituted ZZ group having XX to YY atoms” represent atoms of an unsubstituted ZZ group and does not include atoms of a substituent(s) of the substituted ZZ group. Herein, “YY” is larger than “XX,” “XX” representing an integer of 1 or more and “YY” representing an integer of 2 or more.
(12) Herein, an unsubstituted ZZ group refers to an “unsubstituted ZZ group” in a “substituted or unsubstituted ZZ group,” and a substituted ZZ group refers to a “substituted ZZ group” in a “substituted or unsubstituted ZZ group.”
(13) Herein, the term “unsubstituted” used in a “substituted or unsubstituted ZZ group” means that a hydrogen atom(s) in the ZZ group is not substituted with a substituent(s). The hydrogen atom(s) in the “unsubstituted ZZ group” is protium, deuterium, or tritium.
(14) Herein, the term “substituted” used in a “substituted or unsubstituted ZZ group” means that at least one hydrogen atom in the ZZ group is substituted with a substituent. Similarly, the term “substituted” used in a “BB group substituted by AA group” means that at least one hydrogen atom in the BB group is substituted with the AA group.
(15) Substituents Mentioned Herein
(16) Substituents mentioned herein will be described below.
(17) An “unsubstituted aryl group” mentioned herein has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
(18) An “unsubstituted heterocyclic group” mentioned herein has, unless otherwise specified herein, 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring atoms.
(19) An “unsubstituted alkyl group” mentioned herein has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
(20) An “unsubstituted alkenyl group” mentioned herein has, unless otherwise specified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6 carbon atoms.
(21) An “unsubstituted alkynyl group” mentioned herein has, unless otherwise specified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6 carbon atoms.
(22) An “unsubstituted cycloalkyl group” mentioned herein has, unless otherwise specified herein, 3 to 50, preferably 3 to 20, more preferably 3 to 6 ring carbon atoms.
(23) An “unsubstituted arylene group” mentioned herein has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
(24) An “unsubstituted divalent heterocyclic group” mentioned herein has, unless otherwise specified herein, 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring atoms.
(25) An “unsubstituted alkylene group” mentioned herein has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
(26) Substituted or Unsubstituted Aryl Group
(27) Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” mentioned herein include unsubstituted aryl groups (specific example group G1A) below and substituted aryl groups (specific example group G1B). (Herein, an unsubstituted aryl group refers to an “unsubstituted aryl group” in a “substituted or unsubstituted aryl group,” and a substituted aryl group refers to a “substituted aryl group” in a “substituted or unsubstituted aryl group.” A simply termed “aryl group” herein includes both of an “unsubstituted aryl group” and a “substituted aryl group.”
(28) The “substituted aryl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted aryl group” with a substituent. Examples of the “substituted aryl group” include a group derived by substituting at least one hydrogen atom in the “unsubstituted aryl group” in the specific example group G1A below with a substituent, and examples of the substituted aryl group in the specific example group G1B below. It should be noted that the examples of the “unsubstituted aryl group” and the “substituted aryl group” mentioned herein are merely exemplary, and the “substituted aryl group” mentioned herein includes a group derived by further substituting a hydrogen atom bonded to a carbon atom of a skeleton of a “substituted aryl group” in the specific example group G1B below, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted aryl group” in the specific example group G1B below.
(29) Unsubstituted Aryl Group (Specific Example Group G1A):
(30) a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from cyclic structures represented by formulae (TEMP-1) to (TEMP-15) below.
(31) ##STR00005## ##STR00006##
(32) ##STR00007##
Substituted Aryl Group (Specific Example Group G1B):
o-tolyl group, m-tolyl group, p-tolyl group, para-xylyl group, meta-xylyl group, ortho-xylyl group, para-isopropylphenyl group, meta-isopropylphenyl group, ortho-isopropylphenyl group, para-t-butylphenyl group, meta-t-butylphenyl group, ortho-t-butylphenyl group, 3,4,5-trimethylphenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, 9,9-bis(4-methylphenyl)fluorenyl group, 9,9-bis(4-isopropylphenyl)fluorenyl group, 9,9-bis(4-t-butylphenyl)fluorenyl group, cyanophenyl group, triphenylsilylphenyl group, trimethylsilylphenyl group, phenylnaphthyl group, naphthylphenyl group, and a group derived by substituting at least one hydrogen atom of a monovalent group derived from the cyclic structures represented by the formulae (TEMP-1) to (TEMP-15) with a substituent.
Substituted or Unsubstituted Heterocyclic Group
(33) The “heterocyclic group” mentioned herein refers to a cyclic group having at least one hetero atom in the ring atoms. Specific examples of the hetero atom include a nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
(34) The “heterocyclic group” mentioned herein is a monocyclic group or a fused-ring group.
(35) The “heterocyclic group” mentioned herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
(36) Specific examples (specific example group G2) of the “substituted or unsubstituted heterocyclic group” mentioned herein include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B). (Herein, an unsubstituted heterocyclic group refers to an “unsubstituted heterocyclic group” in a “substituted or unsubstituted heterocyclic group,” and a substituted heterocyclic group refers to a “substituted heterocyclic group” in a “substituted or unsubstituted heterocyclic group.”) A simply termed “heterocyclic group” herein includes both of “unsubstituted heterocyclic group” and “substituted heterocyclic group.”
(37) The “substituted heterocyclic group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted heterocyclic group” with a substituent. Specific examples of the “substituted heterocyclic group” include a group derived by substituting at least one hydrogen atom in the “unsubstituted heterocyclic group” in the specific example group G2A below with a substituent, and examples of the substituted heterocyclic group in the specific example group G2B below. It should be noted that the examples of the “unsubstituted heterocyclic group” and the “substituted heterocyclic group” mentioned herein are merely exemplary, and the “substituted heterocyclic group” mentioned herein includes a group derived by further substituting a hydrogen atom bonded to a ring atom of a skeleton of a “substituted heterocyclic group” in the specific example group G2B below, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted heterocyclic group” in the specific example group G2B below.
(38) The specific example group G2A includes, for instance, unsubstituted heterocyclic groups including a nitrogen atom (specific example group G2A1) below, unsubstituted heterocyclic groups including an oxygen atom (specific example group G2A2) below, unsubstituted heterocyclic groups including a sulfur atom (specific example group G2A3) below, and monovalent heterocyclic groups (specific example group G2A4) derived by removing a hydrogen atom from cyclic structures represented by formulae (TEMP-16) to (TEMP-33) below.
(39) The specific example group G2B includes, for instance, substituted heterocyclic groups including a nitrogen atom (specific example group G2B1) below, substituted heterocyclic groups including an oxygen atom (specific example group G2B2) below, substituted heterocyclic groups including a sulfur atom (specific example group G2B3) below, and groups derived by substituting at least one hydrogen atom of the monovalent heterocyclic groups (specific example group G2B4) derived from the cyclic structures represented by formulae (TEMP-16) to (TEMP-33) below.
(40) Unsubstituted Heterocyclic Groups Including Nitrogen Atom (Specific Example Group G2A1):
(41) pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, a pyridyl group, pyridazynyl group, a pyrimidinyl group, pyrazinyl group, a triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolizinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, indazolyl group, phenanthrolinyl group, phenanthridinyl group, acridinyl group, phenazinyl group, carbazolyl group, benzocarbazolyl group, morpholino group, phenoxazinyl group, phenothiazinyl group, azacarbazolyl group, and diazacarbazolyl group.
Unsubstituted Heterocyclic Groups Including Oxygen Atom (Specific Example Group G2A2):
furyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, a dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzisoxazolyl group, phenoxazinyl group, morpholino group, dinaphthofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.
Unsubstituted Heterocyclic Groups Including Sulfur Atom (Specific Example Group G2A3):
thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzothiophenyl group (benzothienyl group), isobenzothiophenyl group (isobenzothienyl group), dibenzothiophenyl group (dibenzothienyl group), naphthobenzothiophenyl group (nahthobenzothienyl group), benzothiazolyl group, benzisothiazolyl group, phenothiazinyl group, dinaphthothiophenyl group (dinaphthothienyl group), azadibenzothiophenyl group (azadibenzothienyl group), diazadibenzothiophenyl group (diazadibenzothienyl group), azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
Monovalent Heterocyclic Groups Derived by Removing One Hydrogen Atom from Cyclic Structures Represented by Formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):
(42) ##STR00008## ##STR00009##
(43) ##STR00010## ##STR00011##
(44) In the formulae (TEMP-16) to (TEMP-33), X.sub.A and Y.sub.A are each independently an oxygen atom, a sulfur atom, NH, or CH.sub.2. However, at least one of X.sub.A or Y.sub.A is an oxygen atom, a sulfur atom, or NH.
(45) When at least one of X.sub.A or Y.sub.A in the formulae (TEMP-16) to (TEMP-33) is NH or CH.sub.2, the monovalent heterocyclic groups derived from the cyclic structures represented by the formulae (TEMP-16) to (TEMP-33) include a monovalent group derived by removing one hydrogen atom from NH, or CH.sub.2.
(46) Substituted Heterocyclic Groups Including Nitrogen Atom (Specific Example Group G2B1):
(47) (9-phenyl)carbazolyl group, (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, (9-naphthyl)carbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, methylbenzimidazolyl group, ethylbenzimidazolyl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenylquinazolinyl group, and biphenylquinazolinyl group.
Substituted Heterocyclic Groups Including Oxygen Atom (Specific Example Group G2B2):
phenyldibenzofuranyl group, methyldibenzofuranyl group, t-butyldibenzofuranyl group, and monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
Substituted Heterocyclic Groups Including Sulfur Atom (Specific Example Group G2B3):
phenyldibenzothiophenyl group, methyldibenzothiophenyl group, t-butyldibenzothiophenyl group, and monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
Groups Obtained by Substituting at Least One Hydrogen Atom of Monovalent Heterocyclic Group Derived from Cyclic Structures Represented by Formulae (TEMP-16) to (TEMP-33) with Substituent (Specific Example Group G2B4):
(48) The “at least one hydrogen atom of a monovalent heterocyclic group” means at least one hydrogen atom selected from a hydrogen atom bonded to a ring carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom of at least one of X.sub.A or Y.sub.A in a form of NH, and a hydrogen atom of one of X.sub.A and Y.sub.A in a form of a methylene group (CH.sub.2).
(49) Substituted or Unsubstituted Alkyl Group
(50) Specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” mentioned herein include unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B below). (Herein, an unsubstituted alkyl group refers to an “unsubstituted alkyl group” in a “substituted or unsubstituted alkyl group,” and a substituted alkyl group refers to a “substituted alkyl group” in a “substituted or unsubstituted alkyl group.”) A simply termed “alkyl group” herein includes both of “unsubstituted alkyl group” and “substituted alkyl group.”
(51) The “substituted alkyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkyl group” with a substituent. Specific examples of the “substituted alkyl group” include a group derived by substituting at least one hydrogen atom of an “unsubstituted alkyl group” (specific example group G3A) below with a substituent, and examples of the substituted alkyl group (specific example group G3B) below. Herein, the alkyl group for the “unsubstituted alkyl group” refers to a chain alkyl group. Accordingly, the “unsubstituted alkyl group” include linear “unsubstituted alkyl group” and branched “unsubstituted alkyl group.” It should be noted that the examples of the “unsubstituted alkyl group” and the “substituted alkyl group” mentioned herein are merely exemplary, and the “substituted alkyl group” mentioned herein includes a group derived by further substituting a hydrogen atom bonded to a carbon atom of a skeleton of the “substituted alkyl group” in the specific example group G3B, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted alkyl group” in the specific example group G3B.
(52) Unsubstituted Alkyl Group (Specific Example Group G3A):
(53) methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, and t-butyl group.
(54) Substituted Alkyl Group (Specific Example Group G3B):
(55) heptafluoropropyl group (including isomer thereof), pentafluoroethyl group, 2,2,2-trifluoroethyl group, and trifluoromethyl group.
(56) Substituted or Unsubstituted Alkenyl Group
(57) Specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” mentioned herein include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B). (Herein, an unsubstituted alkenyl group refers to an “unsubstituted alkenyl group” in a “substituted or unsubstituted alkenyl group,” and a substituted alkenyl group refers to a “substituted alkenyl group” in a “substituted or unsubstituted alkenyl group.”) A simply termed “alkenyl group” herein includes both of “unsubstituted alkenyl group” and “substituted alkenyl group.”
(58) The “substituted alkenyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkenyl group” with a substituent. Specific examples of the “substituted alkenyl group” include an “unsubstituted alkenyl group” (specific example group G4A) substituted by a substituent, and examples of the substituted alkenyl group (specific example group G4B) below. It should be noted that the examples of the “unsubstituted alkenyl group” and the “substituted alkenyl group” mentioned herein are merely exemplary, and the “substituted alkenyl group” mentioned herein includes a group derived by further substituting a hydrogen atom of a skeleton of the “substituted alkenyl group” in the specific example group G4B with a substituent, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted alkenyl group” in the specific example group G4B with a substituent.
(59) Unsubstituted Alkenyl Group (Specific Example Group G4A):
(60) vinyl group, allyl group, 1-butenyl group, 2-butenyl group, and 3-butenyl group.
(61) Substituted Alkenyl Group (Specific Example Group G4B):
(62) 1,3-butanedienyl group, 1-methylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, and 1,2-dimethylallyl group.
(63) Substituted or Unsubstituted Alkynyl Group
(64) Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” mentioned herein include unsubstituted alkynyl groups (specific example group G5A) below. (Herein, an unsubstituted alkynyl group refers to an “unsubstituted alkynyl group” in a “substituted or unsubstituted alkynyl group,” and a substituted alkynyl group refers to a “substituted alkynyl group” in a “substituted or unsubstituted alkynyl group.”) A simply termed “alkynyl group” herein includes both of “unsubstituted alkynyl group” and “substituted alkynyl group.”
(65) The “substituted alkynyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkynyl group” with a substituent. Specific examples of the “substituted alkynyl group” include a group derived by substituting at least one hydrogen atom of the “unsubstituted alkynyl group” (specific example group G5A) below with a substituent.
(66) Unsubstituted Alkynyl Group (Specific Example Group G5A):
(67) ethynyl group
(68) Substituted or Unsubstituted Cycloalkyl Group
(69) Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” mentioned herein include unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B). (Herein, an unsubstituted cycloalkyl group refers to an “unsubstituted cycloalkyl group” in a “substituted or unsubstituted cycloalkyl group,” and a substituted cycloalkyl group refers to a “substituted cycloalkyl group” in a “substituted or unsubstituted cycloalkyl group.”) A simply termed “cycloalkyl group” herein includes both of “unsubstituted cycloalkyl group” and “substituted cycloalkyl group.”
(70) The “substituted cycloalkyl group” refers to a group derived by substituting at least one hydrogen atom of an “unsubstituted cycloalkyl group” with a substituent. Specific examples of the “substituted cycloalkyl group” include a group derived by substituting at least one hydrogen atom of the “unsubstituted cycloalkyl group” (specific example group G6A) below with a substituent, and examples of the substituted cycloalkyl group (specific example group G6B) below. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group” mentioned herein are merely exemplary, and the “substituted cycloalkyl group” mentioned herein includes a group derived by substituting at least one hydrogen atom bonded to a carbon atom of a skeleton of the “substituted cycloalkyl group” in the specific example group G6B with a substituent, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted cycloalkyl group” in the specific example group G6B with a substituent.
(71) Unsubstituted Cycloalkyl Group (Specific Example Group G6A): cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, and 2-norbornyl group.
(72) Substituted Cycloalkyl Group (Specific Example Group G6B):
(73) 4-methylcyclohexyl group
(74) Group Represented by —Si(R.sub.901)(R.sub.902)(R.sub.903):
(75) Specific examples (specific example group G7) of the group represented herein by —Si(R.sub.901)(R.sub.902)(R.sub.903) include: —Si(G1)(G1)(G1); —Si(G1)(G2)(G2); —Si(G1)(G1)(G2); —Si(G2)(G2)(G2); —Si(G3)(G3)(G3); and —Si(G6)(G6)(G6).
(76) Herein: G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
(77) G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
(78) G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3; and
(79) G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6.
(80) A plurality of G1 in —Si(G1)(G1)(G1) are mutually the same or different.
(81) A plurality of G2 in —Si(G1)(G2)(G2) are mutually the same or different.
(82) A plurality of G1 in —Si(G1)(G1)(G2) are mutually the same or different.
(83) A plurality of G2 in —Si(G2)(G2)(G2) are mutually the same or different.
(84) The plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different.
(85) A plurality of G6 in —Si(G6)(G6)(G6) are mutually the same or different.
(86) Group Represented by —O—(R.sub.904)
(87) Specific examples (specific example group G8) of a group represented by —O—(R.sub.904) herein include —O(G1); —O(G2); —O(G3); and —O(G6).
(88) Herein: G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
(89) G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
(90) G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3; and
(91) G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6.
(92) Group Represented by —S—(R.sub.905)
(93) Specific examples (specific example group G9) of a group represented herein by —S—(R.sub.905) include: —S(G1); —S(G2); —S(G3); and —S(G6).
(94) Herein: G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
(95) G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
(96) G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3; and
(97) G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6.
(98) Group Represented by —N(R.sub.906)(R.sub.907)
(99) Specific examples (specific example group G10) of a group represented herein by —N(R.sub.906)(R.sub.907) include: —N(G1)(G1); —N(G2)(G2); —N(G1)(G2); —N(G3)(G3); and —N(G6)(G6).
(100) Herein: G1 represents a “substituted or unsubstituted aryl group” in the specific example group G1;
(101) G2 represents a “substituted or unsubstituted heterocyclic group” in the specific example group G2;
(102) G3 represents a “substituted or unsubstituted alkyl group” in the specific example group G3; and
(103) G6 represents a “substituted or unsubstituted cycloalkyl group” in the specific example group G6.
(104) A plurality of G1 in —N(G1)(G1) are mutually the same or different.
(105) A plurality of G2 in —N(G2)(G2) are mutually the same or different.
(106) A plurality of G3 in —N(G3)(G3) are mutually the same or different.
(107) A plurality of G6 in —N(G6)(G6)) are mutually the same or different.
(108) Halogen Atom
(109) Specific examples (specific example group G11) of “halogen atom” mentioned herein include a fluorine atom, chlorine atom, bromine atom, and iodine atom.
(110) Substituted or Unsubstituted Fluoroalkyl Group
(111) The “substituted or unsubstituted fluoroalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom bonded to at least one of carbon atoms forming an alkyl group in the “substituted or unsubstituted alkyl group” with a fluorine atom, and also includes a group (perfluoro group) derived by substituting all of hydrogen atoms bonded to carbon atoms forming the alkyl group in the “substituted or unsubstituted alkyl group” with fluorine atoms. An “unsubstituted fluoroalkyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms. The “substituted fluoroalkyl group” refers to a group derived by substituting at least one hydrogen atom in a “fluoroalkyl group” with a substituent. It should be noted that the examples of the “substituted fluoroalkyl group” mentioned herein includes a group derived by further substituting at least one hydrogen atom bonded to a carbon atom of an alkyl chain of a “substituted fluoroalkyl group” with a substituent, and a group derived by further substituting at least one hydrogen atom of a substituent of the “substituted fluoroalkyl group” with a substituent. Specific examples of the “substituted fluoroalkyl group” include a group derived by substituting at least one hydrogen atom of the “alkyl group” (specific example group G3) with a fluorine atom.
(112) Substituted or Unsubstituted Haloalkyl Group
(113) The “substituted or unsubstituted haloalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom bonded to carbon atoms forming the alkyl group in the “substituted or unsubstituted alkyl group” with a halogen atom, and also includes a group derived by substituting all hydrogen atoms bonded to carbon atoms forming the alkyl group in the “substituted or unsubstituted alkyl group” with halogen atoms. An “unsubstituted haloalkyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms. The “substituted haloalkyl group” refers to a group derived by substituting at least one hydrogen atom in a “haloalkyl group” with a substituent. It should be noted that the examples of the “substituted haloalkyl group” mentioned herein includes a group derived by further substituting at least one hydrogen atom bonded to a carbon atom of an alkyl chain of a “substituted haloalkyl group” with a substituent, and a group derived by further substituting at least one hydrogen atom of a substituent of the “substituted haloalkyl group” with a substituent. Specific examples of the “substituted haloalkyl group” include a group derived by substituting at least one hydrogen atom of the “alkyl group” (specific example group G3) with a halogen atom. The haloalkyl group is sometimes referred to as a halogenated alkyl group.
(114) Substituted or Unsubstituted Alkoxy Group
(115) Specific examples of a “substituted or unsubstituted alkoxy group” mentioned herein include a group represented by —O(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. An “unsubstituted alkoxy group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms.
(116) Substituted or Unsubstituted Alkylthio Group
(117) Specific examples of a “substituted or unsubstituted alkylthio group” mentioned herein include a group represented by —S(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. An “unsubstituted alkylthio group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms.
(118) Substituted or Unsubstituted Aryloxy Group
(119) Specific examples of a “substituted or unsubstituted aryloxy group” mentioned herein include a group represented by —O(G1), G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. An “unsubstituted aryloxy group” has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
(120) Substituted or Unsubstituted Arylthio Group
(121) Specific examples of a “substituted or unsubstituted arylthio group” mentioned herein include a group represented by —S(G1), G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. An “unsubstituted arylthio group” has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
(122) Substituted or Unsubstituted Trialkylsilyl Group
(123) Specific examples of a “trialkylsilyl group” mentioned herein include a group represented by —Si(G3)(G3)(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. The plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different. Each of the alkyl groups in the “trialkylsilyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
(124) Substituted or Unsubstituted Aralkyl Group
(125) Specific examples of a “substituted or unsubstituted aralkyl group” mentioned herein include a group represented by (G3)-(G1), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3, G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. Accordingly, the “aralkyl group” is a group derived by substituting a hydrogen atom of the “alkyl group” with a substituent in a form of the “aryl group,” which is an example of the “substituted alkyl group.” An “unsubstituted aralkyl group,” which is an “unsubstituted alkyl group” substituted by an “unsubstituted aryl group,” has, unless otherwise specified herein, 7 to 50 carbon atoms, preferably 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms.
(126) Specific examples of the “substituted or unsubstituted aralkyl group” include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.
(127) Preferable examples of the substituted or unsubstituted aryl group mentioned herein include, unless otherwise specified herein, a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.
(128) Preferable examples of the substituted or unsubstituted heterocyclic group mentioned herein include, unless otherwise specified herein, a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
(129) The carbazolyl group mentioned herein is, unless otherwise specified herein, specifically a group represented by one of formulae below.
(130) ##STR00012##
(131) The (9-phenyl)carbazolyl group mentioned herein is, unless otherwise specified herein, specifically a group represented by one of formulae below.
(132) ##STR00013##
(133) In the formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
(134) The dibenzofuranyl group and dibenzothiophenyl group mentioned herein are, unless otherwise specified herein, each specifically represented by one of formulae below.
(135) ##STR00014##
(136) In the formulae (TEMP-34) to (TEMP-41), * represents a bonding position.
(137) Preferable examples of the substituted or unsubstituted alkyl group mentioned herein include, unless otherwise specified herein, a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t-butyl group.
(138) Substituted or Unsubstituted Arylene Group
(139) The “substituted or unsubstituted arylene group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on an aryl ring of the “substituted or unsubstituted aryl group.” Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include a divalent group derived by removing one hydrogen atom on an aryl ring of the “substituted or unsubstituted aryl group” in the specific example group G1.
(140) Substituted or Unsubstituted Divalent Heterocyclic Group
(141) The “substituted or unsubstituted divalent heterocyclic group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on a heterocyclic ring of the “substituted or unsubstituted heterocyclic group.” Specific examples of the “substituted or unsubstituted heterocyclic group” (specific example group G13) include a divalent group derived by removing one hydrogen atom on a heterocyclic ring of the “substituted or unsubstituted heterocyclic group” in the specific example group G2.
(142) Substituted or Unsubstituted Alkylene Group
(143) The “substituted or unsubstituted alkylene group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on an alkyl ring of the “substituted or unsubstituted alkyl group.” Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include a divalent group derived by removing one hydrogen atom on an alkyl ring of the “substituted or unsubstituted alkyl group” in the specific example group G3.
(144) The substituted or unsubstituted arylene group mentioned herein is, unless otherwise specified herein, preferably any one of groups represented by formulae (TEMP-42) to (TEMP-68) below.
(145) ##STR00015## ##STR00016##
(146) ##STR00017##
(147) In the formulae (TEMP-42) to (TEMP-52), Q.sub.1 to Q.sub.10 each independently are a hydrogen atom or a substituent.
(148) In the formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
(149) ##STR00018## ##STR00019##
(150) In the formulae (TEMP-53) to (TEMP-62), Q.sub.1 to Q.sub.10 each independently are a hydrogen atom or a substituent.
(151) In the formulae, Q.sub.9 and Q.sub.10 may be mutually bonded through a single bond to form a ring.
(152) In the formulae (TEMP-53) to (TEMP-62), * represents a bonding position.
(153) ##STR00020##
(154) In the formulae (TEMP-63) to (TEMP-68), Q.sub.1 to Q.sub.8 each independently are a hydrogen atom or a substituent.
(155) In the formulae (TEMP-63) to (TEMP-68), * represents a bonding position.
(156) The substituted or unsubstituted divalent heterocyclic group mentioned herein is, unless otherwise specified herein, preferably a group represented by any one of formulae (TEMP-69) to (TEMP-102) below.
(157) ##STR00021##
(158) ##STR00022##
(159) ##STR00023##
(160) In the formulae (TEMP-69) to (TEMP-82), Q.sub.1 to Q.sub.9 each independently are a hydrogen atom or a substituent.
(161) ##STR00024## ##STR00025##
(162) ##STR00026## ##STR00027##
(163) In the formulae (TEMP-83) to (TEMP-102), Q.sub.1 to Q.sub.8 each independently are a hydrogen atom or a substituent.
(164) The substituent mentioned herein has been described above.
(165) Instance of “Bonded to Form Ring”
(166) Instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded” mentioned herein refer to instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring, “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring,” and “at least one combination of adjacent two or more (of . . . ) are not mutually bonded.”
(167) Instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring” and “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring” mentioned herein (these instances will be sometimes collectively referred to as an instance of “bonded to form a ring” hereinafter) will be described below. An anthracene compound having a basic skeleton in a form of an anthracene ring and represented by a formula (TEMP-103) below will be used as an example for the description.
(168) ##STR00028##
(169) For instance, when “at least one combination of adjacent two or more of” R.sub.921 to R.sub.930 “are mutually bonded to form a ring,” the pair of adjacent ones of R.sub.921 to R.sub.930 (i.e. the combination at issue) is a pair of R.sub.921 and a pair of R.sub.922, R.sub.922 and R.sub.923, a pair of R.sub.923 and R.sub.924, a pair of R.sub.924 and R.sub.930, a pair of R.sub.930 and R.sub.925, a pair of R.sub.925 and R.sub.926, a pair of R.sub.926 and R.sub.927, a pair of R.sub.927 and R.sub.928, a pair of R.sub.928 and R.sub.929, or a pair of R.sub.929 and R.sub.921.
(170) The term “at least one combination” means that two or more of the above combinations of adjacent two or more of R.sub.921 to R.sub.930 may simultaneously form rings. For instance, when R.sub.921 and R.sub.922 are mutually bonded to form a ring Q.sub.A and R.sub.925 and R.sub.926 are simultaneously mutually bonded to form a ring Q.sub.B, the anthracene compound represented by the formula (TEMP-103) is represented by a formula (TEMP-104) below.
(171) ##STR00029##
(172) The instance where the “combination of adjacent two or more” form a ring means not only an instance where the “two” adjacent components are bonded but also an instance where adjacent “three or more” are bonded. For instance, R.sub.921 and R.sub.922 are mutually bonded to form a ring Q.sub.A and R.sub.922, R.sub.923 are mutually bonded to form a ring Q.sub.C, and mutually adjacent three components (R.sub.921, R.sub.922 and R.sub.923) are mutually bonded to form a ring fused to the anthracene basic skeleton. In this case, the anthracene compound represented by the formula (TEMP-103) is represented by a formula (TEMP-105) below. In the formula (TEMP-105) below, the ring Q.sub.A and the ring Q.sub.C share R.sub.922.
(173) ##STR00030##
(174) The formed “monocyclic ring” or “fused ring” may be, in terms of the formed ring in itself, a saturated ring or an unsaturated ring. When the “combination of adjacent two” form a “monocyclic ring” or a “fused ring,” the “monocyclic ring” or “fused ring” may be a saturated ring or an unsaturated ring. For instance, the ring Q.sub.A and the ring Q.sub.B formed in the formula (TEMP-104) are each independently a “monocyclic ring” or a “fused ring.” Further, the ring Q.sub.A and the ring Q.sub.C formed in the formula (TEMP-105) are each a “fused ring.” The ring Q.sub.A and the ring Q.sub.C in the formula (TEMP-105) are fused to form a fused ring. When the ring Q.sub.A in the formula (TEMP-104) is a benzene ring, the ring Q.sub.A is a monocyclic ring. When the ring Q.sub.A in the formula (TEMP-104) is a naphthalene ring, the ring Q.sub.A is a fused ring.
(175) The “unsaturated ring” represents an aromatic hydrocarbon ring or an aromatic heterocycle. The “saturated ring” represents an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
(176) Specific examples of the aromatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G1 with a hydrogen atom.
(177) Specific examples of the aromatic heterocyclic ring include a ring formed by terminating a bond of an aromatic heterocyclic group in the specific example of the specific example group G2 with a hydrogen atom.
(178) Specific examples of the aliphatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G6 with a hydrogen atom.
(179) The phrase “to form a ring” herein means that a ring is formed only by a plurality of atoms of a basic skeleton, or by a combination of a plurality of atoms of the basic skeleton and one or more optional atoms. For instance, the ring Q.sub.A formed by mutually bonding R.sub.921 and R.sub.922 shown in the formula (TEMP-104) is a ring formed by a carbon atom of the anthracene skeleton bonded with R.sub.921, a carbon atom of the anthracene skeleton bonded with R.sub.922, and one or more optional atoms. Specifically, when the ring Q.sub.A is a monocyclic unsaturated ring formed by R.sub.921 and R.sub.922, the ring formed by a carbon atom of the anthracene skeleton bonded with R.sub.921, a carbon atom of the anthracene skeleton bonded with R.sub.922, and four carbon atoms is a benzene ring.
(180) The “optional atom” is, unless otherwise specified herein, preferably at least one atom selected from the group consisting of a carbon atom, nitrogen atom, oxygen atom, and sulfur atom. A bond of the optional atom (e.g. a carbon atom and a nitrogen atom) not forming a ring may be terminated by a hydrogen atom or the like or may be substituted by an “optional substituent” described later. When the ring includes an optional element other than carbon atom, the resultant ring is a heterocycle.
(181) The number of “one or more optional atoms” forming the monocyclic ring or fused ring is, unless otherwise specified herein, preferably in a range from 2 to 15, more preferably in a range from 3 to 12, further preferably in a range from 3 to 5.
(182) Unless otherwise specified herein, the ring, which may be a “monocyclic ring” or “fused ring,” is preferably a “monocyclic ring.”
(183) Unless otherwise specified herein, the ring, which may be a “saturated ring” or “unsaturated ring,” is preferably an “unsaturated ring.”
(184) Unless otherwise specified herein, the “monocyclic ring” is preferably a benzene ring.
(185) Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring.
(186) When “at least one combination of adjacent two or more” (of . . . ) are “mutually bonded to form a substituted or unsubstituted monocyclic ring” or “mutually bonded to form a substituted or unsubstituted fused ring,” unless otherwise specified herein, at least one combination of adjacent two or more of components are preferably mutually bonded to form a substituted or unsubstituted “unsaturated ring” formed of a plurality of atoms of the basic skeleton, and 1 to 15 atoms of at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
(187) When the “monocyclic ring” or the “fused ring” has a substituent, the substituent is the substituent described in later-described “optional substituent.” When the “monocyclic ring” or the “fused ring” has a substituent, specific examples of the substituent are the substituents described in the above under the subtitle “Substituents Mentioned Herein.”
(188) When the “saturated ring” or the “unsaturated ring” has a substituent, the substituent is, for instance, the substituent described in later-described “optional substituent.” When the “monocyclic ring” or the “fused ring” has a substituent, specific examples of the substituent are the substituents described in the above under the subtitle “Substituents Mentioned Herein.”
(189) The above is the description for the instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring” and “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring” mentioned herein (sometimes referred to as an instance “bonded to form a ring”.
(190) Substituent for Substituted or Unsubstituted Group
(191) In an exemplary embodiment herein, a substituent for the substituted or unsubstituted group (sometimes referred to as an “optional substituent” hereinafter) is, for instance, a group selected from the group consisting of an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R.sub.901)(R.sub.902)(R.sub.903), —O—(R.sub.904), —S—(R.sub.905), —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms.
(192) Herein, R.sub.901 to R.sub.907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(193) When two or more R.sub.901 are present, the two or more R.sub.901 are mutually the same or different.
(194) When two or more R.sub.902 are present, the two or more R.sub.902 are mutually the same or different.
(195) When two or more R.sub.903 are present, the two or more R.sub.903 are mutually the same or different.
(196) When two or more R.sub.904 are present, the two or more R.sub.904 are mutually the same or different.
(197) When two or more R.sub.905 are present, the two or more R.sub.905 are mutually the same or different.
(198) When two or more R.sub.906 are present, the two or more R.sub.905 are mutually the same or different.
(199) When two or more R.sub.907 are present, the two or more R.sub.907 are mutually the same or different.
(200) In an exemplary embodiment, a substituent for the substituted or unsubstituted group is selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring carbon atoms, and a heterocyclic group having 5 to 50 ring atoms.
(201) In an exemplary embodiment, a substituent for the substituted or unsubstituted group is selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.
(202) Specific examples of the above optional substituent are the same as the specific examples of the substituent described in the above under the subtitle “Substituent Mentioned Herein.”
(203) Unless otherwise specified herein, adjacent ones of the optional substituents may form a “saturated ring” or an “unsaturated ring,” preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted saturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.
(204) Unless otherwise specified herein, the optional substituent may further include a substituent. Examples of the substituent for the optional substituent are the same as the examples of the optional substituent.
(205) Herein, numerical ranges represented by “AA to BB” represents a range whose lower limit is the value (AA) recited before “to” and whose upper limit is the value (BB) recited after “to.”
First Exemplary Embodiment
(206) Organic Electroluminescence Device
(207) An organic EL device according to a first exemplary embodiment includes an anode, a cathode, a first emitting layer and a second emitting layer interposed between the anode and the cathode, the first and second emitting layers being in a direct contact with each other, and a first electron transporting layer between the cathode and the first and second emitting layers being in a direct contact with each other. The first emitting layer contains a first compound represented by a formula (1) below as a first host material, the first compound containing at least one group represented by a formula (11) below. The second emitting layer contains a second compound represented by a formula (2) below as a second host material. The first electron transporting layer contains a third compound represented by a formula (3) below.
(208) Herein, the “host material” refers to, for instance, a material that accounts for “50 mass % or more of the layer.” Accordingly, for instance, the first emitting layer contains 50 mass % or more of the first compound represented by the formula (1) with respect to a total mass of the first emitting layer. The second emitting layer contains 50 mass % or more of the second compound represented by the formula (2) with respect to a total mass of the second emitting layer. Moreover, for instance, the “host material” may accounts for 60 mass % or more of the layer, 70 mass % or more of the layer, 80 mass % or more of the layer, 90 mass % or more of the layer, or 95 mass % or more of the layer.
(209) In the organic EL device according to the first exemplary embodiment, it is also preferable that the first emitting layer is interposed between the anode and the second emitting layer.
(210) In the organic EL device according to the first exemplary embodiment, it is also preferable that the second emitting layer is interposed between the anode and the first emitting layer.
(211) The organic EL device according to the first exemplary embodiment may one or more organic layer(s) in addition to the first emitting layer, the second emitting layer, and the first electron transporting layer. Examples of the organic layer include at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an emitting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, and an electron blocking layer.
(212) In the organic EL device according to the first exemplary embodiment, the organic layer may consist of the first emitting layer, the second emitting layer, and the first electron transporting layer. Alternatively, the organic layer may further include, for instance, at least one layer selected from the group consisting of the hole injecting layer, the hole transporting layer, the electron injecting layer, the electron transporting layer, the hole blocking layer, and the electron blocking layer.
(213) Electron Transporting Layer
(214) The organic EL device of the first exemplary embodiment preferably includes at least one of a second electron transporting layer or a third electron transporting layer as a further electron transporting layer in addition to the first electron transporting layer.
(215) The second electron transporting layer is preferably interposed between the first electron transporting layer and the cathode.
(216) The third electron transporting layer is preferably interposed between the first electron transporting layer and the emitting layer.
(217) When the organic EL device of the first exemplary embodiment includes a plurality of electron transporting layers, one, which is provided closer to the emitting layer, of the plurality of electron transporting layers is sometimes referred to as the hole blocking layer.
(218) In the organic EL device of the first exemplary embodiment, it is also preferable that the first electron transporting layer is in direct contact with one, which is provided closer to the cathode, of the first emitting layer and the second emitting layer.
(219) It is also preferable that the organic EL device of the first exemplary embodiment further includes the second electron transporting layer between the first electron transporting layer and the cathode.
(220) In the organic EL device of the first exemplary embodiment, it is also preferable that the first electron transporting layer is in direct contact with one, which is provided closer to the cathode, of the first emitting layer and the second emitting layer, and the second electron transporting layer is interposed between the first electron transporting layer and the cathode.
(221) In the organic EL device of the first exemplary embodiment, it is preferable that the second electron transporting layer contains a fourth compound represented by a formula (3) below and the third compound contained in the first electron transporting layer is different in structure from the fourth compound contained in the second electron transporting layer.
(222) In the organic EL device according to the first exemplary embodiment, the first electron transporting layer and the second electron transporting layer are preferably in direct contact with each other.
(223) It is also preferable that the organic EL device according to the first exemplary embodiment further includes a third electron transporting layer between the first electron transporting layer and the first and second emitting layers being in direct contact with each other.
(224) In the organic EL device according to the first exemplary embodiment, it is preferable that the third electron transporting layer includes a fifth compound represented by a formula (3) below, and the third compound contained in the first electron transporting layer and the fifth compound contained in the third electron transporting layer are different from each other in structure.
(225) In the organic EL device according to the first exemplary embodiment, the first electron transporting layer and the third electron transporting layer are preferably in direct contact with each other.
(226) In the organic EL device of the first exemplary embodiment, it is preferable that the third electron transporting layer is in direct contact with one, which is provided closer to the cathode, of the first emitting layer and the second emitting layer.
(227) Hole Transporting Layer
(228) The organic EL device according to the first exemplary embodiment preferably includes a hole transporting layer between the anode and the emitting layer.
(229) Schematic Structure of Organic EL Devices
(230)
(231) An organic EL device 1 includes a light-transmissive substrate 2, an anode 3, a cathode 4, and an organic layer 10 provided between the anode 3 and the cathode 4. The organic layer 10 includes a hole injecting layer 6, a hole transporting layer 7, a first emitting layer 51, a second emitting layer 52, a first electron transporting layer 81, a second electron transporting layer 82, and an electron injecting layer 9, which are sequentially laminated on the anode 3.
(232)
(233) An organic EL device 1A includes the light-transmissive substrate 2, the anode 3, the cathode 4, and an organic layer 10A provided between the anode 3 and the cathode 4. The organic layer 10A includes the hole injecting layer 6, the hole transporting layer 7, the first emitting layer 51, the second emitting layer 52, a third electron transporting layer 83, the first electron transporting layer 81, and the electron injecting layer 9, which are sequentially laminated on the anode 3.
(234)
(235) An organic EL device 1B includes the light-transmissive substrate 2, the anode 3, the cathode 4, and an organic layer 10B provided between the anode 3 and the cathode 4. The organic layer 10B includes the hole injecting layer 6, the hole transporting layer 7, the second emitting layer 52, the first emitting layer 51, the first electron transporting layer 81, the second electron transporting layer 82, and the electron injecting layer 9, which are sequentially laminated on the anode 3.
(236)
(237) An organic EL device 1C includes the light-transmissive substrate 2, the anode 3, the cathode 4, and an organic layer 10C provided between the anode 3 and the cathode 4. The organic layer 10C includes the hole injecting layer 6, the hole transporting layer 7, the second emitting layer 52, the first emitting layer 51, the third electron transporting layer 83, the first electron transporting layer 81, and the electron injecting layer 9, which are sequentially laminated on the anode 3.
(238) First Emitting Layer
(239) The first emitting layer is in direct contact with the second emitting layer. The first emitting layer includes a first host material in a form of a first compound represented by a formula (1). The first compound has at least one group represented by a formula (11) below.
(240) The first emitting layer preferably has a compound that emits light having a maximum peak wavelength in a range from 430 nm to 480 nm.
(241) The first emitting layer preferably further contains a seventh compound that fluoresces.
(242) The seventh compound is preferably a compound that emits light having a maximum peak wavelength in a range from 430 nm to 480 nm.
(243) In the organic EL device of the exemplary embodiment, when the first emitting layer contains the first compound and the seventh compound, the first compound is preferably a host material (occasionally also referred to as a matrix material) and the seventh compound is preferably a dopant material (occasionally also referred to as a guest material, emitter or a luminescent material).
(244) The first emitting layer preferably does not contain a phosphorescent material as the dopant material.
(245) Moreover, the first emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of the heavy-metal complex herein include iridium complex, osmium complex, and platinum complex.
(246) The first emitting layer also preferably does not contain a metal complex.
(247) First Compound
(248) The first compound is a compound represented by a formula (1) below. The first compound has at least one group represented by the formula (11) below.
(249) ##STR00031##
(250) In the formula (1), R.sub.101 to R.sub.110 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or the group represented by the formula (11).
(251) At least one of R.sub.101 to R.sub.110 is the group represented by the formula (11).
(252) When a plurality of groups represented by the formula (11) are present, the plurality of groups represented by the formula (11) are mutually the same or different.
(253) L.sub.101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
(254) Ar.sub.101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(255) mx is 0, 1, 2, 3, 4 or 5.
(256) When two or more L.sub.101 are present, two or more L.sub.101 are mutually the same or different.
(257) When two or more Ar.sub.101 are present, two or more Ar.sub.101 are mutually the same or different.
(258) A mark * in the formula (11) represents a bonding position to a pyrene ring in the formula (1).
(259) In the first compound represented by the formula (1): R.sub.901, R.sub.902, R.sub.903, R.sub.904, R.sub.905, R.sub.906, R.sub.907, R.sub.801 and R.sub.802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(260) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(261) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(262) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different;
(263) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different;
(264) when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different;
(265) when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different;
(266) when a plurality of R.sub.907 are present, the plurality of R.sub.907 are mutually the same or different;
(267) when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different; and
(268) when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different.
(269) The group represented by the formula (11) is preferably a group represented by a formula (111) below.
(270) ##STR00032##
(271) In the formula (111): X.sub.1 is CR.sub.123R.sub.124, an oxygen atom, a sulfur atom, or NR.sub.125;
(272) L.sub.111 and L.sub.112 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(273) ma is 0, 1, 2, 3, or 4;
(274) mb is 0, 1, 2, 3, or 4;
(275) ma+mb is 0, 1, 2, 3, or 4;
(276) Ar.sub.101 represents the same as Ar.sub.101 in the formula (11); R.sub.121, R.sub.122, R.sub.123, R.sub.124, and R.sub.125 are each dependently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(277) mc is 3;
(278) three R.sub.121 are mutually the same or different;
(279) md is 3; and
(280) three R.sub.122 are mutually the same or different.
(281) Among positions *1 to *8 of carbon atoms in the cyclic structure represented by a formula (111a) below in the group represented by the formula (111), L.sub.111 is bonded to one of positions *1 to *4, R.sub.121 is bonded to three positions of the rest of *1 to *4, L.sub.112 is bonded to one of positions *5 to *8, and R.sub.122 is bonded to three positions of the rest of *5 to *8.
(282) ##STR00033##
(283) For instance, in the group represented by the formula (111), when L.sub.111 and L.sub.112 are bonded to *2 and *7 positions, respectively, of the carbon atom of the cyclic structure represented by the formula (111a), the group represented by the formula (111) is represented by a formula (111b) below.
(284) ##STR00034##
(285) In the formula (111b): X.sub.1, L.sub.111, L.sub.112, ma, mb, Ar.sub.101, R.sub.121, R.sub.122, R.sub.123, R.sub.124, and R.sub.125 each independently represent the same as X.sub.1, L.sub.111, L.sub.112, ma, mb, Ar.sub.101, R.sub.121, R.sub.122, R.sub.123, R.sub.124, and R.sub.125 in the formula (111);
(286) a plurality of R.sub.121 are mutually the same or different; and
(287) a plurality of R.sub.122 are mutually the same or different.
(288) In the organic EL device of the exemplary embodiment, the group represented by the formula (111) is preferably a group represented by the formula (111b).
(289) In the organic EL device of the exemplary embodiment, it is preferable that ma is 0, 1 or 2 and mb is 0, 1 or 2.
(290) In the organic EL device of the exemplary embodiment, it is preferable that ma is 0 or 1 and mb is 0 or 1.
(291) The group represented by the formula (111) in which ma is 0 and mb is 1 is represented by a formula (111c) below.
(292) ##STR00035##
(293) In the formula (111c), X.sub.1, L.sub.112, mc, md, Ar.sub.101, R.sub.121 and R.sub.122 each independently represent the same as X.sub.1, L.sub.112, mc, md, Ar.sub.101, R.sub.121 and R.sub.122 in the formula (111).
(294) In the organic EL device according to the exemplary embodiment, Ar.sub.101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(295) In the organic EL device of the exemplary embodiment, Ar.sub.101 is preferably a substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted phenanthryl group, or substituted or unsubstituted fluorenyl group.
(296) In the organic EL device of the exemplary embodiment, Ar.sub.101 is also preferably a group represented by a formula (12), a formula (13), or a formula (14).
(297) ##STR00036##
(298) In the formulae (12), (13), and (14):
(299) R.sub.111 to R.sub.120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.124, a group represented by —COOR.sub.125 a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(300) * in the formulae (12), (13) and (14) represents a bonding position to L.sub.11 in the formula (11), a bonding position to L.sub.112 in the formula (111), or a bonding position to L.sub.112 in the formula (111 b).
(301) It is also preferable that R.sub.124 and R.sub.125 in the formulae (12), (13) and (14) each independently represent the same as R.sub.801 and R.sub.802 described above.
(302) The first compound is preferably represented by a formula (101) below.
(303) ##STR00037##
(304) In the formula (101): R.sub.101 to R.sub.120 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(305) one of R.sub.101 to R.sub.110 represents a bonding position to L.sub.111, and one of R.sub.111 to R.sub.120 represents a bonding position to L.sub.101;
(306) L.sub.101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(307) mx is 0, 1, 2, 3, 4 or 5; and
(308) when two or more L.sub.111 are present, two or more L.sub.111 are mutually the same or different.
(309) The compound represented by the formula (101) in which R.sub.103 is a bonding position to L.sub.111 and R.sub.120 is a bonding position to L.sub.111 is represented by a formula (101A) below.
(310) ##STR00038##
(311) In the formula (101A), R.sub.101, R.sub.102, R.sub.104 to R.sub.119, L.sub.101 and mx respectively represent the same as R.sub.101, R.sub.102, R.sub.104 to R.sub.119, L.sub.101 and mx in the formula (101).
(312) In the organic EL device of the exemplary embodiment, L.sub.111 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
(313) In the organic EL device of the exemplary embodiment, the first compound is preferably represented by a formula (102) below.
(314) ##STR00039##
(315) In the formula (102): R.sub.101 to R.sub.120 each independently represent the same as R.sub.101 to R.sub.120 of the formula (101);
(316) one of R.sub.101 to R.sub.110 represents a bonding position to L.sub.111, and one of R.sub.111 to R.sub.120 represents a bonding position to L.sub.112;
(317) X.sub.1 is CR.sub.123R.sub.124, an oxygen atom, a sulfur atom, or NR.sub.125;
(318) L.sub.111 and L.sub.112 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(319) ma is 0, 1, 2, 3, or 4;
(320) mb is 0, 1, 2, 3, or 4;
(321) ma+mb is 0, 1, 2, 3, or 4;
(322) R.sub.121, R.sub.122, R.sub.123, R.sub.124, and R.sub.125 are each dependently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(323) mc is 3;
(324) three R.sub.121 are mutually the same or different;
(325) md is 3; and
(326) three R.sub.122 are mutually the same or different.
(327) In the compound represented by the formula (102), it is preferable that ma is 0, 1 or 2 and mb is 0, 1 or 2.
(328) In the compound represented by the formula (102), it is preferable that ma is 0 or 1 and mb is 0 or 1.
(329) In the organic EL device of the exemplary embodiment, two or more of R.sub.101 to R.sub.110 are preferably the group represented by the formula (11).
(330) In the organic EL device of the exemplary embodiment, it is preferable that two or more of R.sub.101 to R.sub.110 are the group represented by the formula (11) and Ar.sub.101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(331) In the organic EL device according to the exemplary embodiment, Ar.sub.101 is not a substituted or unsubstituted pyrenyl group;
(332) L.sub.101 is not a substituted or unsubstituted pyrenylene group; and
(333) the substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms for R.sub.101 to R.sub.110 not being the group represented by the formula (11) is not a substituted or unsubstituted pyrenyl group.
(334) In the organic EL device according to the exemplary embodiment, R.sub.101 to R.sub.110 that are not the group represented by the formula (11) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(335) In the organic EL device according to the exemplary embodiment, R.sub.101 to R.sub.110 that are not the group represented by the formula (11) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
(336) In the organic EL device according to the exemplary embodiment, R.sub.101 to R.sub.110 not being the group represented by the formula (11) are each preferably a hydrogen atom.
(337) In the organic EL device of the exemplary embodiment, X.sub.1 is preferably CR.sub.123R.sub.124. For instance, when X.sub.1 is CR.sub.123R.sub.124, the group represented by the formula (111) is represented by a formula (111d) below.
(338) ##STR00040##
(339) In the formula (111d), L.sub.111, L.sub.112, ma, mb, ma+mb, Ar.sub.101, R.sub.121, R.sub.122, R.sub.123, R.sub.124, R.sub.125, mc and md represent the same as L.sub.111, L.sub.112, ma, mb, ma+mb, Ar.sub.101, R.sub.121, R.sub.122, R.sub.123, R.sub.124, R.sub.125, mc and md in the formula (111).
(340) In the organic EL device of the exemplary embodiment, it is preferable that R.sub.123 and R.sub.124 are not bonded to each other.
(341) In the organic EL device of the exemplary embodiment, at least one of L.sub.111 or L.sub.112 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
(342) In the first compound, it is preferable that all groups described as “substituted or unsubstituted” groups are “unsubstituted” groups.
(343) Manufacturing Method of First Compound
(344) The first compound can be manufactured by a known method. The first compound can also be manufactured based on a known method through a known alternative reaction using a known material(s) tailored for the target compound.
(345) Specific Examples of First Compound
(346) Specific examples of the first compound include the following compounds. It should however be noted that the invention is not limited by the specific examples of the first compound.
(347) ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063##
Second Emitting Layer
(348) The second emitting layer is in direct contact with the first emitting layer. The second emitting layer contains a second compound represented by a formula (2) below as a second host material.
(349) The second emitting layer preferably has a compound that emits light having a maximum peak wavelength in a range from 430 nm to 480 nm.
(350) The second emitting layer preferably further contains a sixth compound that fluoresces.
(351) The sixth compound is preferably a compound that emits light having a maximum peak wavelength in a range from 430 nm to 480 nm.
(352) In the organic EL device of the exemplary embodiment, when the second emitting layer contains the second compound and the sixth compound, the second compound is preferably a host material (occasionally also referred to as a matrix material) and the sixth compound is preferably a dopant material (occasionally also referred to as a guest material, emitter or a luminescent material).
(353) The second emitting layer preferably does not contain a phosphorescent material as the dopant material.
(354) Moreover, the second emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of the heavy-metal complex herein include iridium complex, osmium complex, and platinum complex.
(355) The second emitting layer also preferably does not contain a metal complex.
(356) Second Compound
(357) The second compound represented by the formula (2) in the exemplary embodiment will be described.
(358) ##STR00064##
(359) In the formula (2), R.sub.201 to R.sub.208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(360) L.sub.201 and L.sub.202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and
(361) Ar.sub.201 and Ar.sub.202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(362) In the second compound according to the exemplary embodiment: R.sub.901, R.sub.902, R.sub.903, R.sub.904, R.sub.905, R.sub.906, R.sub.907, R.sub.801, and R.sub.802 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(363) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(364) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(365) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different;
(366) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different;
(367) when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different;
(368) when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different;
(369) when a plurality of R.sub.907 are present, the plurality of R.sub.907 are mutually the same or different;
(370) when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different; and
(371) when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different.
(372) In the organic EL device of the exemplary embodiment, it is preferable that R.sub.201 to R.sub.208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group or a nitro group;
(373) L.sub.201 to L.sub.202 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and
(374) Ar.sub.201 and Ar.sub.202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(375) In the organic EL device of the exemplary embodiment, it is preferable that L.sub.201 and L.sub.202 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms and Ar.sub.201 and Ar.sub.202 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(376) In the organic EL device of the exemplary embodiment, it is preferable that Ar.sub.201 and Ar.sub.202 are each independently a phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, diphenylfluorenyl group, dimethylfluorenyl group, benzodiphenylfluorenyl group, benzodimethylfluorenyl group, dibenzofuranyl group, dibenzothienyl group, naphthobenzofuranyl group, or naphthobenzothienyl group.
(377) In the organic EL device of the exemplary embodiment, the second compound represented by the formula (2) is preferably a compound represented by a formula (201), a formula (202), a formula (203), a formula (204), a formula (205), a formula (206), a formula (207), a formula (208), a formula (209) or a formula (210).
(378) ##STR00065## ##STR00066## ##STR00067##
(379) In the formulae (201) to (210): L.sub.201 and Ar.sub.201 represent the same as L.sub.201 and Ar.sub.201 in the formula (2); and
(380) R.sub.201 to R.sub.208 each independently represent the same as R.sub.201 to R.sub.208 in the formula (2).
(381) It is also preferable that the second compound represented by the formula (2) is a compound represented by a formula (221), a formula (222), a formula (223), a formula (224), a formula (225), a formula (226), a formula (227), a formula (228), or a formula (229) below.
(382) ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072##
(383) In the formulae (221), (222), (223), (224), (225), (226), (227), (228) and (229): R.sub.201 and R.sub.203 to R.sub.208 each independently represent the same as R.sub.201 and R.sub.203 to R.sub.208 in the formula (2);
(384) L.sub.201 and Ar.sub.201 represent the same as L.sub.201 and Ar.sub.201 in the formula (2); and
(385) L.sub.203 represents the same as L.sub.201 in the formula (2);
(386) L.sub.203 and L.sub.201 are mutually the same or different;
(387) Ar.sub.203 represents the same as Ar.sub.201 in the formula (2); and
(388) Ar.sub.203 and Ar.sub.201 are mutually the same or different.
(389) The second compound represented by the formula (2) is also preferably a compound represented by a formula (241), (242), (243), (244), (245), (246), (247), (248) or (249).
(390) ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078##
(391) In the formulae (241), (242), (243), (244), (245), (246), (247), (248) and (249): R.sub.201, R.sub.202, and R.sub.204 to R.sub.208 each independently represent the same as R.sub.201, R.sub.202, and R.sub.204 to R.sub.208 in the formula (2);
(392) L.sub.201 and Ar.sub.201 represent the same as L.sub.201 and Ar.sub.201 in the formula (2); and
(393) L.sub.203 represents the same as L.sub.201 in the formula (2);
(394) L.sub.203 and L.sub.201 are mutually the same or different;
(395) Ar.sub.203 represents the same as Ar.sub.201 in the formula (2); and
(396) Ar.sub.203 and Ar.sub.201 are mutually the same or different.
(397) In the second compound represented by the formula (2), R.sub.201 to R.sub.208 that are not represented by the formula (21) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903).
(398) L.sub.101 is a single bond or an unsubstituted arylene group having 6 to 22 ring carbon atoms, and
(399) Ar.sub.101 is a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.
(400) In the organic EL device according to the exemplary embodiment, in the second compound represented by the formula (2), R.sub.201 to R.sub.208 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903).
(401) In the organic EL device according to the exemplary embodiment, R.sub.201 to R.sub.208 in the second compound represented by the formula (2) are each preferably a hydrogen atom.
(402) In the second compound, the groups specified to be “substituted or unsubstituted” are each preferably an “unsubstituted” group.
(403) Manufacturing Method of Second Compound
(404) The second compound can be manufactured by a known method. The second compound can also be manufactured based on a known method through a known alternative reaction using a known material(s) tailored for the target compound.
(405) Specific Examples of Second Compound
(406) Specific examples of the second compound include the following compounds. It should however be noted that the invention is not limited by the specific examples of the second compound.
(407) ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127## ##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132## ##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137## ##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142## ##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147## ##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152## ##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157## ##STR00158## ##STR00159## ##STR00160## ##STR00161##
Sixth Compound and Seventh Compound
(408) The sixth compound and the seventh compound are each independently at least one compound selected from the group consisting of a compound represented by a formula (3A), a compound represented by a formula (4), a compound represented by a formula (5), a compound represented by a formula (6), a compound represented by a formula (7), a compound represented by a formula (8), a compound represented by a formula (9), and a compound represented by a formula (10).
(409) Compound Represented by Formula (3A)
(410) A compound represented by formula (3A) will be described below.
(411) ##STR00162##
(412) In the formula (3A), at least one combination of adjacent two or more of Ra.sub.301, Ra.sub.302, Ra.sub.303, Ra.sub.304, Ra.sub.305, Ra.sub.306, Ra.sub.307, Ra.sub.308, Ra.sub.39 and Ra.sub.310 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and at least one of Ra.sub.301 to Ra.sub.310 is a monovalent group represented by a formula (31A) below, Ra.sub.301 to Ra.sub.310 forming neither the monocyclic ring nor the fused ring and not being the monovalent group represented by the formula (31A) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(413) ##STR00163##
(414) In the formula (31A), Ara.sub.301 and Ara.sub.301 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(415) La.sub.301, La.sub.302, and La.sub.303 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
(416) * represents a bonding position to a pyrene ring in the formula (3A).
(417) In the sixth compound and the seventh compound, R.sub.901, R.sub.902, R.sub.903, R.sub.904, R.sub.905, R.sub.906, and R.sub.907 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(418) a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
(419) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(420) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(421) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different;
(422) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different;
(423) when a plurality of R.sub.905 are present, the plurality of R.sub.905 are mutually the same or different;
(424) when a plurality of R.sub.906 are present, the plurality of R.sub.906 are mutually the same or different; and
(425) when a plurality of R.sub.907 are present, the plurality of R.sub.907 are mutually the same or different.
(426) In the formula (3A), two of Ra.sub.301 to Ra.sub.310 are preferably groups represented by the formula (31A).
(427) In the exemplary embodiment, a compound represented by the formula (3A) is a compound represented by a formula (33A).
(428) ##STR00164##
(429) In the formula (33A): Ra.sub.311, Ra.sub.312, Ra.sub.313, Ra.sub.314, Ra.sub.315, Ra.sub.316, Ra.sub.317 and Ra.sub.318 each independently represent the same as Ra.sub.301 to Ra.sub.310 in the formula (3A) that are not the monovalent group represented by the formula (31A);
(430) La.sub.311, La.sub.312, La.sub.313, La.sub.314, La.sub.315 and La.sub.316 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
(431) Ara.sub.312, Ara.sub.313, Ara.sub.315 and Ara.sub.316 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(432) In the formula (31A), La.sub.301 is preferably a single bond, and La.sub.302 and La.sub.303 are preferably a single bond.
(433) In the exemplary embodiment, a compound represented by the formula (3A) is represented by a formula (33A) or a formula (35A) below.
(434) ##STR00165##
(435) In the formula (34A): Ra.sub.311 to Ra.sub.318 each independently represent the same as Ra.sub.301 to Ra.sub.310 in the formula (3A) that are not the monovalent group represented by the formula (31A); La.sub.312, La.sub.313, La.sub.315 and La.sub.316 each independently represent the same as La.sub.312, La.sub.313, La.sub.315 and La.sub.316 in the formula (33A); and Ara.sub.312, Ara.sub.31, Ara.sub.315 and Ara.sub.316 each independently represent the same as Ara.sub.312, Ara.sub.313, Ara.sub.315 and Ara.sub.316 in the formula (33A).
(436) ##STR00166##
(437) In the formula (35A): Ra.sub.311 to Ra.sub.318 each independently represent the same as Ra.sub.301 to Ra.sub.310 in the formula (3A) that are not the monovalent group represented by the formula (31A); and
(438) Ara.sub.312, Ara.sub.313, Ara.sub.315 and Ara.sub.316 each independently represent the same as Ara.sub.312, Ara.sub.313, Ara.sub.315 and Ara.sub.316 in the formula (33A).
(439) In the formula (31A), at least one of Ara.sub.301 or Ara.sub.302 is preferably a group represented by a formula (36A) below.
(440) In the formulae (33A) to (35A), at least one of Ara.sub.312 or Ara.sub.313 is preferably a group represented by the formula (36A).
(441) In the formulae (33A) to (35A), at least one of Ara.sub.315 or Ara.sub.316 is preferably a group represented by the formula (36A).
(442) ##STR00167##
(443) In the formula (36A): Xa.sub.3 represents an oxygen atom or a sulfur atom; at least one combination of adjacent two or more of Ra.sub.321 to Ra.sub.327 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; Ra.sub.321, Ra.sub.322, Ra.sub.323, Ra.sub.324, Ra.sub.325, Ra.sub.326 and Ra.sub.327 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(444) * represents a bonding position to La.sub.302, La.sub.303, La.sub.312, La.sub.313, La.sub.315 or La.sub.316.
(445) Xa.sub.3 is preferably an oxygen atom.
(446) At least one of Ra.sub.321 to Ra.sub.327 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(447) In the formula (31A), Ara.sub.301 is preferably a group represented by the formula (36A) and Ara.sub.302 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(448) In the formulae (33A) to (35A), Ara.sub.312 is preferably a group represented by the formula (36A) and Ara.sub.313 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(449) In the formulae (33A) to (35A), Ara.sub.315 is preferably a group represented by the formula (36A) and Ara.sub.316 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(450) In the exemplary embodiment, a compound represented by the formula (3A) is represented by a formula (37A).
(451) ##STR00168##
(452) In the formula (37A): Ra.sub.311 to Ra.sub.318 each independently represent the same as Ra.sub.301 to Ra.sub.310 in the formula (3A) that are not the monovalent group represented by the formula (31A);
(453) at least one combination of adjacent two or more of Ra.sub.321 to Ra.sub.327 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(454) at least one combination of adjacent two or more of Ra.sub.341 to Ra.sub.347 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(455) Ra.sub.321 to Ra.sub.327 and Ra.sub.341 to Ra.sub.347 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(456) Ra.sub.331 to Ra.sub.335 and Ra.sub.351 to Ra.sub.355 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(457) Specific Examples of Compound Represented by Formula (3A)
(458) Specific examples of the compound represented by the formula (3A) include compounds shown below.
(459) ##STR00169## ##STR00170## ##STR00171## ##STR00172## ##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177## ##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182## ##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187## ##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192##
Compound Represented by Formula (4)
(460) The compound represented by the formula (4) will be described below.
(461) ##STR00193##
(462) In the formula (4): Z are each independently CRa or a nitrogen atom;
(463) A1 ring and A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
(464) when a plurality of Ra are present, at least one combination of adjacent two or more of Ra are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(465) n21 and n22 are each independently 0, 1, 2, 3 or 4;
(466) when a plurality of Rb are present, at least one combination of adjacent two or more of Rb are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(467) when a plurality of Rc are present, at least one combination of adjacent two or more of Rc are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(468) Ra, Rb, and Rc not forming the monocyclic ring and not forming the fused ring are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(469) The “aromatic hydrocarbon ring” for the A1 ring and A2 ring has the same structure as the compound formed by introducing a hydrogen atom to the “aryl group” described above.
(470) Ring atoms of the “aromatic hydrocarbon ring” for the A1 ring and the A2 ring include two carbon atoms on a fused bicyclic structure at the center of the formula (4).
(471) Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include a compound formed by introducing a hydrogen atom to the “aryl group” described in the specific example group G1.
(472) The “heterocycle” for the A1 ring and A2 ring has the same structure as the compound formed by introducing a hydrogen atom to the “heterocyclic group” described above.
(473) Ring atoms of the “heterocycle” for the A1 ring and the A2 ring include two carbon atoms on a fused bicyclic structure at the center of the formula (4).
(474) Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include a compound formed by introducing a hydrogen atom to the “heterocyclic group” described in the specific example group G2.
(475) Rb is bonded to any one of carbon atoms forming the aromatic hydrocarbon ring for the A1 ring or any one of the atoms forming the heterocycle for the A1 ring.
(476) Rc is bonded to any one of carbon atoms forming the aromatic hydrocarbon ring for the A2 ring or any one of the atoms forming the heterocycle for the A2 ring.
(477) At least one of Ra, Rb, or Rc is preferably a group represented by the formula (4a) below. More preferably, at least two of Ra, Rb, and Rc are groups represented by the formula (4a).
(478) ##STR00194##
(479) In the formula (4a): L.sub.401 is preferably a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
(480) Ar.sub.401 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (4b).
(481) ##STR00195##
(482) In the formula (4b): L.sub.402 and L.sub.403 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;
(483) a combination of Ar.sub.402 and Ar.sub.403 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(484) Ar.sub.402 and Ar.sub.403 not forming the monocyclic ring and not forming the fused ring are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(485) In an exemplary embodiment, the compound represented by the formula (4) is represented by a formula (42) below.
(486) ##STR00196##
(487) In the formula (42): at least one combination of adjacent two or more of R.sub.401 to R.sub.411 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(488) R.sub.401 to R.sub.411 neither forming the monocyclic ring nor forming the fused ring each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(489) At least one of R.sub.401 to R.sub.411 is preferably a group represented by the formula (4a). More preferably, at least two of R.sub.401 to R.sub.411 are groups represented by the formula (21a).
(490) R.sub.404 and R.sub.411 are preferably groups represented by the formula (4a).
(491) In an exemplary embodiment, the compound represented by the formula (4) is a compound formed by bonding a moiety represented by a formula (4-1) or a formula (4-2) below to the A1 ring.
(492) Further, in an exemplary embodiment, the compound represented by the formula (42) is a compound formed by bonding the moiety represented by the formula (4-1) or the formula (4-2) to the ring bonded with R.sub.404 to R.sub.407.
(493) ##STR00197##
(494) In the formula (4-1), two bonds * are each independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocycle for the A1 ring in the formula (4) or bonded to one of R.sub.404 to R.sub.407 in the formula (42).
(495) In the formula (4-2), three bonds * are each independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring or the ring atom of the heterocycle for the A1 ring in the formula (4) or bonded to one of R.sub.404 to R.sub.407 in the formula (42).
(496) At least one combination of adjacent two or more of R.sub.421 to R.sub.427 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded.
(497) At least one combination of adjacent two or more of R.sub.431 to R.sub.438 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded.
(498) R.sub.421 to R.sub.427 and R.sub.431 to R.sub.438 neither forming the monocyclic ring nor forming the fused ring each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(499) In an exemplary embodiment, the compound represented by the formula (4) is a compound represented by a formula (41-3), a formula (41-4) or a formula (41-5) below.
(500) ##STR00198##
(501) In the formulae (41-3), (41-4), and (41-5):
(502) A1 ring is as defined for the formula (4);
(503) R.sub.421 to R.sub.427 each independently represent the same as R.sub.421 to R.sub.427 in the formula (4-1); and
(504) R.sub.440 to R.sub.448 each independently represent the same as R.sub.401 to R.sub.411 in the formula (42).
(505) In an exemplary embodiment, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms for the A1 ring in the formula (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring.
(506) In an exemplary embodiment, a substituted or unsubstituted heterocycle having 5 to 50 ring atoms for the A1 ring in the formula (41-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
(507) In an exemplary embodiment, the compound represented by the formula (4) or the formula (42) is a compound selected from the group consisting of compounds represented by formulae (461) to (467) below.
(508) ##STR00199## ##STR00200##
(509) In the formulae (461), (462), (463), (464), (465), (466), and (467):
(510) R.sub.421 to R.sub.427 each independently represent the same as R.sub.421 to R.sub.427 in the formula (4-1);
(511) R.sub.431 to R.sub.434 each independently represent the same as R.sub.431 to R.sub.43 in the formula (4-2);
(512) R.sub.440 to R.sub.448 and R.sub.451 to R.sub.454 each independently represent the same as R.sub.401 to R.sub.411 in the formula (42);
(513) X.sub.4 is an oxygen atom, NR.sub.801, or C(R.sub.802)(R.sub.803);
(514) R.sub.801, R.sub.802, and R.sub.803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(515) a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
(516) when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different;
(517) when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different; and
(518) when a plurality of R.sub.803 are present, the plurality of R.sub.803 are mutually the same or different.
(519) In an exemplary embodiment, in the compound represented by the formula (42), at least one combination of adjacent two or more of R.sub.401 to R.sub.411 are mutually bonded to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The compound represented by the formula (42) in the exemplary embodiment is described in detail as a compound represented by a formula (45).
(520) Compound Represented by Formula (45)
(521) The compound represented by the formula (45) will be described.
(522) ##STR00201##
(523) In the formula (45), two or more of combinations selected from the group consisting of a combination of R.sub.461 and R.sub.462, a combination of R.sub.462 and R.sub.463, a combination of R.sub.464 and R.sub.465, a combination of R.sub.465 and R.sub.466, a combination of R.sub.466 and R.sub.467, a combination of R.sub.468 and R.sub.469, a combination of R.sub.469 and R.sub.470, and a combination of R.sub.470 and R.sub.471 are mutually bonded to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
(524) However, the combination of R.sub.461 and R.sub.462 and the combination of R.sub.462 and R.sub.463, the combination of R.sub.464 and R.sub.465 and the combination of R.sub.465 and R.sub.466, the combination of R.sub.465 and R.sub.466 and the combination of R.sub.466 and R.sub.467, the combination of R.sub.468 and R.sub.469 and the combination of R.sub.469 and R.sub.470, and the combination of R.sub.469 and R.sub.470 and the combination of R.sub.470 and R.sub.471 do not form a ring at the same time.
(525) At least two rings formed by R.sub.461 to R.sub.471 are mutually the same or different.
(526) R.sub.461 to R.sub.471 neither forming the monocyclic ring nor forming the fused ring each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(527) In the formula (45), R.sub.n and R.sub.n+1 (n being an integer selected from 461, 462, 464 to 466, and 468 to 470) are mutually bonded to form a substituted or unsubstituted monocyclic ring or fused ring together with two ring-forming carbon atoms bonded with R.sub.n and R.sub.n+1. The ring is preferably formed of atoms selected from the group consisting of a carbon atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and is made of 3 to 7, more preferably 5 or 6 atoms.
(528) The number of the above cyclic structures in the compound represented by the formula (45) is, for instance, 2, 3, or 4. The two or more of the cyclic structures may be present on the same benzene ring on the basic skeleton represented by the formula (45) or may be present on different benzene rings. For instance, when three cyclic structures are present, each of the cyclic structures may be present on corresponding one of the three benzene rings of the formula (45).
(529) Examples of the above cyclic structures in the compound represented by the formula (45) include structures represented by formulae (451) to (460) below.
(530) ##STR00202##
In the formulae (451) to (457):
(531) each combination of *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent the two ring-forming carbon atoms respectively bonded with R.sub.n and R.sub.n+1;
(532) the ring-forming carbon atom bonded with R.sub.n may be any one of the two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14;
(533) X.sub.45 is C(R.sub.4512)(R.sub.4513), NR.sub.4514, an oxygen atom, or a sulfur atom;
(534) at least one combination of adjacent two or more of R.sub.4501 to R.sub.4506 and R.sub.4512 to R.sub.4513 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(535) R.sub.4501 to R.sub.4514 not forming the monocyclic ring and not forming the fused ring each independently represent the same as R.sub.461 to R.sub.471 in the formula (45).
(536) ##STR00203##
In the formulae (458) to (460):
(537) each combination of *1 and *2, and *3 and *4 represent the two ring-forming carbon atoms each bonded with R.sub.n and R.sub.n+1;
(538) the ring-forming carbon atom bonded with R.sub.n may be any one of the two ring-forming carbon atoms represented by *1 and *2, or *3 and *4;
(539) X.sub.45 is C(R.sub.4512)(R.sub.4513), NR.sub.4514, an oxygen atom, or a sulfur atom;
(540) at least one combination of adjacent two or more of R.sub.4512 to R.sub.4513 and R.sub.4515 to R.sub.4525 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(541) R.sub.4512 to R.sub.4513, R.sub.4515 to R.sub.4521 and R.sub.4522 to R.sub.4525, and R.sub.4514 not forming the monocyclic ring and not forming the fused ring each independently represent the same as R.sub.461 to R.sub.471 in the formula (45).
(542) In the formula (45), it is preferable that at least one of R.sub.462, R.sub.464, R.sub.465, R.sub.470 or R.sub.471 (preferably, at least one of R.sub.462, R.sub.465 or R.sub.470, more preferably R.sub.462) is a group not forming the cyclic structure.
(543) (i) A substituent, if present, of the cyclic structure formed by R.sub.n and R.sub.n+1 of the formula (45),
(544) (ii) R.sub.461 to R.sub.471 not forming the cyclic structure in the formula (45), and
(545) (iii) R.sub.4501 to R.sub.4514, R.sub.4515 to R.sub.4525 in the formulae (451) to (460) are preferably each independently any one of group selected from the group consisting of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R.sub.906)(R.sub.907), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or groups represented by formulae (461) to (464).
(546) ##STR00204##
(547) In the formulae (461) to (464): Rd each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(548) X.sub.46 represents C(R.sub.801)(R.sub.802), NR.sub.803, an oxygen atom or a sulfur atom;
(549) R.sub.801, R.sub.802, and R.sub.803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(550) a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
(551) when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different;
(552) when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different;
(553) when a plurality of R.sub.803 are present, the plurality of R.sub.803 are mutually the same or different;
(554) p1 is 5;
(555) p2 is 4;
(556) p3 is 3;
(557) p4 is 7; and
(558) in the formulae (461) to (464), * each independently represents a bonding position to a cyclic structure.
(559) In the sixth and seventh compounds, R.sub.901 to R.sub.907 represent the same as R.sub.901 to R.sub.907 as described above.
(560) In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-1) to (45-6) below.
(561) ##STR00205## ##STR00206##
(562) In the formulae (45-1) to (45-6):
(563) rings d to i are each dependently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; and
(564) R.sub.461 to R.sub.471 each independently represent the same as R.sub.461 to R.sub.471 in the formula (45).
(565) In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-7) to (45-12) below.
(566) ##STR00207## ##STR00208##
(567) In the formulae (45-7) to (45-12):
(568) rings d to f, k and j are each dependently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; and
(569) R.sub.461 to R.sub.471 each independently represent the same as R.sub.461 to R.sub.471 in the formula (45).
(570) In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-13) to (45-21) below.
(571) ##STR00209## ##STR00210## ##STR00211##
(572) In the formulae (45-13) to (45-21):
(573) rings d to k are each dependently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring; and
(574) R.sub.461 to R.sub.471 each independently represent the same as R.sub.461 to R.sub.471 in the formula (45).
(575) When the ring g or the ring h further has a substituent, examples of the substituent include a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a group represented by the formula (461), a group represented by the formula (463), and a group represented by the formula (464).
(576) In an exemplary embodiment, the compound represented by the formula (45) is represented by one of formulae (45-22) to (45-25) below.
(577) ##STR00212## ##STR00213##
(578) In the formulae (45-22) to (45-25):
(579) X.sub.46 and X.sub.47 are each independently C(R.sub.801)(R.sub.802), NR.sub.803, an oxygen atom or a sulfur atom; and
(580) R.sub.461 to R.sub.471 and R.sub.481 to R.sub.488 respectively represent the same as R.sub.461 to R.sub.471 of the formula (45).
(581) R.sub.801, R.sub.802, and R.sub.803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(582) a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
(583) when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different;
(584) when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different; and
(585) when a plurality of R.sub.803 are present, the plurality of R.sub.803 are mutually the same or different.
(586) In an exemplary embodiment, the compound represented by the formula (45) is represented by a formula (45-26) below.
(587) ##STR00214##
(588) In the formula (45-26): X.sub.46 represents C(R.sub.801)(R.sub.802), NR.sub.803, an oxygen atom or a sulfur atom;
(589) R.sub.463, R.sub.464, R.sub.467, R.sub.468, R.sub.471, and R.sub.481 to R.sub.492 each independently represent the same as R.sub.461 to R.sub.471 in the formula (45);
(590) R.sub.801, R.sub.802, and R.sub.803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(591) a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
(592) when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different;
(593) when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different; and
(594) when a plurality of R.sub.803 are present, the plurality of R.sub.803 are mutually the same or different.
(595) Specific Examples of Compound Represented by Formula (4)
(596) Specific examples of the compound represented by the formula (4) include compounds shown below. In the specific examples below, Ph represents a phenyl group, and D represents a deuterium atom.
(597) ##STR00215## ##STR00216## ##STR00217## ##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222## ##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227## ##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232## ##STR00233## ##STR00234## ##STR00235## ##STR00236## ##STR00237## ##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242## ##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247##
Compound Represented by Formula (5)
(598) The compound represented by the formula (5) will be described below. The compound represented by the formula (5) corresponds to the compound represented by the above-described formula (41-3).
(599) ##STR00248##
(600) In the formula (5), at least one combination of adjacent two or more of R.sub.501 to R.sub.507 and R.sub.511 to R.sub.517 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(601) R.sub.501 to R.sub.507 and R.sub.511 to R.sub.517 neither forming the monocyclic ring nor forming the fused ring each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(602) R.sub.521 and R.sub.522 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(603) “A combination of adjacent two or more of R.sub.501 to R.sub.507 and R.sub.511 to R.sub.517” refers to, for instance, a combination of R.sub.501 and R.sub.502, a combination of R.sub.502 and R.sub.503, a combination of R.sub.503 and R.sub.504, a combination of R.sub.505 and R.sub.506, a combination of R.sub.506 and R.sub.507, and a combination of R.sub.501, R.sub.502, and R.sub.503.
(604) In an exemplary embodiment, at least one, preferably two of R.sub.501 to R.sub.507 and R.sub.511 to R.sub.517 are groups represented by —N(R.sub.906)(R.sub.907).
(605) In an exemplary embodiment, R.sub.501 to R.sub.507 and R.sub.511 to R.sub.517 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(606) In an exemplary embodiment, the compound represented by the formula (5) is a compound represented by a formula (52).
(607) ##STR00249##
(608) In the formula (52), at least one combination of adjacent two or more of R.sub.531 to R.sub.534 and R.sub.541 to R.sub.544 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(609) R.sub.531 to R.sub.534, R.sub.541 to R.sub.544, R.sub.551 and R.sub.552 neither forming the monocyclic ring nor forming the fused ring each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(610) R.sub.561 to R.sub.564 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(611) In an exemplary embodiment, the compound represented by the formula (5) is a compound represented by a formula (53).
(612) ##STR00250##
(613) In the formula (53), R.sub.551, R.sub.552 and R.sub.561 to R.sub.564 each independently represent the same as R.sub.551, R.sub.552 and R.sub.561 to R.sub.564 in the formula (52).
(614) In an exemplary embodiment, R.sub.561 to R.sub.564 in the formulae (52) and (53) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).
(615) In an exemplary embodiment, R.sub.521 and R.sub.522 in the formula (5) and R.sub.551 and R.sub.552 in the formulae (52) and (53) are hydrogen atoms.
(616) In an exemplary embodiment, the substituent for “substituted or unsubstituted” in the formulae (5), (52) and (53) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(617) Specific Examples of Compound Represented by Formula (5)
(618) Specific examples of the compound represented by the formula (5) include compounds shown below.
(619) ##STR00251## ##STR00252## ##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257## ##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262## ##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267## ##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272## ##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277## ##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282## ##STR00283## ##STR00284## ##STR00285## ##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290## ##STR00291## ##STR00292## ##STR00293## ##STR00294## ##STR00295## ##STR00296## ##STR00297## ##STR00298## ##STR00299## ##STR00300## ##STR00301## ##STR00302## ##STR00303## ##STR00304## ##STR00305## ##STR00306## ##STR00307## ##STR00308## ##STR00309## ##STR00310## ##STR00311## ##STR00312## ##STR00313## ##STR00314## ##STR00315## ##STR00316## ##STR00317## ##STR00318## ##STR00319## ##STR00320## ##STR00321## ##STR00322## ##STR00323## ##STR00324##
Compound Represented by Formula (6)
(620) The compound represented by the formula (6) will be described below.
(621) ##STR00325##
(622) In the formula (6): a ring, b ring and c ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
(623) R.sub.601 and R.sub.602 are each independently bonded with the a ring, b ring, or a c ring to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle; and
(624) R.sub.601 and R.sub.602 not forming the substituted or unsubstituted heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(625) The a ring, b ring and c ring are each a ring (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms) fused with the fused bicyclic moiety formed of a boron atom and two nitrogen atoms at the center of the formula (6).
(626) The “aromatic hydrocarbon ring” for the a, b, and c rings has the same structure as the compound formed by introducing a hydrogen atom to the “aryl group” described above.
(627) Ring atoms of the “aromatic hydrocarbon ring” for the a ring include three carbon atoms on the fused bicyclic structure at the center of the formula (6).
(628) Ring atoms of the “aromatic hydrocarbon ring” for the b ring and the c ring include two carbon atoms on a fused bicyclic structure at the center of the formula (6).
(629) Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include a compound formed by introducing a hydrogen atom to the “aryl group” described in the specific example group G1.
(630) The “heterocycle” for the a, b, and c rings has the same structure as the compound formed by introducing a hydrogen atom to the “heterocyclic group” described above.
(631) Ring atoms of the “heterocycle” for the a ring include three carbon atoms on the fused bicyclic structure at the center of the formula (6). Ring atoms of the “heterocycle” for the b ring and the c ring include two carbon atoms on a fused bicyclic structure at the center of the formula (6). Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include a compound formed by introducing a hydrogen atom to the “heterocyclic group” described in the specific example group G2.
(632) R.sub.601 and R.sub.602 are optionally each independently bonded with the a ring, b ring, or c ring to form a substituted or unsubstituted heterocycle. The “heterocycle” in this arrangement includes the nitrogen atom on the fused bicyclic structure at the center of the formula (6). The heterocycle in the above arrangement optionally include a hetero atom other than the nitrogen atom. R.sub.601 and R.sub.602 bonded with the a ring, b ring, or c ring specifically means that atoms forming R.sub.601 and R.sub.602 are bonded with atoms forming the a ring, b ring, or c ring. For instance, R.sub.601 may be optionally bonded to the a ring to form a bicyclic (or tri-or-more cyclic) fused nitrogen-containing heterocycle, in which the ring including R.sub.601 and the a ring are fused. Specific examples of the nitrogen-containing heterocycle include a compound corresponding to the nitrogen-containing bi(or-more)cyclic heterocyclic group in the specific example group G2.
(633) The same applies to R.sub.601 bonded with the b ring, R.sub.602 bonded with the a ring, and R.sub.602 bonded with the c ring.
(634) In an exemplary embodiment, the a ring, b ring and c ring in the formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
(635) In an exemplary embodiment, the a ring, b ring and c ring in the formula (6) are each independently a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.
(636) In an exemplary embodiment, R.sub.601 and R.sub.602 in the formula (6) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(637) In an exemplary embodiment, the compound represented by the formula (6) is represented by a formula (62) below.
(638) ##STR00326##
(639) In the formula (62): R.sub.601A is bonded with at least one of R.sub.611 or R.sub.621 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(640) R.sub.602A is bonded with at least one of R.sub.613 or R.sub.614A to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(641) R.sub.601A and R.sub.602A not forming the substituted or unsubstituted heterocycle are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(642) at least one combination of adjacent two or more of R.sub.611 to R.sub.621 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(643) R.sub.611 to R.sub.621 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(644) R.sub.601A and R.sub.602A in the formula (62) are groups corresponding to R.sub.601 and R.sub.602 in the formula (6), respectively.
(645) For instance, R.sub.601A and R.sub.611 are optionally bonded with each other to form a bicyclic (or tri-or-more cyclic) nitrogen-containing heterocycle, in which the ring including R.sub.601A and R.sub.611 and a benzene ring corresponding to the a ring are fused. Specific examples of the nitrogen-containing heterocycle include a compound corresponding to the nitrogen-containing bi(or-more)cyclic heterocyclic group in the specific example group G2. The same applies to R.sub.601A bonded with R.sub.621, R.sub.602A bonded with R.sub.613, and R.sub.602A bonded with R.sub.614.
(646) At least one combination of adjacent two or more of R.sub.611 to R.sub.621 may be mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted monocyclic ring, For instance, R.sub.611 and R.sub.612 are mutually bonded to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring, benzothiophene ring or the like is bonded to the six-membered ring bonded with R.sub.611 and R.sub.612, the resultant fused ring forming a naphthalene ring, carbazole ring, indole ring, dibenzofuran ring, or dibenzothiophene ring, respectively.
(647) In an exemplary embodiment, R.sub.611 to R.sub.621 not contributing to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(648) In an exemplary embodiment, R.sub.611 to R.sub.621 not contributing to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(649) In an exemplary embodiment, R.sub.611 to R.sub.621 not contributing to ring formation are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
(650) In an exemplary embodiment, R.sub.611 to R.sub.621 not contributing to ring formation are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and
(651) At least one of R.sub.611 to R.sub.621 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
(652) In an exemplary embodiment, the compound represented by the formula (62) is represented by a formula (63) below.
(653) ##STR00327##
(654) In the formula (63): R.sub.631 is bonded with R.sub.646 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(655) R.sub.633 is bonded with R.sub.647 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(656) R.sub.634 is bonded with R.sub.651 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(657) R.sub.641 is bonded with R.sub.642 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(658) at least one combination of adjacent two or more of R.sub.631 to R.sub.651 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(659) R.sub.631 to R.sub.651 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(660) R.sub.631 are optionally mutually bonded with R.sub.646 to form a substituted or unsubstituted heterocycle. For instance, R.sub.631 and R.sub.646 are optionally bonded with each other to form a tri-or-more cyclic nitrogen-containing heterocycle, in which a benzene ring bonded with R.sub.646, a ring including a nitrogen atom, and a benzene ring corresponding to the a ring are fused. Specific examples of the nitrogen-containing heterocycle include a compound corresponding to the nitrogen-containing tri(-or-more)cyclic heterocyclic group in the specific example group G2. The same applies to R.sub.633 bonded with R.sub.647, R.sub.634 bonded with R.sub.651, and R.sub.641 bonded with R.sub.642.
(661) In an exemplary embodiment, R.sub.631 to R.sub.651, which do not contribute to ring formation, are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(662) In an exemplary embodiment, R.sub.631 to R.sub.651, which do not contribute to ring formation, are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(663) In an exemplary embodiment, R.sub.631 to R.sub.651, which do not contribute to ring formation, are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
(664) In an exemplary embodiment, R.sub.631 to R.sub.651, which do not contribute to ring formation, are each independently a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R.sub.631 to R.sub.651 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
(665) In an exemplary embodiment, the compound represented by the formula (63) is represented by a formula (63A) below.
(666) ##STR00328##
(667) In the formula (63A): R.sub.661 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and
(668) R.sub.662 to R.sub.665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(669) In an exemplary embodiment, R.sub.661 to R.sub.665, which do not contribute to ring formation, are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(670) In an exemplary embodiment, R.sub.661 to R.sub.665 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
(671) In an exemplary embodiment, the compound represented by the formula (63) is represented by a formula (63B) below.
(672) ##STR00329##
(673) In the formula (63B): R.sub.671 and R.sub.672 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R.sub.906)(R.sub.907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and
(674) R.sub.673 to R.sub.675 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R.sub.906)(R.sub.907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(675) In an exemplary embodiment, the compound represented by the formula (63) is represented by a formula (63B′) below.
(676) ##STR00330##
(677) In the formula (63B′), R.sub.672 to R.sub.675 each independently represent the same as R.sub.672 to R.sub.675 in the formula (63B).
(678) In an exemplary embodiment, at least one of R.sub.671 to R.sub.675 is: a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R.sub.906)(R.sub.907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(679) In an exemplary embodiment: R.sub.672 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a group represented by —N(R.sub.906)(R.sub.907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and
(680) R.sub.671, and R.sub.673 to R.sub.675 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a group represented by —N(R.sub.906)(R.sub.907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(681) In an exemplary embodiment, the compound represented by the formula (63) is represented by a formula (63C) below.
(682) ##STR00331##
(683) In the formula (63C): R.sub.681 and R.sub.682 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; and
(684) R.sub.683 to R.sub.686 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(685) In an exemplary embodiment, the compound represented by the formula (63) is represented by a formula (63C′) below.
(686) ##STR00332##
(687) In the formula (63C′), R.sub.683 to R.sub.686 each independently represent the same as R.sub.683 to R.sub.686 in the formula (63C).
(688) In an exemplary embodiment, R.sub.681 to R.sub.686, which do not contribute to ring formation, are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(689) In an exemplary embodiment, R.sub.681 to R.sub.686 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(690) The compound represented by the formula (6) is producible by initially bonding the a ring, b ring and c ring with linking groups (a group including N—R.sub.601 and a group including N—R.sub.602) to form an intermediate (first reaction), and bonding the a ring, b ring and c ring with a linking group (a group including a boron atom) to form a final product (second reaction). In the first reaction, an amination reaction (e.g. Buchwald-Hartwig reaction) is applicable. In the second reaction, Tandem Hetero-Friedel-Crafts Reactions or the like is applicable.
(691) Specific Examples of Compound Represented by Formula (6)
(692) Specific examples of the compound represented by the formula (6) are shown below. It should however be noted that these specific examples are merely exemplary and do not limit the compound represented by the formula (6).
(693) ##STR00333## ##STR00334## ##STR00335## ##STR00336## ##STR00337## ##STR00338## ##STR00339## ##STR00340## ##STR00341## ##STR00342## ##STR00343## ##STR00344## ##STR00345## ##STR00346## ##STR00347## ##STR00348## ##STR00349## ##STR00350## ##STR00351## ##STR00352## ##STR00353## ##STR00354## ##STR00355## ##STR00356## ##STR00357## ##STR00358## ##STR00359## ##STR00360## ##STR00361## ##STR00362## ##STR00363## ##STR00364## ##STR00365## ##STR00366## ##STR00367##
Compound Represented by Formula (7)
(694) The compound represented by the formula (7) will be described below.
(695) ##STR00368##
(696) In the formula (7): r ring is a ring represented by the formula (72) or the formula (73), the r ring being fused with at any position(s) of respective adjacent rings;
(697) q ring and s ring are each independently a ring represented by the formula (74) and fused with any position(s) of respective adjacent rings;
(698) p ring and t ring are each independently a moiety represented by the formula (75) or the formula (76) and fused with any position(s) of respective adjacent rings;
(699) X.sub.7 is an oxygen atom, a sulfur atom, or NR.sub.702;
(700) when a plurality of R.sub.701 are present, adjacent ones of the plurality of R.sub.701 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(701) R.sub.701 and R.sub.702 not forming the monocyclic ring and not forming the fused ring are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(702) Ar.sub.701 and Ar.sub.702 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(703) L.sub.701 is a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(704) m1 is 0, 1, or 2;
(705) m2 is 0, 1, 2, 3, or 4;
(706) m3 is each independently 0, 1, 2, 3 or 3;
(707) m4 is each independently 0, 1, 2, 3, 4, or 5;
(708) when a plurality of R.sub.701 are present, the plurality of R.sub.701 are mutually the same or different;
(709) when a plurality of X.sub.7 are present, the plurality of X.sub.7 are mutually the same or different;
(710) when a plurality of R.sub.702 are present, the plurality of R.sub.702 are mutually the same or different;
(711) when a plurality of Ar.sub.701 are present, the plurality of Ar.sub.701 are mutually the same or different;
(712) when a plurality of Ar.sub.702 are present, the plurality of Ar.sub.702 are mutually the same or different; and
(713) when a plurality of L.sub.701 are present, the plurality of L.sub.701 are mutually the same or different.
(714) In the formula (7), each of the p ring, q ring, r ring, s ring, and t ring is fused with an adjacent ring(s) sharing two carbon atoms. The fused position and orientation are not limited but may be defined as required.
(715) In an exemplary embodiment, in the formula (72) or the formula (73) representing the r ring, m1=0 or m2=0.
(716) In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-1) to (71-6) below.
(717) ##STR00369##
(718) In the formulae (71-1) to (71-6), R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, m1, and m3 respectively represent the same as R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, m1, and m3 in the formula (7).
(719) In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-11) to (71-13) below.
(720) ##STR00370##
(721) In the formulae (71-11) to (71-13), R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, m1, m3 and m4 respectively represent the same as R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, m1, m3 and m4 in the formula (7).
(722) In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-21) to (71-25) below.
(723) ##STR00371##
(724) In the formulae (71-21) to (71-25), R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, m1, and m4 respectively represent the same as R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, m1, and m4 in the formula (7).
(725) In an exemplary embodiment, the compound represented by the formula (7) is represented by any one of formulae (71-31) to (71-33) below.
(726) ##STR00372##
(727) In the formulae (71-31) to (71-33), R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, and m2 to m4 respectively represent the same as R.sub.701, X.sub.7, Ar.sub.701, Ar.sub.702, L.sub.701, and m2 to m4 in the formula (7).
(728) In an exemplary embodiment, Ar.sub.701 and Ar.sub.702 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(729) In an exemplary embodiment, one of Ar.sub.701 and Ar.sub.702 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other of Ar.sub.701 and Ar.sub.702 is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(730) Specific Examples of Compound Represented by Formula (7)
(731) Specific examples of the compound represented by the formula (7) include compounds shown below.
(732) ##STR00373## ##STR00374## ##STR00375## ##STR00376## ##STR00377## ##STR00378## ##STR00379## ##STR00380## ##STR00381## ##STR00382## ##STR00383## ##STR00384## ##STR00385## ##STR00386## ##STR00387## ##STR00388## ##STR00389## ##STR00390## ##STR00391##
Compound Represented by Formula (8)
(733) The compound represented by the formula (8) will be described below.
(734) ##STR00392##
(735) In the formula (8): at least one combination of R.sub.801 and R.sub.802, R.sub.802 and R.sub.803, or R.sub.803 and R.sub.804 are mutually bonded to form a divalent group represented by a formula (82) below, or not mutually bonded; and
(736) at least one combination of R.sub.805 and R.sub.806, R.sub.806 and R.sub.807, or R.sub.807 and R.sub.808 are mutually bonded to form a divalent group represented by a formula (83) below, or not mutually bonded.
(737) ##STR00393##
(738) At least one of R.sub.801 to R.sub.804 or R.sub.811 to R.sub.814 not forming the divalent group represented by the formula (82) is a monovalent group represented by a formula (84) below;
(739) At least one of R.sub.805 to R.sub.808 or R.sub.821 to R.sub.824 not forming the divalent group represented by the formula (83) is a monovalent group represented by a formula (84) below;
(740) X.sub.8 is CR.sub.81R.sub.82, an oxygen atom, a sulfur atom, or NR.sub.809;
(741) a pair of R.sub.81 and R.sub.82 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(742) R.sub.801 to R.sub.808 not forming the divalent groups represented by the formulae (82) and (83) and not being the monovalent group represented by the formula (84), R.sub.811 to R.sub.814 and R.sub.821 to R.sub.824 not being the monovalent group represented by the formula (84), R.sub.81 and R.sub.82 not forming the substituted or unsubstituted monocyclic ring and not forming the substituted or unsubstituted fused ring, and R.sub.809 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(743) ##STR00394##
(744) In the formula (84): Ar.sub.801 and Ar.sub.802 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(745) L.sub.801 to L.sub.803 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding two, three or four groups selected from the group consisting of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
(746) * in the formulae (84) represents a bonding position to the cyclic structure represented by the formula (8) or a bonding position to the group represented by the formula (82) or (83).
(747) It is also preferable that at least one combination of R.sub.801 and R.sub.802, R.sub.802 and R.sub.803, or R.sub.803 and R.sub.804 are mutually bonded, and R.sub.805 and R.sub.806, R.sub.806 and R.sub.807, and R.sub.807 and R.sub.808 are not mutually bonded.
(748) It is also preferable that R.sub.801 and R.sub.802, R.sub.802 and R.sub.803, and R.sub.803 and R.sub.804 are not mutually bonded, and at least one combination of R.sub.805 and R.sub.806, R.sub.806 and R.sub.807, or R.sub.807 and R.sub.808 are mutually bonded.
(749) It is also preferable that at least one combination of R.sub.801 and R.sub.802, R.sub.802 and R.sub.803, or R.sub.803 and R.sub.804 are mutually bonded to form a divalent group represented by the formula (82), and at least one combination of R.sub.805 and R.sub.806, R.sub.806 and R.sub.807, or R.sub.807 and R.sub.808 are mutually bonded to form a divalent group represented by the formula (83).
(750) In the formula (8), the positions for the divalent group represented by the formula (82) and the divalent group represented by the formula (83) to be formed are not specifically limited but the divalent groups may be formed at any possible positions on R.sub.801 to R.sub.808.
(751) In an exemplary embodiment, the compound represented by the formula (8) is represented by any one of formulae (81A-1) to (81A-3) below.
(752) ##STR00395##
(753) In the formulae (81A-1) to (81A-3):
(754) X.sub.8 represents the same as X.sub.8 in the formula (8);
(755) at least one of R.sub.803, R.sub.804, or R.sub.811 to R.sub.814 in the formula (81A-1) is the monovalent group represented by the formula (84);
(756) at least one of R.sub.801, R.sub.804, or R.sub.811 to R.sub.814 in the formula (81A-2) is the monovalent group represented by the formula (84);
(757) at least one of R.sub.801, R.sub.802, or R.sub.811 to R.sub.814 in the formula (81A-3) is the monovalent group represented by the formula (84);
(758) at least one of R.sub.805 to R.sub.808 in the formulae (81A-1) to (81A-3) is the monovalent group represented by the formula (84); and
(759) R.sub.801 to R.sub.808 and R.sub.811 to R.sub.814 not being the monovalent group represented by the formula (84) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(760) In an exemplary embodiment, the compound represented by the formula (8) is represented by any one of formulae (81-1) to (81-6) below.
(761) ##STR00396##
(762) In the formulae (81-1) to (81-6):
(763) X.sub.8 represents the same as X.sub.8 in the formula (8);
(764) at least two of R.sub.801 to R.sub.824 are each a monovalent group represented by the formula (84); and
(765) R.sub.801 to R.sub.824 that are not the monovalent group represented by the formula (84) are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(766) In an exemplary embodiment, the compound represented by the formula (8) is represented by any one of formulae (81-7) to (81-18) below.
(767) ##STR00397## ##STR00398##
(768) In the formulae (81-7) to (81-18):
(769) X.sub.8 represents the same as X.sub.8 in the formula (8);
(770) * is a single bond to be bonded with the monovalent group represented by the formula (84); and
(771) R.sub.801 to R.sub.824 each independently represent the same as R.sub.801 to R.sub.824 in the formulae (81-1) to (81-6) that are not the monovalent group represented by the formula (84).
(772) R.sub.801 to R.sub.808 not forming the divalent group represented by the formula (82) or (83) and not being the monovalent group represented by the formula (84), and R.sub.811 to R.sub.814 and R.sub.821 to R.sub.824 not being the monovalent group represented by the formula (84) are preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(773) The monovalent group represented by the formula (84) is preferably represented by a formula (85) or (86) below.
(774) ##STR00399##
(775) In the formula (85): R.sub.831 to R.sub.840 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(776) * in the formula (85) represents the same as * in the formula (84).
(777) ##STR00400##
(778) In the formula (86): Ar.sub.801, L.sub.801, and L.sub.803 represent the same as Ar.sub.801, L.sub.801, and L.sub.803 in the formula (84); and
(779) HAr.sub.801 is a moiety represented by a formula (87) below.
(780) ##STR00401##
(781) In the formula (87):
(782) X.sub.81 represents an oxygen atom or a sulfur atom;
(783) one of R.sub.841 to R.sub.848 is a single bond with L.sub.803; and
(784) R.sub.841 to R.sub.848 not being the single bond are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(785) Specific Examples of Compound Represented by Formula (8)
(786) Specific examples of the compound represented by the formula (8) include compounds shown below as well as the compounds disclosed in WO 2014/104144.
(787) ##STR00402## ##STR00403## ##STR00404## ##STR00405## ##STR00406## ##STR00407## ##STR00408## ##STR00409## ##STR00410## ##STR00411## ##STR00412## ##STR00413## ##STR00414## ##STR00415## ##STR00416## ##STR00417## ##STR00418## ##STR00419##
Compound Represented by Formula (9)
(788) The compound represented by the formula (9) will be described below.
(789) ##STR00420##
(790) In the formula (9): A.sub.91 ring and A.sub.92 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms; and
(791) at least one of A.sub.91 ring or A.sub.92 ring is bonded with * in a moiety represented by a formula (92) below.
(792) ##STR00421##
(793) In the formula (92): A.sub.93 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
(794) X.sub.9 is NR.sub.93, C(R.sub.94)(R.sub.95), Si(R.sub.96)(R.sub.97), Ge(R.sub.98)(R.sub.99), an oxygen atom, a sulfur atom, or a selenium atom;
(795) R.sub.91 and R.sub.92 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(796) R.sub.91 and R.sub.92, and R.sub.93 to R.sub.99 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(797) At least one ring selected from the group consisting of A.sub.91 ring and A.sub.92 ring is bonded to a bond * of the moiety represented by the formula (92). In other words, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the A.sub.91 ring in an exemplary embodiment are bonded to the bonds * in the moiety represented by the formula (92). Further, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the A.sub.92 ring in an exemplary embodiment are bonded to the bonds * in the moiety represented by the formula (92).
(798) In an exemplary embodiment, the group represented by a formula (93) below is bonded to one or both of the A.sub.91 ring and A.sub.92 ring.
(799) ##STR00422##
(800) In the formula (93): Ar.sub.91 and Ar.sub.92 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; L.sub.91 to L.sub.93 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a divalent linking group formed by bonding two, three or four groups selected from the group consisting of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms; and
(801) * in the formula (93) represents a bonding position to one of A.sub.91 ring and A.sub.92 ring.
(802) In an exemplary embodiment, in addition to the A.sub.91 ring, the ring-forming carbon atoms of the aromatic hydrocarbon ring or the ring atoms of the heterocycle of the A.sub.92 ring are bonded to * in the moiety represented by the formula (92). In this case, the moieties represented by the formula (92) are mutually the same or different.
(803) In an exemplary embodiment, R.sub.91 and R.sub.92 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(804) In an exemplary embodiment, R.sub.91 and R.sub.92 are mutually bonded to form a fluorene structure.
(805) In an exemplary embodiment, the rings A.sub.91 and A.sub.92 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, example of which is a substituted or unsubstituted benzene ring.
(806) In an exemplary embodiment, the ring A.sub.93 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, example of which is a substituted or unsubstituted benzene ring.
(807) In an exemplary embodiment, X.sub.9 is an oxygen atom or a sulfur atom.
(808) Specific Examples of Compound Represented by Formula (9)
(809) Specific examples of the compound represented by the formula (9) include compounds shown below.
(810) ##STR00423## ##STR00424## ##STR00425## ##STR00426## ##STR00427## ##STR00428## ##STR00429## ##STR00430## ##STR00431## ##STR00432## ##STR00433##
Compound Represented by Formula (10)
(811) The compound represented by the formula (10) will be described below.
(812) ##STR00434##
(813) In the formula (10):
(814) Ax.sub.1 ring is a ring represented by the formula (10a) and fused with any positions of adjacent rings;
(815) Ax.sub.2 ring is a ring represented by the formula (10b) and fused with any positions of adjacent rings;
(816) Two * in the formula (10b) are bonded to any position of Ax.sub.3 ring;
(817) X.sub.A and X.sub.B are each independently C(R.sub.1003)(R.sub.1004), Si(R.sub.1005)(R.sub.1006), an oxygen atom or a sulfur atom;
(818) Ax.sub.3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms;
(819) Ar.sub.1001 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(820) R.sub.1001 to R.sub.1006 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(821) mx1 is 3, mx2 is 2;
(822) a plurality of R.sub.1001 are mutually the same or different;
(823) a plurality of R.sub.1002 are mutually the same or different;
(824) ax is 0, 1, or 2;
(825) when ax is 0 or 1, the structures enclosed by brackets indicated by “3-ax” are mutually the same or different; and
(826) when ax is 2, a plurality of Ar.sub.1001 are mutually the same or different.
(827) In an exemplary embodiment, Ar.sub.1001 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(828) In an exemplary embodiment, Ax.sub.3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, example of which is a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
(829) In an exemplary embodiment, R.sub.1003 and R.sub.1004 are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
(830) In an exemplary embodiment, ax is 1.
(831) Specific Examples of Compound Represented by Formula (10)
(832) Specific examples of the compound represented by the formula (10) include compounds shown below.
(833) ##STR00435## ##STR00436## ##STR00437##
(834) In an exemplary embodiment, the emitting layer contains, as the sixth compound and the seventh compound, at least one compound selected from the group consisting of the compound represented by the formula (4), the compound represented by the formula (5), the compound represented by the formula (7), the compound represented by the formula (8) below, the compound represented by the formula (9), and a compound represented by a formula (63a) below.
(835) ##STR00438##
(836) In the formula (63A): R.sub.631 is bonded with R.sub.646 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(837) R.sub.633 is bonded with R.sub.647 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(838) R.sub.634 is bonded with R.sub.651 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(839) R.sub.641 is bonded with R.sub.642 to form a substituted or unsubstituted heterocycle or to form no substituted or unsubstituted heterocycle;
(840) at least one combination of adjacent two or more of R.sub.631 to R.sub.651 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(841) R.sub.631 to R.sub.651 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(842) at least one of R.sub.631 to R.sub.651 not forming the substituted or unsubstituted heterocycle, not forming the monocyclic ring and not forming the fused ring are a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(843) In an exemplary embodiment, the compound represented by the formula (4) is the compound represented by the formula (41-3), the formula (41-4) or the formula (41-5), the A1 ring in the formula (41-5) being a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms, or a substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms.
(844) In an exemplary embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formulae (41-3), (41-4) and (41-5) is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring; and
(845) the substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
(846) In an exemplary embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formula (41-3), (41-4) or (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring; and
(847) the substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
(848) In an exemplary embodiment, the compound represented by the formula (4) is selected from the group consisting of a compound represented by a formula (461) below, a compound represented by a formula (462) below, a compound represented by a formula (463) below, a compound represented by a formula (464) below, a compound represented by a formula (465) below, a compound represented by a formula (466) below, and a compound represented by a formula (467) below.
(849) ##STR00439## ##STR00440##
(850) In the formulae (461) to (467): at least one combination of adjacent two or more of moieties selected from R.sub.421 to R.sub.427, R.sub.431 to R.sub.436, R.sub.440 to R.sub.448, and R.sub.451 to R.sub.454 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(851) R.sub.437, R.sub.438, and R.sub.421 to R.sub.427, R.sub.431 to R.sub.436, R.sub.440 to R.sub.448, and R.sub.451 to R.sub.454 not forming the monocyclic ring and not forming the fused ring are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a group represented by —N(R.sub.906)(R.sub.907), a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(852) X.sub.4 is an oxygen atom, NR.sub.801, or C(R.sub.802)(R.sub.803);
(853) R.sub.801, R.sub.802, and R.sub.803 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(854) a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
(855) when a plurality of R.sub.801 are present, the plurality of R.sub.801 are mutually the same or different;
(856) when a plurality of R.sub.802 are present, the plurality of R.sub.802 are mutually the same or different; and
(857) when a plurality of R.sub.803 are present, the plurality of R.sub.803 are mutually the same or different.
(858) In an exemplary embodiment, R.sub.421 to R.sub.427 and R.sub.440 to R.sub.445 are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(859) In an exemplary embodiment, R.sub.421 to R.sub.427 and R.sub.440 to R.sub.447 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
(860) In an exemplary embodiment, the compound represented by the formula (41-3) is represented by a formula (41-3-1) below.
(861) ##STR00441##
(862) In the formula (41-3-1), R.sub.423, R.sub.425, R.sub.426, R.sub.442, R.sub.444 and R.sub.445 each independently represent the same as R.sub.423, R.sub.425, R.sub.426, R.sub.442, R.sub.444 and R.sub.445 in the formula (41-3).
(863) In an exemplary embodiment, the compound represented by the formula (41-3) is represented by a formula (41-3-2) below.
(864) ##STR00442##
(865) In the formula (41-3-2), R.sub.421 to R.sub.427 and R.sub.440 to R.sub.448 each independently represent the same as R.sub.421 to R.sub.427 and R.sub.440 to R.sub.448 in the formula (41-3); and
(866) at least one of R.sub.421 to R.sub.427 or R.sub.440 to R.sub.446 is a group represented by —N(R.sub.906)(R.sub.907).
(867) In an exemplary embodiment, two of R.sub.421 to R.sub.427 and R.sub.440 to R.sub.446 in the formula (41-3-2) are groups represented by —N(R.sub.906)(R.sub.907).
(868) In an exemplary embodiment, the compound represented by the formula (41-3-2) is represented by a formula (41-3-3) below.
(869) ##STR00443##
(870) In the formula (41-3-3), R.sub.421 to R.sub.424, R.sub.440 to R.sub.443, R.sub.447, and R.sub.448 each independently represent the same as R.sub.421 to R.sub.424, R.sub.440 to R.sub.443, R.sub.447, and R.sub.448 in the formula (41-3); and
(871) R.sub.A, R.sub.B, R.sub.C, and R.sub.D are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
(872) In an exemplary embodiment, the compound represented by the formula (41-3-3) is represented by a formula (41-3-4) below.
(873) ##STR00444##
(874) In the formula (41-3-4), R.sub.447, R.sub.448, R.sub.A, R.sub.B, R.sub.C and R.sub.D each independently represent the same as R.sub.447, R.sub.448, R.sub.A, R.sub.B, R.sub.C and R.sub.D in the formula (41-3-3).
(875) In an exemplary embodiment, R.sub.A, R.sub.B, R.sub.C, and R.sub.D are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
(876) In an exemplary embodiment, R.sub.A, R.sub.B, R.sub.C, and R.sub.D are each independently a substituted or unsubstituted phenyl group.
(877) In an exemplary embodiment, R.sub.447 and R.sub.448 are each a hydrogen atom.
(878) In an exemplary embodiment, the substituent for “substituted or unsubstituted” is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R.sub.901a)(R.sub.902a)(R.sub.903a), —O—(R.sub.904a), —S—(R.sub.905a), —N(R.sub.906a)(R.sub.907a), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms,
(879) R.sub.901a to R.sub.907a are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms;
(880) when two or more R.sub.901a are present, the two or more R.sub.901a are mutually the same or different;
(881) when two or more R.sub.902a are present, the two or more R.sub.902a are mutually the same or different;
(882) when two or more R.sub.903a are present, the two or more R.sub.903a are mutually the same or different;
(883) when two or more R.sub.904a are present, the two or more R.sub.904a are mutually the same or different;
(884) when two or more R.sub.905a are present, the two or more R.sub.905a are mutually the same or different;
(885) when two or more R.sub.905a are present, the two or more R.sub.905a are mutually the same or different; and
(886) when two or more R.sub.907a are present, the two or more R.sub.907a are mutually the same or different.
(887) In an exemplary embodiment, the substituent for “substituted or unsubstituted” is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
(888) In an exemplary embodiment, the substituent for “substituted or unsubstituted” is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.
(889) In the sixth and seventh compounds, it is preferable that all groups described as “substituted or unsubstituted” groups are “unsubstituted” groups.
(890) In the organic EL device of the exemplary embodiment, the sixth compound is preferably a compound that emits light having the maximum peak wavelength in a range from 430 nm to 480 nm.
(891) In the organic EL device of the exemplary embodiment, the seventh compound is preferably a compound that emits light having the maximum peak wavelength in a range from 430 nm to 480 nm.
(892) A measurement method of the maximum peak wavelength of a compound is as follows. A toluene solution of a measurement target compound at a concentration ranging from 10.sup.−6 mol/L to 10.sup.−5 mol/L is prepared and put in a quartz cell. An emission spectrum (ordinate axis: luminous intensity, abscissa axis: wavelength) of the thus-obtained sample is measured at a normal temperature (300K). The emission spectrum is measurable using a spectrophotometer (machine name: F-7000) manufactured by Hitachi High-Tech Science Corporation. It should be noted that the machine for measuring the emission spectrum is not limited to the machine used herein.
(893) A peak wavelength of the emission spectrum exhibiting the maximum luminous intensity is defined as the maximum peak wavelength. Herein, the maximum peak wavelength of fluorescence is sometimes referred to as the maximum fluorescence peak wavelength (FL-peak).
(894) In the organic EL device of the exemplary embodiment, when the first emitting layer contains the first compound and the seventh compound, a lowest singlet energy S.sub.1(H1) of the first compound and a lowest singlet energy S.sub.1(D7) of the seventh compound preferably satisfy a relationship of a numerical formula (Numerical Formula 1) below.
S.sub.1(H1)>S.sub.1(D7) (Numerical Formula 1)
(895) In the organic EL device of the exemplary embodiment, when the second emitting layer contains the second compound and the sixth compound, a lowest singlet energy S.sub.1(H2) of the second compound and a lowest singlet energy S.sub.1(D6) of the sixth compound preferably satisfy a relationship of a numerical formula (Numerical Formula 2) below.
S.sub.1(H2)>S.sub.1(D6) (Numerical Formula 2)
Singlet Energy S.sub.1
(896) A method of measuring a singlet energy S.sub.1 with use of a solution (occasionally referred to as a solution method) is exemplified by a method below.
(897) A toluene solution of a measurement target compound at a concentration ranging from 10.sup.−5 mol/L to 10.sup.−4 mol/L is prepared and put in a quartz cell. An absorption spectrum (ordinate axis: absorption intensity, abscissa axis: wavelength) of the thus-obtained sample is measured at a normal temperature (300K). A tangent is drawn to the fall of the absorption spectrum on the long-wavelength side, and a wavelength value λedge (nm) at an intersection of the tangent and the abscissa axis is assigned to a conversion equation (F2) below to calculate singlet energy.
S.sub.1 [eV]=1239.85/λedge Conversion Equation (F2)
(898) Any device for measuring absorption spectrum is usable. For instance, a spectrophotometer (U3310 manufactured by Hitachi, Ltd.) is usable.
(899) The tangent to the fall of the absorption spectrum on the long-wavelength side is drawn as follows. While moving on a curve of the absorption spectrum in a long-wavelength direction from the local maximum closest to the long-wavelength side among the local maximums of the absorption spectrum, a tangent at each point on the curve is checked. An inclination of the tangent is decreased and increased in a repeated manner as the curve falls (i.e., a value of the ordinate axis is decreased). A tangent drawn at a point of the minimum inclination closest to the long-wavelength side (except when absorbance is 0.1 or less) is defined as the tangent to the fall of the absorption spectrum on the long-wavelength side.
(900) The local maximum absorbance of 0.2 or less is not included in the above-mentioned local maximum absorbance closet to the long-wavelength side.
(901) Film Thickness of Emitting Layer
(902) A film thickness of each of the first and second emitting layers of the organic EL device in the exemplary embodiment is preferably in a range of 5 nm to 50 nm, more preferably in a range of 7 nm to 50 nm, further preferably in a range of 10 nm to 50 nm. When the film thickness of each of the first and second emitting layers is 5 nm or more, the first and second emitting layers are easily formable and chromaticity is easily adjustable. When the film thickness of each of the first and second emitting layers is 50 nm or less, a rise of the drive voltage is easily suppressible.
(903) Content Ratios of Compounds in Emitting Layer
(904) When the first emitting layer contains the first compound and the seventh compound, a content ratio of each of the first compound and the seventh compound in the first emitting layer preferably falls, for instance, within a range below.
(905) The content ratio of the first compound is preferably in a range from 80 mass % to 99 mass %, more preferably in a range from 90 mass % to 99 mass %, further preferably in a range from 95 mass % to 99 mass %.
(906) The content ratio of the seventh compound is preferably in a range from 1 mass % to 10 mass %, more preferably in a range from 1 mass % to 7 mass %, further preferably in a range from 1 mass % to 5 mass %.
(907) The upper limit of the total of the content ratios of the first compound and the seventh compound in the first emitting layer is 100 mass %.
(908) It is not excluded that the first emitting layer of the exemplary embodiment further contains a material(s) other than the first and seventh compounds.
(909) The first emitting layer may include a single type of the first compound or may include two or more types of the first compound. The first emitting layer may include a single type of the seventh compound or may include two or more types of the seventh compound.
(910) When the second emitting layer contains the second compound and the sixth compound, a content ratio of each of the second compound and the sixth compound in the second emitting layer preferably falls, for instance, within a range below.
(911) The content ratio of the second compound is preferably in a range from 80 mass % to 99 mass %, more preferably in a range from 90 mass % to 99 mass %, further preferably in a range from 95 mass % to 99 mass %.
(912) The content ratio of the sixth compound is preferably in a range from 1 mass % to 10 mass %, more preferably in a range from 1 mass % to 7 mass %, further preferably in a range from 1 mass % to 5 mass %.
(913) The upper limit of the total of the content ratios of the second compound and the sixth compound in the second emitting layer is 100 mass %.
(914) It is not excluded that the second emitting layer of the exemplary embodiment further contains a material(s) other than the second and sixth compounds.
(915) The second emitting layer may include a single type of the second compound or may include two or more types of the second compound. The second emitting layer may include a single type of the sixth compound or may include two or more types of the sixth compound.
(916) First Electron Transporting Layer
(917) In the organic EL device of the exemplary embodiment, the first electron transporting layer contains a third compound represented by a formula (3) below.
(918) In the organic EL device according to the exemplary embodiment, the first electron transporting layer preferably consists of the third compound.
(919) Third Compound
(920) The third compound represented by the formula (3) will be described. In some cases, the fourth compound contained in the second electron transporting layer and the fifth compound contained in the third electron transporting layer are represented by the formula (3).
(921) ##STR00445##
(922) In the formula (3), A is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
(923) B is a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms;
(924) L is a single bond, a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, a substituted or unsubstituted (n+1)-valent heterocyclic group having 5 to 13 ring atoms, or a (n+1)-valent group having a structure in which two or three different groups selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms are bonded to each other;
(925) C is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 60 ring atoms;
(926) n is 1, 2 or 3;
(927) when n is 2 or more, L is not a single bond; and
(928) when n is 2 or more, a plurality of C are mutually the same or different.
(929) In the organic EL device according to the exemplary embodiment, the third compound is preferably represented by a formula (31) or a formula (310).
(930) ##STR00446##
(931) In the formula (31):
(932) A, B and C represent the same as A, B and C defined in the formula (3);
(933) at least one combination of adjacent two or more of R.sub.31 to R.sub.34 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(934) R.sub.31 to R.sub.34 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(935) ##STR00447##
(936) In the formula (310):
(937) A and B represent the same as A and B defined in the formula (3);
(938) X.sub.30 is CR.sub.51R.sub.52, NR.sub.53, an oxygen atom, or a sulfur atom;
(939) when X.sub.30 is CR.sub.51R.sub.52, a combination of R.sub.51 and R.sub.52 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(940) at least one combination of adjacent two or more of R.sub.300 to R.sub.304 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(941) R.sub.53, and R.sub.51, R.sub.52, and R.sub.300 to R.sub.304 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(942) na is 3; and a plurality of R.sub.300 are mutually the same or different.
(943) In the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(944) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(945) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(946) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and
(947) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
(948) In the organic EL device of the exemplary embodiment, the third compound is also preferably a compound represented by a formula (32), a formula (33), a formula (34), or a formula (35).
(949) ##STR00448##
(950) In the formulae (32) to (35):
(951) A and B represent the same as A and B defined in the formula (3);
(952) X.sub.30 is CR.sub.51R.sub.52, NR.sub.53, an oxygen atom, or a sulfur atom;
(953) when X.sub.30 is CR.sub.51R.sub.52, a combination of R.sub.51 and R.sub.52 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(954) at least one combination of adjacent two or more of R.sub.301 to R.sub.308 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(955) R.sub.53, and R.sub.51, R.sub.52, and R.sub.301 to R.sub.308 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(956) In the organic EL device of the exemplary embodiment, the third compound is also preferably the compound represented by the formula (32).
(957) In the organic EL device of the exemplary embodiment, the third compound is also preferably a compound represented by a formula (36).
(958) ##STR00449##
(959) In the formula (36):
(960) A, B and C represent the same as A, B and C defined in the formula (3);
(961) at least one combination of adjacent two or more of R.sub.32 to R.sub.39 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(962) R.sub.32 to R.sub.39 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(963) In the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(964) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(965) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(966) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and
(967) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
(968) In the third compound of the organic EL device of the exemplary embodiment, C is preferably a substituted or unsubstituted heterocyclic group having 13 to 35 ring atoms.
(969) In the third compound of the organic EL device of the exemplary embodiment, C is preferably a substituted or unsubstituted aryl group having 14 to 24 ring carbon atoms.
(970) In the organic EL device of the exemplary embodiment, the third compound is preferably a compound represented by a formula (37).
(971) ##STR00450##
(972) In the formula (37):
(973) A, B and L represent the same as A, B and L defined in the formula (3);
(974) Cz is a group represented by a formula (Cz1), (Cz2), or (Cz3);
(975) n is 1, 2 or 3; and
(976) when n is 2 or 3, a plurality of Cz are mutually the same or different.
(977) ##STR00451##
(978) In the formulae (Cz1), (Cz2), and (Cz3):
(979) at least one combination of adjacent two or more of R.sub.311 to R.sub.318 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(980) at least one combination of adjacent two or more of R.sub.320 to R.sub.324 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(981) at least one combination of adjacent two or more of R.sub.330 to R.sub.334 and Rx are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(982) at least one combination of adjacent two or more of R.sub.340 to R.sub.344 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(983) at least one combination of adjacent two or more of R.sub.351 to R.sub.358 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(984) R.sub.311 to R.sub.318, R.sub.320 to R.sub.324, R.sub.330 to R.sub.334, R.sub.X, R.sub.340 to R.sub.344 and R.sub.351 to R.sub.358 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(985) n1, n2 and n3 are 3;
(986) three R.sub.320 are mutually the same or different;
(987) three R.sub.330 are mutually the same or different;
(988) three R.sub.340 are mutually the same or different; and
(989) * in the formulae (Cz1), (Cz2), and (Cz3) is bonded to L.
(990) In the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(991) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(992) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(993) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and
(994) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
(995) In the organic EL device of the exemplary embodiment, the compound represented by the formula (3) is a compound represented by a formula (38) below.
(996) ##STR00452##
(997) In the formula (38):
(998) A and B represent the same as A and B defined in the formula (3);
(999) La is a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon ring group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms; and
(1000) Ac is a group represented by one of formulae (Ac1), (Ac2), and (Ac3) below.
(1001) ##STR00453##
(1002) In the formula (Ac1):
(1003) X.sub.31 to X.sub.36 are each independently a nitrogen atom, a carbon atom bonded to La, or a carbon atom bonded to Ry;
(1004) at least one of X.sub.31 to X.sub.36 is a nitrogen atom;
(1005) one of X.sub.31 to X.sub.36 is a carbon atom bonded to La;
(1006) Ry is a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(1007) when a plurality of Ry are present, the plurality of Ry are mutually the same or different.
(1008) In the formula (Ac2):
(1009) X.sub.21 to X.sub.28 are each independently a nitrogen atom, a carbon atom bonded to La, or a carbon atom bonded to Rz;
(1010) at least one of X.sub.21 to X.sub.28 is a nitrogen atom;
(1011) one of X.sub.21 to X.sub.28 is a carbon atom bonded to La; when a plurality of Rz are present, at least one combination of adjacent two or more of the plurality of Rz are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded; and
(1012) Rz neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(1013) In the formula (Ac3):
(1014) n4 is 1, 2, 3, 4, 5, 6, 7, 8 or 9;
(1015) D is an aryl group having a cyano group whose number is n4 and having 6 to 18 ring carbon atoms, or a heterocyclic group having a cyano group whose number is n4 and having 5 to 13 ring atoms;
(1016) D has a substituent other than a cyano group or does not have a substituent other than a cyano group; and
(1017) * in the formula (Ac3) is bonded to La.
(1018) In the third compound, R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1019) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(1020) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(1021) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and
(1022) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
(1023) In the organic EL device of the exemplary embodiment, the compound represented by the formula (38) is preferably a compound represented by a formula (381) below.
(1024) ##STR00454##
(1025) In the formula (381):
(1026) A, B, and Ac represent the same as A, B, and Ac defined in the formula (38);
(1027) at least one combination of adjacent two or more of R.sub.381 to R.sub.384 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(1028) R.sub.381 to R.sub.384 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(1029) R.sub.901 to R.sub.904 represents the same as R.sub.901 to R.sub.904 defined in the formula (38).
(1030) In the organic EL device of the exemplary embodiment, the compound represented by the formula (38) is preferably a compound represented by a formula (382) below.
(1031) ##STR00455##
(1032) In the formula (382):
(1033) A, B, and Ac represent the same as A, B, and Ac defined in the formula (38);
(1034) R.sub.383 is a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; and
(1035) R.sub.901 to R.sub.904 represents the same as R.sub.901 to R.sub.904 defined in the formula (38).
(1036) In the organic EL device of the exemplary embodiment, L is preferably a single bond or a substituted or unsubstituted (n+1)-valent aromatic hydrocarbon ring group having 6 to 12 ring carbon atoms.
(1037) In the organic EL device of the exemplary embodiment, L or La is preferably a single bond.
(1038) In the organic EL device of the exemplary embodiment, L or La is preferably an aromatic hydrocarbon ring group represented by a formula (L.sub.1) or a formula (L.sub.2).
(1039) ##STR00456##
(1040) In the formulae (L.sub.1) and (L.sub.2):
(1041) one of two * is bonded to a triazine ring shown in the formula (3);
(1042) the other of two * is bonded to (C)n, (Cz)n or Ac;
(1043) when n is 1, the number of * bonded to (C)n or (Cz)n is 1;
(1044) when n is 2, the number of * bonded to (C)n or (Cz)n is 2; and
(1045) when n is 3, the number of * bonded to (C)n or (Cz)n is 3
(1046) In the organic EL device of the exemplary embodiment, A is preferably a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
(1047) In the third compound of the organic EL device of the exemplary embodiment, A is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
(1048) In the third compound of the organic EL device of the exemplary embodiment, A is preferably a phenyl group, a biphenyl group, or a naphthyl group.
(1049) In the third compound of the organic EL device of the exemplary embodiment, B is preferably a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
(1050) In the third compound of the organic EL device of the exemplary embodiment, B is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
(1051) In the third compound of the organic EL device of the exemplary embodiment, A and B are preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.
(1052) In the third compound, it is preferable that all groups described as “substituted or unsubstituted” groups are “unsubstituted” groups.
(1053) Manufacturing Method of Third Compound
(1054) The third compound can be manufactured by a known method. Moreover, the third compound can also be manufactured by application of known substitution reactions and materials depending on a target compound, based on a known method.
(1055) Specific Examples of Third Compound
(1056) Specific examples of the third compound include the following compounds. It should however be noted that the invention is not limited by the specific examples of the third compound.
(1057) ##STR00457## ##STR00458## ##STR00459## ##STR00460## ##STR00461## ##STR00462## ##STR00463## ##STR00464## ##STR00465## ##STR00466## ##STR00467## ##STR00468## ##STR00469## ##STR00470## ##STR00471## ##STR00472## ##STR00473## ##STR00474## ##STR00475## ##STR00476## ##STR00477## ##STR00478## ##STR00479## ##STR00480## ##STR00481## ##STR00482## ##STR00483## ##STR00484## ##STR00485## ##STR00486## ##STR00487## ##STR00488## ##STR00489## ##STR00490## ##STR00491## ##STR00492## ##STR00493## ##STR00494## ##STR00495## ##STR00496## ##STR00497## ##STR00498## ##STR00499## ##STR00500## ##STR00501## ##STR00502## ##STR00503## ##STR00504## ##STR00505## ##STR00506## ##STR00507## ##STR00508## ##STR00509## ##STR00510## ##STR00511## ##STR00512## ##STR00513## ##STR00514## ##STR00515## ##STR00516## ##STR00517## ##STR00518##
(1058) An arrangement of the organic EL device according to the exemplary embodiment will be further described. It should be noted that the reference numerals will be sometimes omitted below.
(1059) Substrate
(1060) The substrate is used as a support for the organic EL device. For instance, glass, quartz, plastics and the like are usable for the substrate. A flexible substrate is also usable. The flexible substrate is a bendable substrate, which is exemplified by a plastic substrate. Examples of the material for the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Moreover, an inorganic vapor deposition film is also usable.
(1061) Anode
(1062) Metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more) is preferably used as the anode formed on the substrate. Specific examples of the material include ITO (Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chrome (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of a metal material (e.g., titanium nitride) are usable.
(1063) The material is typically formed into a film by a sputtering method. For instance, the indium oxide-zinc oxide can be formed into a film by the sputtering method using a target in which zinc oxide in a range from 1 mass % to 10 mass % is added to indium oxide. Moreover, for instance, the indium oxide containing tungsten oxide and zinc oxide can be formed by the sputtering method using a target in which tungsten oxide in a range from 0.5 mass % to 5 mass % and zinc oxide in a range from 0.1 mass % to 1 mass % are added to indium oxide. In addition, the anode may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method or the like.
(1064) Among the organic layers formed on the anode, since the hole injecting layer adjacent to the anode is formed of a composite material into which holes are easily injectable irrespective of the work function of the anode, a material usable as an electrode material (e.g., metal, an alloy, an electroconductive compound, a mixture thereof, and the elements belonging to the group 1 or 2 of the periodic table) is also usable for the anode.
(1065) A material having a small work function such as elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, an alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, a rare earth metal such as europium (Eu) and ytterbium (Yb), alloys including the rare earth metal are also usable for the anode. It should be noted that the vacuum deposition method and the sputtering method are usable for forming the anode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the anode, the coating method and the inkjet method are usable.
(1066) Cathode
(1067) It is preferable to use metal, an alloy, an electroconductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less) for the cathode. Examples of the material for the cathode include elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, the alkali metal such as lithium (Li) and cesium (Cs), the alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, the rare earth metal such as europium (Eu) and ytterbium (Yb), and alloys including the rare earth metal.
(1068) It should be noted that the vacuum deposition method and the sputtering method are usable for forming the cathode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the cathode, the coating method and the inkjet method are usable.
(1069) By providing the electron injecting layer, various conductive materials such as A.sub.1, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide may be used for forming the cathode regardless of the work function. The conductive materials can be formed into a film using the sputtering method, inkjet method, spin coating method and the like.
(1070) Hole Injecting Layer
(1071) The hole injecting layer is a layer containing a substance exhibiting a high hole injectability. Examples of the substance exhibiting a high hole injectability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chrome oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
(1072) In addition, the examples of the highly hole-injectable substance further include: an aromatic amine compound, which is a low-molecule organic compound, such as 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1); and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).
(1073) In addition, a high polymer compound (e.g., oligomer, dendrimer and polymer) is usable as the substance exhibiting a high hole injectability. Examples of the high-molecule compound include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamide](abbreviation: PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Moreover, an acid-added high polymer compound such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrene sulfonic acid) (PAni/PSS) are also usable.
(1074) Hole Transporting Layer
(1075) The hole transporting layer is a layer containing a highly hole-transporting substance. An aromatic amine compound, carbazole derivative, anthracene derivative and the like are usable for the hole transporting layer. Specific examples of a material for the hole transporting layer include an aromatic amine compound such as 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above-described substances mostly have a hole mobility of 10.sup.−6 cm.sup.2/(V.Math.s) or more.
(1076) For the hole transporting layer, a carbazole derivative such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA) and an anthracene derivative such as t-BuDNA, DNA, and DPAnth may be used. A high polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) is also usable.
(1077) However, in addition to the above substances, any substance exhibiting a higher hole transportability than an electron transportability may be used. It should be noted that the layer containing the substance exhibiting a high hole transportability may be not only a single layer but also a laminate of two or more layers formed of the above substance(s).
(1078) The organic EL device of the exemplary embodiment also preferably further includes a hole transporting layer provided between the first emitting layer and the second emitting layer in direct contact with each other and the anode, in which the hole transporting layer preferably contain a compound represented by a formula (C1) or (D1) below.
(1079) ##STR00519##
(1080) In the formula (C1):
(1081) L.sub.A, L.sub.B, and L.sub.C are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 13 ring atoms;
(1082) A.sub.A, B.sub.B, and C.sub.C are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a group represented by —Si(R′.sub.901)(R′.sub.902)(R′.sub.903);
(1083) R′.sub.901 to R′.sub.903 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms;
(1084) when a plurality of R′.sub.901 are present, the plurality of R′.sub.901 are mutually the same or different;
(1085) when a plurality of R′.sub.902 are present, the plurality of R′.sub.902 are mutually the same or different; and
(1086) when a plurality of R′.sub.903 are present, the plurality of R′.sub.903 are mutually the same or different.
(1087) ##STR00520##
(1088) In the formula (D1):
(1089) A.sub.41 and A.sub.42 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
(1090) L.sub.41 and L.sub.42 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms;
(1091) at least one combination of adjacent two or more of Ra.sub.410 to Ra.sub.414 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(1092) at least one combination of adjacent two or more of Ra.sub.420 to Ra.sub.424 are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded;
(1093) Ra.sub.410 to Ra.sub.414 and Ra.sub.420 to Ra.sub.424 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a halogen atom, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1094) m1 and m2 are 3;
(1095) three Ra.sub.410 are mutually the same or different; and
(1096) three Ra.sub.420 are mutually the same or different.
(1097) In the compound represented by the formula (D1), R.sub.901, R.sub.902, R.sub.903, and R.sub.904 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1098) when a plurality of R.sub.901 are present, the plurality of R.sub.901 are mutually the same or different;
(1099) when a plurality of R.sub.902 are present, the plurality of R.sub.902 are mutually the same or different;
(1100) when a plurality of R.sub.903 are present, the plurality of R.sub.903 are mutually the same or different; and
(1101) when a plurality of R.sub.904 are present, the plurality of R.sub.904 are mutually the same or different.
(1102) In the organic EL device of the exemplary embodiment, the hole transporting layer preferably contains the compound represented by the formula (C1).
(1103) In the compound represented by the formula (C1), it is preferable that all groups described as “substituted or unsubstituted” groups are “unsubstituted” groups.
(1104) Electron Transporting Layer
(1105) The organic EL device according to the exemplary embodiment may further include an additional electron transporting layer (e.g., the second electron transporting layer and the third electron transporting layer) between the cathode and the first emitting layer/the second emitting layer.
(1106) The electron transporting layer is a layer containing a highly electron-transporting substance. For the electron transporting layer, 1) a metal complex such as an aluminum complex, beryllium complex, and zinc complex, 2) a hetero aromatic compound such as imidazole derivative, benzimidazole derivative, azine derivative, carbazole derivative, and phenanthroline derivative, and 3) a high polymer compound are usable. Specifically, as a low-molecule organic compound, a metal complex such as Alq, tris(4-methyl-8-quinolinato)aluminum (abbreviation: Almq.sub.3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq.sub.2), BAlq, Znq, ZnPBO and ZnBTZ is usable. In addition to the metal complex, a heteroaromatic compound such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs) is usable. In the exemplary embodiment, for instance, a benzimidazole compound is suitably usable for the additional electron transporting layer. The above-described substances mostly have an electron mobility of 10.sup.−6 cm.sup.2Ns or more. It should be noted that any substance other than the above substance may be used for the electron transporting layer as long as the substance exhibits a higher electron transportability than the hole transportability.
(1107) Further, a high polymer compound is usable for the electron transporting layer. For instance, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)](abbreviation: PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)](abbreviation: PF-BPy) and the like are usable.
(1108) Electron Injecting Layer
(1109) The electron injecting layer is a layer containing a highly electron-injectable substance. Examples of a material for the electron injecting layer include an alkali metal, alkaline earth metal and a compound thereof, examples of which include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF.sub.2), and lithium oxide (LiOx). In addition, the alkali metal, alkaline earth metal or the compound thereof may be added to the substance exhibiting the electron transportability in use. Specifically, for instance, magnesium (Mg) added to Alq may be used. In this case, the electrons can be more efficiently injected from the cathode.
(1110) Alternatively, the electron injecting layer may be provided by a composite material in a form of a mixture of the organic compound and the electron donor. Such a composite material exhibits excellent electron injectability and electron transportability since electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, the above examples (e.g., the metal complex and the hetero aromatic compound) of the substance forming the electron transporting layer are usable. As the electron donor, any substance exhibiting electron donating property to the organic compound is usable. Specifically, the electron donor is preferably alkali metal, alkaline earth metal and rare earth metal such as lithium, cesium, magnesium, calcium, erbium and ytterbium. The electron donor is also preferably alkali metal oxide and alkaline earth metal oxide such as lithium oxide, calcium oxide, and barium oxide. Moreover, a Lewis base such as magnesium oxide is usable. Further, the organic compound such as tetrathiafulvalene (abbreviation: TTF) is usable.
(1111) In the organic EL device of the exemplary embodiment, a substituent for a “substituted or unsubstituted” group is preferably at least one group selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring carbon atoms, and a heterocyclic group having 5 to 18 ring atoms.
(1112) In the organic EL device of the exemplary embodiment, a substituent for a “substituted or unsubstituted” group is preferably an alkyl group having 1 to 5 carbon atoms.
(1113) Layer Formation Method
(1114) A method for forming each layer of the organic EL device in the present exemplary embodiment is subject to no limitation except for the above particular description. However, known methods of dry film-forming such as vacuum deposition, sputtering, plasma or ion plating and wet film-forming such as spin coating, dipping, flow coating or ink-jet are applicable.
(1115) Film Thickness
(1116) A film thickness of each of the organic layers of the organic EL device in the exemplary embodiment is not limited unless otherwise specified in the above. In general, the thickness preferably ranges from several nanometers to 1 μm because excessively small film thickness is likely to cause defects (e.g. pin holes) and excessively large thickness leads to the necessity of applying high voltage and consequent reduction in efficiency.
(1117) Emission Wavelength of Organic EL Device
(1118) The organic electroluminescence device of the exemplary embodiment preferably emits light having a maximum peak wavelength in a range from 430 nm to 480 nm when the organic electroluminescence device is driven.
(1119) The maximum peak wavelength of the light emitted from the organic EL device when being driven is measured as follows. Voltage is applied on the organic EL devices such that a current density becomes 10 mA/cm.sup.2, where spectral radiance spectrum is measured by a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). A peak wavelength of an emission spectrum, at which the luminous intensity of the obtained spectral radiance spectrum is at the maximum, is measured and defined as a maximum peak wavelength (unit: nm).
(1120) According to the exemplary embodiment, an organic electroluminescence device configured to emit light with a high luminous efficiency and a long lifetime can be provided.
Second Exemplary Embodiment
(1121) Organic Electroluminescence Device
(1122) An arrangement of an organic EL device according to a second exemplary embodiment will be described below.
(1123) An organic EL device according to the second exemplary embodiment is the same as the organic EL device according to the first exemplary embodiment except for a difference in the first emitting layer and the second emitting layer. Accordingly, in the description of the second exemplary embodiment, the same components as those in the first exemplary embodiment are denoted by the same reference signs and names to simplify or omit an explanation of the components. Moreover, as the device arrangement, materials, and compounds unless otherwise specified in the second exemplary embodiment, the same device arrangement, materials, and compounds as described in the first exemplary embodiment are usable.
(1124) An organic EL device according to the exemplary embodiment includes an anode, a cathode, a first emitting layer and a second emitting layer interposed between the anode and the cathode, the first and second emitting layers being in a direct contact with each other, and a first electron transporting layer between the first and second emitting layers being in a direct contact with each other and the cathode, in which the first emitting layer includes a first compound as a first host material, the second emitting layer includes a second compound as a second host material, the first host material and the second host material are different from each other, the first emitting layer at least includes a compound that emits light having a maximum peak wavelength of 500 nm or less, the second emitting layer at least includes a compound that emits light having a maximum peak wavelength of 500 nm or less, the compound that is contained in the first emitting layer and emits light having the maximum peak wavelength of 500 nm or less and the compound that is contained in the second emitting layer and emits light having the maximum peak wavelength of 500 nm or less are mutually the same or different, a triplet energy T.sub.1(H1) of the first host material and a triplet energy T.sub.1(H2) of the second host material satisfy a numerical formula below (Numerical Formula 1A), and the first electron transporting layer comprises a third compound represented by a formula (3) below,
T.sub.1(H1)>T.sub.1(H2) (Numerical Formula 1A).
(1125) The third compound contained in the first electron transporting layer of the organic EL device of the second exemplary embodiment is the same compound as the third compound described in the first exemplary embodiment.
(1126) Conventionally, Triplet-Triplet-Annihilation (sometimes referred to as TTA) is known as a technique for enhancing the luminous efficiency of the organic electroluminescence device. TTA is a mechanism in which triplet excitons collide with one another to generate singlet excitons. It should be noted that the TTA mechanism is also sometimes referred to as a TTF mechanism. TTF is an abbreviation for Triplet-Triplet Fusion.
(1127) The TTF phenomenon will be described. Holes injected from an anode and electrons injected from a cathode are recombined in an emitting layer to generate excitons. As for the spin state, as is conventionally known, singlet excitons account for 25% and triplet excitons account for 75%. In a conventionally known fluorescent device, light is emitted when singlet excitons of 25% are relaxed to the ground state. The remaining triplet excitons of 75% are returned to the ground state without emitting light through a thermal deactivation process. Accordingly, the theoretical limit value of the internal quantum efficiency of a conventional fluorescent device is believed to be 25%.
(1128) The behavior of triplet excitons generated within an organic substance has been theoretically examined. According to S. M. Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), assuming that high-order excitons such as quintet excitons are quickly returned to triplet excitons, triplet excitons (hereinafter abbreviated as 3A*) collide with one another with an increase in the density thereof, whereby a reaction shown by the following formula occurs. In the formula, 1A represents the ground state and 1A* represents the lowest singlet excitons.
(1129) 3A*+3A*.fwdarw.(4/9)1A+(1/9)1A*+(13/9)3A*
(1130) In other words, 5.sup.3A*.fwdarw.4.sup.1A+1A*, and it is expected that, among triplet excitons initially generated, which account for 75%, one fifth thereof (i.e., 20%) is changed to singlet excitons. Accordingly, the amount of singlet excitons which contribute to emission is 40%, which is a value obtained by adding 15% (75%×(1/5)=15%) to 25%, which is the amount ratio of initially generated singlet excitons. At this time, a ratio of luminous intensity derived from TTF (TTF ratio) relative to the total luminous intensity is 15/40, i.e., 37.5%. Assuming that singlet excitons are generated by collision of initially generated triplet excitons accounting for 75% (i.e., one singlet exciton is generated from two triplet excitons), a significantly high internal quantum efficiency of 62.5% is obtained, which is a value obtained by adding 37.5% (75%×(1/2)=37.5%) to 25% (the amount ratio of initially generated singlet excitons). At this time, the TTF ratio is 37.5/62.5=60%.
(1131) In the organic electroluminescence device of the exemplary embodiment, it is considered that triplet excitons generated by recombination of holes and electrons in the first emitting layer and present on an interface between the first emitting layer and organic layer(s) in direct contact therewith are not likely to be quenched even under the presence of excessive carriers on the interface between the first emitting layer and the organic layer(s). For instance, the presence of a recombination region locally on an interface between the first emitting layer and a hole transporting layer or an electron blocking layer is considered to cause quenching by excessive electrons. Meanwhile, the presence of a recombination region locally on an interface between the first emitting layer and an electron transporting layer or a hole blocking layer is considered to cause quenching by excessive holes.
(1132) The organic electroluminescence device of the exemplary embodiment includes at least two emitting layers (i.e., the first emitting layer and the second emitting layer) which satisfy a predetermined relationship. A triplet energy T.sub.1(H1) of the first host material in the first emitting layer and a triplet energy T.sub.1(H2) of the second host material in the second emitting layer satisfy a relationship of the numerical formula (Numerical Formula 1A).
(1133) By including the first emitting layer and the second emitting layer that satisfy the numerical formula (Numerical Formula 1A), triplet excitons generated in the first emitting layer can transfer to the second emitting layer without being quenched by excessive carriers and be prevented from back-transferring from the second emitting layer to the first emitting layer. Consequently, the second emitting layer exhibits the TTF mechanism to effectively generate singlet excitons, thereby improving the luminous efficiency.
(1134) Accordingly, the laminated emitting unit in the organic electroluminescence device includes, as different regions, the first emitting layer mainly generating triplet excitons and the second emitting layer mainly exhibiting the TTF mechanism using triplet excitons having transferred from the first emitting layer, and a difference in triplet energy is provided by using a compound having a smaller triplet energy than that of the first host material in the first emitting layer as the second host material in the second emitting layer, thereby improving the luminous efficiency.
(1135) In the organic EL device of the exemplary embodiment, the triplet energy T.sub.1(H1) of the first host material and the triplet energy T.sub.1(H2) of the second host material preferably satisfy a relationship of a numerical formula (Numerical Formula 5) below.
T.sub.1(H1)−T.sub.1(H2)>0.03 eV (Numerical Formula 5)
Emission Wavelength of Organic EL Device
(1136) The organic electroluminescence device of the exemplary embodiment preferably emits light having the maximum peak wavelength of 500 nm or less when the organic electroluminescence device is driven.
(1137) The organic electroluminescence device of the exemplary embodiment more preferably emits light having the maximum peak wavelength in a range from 430 nm to 480 nm when the organic electroluminescence device is driven.
(1138) The main peak wavelength of light emitted from the organic EL device can be measured by the aforementioned method.
(1139) First Emitting Layer
(1140) The first emitting layer includes the first host material. The first host material is a compound different from the second host material contained in the second emitting layer.
(1141) The first emitting layer at least contains a compound that emits light having the maximum peak wavelength of 500 nm or less. This “compound that emits light having the maximum peak wavelength of 500 nm or less” may be the first host material or a compound different from the first host material. The compound that emits light having the maximum peak wavelength of 500 nm or less and is contained in the first emitting layer is preferably a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less.
(1142) In the exemplary embodiment, the compound that emits light having the maximum peak wavelength of 500 nm or less is preferably a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less.
(1143) In the organic EL device of the exemplary embodiment, it is preferable that the first emitting layer further contains a first dopant material and the first dopant material is a fluorescent compound.
(1144) In the organic EL device of the exemplary embodiment, it is preferable that the first dopant material is a compound not having an azine ring structure in a molecule.
(1145) In the organic EL device of the exemplary embodiment, the first dopant material is preferably not a boron-containing complex, more preferably not a complex.
(1146) In the organic EL device of the exemplary embodiment, it is preferable that the first emitting layer does not contain a metal complex. Moreover, in the organic EL device of the exemplary embodiment, it is also preferable that the first emitting layer does not contain a boron-containing complex.
(1147) In the organic EL device of the exemplary embodiment, it is preferable that the first emitting layer does not contain a phosphorescent material (dopant material).
(1148) In addition, it is preferable that the first emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of the heavy-metal complex herein include iridium complex, osmium complex, and platinum complex.
(1149) In the organic EL device of the exemplary embodiment, the first dopant material is preferably the compound that emits light having the maximum peak wavelength of 500 nm or less, more preferably a compound that emits fluorescence having the maximum peak wavelength of 500 nm or less. A measurement method of the maximum peak wavelength of a compound is as described above.
(1150) In an emission spectrum of the first dopant material, where a peak exhibiting a maximum luminous intensity is defined as a maximum peak and a height of the maximum peak is defined as 1, heights of other peaks appearing in the emission spectrum are preferably less than 0.6. It should be noted that the peaks in the emission spectrum are defined as local maximal values.
(1151) Moreover, in the emission spectrum of the first dopant material, the number of peaks is preferably less than three.
(1152) In the organic EL device of the exemplary embodiment, the first emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the organic EL device is driven.
(1153) The maximum peak wavelength of light emitted from the organic EL device when being driven can be measured by a method described below.
(1154) Maximum Peak Wavelength λp of Light Emitted from Emitting Layer when Organic EL Device is Driven
(1155) For a maximum peak wavelength λp.sub.1 of light emitted from the first emitting layer when the organic EL device is driven, the organic EL device is manufactured by using the same material for the first emitting layer and the second emitting layer, and voltage is applied on the organic EL device so that a current density becomes 10 mA/cm.sup.2, where spectral radiance spectrum is measured by a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). The maximum peak wavelength λp.sub.1 (unit: nm) is calculated from the obtained spectral radiance spectrum.
(1156) For a maximum peak wavelength λp.sub.2 of light emitted from the second emitting layer when the organic EL device is driven, the organic EL device is manufactured by using the same material for the first emitting layer and the second emitting layer, and voltage is applied on the organic EL device so that a current density becomes 10 mA/cm.sup.2, where spectral radiance spectrum is measured by a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). The maximum peak wavelength λp.sub.2 (unit: nm) is calculated from the obtained spectral radiance spectrum.
(1157) In the organic EL device of the exemplary embodiment, the singlet energy S.sub.1(H1) of the first host material and the singlet energy S.sub.1(D1) of the first dopant material preferably satisfy a relationship of a numerical formula (Numerical Formula 20) below.
S.sub.1(H1)>S.sub.1(D1) (Numerical Formula 20)
(1158) The singlet energy S.sub.1 means an energy difference between the lowest singlet state and the ground state.
(1159) When the first host material and the first dopant material satisfy the relationship of the numerical formula (Numerical Formula 20), singlet excitons generated on the first host material are easily transferred from the first host material to the first dopant material, thereby contributing to fluorescence of the first dopant material.
(1160) In the organic EL device of the exemplary embodiment, the triplet energy T.sub.1(H1) of the first host material and the triplet energy T.sub.1(D1) of the first dopant material preferably satisfy a relationship of a numerical formula (Numerical Formula 2A) below.
T.sub.1(D1)>T.sub.1(H1) (Numerical Formula 2A)
(1161) When the first host material and the first dopant material satisfy the relationship of the numerical formula (Numerical Formula 2A), triplet excitons generated in the first emitting layer are transferred not onto the first dopant material having higher triplet energy but onto the first host material, thereby being easily transferred to the second emitting layer.
(1162) The organic EL device of the exemplary embodiment preferably satisfies a numerical formula (Numerical Formula 2B) below.
T.sub.1(D1)>T.sub.1(H1)>T.sub.1(H2) (Numerical Formula 2B)
Triplet Energy T.sub.1
(1163) A method of measuring triplet energy T.sub.1 is exemplified by a method below.
(1164) A measurement target compound is dissolved in EPA (diethylether isopentane:ethanol=5:5:2 in volume ratio) so as to fall within a range from 10.sup.−5 mol/L to 10.sup.−4 mol/L, and the obtained solution is encapsulated in a quartz cell to provide a measurement sample. A phosphorescence spectrum (ordinate axis: phosphorescent luminous intensity, abscissa axis: wavelength) of the measurement sample is measured at a low temperature (77K). A tangent is drawn to the rise of the phosphorescence spectrum close to the short-wavelength region. An energy amount is calculated by a conversion equation (F1) below on a basis of a wavelength value λ.sub.edge [nm] at an intersection of the tangent and the abscissa axis. The calculated energy amount is defined as triplet energy T.sub.1.
T.sub.1 [eV]=1239.85/λ.sub.edge Conversion Equation (F1)
(1165) The tangent to the rise of the phosphorescence spectrum close to the short-wavelength region is drawn as follows. While moving on a curve of the phosphorescence spectrum from the short-wavelength region to the local maximum closest to the short-wavelength region among the local maximums of spectral values, a tangent is checked at each point on the curve toward the long-wavelength of the phosphorescence spectrum. An inclination of the tangent is increased along the rise of the curve (i.e., a value of the ordinate axis is increased). A tangent drawn at a point of the local maximum inclination (i.e., a tangent at an inflection point) is defined as the tangent to the rise of the phosphorescence spectrum close to the short-wavelength region.
(1166) The local maximum with peak intensity being 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned local maximum closest to the short-wavelength region. The tangent drawn at a point of the local maximum of the spectral value being closest to the short-wavelength region and having the local maximum inclination is defined as a tangent to the rise of the phosphorescence spectrum close to the short-wavelength region.
(1167) For phosphorescence measurement, a spectrophotofluorometer body F-4500 (manufactured by Hitachi High-Technologies Corporation) is usable. Any device for phosphorescence measurement is usable. A combination of a cooling unit, a low temperature container, an excitation light source and a light-receiving unit may be used for phosphorescence measurement.
(1168) In the organic EL device of the exemplary embodiment, an electron mobility μH1 of the first host material and an electron mobility μH2 of the second host material preferably satisfy a relationship of a numerical formula (Numerical Formula 6) below.
μH2>μH1 (Numerical Formula 6)
(1169) When the first host material and the second host material satisfy the relationship of the numerical formula (Numerical Formula 6), a recombination ability of holes and electrons in the first emitting layer is improved.
(1170) The electron mobility can be measured according to impedance spectroscopy.
(1171) A measurement target layer having a thickness in a range from 100 nm to 200 nm is held between the anode and the cathode, to which a small alternating voltage of 100 mV or less is applied while a bias DC voltage is applied. A value of an alternating current (absolute value and phase) which flows at this time is measured. This measurement is performed while changing a frequency of the alternating voltage, and complex impedance (Z) is calculated from the current value and the voltage value. A frequency dependency of the imaginary part (ImM) of the modulus M=iωZ (i: imaginary unit, ω: angular frequency) is obtained. The reciprocal number of a frequency ω at which the ImM becomes the maximum is defined as a response time of electrons carried in the measurement target layer. The electron mobility is calculated by the following equation.
Electron Mobility=(Film Thickness of Measurement Target Layer).sup.2/(Response Time.Math.Voltage)
(1172) In the organic EL device of the exemplary embodiment, the first dopant material is preferably contained at more than 1.1 mass % in the first emitting layer. Specifically, the first emitting layer preferably contains the first dopant material at more than 1.1 mass % with respect to a total mass of the first emitting layer, more preferably at more than 1.2 mass % with respect to the total mass of the first emitting layer, further preferably at more than 1.5 mass % with respect to the total mass of the first emitting layer.
(1173) The first emitting layer preferably contains the first dopant material at 10 mass % or less with respect to the total mass of the first emitting layer, more preferably at 7 mass % or less with respect to the total mass of the first emitting layer, further preferably at 5 mass % or less with respect to the total mass of the first emitting layer.
(1174) In the organic EL device of the exemplary embodiment, the first emitting layer preferably contains the first emitting compound as the first host material at 60 mass % or more with respect to the total mass of the first emitting layer, more preferably at 70 mass % or more with respect to the total mass of the first emitting layer, further preferably at 80 mass % or more with respect to the total mass of the first emitting layer, more further preferably at 90 mass % or more with respect to the total mass of the first emitting layer, still further more preferably at 95 mass % or more with respect to the total mass of the first emitting layer.
(1175) The first emitting layer preferably contains the first host material at 99 mass % or less with respect to the total mass of the first emitting layer.
(1176) In a case where the first emitting layer contains the first host material and the first dopant material, an upper limit of a total of the content ratios of the first host material and the first dopant material is 100 mass %.
(1177) It is not excluded that the first emitting layer of the exemplary embodiment further contains a material(s) other than the first host material and the first dopant material.
(1178) The first emitting layer may include a single type of the first host material or may include two or more types of the first host material. The first emitting layer may include a single type of the first dopant material or may include two or more types of the first dopant material.
(1179) A film thickness of the first emitting layer of the organic EL device in the exemplary embodiment is preferably 3 nm or more, more preferably 5 nm or more. The film thickness of the first emitting layer being 3 nm or more is a film thickness enough for causing recombination of holes and electrons in the first emitting layer.
(1180) The film thickness of the first emitting layer of the organic EL device in the exemplary embodiment is preferably 15 nm or less, more preferably 10 nm or less. The film thickness of the first emitting layer being 15 nm or less is a film thickness thin enough for transfer of triplet excitons to the second emitting layer.
(1181) The film thickness of the first emitting layer of the organic EL device in the exemplary embodiment is more preferably in a range from 3 nm to 15 nm.
(1182) Second Emitting Layer
(1183) The second emitting layer contains the second host material. The second host material is a different compound from the first host material contained in the first emitting layer.
(1184) The second emitting layer at least contains a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less. This “compound that emits fluorescence having a maximum peak wavelength of 500 nm or less” may be the second host material or a different compound from the second host material. The compound that is contained in the second emitting layer and emits light having a maximum peak wavelength of 500 nm or less is preferably the compound that emits fluorescence having the maximum peak wavelength of 500 nm or less.
(1185) A measurement method of the maximum peak wavelength of a compound is as described above.
(1186) In the organic EL device of the exemplary embodiment, it is preferable that the second emitting layer further contains the second dopant material and the second dopant material is a fluorescent compound.
(1187) In the organic EL device of the exemplary embodiment, the second dopant material is preferably a compound that emits light having a maximum peak wavelength of 500 nm or less, more preferably a compound that emits fluorescence having a maximum peak wavelength of 500 nm or less.
(1188) In the organic EL device of the exemplary embodiment, the second emitting layer preferably emits light having a maximum peak wavelength of 500 nm or less when the organic EL device is driven.
(1189) In the organic EL device of the exemplary embodiment, a half bandwidth of the maximum peak of the second dopant material is preferably in a range from 1 nm to 20 nm.
(1190) In the organic EL device of the exemplary embodiment, a Stokes shift of the second dopant material preferably exceeds 7 nm.
(1191) When the Stokes shift of the second dopant material exceeds 7 nm, a reduction in the luminous efficiency due to self-absorption is likely to be inhibited.
(1192) The self-absorption is a phenomenon that emitted light is absorbed by the same compound to reduce luminous efficiency. The self-absorption is notably observed in a compound having a small Stokes shift (i.e., a large overlap between an absorption spectrum and a fluorescence spectrum). Accordingly, in order to reduce the self-absorption, it is preferable to use a compound having a large Stokes shift (i.e., a small overlap between the absorption spectrum and the fluorescence spectrum). The Stokes shift can be measured by a method described in Examples.
(1193) In the organic EL device of the exemplary embodiment, a triplet energy T.sub.1(D2) of the second dopant material and the triplet energy T.sub.1(H2) of the second host material preferably satisfy a relationship of a numerical formula (Numerical Formula 3) below.
T.sub.1(D2)>T.sub.1(H2) (Numerical Formula 3)
(1194) In the organic EL device according to the exemplary embodiment, when the second dopant material and the second host material satisfy the relationship of the numerical formula (Numerical Formula 3A), in transfer of triplet excitons generated in the first emitting layer to the second emitting layer, the triplet excitons energy-transfer not to the second dopant material having higher triplet energy but to molecules of the second host material. In addition, triplet excitons generated by recombination of holes and electrons on the second host material do not transfer to the second dopant material having higher triplet energy. Triplet excitons generated by recombination on molecules of the second dopant material quickly energy-transfer to molecules of the second host material.
(1195) Triplet excitons in the second host material do not transfer to the second dopant material but efficiently collide with one another on the second host material to generate singlet excitons by the TTF phenomenon.
(1196) In the organic EL device of the exemplary embodiment, a singlet energy S.sub.1(H2) of the second host material and a singlet energy S.sub.1(D2) of the second dopant material preferably satisfy a relationship of a numerical formula (Numerical Formula 4) below.
S.sub.1(H2)>S.sub.1(D2) (Numerical Formula 4)
(1197) In the organic EL device according to the exemplary embodiment, when the second dopant material and the second host material satisfy the relationship of the numerical formula (Numerical formula 4), due to the singlet energy of the second dopant material being lower than the singlet energy of the second host material, singlet excitons generated by the TTF phenomenon energy-transfer from the second host material to the second dopant material, thereby contributing to fluorescence of the second dopant material.
(1198) In the organic EL device of the exemplary embodiment, it is preferable that the second dopant material is a compound not having an azine ring structure in a molecule.
(1199) In the organic EL device of the exemplary embodiment, the second dopant material is preferably not a boron-containing complex, more preferably not a complex.
(1200) In the organic EL device of the exemplary embodiment, it is preferable that the second emitting layer does not contain a metal complex. Further, in the organic EL device of the exemplary embodiment, it is also preferable that the second emitting layer does not contain a boron-containing complex.
(1201) In the organic EL device of the exemplary embodiment, it is preferable that the second emitting layer does not contain a phosphorescent material (dopant material).
(1202) Further, it is preferable that the second emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of the heavy-metal complex herein include iridium complex, osmium complex, and platinum complex.
(1203) In the organic EL device of the exemplary embodiment, the second dopant material is preferably contained at more than 1.1 mass % in the second emitting layer. That is, the second emitting layer preferably contains the second dopant material at more than 1.1 mass % with respect to a total mass of the second emitting layer, more preferably at more than 1.2 mass % with respect to the total mass of the second emitting layer, further preferably at more than 1.5 mass % with respect to the total mass of the second emitting layer.
(1204) The second emitting layer preferably contains the second dopant material at 10 mass % or less with respect to the total mass of the second emitting layer, more preferably at 7 mass % or less with respect to the total mass of the second emitting layer, further preferably at 5 mass % or less with respect to the total mass of the second emitting layer.
(1205) The second emitting layer preferably contains a second compound as the second host material at 60 mass % or more with respect to the total mass of the second emitting layer, more preferably at 70 mass % or more with respect to the total mass of the second emitting layer, further preferably at 80 mass % or more with respect to the total mass of the second emitting layer, further more preferably at 90 mass % or more with respect to the total mass of the second emitting layer, still further preferably at 95 mass % or more with respect to the total mass of the second emitting layer.
(1206) The second emitting layer preferably contains the second host material at 99 mass % or less with respect to the total mass of the second emitting layer.
(1207) It should be noted that when the second emitting layer contains the second host material and the second dopant material, an upper limit of the total of the respective content ratios of the second host material and the second dopant material is 100 mass %.
(1208) It is not excluded that the second emitting layer according to the exemplary embodiment further contains a material(s) other than the second host material and the second dopant material.
(1209) The second emitting layer may include a single type of the second host material or may include two or more types of the second host material. The second emitting layer may include a single type of the second dopant material or may include two or more types of the second dopant material.
(1210) In the organic EL device according to the exemplary embodiment, the film thickness of the second emitting layer is preferably 5 nm or more, more preferably 15 nm or more. When the film thickness of the second emitting layer is 5 nm or more, it is easy to inhibit triplet excitons having transferred from the first emitting layer to the second emitting layer from returning to the first emitting layer. Further, when the film thickness of the second emitting layer is 5 nm or more, triplet excitons can be sufficiently separated from the recombination portion on the first emitting layer.
(1211) In the organic EL device according to the exemplary embodiment, the film thickness of the second emitting layer is preferably 20 nm or less. When the film thickness of the second emitting layer is 20 nm or less, the density of the triplet excitons in the second emitting layer is improved to cause the TTF phenomenon more easily.
(1212) In the organic EL device according to the exemplary embodiment, the film thickness of the second emitting layer is preferably in a range from 5 nm to 20 nm.
(1213) In the organic EL device according to the exemplary embodiment, a triplet energy T.sub.1(DX) of the compound that is contained in the first emitting layer and emits light having a maximum peak wavelength of 500 nm or less or the compound that is contained in the second emitting layer and emits light having a maximum peak wavelength of 500 nm or less, the triplet energy T.sub.1(H1) of the first host material, and the triplet energy T.sub.1(H2) of the second host material preferably satisfy a relationship of a numerical formula (Numerical Formula 10) below.
2.6 eV>T.sub.1(DX)>T.sub.1(H1)>T.sub.1(H2) (Numerical Formula 10)
(1214) When the first emitting layer contains the first dopant material, the triplet energy T.sub.1(D1) of the first dopant material preferably satisfies a relationship of a numerical formula (Numerical Formula 10A) below.
2.6 eV>T.sub.1(D1)>T.sub.1(H1>T.sub.1(H2) (Numerical Formula 10A)
(1215) When the second emitting layer contains the second dopant material, the triplet energy T.sub.1(D2) of the second dopant material preferably satisfies a relationship of a numerical formula (Numerical Formula 10B) below.
2.6 eV>T.sub.1(D2)>T.sub.1(H1)>T.sub.1(H2) (Numerical Formula 10B)
(1216) In the organic EL device according to the exemplary embodiment, the triplet energy T.sub.1(DX) of the compound that is contained in the first emitting layer and emits light having a maximum peak wavelength of 500 nm or less or the compound that is contained in the second emitting layer and emits light having a maximum peak wavelength of 500 nm or less and the triplet energy T.sub.1(H1) of the first host material preferably satisfy a relationship of a numerical formula (Numerical Formula 11) below.
0 eV<T.sub.1(DX)−T.sub.1(H1)<0.6 eV (Numerical Formula 11)
(1217) When the first emitting layer contains the first dopant material, the triplet energy T.sub.1(D1) of the first dopant material preferably satisfies a relationship of a numerical formula (Numerical Formula 11A) below.
0 eV<T.sub.1(D1)−T.sub.1(H1)<0.6 eV (Numerical Formula 11A)
(1218) When the second emitting layer contains the second dopant material, the triplet energy T.sub.1(D2) of the second dopant material preferably satisfies a relationship of a numerical formula (Numerical Formula 11B) below.
0 eV<T.sub.1(D2)−T.sub.1(H2)<0.8 eV (Numerical Formula 11B)
(1219) In the organic EL device according to the present exemplary embodiment, the triplet energy T.sub.1(H1) of the first host material preferably satisfies a relationship of a numerical formula (Numerical Formula 12) below.
T.sub.1(H1)>2.0 eV (Numerical Formula 12)
(1220) In the organic EL device according to the present exemplary embodiment, the triplet energy T.sub.1(H1) of the first host material also preferably satisfies a relationship of a numerical formula (Numerical Formula 12A) below, or also preferably satisfies a relationship of a numerical formula (Numerical Formula 12B) below.
T.sub.1(H1)>2.10 eV (Numerical Formula 12A)
T.sub.1(H1)>2.15 eV (Numerical Formula 12B)
(1221) In the organic EL device according to the present exemplary embodiment, when the triplet energy T.sub.1(H1) of the first host material satisfies the relationship of the numerical formula (Numerical Formula 12A) or the numerical formula (Numerical Formula 12B), triplet excitons generated in the first emitting layer are easily transferred to the second emitting layer, and also easily inhibited from back-transferring from the second emitting layer to the first emitting layer. Consequently, singlet excitons are efficiently generated, thereby improving luminous efficiency.
(1222) In the organic EL device according to the present exemplary embodiment, the triplet energy T.sub.1(H1) of the first host material also preferably satisfies a relationship of a numerical formula (Numerical Formula 12C) below, or also preferably satisfies a relationship of a numerical formula (Numerical Formula 12D) below.
2.08 eV>T.sub.1(H1)>1.87 eV (Numerical Formula 12C)
2.05 eV>T.sub.1(H1)>1.90 eV (Numerical Formula 12D)
(1223) In the organic EL device according to the present exemplary embodiment, when the triplet energy T.sub.1(H1) of the first host material satisfies the relationship of the numerical formula (Numerical Formula 12C) or the numerical formula (Numerical Formula 12D), energy of the triplet excitons generated in the first emitting layer is reduced, so that the organic EL device is expected to have a longer lifetime.
(1224) In the organic EL device according to the exemplary embodiment, a triplet energy T.sub.1(F1) of the compound that is contained in the first emitting layer and emits light having a maximum peak wavelength of 500 nm or less also preferably satisfies a relationship of a numerical formula (Numerical Formula 14A) below, or also preferably satisfies a relationship of a numerical formula (Numerical Formula 14B) below.
2.60 eV>T.sub.1(F1) (Numerical Formula 14A)
2.50 eV>T.sub.1(F1) (Numerical Formula 14B)
(1225) The organic EL device has a longer lifetime by containing the compound that satisfies the numerical formula (Numerical Formula 14A) or the numerical formula (Numerical Formula 14B) in the first emitting layer.
(1226) In the organic EL device according to the exemplary embodiment, a triplet energy T.sub.1(F2) of the compound that is contained in the second emitting layer and emits light having a maximum peak wavelength of 500 nm or less also preferably satisfies a relationship of a numerical formula (Numerical Formula 14C) below, or also preferably satisfies a relationship of a numerical formula (Numerical Formula 14D) below.
2.60 eV>T.sub.1(F2) (Numerical Formula 14C)
2.50 eV>T.sub.1(F2) (Numerical Formula 14D)
(1227) The second emitting layer contains the compound that satisfies the relationship of the numerical formula (Numerical Formula 14C) or the numerical formula (Numerical Formula 14D), so that the organic EL device has a longer lifetime.
(1228) In the organic EL device according to the present exemplary embodiment, the triplet energy T.sub.1(H2) of the second host material preferably satisfies a relationship of a numerical formula (Numerical Formula 13) below.
T.sub.1(H2)>1.9 eV (Numerical Formula 13)
(1229) In the organic EL device of the exemplary embodiment, the first emitting layer and the second emitting layer are preferably in direct contact with each other.
(1230) Herein, a layer arrangement that “the first emitting layer and the second emitting layer are in direct contact with each other” can include one of embodiments (LS1), (LS2), and (LS3) below.
(1231) (LS1) An embodiment in which a region containing both the first host material and the second host material is generated in a process of vapor-depositing the compound of the first emitting layer and vapor-depositing the compound of the second emitting layer, and is present on the interface between the first emitting layer and the second emitting layer.
(1232) (LS2) An embodiment in which in a case of containing an emitting compound in the first emitting layer and the second emitting layer, a region containing all of the first host material, the second host material and the emitting compound is generated in a process of vapor-depositing the compound of the first emitting layer and vapor-depositing the compound of the second emitting layer, and is present on the interface between the first emitting layer and the second emitting layer.
(1233) (LS3) An embodiment in which in a case of containing an emitting compound in the first emitting layer and the second emitting layer, a region containing the emitting compound, a region containing the first host material or a region containing the second host material is generated in a process of vapor-depositing the compound of the first emitting layer and vapor-depositing the compound of the second emitting layer, and is present on the interface between the first emitting layer and the second emitting layer.
(1234) Third Emitting Layer
(1235) The organic EL device according to the exemplary embodiment may include a third emitting layer.
(1236) It is preferable that: the third emitting layer contains a third host material; the first host material, the second host material and the third host material are different from one another; the third emitting layer at least contains a compound that emits light having a maximum peak wavelength of 500 nm or less; the compound that emits light having the maximum peak wavelength of 500 nm or less and is contained in the first emitting layer, the compound that emits light having the maximum peak wavelength of 500 nm or less and is contained in the second emitting layer, and the compound that emits light having the maximum peak wavelength of 500 nm or less and is contained in the third emitting layer are the same or different; and the triplet energy T.sub.1(H1) of the first host material and a triplet energy T.sub.1(H3) of the third host material satisfy a relationship of a numerical formula (Numerical Formula 30A) below.
T.sub.1(H1)>T.sub.1(H3) (Numerical Formula 30A)
(1237) When the organic EL device according to the exemplary embodiment includes the third emitting layer, the triplet energy T.sub.1(H2) of the second host material and the triplet energy T.sub.1(H3) of the third host material preferably satisfy a relationship of a numerical formula (Numerical Formula 30B) below.
T.sub.1(H2)>T.sub.1(H3) (Numerical Formula 30B)
(1238) When the organic EL device according to the exemplary embodiment includes the third emitting layer, it is preferable that the first emitting layer and the second emitting layer are in direct contact with each other and the second emitting layer and the third emitting layer are in direct contact with each other.
(1239) Herein, a layer arrangement that the second emitting layer and the third emitting layer are in direct contact with each other can include one of embodiments (LS4), (LS5) and (LS6) below.
(1240) (LS4) An embodiment in which a region containing both the second host material and the third host material is generated in a process of vapor-depositing the compound of the second emitting layer and vapor-depositing the compound of the third emitting layer, and is present on the interface between the second emitting layer and the third emitting layer.
(1241) (LS5) An embodiment in which in a case of containing an emitting compound in the second emitting layer and the third emitting layer, a region containing all of the second host material, the third host material and the emitting compound is generated in a process of vapor-depositing the compound of the second emitting layer and vapor-depositing the compound of the third emitting layer, and is present on the interface between the second emitting layer and the third emitting layer.
(1242) (LS6) An embodiment in which in a case of containing an emitting compound in the second emitting layer and the third emitting layer, a region containing the emitting compound, a region containing the second host material or a region containing the third host material is generated in a process of vapor-depositing the compound of the second emitting layer and vapor-depositing the compound of the third emitting layer, and is present on the interface between the second emitting layer and the third emitting layer.
(1243) It is also preferable that the organic EL device of the exemplary embodiment further includes a diffusion layer.
(1244) When the organic EL device of the exemplary embodiment includes the diffusion layer, it is preferable that the diffusion layer is interposed between the first emitting layer and the second emitting layer.
(1245) First Host Material, Second Host Material, and Third Host Material
(1246) In the organic EL device according to the exemplary embodiment, examples of the first host material, the second host material, and the third host material include the first compound represented by the formula (1), the first compound represented by a formula (1X), (12X), (13X), (14X), (15X), or (16X), and the second compound represented by the formula (2). Moreover, the first compound is usable as the first host material and the second host material. In this case, for descriptive purpose, the compound represented by the formula (1X), (12X), (13X), (14X), (15X), or (16X) used as the second host material is sometimes referred to as the second compound.
(1247) First Compound
(1248) Moreover, in the organic EL device of the second exemplary embodiment, the compound represented by the formula (1X), (12X), (13X), (14X), (15X), or (16X), in addition to the first compound described in the first exemplary embodiment, is also usable as the first compound.
(1249) Compound Represented by Formula (1X)
(1250) In the organic EL device of the exemplary embodiment, the first compound is also preferably represented by a formula (1X) below.
(1251) ##STR00521##
In the formula (1X):
(1252) R.sub.101 to R.sub.112 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by a formula (11X) above;
(1253) at least one of R.sub.101 to R.sub.112 is the group represented by the formula (11X);
(1254) when a plurality of groups represented by the formula (11X) are present, the plurality of groups represented by the formula (11X) are mutually the same or different;
(1255) L.sub.101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1256) Ar.sub.101 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1257) mx is 1, 2, 3, 4 or 5;
(1258) when two or more L.sub.111 are present, two or more L.sub.111 are mutually the same or different;
(1259) when two or more Ar.sub.101 are present, two or more Ar.sub.101 are mutually the same or different; and
(1260) * in the formula (11X) represents a bonding position to a benz[a]anthracene ring in the formula (1X).
(1261) In the organic EL device of the exemplary embodiment, the group represented by the formula (11X) is preferably a group represented by a formula (111X) below.
(1262) ##STR00522##
(1263) In the formula (111X):
(1264) X.sub.1 is CR.sub.143R.sub.144, an oxygen atom, a sulfur atom, or NR.sub.145;
(1265) L.sub.111 and L.sub.112 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1266) ma is 1, 2, 3, or 4;
(1267) mb is 1, 2, 3, or 4;
(1268) ma+mb is 2, 3, or 4;
(1269) Ar.sub.101 represents the same as Ar.sub.101 in the formula (11);
(1270) R.sub.141, R.sub.142, R.sub.143, R.sub.144 and R.sub.145 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1271) mc is 3;
(1272) three R.sub.141 are mutually the same or different;
(1273) md is 3; and
(1274) three R.sub.142 are mutually the same or different.
(1275) Among positions *1 to *8 of carbon atoms in a cyclic structure represented by a formula (111aX) below in the group represented by the formula (111X), L.sub.111 is bonded to one of the positions *1 to *4, R.sub.141 is bonded to each of three positions of the rest of *1 to *4, L.sub.112 is bonded to one of the positions *5 to *8, and R.sub.142 is bonded to each of three positions of the rest of *5 to *8.
(1276) ##STR00523##
(1277) For instance, in the group represented by the formula (111X), when L.sub.111 is bonded to a carbon atom at *2 in the cyclic structure represented by the formula (111 aX) and L.sub.112 is bonded to a carbon atom at *7 in the cyclic structure represented by the formula (111aX), the group represented by the formula (111X) is represented by a formula (111bX) below.
(1278) ##STR00524##
(1279) In the formula (111bX):
(1280) X.sub.1, L.sub.111, L.sub.112, ma, mb, Ar.sub.101, R.sub.141, R.sub.142, R.sub.143, R.sub.144 and R.sub.145 each independently represent X.sub.1, L.sub.111, L.sub.112, ma, mb, Ar.sub.101, R.sub.141, R.sub.142, R.sub.143, R.sub.144 and R.sub.145 in the formula (111X);
(1281) a plurality of R.sub.141 are mutually the same or different; and
(1282) a plurality of R.sub.142 are mutually the same or different.
(1283) In the organic EL device of the exemplary embodiment, the group represented by the formula (111X) is preferably the group represented by the formula (111bX).
(1284) In the compound represented by the formula (1X), it is preferable that ma is 1 or 2 and mb is 1 or 2.
(1285) In the compound represented by the formula (1X), it is preferable that ma is 1 and mb is 1.
(1286) In the compound represented by the formula (1X), Ar.sub.101 is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(1287) In the compound represented by the formula (1X), Ar.sub.101 is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benz[a]anthryl group; a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.
(1288) The compound represented by the formula (1X) is also preferably represented by a formula (101X) below.
(1289) ##STR00525##
(1290) In the formula (101X):
(1291) one of R.sub.111 and R.sub.112 represents a bonding position to L.sub.111 and one of R.sub.133 and R.sub.134 represents a bonding position to L.sub.101;
(1292) R.sub.111 or R.sub.112 that is not a bonding position to R.sub.101 to R.sub.110, R.sub.121 to R.sub.130, and L.sub.111, and R.sub.133 or R.sub.134 that is not a bonding position to L.sub.111 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1293) L.sub.101 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1294) mx is 1, 2, 3, 4 or 5; and
(1295) when two or more L.sub.111 are present, two or more L.sub.111 are mutually the same or different.
(1296) In the compound represented by the formula (1X), L.sub.111 is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
(1297) The compound represented by the formula (1X) is also preferably represented by a formula (102X) below.
(1298) ##STR00526##
(1299) In the formula (102X):
(1300) one of R.sub.111 and R.sub.112 represents a bonding position to L.sub.111 and one of R.sub.133 and R.sub.134 represents a bonding position to L.sub.112;
(1301) R.sub.111 or R.sub.112 that is not a bonding position to R.sub.101 to R.sub.110, R.sub.121 to R.sub.130, and L.sub.111, and R.sub.133 or R.sub.134 that is not a bonding position to R.sub.111 or R.sub.112 and L.sub.112 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1302) X.sub.1 is CR.sub.143R.sub.144, an oxygen atom, a sulfur atom, or NR.sub.145;
(1303) L.sub.111 and L.sub.112 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
(1304) ma is 1, 2, 3, or 4;
(1305) mb is 1, 2, 3, or 4;
(1306) ma+mb is 2, 3, 4, or 5;
(1307) R.sub.141, R.sub.142, R.sub.143, R.sub.144, and R.sub.145 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1308) mc is 3;
(1309) three R.sub.141 are mutually the same or different;
(1310) md is 3; and
(1311) three R.sub.142 are mutually the same or different.
(1312) In the compound represented by the formula (1X), it is preferable that ma is 1 or 2 and mb is 1 or 2 in the formula (102X).
(1313) In the compound represented by the formula (1X), it is preferable that ma is 1 and mb is 1 in the formula (102X).
(1314) In the compound represented by the formula (1X), the group represented by the formula (11X) is also preferably a group represented by a formula (11AX) or a group represented by a formula (11BX).
(1315) ##STR00527##
(1316) In the formulae (11AX) and (11BX):
(1317) R.sub.121 to R.sub.131 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
(1318) when a plurality of groups represented by the formula (11AX) are present, the plurality of groups represented by the formula (11AX) are mutually the same or different;
(1319) when a plurality of groups represented by the formula (11BX) are present, the plurality of groups represented by the formula (11BX) are mutually the same or different;
(1320) L.sub.131 and L.sub.132 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; and
(1321) * in each of the formulae (11AX) and (11BX) represents a bonding position to a benz[a]anthracene ring in the formula (1X).
(1322) The compound represented by the formula (1X) is also preferably represented by a formula (103X).
(1323) ##STR00528##
(1324) In the formula (103X):
(1325) R.sub.101 to R.sub.110 and R.sub.112 respectively represent the same as R.sub.101 to R.sub.110 and R.sub.112 in the formula (1X); and
(1326) R.sub.121 to R.sub.131, L.sub.131, and L.sub.132 respectively represent the same as R.sub.121 to R.sub.131, L.sub.131, and L.sub.132 in the formula (11BX).
(1327) In the compound represented by the formula (1X), L.sub.131 is preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
(1328) In the compound represented by the formula (1X), L.sub.132 is preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms.
(1329) In the compound represented by the formula (1X), two or more of R.sub.101 to R.sub.112 are preferably the groups represented by the formula (11).
(1330) In the compound represented by the formula (1X), it is preferable that two or more of R.sub.101 to R.sub.112 are the groups represented by the formula (11X) and Ar.sub.101 in the formula (11X) is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
(1331) In the compound represented by the formula (1X), it is also preferable that Ar.sub.101 is not a substituted or unsubstituted benz[a]anthryl group,
(1332) L.sub.101 is not a substituted or unsubstituted benz[a]anthrylene group, and
(1333) a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms as R.sub.101 to R.sub.110 that are not the group represented by the formula (11X) is not a substituted or unsubstituted benz[a]anthryl group.
(1334) In the compound represented by the formula (1X), R.sub.101 to R.sub.112 that are not the group represented by the formula (11X) are each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(1335) In the compound represented by the formula (1X), R.sub.101 to R.sub.112 that are not the group represented by the formula (11X) are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms.
(1336) In the compound represented by the formula (1X), R.sub.101 to R.sub.112 that are not the group represented by the formula (11X) are each preferably a hydrogen atom.
(1337) Compound Represented by Formula (12X)
(1338) In the organic EL device of the exemplary embodiment, the first compound is also preferably the compound represented by the formula (12X).
(1339) ##STR00529##
(1340) In the formula (12X):
(1341) at least one combination of adjacent two or more of R.sub.1201 to R.sub.1210 are mutually bonded to form a substituted or unsubstituted monocyclic ring, or mutually bonded to form a substituted or unsubstituted fused ring;
(1342) R.sub.1201 to R.sub.1210 neither forming the substituted or unsubstituted monocyclic ring nor forming the substituted or unsubstituted fused ring each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or the group represented by the formula (121);
(1343) a substituent for substituting the substituted or unsubstituted monocyclic ring, a substituent for substituting the substituted or unsubstituted fused ring, and at least one of R.sub.1201 to R.sub.1210 are the group represented by the formula (121);
(1344) when a plurality of groups represented by the formula (121) are present, the plurality of groups represented by the formula (121) are mutually the same or different;
(1345) L.sub.1201 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1346) Ar.sub.1201 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1347) mx2 is 0, 1, 2, 3, 4, or 5;
(1348) when two or more L.sub.1201 are present, the two or more L.sub.1201 are mutually the same or different;
(1349) when two or more Ar.sub.1201 are present, the two or more Ar.sub.1201 are mutually the same or different; and
(1350) * in the formula (121) represents a bonding position to the ring represented by the formula (12X).
(1351) In the formula (12X), combinations of adjacent two of R.sub.1201 to R.sub.1210 refer to a combination of R.sub.1201 and R.sub.1202, a combination of R.sub.1202 and R.sub.1203, a combination of R.sub.1203 and R.sub.1204, a combination of R.sub.1204 and R.sub.1205, a combination of R.sub.1205 and R.sub.1206, a combination of R.sub.1207 and R.sub.1208, a combination of R.sub.1208 and R.sub.1209, and a combination of R.sub.1209 and R.sub.1210.
(1352) Compound Represented by Formula (13X)
(1353) In the organic EL device of the exemplary embodiment, the first compound is also preferably a compound represented by a formula (13X).
(1354) ##STR00530##
(1355) In the formula (13X):
(1356) R.sub.1301 to R.sub.1310 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (131);
(1357) at least one of R.sub.1301 to R.sub.1310 is the group represented by the formula (131);
(1358) when a plurality of groups represented by the formula (131) are present, the plurality of groups represented by the formula (131) are mutually the same or different;
(1359) L.sub.1301 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1360) Ar.sub.1301 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1361) mx3 is 0, 1, 2, 3, 4, or 5;
(1362) when two or more L.sub.1301 are present, the two or more L.sub.1301 are mutually the same or different;
(1363) when two or more Ar.sub.1301 are present, two or more Ar.sub.1301 are mutually the same or different; and
(1364) * in the formula (131) represents a bonding position to a fluoranthene ring represented by the formula (13X).
(1365) In the organic EL device of the exemplary embodiment, combinations of adjacent two or more of R.sub.1301 to R.sub.1310 that are not the group represented by the formula (131) are not bonded to each other. In the formula (13X), combinations of adjacent two of R.sub.1301 to R.sub.1310 refer to a combination of R.sub.1301 and R.sub.1302, a combination of R.sub.1302 and R.sub.1303, a combination of R.sub.1303 and R.sub.1304, a combination of R.sub.1304 and R.sub.1305, a combination of R.sub.1305 and R.sub.1306, a combination of R.sub.1307 and R.sub.1308, a combination of R.sub.1300 and R.sub.1309, and a combination of R.sub.1309 and R.sub.1310.
(1366) Compound Represented by Formula (14X)
(1367) In the organic EL device of the exemplary embodiment, the first compound is also preferably a compound represented by a formula (14X) below.
(1368) ##STR00531##
(1369) In the formula (14X):
(1370) R.sub.1401 to R.sub.1410 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (141);
(1371) at least one of R.sub.1401 to R.sub.1410 is the group represented by the formula (141);
(1372) when a plurality of groups represented by the formula (141) are present, the plurality of groups represented by the formula (141) are mutually the same or different;
(1373) L.sub.1401 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1374) Ar.sub.1401 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; mx4 is 0, 1, 2, 3, 4, or 5;
(1375) when two or more L.sub.1401 are present, the two or more L.sub.1401 are mutually the same or different;
(1376) when two or more Ar.sub.1401 are present, the two or more Ar.sub.1401 are mutually the same or different; and
(1377) * in the formula (141) represents a bonding position to the ring represented by the formula (14X).
(1378) Compound Represented by Formula (15X)
(1379) In the organic EL device of the exemplary embodiment, the first compound is also preferably a compound represented by a formula (15X) below.
(1380) ##STR00532##
(1381) In the formula (15X):
(1382) R.sub.1501 to R.sub.1514 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (151);
(1383) at least one of R.sub.1501 to R.sub.1514 is the group represented by the formula (151);
(1384) when a plurality of group represented by the formula (151) are present, the plurality of group represented by the formula (151) are mutually the same or different;
(1385) L.sub.1501 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1386) Ar.sub.1501 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
(1387) mx5 is 0, 1, 2, 3, 4, or 5;
(1388) when two or more L.sub.1501 are present, the two or more L.sub.1501 are mutually the same or different;
(1389) when two or more Ar.sub.1501 are present, the two or more Ar.sub.1501 are mutually the same or different; and
(1390) * in the formula (151) represents a bonding position to the ring represented by the formula (15X).
(1391) Compound Represented by Formula (16X)
(1392) In the organic EL device of the exemplary embodiment, the first compound is also preferably is a compound represented by a formula (16X) below.
(1393) ##STR00533##
(1394) In the formula (16X):
(1395) R.sub.1601 to R.sub.1614 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), a group represented by —O—(R.sub.904), a group represented by —S—(R.sub.905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R.sub.801, a group represented by —COOR.sub.802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (161);
(1396) at least one of R.sub.1601 to R.sub.1614 is the group represented by the formula (161);
(1397) when a plurality of group represented by the formula (161) are present, the plurality of group represented by the formula (161) are mutually the same or different;
(1398) L.sub.1601 is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
(1399) Ar.sub.1601 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; mx6 is 0, 1, 2, 3, 4, or 5;
(1400) when two or more L.sub.1601 are present, the two or more L.sub.1601 are mutually the same or different;
(1401) when two or more Ar.sub.1601 are present, the two or more Ar.sub.1601 are mutually the same or different; and
(1402) * in the formula (161) represents a bonding position to the ring represented by the formula (16X).
(1403) In the organic EL device of the exemplary embodiment, it is also preferable that the first host material has, in a molecule, a linking structure including a benzene ring and a naphthalene ring linked to each other with a single bond, in which the benzene ring and the naphthalene ring in the linking structure are each independently fused or not fused with a further monocyclic ring or fused ring, and the benzene ring and the naphthalene ring in the linking structure are further linked to each other by cross-linking at at least one site other than the single bond.
(1404) Since the first host material has the linking structure including such cross-linking, it can be expected to suppress deterioration in chromaticity of the organic EL device.
(1405) The first host material in the above case is only required to have a linking structure as the minimum unit in a molecule, the linking structure including a benzene ring and a naphthalene ring linked to each other with a single bond (referred to as a benzene-naphthalene linking structure in some cases), the linking structure being as represented by a formula (X1) or a formula (X2) below. The benzene ring may be fused with a further monocyclic ring or fused ring, and the naphthalene ring may be fused with a further monocyclic ring or fused ring. For example, also in a case where the first host material has, in a molecule, a linking structure including a naphthalene ring and a naphthalene ring linked to each other with a single bond (referred to as a naphthalene-naphthalene linking structure in some cases) and being as represented by a formula (X3), a formula (X4), or a formula (X5) below, the naphthalene-naphthalene linking structure is regarded as including the benzene-naphthalene linking structure since one of the naphthalene rings includes a benzene ring.
(1406) ##STR00534##
(1407) In the organic EL device according to the exemplary embodiment, the cross-linking also preferably includes a double bond. Specifically, the first host material also preferably has a structure in which the benzene ring and the naphthalene ring are further linked to each other at any other site than the single bond by the cross-linking structure including a double bond.
(1408) Assuming that the benzene ring and the naphthalene ring in the benzene-naphthalene linking structure are further linked to each other at at least one site other than the single bond by cross-linking, for example, a linking structure (fused ring) represented by a formula (X11) below is obtained in a case of the formula (X1), and a linking structure (fused ring) represented by a formula (X31) below is obtained in a case of the formula (X3).
(1409) Assuming that the benzene ring and the naphthalene ring in the benzene-naphthalene linking structure are further linked to each other at any other site than the single bond by crosslinking including a double bond, for example, a linking structure (fused ring) represented by a formula (X12) below is obtained in a case of the formula (X1), a linking structure (fused ring) represented by a formula (X21) or formula (X22) below is obtained in a case of the formula (X2), a linking structure (fused ring) represented by a formula (X41) below is obtained in a case of the formula (X4), and a linking structure (fused ring) represented by a formula (X51) below is obtained in a case of the formula (X5).
(1410) Assuming that the benzene ring and the naphthalene ring in the benzene-naphthalene linking structure are further linked to each other at at least one site other than the single bond by cross-linking including a hetero atom (e.g., an oxygen atom), for example, a linking structure (fused ring) represented by a formula (X13) below is obtained in a case of the formula (X1).
(1411) ##STR00535##
(1412) In the organic EL device according to the exemplary embodiment, it is also preferable that: the first host material has, in a molecule, a biphenyl structure in which a first benzene ring and a second benzene ring are linked to each other with a single bond; and the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by cross-linking at at least one site other than the single bond.
(1413) In the organic EL device according to the exemplary embodiment, it is also preferable that the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking at one site other than the single bond. Since the first host material has the biphenyl structure including such cross-linking, it can be expected to inhibit the deterioration in the chromaticity of the organic EL device.
(1414) In the organic EL device according to the exemplary embodiment, the cross-linking also preferably includes a double bond.
(1415) In the organic EL device according to the exemplary embodiment, it is also preferable that the cross-linking does not include a double bond.
(1416) It is also preferable that the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking in two sites other than the single bond.
(1417) In the organic EL device according to the exemplary embodiment, it is also preferable that the first benzene ring and the second benzene ring in the biphenyl structure are further linked to each other by the cross-linking in two sites other than the single bond and the cross-linking includes no double bond. Since the first host material has the biphenyl structure including such cross-linking, it can be expected to inhibit the deterioration in the chromaticity of the organic EL device.
(1418) For example, assuming that the first benzene ring and the second benzene ring in the biphenyl structure represented by a formula (BP1) below are further linked to each other by cross-linking at at least one site other than the single bond, the biphenyl structure is exemplified by linking structures (fused rings) represented by formulae (BP11) to (BP15) below.
(1419) ##STR00536##
(1420) The formula (BP11) represents a linking structure in which the first benzene ring and the second benzene ring are linked to each other at one site other than the single bond by cross-linking including no double bond.
(1421) The formula (BP12) represents a linking structure in which the first benzene ring and the second benzene ring are linked to each other at one site other than the single bond by cross-linking including a double bond.
(1422) The formula (BP13) represents a linking structure in which the first benzene ring and the second benzene ring are linked to each other at two sites other than the single bond by cross-linking including no double bond.
(1423) The formula (BP14) represents a linking structure in which the first benzene ring and the second benzene ring are linked to each other at one of two sites other than the single bond by cross-linking including no double bond while being linked to each other at the other of the two sites other than the single bond by cross-linking including a double bond.
(1424) The formula (BP15) represents a linking structure in which the first benzene ring and the second benzene ring are linked to each other at two sites other than the single bond by cross-linking including double bonds.
(1425) In the first compound and the second compound, it is preferable that all groups described as “substituted or unsubstituted” groups are “unsubstituted” groups.
(1426) Manufacturing Method of First Compound
(1427) The first compound that is usable in the organic EL device according to the exemplary embodiment can be manufactured by a known method. The first compound can also be manufactured based on a known method through a known alternative reaction using a known material(s) tailored for the target compound.
(1428) Specific Examples of First Compound
(1429) Specific examples of the first compound usable in the organic EL device according to the exemplary embodiment include the specific examples of the first compound described in the first exemplary embodiment and the following compounds. It should however be noted that the invention is not limited by the specific examples of the first compound.
(1430) A compound(s) included in the specific examples of the first compound shown below and falling within a definition range of the compound represented by the formula (1) according to the first exemplary embodiment is/are also usable in the organic EL device according to the first exemplary embodiment.
(1431) In the specific examples of the compound herein, D represents a deuterium atom, Me represents a methyl group, and tBu represents a tert-butyl group.
(1432) ##STR00537## ##STR00538## ##STR00539## ##STR00540## ##STR00541## ##STR00542## ##STR00543## ##STR00544## ##STR00545## ##STR00546## ##STR00547## ##STR00548## ##STR00549## ##STR00550## ##STR00551## ##STR00552## ##STR00553## ##STR00554## ##STR00555## ##STR00556## ##STR00557## ##STR00558## ##STR00559## ##STR00560## ##STR00561## ##STR00562## ##STR00563## ##STR00564## ##STR00565## ##STR00566## ##STR00567## ##STR00568## ##STR00569## ##STR00570## ##STR00571## ##STR00572## ##STR00573## ##STR00574## ##STR00575## ##STR00576## ##STR00577## ##STR00578## ##STR00579## ##STR00580## ##STR00581## ##STR00582## ##STR00583## ##STR00584## ##STR00585## ##STR00586## ##STR00587## ##STR00588## ##STR00589## ##STR00590## ##STR00591## ##STR00592## ##STR00593## ##STR00594## ##STR00595## ##STR00596## ##STR00597## ##STR00598## ##STR00599## ##STR00600## ##STR00601## ##STR00602## ##STR00603## ##STR00604## ##STR00605## ##STR00606## ##STR00607## ##STR00608## ##STR00609## ##STR00610## ##STR00611## ##STR00612## ##STR00613## ##STR00614## ##STR00615## ##STR00616## ##STR00617## ##STR00618## ##STR00619## ##STR00620## ##STR00621## ##STR00622## ##STR00623## ##STR00624## ##STR00625## ##STR00626## ##STR00627## ##STR00628## ##STR00629## ##STR00630## ##STR00631## ##STR00632## ##STR00633## ##STR00634## ##STR00635## ##STR00636## ##STR00637## ##STR00638## ##STR00639## ##STR00640## ##STR00641## ##STR00642## ##STR00643## ##STR00644## ##STR00645## ##STR00646## ##STR00647## ##STR00648## ##STR00649## ##STR00650## ##STR00651## ##STR00652## ##STR00653## ##STR00654## ##STR00655## ##STR00656## ##STR00657## ##STR00658## ##STR00659## ##STR00660## ##STR00661## ##STR00662## ##STR00663## ##STR00664## ##STR00665## ##STR00666## ##STR00667## ##STR00668## ##STR00669##
Second Compound
(1433) The second compound described in the first exemplary embodiment is usable also in the organic EL device according to the second exemplary embodiment.
(1434) In the organic EL device according to the second exemplary embodiment, R.sub.201 to R.sub.208 that are substituents on an anthracene skeleton in the second compound represented by the formula (2) are preferably hydrogen atoms in terms of preventing inhibition of intermolecular interaction to inhibit a decrease in electron mobility. However, R.sub.201 to R.sub.208 may be a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
(1435) Assuming that R.sub.201 to R.sub.208 each are a bulky substituent such as an alkyl group and a cycloalkyl group, intermolecular interaction may be inhibited to decrease the electron mobility of the second compound relative to that of the first host material, so that a relationship of pH2>pH1 shown by the numerical formula (Numerical Formula 6) may not be satisfied. When the second compound is used in the second emitting layer, it can be expected that satisfying the relationship of pH2>pH1 inhibits a decrease in a recombination ability between holes and electrons in the first emitting layer and a decrease in a luminous efficiency. It should be noted that as the substituent, namely, a haloalkyl group, alkenyl group, alkynyl group, group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), group represented by —O—(R.sub.904), group represented by —S—(R.sub.905), group represented by —N(R.sub.906)(R.sub.907), aralkyl group, group represented by —C(═O)R.sub.801, group represented by —COOR.sub.802, halogen atom, cyano group, and nitro group are likely to be bulky, and an alkyl group and cycloalkyl group are likely to be further bulky.
(1436) In the second compound represented by the formula (2), R.sub.201 to R.sub.208, which are the substituents on the anthracene skeleton, are each preferably not a bulky substituent and preferably not an alkyl group and cycloalkyl group. More preferably, R.sub.201 to R.sub.208 are not an alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), group represented by —O—(R.sub.904), group represented by —S—(R.sub.905), group represented by —N(R.sub.906)(R.sub.907), aralkyl group, group represented by —C(═O)R.sub.801, group represented by —COOR.sub.802, halogen atom, cyano group, and nitro group.
(1437) In the second compound, examples of a substituent for a “substituted or unsubstituted” group on R.sub.201 to R.sub.208 also preferably do not include the above-described substituent that is likely to be bulky, especially a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group. Since the examples of the substituent for the “substituted or unsubstituted” group on R.sub.201 to R.sub.208 do not include a substituted or unsubstituted alkyl group and a substituted or unsubstituted cycloalkyl group, inhibition of intermolecular interaction to be caused by presence of a bulky substituent such as an alkyl group and a cycloalkyl group can be prevented, thereby preventing a decrease in the electron mobility. Moreover, when the second compound described above is used in the second emitting layer, a decrease in a recombination ability between holes and electrons in the first emitting layer and a decrease in the luminous efficiency can be inhibited.
(1438) It is more preferably that R.sub.201 to R.sub.208, which are the substituents on the anthracene skeleton, are not bulky substituents, and R.sub.201 to R.sub.208 as substituents are unsubstituted. Assuming that R.sub.201 to R.sub.208, which are the substituents on the anthracene skeleton, are not bulky substituents and substituents are bonded to R.sub.201 to R.sub.208 which are the not-bulky substituents, the substituents bonded to R.sub.201 to R.sub.208 are also preferably not the bulky substituents; the substituents bonded to R.sub.201 to R.sub.208 serving as substituents are preferably not an alkyl group and cycloalkyl group, more preferably not an alkyl group, cycloalkyl group, haloalkyl group, alkenyl group, alkynyl group, group represented by —Si(R.sub.901)(R.sub.902)(R.sub.903), group represented by —O—(R.sub.904), group represented by —S—(R.sub.905), group represented by —N(R.sub.906)(R.sub.907), aralkyl group, group represented by —C(═O)R.sub.801, group represented by —COOR.sub.802, halogen atom, cyano group, and nitro group.
(1439) Manufacturing Method of Second Compound
(1440) The second compound that is usable in the organic EL device according to the second exemplary embodiment can be manufactured by a known method. The second compound can also be manufactured based on a known method through a known alternative reaction using a known material(s) tailored for the target compound.
(1441) Specific Examples of Second Compound
(1442) Specific examples of the second compound usable in the organic EL device according to the second exemplary embodiment include the specific examples of the second compound described in the first exemplary embodiment. It should however be noted that the invention is not limited by the specific examples of the second compound.
(1443) First Dopant Material, Second Dopant Material, and Third Dopant Material In the organic EL device according to the second exemplary embodiment, specific examples of the first, second, and third dopant materials include the sixth compound, the seventh compound, and the like described in the first exemplary embodiment.
(1444) According to the second exemplary embodiment, since the first electron transporting layer containing the third compound represented by the formula (3) is provided close to the cathode with respect to the first emitting layer and the second emitting layer, an organic electroluminescence device configured to emit light with a high luminous efficiency and a long lifetime can be provided.
Third Exemplary Embodiment
(1445) Electronic Device
(1446) An electronic device according to a third exemplary embodiment is installed with any one of the organic EL devices according to the above exemplary embodiments. Examples of the electronic device include a display device and a light-emitting unit. Examples of the display device include a display component (e.g., an organic EL panel module), TV, mobile phone, tablet and personal computer. Examples of the light-emitting unit include an illuminator and a vehicle light.
(1447) Modification of Embodiment(s)
(1448) The scope of the invention is not limited by the above-described exemplary embodiments but includes any modification and improvement as long as such modification and improvement are compatible with the invention.
(1449) For instance, only two emitting layers are not necessarily provided but three or more emitting layers may be provided in a laminate. When the organic EL device has three or more emitting layers, it is only required that at least two of the emitting layers satisfy the conditions described in the above exemplary embodiments. For instance, the rest of the emitting layers may be a fluorescent emitting layer or a phosphorescent emitting layer with use of emission caused by electron transfer from the triplet excited state directly to the ground state.
(1450) When the organic EL device includes a plurality of emitting layers, these emitting layers may be mutually adjacently provided, or may form a so-called tandem organic EL device, in which a plurality of emitting units are laminated via an intermediate layer.
(1451) For instance, a blocking layer may be provided adjacent to at least one of a side of the emitting layer close to the anode or a side of the emitting layer close to the cathode. The blocking layer is preferably provided in contact with the emitting layer to block at least any of holes, electrons, and excitons.
(1452) For instance, when the blocking layer is provided in contact with the side of the emitting layer close to the cathode, the blocking layer permits transport of electrons and blocks holes from reaching a layer provided closer to the cathode (e.g., the electron transporting layer) beyond the blocking layer. When the organic EL device includes the electron transporting layer, the blocking layer is preferably interposed between the emitting layer and the electron transporting layer.
(1453) When the blocking layer is provided in contact with the side of the emitting layer close to the anode, the blocking layer permits transport of holes and blocks electrons from reaching a layer provided closer to the anode (e.g., the hole transporting layer) beyond the blocking layer. When the organic EL device includes the hole transporting layer, the blocking layer is preferably interposed between the emitting layer and the hole transporting layer.
(1454) Alternatively, the blocking layer may be provided adjacent to the emitting layer so that excitation energy does not leak out from the emitting layer toward neighboring layer(s). The blocking layer blocks excitons generated in the emitting layer from being transferred to a layer(s) (e.g., the electron transporting layer and the hole transporting layer) closer to the electrode(s) beyond the blocking layer.
(1455) The emitting layer is preferably bonded with the blocking layer.
(1456) As another example of the organic EL device according to the first exemplary embodiment, the organic EL device includes the first compound described in the second exemplary embodiment in the first emitting layer.
(1457) Specific structure, shape and the like of the components in the invention may be designed in any manner as long as an object of the invention can be achieved.
EXAMPLES
(1458) The invention will be described in further detail with reference to Examples. It should be noted that the scope of the invention is by no means limited by Examples.
(1459) Compounds
(1460) Structures of a compound represented by a formula (1) and used for manufacturing organic EL devices in Examples 1 to 26 and 33 are shown below.
(1461) ##STR00670##
(1462) A structure of a compound represented by a formula (1X) and used for manufacturing an organic EL device in Example 27 is shown below.
(1463) ##STR00671##
(1464) A structure of a compound represented by a formula (12X) and used for manufacturing organic EL devices in Examples 28, 30 and 32 is shown below.
(1465) ##STR00672##
(1466) A structure of a compound represented by a formula (14X) and used for manufacturing organic EL devices in Examples 29 and 30 is shown below.
(1467) ##STR00673##
(1468) A structure of a compound represented by a formula (15X) and used for manufacturing organic EL devices in Examples 31 and 32 is shown below.
(1469) ##STR00674##
(1470) Structures of a compound represented by a formula (2) and used for manufacturing organic EL devices in Examples 1 to 33 are shown below.
(1471) ##STR00675##
(1472) Structures of a compound represented by a formula (3) and used for manufacturing organic EL devices in Examples 1 to 33 are shown below.
(1473) ##STR00676## ##STR00677## ##STR00678## ##STR00679## ##STR00680##
(1474) Structure of compounds used for manufacturing organic EL devices in Comparatives 1 to 3 are shown below.
(1475) ##STR00681##
(1476) Structures of other compounds used for manufacturing the organic EL devices in Examples 1 to 33 and Comparatives 1 to 3 are shown below.
(1477) ##STR00682## ##STR00683## ##STR00684## ##STR00685## ##STR00686## ##STR00687##
Manufacture of Organic EL Devices
(1478) Organic EL devices were manufactured and evaluated as follows.
Example 1
(1479) A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. A film thickness of the ITO transparent electrode was 130 nm.
(1480) The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, a compound HT3 and a compound pdope were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer. The ratios of the compound HT3 and the compound pdope in the hole injecting layer were 97 mass % and 3 mass %, respectively.
(1481) After the formation of the hole injecting layer, the compound HT3 was vapor-deposited to form an 80-nm-thick second hole transporting layer.
(1482) After the formation of the second hole transporting layer, a compound HT4 was vapor-deposited to form a 10-nm-thick first hole transporting layer.
(1483) A compound BH3 (host material) and a compound BD2 (dopant material) were co-deposited on the first hole transporting layer so that a ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
(1484) A compound BH4 (host material) and the compound BD2 (dopant material) were co-deposited on the first emitting layer so that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
(1485) A compound ET6 was vapor-deposited on the second emitting layer to form a 5-nm-thick electron transporting layer (also referred to as a hole blocking layer (HBL)).
(1486) A compound ET1 and a compound Liq were co-deposited on the electron transporting layer (HBL) to form a 20-nm-thick electron transporting layer (ET). The ratios of the compound ET1 and the compound Liq in the electron transporting layer (ET) were 50 mass % and 50 mass %, respectively. Liq is an abbreviation of (8-quinolinolato)lithium ((8-Quinolinolato)lithium).
(1487) LiF was vapor-deposited on the electron transporting layer (ET) to form a 1-nm-thick electron injecting layer.
(1488) Metal Al was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
(1489) A device arrangement of the organic EL device in Example 1 is roughly shown as follows.
(1490) ITO(130)/HT3:pdope(5,97%:3%)/HT3(80)/HT4(10)/BH3:BD2(5,98%:2%)/BH4:BD2(20,98%:2%)/ET6(5)/ET1:Liq(20,50%:50%)/LiF(1)/Al(80)
(1491) Numerals in parentheses represent a film thickness (unit: nm).
(1492) The numerals (97%:3%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound HT3 and the compound pdope in the hole injecting layer, the numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH3 or BH4) and the dopant material (compound BD2) in the first emitting layer or the second emitting layer, and the numerals (50%:50%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound ET1 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
Examples 2 to 12
(1493) The organic EL devices in Examples 2 to 12 each were manufactured in the same manner as in Example 1 except that the electron transporting layer (ET) was formed by using a compound shown in Table 1 in place of the compound used for forming the electron transporting layer (ET) in Example 1.
Example 13
(1494) The organic EL device in Example 13 was manufactured in the same manner as in Example 1 except that a compound ET-A was vapor-deposited on the second emitting layer to form a 5-nm-thick electron transporting layer (also referred to as a hole blocking layer) (HBL), and the compound ET6 and the compound Liq were co-deposited to form a 20-nm-thick electron transporting layer (ET). In Example 13, the ratios of the compound ET6 and the compound Liq in the electron transporting layer (ET) were 50 mass % and 50 mass %, respectively.
(1495) Comparative 1
(1496) The organic EL device in Comparative 1 was manufactured in the same manner as in Example 1 except that a compound Ref-ET-B and the compound Liq were co-deposited on the second emitting layer in place of the electron transporting layer (HBL) and the electron transporting layer (ET) to form a 25-nm-thick electron transporting layer (ET). In Comparative 1, the ratios of the compound Ref-ET-B and the compound Liq in the electron transporting layer were 50 mass % and 50 mass %, respectively.
(1497) TABLE-US-00001 TABLE 1 HBL ET Film Film Life- thick- thick- time ness ness EQE LT90 Compound [nm] Compound [nm] [%] [hr] Example 1 ET6 — 5 ET1 Liq 20 9.0 100 Example 2 ET6 — 5 ET2 Liq 20 9.1 100 Example 3 ET6 — 5 ET4 Liq 20 8.9 100 Example 4 ET6 — 5 ET5 Liq 20 9.1 100 Example 5 ET6 — 5 ET8 Liq 20 9.0 100 Example 6 ET6 — 5 ET9 Liq 20 9.0 100 Example 7 ET6 — 5 ET11 Liq 20 8.5 150 Example 8 ET6 — 5 ET12 Liq 20 8.9 110 Example 9 ET6 — 5 ET15 Liq 20 9.0 100 Example 10 ET6 — 5 ET17 Liq 20 8.7 125 Example 11 ET6 — 5 ET18 Liq 20 8.4 155 Example 12 ET6 — 5 ET19 Liq 20 9.0 100 Comparative 1 — — — Ref- Liq 25 8.0 80 ET-B
(1498) TABLE-US-00002 TABLE 2 HBL ET Film Film Life- thick- thick- time ness ness EQE LT90 Compound [nm] Compound [nm] [%] [hr] Example 13 ET-A — 5 ET6 Liq 20 9.0 90 Comparative 1 — — 0 Ref- Liq 25 8.0 80 ET-B
Example 14
(1499) A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. A film thickness of the ITO transparent electrode was 130 nm.
(1500) The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, a compound HA1 was deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 5-nm-thick hole injecting layer.
(1501) After the formation of the hole injecting layer, the compound HT1 was vapor-deposited to form an 80-nm-thick second hole transporting layer.
(1502) After the formation of the second hole transporting layer, the compound HT2 was vapor-deposited to form a 10-nm-thick first hole transporting layer.
(1503) The compound BH1 (host material) and the compound BD1 (dopant material) were co-deposited on the first hole transporting layer so that a ratio of the compound BD1 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
(1504) The compound BH2 (host material) and the compound BD1 (dopant material) were co-deposited on the first emitting layer so that the ratio of the compound BD1 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
(1505) A compound ET3 was vapor-deposited on the second emitting layer to form a 10-nm-thick electron transporting layer (also referred to as a hole blocking layer (HBL)).
(1506) A compound Ref-ET-C was vapor-deposited on the electron transporting layer (HBL) to form a 15-nm-thick electron transporting layer (ET).
(1507) LiF was vapor-deposited on the electron transporting layer (ET) to form a 1-nm-thick electron injecting layer.
(1508) Metal aluminum (Al) was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
(1509) A device arrangement of the organic EL device in Example 14 is roughly shown as follows.
(1510) ITO(130)/HA1(5)/HT1(80)/HT2(10)/BH1:BD1(5,98%:2%)/BH2:BD1(20,98%:2%)/ET 3(10)/Ref-ET-C(15)/LiF(1)/Al(80)
(1511) Numerals in parentheses represent a film thickness (unit: nm).
(1512) The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1 or BH2) and the dopant material (compound BD1) in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
Examples 15 to 20 and 22 to 26
(1513) Organic EL devices in Examples 15 to 20 and 22 to 26 each were manufactured in the same manner as in Example 14 except that the electron transporting layer (HBL) was formed by using a compound shown in Table 3 in place of the compound used for forming the electron transporting layer (HBL) in Example 14.
Example 21
(1514) An organic EL device in Example 21 was manufactured in the same manner as in Example 14 except that a compound ET14 and a compound ET13 were co-deposited to form the electron transporting layer (HBL) in Example 14. In Example 21, the ratios of the compound ET14 and the compound ET13 in the electron transporting layer (HBL) were 50 mass % and 50 mass %, respectively.
(1515) Comparative 2
(1516) An organic EL device in Comparative 2 was manufactured in the same manner as in Example 14 except that a compound ET-A was vapor-deposited on the second emitting layer to form a 10-nm-electron transporting layer (HBL), and the electron transporting layer (ET) was formed on the electron transporting layer (HBL).
(1517) TABLE-US-00003 TABLE 3 HBL ET Film Film Life- thick- thick- time ness ness EQE LT90 Compound [nm] Compound [nm] [%] [hr] Example 14 ET3 10 Ref-ET-C 15 11.5 150 Example 15 ET4 10 Ref-ET-C 15 10.5 220 Example 16 ET5 10 Ref-ET-C 15 10.6 200 Example 17 ET6 10 Ref-ET-C 15 11.3 170 Example 18 ET7 10 Ref-ET-C 15 11.2 180 Example 19 ET10 10 Ref-ET-C 15 11.0 190 Example 20 ET14 10 Ref-ET-C 15 11.3 180 Example 21 ET14 10 Ref-ET-C 15 10.5 220 and ET13 Example 22 ET15 10 Ref-ET-C 15 10.9 190 Example 23 ET16 10 Ref-ET-C 15 11.5 160 Example 24 ET17 10 Ref-ET-C 15 10.6 210 Example 25 ET18 10 Ref-ET-C 15 10.7 180 Example 26 ET20 10 Ref-ET-C 15 10.5 210 Comparative 2 ET-A 10 Ref-ET-C 15 9.5 130
Example 27
(1518) A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. A film thickness of the ITO transparent electrode was 130 nm.
(1519) The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, a compound HT-C and the compound pdope were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer. The ratios of the compound HT-C and the compound pdope in the hole injecting layer were 90 mass % and 10 mass %, respectively.
(1520) After the formation of the hole injecting layer, the compound HT-C was vapor-deposited to form an 80-nm-thick second hole transporting layer.
(1521) After the formation of the second hole transporting layer, the compound HT4 was vapor-deposited to form a 10-nm-thick first hole transporting layer.
(1522) A compound BH1-1 (host material) and the compound BD2 (dopant material) were co-deposited on the first hole transporting layer so that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
(1523) A compound BH2-1 (host material) and the compound BD2 (dopant material) were co-deposited on the first emitting layer so that the ratio of the compound BD2 accounted for 2 mass %, thereby forming a 20-nm-thick second emitting layer.
(1524) The compound ET3 was vapor-deposited on the second emitting layer to form an 8-nm-thick electron transporting layer (also referred to as a hole blocking layer (HBL)).
(1525) The compound Ref-ET-C was vapor-deposited on the electron transporting layer (HBL) to form a 22-nm-thick electron transporting layer (ET).
(1526) LiF was vapor-deposited on the electron transporting layer (ET) to form a 1-nm-thick electron injecting layer.
(1527) Metal aluminum (Al) was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
(1528) A device arrangement of the organic EL device in Example 27 is roughly shown as follows.
(1529) ITO(130)/HT-C:pdope(10,90%:10%)/HT-C(80)/HT4(10)/BH1-1:BD2(5,98%:2%)/BH2-1:BD2(20,98%:2%)/ET3(8)/Ref-ET-C(22)/LiF(1)/Al(80)
(1530) Numerals in parentheses represent a film thickness (unit: nm).
(1531) The numerals (90%:10%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound HT-C and the compound pdope in the hole injecting layer. The numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-1 or BH2-1) and the dopant material (compound BD2) in the first emitting layer or the second emitting layer. Similar notations apply to the description below.
Examples 28 to 32
(1532) Organic EL devices in Examples 28 to 32 each were manufactured in the same manner as in Example 27 except that the electron transporting layer (HBL) was formed by using a compound shown in Table 4 in place of the compounds used for the first hole transporting layer, the first emitting layer, the second emitting layer, and the electron transporting layer (HBL).
(1533) Comparative 3
(1534) An organic EL device in Comparative 3 was manufactured in the same manner as in Example 31 except that the electron transporting layer (HBL) was formed by using a compound shown in Table 4 in place of the compound used for the electron transporting layer (HBL) in Example 31.
(1535) TABLE-US-00004 TABLE 4 First Hole HBL ET Transporting First Emitting Second Emitting Film Film Layer Layer Layer thickness thickness EQE LT90 Compound Compound Compound Compound [nm] Compound [nm] [%] [hr] Example 27 HT4 BH1-1 and BD2 BH2-1 and BD2 ET3 8 Ref-ET-C 22 9.8 150 Example 28 HT5 BH1-2 and BD2 BH2-1 and BD2 ET6 8 Ref-ET-C 22 9.7 180 Example 29 HT6 BH1-3 and BD2 BH2-1 and BD2 ET5 8 Ref-ET-C 22 10.3 100 Example 30 HT7 BH1-3 and BD2 BH1-2 and BD2 ET17 8 Ref-ET-C 22 9.5 220 Example 31 HT8 BH1-4 and BD2 BH2-1 and BD2 ET20 8 Ref-ET-C 22 10.3 90 Example 32 HT9 BH1-4 and BD2 BH1-2 and BD2 ET12 8 Ref-ET-C 22 10.1 95 Comparative 3 HT8 BH1-4 and BD2 BH2-1 and BD2 Ref-ET-B 8 Ref-ET-C 22 9.1 48
Example 33
(1536) A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. A film thickness of the ITO transparent electrode was 130 nm.
(1537) The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. Initially, a compound HT10 and the compound pdope were co-deposited on a surface provided with the transparent electrode line to cover the transparent electrode, thereby forming a 10-nm-thick hole injecting layer. The ratios of the compound HT10 and the compound pdope in the hole injecting layer were 90 mass % and 10 mass %, respectively.
(1538) After the formation of the hole injecting layer, the compound HT10 was vapor-deposited to form an 85-nm-thick second hole transporting layer.
(1539) After the formation of the second hole transporting layer, the compound HT9 was vapor-deposited to form a 5-nm-thick first hole transporting layer.
(1540) A compound BH1-5 (host material) and the compound BD3 (dopant material) were co-deposited on the first hole transporting layer so that the ratio of the compound BD3 accounted for 2 mass %, thereby forming a 5-nm-thick first emitting layer.
(1541) A compound BH2-2 (host material) and the compound BD3 (dopant material) were co-deposited on the first emitting layer so that the ratio of the compound BD3 accounted for 2 mass %, thereby forming a 15-nm-thick second emitting layer.
(1542) A compound ET6 was vapor-deposited on the second emitting layer to form a 5-nm-thick electron transporting layer (also referred to as a hole blocking layer (HBL)).
(1543) A compound ET2 and the compound Liq were co-deposited on the electron transporting layer (HBL) to form a 25-nm-thick electron transporting layer (ET). The ratios of the compound ET2 and the compound Liq in the electron transporting layer (ET) were 50 mass % and 50 mass %, respectively.
(1544) LiF was vapor-deposited on the electron transporting layer (ET) to form a 1-nm-thick electron injecting layer.
(1545) Metal aluminum (Al) was vapor-deposited on the electron injecting layer to form an 80-nm-thick cathode.
(1546) A device arrangement of the organic EL device in Example 33 is roughly shown as follows.
(1547) ITO(130)/HT10:pdope (10,90%:10%)/HT10(85)/HT9(5)/BH1-5:BD3 (5,98%:2%)/BH2-2:BD3 (15,98%:2%)/ET6(5)/ET2:Liq (25,50%:50%)/LiF(1)/Al(80)
(1548) Numerals in parentheses represent a film thickness (unit: nm).
(1549) The numerals (90%:10%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound HT10 and the compound pdope in the hole injecting layer, the numerals (98%:2%) represented by percentage in the same parentheses indicate a ratio (mass %) between the host material (compound BH1-5 or BH2-2) and the dopant material (compound BD3) in the first emitting layer or the second emitting layer, and the numerals (50%:50%) represented by percentage in the same parentheses indicate a ratio (mass %) between the compound ET2 and the compound Liq in the electron transporting layer (ET). Similar notations apply to the description below.
(1550) TABLE-US-00005 TABLE 5 First Hole HBL ET Transporting First Second Film Film Layer Emitting Layer Emitting Layer thickness thickness EQE LT90 Compound Compound Compound Compound [nm] Compound [nm] [%] [hr] Example 33 HT9 BH1-5 and BH2-2 and ET6 5 ET2 and Liq 25 10.9 106 BD3 BD3
Evaluation of Organic EL Devices
(1551) The organic EL devices manufactured in Examples 1 to 33 and Comparatives 1 to 3 were evaluated as follows. Evaluation results are shown in Tables 1, 2, 3, 4 and 5.
(1552) External Quantum Efficiency EQE
(1553) Voltage was applied on the organic EL devices so that a current density was 10 mA/cm.sup.2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
(1554) Lifetime (LT90)
(1555) Voltage was applied on the resultant organic EL devices so that a current density was 50 mA/cm.sup.2, where a time (LT90 (unit: hr)) elapsed before a luminance intensity was reduced to 90% of the initial luminance intensity was measured.
(1556) As shown in Tables 1, 2, 3, 4 and 5, the organic EL devices in Examples 1 to 33, in which the first electron transporting layer containing the third compound represented by the formula (3) was provided close to the cathode with respect to the first emitting layer and the second emitting layer, emitted light with a high luminous efficiency and a long lifetime.
(1557) Evaluation of Compounds
(1558) Preparation of Toluene Solution
(1559) The compound BD1 was dissolved in toluene at a concentration of 4.9×10.sup.−6 mol/L to prepare a toluene solution of the compound BD1.
(1560) A toluene solution of the compound BD2 was prepared in the same manner as the compound BD1.
(1561) A toluene solution of the compound BD3 was prepared in the same manner as the compound BD1.
(1562) Measurement of Maximum Fluorescence Peak Wavelength (FL-Peak)
(1563) Using a fluorescence spectrometer (spectrophotofluorometer F-7000 manufactured by Hitachi High-Tech Science Corporation), the toluene solution of the compound BD1, the toluene solution of the compound BD2, or the toluene solution of the compound BD3 was excited at 390 nm, where a maximum fluorescence peak wavelength was measured.
(1564) The maximum fluorescence peak wavelength of the compound BD1 was 453 nm.
(1565) The maximum fluorescence peak wavelength of the compound BD2 was 455 nm.
(1566) The maximum fluorescence peak wavelength of the compound BD3 was 444 nm.
(1567) Triplet Energy T.sub.1
(1568) A measurement target compound was dissolved in EPA (diethylether isopentane:ethanol=5:5:2 in volume ratio) at a concentration of 10 μmol/L, and the obtained solution was encapsulated in a quartz cell to provide a measurement sample. A phosphorescence spectrum (ordinate axis: phosphorescent luminous intensity, abscissa axis: wavelength) of the measurement sample was measured at a low temperature (77K). A tangent was drawn to the rise of the phosphorescence spectrum close to the short-wavelength region. An energy amount was calculated by a conversion equation (F1) below on a basis of a wavelength value λedge [nm] at an intersection of the tangent and the abscissa axis. The calculated energy amount was defined as triplet energy T.sub.1. It should be noted that the triplet energy T.sub.1 has an error of about plus or minus 0.02 eV depending on measurement conditions.
T.sub.1 [eV]=1239.85/λ.sub.edge Conversion Equation (F1)
(1569) The tangent to the rise of the phosphorescence spectrum close to the short-wavelength region is drawn as follows. While moving on a curve of the phosphorescence spectrum from the short-wavelength region to the local maximum value closest to the short-wavelength region among the local maximum values of the phosphorescence spectrum, a tangent is checked at each point on the curve toward the long-wavelength region of the phosphorescence spectrum. An inclination of the tangent is increased along the rise of the curve (i.e., a value of the ordinate axis is increased). A tangent drawn at a point of the local maximum inclination (i.e., a tangent at an inflection point) is defined as the tangent to the rise of the phosphorescence spectrum close to the short-wavelength region.
(1570) A local maximum point where a peak intensity is 15% or less of the maximum peak intensity of the spectrum is not counted in the above-mentioned local maximum peak intensity closest to the short-wavelength region. The tangent drawn at a point that is closest to the local maximum peak intensity closest to the short-wavelength region and where the inclination of the curve is the local maximum is defined as a tangent to the rise of the phosphorescence spectrum close to the short-wavelength region.
(1571) For phosphorescence measurement, a spectrophotofluorometer body F-4500 (manufactured by Hitachi High-Technologies Corporation) was used.
(1572) Singlet Energy S.sub.1
(1573) A toluene solution of a measurement target compound at a concentration of 10 μmol/L was prepared and put in a quartz cell. An absorption spectrum (ordinate axis: absorption intensity, abscissa axis: wavelength) of the thus-obtained sample was measured at a normal temperature (300K). A tangent was drawn to the fall of the absorption spectrum close to the long-wavelength region, and a wavelength value λedge (nm) at an intersection of the tangent and the abscissa axis was assigned to a conversion equation (F2) below to calculate the singlet energy.
S.sub.1 [eV]=1239.85/λ.sub.edge Conversion Equation (F2)
(1574) A spectrophotometer (U3310 manufactured by Hitachi, Ltd.) was used for measuring absorption spectrum.
(1575) The tangent to the fall of the absorption spectrum close to the long-wavelength region is drawn as follows. While moving on a curve of the absorption spectrum from the local maximum value closest to the long-wavelength region, among the local maximum values of the absorption spectrum, in a long-wavelength direction, a tangent at each point on the curve is checked. An inclination of the tangent is decreased and increased in a repeated manner as the curve falls (i.e., a value of the ordinate axis is decreased). A tangent drawn at a point where the inclination of the curve is the local minimum closest to the long-wavelength region (except when absorbance is 0.1 or less) is defined as the tangent to the fall of the absorption spectrum close to the long-wavelength region.
(1576) The maximum absorbance of 0.2 or less is not counted as the above-mentioned local maximum absorbance closest to the long-wavelength region.
(1577) Table 6 shows the singlet energy S.sub.1 and the triplet energy T.sub.1 of each compound.
(1578) TABLE-US-00006 TABLE 6 S.sub.1 [eV] T.sub.1 [eV] BH1 3.12 2.10 BH2 3.04 1.86 BH3 3.19 2.08 BH4 2.98 1.87 BH1-1 3.11 2.11 BH1-2 2.95 2.20 BH1-3 3.22 2.27 BH1-4 3.31 2.35 BH1-5 3.31 2.09 BH2-1 3.01 1.87 BH2-2 3.01 1.82 BD1 2.73 2.29 BD2 2.71 2.60 BD3 2.78 2.32