COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
20210061794 ยท 2021-03-04
Inventors
- Sohee Jo (Yongin-si, KR)
- Dongjun Kim (Yongin-si, KR)
- Minji Kim (Yongin-si, KR)
- Eunjae Jeong (Yongin-si, KR)
- Sanghyun Han (Yongin-si, KR)
Cpc classification
C07D409/12
CHEMISTRY; METALLURGY
C07D209/88
CHEMISTRY; METALLURGY
H10K85/6572
ELECTRICITY
H10K30/353
ELECTRICITY
H10K85/633
ELECTRICITY
H10K85/6574
ELECTRICITY
H10K85/636
ELECTRICITY
H10K85/615
ELECTRICITY
H10K85/6576
ELECTRICITY
International classification
C07D409/12
CHEMISTRY; METALLURGY
C07D209/88
CHEMISTRY; METALLURGY
C07D407/12
CHEMISTRY; METALLURGY
Abstract
A compound according to an embodiment of the present disclosure is represented by Formula 1:
##STR00001##
When the compound is used in an organic light-emitting device, efficiency is higher as compared to when existing compounds in the art are used. In particular, the compound shows a remarkable effect of lifespan improvement, resulting in a significantly increased lifespan of the organic light-emitting device including the compound.
Claims
1. A compound represented by Formula 1: ##STR00113## wherein, in Formula 1, L.sub.1 and L.sub.2 are each independently selected from a substituted or unsubstituted C.sub.6-C.sub.60 arylene group and a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group, a1 is an integer from 1 to 3, a2 is an integer from 0 to 2, Ar.sub.1, Ar.sub.2, and R.sub.1 to R.sub.4 are each independently selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.1)(Q.sub.2), C(O)(Q.sub.1), S(O).sub.2(Q.sub.1), and P(O)(Q.sub.1)(Q.sub.2), b1 is an integer from 0 to 4, b2 to b4 are each independently an integer from 0 to 5, at least one substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted, a C.sub.6-C.sub.60 arylene group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.1-C.sub.60 heteroarylene group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.11)(Q.sub.12), C(O)(Q.sub.11), S(O).sub.2(Q.sub.11), and P(O)(Q.sub.11)(Q.sub.12); a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.21)(Q.sub.22), C(O)(Q.sub.21), S(O).sub.2(Q.sub.21), and P(O)(Q.sub.21)(Q.sub.22); and B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and Q.sub.1, Q.sub.2, Q.sub.11, Q.sub.12, Q.sub.21, Q.sub.22, Q.sub.31, and Q.sub.32 are each independently selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
2. The compound of claim 1, wherein Ar.sub.1 and Ar.sub.2 in Formula 1 are each independently selected from a substituted or unsubstituted C.sub.6-C.sub.60 aryl group and a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group.
3. The compound of claim 1, wherein Ar.sub.1 is selected from groups represented by Formulae 2a to 2c: ##STR00114## wherein, in Formulae 2a to 2c, H.sub.1 is CR.sub.11, R.sub.12, O, and/or S, Z.sub.11 to Z.sub.14, R.sub.11, and R.sub.12 are each independently selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.1)(Q.sub.2), C(O)(Q.sub.1), S(O).sub.2(Q.sub.1), and P(O)(Q.sub.1)(Q.sub.2), wherein R.sub.11 and R.sub.12 are optionally linked to each other to form a ring, b11 is an integer from 1 to 5, b12 is an integer from 1 to 7, b13 is an integer from 1 to 3, b14 is an integer from 1 to 4, at least one substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is selected from: deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group; a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.11)(Q.sub.12), C(O)(Q.sub.11), S(O).sub.2(Q.sub.11), and P(O)(Q.sub.11)(Q.sub.12); a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.21)(Q.sub.22), C(O)(Q.sub.21), S(O).sub.2(Q.sub.21), and P(O)(Q.sub.21)(Q.sub.22); and B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), Q.sub.1, Q.sub.2, Q.sub.11, Q.sub.12, Q.sub.21, Q.sub.22, Q.sub.31, and Q.sub.32 are each independently selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and * indicates a binding site to a neighboring atom.
4. The compound of claim 3, wherein Z.sub.11 in Formula 2a is a substituted or unsubstituted C.sub.6-C.sub.60 aryl group.
5. The compound of claim 3, wherein Z.sub.11 in Formula 2a is selected from F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, and groups represented by Formulae 3a and 3b: ##STR00115## wherein, in Formulae 3a and 3b, Z.sub.21 and Z.sub.22 are each independently selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, and a phenanthrolinyl group, b21 is an integer from 1 to 5, b22 is an integer from 1 to 7, and * indicates a binding site to a neighboring atom.
6. The compound of claim 1, wherein Ar.sub.2 in Formula 1 is a substituted or unsubstituted C.sub.6-C.sub.60 aryl group.
7. The compound of claim 1, wherein Ar.sub.2 in Formula 1 is a C.sub.6-C.sub.60 aryl group substituted with F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, and/or a hydrazone group.
8. The compound of claim 1, wherein L.sub.1 and L.sub.2 in Formula 1 are each independently a substituted or unsubstituted C.sub.6-C.sub.60 arylene group.
9. The compound of claim 1, wherein L.sub.1 and L.sub.2 in Formula 1 are each independently selected from: a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, and a ovalenylene group; and a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, and an ovalenylene group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolylene group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and Q.sub.31 and Q.sub.32 are each independently selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
10. The compound of claim 1, wherein Formula 1 is Formula 2: ##STR00116## wherein, in Formula 2, L.sub.1, L.sub.2, Ar.sub.1, R.sub.1 to R.sub.4, a1, a2, and b1 to b4 are the same as described in connection with Formula 1, R.sub.21 is the same as R.sub.1, and b21 is an integer from 1 to 5.
11. The compound of claim 1, wherein Formula 1 is Formula 3: ##STR00117## wherein, in Formula 3, L.sub.1, Ar.sub.1, Ar.sub.2, R.sub.1 to R.sub.4, a1, a2, and b1 to b4 are the same as described in connection with Formula 1.
12. The compound of claim 1, wherein Formula 1 is Formula 4: ##STR00118## wherein, in Formula 4, L.sub.2, Ar.sub.1, Ar.sub.2, R.sub.1 to R.sub.4, a2, and b1 to b4 are the same as described in connection with Formula 1, R.sub.5 and L.sub.1 are the same as R.sub.1 and L.sub.1, respectively, b5 is an integer from 1 to 4, and a1 is an integer from 0 to 2.
13. The compound of claim 1, wherein Formula 1 is Formula 5: ##STR00119## wherein, in Formula 5, L.sub.2, Ar.sub.1, R.sub.1 to R.sub.4, a2, and b1 to b4 are the same as described in connection with Formula 1, each of R.sub.5 and R.sub.21 is defined the same as R.sub.1, L.sub.1 is the same as L.sub.1, a1 is an integer from 0 to 2, b5 is an integer from 1 to 4, and b21 is an integer from 1 to 5.
14. The compound of claim 1, wherein the compound represented by Formula 1 is selected from Compounds 1 to 120: ##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##
15. An organic light-emitting device comprising: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode and comprising an emission layer, wherein the organic layer comprises the compound of claim 1.
16. The organic light-emitting device of claim 15, wherein the emission layer is a fluorescent emission layer.
17. The organic light-emitting device of claim 15, wherein the first electrode is an anode, the second electrode is a cathode, and the organic layer, which is between the first electrode and the second electrode and comprises the emission layer, comprises i) a hole transport region between the first electrode and the emission layer, the hole transport region comprising a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer, or any combination thereof, and ii) an electron transport region between the emission layer and the second electrode, the electron transport region comprising a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
18. The organic light-emitting device of claim 17, wherein the hole transport region comprises the compound of Formula 1.
19. The organic light-emitting device of claim 15, wherein the emission layer comprises a styrylamine compound.
20. An electronic apparatus comprising: a thin-film transistor; and the organic light-emitting device of claim 15, wherein the thin-film transistor comprises a source electrode, a drain electrode, an activation layer, and a gate electrode, and the first electrode of the organic light-emitting device is electrically connected with one of the source electrode and the drain electrode of the thin-film transistor.
Description
BRIEF DESCRIPTION OF THE DRAWINGS
[0026] The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:
[0027]
DETAILED DESCRIPTION
[0028] Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. As used herein, the term and/or includes any and all combinations of one or more of the associated listed items. Throughout the disclosure, the expression at least one of a, b or c indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof.
[0029] Expressions such as at least one of, one of, and selected from, when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. Further, the use of may when describing embodiments of the present invention may refer to one or more embodiments of the present invention.
[0030] An embodiment of the present disclosure provides a compound represented by Formula 1:
##STR00003##
[0031] In Formula 1,
[0032] L.sub.1 and L.sub.2 may each independently be selected a substituted or unsubstituted C.sub.6-C.sub.60 arylene group and a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group,
[0033] a1 may be an integer from 1 to 3,
[0034] a2 may be an integer from 0 to 2,
[0035] Ar.sub.1, Ar.sub.2, and R.sub.1 to R.sub.4 may each independently be selected hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.1)(Q.sub.2), C(O)(Q.sub.1), S(O).sub.2(Q.sub.1), and P(O)(Q.sub.1)(Q.sub.2),
[0036] b1 may be an integer from 0 to 4,
[0037] b2 to b4 may each independently be an integer 0 to 5,
[0038] at least one substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted, a C.sub.6-C.sub.60 arylene group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted C.sub.1-C.sub.60 heteroarylene group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0039] deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group;
[0040] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.11)(Q.sub.12), C(O)(Q.sub.11), S(O).sub.2(Q.sub.11), and P(O)(Q.sub.11)(Q.sub.12);
[0041] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
[0042] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.21)(Q.sub.22), C(O)(Q.sub.21), S(O).sub.2(Q.sub.21), and P(O)(Q.sub.21)(Q.sub.22); and
[0043] B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and
[0044] Q.sub.1, Q.sub.2, Q.sub.11, Q.sub.12, Q.sub.21, Q.sub.22, Q.sub.31, and Q.sub.32 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0045] In the heteroaryl group and the heteroarylene group, a carbazolyl group and a carbazolylene group are excluded. For example, Formula 1 may include only one carbazole moiety.
[0046] Regarding the carbazole moiety in Formula 1 according to an embodiment, a benzene moiety (ring) not binding to L.sub.2 is in an unsubstituted state.
[0047] In one embodiment, Ar.sub.1 and Ar.sub.2 in Formula 1 may each independently be selected from a substituted or unsubstituted C.sub.6-C.sub.60 aryl group and a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group.
[0048] In one embodiment, Ar.sub.1 may be selected from Formulae 2a to 2c:
##STR00004##
[0049] In Formulae 2a to 2c,
[0050] H.sub.1 may be CR.sub.11R.sub.12, O, and/or S,
[0051] Z.sub.11 to Z.sub.14, R.sub.11, and R.sub.12 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.1)(Q.sub.2), C(O)(Q.sub.1), S(O).sub.2(Q.sub.1), and P(O)(Q.sub.1)(Q.sub.2), wherein R.sub.11 and R.sub.12 may be linked to each other to form a ring,
[0052] b11 may be an integer from 1 to 5, b12 may be an integer from 1 to 7, b13 may be an integer from 1 to 3, and b14 may be an integer from 1 to 4,
[0053] at least one substituent of the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0054] deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group;
[0055] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.11)(Q.sub.12), C(O)(Q.sub.11), S(O).sub.2(Q.sub.11), and P(O)(Q.sub.11)(Q.sub.12);
[0056] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
[0057] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, B(Q.sub.21)(Q.sub.22), C(O)(Q.sub.21), S(O).sub.2(Q.sub.21), and P(O)(Q.sub.21)(Q.sub.22); and
[0058] B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32),
[0059] Q.sub.1, Q.sub.2, Q.sub.11, Q.sub.12, Q.sub.21, Q.sub.22, Q.sub.31, and Q.sub.32 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
[0060] * indicates a binding site to a neighboring atom.
[0061] In one embodiment, Z.sub.11 in Formula 2a may be a substituted or unsubstituted C.sub.6-C.sub.60 aryl group.
[0062] In one embodiment, Z.sub.11 in Formula 2a may be selected from F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, and groups represented by Formulae 3a and 3b:
##STR00005##
[0063] In Formulae 3a and 3b,
[0064] Z.sub.21 and Z.sub.22 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triazinyl group, a benzimidazolyl group, and a phenanthrolinyl group,
[0065] b21 may be an integer from 1 to 5, b22 may be an integer from 1 to 7, and * indicates a binding site to a neighboring atom.
[0066] In one embodiment, Ar.sub.2 in Formula 1 may be a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, and for example, may be a C.sub.6-C.sub.60 aryl group substituted with F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, and/or a hydrazone group. For example, Ar.sub.2 in Formula 1 may be a C.sub.6-C.sub.60 aryl group substituted with F, Cl, Br, and/or I.
[0067] In one embodiment, L.sub.1 and L.sub.2 in Formula 1 may each independently be a substituted or unsubstituted C.sub.6-C.sub.60 arylene group. For example, L.sub.1 and L.sub.2 in Formula 1 may each independently be selected from: phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, and a ovalenylene group, and
[0068] a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, and an ovalenylene group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolylene group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and
[0069] Q.sub.31 and Q.sub.32 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.
[0070] In one embodiment, Formula 1 may be Formula 2:
##STR00006##
[0071] In Formula 2,
[0072] L.sub.1, L.sub.2, Ar.sub.1, R.sub.1 to R.sub.4, a1, a2, and b1 to b3 may each be understood by referring to the descriptions thereof provided in connection with Formula 1, R.sub.21 is same as R.sub.1, and b21 may be an integer from 1 to 5.
[0073] In one embodiment, Formula 1 may be Formula 3:
##STR00007##
[0074] In Formula 3,
[0075] L.sub.1, Ar.sub.1, Ar.sub.2, R.sub.1 to R.sub.4, a1, a2, and b1 to b4 may each be understood by referring to the descriptions thereof provided in connection with Formula 1.
[0076] In one embodiment, Formula 1 may be Formula 4:
##STR00008##
[0077] In Formula 4,
[0078] L.sub.2, Ar.sub.1, Ar.sub.2, R.sub.1 to R.sub.4, a2, and b1 to b4 may each be understood by referring to the descriptions thereof provided in connection with Formula 1, R.sub.5 and L.sub.1 are the same as R.sub.1 and L.sub.1, respectively, b5 may be an integer from 1 to 4, and a1 may be an integer from 0 to 2.
[0079] In one embodiment, Formula 1 may be Formula 5:
##STR00009##
[0080] In Formula 5,
[0081] L.sub.2, Ar.sub.1, R.sub.1 to R.sub.4, a2, and b1 to b4 may each be understood by referring to the descriptions thereof provided in connection with Formula 1, each of R.sub.5 and R.sub.21 is the same as R.sub.1, L.sub.1 is the same as L.sub.1, a1 may be an integer from 0 to 2, b5 may be an integer from 1 to 4, and b21 may be an integer from 1 to 5.
[0082] In one embodiment, the compound of Formula 1 may be one of compounds illustrated below:
##STR00010## ##STR00011## ##STR00012## ##STR00013## ##STR00014## ##STR00015## ##STR00016## ##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040## ##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045## ##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051##
[0083] The expression (an organic layer) includes at least one compound as used herein may include a case in which (an organic layer) includes one or more identical compounds represented by Formula 1 and a case in which (an organic layer) includes two or more different compounds represented by Formula 1.
[0084] For example, an organic layer may include, as the compound of Formula 1, only Compound 1. Here, Compound 1 may exist (e.g., may be included) only in an emission layer of an organic light-emitting device. In one or more embodiments, an organic layer may include, as the compound of Formula 1, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may exist in an identical (same) layer (for example, Compound 1 and Compound 2 may both exist in an emission layer), or in different layers (for example, Compound 1 may exist in an emission layer and Compound 2 may exist in an electron transport region).
[0085] Another embodiment of the present disclosure provides an organic light-emitting device including:
[0086] a first electrode;
[0087] a second electrode facing the first electrode;
[0088] an organic layer between the first electrode and the second electrode and including an emission layer; and
[0089] the compound of Formula 1
[0090] In one embodiment,
[0091] the first electrode of the organic light-emitting device may be an anode,
[0092] the second electrode of the organic light-emitting device may be a cathode, and
[0093] the organic layer may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode,
[0094] wherein the hole transport region may include a hole injection layer, a hole transport layer, a buffer layer, an electron blocking layer, or any combination thereof, and
[0095] the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0096] In one embodiment, the emission layer may be a fluorescence emission layer. For example, the emission layer may be a blue fluorescence emission layer.
[0097] In one embodiment, the compound of Formula 1 may be used in a hole transport region, for example, in a hole transport layer.
[0098] Another embodiment of the present disclosure provides an electronic apparatus including: a thin-film transistor; and the organic light-emitting device, wherein the thin-film transistor includes a source electrode, a drain electrode, an activation layer, and a gate electrode, and the first electrode of the organic light-emitting device is in electrical connection with at least one of the source electrode and the drain electrode of the thin-film transistor.
[0099] The term an organic layer as used herein may refer to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of an organic light-emitting device. A material included in the organic layer is not limited to an organic material.
Description of FIG. 1
[0100]
[0101] Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10 will be described in connection with
First Electrode 110
[0102] In
[0103] The first electrode 110 may be formed by depositing or sputtering a material to form the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material to form the first electrode 110 may be selected from materials with a high work function to facilitate hole injection.
[0104] The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material to form a first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO.sub.2), zinc oxide (ZnO), and any combinations thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, a material to form the first electrode may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (AlLi), calcium (Ca), magnesium-indium (MgIn), magnesium-silver (MgAg), and any combinations thereof, but embodiments of the present disclosure are not limited thereto.
[0105] The first electrode 110 may have a single-layered structure, or a multi-layered structure including two or more layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
Organic Layer 150
[0106] The organic layer 150 may be disposed on the first electrode 110. The organic layer 150 may include an emission layer.
[0107] The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 190.
Hole Transport Region in Organic Layer 150
[0108] The hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
[0109] The hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer.
[0110] For example, the hole transport region may have a single-layered structure including a single layer including a plurality of different materials, or a multi-layered structure having a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein for each structure, constituting layers are sequentially stacked from the first electrode 110 in this stated order, but the structure of the hole transport region is not limited thereto.
[0111] The hole transport region may include the compound of Formula 1.
[0112] The hole transport region may further include, for example, in addition to the compound of Formula 1, a compound described below.
[0113] In one embodiment, the hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB(NPD), -NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4,4-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (PANI/CSA), and polyaniline/poly(4-styrenesulfonate) (PANI/PSS):
##STR00052## ##STR00053## ##STR00054##
[0114] A thickness of the hole transport region may be in a range of about 100 to about 10,000 , for example, about 100 to about 1,000 . When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 to about 9,000 , and for example, about 100 to about 1,000 , and the thickness of the hole transport layer may be in a range of about 50 to about 2,000 , and for example, about 100 to about 1500 . When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, satisfactory (or suitable) hole transporting characteristics may be obtained without a substantial increase in driving voltage.
[0115] The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block or reduce the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may each independently include any of the materials as described above.
p-Dopant
[0116] The hole transport region may further include, in addition to the materials described above, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
[0117] The charge-generation material may be, for example, a p-dopant.
[0118] In one embodiment, the p-dopant may have a lowest unoccupied molecular orbital (LUMO) energy level of 3.5 ev or less.
[0119] The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto.
[0120] In one embodiment, the p-dopant may include at least one selected from:
[0121] a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and/or 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);
[0122] a metal oxide, such as tungsten oxide and/or molybdenum oxide;
[0123] 1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and
[0124] a compound represented by Formula 221,
[0125] but embodiments of the present disclosure are not limited thereto:
##STR00055##
[0126] In Formula 221,
[0127] R.sub.221 to R.sub.223 may each independently be selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one selected from R.sub.221 to R.sub.223 may include at least one substituent selected from a cyano group, F, Cl, Br, I, a C.sub.1-C.sub.20 alkyl group substituted with F, a C.sub.1-C.sub.20 alkyl group substituted with Cl, a C.sub.1-C.sub.20 alkyl group substituted with Br, and a C.sub.1-C.sub.20 alkyl group substituted with I.
Emission Layer in Organic Layer 150
[0128] When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In one or more embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.
[0129] The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.
[0130] In the emission layer, an amount of the dopant may be in a range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
[0131] A thickness of the emission layer may be in a range of about 100 to about 1,000 , for example, about 200 to about 600 . When the thickness of the emission layer is within this range, excellent (or suitable) light-emission characteristics may be obtained without a substantial increase in driving voltage.
[0132] The emission layer may include a quantum dot.
Host in Emission Layer
[0133] In one or more embodiments, the host may include a compound represented by Formula 301 below.
[Ar.sub.301].sub.xb11-[(L.sub.301).sub.xb1-R.sub.301].sub.xb21.Formula 301
[0134] In Formula 301,
[0135] Ar.sub.301 may be a substituted or unsubstituted C.sub.4-C.sub.60 carbocyclic group and/or a substituted or unsubstituted C.sub.1-C.sub.60 heterocyclic group,
[0136] xb11 may be 1, 2, and/or 3,
[0137] L.sub.301 may be selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0138] xb1 may be an integer from 0 to 5,
[0139] R.sub.301 may be selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted C.sub.1-C.sub.60 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q.sub.301)(Q.sub.302)(Q.sub.303), N(Q.sub.301)(Q.sub.302), B(Q.sub.301)(Q.sub.302), C(O)(Q.sub.301), S(O).sub.2(Q.sub.301), and P(O)(Q.sub.301)(Q.sub.302),
[0140] xb21 may be an integer from 1 to 5, and
[0141] Q.sub.301 to Q.sub.303 may each independently be selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.
[0142] In one embodiment, Ar.sub.301 in Formula 301 may be selected from:
[0143] a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group; and
[0144] a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, and a dibenzothiophene group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and
[0145] Q.sub.31 to Q.sub.33 may each independently be selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.
[0146] When xb11 in Formula 301 is 2 or more, two or more Ar.sub.301(s) may be linked to each other via a single bond.
[0147] In one or more embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or Formula 301-2:
##STR00056##
[0148] In Formulae 301-1 and 301-2,
[0149] A.sub.301 to A.sub.304 may each independently be selected from a benzene, a naphthalene, a phenanthrene, a fluoranthene, a triphenylene, a pyrene, a chrysene, a pyridine, a pyrimidine, an indene, a fluorene, a spiro-bifluorene, a benzofluorene, a dibenzofluorene, an indole, a carbazole, benzocarbazole, dibenzocarbazole, a furan, a benzofuran, a dibenzofuran, a naphthofuran, a benzonaphthofuran, a dinaphthofuran, a thiophene, a benzothiophene, a dibenzothiophene, a naphthothiophene, a benzonaphthothiophene group, and a dinaphthothiophene group,
[0150] X.sub.301 may be O, S, and/or N-[(L.sub.304).sub.xb4-R.sub.304],
[0151] R.sub.311 to R.sub.314 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32),
[0152] xb22 and xb23 may each independently be 0, 1, or 2,
[0153] L.sub.301, xb1, R.sub.301, and Q.sub.31 to Q.sub.33 may each be understood by referring to the descriptions thereof provided herein,
[0154] L.sub.302 to L.sub.304 may each be understood by referring to the description provided in connection with L.sub.301,
[0155] xb2 to xb4 may each be understood by referring to the description provided in connection with xb1, and
[0156] R.sub.302 to R.sub.304 may each be understood by referring to the description provided in connection with R.sub.301.
[0157] For example, L.sub.301 to L.sub.304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
[0158] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; and
[0159] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and
[0160] Q.sub.31 to Q.sub.33 are the same as described above.
[0161] In one embodiment, R.sub.301 to R.sub.304 in Formulae 301, 301-1, and 301-2 may each independently be selected from:
[0162] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and
[0163] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and
[0164] Q.sub.31 to Q.sub.33 are the same as described above.
[0165] In one or more embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (for example, Compound H55), a Mg complex, and a Zn complex.
[0166] The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4-bis(N-carbazolyl)-1,1-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55, but embodiments of the present disclosure are not limited thereto:
##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066## ##STR00067## ##STR00068## ##STR00069##
Phosphorescent Dopant Included in Emission Layer in Organic Layer 150
[0167] The phosphorescent dopant may include an organometallic complex represented by Formula 401:
##STR00070##
[0168] In Formulae 401 and 402,
[0169] M may be selected from iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), and thulium (Tm),
[0170] L.sub.401 may be selected from ligands represented by Formula 402, and xc1 may be 1, 2, and/or 3, wherein, when xc1 is two or more, two or more L.sub.401(s) may be identical to or different from each other,
[0171] L.sub.402 may be an organic ligand, and xc2 may be an integer from 0 to 4, wherein, when xc2 is 2 or more, two or more L.sub.402(s) may be identical to or different from each other,
[0172] X.sub.401 to X.sub.404 may each independently be nitrogen and/or carbon,
[0173] X.sub.401 and X.sub.403 may be linked to each other via a single bond and/or a double bond, and X.sub.402 and X.sub.404 may be linked to each other via a single bond and/or a double bond,
[0174] A.sub.401 and A.sub.402 may each independently be selected from a C.sub.4-C.sub.60 carbocyclic group and a C.sub.1-C.sub.60 heterocyclic group,
[0175] X.sub.405 may be a single bond, *O*, *S*, *C(O)*, *N(Q.sub.411)-*, *C(Q.sub.411)(Q.sub.412)-*, *C(Q.sub.411)C(Q.sub.412)-*, *C(Q.sub.411)=*, and/or *C(Q.sub.411)=*, wherein Q.sub.411 and Q.sub.412 may each independently be hydrogen, deuterium, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and/or a naphthyl group,
[0176] X.sub.406 may be a single bond, O, and/or S,
[0177] R.sub.401 and R.sub.402 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C.sub.1-C.sub.20 alkyl group, a substituted or unsubstituted C.sub.1-C.sub.20 alkoxy group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q.sub.401)(Q.sub.402)(Q.sub.403), N(Q.sub.401)(Q.sub.402), B(Q.sub.401)(Q.sub.402), C(O)(Q.sub.401), S(O).sub.2(Q.sub.401), and P(O)(Q.sub.401)(Q.sub.402), wherein Q.sub.401 to Q.sub.403 may each independently be selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a C.sub.6-C.sub.20 aryl group, and a C.sub.1-C.sub.20 heteroaryl group,
[0178] xc11 and xc12 may each independently be an integer from 0 to 10, and
[0179] * and * in Formula 402 each indicate a binding site to M in Formula 401.
[0180] In one embodiment, A.sub.401 and A.sub.402 in Formula 402 may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.
[0181] In one or more embodiments, in Formula 402, i) X.sub.401 may be nitrogen, and X.sub.402 may be carbon, or ii) X.sub.401 and X.sub.402 may each be nitrogen at the same time.
[0182] In one or more embodiments, R.sub.401 and R.sub.402 in Formula 402 may each independently be selected from:
[0183] hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, and a C.sub.1-C.sub.20 alkoxy group;
[0184] a C.sub.1-C.sub.20 alkyl group and a C.sub.1-C.sub.20 alkoxy group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, and a norbornenyl group;
[0185] a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
[0186] a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and
[0187] Si(Q.sub.401)(Q.sub.402)(Q.sub.403), N(Q.sub.401)(Q.sub.402), B(Q.sub.401)(Q.sub.402), C(O)(Q.sub.401), S(O).sub.2(Q.sub.401), and P(O)(Q.sub.401)(Q.sub.402), and
[0188] Q.sub.401 to Q.sub.403 may each independently be selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but embodiments of the present disclosure are not limited thereto.
[0189] In one or more embodiments, when xc1 in Formula 401 is 2 or more, two A.sub.401(s) in two or more L.sub.401(s) may optionally be linked to each other via X.sub.407, which is a linking group, and/or two A.sub.402(s) in two or more L.sub.401(s) may optionally be linked to each other via X.sub.408, which is a linking group (see e.g., Compounds PD1 to PD4 and PD7). X.sub.407 and X.sub.408 may each independently be a single bond, *O*, *S*, *C(O)*, *N(Q.sub.413)-*, *C(Q.sub.413)(Q.sub.414)-*, and/or *C(Q.sub.413)C(Q.sub.414)-* (wherein Q.sub.413 and Q.sub.414 may each independently be hydrogen, deuterium, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and/or a naphthyl group), but are not limited thereto.
[0190] L.sub.402 in Formula 401 may be a monovalent, divalent, and/or trivalent organic ligand. For example, L.sub.402 may be selected from halogen, diketone (for example, acetylacetonate), carboxylic acid (for example, picolinate), C(O), isonitrile, CN, and phosphorus (for example, phosphine and/or phosphite), but embodiments of the present disclosure are not limited thereto.
[0191] In one or more embodiments, the phosphorescence dopant may be selected from, for example, Compounds PD1 to PD25, but embodiments of the present disclosure are not limited thereto:
##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075##
Fluorescent Dopant in Emission Layer
[0192] The fluorescent dopant may include an arylamine compound and/or a styrylamine compound.
[0193] The fluorescent dopant may include a compound represented by Formula 501:
##STR00076##
[0194] In Formula 501,
[0195] Ar.sub.501 may be a substituted or unsubstituted C.sub.4-C.sub.60 carbocyclic group and/or a substituted or unsubstituted C.sub.1-C.sub.60 heterocyclic group,
[0196] L.sub.501 to L.sub.503 may each independently be selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0197] xd1 to xd3 may each independently be an integer from 0 to 3,
[0198] R.sub.501 and R.sub.502 may each independently be selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and
[0199] xd4 may be an integer from 1 to 6.
[0200] In one embodiment, Ar.sub.501 in Formula 501 may be selected from:
[0201] a naphthalene group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, and an indenophenanthrene group; and
[0202] a naphthalene group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, and an indenophenanthrene group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0203] In one or more embodiments, L.sub.501 to L.sub.503 in Formula 501 may each independently be selected from:
[0204] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group; and
[0205] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.
[0206] In one or more embodiments, R.sub.501 and R.sub.502 in Formula 501 may each independently be selected from:
[0207] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; and
[0208] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, and Si(Q.sub.31)(Q.sub.32)(Q.sub.33), and
[0209] Q.sub.31 to Q.sub.33 may each independently be selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0210] In one or more embodiments, xd4 in Formula 501 may be 2, but embodiments of the present disclosure are not limited thereto.
[0211] For example, the fluorescent dopant may be selected from Compounds FD1 to FD22:
##STR00077## ##STR00078## ##STR00079## ##STR00080## ##STR00081##
[0212] In one or more embodiments, the fluorescent dopant may be selected from the following compounds, but embodiments of the present disclosure are not limited thereto:
##STR00082##
Quantum Dot in Emission Layer
[0213] The emission layer may include a quantum dot selected from a IV-VI group compound, a IV group element, and a IV group compound. The IV-VI group compound may be selected from: a binary compound selected from SnS, SnSe, SnTe, PbS, PbSe, PbTe, and any mixture thereof; a ternary compound selected from SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe, and any mixture thereof; and a quaternary compound selected from SnPbSSe, SnPbSeTe, SnPbSTe, and any mixture thereof. The IV group element may be selected from Si, Ge, and any mixture thereof. The IV group compound may be a binary compound selected from SiC, SiGe, and any mixture thereof.
[0214] The binary compound, the ternary compound, or the quaternary compound may each independently exist in particles at uniform concentration, or may exist in the same particle in a state in which a concentration distribution is partially different. In addition, the binary compound, the ternary compound, or the quaternary compound may each independently have a core-shell structure, in which one quantum dot surrounds another quantum dot. An interface between the core and the shell may have a concentration gradient in which the concentration of atoms existing in the shell decreases toward the center.
[0215] In one or more embodiments, the quantum dot may have a core-shell structure including a core with the above-described nanoparticles and a shell surrounding the core. The shell of the quantum dot may serve as a protective layer for maintaining semiconductor characteristics by preventing or reducing chemical degeneration of the core, and/or may serve as a charging layer for imparting electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multilayer. An interface between the core and the shell may have a concentration gradient in which the concentration of atoms existing in the shell decreases toward the center. Examples of the shell of the quantum dot may include a metal oxide, a non-metal oxide, a semiconductor compound, and combinations thereof.
[0216] For example, examples of the metal oxide and non-metal oxide may include a binary compound (such as SiO.sub.2, Al.sub.2O.sub.3, TiO.sub.2, ZnO, MnO, Mn.sub.2O.sub.3, Mn.sub.3O.sub.4, CuO, FeO, Fe.sub.2O.sub.3, Fe.sub.3O.sub.4, CoO, Co.sub.3O.sub.4, and/or NiO), and a ternary compound (such as MgAl.sub.2O.sub.4, CoFe.sub.2O.sub.4, NiFe.sub.2O.sub.4, and/or CoMn.sub.2O.sub.4), but embodiments of the present disclosure are not limited thereto.
[0217] Examples of the semiconductor compound may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, and the like, but embodiments of the present disclosure are not limited thereto.
[0218] A full width of half maximum (FWHM) of an emission wavelength spectrum of the quantum dot may be about 45 nm or less, for example, about 40 nm or less, for example, about 30 nm or less. When the FWHM of the emission wavelength spectrum of the quantum dot is within this range, color purity and/or color reproduction may be improved.
[0219] In some embodiments, light emitted through such quantum dot is irradiated in omnidirection, thereby improving a wide viewing angle. More specifically, a spherical, pyramidal, multi-arm, and/or cubic nanoparticle, a nanotube, a nanowire, a nanofiber, and/or nanoplate particle may be used.
[0220] The quantum dot may adjust the color of emitted light according to the particle size. Therefore, the quantum dot may emit various emission colors such as blue, red, and/or green.
Electron Transport Region in Organic Layer 150
[0221] The electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
[0222] The electron transport region may include at least one selected from a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure are not limited thereto.
[0223] For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or an electron transport layer/electron injection layer structure, wherein for each structure, constituting layers are sequentially stacked from an emission layer. However, embodiments of the structure of the electron transport region are not limited thereto.
[0224] The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, and/or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one electron-depleted nitrogen-containing ring.
[0225] The electron-depleted nitrogen-containing ring may refer to a C.sub.1-C.sub.60 heterocyclic group having at least one *N* moiety as a ring-forming moiety.
[0226] For example, the electron-depleted nitrogen-containing ring may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *N* moiety, ii) a heteropolycyclic group in which two or more 5-membered to 7-membered heteromonocyclic groups, each having at least one *N* moiety, are condensed with each other, or iii) a heteropolycyclic group in which at least one of 5-membered to 7-membered heteromonocyclic groups, each having at least one *N* moiety, is condensed with at least one C.sub.5-C.sub.60 carbocyclic group.
[0227] Examples of the electron-depleted nitrogen-containing ring include an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a thiadiazole, an imidazopyridine, an imidazopyrimidine, and an azacarbazole, but are not limited thereto.
[0228] For example, the electron transport region may include a compound represented by Formula 601:
[Ar.sub.601].sub.xe11-[(L.sub.601).sub.xe1-R.sub.601].sub.xe21.Formula 601
[0229] In Formula 601,
[0230] Ar.sub.601 may be a substituted or unsubstituted C.sub.4-C.sub.60 carbocyclic group and/or a substituted or unsubstituted C.sub.1-C.sub.60 heterocyclic group,
[0231] xe11 may be 1, 2, and/or 3,
[0232] L.sub.601 may be selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkylene group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkylene group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenylene group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenylene group, a substituted or unsubstituted C.sub.6-C.sub.60 arylene group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
[0233] xe1 may be an integer from 0 to 5,
[0234] R.sub.601 may be selected from a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkyl group, a substituted or unsubstituted C.sub.3-C.sub.10 cycloalkenyl group, a substituted or unsubstituted C.sub.1-C.sub.10 heterocycloalkenyl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryl group, a substituted or unsubstituted C.sub.6-C.sub.60 aryloxy group, a substituted or unsubstituted C.sub.6-C.sub.60 arylthio group, a substituted or unsubstituted C.sub.1-C.sub.60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, Si(Q.sub.601)(Q.sub.602)(Q.sub.603), C(O)(Q.sub.601), S(O).sub.2(Q.sub.601), and P(O)(Q.sub.601)(Q.sub.602),
[0235] Q.sub.601 to Q.sub.603 may each independently be a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and/or a naphthyl group, and
[0236] xe21 may be an integer from 1 to 5.
[0237] In one embodiment, at least one of Ar.sub.601(s) in the number of xe11 and at least one of R.sub.601(s) in the number of xe21 may each independently include the electron-depleted nitrogen-containing ring.
[0238] In one embodiment, Ar.sub.601 in Formula 601 may be selected from:
[0239] a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and
[0240] a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, Si(Q.sub.31)(Q.sub.32)(Q.sub.33), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and
[0241] Q.sub.31 to Q.sub.33 may each independently be selected from a C.sub.1-C.sub.10 alkyl group, a C.sub.1-C.sub.10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0242] When xe11 in Formula 601 is 2 or more, two or more Ar.sub.601(s) may be linked to each other via a single bond.
[0243] In one or more embodiments, Ar.sub.601 in Formula 601 may be an anthracene group.
[0244] In one or more embodiments, a compound represented by Formula 601 may be represented by Formula 601-1:
##STR00083##
[0245] In Formula 601-1,
[0246] X.sub.614 may be N or C(R.sub.614), X.sub.615 may be N or C(R.sub.615), X.sub.616 may be N or C(R.sub.616), and at least one selected from X.sub.614 to X.sub.616 may be N,
[0247] L.sub.611 to L.sub.613 may each independently be the same as described in connection with L.sub.601,
[0248] xe611 to xe613 may each independently be defined the same as xe1,
[0249] R.sub.611 to R.sub.613 may each be understood by referring to the description provided in connection with R.sub.601, and
[0250] R.sub.614 to R.sub.616 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.
[0251] In one embodiment, L.sub.601 and L.sub.611 to L.sub.613 in Formulae 601 and 601-1 may each independently be selected from:
[0252] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group; and
[0253] a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group,
[0254] but embodiments of the present disclosure are not limited thereto.
[0255] In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, and/or 2.
[0256] In one or more embodiments, R.sub.601 and R.sub.611 to R.sub.613 in Formula 601 and 601-1 may each independently be selected from:
[0257] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;
[0258] a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and
[0259] S(O).sub.2(Q.sub.601) and P(O)(Q.sub.601)(Q.sub.602), and
[0260] Q.sub.601 and Q.sub.602 are the same as described above.
[0261] The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:
##STR00084## ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094##
[0262] In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-dphenyl-1,10-phenanthroline (Bphen), Alq3, BAlq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:
##STR00095##
[0263] In one embodiment, the electron transport region may include a phosphine oxide-containing compound (for example, TSPO1 used in the following examples and/or the like), but embodiments of the present disclosure are not limited thereto. In one embodiment, the phosphine oxide-containing compound may be used in a hole blocking layer in the electron transport region, but embodiments of the present disclosure are not limited thereto.
[0264] Thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 to about 1,000 , for example, about 30 to about 300 . When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within any of these ranges, the electron transport region may have excellent (or suitable) hole blocking characteristics and/or electron control characteristics without a substantial increase in driving voltage.
[0265] A thickness of the electron transport layer may be in a range of about 100 to about 1,000 , for example, about 150 to about 500 . When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory (or suitable) electron transport characteristics without a substantial increase in driving voltage.
[0266] The electron transport region (for example, the electron transport layer in the electron transport region) may further include, in addition to the materials described above, a metal-containing material.
[0267] The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth-metal complex. The alkali metal complex may include a metal ion selected from a Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex may include a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Sr ion, and a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0268] For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) and/or Compound ET-D2:
##STR00096##
[0269] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may be in direct contact with the second electrode 190.
[0270] The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.
[0271] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof.
[0272] The alkali metal may be selected from Li, Na, K, Rb, and Cs. In one embodiment, the alkali metal may be Li, Na, and/or Cs. In one or more embodiments, the alkali metal may be Li and/or Cs, but embodiments of the present disclosure are not limited thereto.
[0273] The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.
[0274] The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.
[0275] The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be selected from oxides and halides (for example, fluorides, chlorides, bromides, and/or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal, respectively.
[0276] The alkali metal compound may be selected from alkali metal oxides (such as Li.sub.2O, Cs.sub.2O, and/or K.sub.2O), and alkali metal halides (such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI). In one embodiment, the alkali metal compound may be selected from LiF, Li.sub.2O, NaF, LiI, NaI, CsI, and KI, but embodiments of the present disclosure are not limited thereto.
[0277] The alkaline earth-metal compound may be selected from alkaline earth-metal oxides, such as BaO, SrO, CaO, Ba.sub.xSr.sub.1-xO (0<x<1), and/or Ba.sub.xCa.sub.1-xO (0<x<1). In one embodiment, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but embodiments of the present disclosure are not limited thereto.
[0278] The rare earth metal compound may be selected from YbF.sub.3, ScF.sub.3, ScO.sub.3, Y.sub.2O.sub.3, Ce.sub.2O.sub.3, GdF.sub.3 and TbF.sub.3. In one embodiment, the rare earth metal compound may be selected from YbF.sub.3, ScF.sub.3, TbF.sub.3, YbI.sub.3, ScI.sub.3, and TbI.sub.3, but embodiments of the present disclosure are not limited thereto.
[0279] The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may respectively include an ion of alkali metal, alkaline earth-metal, and rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.
[0280] The electron injection layer may include (e.g., may consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal compound, the alkaline earth-metal compound, the rare earth metal compound, the alkali metal complex, the alkaline earth-metal complex, the rare earth metal complex, or any combinations thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.
[0281] A thickness of the electron injection layer may be in a range of about 1 to about 100 , for example, about 3 to about 90 . When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory (or suitable) electron injection characteristics without a substantial increase in driving voltage.
Second Electrode 190
[0282] The second electrode 190 may be disposed on the organic layer 150 having the structure according to embodiments of the present disclosure. The second electrode 190 may be a cathode, which is an electron injection electrode, and in this regard, a material to form the second electrode 190 may be selected from a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.
[0283] The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (AlLi), calcium (Ca), magnesium-indium (MgIn), magnesium-silver (MgAg), ITO, and IZO, but embodiments of the present disclosure are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.
[0284] The second electrode 190 may have a single-layered structure, or a multi-layered structure including two or more layers.
Description of FIGS. 2 to 4
[0285]
[0286] Regarding
[0287] In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in an emission layer may pass through the first electrode 110 and the first capping layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. In the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in an emission layer may pass through the second electrode 190 and the second capping layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.
[0288] The first capping layer 210 and the second capping layer 220 may increase external luminescent efficiency according to the principle of constructive interference.
[0289] The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material. The organic capping layer may include polyethylene tetephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acryl-based resin (e.g., polymethylmethacrylate, polyacrylic acid, etc), or any combination thereof.
[0290] At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrine derivatives, phthalocyanine derivatives, a naphthalocyanine derivatives, alkali metal complexes, and alkaline earth-based complexes. The carbocyclic compound, the heterocyclic compound, and/or the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In one embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine-based compound.
[0291] In one or more embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but embodiments of the present disclosure are not limited thereto.
##STR00097##
[0292] Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection with
[0293] Layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region may be formed in a certain region by using one or more suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.
[0294] When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100 C. to about 500 C., a vacuum degree of about 10.sup.8 torr to about 10.sup.3 torr, and a deposition speed of about 0.01 /sec to about 100 /sec, by taking into account a material to be included in a layer to be formed, and the structure of a layer to be formed.
[0295] When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80 C. to 200 C., by taking into account a material to be included in a layer to be formed, and the structure of a layer to be formed.
Apparatus
[0296] The organic light-emitting device may be included in various suitable apparatuses. For example, a light-emitting apparatus, an authentication apparatus, and/or an electronic apparatus, which includes the organic light-emitting device, may be provided.
[0297] The light-emitting apparatus may further include, in addition to the organic light-emitting device, a thin film transistor including a source electrode and a drain electrode. One of the source electrode and the drain electrode of the thin film transistor may be electrically connected to one of the first electrode and the second electrode of the organic light-emitting device. The light-emitting apparatus may be used as various suitable displays, light sources, and/or the like.
[0298] The authentication apparatus may be, for example, a biometric authentication apparatus for authenticating an individual by using biometric information of a biometric body (for example, a finger tip, a pupil, and/or the like).
[0299] The authentication apparatus may further include, in addition to the organic light-emitting device, a biometric information collector.
[0300] The electronic apparatus may be applied to personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram (ECG) displays, ultrasonic diagnostic devices, and/or endoscope displays), fish finders, various measuring instruments, meters (for example, meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like, but embodiments of the present disclosure are not limited thereto.
General Definition of Substituents
[0301] The term C.sub.1-C.sub.60 alkyl group as used herein may refer to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term C.sub.1-C.sub.60 alkylene group as used herein may refer to a divalent group having the same structure as the C.sub.1-C.sub.60 alkyl group.
[0302] The term C.sub.2-C.sub.60 alkenyl group as used herein may refer to a hydrocarbon group having at least one carbon-carbon double bond, for example, in the middle and/or at the terminus of the C.sub.2-C.sub.60 alkyl group, and non-limiting examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term C.sub.2-C.sub.60 alkenylene group as used herein may refer to a divalent group having the same structure as the C.sub.2-C.sub.60 alkenyl group.
[0303] The term C.sub.2-C.sub.60 alkynyl group as used herein may refer to a hydrocarbon group having at least one carbon-carbon triple bond, for example, in the middle and/or at the terminus of the C.sub.2-C.sub.60 alkyl group, and non-limiting examples thereof include an ethynyl group, and a propynyl group. The term C.sub.2-C.sub.60 alkynylene group as used herein may refer to a divalent group having the same structure as the C.sub.2-C.sub.60 alkynyl group.
[0304] The term C.sub.1-C.sub.60 alkoxy group as used herein may refer to a monovalent group represented by OA.sub.101 (wherein A.sub.101 is the C.sub.1-C.sub.60 alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.
[0305] The term C.sub.3-C.sub.10 cycloalkyl group as used herein may refer to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and non-limiting examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term C.sub.3-C.sub.10 cycloalkylene group as used herein may refer to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkyl group.
[0306] The term C.sub.1-C.sub.10 heterocycloalkyl group as used herein may refer to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and 1 to 10 carbon atoms as the remaining ring-forming atoms, and non-limiting examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term C.sub.1-C.sub.10 heterocycloalkylene group as used herein may refer to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkyl group.
[0307] The term C.sub.3-C.sub.10 cycloalkenyl group as used herein may refer to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term C.sub.3-C.sub.10 cycloalkenylene group as used herein may refer to a divalent group having the same structure as the C.sub.3-C.sub.10 cycloalkenyl group.
[0308] The term C.sub.1-C.sub.10 heterocycloalkenyl group as used herein may refer to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms as the remaining ring-forming atoms, and at least one carbon-carbon double bond in its ring. Non-limiting examples of the C.sub.1-C.sub.10 heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term C.sub.1-C.sub.10 heterocycloalkenylene group as used herein may refer to a divalent group having the same structure as the C.sub.1-C.sub.10 heterocycloalkenyl group.
[0309] The term C.sub.6-C.sub.60 aryl group as used herein may refer to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C.sub.6-C.sub.60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. The term C.sub.6-C.sub.60 arylene group used herein may refer to a divalent group having the same structure as the C.sub.6-C.sub.60 aryl group. When the C.sub.6-C.sub.60 aryl group and the C.sub.6-C.sub.60 arylene group each independently include two or more rings, the respective rings may be fused to each other.
[0310] The term C.sub.1-C.sub.60 heteroaryl group as used herein may refer to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms (as the remaining ring-forming atoms). Non-limiting examples of the C.sub.1-C.sub.60 heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. The term C.sub.1-C.sub.60 heteroarylene group as used herein may refer to a divalent group having the same structure as the C.sub.1-C.sub.60 heteroaryl group. When the C.sub.1-C.sub.60 heteroaryl group and the C.sub.1-C.sub.60 heteroarylene group each independently include two or more rings, the respective rings may be condensed (fused) with each other.
[0311] The term C.sub.6-C.sub.60 aryloxy group as used herein may refer to a group represented by OA.sub.102 (wherein A.sub.102 is the C.sub.6-C.sub.60 aryl group), and a C.sub.6-C.sub.60 arylthio group used herein may refer to a group represented by SA.sub.103 (wherein A.sub.103 is the C.sub.6-C.sub.60 aryl group).
[0312] The term monovalent non-aromatic condensed polycyclic group as used herein may refer to a monovalent group having two or more rings condensed with each other, only carbon atoms as ring-forming atoms (for example, having 8 to 60 carbon atoms), and no aromaticity in its entire molecular structure (i.e. the overall structure is non-aromatic). A non-limiting example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group. The term divalent non-aromatic condensed polycyclic group as used herein may refer to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
[0313] The term monovalent non-aromatic condensed heteropolycyclic group as used herein may refer to a monovalent group having two or more rings condensed to each other, at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, other than carbon atoms (for example, 1 to 60 carbon atoms), and no aromaticity in its entire molecular structure (i.e. the overall structure is non-aromatic). A non-limiting example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term divalent non-aromatic condensed heteropolycyclic group as used herein may refer to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.
[0314] The term C.sub.4-C.sub.60 carbocyclic group as used herein may refer to a monocyclic or polycyclic group having 4 to 60 carbon atoms in which ring-forming atoms carbon atoms only. The term C.sub.4-C.sub.60 carbocyclic group as used herein may refer to an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C.sub.4-C.sub.60 carbocyclic group may be a ring (such as benzene), a monovalent group (such as a phenyl group), or a divalent group (such as a phenylene group). In one or more embodiments, depending on the number of substituents connected to the C.sub.4-C.sub.60 carbocyclic group, the C.sub.4-C.sub.60 carbocyclic group may be a trivalent group or a quadrivalent group.
[0315] The term C.sub.1-C.sub.60 heterocyclic group as used herein may refer to a group having the same structure as the C.sub.4-C.sub.60 carbocyclic group, except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used, in addition to carbon atoms (the number of carbon atoms may be in a range of 1 to 60).
[0316] In the present specification, at least one substituent of the substituted C.sub.4-C.sub.60 carbocyclic group, the substituted C.sub.1-C.sub.60 heterocyclic group, the substituted C.sub.3-C.sub.10 cycloalkylene group, the substituted C.sub.1-C.sub.10 heterocycloalkylene group, the substituted C.sub.3-C.sub.10 cycloalkenylene group, the substituted C.sub.1-C.sub.10 heterocycloalkenylene group, the substituted C.sub.6-C.sub.60 arylene group, the substituted C.sub.1-C.sub.60 heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C.sub.1-C.sub.60 alkyl group, the substituted C.sub.2-C.sub.60 alkenyl group, the substituted C.sub.2-C.sub.60 alkynyl group, the substituted C.sub.1-C.sub.60 alkoxy group, the substituted C.sub.3-C.sub.10 cycloalkyl group, the substituted C.sub.1-C.sub.10 heterocycloalkyl group, the substituted C.sub.3-C.sub.10 cycloalkenyl group, the substituted C.sub.1-C.sub.10 heterocycloalkenyl group, the substituted C.sub.6-C.sub.60 aryl group, the substituted C.sub.6-C.sub.60 aryloxy group, the substituted C.sub.6-C.sub.60 arylthio group, the substituted C.sub.1-C.sub.60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:
[0317] deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group;
[0318] a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, and a C.sub.1-C.sub.60 alkoxy group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, Si(Q.sub.11)(Q.sub.12)(Q.sub.13), N(Q.sub.11)(Q.sub.12), B(Q.sub.11)(Q.sub.12), C(O)(Q.sub.11), S(O).sub.2(Q.sub.11), and P(O)(Q.sub.11)(Q.sub.12);
[0319] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;
[0320] a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.6-C.sub.60 aryloxy group, a C.sub.6-C.sub.60 arylthio group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, Si(Q.sub.21)(Q.sub.22)(Q.sub.23), N(Q.sub.21)(Q.sub.22), B(Q.sub.21)(Q.sub.22), C(O)(Q.sub.21), S(O).sub.2(Q.sub.21), and P(O)(Q.sub.21)(Q.sub.22); and
[0321] Si(Q.sub.31)(Q.sub.32)(Q.sub.33), N(Q.sub.31)(Q.sub.32), B(Q.sub.31)(Q.sub.32), C(O)(Q.sub.31), S(O).sub.2(Q.sub.31), and P(O)(Q.sub.31)(Q.sub.32), and
[0322] Q.sub.11 to Q.sub.13, Q.sub.21 to Q.sub.23, and Q.sub.31 to Q.sub.33 may each independently be selected from hydrogen, deuterium, F, Cl, Br, I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group, a C.sub.1-C.sub.60 alkoxy group, a C.sub.3-C.sub.10 cycloalkyl group, a C.sub.1-C.sub.10 heterocycloalkyl group, a C.sub.3-C.sub.10 cycloalkenyl group, a C.sub.1-C.sub.10 heterocycloalkenyl group, a C.sub.6-C.sub.60 aryl group, a C.sub.1-C.sub.60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C.sub.1-C.sub.60 alkyl group substituted with at least one selected from deuterium, F, and a cyano group, a C.sub.6-C.sub.60 aryl group substituted with at least one selected from deuterium, F, and a cyano group, a biphenyl group, and a terphenyl group.
[0323] The term Ph as used herein may refer to a phenyl group, the term Me as used herein may refer to a methyl group, the term Et as used herein may refer to an ethyl group, the term ter-Bu or Bu.sup.t as used herein may refer to a tert-butyl group, the term OMe as used herein may refer to a methoxy group, and D may refer to deuterium.
[0324] The term biphenyl group as used herein may refer to a phenyl group substituted with a phenyl group. In other words, the biphenyl group may be a substituted phenyl group having a C.sub.6-C.sub.60 aryl group as a substituent.
[0325] The term terphenyl group as used herein may refer to a phenyl group substituted with a biphenyl group. In other words, the terphenyl group may be a phenyl group having, as a substituent, a C.sub.6-C.sub.60 aryl group substituted with a C.sub.6-C.sub.60 aryl group.
[0326] * and * as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula.
[0327] Hereinafter, a compound according to embodiments and an organic light-emitting device according to embodiments will be described in more detail with reference to Synthesis Examples and Examples. The wording B was used instead of A used in describing Synthesis Examples may refer to an identical molar equivalent of B being used in place of A.
EXAMPLES
Synthesis Example: Synthesis of Compounds
Synthesis of Compound 1
(1) Synthesis of Reactant Compound a
[0328] ##STR00098##
[0329] 50 mmol (14.37 g) of triphenylmethyl chloride and aniline (12.5 ml) were heated in an Ar condition at a temperature of 220 C. After 20 minutes of the reaction, the reaction solution was cooled to a temperature of 95 C., and 2.0 M HCl (240 ml) and methanol (200 ml) were added thereto, and a reaction was additionally allowed to go for 30 minutes, thereby obtaining 13.2 g (83%) of Reactant Compound A through purification.
##STR00099##
(2) Synthesis of Compound 1
[0330] Reactant Compound A (6.6 g), 2-bromo-9-phenyl-9H-carbazole (5.3 g), Pd.sub.2(dba).sub.3 (1.06 g), P(t-Bu).sub.3 (0.30 g), and NaOtBu (4.78 g) were dissolved in toluene (150 ml), and then, the mixed solution was stirred at a temperature of 90 C. for 1 hour. The reaction solution was cooled to room temperature, and the reaction was terminated with water. Then, an extraction process was performed thereon three times by using ethylether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was separated and purified by column chromatography, thereby obtaining Intermediate 1-1 (5.76 g, yield: 60%). Compound 1 (2.6 g, yield: 40%) was also obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 1-1, except that bromo benzene (1.8 g) was used instead of 2-bromo-9-phenyl-9H-carbazole, and Intermediate 1-1 (5.76 g) was used instead of Reactant Compound A.
Synthesis of Compound 24
[0331] ##STR00100##
[0332] Compound 24 (4.1 g, yield: 57%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 1, except that 3-bromo-1,1-biphenyl (2.7 g) was used instead of bromo benzene.
Synthesis of Compound 42
[0333] ##STR00101##
[0334] Compound 42 (3.5 g, yield: 44%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 1, except that 3-(4-bromophenyl)-9-phenyl-9H-carbazole (4.9 g) and 4-bromo-1,1-biphenyl (2.6 g) were used instead of 2-bromo-9-phenyl-9H-carbazole and bromo benzene, respectively.
Synthesis of Compound 46
[0335] ##STR00102##
[0336] Compound 46 (3.6 g, yield: 47%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 42, except that bromonaphthalene (2.45 g) was used instead of 4-bromo-1,1-biphenyl.
Synthesis of Compound 63
[0337] ##STR00103##
[0338] Compound 63 (3.2 g, yield: 44%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 1, except that 3-(3-bromophenyl)-9-phenyl-9H-carbazole (4.97 g) and 2-bromo-1,1-biphenyl (2.33 g) were used instead of 2-bromo-9-phenyl-9H-carbazole and bromo benzene, respectively.
Synthesis of Compound 81
(1) Synthesis of Reactant Compound B
[0339] ##STR00104##
[0340] 4-bromoaniline (5.16 g) was dissolved in DMF (200 ml) after performing nitrogen blowing thereon, and then, n-Buli (14 ml) was added dropwise thereto at a temperature of 78 C. The mixed solution was stirred for 1 hour, and trimethyl borate (4.15 g) was added thereto at room temperature to allow a reaction overnight. The reaction was terminated with water, and HCl was added thereto to allow a reaction to go for additional 1 hour. Then, an extraction process was performed thereon three times by using ether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was re-crystallized by using MC, thereby obtaining Intermediate B-1 (6.45 g, yield: 52%).
[0341] Intermediate B-1 (6.45 g), Pd(PPh.sub.3).sub.4, (1.00 g), K.sub.2CO.sub.3 (6.72 g), and 1-bromo-4-iodobenzene (4.91 g) were dissolved in THF/H.sub.2O (100 ml/25 ml), and the mixed solution was stirred at a temperature 80 C. for 12 hours. The reaction solution was cooled to room temperature, and the reaction was terminated with water. Then, an extraction process was performed thereon three times by using ethylether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was separated and purified by column chromatography, thereby obtaining Reactant Compound B (4.65 g, yield: 67%).
(2) Synthesis of Compound 81
[0342] ##STR00105##
[0343] Reactant Compound B (6.17 g), 2-bromo-9-phenyl-9H-carbazole (4.02 g), Pd.sub.2(dba).sub.3 (1.35 g), P(t-Bu).sub.3 (0.30 g), and NaOtBu (4.26 g) were dissolved in toluene (80 ml), and then, the mixed solution was stirred at a temperature of 90 C. for 1 hour. The reaction solution was cooled to room temperature, and the reaction was terminated with water. Then, an extraction process was performed thereon three times by using ethylether. An organic layer separated therefrom was dried by using anhydrous sulfur magnesium, and then, distilled under reduced pressure. A residue obtained therefrom was separated and purified by column chromatography, thereby obtaining Intermediate 81-1 (6.5 g, yield: 67%). Compound 81 (3.76 g, yield: 65%) was also obtained in the same (or substantially the same) manner as in the synthesis of Intermediate 81-1, except that bromo benzene (3.07 g) instead of 2-bromo-9-phenyl-9H-carbazole, and Intermediate 81-1 (3.48 g) were used instead of Reactant Compound B.
Synthesis of Compound 108
[0344] ##STR00106##
[0345] Compound 108 (3.2 g, yield: 44%) was obtained in the same (or substantially the same) manner as in the synthesis of Compound 81, except that 2-bromo-9,9-dimethyl-9H-fluorene (2.33 g) was used instead of bromo benzene.
[0346] The compounds synthesized according to Synthesis Examples were identified by .sup.1H NMR and MS/FAB, and results thereof are shown in Table 1.
[0347] Compounds other than the compounds shown in Table 1 should be easily recognized (and synthesized) by one of ordinary skill in the art with reference to the synthetic routes and the raw materials above.
TABLE-US-00001 TABLE 1 MS/FAB Compound .sup.1H NMR (CDCl.sub.3, 400 MHz) found calc. 1 8.55(d, 1H), 8.24(d, 1H), 7.50-7.62(m, 653.35 652.85 5H), 7.00-7.35(m, 27H), 6.86(d, 2H) 24 8.58(d, 1H), 7.94(d, 1H), 7.75(d, 2H), 729.80 728.94 7.62-7.10(m, 36H), 6.86(d, 2H) 42 8.55(d, 1H), 7.89-7.99(m, 2H), 7.10- 806.04 805.04 7.55(m, 39H), 6.86(d, 2H) 46 8.55(d, 1H), 7.89-7.99(m, 3H), 7.71- 779.80 779.00 7.78(m, 3H) 7.10-7.55(m, 33H), 6.86(d, 2H) 63 8.55(d, 1H), 8.10(d, 1H), 7.77(d, 1H), 806.02 805.04 7.08-7.55(m, 38H), 6.86(d, 2H) 81 8.22(d, 1H), 8.24(d, 1H), 7.94(d, 1H), 729.04 728.94 7.50-7.62(m, 7H), 7.00-7.35(m, 29H) 108 8.55(d, 1H), 8.24(d, 1H), 7.86-7.94(m, 846.10 845.10 3H), 7.10-7.38, (m, 41H), 1.69(s, 2H)
Manufacture of Organic Light-Emitting Device
Comparative Example 1
[0348] As an anode, a glass substrate (Corning, Inc.), on which ITO was formed to a thickness of 15 /cm.sup.2 (1,200 ), was cut to a size of 50 mm50 mm0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then, cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the glass substrate was provided to a vacuum deposition apparatus.
[0349] 2-TNATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 600 , and then, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter, referred to as NPB), which is a hole transport material, was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 .
[0350] 9,10-di(naphthalen-2-yl)anthracene (hereinafter, referred to as DNA), as a blue phosphorescence host, and 4,4-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter, referred to as DPAVBi), as a blue phosphorescence dopant, were co-deposite at a weight ratio of 98:2 on the hole transport layer to form an emission layer having a thickness of 300 .
[0351] Then, Alq3 was deposited on the emission layer to form an electron transport layer having a thickness of 300 , LiF, which is a halogenated alkali metal, was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 , and Al was deposited on the electron injection layer to a thickness of 3,000 (cathode electrode) to form a LiF/AI electrode, thereby completing the manufacture of an organic light-emitting device.
##STR00107##
Comparative Example 2
[0352] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 100 was used instead of NPB in forming a hole transport layer.
##STR00108##
Comparative Example 3
[0353] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 101 was used instead of NPB in forming a hole transport layer.
##STR00109##
Comparative Example 4
[0354] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 102 was used instead of NPB in forming a hole transport layer.
##STR00110##
Comparative Example 5
[0355] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 103 was used instead of NPB in forming a hole transport layer.
##STR00111##
Comparative Example 6
[0356] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 104 was used instead of NPB in forming a hole transport layer.
##STR00112##
Example 1
[0357] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 1 was used instead of NPB in forming a hole transport layer.
Example 2
[0358] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 24 was used instead of NPB in forming a hole transport layer.
Example 3
[0359] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 42 was used instead of NPB in forming a hole transport layer.
Example 4
[0360] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 46 was used instead of NPB in forming a hole transport layer.
Example 5
[0361] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 63 was used instead of NPB in forming a hole transport layer.
Example 6
[0362] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 81 was used instead of NPB in forming a hole transport layer.
Example 7
[0363] An organic light-emitting device was manufactured in the same (or substantially the same) manner as in Comparative Example 1, except that Compound 108 was used instead of NPB in forming a hole transport layer.
[0364] The driving voltage, luminance, efficiency, and lifespan of the organic light-emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 6 were measured, and results thereof are shown in Table 2.
TABLE-US-00002 TABLE 2 Half lifespan Hole Driving Current (hr transport voltage density Luminance Efficiency Emission @100 material (V) (mA/cm.sup.2) (cd/m.sup.2) (cd/A) color mA/cm.sup.2) Comparative NPB 7.01 50 2645 5.29 blue 258 Example 1 Comparative 100 4.31 50 3755 7.51 blue 376 Example 2 Comparative 101 4.44 50 3740 7.48 blue 369 Example 3 Comparative 102 4.37 50 3665 7.33 blue 366 Example 4 Comparative 103 4.36 50 3605 7.21 blue 368 Example 5 Comparative 104 4.38 50 3715 7.43 blue 371 Example 6 Example 1 Compound 4.46 50 3700 7.40 blue 364 1 Example 2 Compound 4.43 50 3715 7.43 blue 362 24 Example 3 Compound 4.45 50 3710 7.42 blue 372 42 Example 4 Compound 4.47 50 3675 7.35 blue 373 46 Example 5 Compound 4.42 50 3685 7.37 blue 363 63 Example 6 Compound 4.41 50 3720 7.44 blue 366 81 Example 7 Compound 4.52 50 3725 7.45 blue 370 108
[0365] Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 7 showed excellent results compared to those of Comparative Examples 1 to 6.
[0366] According to the one or more embodiments, an organic light-emitting device including a compound represented by Formula 1 showed excellent efficiency and improved lifespan.
[0367] As used herein, the terms use, using, and used may be considered synonymous with the terms utilize, utilizing, and utilized, respectively.
[0368] In addition, the terms substantially, about, and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art.
[0369] Also, any numerical range recited herein is intended to include all sub-ranges of the same numerical precision subsumed within the recited range. For example, a range of 1.0 to 10.0 is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
[0370] It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims and their equivalents.