COMPOUND FOR ORGANIC ELECTRICAL ELEMENT, ORGANIC ELECTRICAL ELEMENT USING SAME, AND ELECTRONIC DEVICE THEREOF

Abstract

Provided are a compound capable of improving the luminous efficiency, stability and lifespan of an organic electronic device employing the same, an organic electronic element employing the same, and an electronic device thereof.

Claims

1. A compound represented by Formula 1: ##STR00090## wherein: X is O or S, R.sup.1 and R.sup.2 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; 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 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; and where a and b are 2 or more, R.sup.1 and R.sup.2 are each in plural being the same or different, L.sup.1 and L.sup.2 are each independently selected from the group consisting of a single bond, a C.sub.6-C.sub.60 arylene group, a C.sub.2-C.sub.60 heteroarylene group including at least one heteroatom of O, N, S, Si or and where q and w are 2 or more, L.sup.1 and L.sup.2 are each in plural being the same or different, Ar.sup.1, Ar.sup.2, Ar.sup.3 and Ar.sup.4 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group, a substituent represented by Formula 1-a, and a substituent represented by Formula 1-b, with the proviso that at least one pair of Ar.sup.1 and Ar.sup.2, and Ar.sup.3 and Ar.sup.4 is a substituent represented by Formula 1-a, a and b are each independently an integer of 0 to 4, q and w are each independently an integer of 0 to 2, with the proviso that q+w is 2 or more, Y is NR.sup.a, O or S, R.sup.a is selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a C.sub.2-C.sub.60 heteroaryl group including at least one heteroatom of O, N, S, Si or F; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or F; and —L′—N(R.sup.c)(R.sup.d), L′ is selected from the group consisting of a C.sub.6-C.sub.60 arylene group; a fluorenylene group; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; and a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or F; R.sup.c and R.sup.d are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or F; R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or F; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; a C.sub.1-C.sub.60 alkyl group; an C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; and a C.sub.6-C.sub.60 aryloxy group, and where a, b, c and d are 2 or more, R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are each in plural being the same or different, d, g and h are each independently an integer from 0 to 4, c is an integer from 0 to 3, L.sup.5 and L.sub.5 are each independently selected from the group consisting of a single bond; a C.sub.6-C.sub.60 arylene group; a C.sub.2-C.sub.60 heteroarylene group including at least one heteroatom of O, N, S, Si or F; R′ and R″ are independently of each other hydrogen; deuterium; halogen; cyano group; 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 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heteroaryl group including at least one heteroatom of O, N, S, Si or F; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; and R′ and R″ are bonded to each other to form a spiro, * indicates the position to be bonded, wherein the aryl group, arylene group, heteroarylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C.sub.1-C.sub.20 alkylthio group; C.sub.1-C.sub.20 alkoxyl group; C.sub.1-C.sub.20 alkyl group; C.sub.2-C.sub.20 alkenyl group; C.sub.2-C.sub.20 alkynyl group; C.sub.6-C.sub.20 aryl group; C.sub.6-C.sub.20 aryl group substituted with deuterium; a fluorenyl group; C.sub.2˜C.sub.20 heterocyclic group; C.sub.3-C.sub.20 cycloalkyl group; C.sub.7-C.sub.20 arylalkyl group; and C.sub.8-C.sub.20 arylalkenyl group; and —L′—N(R.sup.c)(R.sup.d); wherein the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C.sub.3-C.sub.60 aliphatic ring or a C.sub.6-C.sub.60 aromatic ring or a C.sub.2-C.sub.60 heterocyclic group or a fused ring formed by combination thereof.

2. The compound of claim 1, wherein Formula 1 includes a compound represented by Formula 2: ##STR00091## wherein: X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, L.sup.2, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′ and R″ are the same as defined in claim 1, a′, c and e are each independently an integer of 0 to 3, b, d and f are each independently an integer of 0 to 4, x is an integer of 0 or 1, y is an integer of 0 to 2, provided that x+y is 1 or more, R.sup.5 and R.sup.6 are the same as the definition of R.sup.1 to R.sup.2 in claim 1, L.sup.3 and L.sup.4 are the same as the definition of L.sup.2 and L.sup.5 in claim 1, R′″ and R″″ are the same as the definitions of R′ and R″ in claim 1.

3. The compound of claim 2, wherein Formula 2 is represented by any one of Formulas 2-1 to 2-5: ##STR00092## ##STR00093## wherein: X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′, R″, R′″, R″″, b, c, d, e and f are the same as defined in claim 2, L.sup.6 is the same as the definition of L.sup.1 to L.sup.5 in claim 2, Ar.sup.5 and Ar.sup.6 are the same as the definitions of Ar.sup.1 to Ar.sup.4 in claim 2, a″ and b″ are independently an integer of 0 to 2, and a′ and b′ are independently an integer of 0 to 3.

4. The compound of claim 2, wherein Formula 2 is represented by Formula 2-6 or Formula 2-7: ##STR00094## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′, R″, R′″, R″″, a′, b, c, d, e, f, x and y are the same as defined in claim 2.

5. The compound of claim 2, wherein Formula 2 is represented by any one of Formulas 2-8 to 2-11: ##STR00095## ##STR00096## wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′, R″, R′″, R″″, a′, b, c, d, e, f, x and y are the same as defined in claim 2.

6. The compound of claim 2, wherein Formula 2 is represented by any one of Formulas 2-12 to 2-15: ##STR00097## ##STR00098## wherein: X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, Ar.sup.1, Ar.sup.2, R′, R″, R′″ and R″″ are the same as defined in claim 2, and a′, b′, c and e are independently an integer of 0 to 3, and b and f are independently an integer of 0 to 4.

7. The compound of claim 2, wherein Formula 2 is represented by any one of Formulas 2-16 to 2-19: ##STR00099## ##STR00100## wherein: X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, Ar.sup.1, Ar.sup.2, R′, R″, R′″ and R″″ are the same as defined in claim 2, and a′, b′, c and e are independently an integer of 0 to 3, and b and f are independently an integer of 0 to 4.

8. The compound of claim 2, wherein Formula 2 is represented by Formula 2-20: ##STR00101## wherein: X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, Ar.sup.1, Ar.sup.2, R′, R″, R′″ and R″″ are the same as defined in claim 2, and a′, b′, c and e are independently an integer of 0 to 3, and b and f are independently an integer of 0 to 4.

9. The compound of claim 2, wherein the compound represented by Formula 1 is any one of the following compounds P-1 to P-60: ##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112## ##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117## ##STR00118## ##STR00119## ##STR00120## ##STR00121## ##STR00122## ##STR00123##

10. An organic electronic element comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer comprises a single compound or 2 or more compounds represented by Formula 1 of claim 1.

11. The organic electronic element of claim 10, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, an emitting auxiliary layer, an emitting layer, an electron transport auxiliary layer, an electron transport layer, and an electron injection layer.

12. The organic electronic element of claim 10, wherein the organic material layer is an emitting auxiliary layer.

13. The organic electronic element of claim 10, wherein the organic electronic element further comprises a light efficiency enhancing layer formed on at least one surface of the anode and the cathode, the surface being opposite to the organic material layer.

14. The organic electronic element of claim 10, wherein the organic material layer comprises 2 or more stacks including a hole transport layer, an emitting layer, and an electron transport layer sequentially formed on the anode.

15. The organic electronic element of claim 10, wherein the organic material layer further comprises a charge generation layer formed between the 2 or more stacks.

16. The organic electronic element of claim 10, wherein the organic electronic element is a green organic electronic element.

17. The organic electronic element of claim 16, wherein the organic material layer is an emitting auxiliary layer of the green organic electronic element.

18. An electronic device comprising: a display device comprising the organic electronic element of claim 10; and a control unit for driving the display device.

19. An electronic device according to claim 18, wherein the organic electronic element is at least one of an OLED, an organic solar cell, an organic photo conductor (OPC), an organic transistor (organic TFT), and an element for monochromic or white illumination.

Description

DETAILED DESCRIPTION

[0018] Hereinafter, some embodiments of the present invention will be described in detail. Further, in the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear. In addition, terms, such as first, second, A, B, (a), (b) or the like may be used herein when describing components of the present invention. Each of these terminologies is not used to define an essence, order or sequence of a corresponding component but used merely to distinguish the corresponding component from other component(s). It should be noted that if a component is described as being “connected”, “coupled”, or “connected” to another component, the component may be directly connected or connected to the other component, but another component may be “connected “, ” coupled” or “connected” between each component.

[0019] As used in the specification and the accompanying claims, unless otherwise stated, the following is the meaning of the term as follows.

[0020] Unless otherwise stated, the term “halo” or “halogen”, as used herein, includes fluorine, bromine, chlorine, or iodine.

[0021] Unless otherwise stated, the term “alkyl” or “alkyl group”, as used herein, has a single bond of 1 to 60 carbon atoms, and means saturated aliphatic functional radicals including a linear alkyl group, a branched chain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl group substituted with a alkyl or an alkyl group substituted with a cycloalkyl.

[0022] Unless otherwise stated, the term “alkenyl” or “alkynyl”, as used herein, has double or triple bonds of 2 to 60 carbon atoms, but is not limited thereto, and includes a linear or a branched chain group.

[0023] Unless otherwise stated, the term “cycloalkyl”, as used herein, means alkyl forming a ring having 3 to 60 carbon atoms, but is not limited thereto.

[0024] Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or “alkyloxy group”, as used herein, means an oxygen radical attached to an alkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

[0025] Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”, as used herein, means an oxygen radical attached to an aryl group, but is not limited thereto, and has 6 to 60 carbon atoms.

[0026] The terms “aryl group” and “arylene group” used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present invention, an aryl group or an arylene group means a single ring or multiple ring aromatic, and includes an aromatic ring formed by an adjacent substituent joining or participating in a reaction.

[0027] For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

[0028] The prefix “aryl” or “ar” means a radical substituted with an aryl group. For example, an arylalkyl may be an alkyl substituted with an aryl, and an arylalkenyl may be an alkenyl substituted with aryl, and a radical substituted with an aryl has a number of carbon atoms as defined herein.

[0029] Also, when prefixes are named subsequently, it means that substituents are listed in the order described first. For example, an arylalkoxy means an alkoxy substituted with an aryl, an alkoxylcarbonyl means a carbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl also means an alkenyl substituted with an arylcarbonyl, wherein the arylcarbonyl may be a carbonyl substituted with an aryl.

[0030] Unless otherwise stated, the term “heterocyclic group”, as used herein, contains one or more heteroatoms, but is not limited thereto, has 2 to 60 carbon atoms, includes any one of a single ring or multiple ring, and may include heteroaliphadic ring and heteroaromatic ring. Also, the heterocyclic group may also be formed in conjunction with an adjacent group.

[0031] Unless otherwise stated, the term “heteroatom”, as used herein, represents at least one of N, O, S, P, or Si.

[0032] Also, the term “heterocyclic group” may include a ring including SO.sub.2 instead of carbon consisting of cycle. For example, “heterocyclic group” includes the following compound.

##STR00002##

[0033] Unless otherwise stated, the term “fluorenyl group” or “fluorenylene group”, as used herein, means a monovalent or divalent functional group, in which R, R′ and R″ are all hydrogen in the following structures, and the term “substituted fluorenyl group” or “substituted fluorenylene group” means that at least one of the substituents R, R′, R″ is a substituent other than hydrogen, and include those in which R and R′ are bonded to each other to form a spiro compound together with the carbon to which they are bonded.

##STR00003##

[0034] The term “Spiro compound”, as used herein, has a ‘Spiro union’, and a Spiro union means a connection in which two rings share only one atom. At this time, atoms shared in the two rings are called ‘spiro atoms’, and these compounds are called ‘monospiro-’, ‘di-spiro ’ and ‘tri-spiro’, respectively, depending on the number of spiro atoms in a compound.

[0035] Unless otherwise stated, the term “aliphatic”, as used herein, means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and the term “aliphatic ring”, as used herein, means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

[0036] Unless otherwise stated, the term “ring”, as used herein, means an aliphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6 to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or a fused ring formed by the combination of them, and includes a saturated or unsaturated ring.

[0037] Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds include, but are not limited thereto, one or more heteroatoms.

[0038] Also, unless expressly stated, as used herein, “substituted” in the term “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of deuterium, halogen, an amino group, a nitrile group, a nitro group, a C.sub.1-C.sub.20 alkyl group, a C.sub.1-C.sub.20 alkoxyl group, a C.sub.1-C.sub.20 alkylamine group, a C.sub.1-C.sub.20 alkylthiopen group, a C.sub.6-C.sub.20 arylthiopen group, a C.sub.2-C.sub.20 alkenyl group, a C.sub.2-C.sub.20 alkynyl group, a C.sub.3-C.sub.20 cycloalkyl group, a C.sub.6-C.sub.20 aryl group, a C.sub.6-C.sub.20 aryl group substituted by deuterium, a C.sub.8-C.sub.20 arylalkenyl group, a silane group, a boron group, a germanium group, and a C.sub.2-C.sub.20 heterocyclic group, but is not limited to these substituents.

[0039] Also, unless there is an explicit explanation, the formula used in the present invention is the same as the definition of the substituent by the exponent definition of the following formula.

##STR00004##

[0040] Here, when a is an integer of zero, the substituent R.sup.1 is absent, when a is an integer of 1, the sole substituent R.sup.1 is linked to any one of the carbon constituting the benzene ring, when a is an integer of 2 or 3, each is bonded as follows, where R.sup.1 may be the same or different from each other, when a is an integer of 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of the hydrogen bonded to the carbon forming the benzene ring is omitted.

##STR00005##

[0041] Hereinafter, a compound according to an aspect of the present invention and an organic electronic element including the same will be described.

[0042] The present invention provides a compound represented by Formula 1.

##STR00006##

{wherein, each symbol may be defined as follows.

[0043] X is O or S,

[0044] R.sup.1 and R.sup.2 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; 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 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; or, in case a and b are 2 or more, R.sup.1 and R.sup.2 are each in plural being the same or different.

[0045] Wherein in case R.sup.1 and R.sup.2 are an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, and more preferably a C.sub.6-C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0046] In case R.sup.1 and R.sup.2 are a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0047] In case R.sup.1 and R.sup.2 are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring.

[0048] In case R.sup.1 and R.sup.2 are an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.1-C.sub.24 alkyl group.

[0049] In case R.sup.1 and R.sup.2 are an alkenyl group, they may be preferably an C.sub.2˜C.sub.30 alkenyl group, more preferably an C.sub.2˜-C.sub.24 alkenyl group.

[0050] In case R.sup.1 and R.sup.2 are an alkynyl group, they may be preferably an C.sub.2˜C.sub.30 alkynyl group, more preferably an C.sub.2˜C.sub.24 alkynyl group.

[0051] In case R.sup.1 and R.sup.2 are an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1˜C.sub.24 alkoxyl group.

[0052] In case R.sup.1 and R.sup.2 are an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C.sub.6˜C.sub.24 aryloxy group.

[0053] Wherein L.sup.1 and L.sup.2 are each independently selected from the group consisting of a single bond, a C.sub.6-C.sub.60 arylene group, a C.sub.2-C.sub.60 heteroarylene group including at least one heteroatom of O, N, S, Si or P; or in case q and w are 2 or more, L.sup.1 and L.sup.2 are each in plural being the same or different.

[0054] In case L.sup.1 and L.sup.2 are an arylene group, it may be preferably a C.sub.6-C.sub.30 arylene group, more preferably a C.sub.6-C.sub.24 arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0055] In case L.sup.1 and L.sup.2 are an heteroarylene group, it may be preferably a C.sub.2-C.sub.30 heteroarylene group, more preferably a C.sub.2-C.sub.24 heteroarylene group,

[0056] Wherein Ar.sup.1, Ar.sup.2, Ar.sup.3 and Ar.sup.4 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a substituent represented by Formula 1-a; and a substituent represented by Formula 1-b, however, at least one pair of Ar.sup.1 and Ar.sup.2, and Ar.sup.3 and Ar.sup.4 is a substituent represented by Formula 1-a.

[0057] In case Ar.sup.1, Ar.sup.2, Ar.sup.3 and Ar.sup.4 are an aryl group, they may be preferably a C.sub.6-C.sub.30 aryl group, most preferably a C.sub.6-C.sub.25 aryl group, for example, phenylene, biphenyl, naphthalene, terphenyl, and the like.

[0058] a and b are each independently an integer of 0 to 4, q and w are each independently an integer of 0 to 2, with the proviso that q+w is 2 or more,

[0059] In Formulas 1-a to 1-b, each symbol may be defined as follows.

[0060] Y is NR.sup.a, O or S,

[0061] R.sup.a is selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a C.sub.2-C.sub.60 heteroaryl group including at least one heteroatom of O, N, S, Si or a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or and —L′—N(R.sup.c)(R.sup.d);

[0062] In case R.sup.a is an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, and more preferably a C.sub.6-C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0063] In case R.sup.a is a heteroaryl group, it may be preferably a C.sub.2-C.sub.30 heteroaryl group, and more preferably a C.sub.2-C.sub.24 heteroaryl group,

[0064] In case R.sup.a is a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0065] L′ is selected from the group consisting of a C.sub.6-C.sub.60 arylene group; a fluorenylene group; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; and a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P;

[0066] In case L′ is an arylene group, it may be preferably a C.sub.6-C.sub.30 arylene group, more preferably a C.sub.6-C.sub.24 arylene group, for example, phenylene, biphenyl, naphthalene, terphenyl, etc.

[0067] In case L′ is a heterocyclic group, it may be preferably a C.sub.2˜C.sub.30 heterocyclic group, and more preferably a C.sub.2˜C.sub.24 heterocyclic group, for example, pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0068] In case L′ is fused ring groups, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring.

[0069] R.sup.c and R.sup.d are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P;

[0070] In case R.sup.c and R.sup.d are an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, and more preferably a C.sub.6-C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0071] In case R.sup.c and R.sup.d are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring.

[0072] In case R.sup.c and R.sup.d are a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0073] R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are each independently selected from the group consisting of a C.sub.6-C.sub.60 aryl group; a C.sub.2-C.sub.60 heterocyclic group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; a C.sub.1-C.sub.60 alkyl group; an C.sub.2-C.sub.60 alkenyl group; a C.sub.2-C.sub.60 alkynyl group; a C.sub.1-C.sub.60 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; or in case a, b, c and d are 2 or more, R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are each in plural being the same or different.

[0074] Wherein in case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, and more preferably a C.sub.6-C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0075] In case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are a heterocyclic group, it may be preferably a C.sub.2-C.sub.30 heterocyclic group, and more preferably a C.sub.2-C.sub.24 heterocyclic group, for example, it may be pyrazine, thiophene, pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline, carbazole, dibenzoquinazoline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

[0076] In case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring.

[0077] In case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.1-C.sub.24 alkyl group.

[0078] In case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are an alkenyl group, it may be preferably an C.sub.2˜C.sub.30 alkenyl group, more preferably an C.sub.2˜C.sub.24 alkenyl group.

[0079] In case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are an alkynyl group, it may be preferably an C.sub.2˜C.sub.30 alkynyl group, more preferably an C.sub.2˜C.sub.24 alkynyl group.

[0080] In case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1˜C.sub.24 alkoxyl group.

[0081] In case R.sup.3, R.sup.4, R.sup.7 and R.sup.8 are an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C.sub.6˜C.sub.24 aryloxy group.

[0082] d, g and h are each independently an integer from 0 to 4, c is an integer from 0 to 3,

[0083] L.sup.5 and L.sub.5 are each independently selected from the group consisting of a single bond; a C.sub.6-C.sub.60 arylene group; a C.sub.2-C.sub.60 heteroarylene group including at least one heteroatom of O, N, S, Si or P;

[0084] In case L.sup.5 and L.sub.5 are an arylene group, it may be preferably a C.sub.6-C.sub.30 arylene group, and more preferably a C.sub.6-C.sub.24 arylene group,

[0085] In case L.sup.5 and L.sub.5 are a heteroarylene group, it may be preferably a C.sub.2-C.sub.30 heteroarylene group, and more preferably a C.sub.2-C.sub.24 heteroarylene group,

[0086] R′ and R″ are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano 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 alkoxyl group; a C.sub.6-C.sub.60 aryloxy group; a C.sub.6-C.sub.60 aryl group; a fluorenyl group; a C.sub.2-C.sub.60 heteroaryl group including at least one heteroatom of O, N, S, Si or P; a fused ring group of a C.sub.3-C.sub.60 aliphatic ring and a C.sub.6-C.sub.60 aromatic ring; wherein R′ and R″ are bonded to each other to form a spiro.

[0087] In case R′ and R″ are an alkyl group, it may be preferably a C.sub.1-C.sub.30 alkyl group, and more preferably a C.sub.11-C.sub.24 alkyl group.

[0088] In case R′ and R″ are an alkenyl group, they may be preferably an C.sub.2˜C.sub.30 alkenyl group, more preferably an C.sub.2-C.sub.24 alkenyl group.

[0089] In case R′ and R″ are an alkynyl group, they may be preferably an C.sub.2˜C.sub.30 alkynyl group, more preferably an C.sub.2˜C.sub.24 alkynyl group.

[0090] In case R′ and R″ are an alkoxyl group, it may be preferably a C.sub.1-C.sub.30 alkoxyl group, more preferably an C.sub.1˜C.sub.24 alkoxyl group.

[0091] In case R′ and R″ are an aryloxy group, it may be preferably a C.sub.6-C.sub.30 aryloxy group, more preferably an C.sub.6˜C.sub.24 aryloxy group.

[0092] In case R′ and R″ are an aryl group, it may be preferably a C.sub.6-C.sub.30 aryl group, more preferably an C.sub.6˜C.sub.25 aryl group, for example, it may be phenylene, biphenyl, naphthalene, terphenyl, etc.

[0093] In case R′ and R″ are a heteroaryl group, it may be preferably a C.sub.2-C.sub.30 heteroaryl group, more preferably an C.sub.2˜C.sub.24 heteroaryl group.

[0094] In case R′ and R″ are a fused ring group, it may be preferably a fused ring group of a C.sub.3-C.sub.30 aliphatic ring and a C.sub.6-C.sub.30 aromatic ring, more preferably a fused ring group of a C.sub.3-C.sub.24 aliphatic ring and a C.sub.6-C.sub.24 aromatic ring.

[0095] * indicates the position to be bonded,

[0096] wherein the aryl group, arylene group, heteroarylene group, heterocyclic group, fluorenyl group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group may be substituted with one or more substituents selected from the group consisting of deuterium; halogen; silane group; siloxane group; boron group; germanium group; cyano group; nitro group; C.sub.1-C.sub.20 alkylthio group; C.sub.1-C.sub.20 alkoxyl group; C.sub.1-C.sub.20 alkyl group; C.sub.2-C.sub.20 alkenyl group; C.sub.2-C.sub.20 alkynyl group; C.sub.6-C.sub.20 aryl group; C.sub.6-C.sub.20 aryl group substituted with deuterium; a fluorenyl group; C.sub.2˜C.sub.20 heterocyclic group; C.sub.3-C.sub.20 cycloalkyl group; C.sub.7-C.sub.20 arylalkyl group; and C.sub.8-C.sub.20 arylalkenyl group; and —L′—N(R.sup.c)(R.sup.d); also the substituents may be bonded to each other to form a saturated or unsaturated ring, wherein the term ‘ring’ means a C.sub.3-C.sub.60 aliphatic ring or a C.sub.6-C.sub.60 aromatic ring or a C.sub.2-C.sub.60 heterocyclic group or a fused ring formed by the combination thereof.

[0097] Also, Formula 1 includes a compound represented by Formula 2.

##STR00007##

{Wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, L.sup.1, L.sup.2, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′ and R″ are the same as defined above,

[0098] a′, c and e are each independently an integer of 0 to 3, b, d and f are each independently an integer of 0 to 4,

[0099] x is 0 or 1, y is an integer from 0 to 2, provided that x+y is 1 or more,

[0100] R.sup.5 and R.sup.6 are the same as the definitions of R.sup.1 to R.sup.2 above,

[0101] L.sup.3 and L.sup.4 are the same as the definitions of L.sup.2 and L.sup.5 above,

[0102] R′″ and R″″ have the same definitions as R′ and R″ above.}

[0103] Also, Formula 1 is represented by Formulas 2-1 to 2-5

##STR00008## ##STR00009##

Wherein, X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′, R″, R′″, R″″, b, c, d, e and f are the same as defined above,

[0104] L.sup.6 is the same as the definition of L.sup.1 to L.sup.5,

[0105] Ar.sup.5 and Ar.sup.6 are the same as the definitions of Ar.sup.1 to Ar.sup.4,

[0106] a″ and b″ are independently integers from 0 to 2, and a′ and b′ are independently integers from 0 to 3.

[0107] Also, Formula 1 is represented by Formula 2-6 or Formula 2-7

##STR00010##

{Wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′, R″, R′″, R″″, a′, b, c, d, e, f, x and y are the same as defined above.}

[0108] Also, Formula 1 is represented by Formulas 2-8 to 2-11.

##STR00011##

{Wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, L.sup.5, Ar.sup.1, Ar.sup.2, Ar.sup.3, Ar.sup.4, R′, R″, R′″, R″″, a′, b, c, d, e, f, x and y are the same as defined above.}

[0109] Also, Formula 1 is represented by Formulas 2-12 to 2-15

##STR00012## ##STR00013##

{Wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, Ar.sup.1, Ar.sup.2, R′, R″, R′″ and R″″ are the same as defined above,

[0110] a′, b′, c and e are independently integers from 0 to 3, and b and f are independently integers from 0 to 4.}

[0111] Also, Formula 1 is represented by Formulas 2-16 to 2-19

##STR00014## ##STR00015##

{Wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, Ar.sup.1, Ar.sup.2, R′, R″, R′″ and R″″ are the same as defined above,

[0112] a′, b′, c and e are independently integers from 0 to 3, and b and f are independently integers from 0 to 4.}

[0113] Also, Formula 1 is represented by Formula 2-20.

##STR00016##

{Wherein X, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, L.sup.1, L.sup.2, L.sup.3, L.sup.4, Ar.sup.1, Ar.sup.2, R′, R″, R′″ and R″″ are the same as defined above,

[0114] a′, b′, c and e are independently integers from 0 to 3, and b and f are independently integers from 0 to 4.}

[0115] Specifically, the compound represented by Formula 1 may be any one of the following compounds P-1 to P-60, but is not limited thereto.

##STR00017## ##STR00018## ##STR00019## ##STR00020## ##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025## ##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030## ##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038##

[0116] Referring to FIG. 1, the organic electronic element (100) according to the present invention includes a first electrode (110), a second electrode (170), and an organic material layer including a single compound or 2 or more compounds represented by Formula 1 between the first electrode (110) and the second electrode (170). In this case, the first electrode (110) may be an anode, and the second electrode (170) may be a cathode. In the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.

[0117] The organic material layer may sequentially include a hole injection layer (120), a hole transport layer (130), an emitting layer (140), an electron transport layer (150), and an electron injection layer (160) on the first electrode (110). In this case, the remaining layers except for the emitting layer (140) may not be formed. It may further include a hole blocking layer, an electron blocking layer, an emitting-auxiliary layer (220), a buffer layer (210), etc. and the electron transport layer (150) and the like may serve as a hole blocking layer. (See FIG. 2)

[0118] Also, the organic electronic element according to an embodiment of the present invention may further include a protective layer or a light efficiency enhancing layer (180). The light efficiency enhancing layer may be formed on one of both surfaces of the first electrode not in contact with the organic material layer or on one of both surfaces of the second electrode not in contact with the organic material layer. The compound according to an embodiment of the present invention applied to the organic material layer may be used as a host or dopant of the hole injection layer (120), the hole transport layer (130), the emitting-auxiliary layer (220), electron transport auxiliary layer, the electron transport layer (150), and an electron injection layer (160), the emitting layer (140) or as a material for the light efficiency enhancing layer. Preferably, for example, the compound according to Formula 1 of the present invention may be used as a host of the emitting layer and/or as a material for the emitting auxiliary layer.

[0119] The organic material layer may include 2 or more stacks including a hole transport layer, an emitting layer and an electron transport layer sequentially formed on the anode, further include a charge generation layer formed between the 2 or more stacks (see FIG. 3).

[0120] Otherwise, even with the same core, the band gap, electrical characteristics, interface characteristics, etc. may vary depending on which position the substituent is bonded to, therefore the choice of core and the combination of sub-substituents bound thereto are also very important, and in particular, when the optimal combination of energy levels and T1 values and unique properties of materials(mobility, interfacial characteristics, etc.) of each organic material layer is achieved, a long lifespan and high efficiency can be achieved at the same time. The organic electroluminescent device according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method. For example, depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, and after forming an organic material layer including the hole injection layer (120), the hole transport layer (130), the emitting layer (140), the electron transport layer (150) and the electron injection layer (160) thereon, it can be prepared by depositing a material that can be used as a cathode thereon.

[0121] Also, in the present invention, the organic material layer is formed by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, and a roll-to-roll process, and the organic material layer provides an organic electronic element comprising the compound as an electron transport material.

[0122] As another specific example, the same or different compounds of the compound represented by Formula 1 are mixed and used in the organic material layer.

[0123] Also, the present invention provides an emitting auxiliary layer composition comprising the compound represented by Formula 1, and provides an organic electronic element including the emitting auxiliary layer.

[0124] Also, the present invention provides a green organic electronic element comprising the compound represented by Formula 1.

[0125] Also, the present invention provides a green organic electronic element comprising an emitting auxiliary layer comprising the compound represented by Formula (1).

[0126] Also, the present invention provides an electronic device comprising a display device including the organic electronic element; and a control unit for driving the display device;

[0127] In another aspect, the organic electronic element is at least one of an organic electroluminescent device, an organic solar cell, an organic photo conductor, an organic transistor, and a device for monochromatic or white lighting. At this time, the electronic device may be a current or future wired/wireless communication terminal, and covers all kinds of electronic devices including mobile communication terminals such as mobile phones, a personal digital assistant (PDA), an electronic dictionary, a point-to-multipoint(PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, and various kinds of computers.

[0128] Hereinafter, a synthesis example of the compound represented by Formula 1 of the present invention and a manufacturing example of an organic electronic element of the present invention will be described in detail with reference to Examples, but the present invention is not limited to the following Examples.

SYNTHESIS EXAMPLE

[0129] The compound represented by Formula 1 according to the present invention (final products) is synthesized by reacting Sub 1 and Sub 2 as shown in Scheme 1, but is not limited thereto.

##STR00039##

I. Synthesis of Sub 1

[0130] Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.

##STR00040##

[0131] Synthesis examples of specific compounds belonging to Sub 1 are as follows.

1. Synthesis Example of Sub 1-1

[0132] ##STR00041##

[0133] (1) Synthesis of Sub 1-1 b

[0134] Sub 1-1a (50 g, 0.21 mol), (4-chloro-2-hydroxyphenyl)boronic acid (36.6 g, 0.21 mol), Pd(PPh.sub.3).sub.4 (7.4 g, 0.006 mol), NaOH (25.5 g, 0.64 mol), THF (425 ml), Water (130 ml) were added and reacted for 6 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. Then, the concentrated reactant was separated using a silicagel column or recrystallization method to obtain 49 g (81.2%) of the product Sub 1-1b.

[0135] (2) Synthesis of Sub 1-1c

[0136] The obtained Sub 1-1 b (50 g, 0.18 mol) was added with Pd(OAc).sub.2 (1.2 g, 0.005 mol) and 3-nitropyridine (0.66 g, 0.005 mol), After dissolving in C.sub.6F.sub.6 (280 ml) and DMI (350 ml), tert-butyl peroxybenzoate (102.75 g, 0.53 mol) was added and stirred at 90° C. When the reaction was completed, 40 g (yield: 80.6%) of the product Sub 1-1c was obtained by using the separation method of Sub 1-1b.

[0137] (3) Synthesis of Sub 1-1

[0138] Diphenylamine (18 g, 0.11 mol), Pd.sub.2(dba).sub.3 (2.9 g, 0.0032 mol), 50% P(t-Bu).sub.3 (2.6 g, 0.0064 mol), NaOt-Bu (30.8 g, 0.32 mol), Toluene (220 ml) were added to the obtained Sub 1-1c (30 g, 0.11 mol) and stirred at 90° C. When the reaction was completed, 55 g (yield: 90.6%) of the product Sub 1-1 was obtained by using the separation method of Sub 1-1b.

2. Synthesis Example of Sub 1-6

[0139] ##STR00042##

[0140] (1) Synthesis of Sub 1-6b

[0141] Sub 1-6a (60 g, 0.25 mol), (5-chloro-4-(methylsulfinyl)-[1,1′-biphenyl]-3-yl)boronic acid (75 g, 0.25 mol), Pd(PPh.sub.3).sub.4 (7 g, 0.007 mol), NaOH (30.5 g, 0.76 mol), THF (510 ml) and Water (150 ml) were added and reacted for 6 hours.

[0142] After the reaction was completed, 88 g (85.4%) of Sub 1-6b was obtained by using the separation method of Sub 1-1b.

(2) Synthesis of Sub 1-6c

[0143] Sub 1-6b (30 g, 0.07 mol) was dissolved in H.sub.2SO.sub.4 (150 ml) and stirred at 45° C. for 12 hours. When the reaction was completed, the reactant was slowly added to an aqueous NaOH solution and then neutralized. Then, 23 g (yield: 83.2%) of the product Sub 1-6c was obtained by using a silicagel column or recrystallization method for the produced reactant.

(3) Synthesis of Sub 1-6

[0144] Di([1,1′-biphenyl]-4-yl)amine (43 g, 0.13 mol), Pd.sub.2(dba).sub.3 (3.7 g, 0.004 mol), 50% P(t-Bu).sub.3 (3.3 g, 0.008 mol), NaOt-Bu (38.7 g, 0.4 mol), toluene (270 ml) were added to the obtained Sub 1-6c (50 g, 0.13 mol) and stirred at 90° C.

[0145] When the reaction was completed, 40 g (yield: 80.6%) of the product Sub 1-6 was obtained by using the separation method of Sub 1-1b.

3. Synthesis Example of Sub 1-14

[0146] ##STR00043##

(1) Synthesis of Sub 1-14b

[0147] Sub 1-14a (30 g, 0.08 mol), (3-hydroxyphenanthren-4-yl)boronic acid (18 g, 0.08 mol), Pd(PPh.sub.3).sub.4 (2.6 g, 0.002 mol), NaOH (9.2 g, 0.23 mol), THF (150 ml) and Water (40 ml) were added and reacted for 6 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. After the reaction was completed, 31 g (yield: 88.5%) of the product Sub 1-14b was obtained by using the separation method of Sub 1-1b.

(2) Synthesis of Sub 1-14c

[0148] The obtained Sub 1-14b (30 g, 0.07 mol) was put together with Pd(OAc).sub.2 (0.44 g, 0.002 mol), 3-nitropyridine (0.24 g, 0.002 mol), dissolved in C.sub.6F.sub.6 (90 ml), DMI (130 ml), tent-butyl peroxybenzoate (38.1 g, 0.196 mol) was added, and the mixture was stirred at 90° C. When the reaction was completed, 27 g (yield: 90.4%) of the product Sub 1-14c was obtained by using the separation method of Sub 1-1b.

(3) Synthesis of Sub 1-14

[0149] n, 4′-diphenyl-[1,1′: 3′, 1″-terphenyl]-4-amine (13 g, 0.05 mol), Pd.sub.2(dba).sub.3 (1.5 g, 0.0016 mol), 50% P(t-Bu)3 (1.3 g, 0.0033 mol), NaOt-Bu (15.8 g, 0.16 mol), toluene (110 ml) were added to the obtained Sub 1-14c (25 g, 0.05 mol)

[0150] and stirred at 90° C. When the reaction was completed, 35 g (yield: 82.7%) of the product Sub 1-14 was obtained by using the separation method of Sub 1-1b.

[0151] 4. Synthesis example of Sub 1-16

##STR00044##

[0152] (1) Synthesis of Sub 1-16b

[0153] Sub 1-16a (30 g, 0.11 mol), (2-(methylsulfinyl)phenyl)boronic acid (20 g, 0.11 mol), Pd(PPh.sub.3).sub.4 (3.9 g, 0.003 mol), NaOH (13.3 g, 0.33 mol), THF (220 ml) and Water (70 ml) were added and reacted for 6 hours. After the reaction was completed, 30 g (82.2%) of the product Sub 1-16b was obtained by using the separation method of Sub 1-1b.

[0154] (2) Synthesis of Sub 1-16c

[0155] The obtained Sub 1-16b (30 g, 0.09 mol) was dissolved in H.sub.2SO.sub.4 (150 ml), followed by stirring at 45° C. for 12 hours. When the reaction was completed, the reactant was slowly added to an aqueous NaOH solution and then neutralized. Then, 24 g (yield: 88.4%) of the product Sub 1-16c was obtained by using a silicagel column or recrystallization method for the resulting reactant.

(3) Synthesis of Sub 1-16

[0156] N-([1,1′-biphenyl]-4-yl)naphthalen-1-amine (29.8 g, 0.10 mol), Pd.sub.2(dba).sub.3 (2.8 g, 0.003 mol), 50% P(t-Bu)3 (2.4 g, 0.006 mol), NaOt-Bu (29.1 g, 0.3 mol), Toluene (200 ml) were added to the obtained Sub 1-16c (30 g, 0.10 mol) and stirred at 90° C. When the reaction was completed, 44 g (yield: 85.2%) of the product Sub 1-16 was obtained by using the separation method of Sub 1-1b.

5. Synthesis Example of Sub 1-26

[0157] ##STR00045##

(1) Synthesis of Sub 1-26b

[0158] Sub 1-26a (40 g, 0.17 mol), (4-chloro-1-(methylsulfinyl)naphthalen-2-yl)boronic acid (45.5 g, 0.17 mol), Pd(PPh.sub.3).sub.4 (5.9 g, 0.005 mol), NaOH (20.3 g, 0.51 mol), THF (340 ml), Water (120 ml) were added and reacted for 6 hours.

[0159] After the reaction was completed, 51 g (79.4%) of Sub 1-26b was obtained by using the separation method of Sub 1-1b.

(2) Synthesis of Sub 1-26c

[0160] The obtained Sub 1-26b (38 g, 0.10 mol) was dissolved in H.sub.2SO.sub.4 (200 ml) and stirred at 45° C. for 12 hours. When the reaction was completed, the reactant was slowly added to an aqueous NaOH solution and then neutralized. Then, 31 g (yield: 88.9%) of the product Sub 1-26c was obtained by using a silicagel column or recrystallization method for the resulting reactant.

(3) Synthesis of Sub 1-26

[0161] N-(9,9-dimethyl-9H-fluoren-3-yl)-9,9-dimethyl-9H-fluoren-2-amine (35.8 g, 0.09 mol), Pd.sub.2(dba).sub.3 (2.5 g, 0.003 mol), 50% P(t-Bu).sub.3 (2.2 g, 0.006 mol), NaOt-Bu (25.7 g, 0.3 mol), Toluene (180 ml) were added to the obtained Sub 1-26c (31 g, 0.09 mol) and stirred at 90° C. When the reaction was completed, 48 g (yield: 80.5%) of the product Sub 1-26 was obtained by using the separation method of Sub 1-1b.

6. Synthesis Example of Sub 1-35

[0162] ##STR00046##

(1) Synthesis of Sub 1-35b

[0163] Sub 1-35a (40 g, 0.17 mol), (2-chloro-6-hydroxyphenyl)boronic acid (29.2 g, 0.17 mol), Pd(PPh.sub.3).sub.4 (5.9 g, 0.005 mol), NaOH (20.3 g, 0.51 mol), THF (340 ml), Water (110 ml) were added and reacted for 6 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. After the reaction was completed, 41 g (85.3%) of Sub 1-35b was obtained by using the separation method of Sub 1-1b.

(2) Synthesis of Sub 1-35c

[0164] The obtained Sub 1-35b (40 g, 0.14 mol) was put together with Pd(OAc).sub.2 (0.95 g, 0.004 mol), 3-nitropyridine (0.53 g, 0.004 mol), dissolved in C.sub.6F.sub.6 (170 ml) and DMI (280 ml), tert-butyl peroxybenzoate (82.2 g, 0.423 mol) was added, and the mixture was stirred at 90° C. When the reaction was completed, 34 g (yield: 85.6%) of the product Sub 1-35c was obtained by using the separation method of Sub 1-1b.

(3) Synthesis of Sub 1-35

[0165] bis(9,9-dimethyl-9H-fluoren-4-yl)amine (50 g, 0.12 mol), Pd.sub.2(dba).sub.3 (3.4 g, 0.0037 mol), 50% P(t-Bu).sub.3 (3 g, 0.0075 mol), NaOt-Bu (35.9 g, 0.37 mol), toluene (250 ml) were added to the obtained Sub 1-35c (35 g, 0.12 mol) and stirred at 90° C. When the reaction was completed, 60 g (yield: 80%) of the product Sub 1-35 was obtained by using the separation method of Sub 1-1b.

7. Synthesis example of Sub 1-48

##STR00047##

(1) Synthesis of Sub 1-48b

[0166] Sub 1-48a (30 g, 0.13 mol), (1-chloro-3-hydroxynaphthalen-2-yl)boronic acid (28.3 g, 0.13 mol), Pd(PPh.sub.3).sub.4 (4.4 g, 0.004 mol), NaOH (15.3 g, 0.38 mol), THF (250 ml), and Water (80 ml) were added and reacted for 6 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. After the reaction was completed, 35 g (yield: 82.5%) of the product Sub 1-48b was obtained by using the separation method of Sub 1-1b.

(2) Synthesis of Sub 1-48c

[0167] The obtained Sub 1-48b (35 g, 0.10 mol) was put together with Pd(OAc).sub.2 (0.71 g, 0.003 mol), 3-nitropyridine (0.39 g, 0.003 mol), dissolved in C.sub.6F.sub.6 (160 ml), DMI (210 ml), tent-butyl peroxybenzoate (61.1 g, 0.32 mol) was added, and the mixture was stirred at 90° C. When the reaction was completed, 30 g (yield: 86.4%) of the product Sub 1-48c was obtained by using the separation method of Sub 1-1b.

(3) Synthesis of Sub 1-48

[0168] 9,9-dimethyl-N-(4-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine (55.5 g, 0.11 mol), Pd2(dba).sub.3 (2.9 g, 0.0032 mol), 50% P(t-Bu).sub.3 (2.6 g, 0.0064 mol), NaOt-Bu (30.5 g, 0.32 mol), toluene (210 ml) were added to the obtained Sub 1-14c (25 g, 0.05 mol) and stirred at 90° C. When the reaction was completed, 70 g (yield: 85.3%) of the product Sub 1-48 was obtained by using the separation method of Sub 1-1b.

8. Synthesis Example of Sub 1-49

[0169] ##STR00048##

(1) Synthesis of Sub 1-49b

[0170] Sub 1-49a (40 g, 0.09 mol), (2-chloro-6-hydroxyphenyl)boronic acid (15.3 g, 0.09 mol), Pd(PPh.sub.3).sub.4 (3.1 g, 0.003 mol), NaOH (10.7 g, 0.27 mol), THF (180 ml) and water (60 ml) were added and reacted for 6 hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature and the reaction solvent was removed. After the reaction was completed, 34 g (yield: 85%) of the product Sub 1-49b was obtained by using the separation method of Sub 1-1b.

(2) Synthesis of Sub 1-49c

[0171] The obtained Sub 1-49b (30 g, 0.07 mol) was put together with Pd(OAc).sub.2 (0.45 g, 0.002 mol), 3-nitropyridine (0.25 g, 0.002 mol), dissolved in C.sub.6F.sub.6 (70 ml), DMI (130 ml), tent-butyl peroxybenzoate (38.8 g, 0.2 mol) was added, and the mixture was stirred at 90° C. When the reaction was completed, 27 g (yield: 90.3%) of the product Sub 1-49c was obtained by using the separation method of Sub 1-1b.

(3) Synthesis of Sub 1-49

[0172] N-(9,9-dimethyl-9H-fluoren-3-yl)-9,9-dimethyl-9H-fluoren-1-amine (44.8 g, 0.11 mol), Pd.sub.2(dba).sub.3 (3.1 g, 0.0033 mol), 50% P(t-Bu)3 (2.7 g, 0.007 mol), NaOt-Bu (32.2 g, 0.33 mol), toluene (230 ml) were added to the obtained Sub 1-49c (50 g, 0.11 mol) and stirred at 90° C. When the reaction was completed, 74 g (yield: 86.2%) of the product Sub 1-49 was obtained by using the separation method of Sub 1-1b.

[0173] The compound belonging to Sub 1 may be the following compounds, but is not limited thereto, and Table 1 below shows FD-MS values of the compounds belonging to Sub 1.

##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055## ##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065## ##STR00066##

TABLE-US-00002 TABLE 1 compound FD-MS compound FD-MS Sub1-1 m/z = 369.09(C.sub.24H.sub.16CINO = 369.85) Sub1-2 m/z = 369.09(C.sub.24H.sub.16CINO = 369.85) Sub1-3 m/z = 521.15(C.sub.36H.sub.24CINO = 522.04) Sub1-4 m/z = 446.12(C.sub.29H.sub.19CIN.sub.2O = 446.93) Sub1-5 m/z = 571.1 7(C.sub.40H.sub.26CINO = 572.1) Sub1-6 m/z = 613.16(C.sub.42H.sub.28CINS = 614.2) Sub1-7 m/z = 485.1 (C.sub.32H.sub.20CINS = 486.03) Sub1-8 m/z = 669.14(C.sub.44H.sub.28CINS.sub.2 = 670.29) Sub1-9 m/z = 385.07(C.sub.24H.sub.16CINS = 385.91) Sub1-10 m/z = 369.09(C.sub.24H.sub.16CINO = 369.85) Sub1-11 m/z = 537.13(C.sub.36H.sub.24CINS = 538.11) Sub1-12 m/z = 419.08(C.sub.26Hi4CIN.sub.3O = 419.87) Sub1-13 m/z = 513.19(C.sub.35H.sub.28CINO = 514.07) Sub1-14 m/z = 773.25(C56H.sub.36CINO = 774.36) Sub1-15 m/z = 495.14(C.sub.34H.sub.22CINO = 496.01) Sub1-16 m/z = 511.12(C34H.sub.22CINS = 512.07) Sub1-17 m/z = 419.11 (C.sub.28H.sub.18CINO = 419.91) Sub1-18 m/z = 561.13(C38H.sub.24CINS = 562.13) Sub1-19 m/z = 552.14(C.sub.36H.sub.25CIN.sub.2S = 553.12) Sub1-20 m/z = 552.14(C.sub.36H.sub.25CIN.sub.2S = 553.12) Sub1-21 m/z = 485.15(C.sub.33H.sub.24CINO = 486.01) Sub1-22 m/z = 419.11 (C.sub.28H.sub.18CINO = 419.91) Sub1-23 m/z = 617.19(C.sub.42H.sub.32CINS = 618.24) Sub1-24 m/z = 741 23(C.sub.52H.sub.36CINS = 742.38) Sub1-25 m/z = 801,23(C.sub.57H.sub.36CINS = 802.43) Sub1-26 m/z = 667.21 (C.sub.46H.sub.34CINS = 668.3) Sub1-27 m/z = 667.21 (C.sub.46H.sub.34CINS = 668.3) Sub1-28 m/z = 739.21 (C.sub.52H.sub.34CINS = 740.36) Sub1-29 m/z = 823.26(C.sub.60H.sub.38CINO = 824.42) Sub1-30 m/z = 927.33(C.sub.68H.sub.46CINO = 928.57) Sub1-31 m/z = 601.22(C.sub.42H.sub.32CINO = 602.17) Sub1-32 m/z = 844.32(C.sub.60H.sub.45CIN.sub.20 = 845.48) Sub1-33 m/z = 1001.34(C.sub.74H.sub.48CINO = 1002.65) Sub1-34 m/z = 601.22(C.sub.42H.sub.32CINO = 602.17) Sub1-35 m/z = 601.22(C.sub.42H.sub.32CINO = 602.17) Sub1-36 m/z = 601.22(C.sub.42H.sub.32CINO = 602.17) Sub1-37 m/z = 717.23(C.sub.50H.sub.36CINS = 718.36) Sub1-38 m/z = 791,24(C.sub.56H.sub.38CINS = 792.44) Sub1-39 m/z = 958.31 (C.sub.68H.sub.47CIN.sub.2S = 959.65) Sub1-40 m/z = 617.19(C.sub.42H.sub.32CINS = 618.24) Sub1-41 m/z = 617.19(C.sub.42H.sub.32CINS = 618.24) Sub1-42 m/z = 741,23(C.sub.52H.sub.36CINS = 742.38) Sub1-43 m/z = 617.19(C.sub.42H.sub.32CINS = 618.24) Sub1-44 m/z = 601.22(C.sub.42H.sub.32CINO = 602.17) Sub1-45 m/z = 601.22(C.sub.42H.sub.32CINO = 602.17) Sub1-46 m/z = 723.23(C.sub.52H.sub.34CINO = 724.3) Sub1-47 m/z = 601.22(C.sub.42H.sub.32CINO = 602.17) Sub1-48 m/z = 775.26(C.sub.56H.sub.38CINO = 776.38) Sub1-49 m/z = 768.29(C.sub.54H.sub.41CIN.sub.2O = 769.39) Sub1-50 m/z = 865.26(C.sub.62H.sub.40CINS = 866.52) Sub1-51 m/z = 617.19(C.sub.42H.sub.32CINS = 618.24) Sub1-52 m/z = 703.24(C.sub.48H.sub.34CIN.sub.3O = 704.27) Sub1-53 m/z = 985.38(C.sub.70H.sub.52CIN.sub.3O = 986.66) Sub1-54 m/z = 1051.37(C.sub.74H.sub.54CIN.sub.3S = 1052.78) Sub1-55 m/z = 1008.38(C.sub.73H.sub.53CIN.sub.2O = 1009.69)

[0174] Meanwhile, the compound belonging to Sub 2 may be the following compounds, but is not limited thereto, and Table 2 below shows FD-MS values of the compounds belonging to Sub 2.

##STR00067## ##STR00068## ##STR00069## ##STR00070## ##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077## ##STR00078## ##STR00079##

TABLE-US-00003 TABLE 2 compound FD-MS compound FD-MS Sub2-1 m/z = 477.25(C.sub.36H.sub.31N = 477.65) Sub2-2 m/z = 401.21(C.sub.3oH27N = 401.55) Sub2-3 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-4 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-5 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-6 m/z = 429.25(C.sub.32H.sub.31N = 429.61) Sub2-7 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-8 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-9 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-10 m/z = 45123(C.sub.34H.sub.29N = 451.61) Sub2-11 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-12 m/z = 401.21(C.sub.30H.sub.27N = 401.55) Sub2-13 m/z = 525.25(C.sub.40H.sub.31N = 525.7) Sub2-14 m/z = 549.25(C.sub.42H.sub.31N = 549.72) Sub2-15 m/z = 647.26(C.sub.50H.sub.33N = 647.82) Sub2-16 m/z = 725.31(C.sub.56H.sub.39N = 725.94) Sub2-17 m/z = 649.28(C.sub.50H.sub.35N = 649.84) Sub2-18 m/z = 649.28(C.sub.50H.sub.35N = 649.84) Sub2-19 m/z = 48128(C.sub.36H.sub.35N = 481.68) Sub2-20 m/z = 645.25(C.sub.50H.sub.31N = 645.81) Sub2-21 m/z = 649.28(C.sub.50H35N = 649.84) Sub2-22 m/z = 649.28(C.sub.50H.sub.35N = 649.84) Sub2-23 m/z = 677.31(C.sub.52H.sub.39N = 677.89) Sub2-24 m/z = 451.23(C.sub.34H.sub.29N = 451.61) Sub2-25 m/z = 285.15(C.sub.2H.sub.19N = 285.39) Sub2-26 m/z = 219.1(C.sub.16H.sub.13N = 219.29) Sub2-27 m/z = 295.14(C.sub.22H.sub.17N = 295.39) Sub2-28 m/z = 245.12(C.sub.18H.sub.15N = 245.33) Sub2-29 m/z = 321.15(C.sub.24H.sub.19N = 321.42) Sub2-30 m/z = 335.17(C.sub.25H.sub.21N = 335.45) Sub2-31 m/z = 345.15(C.sub.26H19N = 345.45) Sub2-32 m/z = 169.09(C.sub.12H.sub.11N = 169.23) Sub2-33 m/z = 205.07(C.sub.12H.sub.9F.sub.2N = 205.21) Sub2-34 m/z = 250.15(C.sub.18H.sub.10D.sub.5N = 250.36) Sub2-35 m/z = 361.18(C.sub.27H.sub.23N = 361.49) Sub2-36 m/z = 371.17(C.sub.28H.sub.21N = 371.48) Sub2-37 m/z = 295.14(C.sub.22H.sub.17N = 295.39) Sub2-38 m/z = 423.16(C.sub.31H.sub.21NO = 423.52) Sub2-39 m/z = 245.12(C.sub.18H.sub.15N = 245.33) Sub2-40 m/z = 321.15(C.sub.24H.sub.19N = 321.42) Sub2-41 m/z = 575.26(C.sub.44H.sub.33N = 575.76)

II. Synthesis of Product

1. Synthesis Example of P-2

[0175] ##STR00080##

[0176] Sub 1-2 (30 g, 0.08 mol) and Sub 2-2 (32.5 g, 0.08 mol), Pd.sub.2(dba)3 (2.2 g, 0.0024 mol), 50% P(t-Bu).sub.3 (2.0 g, 0.005 mol), NaOt-Bu (23.4 g, 0.24 mol), toluene (150 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 50 g of product P-2 (yield: 84%) was obtained by concentrating the reaction product and then recrystallizing the resulting compound through a silicagel column and recrystallization method.

2. Synthesis Example of P-9

[0177] ##STR00081##

[0178] Sub 1-48 (50 g, 0.06 mol) and Sub 2-32 (10.9 g, 0.06 mol), Pd.sub.2(dba).sub.3 (1.8 g, 0.0019 mol), 50% P(t-Bu)3 (1.6 g, 0.004 mol), NaOt-Bu (18.6 g, 0.19 mol), toluene (130 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 48 g (yield: 82%) of the product P-9 was obtained through the separation method of P-1.

3. Synthesis Example of P-20

[0179] ##STR00082##

[0180] Sub 1-21 (50 g, 0.10 mol) and Sub 2-3 (41.3 g, 0.10 mol), Pd.sub.2(dba).sub.3 (2.8 g, 0.003 mol), 50% P(t-Bu).sub.3 (2.5 g, 0.006 mol), NaOt-Bu (30 g, 0.31 mol), toluene (160 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 80 g (yield: 91.4%) of the product P-20 was obtained through the separation method of P-1.

4. Synthesis Example of P-26

[0181] ##STR00083##

[0182] Sub 1-10 (50 g, 0.14 mol) and Sub 2-3 (54.2 g, 0.14 mol), Pd.sub.2(dba).sub.3 (3.7 g, 0.004 mol), 50% P(t-Bu).sub.3 (3.3 g, 0.008 mol), NaOt-Bu (39 g, 0.41 mol), toluene (200 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 80 g (yield: 80.6%) of the product P-26 was obtained through the separation method of P-1.

5. Synthesis Example of P-29

[0183] ##STR00084##

[0184] Sub 1-23 (35 g, 0.06 mol) and Sub 2-25 (16.2 g, 0.06 mol), Pd.sub.2(dba).sub.3 (1.6 g, 0.002 mol), 50% P(t-Bu).sub.3 (1.4 g, 0.004 mol), NaOt-Bu (16.3 g, 0.17 mol), toluene (130 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 40 g (yield: 81.5%) of the product P-29 was obtained through the separation method of P-1.

6. Synthesis Example of P-34

[0185] ##STR00085##

[0186] Sub 1-26 (35 g, 0.05 mol) and Sub 2-27 (15.5 g, 0.06 mol), Pd.sub.2(dba).sub.3 (1.4 g, 0.002 mol), 50% P(t-Bu).sub.3 (1.3 g, 0.004 mol), NaOt-Bu (15.1 g, 0.16 mol), toluene (100 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 41 g (yield: 84.4%) of the product P-34 was obtained through the separation method of P-1.

7. Synthesis Example of P-42

[0187] ##STR00086##

[0188] Sub 1-9 (40 g, 0.10 mol) and Sub 2-20 (66.9 g, 0.10 mol), Pd.sub.2(dba).sub.3 (2.8 g, 0.003 mol), 50% P(t-Bu).sub.3 (2.5 g, 0.006 mol), NaOt-Bu (29.9 g, 0.31 mol), toluene (180 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 87 g (yield: 84.3%) of the product P-42 was obtained through the separation method of P-1.

8. Synthesis Example of P-47

[0189] ##STR00087##

[0190] Sub 1-19 (38 g, 0.07 mol) and Sub 2-18 (44.6 g, 0.07 mol), Pd.sub.2(dba).sub.3 (1.9 g, 0.002 mol), 50% P(t-Bu).sub.3 (1.7 g, 0.004 mol), NaOt-Bu (19.8 g, 0.21 mol), toluene (160 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 72 g (yield: 89.8%) of the product P-47 was obtained through the separation method of P-1.

9. Synthesis Example of P-58

[0191] ##STR00088##

[0192] Sub 1-53 (50 g, 0.05 mol) and Sub 2-32 (8.6 g, 0.05 mol), Pd.sub.2(dba).sub.3 (1.4 g, 0.002 mol), 50% P(t-Bu).sub.3 (1.2 g, 0.003 mol), NaOt-Bu (14.6 g, 0.15 mol), toluene (100 ml) were added to a round flask and stirred at 124° C. When the reaction was completed, 50 g (yield: 88.1%) of the product P-58 was obtained through the separation method of P-1.

[0193] Meanwhile, the FD-MS values of the compounds P-1 to P-60 of the present invention prepared according to the above synthesis examples are shown in Table 3.

TABLE-US-00004 TABLE 3 compound FD-MS compound FD-MS P-1 m/z = 910.39(C.sub.68H.sub.50N.sub.2O = 911.16) P-2 m/z = 734.33(C54H.sub.42N.sub.2O = 734.94) P-3 m/z = 1010.42(C.sub.76H.sub.54N.sub.2O = 1011.28) P-4 m/z = 959.39(C.sub.71H.sub.49N.sub.3O = 960.19) P-5 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-6 m/z = 892.33(C.sub.64H.sub.42F.sub.2N.sub.2O = 893.05) P-7 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-8 m/z = 1030.39(C.sub.78H.sub.50N.sub.2O = 1031.27) P-9 m/z = 908.38(C.sub.68H.sub.48N.sub.2O = 909.15) P-10 m/z = 1215.52(C.sub.92H.sub.57D.sub.5N.sub.2O = 1216.55) P-11 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-12 m/z = 1012.44(C.sub.76H.sub.56N.sub.2O = 1013.3) P-13 m/z = 926.42(C.sub.69H.sub.54N.sub.2O = 927.2) P-14 m/z = 936.41(C.sub.70H.sub.52N.sub.2O = 937.2) P-15 m/z = 1032.38(C.sub.76H.sub.48N.sub.4O = 1033.25) P-16 m/z = 878.42(C.sub.65H.sub.54N.sub.2O = 879.16) P-17 m/z = 1166.52(C.sub.88H.sub.6N.sub.2O = 1167.51) P-18 m/z = 1184.47(C.sub.90H.sub.60N.sub.2O = 1185.48) P-19 m/z = 1032.41(C.sub.78H.sub.52N.sub.2O = 1033.29) P-20 m/z = 850.39(C.sub.63H.sub.50N.sub.2O = 851.1 P-21 m/z = 956.38(C.sub.72H48N.sub.2O = 957.19) P-22 m/z = 1060.44(C.sub.80H.sub.56N.sub.2O = 1061.34) P-23 m/z = 1231.51(C.sub.91H.sub.65N.sub.3O.sub.2 = 1232.54) P-24 m/z = 1027.45(C.sub.76H.sub.57N.sub.3O = 1028.31) P-25 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-26 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-27 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-28 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-29 m/z = 866.37(C.sub.63H.sub.50N.sub.2S = 867.17) P-30 m/z = 874.34(C.sub.64H.sub.46N.sub.2S = 875.15) P-31 m/z = 1048.39(C.sub.78H.sub.52N.sub.2S = 1049.35) P-32 m/z = 982.43(C.sub.72H.sub.58N.sub.2S = 983.33) P-33 m/z = 934.34(C.sub.69H.sub.46N.sub.2S = 935.2) P-34 m/z = 926.37(C.sub.68H.sub.50N.sub.2S = 927.22) P-35 m/z = 1082.46(C.sub.80H.sub.62N.sub.2S = 1083.45) P-36 m/z = 1254.49(C.sub.94H.sub.66N.sub.2S = 1255.64) P-37 m/z = 850.34(C.sub.62H.sub.46N.sub.2S = 851.12) P-38 m/z = 1114.44(C.sub.80H.sub.62N.sub.2S.sub.2 = 1115.51) P-39 m/z = 948.35(C.sub.70H.sub.48N.sub.2S = 949.23) P-40 m/z = 1002.4(C.sub.74H.sub.54N.sub.2S = 1003.32) P-41 m/z = 924.35(C.sub.68H.sub.48N.sub.2S = 925.21) P-42 m/z = 994.34(C.sub.74H.sub.46N.sub.2S = 995.26) P-43 m/z = 1150.43(C.sub.86H.sub.58N.sub.2S = 1151.48) P-44 m/z = 1257.51(C.sub.93H.sub.67N.sub.3S = 1258.64) P-45 m/z = 926.37(C.sub.68H.sub.50N.sub.2S = 927.22) P-46 m/z = 926.37(C.sub.68H.sub.50N.sub.2S = 927.22) P-47 m/z = 1165.44(C.sub.86H.sub.59N.sub.3S = 1166.5) P-48 m/z = 1091.43(C.sub.80H.sub.57N.sub.3S = 1092.42) P-49 m/z = 750.31(C.sub.54H.sub.42N.sub.2S = 751) P-50 m/z = 750.31(C.sub.54H.sub.42N.sub.2S = 751) P-51 m/z = 950.37(C.sub.70H.sub.50N.sub.2S = 951.24) P-52 m/z = 902.37(C.sub.66H.sub.50N.sub.2S = 903.2) P-53 m/z = 734.33(C.sub.54H.sub.42N.sub.2O = 734.94) P-54 m/z = 988.4(C.sub.73H.sub.52N.sub.2O.sub.2 = 989.23) P-55 m/z = 1129.44(C.sub.83H.sub.59N.sub.3S = 1130.47) P-56 m/z = 1156.44(C.sub.85H.sub.60N.sub.2OS = 1157.49) P-57 m/z = 1068.48(C.sub.78H.sub.60N.sub.40 = 1069.37) P-58 m/z = 1118.49(C.sub.82H.sub.62N.sub.4O = 1119.43) P-59 m/z = 1184.49(C.sub.86H.sub.64N.sub.4S = 1185.55) P-60 m/z = 1141.5(C.sub.85H.sub.63N.sub.3O = 1142.46)

Example 1

Green Organic Light Emitting Device (Emitting Auxiliary Layer)

[0194] First, on an ITO layer (anode) formed on a glass substrate, N.sup.1-(naphthalen-2-yl)-N.sup.4, N.sup.4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N.sup.1-phenylbenzene-1,4-diamine (Hereinafter, abbreviated as 2-TNATA) film as a hole injection layer was vacuum-deposited to form a thickness of 60 nm. Subsequently, 4,4-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter abbreviated as -NPD) as a hole transport corn pound was vacuum-deposited on the film to a thickness of 60 nm to form a hole transport layer. Then, as a material for the emitting auxiliary layer, the compounds represented by Formula 1 and Comparative Example were vacuum-deposited to a thickness of 20 nm to form an emitting auxiliary layer. After forming the emitting auxiliary layer, CBP[4,4′-N,N′-dicarbazole-biphenyl] was used as a host material, and Ir(ppy)3 [tris(2-phenylpyridine)-iridium] was used as a dopant material, doped at a weight ratio of 95:5, and vacuum deposited to a thickness of 30 nm to form an emitting layer on the emitting auxiliary layer. (1,1′-bisphenyl)-4-oleato)bis(2-methyl-8-quinolineoleato)aluminum (hereinafter abbreviated as BAlq) as a hole blocking layer was vacuum-deposited to a thickness of 10 nm, as an electron transport layer, tris(8-quinolinol)aluminum (hereinafter, abbreviated as Alq3) was deposited to a thickness of 40 nm. Thereafter, LiF, which is an alkali metal halide, was deposited as an electron injection layer to a thickness of 0.2 nm, and then Al was deposited to a thickness of 150 nm and used as a cathode to prepare an organic electroluminescent device.

Example 2 to Example 17

[0195] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound of the present invention described in Table 4 was used instead of the compound P-2 of the present invention as an emitting auxiliary layer material.

Comparative Example 1

[0196] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the emitting auxiliary layer was not used.

Comparative Example 2 to Comparative Example 3

[0197] An organic electroluminescent device was manufactured in the same manner as in Example 1, except that comparative compounds A to B were used instead of the compound P-2 of the present invention as an emitting auxiliary layer material.

##STR00089##

[0198] By applying a forward bias DC voltage to the organic electroluminescent devices prepared in Examples and Comparative Examples prepared in this way, Electroluminescence (EL) characteristics were measured with PR-650 from Photoresearch, and as a result of the measurement, the T95 lifetime was measured using a lifetime measuring device manufactured by McScience at 5000 cd/m.sup.2 standard luminance. Table 4 below shows the device fabrication and evaluation results.

TABLE-US-00005 TABLE 4 Current Density Brightness Efficiency CIE compound Voltage (mA/cm.sup.2) (cd/m.sup.2) (cd/A) T(95) x y comparative — 6.4 17.8 5000 28.1 99.4 0.34 0.61 example(1) comparative comparative 6.3 15.3 5000 32.7 105.9 0.34 0.64 example(2) compound A comparative comparative 6.0 13.7 5000 36.4 114.9 0.33 0.65 example(3) compound B example(1) P-2 4.9 8.9 5000 56.2 133.0 0.33 0.65 example(2) P-5 4.9 9.0 5000 55.3 132.3 0.33 0.64 example(3) P-7 5.0 9.5 5000 52.7 130.2 0.33 0.64 example(4) P-10 5.1 10.1 5000 49.3 129.5 0.33 0.64 example(5) P-20 5.3 10.3 5000 48.4 128.1 0.33 0.65 example(6) P-21 5.2 10.5 5000 47.6 128.8 0.33 0.65 example(7) P-25 5.0 9.3 5000 53.6 130.9 0.33 0.65 example(8) P-26 4.9 9.2 5000 54.5 131.6 0.33 0.65 example(9) P-29 4.8 9.8 5000 51.0 125.9 0.33 0.65 example(10) P-31 5.1 10.7 5000 46.7 123.8 0.33 0.65 example(11) P-35 5.0 11.8 5000 42.4 122.4 0.33 0.65 example(12) P-39 5.2 10.9 5000 45.8 124.5 0.33 0.65 example(13) P-42 5.3 11.3 5000 44.1 123.1 0.33 0.65 example(14) P-47 5.3 11.6 5000 43.2 121.7 0.33 0.64 example(15) P-50 4.8 9.6 5000 51.9 126.6 0.33 0.65 example(16) P-52 5.2 10.0 5000 50.1 125.2 0.33 0.65 example(17) P-57 5.4 11.1 5000 45.0 127.4 0.33 0.64

[0199] As can be seen from the results in Table 4, when manufacturing a green organic electronic element using the material for an organic electronic element of the present invention as an emitting auxiliary layer material, it can be seen that not only can the driving voltage of the organic electroluminescent device be lowered, but also the luminous efficiency and lifespan are remarkably improved compared to Comparative Examples in which no emitting auxiliary layer is used or Comparative Compounds A to B are used. Comparing the results of Comparative Examples 2 to 3, it can be seen that as fluorene is substituted for the amino group, the driving voltage is pulled, the efficiency is increased, and the lifespan is increased. Comparing with the compounds of Examples 1 to 17 corresponding to Formula 1 of the present patent, 2 or more fluorene groups are substituted in the substituents of the amino group. As the fluorene groups are substituted in this way, the overall HOMO level can be raised. When a plurality of fluorenes are substituted, the effect is doubled and the hole injection characteristic from the hole transport layer can be improved. In addition, by substituting a fluorene group with strong hole characteristics for an amine, the stability of the hole is increased, and thus the lifespan of the device as a whole is also increased. And compared with a simple aryl group, the fluorene group has a plate-like structure on the structure, and this plate-like structure improves hole mobility in the overall device and pulls the driving voltage.

[0200] Comparing the device results of Examples 1 to 17, the driving voltage, efficiency, and lifespan characteristics are different depending on the type of element included in the linker. In more detail, when the element of the Linker is S, the overall driving voltage and efficiency characteristics are excellent, but it can be seen that the lifespan characteristics are lowered compared to Linker containing the element O. Moreover, it can be seen that different characteristics are shown depending on the bonding position of the amine bonded to Linker, and these characteristics show different hole characteristics depending on the position of the amine.

[0201] Although exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims. Therefore, the embodiment disclosed in the present invention is intended to illustrate the scope of the technical idea of the present invention, and the scope of the present invention is not limited by the embodiment. The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention.

INDUSTRIAL APPLICABILITY

[0202] According to the present invention, it is possible to manufacture an organic device having excellent device characteristics of high luminance, high light emission and long lifespan, and thus there is industrial applicability.