KR20150095545A - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic light emitting compound represented by [Formula 1]. An organic electroluminescent device comprising the organic light emitting compound is capable of low-voltage driving and shows excellent lifespan characteristics and color purity, thereby being used in a variety of display devices and illumination devices.

Description

TECHNICAL FIELD The present invention relates to an organic electroluminescent compound and an electroluminescent device comprising the same,

The present invention relates to an organic light emitting compound and an organic electroluminescent device including the same, which can be driven at a lower voltage, have excellent long life characteristics, and have improved blue color purity.

A material used as an organic material layer in an organic electroluminescent device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The luminescent material has blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.

Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

However, in order to sufficiently exhibit the excellent characteristics of the organic electroluminescent device described above, a material constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, However, the development of a stable and efficient organic material layer material for an organic light emitting device has not yet been sufficiently developed, and therefore, the development of new materials has been continuously required.

In particular, it is inevitably necessary to solve the problems of high drive voltage and low lifetime characteristics of the anthracene-based compound, and it is inevitable to solve the low blue color purity of the pyrene-based arylamine compound.

Accordingly, it is an object of the present invention to provide a novel organic electroluminescent compound which has improved voltage driving characteristics and a longer life than conventional anthracene-based host compounds and can realize an improved blue color purity compared to a styreneprene-based arylamine dopant compound and an organic electroluminescent device ≪ / RTI >

The present invention provides an organic electroluminescent compound represented by the following formula (I) and an organic electroluminescent device including the organic electroluminescent compound.

(I)

Specific substituents of the above formula (I) will be described later.

The organic electroluminescent device including the organic electroluminescent compound according to the present invention can be applied to various display devices and lighting devices for achieving full color because of being capable of being driven at a low voltage and having excellent power efficiency and excellent lifetime characteristics and blue color purity. have.

1 is a schematic view of an organic electroluminescent device according to one embodiment of the present invention.

Hereinafter, the present invention will be described in more detail.

The present invention relates to an organic electroluminescent compound represented by the following formula (I), which can improve the low-voltage driving, longevity and color purity of an organic electroluminescent device, and more particularly to a compound represented by the following formula And can be used as a host compound or a dopant compound in the light emitting layer depending on the substituent to be introduced.

(I)

In the above formula (I)

X is NR _11, O, S, or SiR ₁₂ R _13.

A ₁ and A ₂ are the same or different and are each independently an aromatic ring or a heteroaromatic ring and at least one of A ₁ and A ₂ is a heteroaromatic ring containing at least one N.

Z ₁ and Z ₂ are the same or different from each other and each independently represents a monovalent or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- to 6-membered heteroaromatic ring fused with an aromatic ring, A 6-membered heteroaromatic ring may be selected from the fused monocyclic or polycyclic aromatic rings.

R ₁ to R ₁₀ and R ₁₁ to R ₁₃ are the same or different and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms , A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted hetero atom, O, N , A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C2- A substituted or unsubstituted aryloxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkylamine group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon number 5 A substituted or unsubstituted C1 to C30 arylamine group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C5 to C30 arylsilyl group, a cyano group, a nitro group, a hydroxy group and a halogen group And R ₁ to R ₁₃ may combine with each other or adjacent substituents to form a saturated or unsaturated ring.

According to an embodiment of the present invention, R ₁ to R ₁₃ may be further substituted with one or more substituents, and the one or more substituents may be deuterium, cyano, halogen, hydroxyl, nitro, A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms An aryloxy group having 2 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 3 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylamino group having 3 to 24 carbon atoms An arylsilyl group having 3 to 24 carbon atoms and an aryloxy group having 3 to 24 carbon atoms.

및

는 서로 동일하거나 상이하며, 각각 독립적으로 하기 C1 내지 C15 중에서 선택되는 어느 하나일 수 있다.According to a preferred embodiment of the present invention,

And

May be the same or different from each other and each independently selected from the following C1 to C15.

C1 C2 C3 C4

C5 C6 C7 C8

C9 C10 C11 C12

C13 C14 C15

In the above C1 to C15,

Wherein A ₁ to A ₁₀ are the same as or different from each other and each independently N or CR, R and R 'are the same as defined for R ₁ to R _{13 in} the above formula (I) .

In the above formula (I), R ₁ to R ₁₀ are the same as or different from each other, and more specifically each independently represents hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, substituted or unsubstituted C1- A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, A substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a group represented by the following formula (Q).

[Structural formula Q]

In the above formula [Q]

* Means a site which binds to R ₁ to R ₁₀ of the above formula (I).

L is a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2-C60 heteroarylene group in which at least one unsubstituted C1-C60 arylene group and at least one substituted or unsubstituted C3-C30 cycloalkyl are fused, and n is 0 And when n is 2, a plurality of Ls may be the same or different from each other.

Ar ₁ to Ar ₂ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms An aryl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having at least one heteroatom selected from O, N, S and P, and Ar ₁ to Ar ₂ may be the same or different from each other or adjacent substituents To form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero.

R ₉ and R ₁₀ are each a substituent represented by the above formula [Q], and R ₉ and R ₁₀ may be the same or different from each other.

In the above structural formula Q, Ar ₁ and Ar ₂ may each independently be any one selected from the following [substituent B1] to [substituent B46].

[Substituent B1] [Substituent B2] [Substituent B3]

[Substituent B4] [Substituent B5] [Substituent B6]

[Substituent B7] [Substituent B8] [Substituent B9]

[Substituent B10] [Substituent B11] [Substituent B12]

[Substituent B13] [Substituent B14] [Substituent B15]

[Substituent B16] [Substituent B17] [Substituent B18]

[Substituent B19] [Substituent B20] [Substituent B21]

[Substituent B22] [Substituent B23] [Substituent B24]

[Substituent B25] [Substituent B26] [Substituent B27]

[Substituent B28] [Substituent B29] [Substituent B30]

[Substituent B31] [Substituent B32] [Substituent B33]

[Substituent B34] [Substituent B35] [Substituent B36]

[Substituent B37] [Substituent B38] [Substituent B39]

[Substituent B40] [Substituent B41] [Substituent B42]

[Substituent B43] [Substituent B44] [Substituent B45]

[Substituent B46]

In the above [substituents B1] to [substituent B46]

R represents a hydrogen atom, a heavy hydrogen atom, a cyano group, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, A silyl group, an arylsilyl group having 6 to 18 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, and n is 0 to 12 And when n is 2 or more, a plurality of R's are the same as or different from each other, and may form a ring by fusing with adjacent substituents.

On the other hand, the aryl group which is a substituent used in the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and includes a single or fused ring system containing 5 to 7 atoms, preferably 5 or 6 atoms, When a substituent is present in the aryl group, the adjacent substituent may be fused with each other to form a ring.

Specific examples of the aryl include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, an o- Naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, pyranyl group, An aromatic group such as a phenyl group, an indenyl group, a fluorenyl group, a tetrahydronaphthyl group, a pyrenyl group, a perylene group, a crycenyl group, a naphthacenyl group and a fluoranthenyl group.

At least one hydrogen atom of the aryl group may be replaced by a substituent selected from the group consisting of a deuterium atom, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH (R) 'And R''each independently represent an alkyl group having 1 to 10 carbon atoms, which is referred to as an "alkylamino group" in this case), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, A halogenated alkyl group having 1 to 24 carbon atoms, an alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, A heteroaryl group having 2 to 24 carbon atoms or a heteroarylalkyl group having 2 to 24 carbon atoms.

The heteroaryl group which is a substituent used in the present invention may be any one selected from the following Structural Formulas 1 to 6:

[Structural formula 1] [Structural formula 2]  [Structural Formula 3]

[Structural Formula 4] [Structural Formula 5]  [Structural Formula 6]

In the above Structural Formulas 1 to 6,

T ₁ to T ₈ may be the same or different and each independently selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ) , R ₃₁ to R ₄₄ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, An aryl group having 5 to 50 carbon atoms, and a heteroaryl group having 2 to 50 carbon atoms having a substituted or unsubstituted heteroatom, O, N or S, may be used.

In each of [Structural Formula 1] to [Structural Formula 6] above, R ₃₁ to R ₄₄ May be bonded to an alicyclic group in the above formula (I) to form a single bond. As a specific example, when X of formula (I) is NR ₁₁ and R ₁₁ is a heteroaryl group, it may be selected from among the above-mentioned structures [1] to [6].

The above-mentioned [formula 3] may include a compound represented by the following formula [3] by a resonance structure according to the movement of electrons.

[Structural Formula 3-1]

In the above structural formula 3-1, T ₁ to T ₅ and R ₃₃ and R ₃₄ are the same as defined above.

Further, according to a preferred embodiment of the present invention, the above Structural Formulas 1 to 6 can be selected from the following Structural Formula 7.

[Structural Formula 7]

In the above formula 7,

X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, an unsubstituted or substituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C5-C30 cycloalkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms An amino group, a substituted or unsubstituted aryl group having 5 or more carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S and P as a hetero atom, a cyano group, a nitro group, And m is an integer of 1 to 11. When m is 2 or more, a plurality of X's are the same or different from each other, and any one of the at least one X is selected from the group consisting of R ₁ to R _{4 in the} formula (I) R ₁₃ , Z ₁ to Z _2, and any of these substituents to form a single bond.

Specific examples of the alkyl group as the substituent used in the present invention 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, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " alkylsilyl group "hereinafter), a substituted or unsubstituted amino group _{(-NH 2, -NH (R)} , -N (R ') (R"), where R, R' and R "are independently C 1 each A hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, An alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, An aryl group having from 5 to 24 carbon atoms, an aryl group having from 5 to 24 carbon atoms, an arylalkyl group having from 6 to 24 carbon atoms, a heteroaryl group having from 3 to 24 carbon atoms, or a heteroarylalkyl group having from 3 to 24 carbon atoms.

Specific examples of the alkoxy group used in the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And may be substituted with the same substituents as those in the case of the alkyl group.

Specific examples of the halogen group which is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br) and the like.

The aryloxy group which is a substituent used in the present invention means an -O-aryl radical, wherein the aryl group is as defined above, and specific examples thereof include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy and the like, and at least one hydrogen atom contained in the aryloxy group may be further substituted.

Specific examples of the silyl group used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, silyl, diphenylvinylsilyl, methylcyclobutylsilyl , Dimethyl furyl silyl and the like.

Specific examples of the alkenyl group used in the present invention include straight chain or branched chain alkenyl groups and include 3-pentenyl, 4-hexenyl, 5-heptenyl, 4-methyl- Dimethyl-pentenyl group, 6-methyl-5-heptenyl group and 2,6-dimethyl-5-heptenyl group.

In the present invention, the 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an alkoxy group having 1 to 24 carbon atoms, An arylsilyl group having 1 to 24 carbon atoms, an aryloxy group having 1 to 24 carbon atoms, germanium, phosphorus, and boron.

The carbon number of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 5 to 50 carbon atoms', etc., Quot; means the total number of carbon atoms constituting the alkyl moiety or the aryl moiety when it is regarded as unsubstituted. For example, a phenyl group substituted with a butyl group at the para position means an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

According to a preferred embodiment of the present invention, the organic luminescent compound represented by the formula (I) may be any one selected from the following [compounds 1] to [41].

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41]

In addition, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, May contain one or more kinds of luminescent compounds.

The organic layer containing the organic luminescent compound of the present invention may include at least one of a hole injecting layer, a hole transporting layer, a functional layer having both a hole injecting function and a hole transporting function, a light emitting layer, an electron transporting layer, have. At this time, the organic layer interposed between the first electrode and the second electrode may include a light emitting layer, and the light emitting layer is composed of a host and a dopant, and the organic light emitting compound of Formula (I) Or as a dopant.

In the present invention, the light emitting layer may further include a host or a dopant material together with the compound represented by Formula (I) according to the present invention, and the content of the dopant in the light emitting layer is usually about 100 parts by weight of the host About 0.01 to about 20 parts by weight, based on the total weight of the composition.

In the present invention, as the electron transporting layer material, a known electron transporting material can be used, which functions to stably transport electrons injected from an electron injection electrode (cathode). Examples of electron transport materials are known, a quinoline derivative, in particular tris (8-quinolinolato) aluminum (Alq _3), TAZ, Balq, beryllium bis (benzo-10-quinolinyl furnace benzoate) (beryllium bis (10-benzoquinolin -olate: Bebq ₂ ), ADN, [Compound 201], [Compound 202], BCP, and oxadiazole derivative PBD, BMD, BND and the like may be used.

TAZ BAlq

[Compound 201] [Compound 202] BCP

Further, the electron transporting layer used in the present invention can be used as the organometallic compound represented by the following formula (C) alone or in combination with the electron transporting layer material.

≪ RTI ID = 0.0 &

In the above formula (C)

Y is a moiety selected from C, N, O and S, which is directly bonded to M to form a single bond, and any moiety selected from C, N, O and S is a moiety coordinating to M And is a ligand chelated by coordination bond with the single bond.

M is an alkali metal, an alkaline earth metal, an aluminum (Al), or a boron (B) atom.

OA is a monovalent ligand capable of single bond or coordination bond with M, O is oxygen, A is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, Substituted or unsubstituted C2-C30 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C5-C30 cycloalkyl, An alkenyl group, and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom O, N, or S.

When m is 1 or n = 0 when M is one metal selected from alkali metals and m is 1 or n = 1 when M is a metal selected from alkaline earth metals, or m = 2 and n = 0, and when M is boron or aluminum, m is any one of 1 to 3 and n is any of 0 to 2, and m + n = 3.

The 'substituted' in the 'substituted or unsubstituted' may be a substituent selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl, alkoxy, alkylamino, arylamino, heteroarylamino, alkylsilyl, An aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, and boron.

The Y may be the same or different and independently selected from the following formulas [C1] to [C39].

[Structural formula C1] [Structural formula C2] [Structural formula C3]

[Structural formula C4] [Structural formula C5] [Structural formula C6]

[Structural formula C7] [Structural formula C8] [Structural formula C9] [Structural formula C10]

[Structural formula C11] [Structural formula C12] [Structural formula C13]

[Structural formula C14] [Structural formula C15] [Structural formula C16]

[Structural formula C17] [Structural formula C18] [Structural formula C19] [Structural formula C20]

[Structural formula C21] [Structural formula C22] [Structural formula C23]

[Structural formula C24] [Structural formula C25] [Structural formula C26]

[Structural formula C27] [Structural formula C28] [Structural formula C29] [Structural formula C30]

[Structural formula C31] [Structural formula C32] [Structural formula C33]

[Structural formula C34] [Structural formula C35] [Structural formula C36]

[Structural formula C37] [Structural formula C38] [Structural formula C39]

In the above Structural Formula C1 to Structural Formula C39,

R is the same or different and is each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C6-30 aryl, A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C1-C30 alkoxy group, A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, and a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms And may be connected to an adjacent substituent by alkylene or alkenylene to form a spiro ring or a fused ring.

L represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 5 to 30 carbon atoms, L is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, an aryl group having 3 to 20 carbon atoms, A heteroaryl group, a cyano group, a halogen group, deuterium, and hydrogen, and may be connected to an adjacent substituent by an alkylene or an alkenylene to form a spiro ring or a fused ring.

Hereinafter, an organic electroluminescent device of the present invention will be described with reference to FIG.

1 is a cross-sectional view showing the structure of an organic electroluminescent device of the present invention. The organic electroluminescent device according to the present invention includes an anode 20, a hole transport layer 40, an organic emission layer 50, an electron transport layer 60 and a cathode 80, The electron injecting layer 70 may be further formed. In addition, one or two intermediate layers may be further formed, or a hole blocking layer or an electron blocking layer may be further formed.

The organic electroluminescent device of the present invention and its manufacturing method will be described with reference to FIG.

First, an anode electrode material is coated on the substrate 10 to form an anode 20. Here, as the substrate 10, an organic substrate or a transparent plastic substrate which is excellent in transparency, surface smoothness, ease of handling, and waterproofness is used as a substrate used in a conventional organic EL device. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

A hole injection layer 30 is formed on the anode 20 by vacuum thermal deposition or spin coating. Subsequently, a hole transport layer 40 is formed by vacuum thermal deposition or spin coating on the hole transport layer 30 above the hole injection layer 30.

The hole injection layer material is not particularly limited as long as it is conventionally used in the art. For example, 2-TNATA [4,4 ', 4 "-tris (2-naphthylphenyl-phenylamino) -triphenylamine] , NPD [N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'- biphenyl-4,4'-diamine], DNTPD [N, N'-diphenyl-N, N'-bis- [4- ] Can be used.

The material for the hole transport layer is not particularly limited as long as it is commonly used in the art and includes, for example, N, N'-bis (3-methylphenyl) -N, N'- -Biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalene-1-yl) -N, N'-diphenylbenzidine (? -NPD).

A hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method to form a thin film on the organic light emitting layer 50 can do. In the case where holes are injected into the cathode through the organic light-emitting layer, the lifetime and the efficiency of the device are reduced, and thus the hole blocking layer plays a role of preventing such a problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level . In this case, the hole blocking material to be used is not particularly limited, but it is required to have an ionization potential higher than that of the light emitting compound while having electron transporting ability. Typically, BAlq, BCP, TPBI and the like can be used.

After the electron transport layer 60 is deposited on the hole blocking layer by a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed, and a cathode forming metal is deposited on the electron injection layer 70 in a vacuum heat- And the cathode 80 is formed by vapor deposition to complete the organic EL device. Here, as the metal for forming the cathode, lithium, magnesium, aluminum, aluminum-lithium, calcium, magnesium-magnesium, Mg-Ag), and a transmissive cathode using ITO or IZO can be used to obtain a top light-emitting device.

In addition, the light emitting layer may be made of a host and a dopant. According to a specific example of the present invention, the thickness of the light emitting layer is preferably 50 to 2,000 ANGSTROM.

According to one embodiment of the present invention, the light emitting layer may further include a host or a dopant compound, while the compound represented by the general formula (I) is contained in the light emitting layer.

At this time, the host used in the light emitting layer may be a compound represented by the following formulas (1A) to (1D).

≪ EMI ID =

In the above formula,

Ar _{7 ,} Ar ₈ and Ar ₉ are the same or different and each independently represents a single bond, a substituted or unsubstituted aromatic linking group having 5 to 60 carbon atoms or a substituted or unsubstituted group having 2 to 60 carbon atoms Heteroaromatic linkages.

R ₂₁ to R ₃₀ are the same or different from each other and each independently represents a hydrogen atom, a heavy hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryl group, A substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, A substituted or unsubstituted (alkyl) amino group having 1 to 60 carbon atoms, a di (substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, Or an unsubstituted aryl group having 6 to 60 carbon atoms) amino group, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron And each substituent may form a condensed ring with the adjacent groups.

E, f and g are the same as or different from each other, and each independently 0 or an integer of 1 to 4.

The two sites represented by * in the anthracene may be the same as or different from each other and each independently combine with the P or Q structure to form an anthracene derivative selected from the following formulas (1Aa-1) to (1Aa-3) can do.

[Chemical Formula 1Aa-1] [Formula 1Aa-2] [Formula 1Aa-3]

The 'substituted' in the 'substituted or unsubstituted' refers to a group selected from the group consisting of deuterium, a cyano group, a halogen group, a hydroxy group, a nitro group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, An alkenyl group, an alkynyl group having 1 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 1 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, An aryloxy group having 1 to 24 carbon atoms, an arylsilyl group, and an aryloxy group having 1 to 24 carbon atoms.

≪ RTI ID = 0.0 &

In the above formula (1B)

Wherein Ar ₁₇ to Ar ₂₀ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in Formula 1A, and R ₆₀ to R ₆₃ are the same as defined in R ₂₁ to R ₃₀ in Formula 1A Lt; / RTI >

W and ww are the same as or different from each other, x and xx are the same as or different from each other, w + ww and x + xx are the same or different from each other and independently an integer of 0 to 3; Y and yy are the same or different, and z and zz are the same or different from each other, y + yy to z + zz are not more than 2, and each is an integer of 0 to 2;

[Chemical Formula 1C]

In the above formula 1C,

Wherein Ar ₂₁ to Ar ₂₄ are the same or different and are made of the same substituents as defined for Ar ₇ to Ar ₈ in the (1A) each independently from each other, wherein R ₆₄ to R ₆₇ is at R ₂₁ to R ₃₀ of Formula 1A Lt; / RTI > is as defined above.

The above ee to hh are the same as or different from each other, and each independently is an integer of 1 to 4, and the above-mentioned II to 11 are the same or different and independently an integer of 0 to 4.

[Chemical Formula 1D]

In the above formula (1D)

Wherein Ar ₂₅ to Ar ₂₇ are the same or different from each other and each independently represent a substituent group as defined in Ar ₇ to Ar ₈ in formula (1A), and R ₆₈ to R ₇₃ are the same or different from each other, The substituent groups are the same as defined in R ₂₁ to R ₃₀ of 1 A, and each substituent may form a saturated or unsaturated cyclic structure adjacent to each other. In addition, the mm to ss are the same or different from each other and each independently an integer of 0 to 4.

More specifically, the host may be represented by any one selected from the group consisting of the following [host 1] to [host 56], but is not limited thereto.

The dopant used in the light emitting layer may be a compound represented by the following formula (2) or (3).

(2) (3)

In the above formulas 2 and 3,

A is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms and is preferably an anthracene, pyrene, phenanthrene, indenophenanthrene, klysene, naphthacene, picene, triphenylene, perylene, pentacene . At this time, A may be a compound represented by the following formulas (A1) to (A10).

[Chemical Formula A1] [Chemical Formula A2] [Chemical Formula A3] Chemical Formula A4 [Chemical Formula A5]

(A9) a compound of the formula (A10)

In the above formula [A3]

Z ₁ to Z ₂ are independently selected from the group consisting of hydrogen, deuterium atom, substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, Or a substituted or unsubstituted alkylthio group having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted C6-C20 aryl group, A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, (Substituted or unsubstituted alkyl group having 1 to 60 carbon atoms), a di (substituted or unsubstituted alkyl group having 1 to 60 carbon atoms) amino group, a substituted or unsubstituted amino group having 6 to 60 carbon atoms, Burnt The number of 6 to 60 aryl), and one or more selected from the group consisting of amino group, Z ₁ to Z ₂ each are the same or different each other, may form a fused ring group and the adjacent

In the above formula (2)

X ₁ to X ₂ each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a single bond, and X ₁ to X ₂ may be bonded to each other.

Y ₁ to Y ₂ each independently represent a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 24 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 24 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 24 carbon atoms, a cyano group, a halogen group, a substituted or unsubstituted carbon number of 6 A substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, boron, deuterium, Y ₁ to Y ₂ are the same or different from each other and can form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero with groups adjacent to each other .

More specifically, in the above formula (2), X ₁ to X ₂ represent a substituted or unsubstituted phenylene group, a substituted or unsubstituted pentalenylene group, a substituted or unsubstituted indenylene group, a substituted or unsubstituted naphthylene group , A substituted or unsubstituted azulenylene group, a substituted or unsubstituted heptarenylene group, a substituted or unsubstituted indacenylene group, a substituted or unsubstituted acenaphthylene group, a substituted or unsubstituted fluorenylene group, a substituted A substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted fluoranthenylene group, a substituted or unsubstituted triphenylenylene group, a substituted or unsubstituted phenanthrenylene group, A substituted or unsubstituted naphthacenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted pyrenylene group, A substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted pyrazolylene group, a substituted or unsubstituted imidazolylene group, Substituted or unsubstituted imidazopyridinylene groups, substituted or unsubstituted imidazopyrimidinylene groups, substituted or unsubstituted pyridinylene groups, substituted or unsubstituted pyrazinylene groups, substituted or unsubstituted pyrimidinylene groups, Substituted or unsubstituted indanthrene groups, substituted or unsubstituted indanthrene groups, substituted or unsubstituted indanthrene groups, substituted or unsubstituted indanthrene groups, substituted or unsubstituted indanthrene groups, substituted or unsubstituted indanthrene groups, A substituted or unsubstituted naphthyridinylene group, a substituted or unsubstituted quinazolinylene group, a substituted or unsubstituted sienolylene group, a substituted or unsubstituted indazolylene group, a substituted or unsubstituted carbazolylene group , A substituted or unsubstituted phenanilene group, a substituted or unsubstituted phenanthridinylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted chromenylene group, a substituted or unsubstituted furanylene group, A substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, a substituted or unsubstituted benzothiophenylene group, A substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted triazylene group, or a substituted or unsubstituted oxadiazolene group Can be selected.

l and m are each an integer of 1 to 20, and n is an integer of 1 to 4.

In the above formula 3,

C _y is a substituted or unsubstituted cycloalkyl having 3 to 8 carbon atoms, b is an integer of 1 to 4, and when b is 2 or more, each cycloalkane may be in a fused form. The substituted hydrogen may be substituted with deuterium or alkyl, and may be the same or different from each other.

B Is a single bond or _{- [C (R 5) (} R 6)] p - and wherein p is not less than that of being an integer from 1 to 3, p 2 2 or more R ₅ and R ₆ are the same or different from each other.

R ₁ , R ₂ , R ₃ , R ₅ and R ₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, A substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylthio group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 5 to 60 carbon atoms, Unsubstituted (Substituted or unsubstituted alkyl having 1 to 60 carbon atoms) amino group, or a substituted or unsubstituted (having 6 to 60 carbon atoms) amino group, a di (substituted or unsubstituted) alkyl group having 1 to 60 carbon atoms 6 to 60 aryl) amino groups, substituted or unsubstituted alkylsilyl groups having 1 to 40 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 30 carbon atoms, germanium, phosphorus, and boron.

a is an integer of 1 to 4, and when a is 2 or more, R ₃ of 2 or more are the same or different, and R ₃ Each R ₃ may be in fused form, and n is an integer of 1 to 4.

More specifically, R ₁ , R ₂ and R _{3 in the} above formula (3) Are independently of each other hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted phenyl group, Pentalenyl, substituted or unsubstituted indenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted azulenyl, substituted or unsubstituted heptalenyl, substituted or unsubstituted naphthyl, Substituted or unsubstituted indanyl, substituted or unsubstituted indacenyl, substituted or unsubstituted acenaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenalenyl, substituted or unsubstituted phenyl, Transformed Substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted Substituted or unsubstituted pyrene, pyrenyl, substituted or unsubstituted chrysenyl, substituted or unsubstituted naphthacenyl, substituted or unsubstituted picenyl, substituted or unsubstituted perylene Substituted or unsubstituted pyrazolyl groups such as perylenyl, substituted or unsubstituted pentaphenyl, substituted or unsubstituted hexacenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl ), A substituted or unsubstituted imidazolyl, a substituted or unsubstituted imidazolinyl, a substituted or unsubstituted imidazopyridinyl, a substituted or unsubstituted imidazolopyrimidine Imidazopyrimidinyl, substituted or < RTI ID = 0.0 > A substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyrazinyl group, Substituted or unsubstituted quinolinyl, substituted or unsubstituted phthalazinyl, substituted or unsubstituted indolizinyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted quinolinyl, Naphthyridinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted indazolyl, substituted or unsubstituted carbazole di carbazolyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenanthridinyl, substituted or unsubstituted pyranyl, substituted or unsubstituted chromenyl group ( chromenyl), a substituted or unsubstituted furanyl group, Substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted isothiazolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted thiophenyl, A substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted isoxazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzopuranyl group, a substituted or unsubstituted dibenzopyranyl group, Or an unsubstituted triazinyl group, or a substituted or unsubstituted oxadiazolyl group.

In the present invention, B in Formula 3 may be a single bond.

The above formulas (2) and (3) may be any one selected from the group consisting of the following [substituents 1] to [52], but are not limited thereto.

[Substituent 1] [Substituent 2] [Substituent 3] [Substituent 4]

[Substituent 5] [Substituent 6] [Substituent group 7] [Substituent group 8]

[Substituent 9] [Substituent 10] [Substituent group 11] [Substituent group 12]

[Substituent 13] [Substituent 14] [Substituent 15] [Substituent group 16]

[Substituent group 17] [Substituent 18] [Substituent 19] [Substituent 20]

[Substituent 21] [Substituent 22] [Substituent 23] [Substituent 24]

[Substituent 25] [Substituent 26]

[Substituent 27] [Substituent 28] [Substituent group 29] [Substituent group 30]

[Substituent 31] [Substituent group 32] [Substituent group 33] [Substituent 34]

In the above [substituent groups 1] to [substituent group 52]

R is the same or different and is selected from the group consisting of hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, , A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms A substituted or unsubstituted alkylthio having 1 to 60 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted A substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 1 to 60 carbon atoms, (Substituted or unsubstituted C1-C60 alkyl) amino group, a di (substituted or unsubstituted C1-C60 alkyl) amino group, a substituted or unsubstituted C6-C60 arylamino group, A substituted or unsubstituted alkylsilyl group having 1 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, germanium, phosphorus, and boron, each having 1 to 12 , And each substituent may form a condensed ring with the adjacent groups.

In addition, the light emitting layer may further include various hosts and various dopant materials in addition to the host and the dopant.

At least one layer selected from the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer may be formed by a single molecular deposition method or a solution process, Means a method of forming a thin film by evaporating a material used as a material for forming each of the layers by heating or the like under a vacuum or a low pressure state and the solution process is used as a material for forming each of the layers Means a method of forming a thin film by a method such as ink jet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating and the like.

Further, the organic electroluminescent device according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel illumination device, and a single color or white flexible illumination device.

Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

Synthesis Example 1. Synthesis of Compound 1

Synthesis Example 1-1. Synthesis of <1-a>

<1-a> was synthesized by the following Reaction Scheme 1.

[Reaction Scheme 1]

 <1-a>

To a 2000 mL round bottom flask was added methyl 5-bromo-2-iodobenzoate (65.2 g, 191 mmol), 1-naphthaleneboronic acid (29.9 g, 174 mmol), tetrakistriphenylphosphine palladium , Potassium carbonate (48.1 g, 348 mmol), tetrahydrofuran (326 mL), toluene (326 mL) and water (130 mL) were placed and refluxed. After completion of the reaction, the organic layer obtained by extracting with water and ethyl acetate was treated with anhydrous magnesium sulfate, concentrated under reduced pressure, and separated by column chromatography using hexane and dichloromethane as developing solvent to obtain 29.7 g , 52.7%).

Synthesis Example 1-2. Synthesis of <1-b>

<1-b> was synthesized by the following Reaction Scheme 2.

[Reaction Scheme 2]

  <1-a> <1-b>

<1-a> (29.6 g, 87 mmol), sodium hydroxide (4.16 g, 104 mmol) and ethanol (296 mL) were placed in a 1000 mL round bottom flask and refluxed. After the reaction was completed, the reaction mixture was cooled to room temperature, acidified with 2 N hydrochloric acid, and then filtered. The filtered crystals were washed with water three times and dried to give <1-b> (25.5 g, 90.0%).

Synthesis Example 1-3. Synthesis of <1-c>

<1-c> was synthesized by the following Reaction Scheme 3.

[Reaction Scheme 3]

 <1-b> <1-c>

<1-b> (25.5 g, 78 mmol) and methanesulfonic acid (255 mL) obtained from the reaction scheme 2 are introduced into a 500 mL round bottom flask and stirred at a reaction temperature of 40 ° C. for 72 hours. When the reaction was completed, the reaction mixture was slowly added to ice water, and the layers were separated using dichloromethane and water. The obtained organic layer was concentrated under reduced pressure and then purified by column chromatography to obtain <1-c> (14.3 g, 59.2%).

Synthesis Example 1-4. Synthesis of <1-d>

<1-d> was synthesized by the following Reaction Scheme 4.

[Reaction Scheme 4]

 <1-c> <1-d>

(14.2 g, 46 mmol), phenylboronic acid (6.7 g, 55 mmol), tetrakis triphenylphosphine palladium (1.1 g, 1 mmol), potassium carbonate (12.7 g, 92 mmol), tetrahydrofuran (34 mL), toluene (34 mL) and water (14 mL) were added and refluxed. After completion of the reaction, the organic layer obtained by extraction with water and ethyl acetate was treated with anhydrous magnesium sulfate, concentrated under reduced pressure, and separated by column chromatography using hexane and dichloromethane as eluent to obtain <1-d> (10.6 g , 75.0%).

Synthesis Example 1-5. Synthesis of <1-e>

<1-e> was synthesized by the following Reaction Scheme 5.

[Reaction Scheme 5]

<1-d> <1-e>

<1-d> (10.6 g, 34 mmol) and chloroform (106 mL) were added to a 500 mL round bottom flask at room temperature and stirred. Bromine (16.5 g, 103 mmol) is diluted in chloroform (21 mL) and slowly added dropwise. Purity is measured by high performance liquid chromatography to confirm the progress of the reaction. After completion of the reaction, a saturated sodium thiosulfate saturated solution is added dropwise. The resulting crystals are filtered, washed several times with water and dried. The dried product was recrystallized using monochlorobenzene and heptane to obtain <1-e> (11.4 g, 86.0%).

Synthesis Example 1-6. Synthesis of <1-f>

<1-f> was synthesized by the following reaction scheme [6].

[Reaction Scheme 6]

<1-e> <1-f>

1-e> (11.4 g, 30 mmol) and 2-naphthaleneboronic acid (6.1 g, 36 mmol) instead of phenylboronic acid were used in the same manner as in [Reaction Scheme 4] To obtain <1-f> (9.6 g, 75.0%).

Synthesis Example 1-7. Synthesis of <1-g>

<1-g> was synthesized by the following Reaction Scheme 7.

[Reaction Scheme 7]

<1-g>

3-Bromopyridine (27.0 g, 171 mmol), 30% hydrogen peroxide (810 mL) and acetic acid (1350 mL) are placed in a 3000 mL round bottom flask and refluxed. After 3 hours of reaction, 30% hydrogen peroxide (25 mL) is added. After 19 hours of reaction, 30% hydrogen peroxide (25 mL) was added and refluxed for 4 hours. After completion of the reaction, the reaction mixture is concentrated under reduced pressure. After adding water, the reaction mixture is concentrated under reduced pressure. After dissolving in dichloromethane, sodium carbonate aqueous solution is added and extracted. The obtained organic layer was concentrated under reduced pressure to obtain <1-g> (22.9 g, 77%).

Synthesis Example 1-8. Synthesis of <1-h>

<1-h> was synthesized by the following Reaction Scheme 8.

[Reaction Scheme 8]

<1-g> <1-h>

After cooling the reaction temperature to 0 ° C, add <1-g> (22.9 g, 132 mmol) and sulfuric acid (55 mL) to a 2000 mL round bottom flask and stir. Slowly add dropwise sulfuric acid (55 mL) and nitric acid (92 mL). The reaction is heated at 90 DEG C for 2 hours. After completion of the reaction, cool to room temperature and add to ice water (720 mL). 50% sodium hydroxide aqueous solution is weakly basified to pH 8 by slow dropwise addition. The product was filtered and dried to give <1-h> (20.7 g, 72.0%).

Synthesis Example 1-9. Synthesis of <1-i>

<1-i> was synthesized by the following Reaction Scheme 9.

[Reaction Scheme 9]

<1-h> <1-i>

1-h> (20.8 g, 95 mmol), phenol (12.5 g, 133 mmol), potassium tert-butoxide (10.6 g, 95 mmol) and tert-butanol (312 mL) were placed in a 500 mL round bottom flask Reflux for 16 hours. After cooling to room temperature, the reaction mixture is poured into ice and stirred. After making basic with 10% aqueous sodium hydroxide solution, chloroform is added and extracted. The obtained organic layer was treated with anhydrous sodium sulfate, concentrated under reduced pressure, and <1-i> (13.4 g, 61.0%) was obtained by separating by column chromatography using dichloromethane and methanol as developing solvents.

Synthesis Example 1-10. Synthesis of <1-j>

<1-j> was synthesized by the following Reaction Scheme 10.

[Reaction Scheme 10]

<1-i> <1-j>

Add <1-i> (13.4 g, 58 mmol) and acetic acid (268 mL) to a 500 mL round bottom flask and heat to a reaction temperature of 60 ° C. Add iron powder (21.0 g, 375 mmol) and stir for 30 minutes. After completion of the reaction, the reaction product is filtered, and the filtrate is washed with acetic acid. The filtrate was concentrated under reduced pressure, and then an aqueous solution of sodium hydroxide was added to make it basic at pH 10. The organic layer obtained after extracting with chloroform was treated with anhydrous sodium sulfate and concentrated under reduced pressure to obtain <1-j> (9.8 g, 91.0%).

Synthesis Example 1-11. Synthesis of <1-k>

<1-k> was synthesized by the following Reaction Scheme 11.

[Reaction Scheme 11]

<1-j> <1-k>

<1-j> (9.7 g, 52 mmol), 36% hydrochloric acid (20.0 mL) and water (20 mL) are added to a 250 mL round bottom flask under nitrogen and the reaction temperature is cooled to 0 ° C. Sodium nitrite (5.4 g, 78 mmol) is dissolved in water (20 mL) and added dropwise. After completion of the dropwise addition, the mixture was stirred for 1 hour, and then potassium iodide (17.3 g, 104 mmol) was dissolved in water (35 mL) and added dropwise. After completion of dropwise addition, the mixture is stirred at room temperature for 1 hour. The reaction temperature is raised to 60 占 폚 and stirred for 12 hours. After completion of the reaction, the reaction mixture is cooled to room temperature, and dichloromethane is added to extract it. The organic layer obtained is charged with a saturated sodium thiosulfate saturated solution, water is added to the obtained organic layer after extraction, and further extraction is carried out. The obtained organic layer was concentrated under reduced pressure, and <1-k> (9.9 g, 63.8%) was obtained by column chromatography using dichloromethane and heptane as eluent.

Synthesis Example 1-12. Synthesis of <1-l>

<1-l> was synthesized by the following reaction scheme [12].

[Reaction Scheme 12]

<1-k> <1-f> <1-l>

<1-k> (9.89 g, 33 mmol) and tetrahydrofuran (100 mL) are added to a nitrogen-purged 250 mL round bottom flask at room temperature. After cooling to -78 ° C, normal butyl lithium (19.4 ml, 31 mmol, 1.6 M) is slowly added dropwise. After completion of dropwise addition, <2-f> (9.6 g, 22 mmol) was added to the mixture and the mixture was heated to room temperature. After stirring for 12 hours at room temperature, water (100 mL) is added and the reaction is terminated. After adding dichloromethane, the obtained organic layer was concentrated under reduced pressure to obtain <1-l> (8.0 g, 60.0%).

Synthesis Example 1-13. Synthesis of Compound 1

<Compound 1> was synthesized by the following Reaction Scheme (13).

[Reaction Scheme 13]

  <1-l> <Compound 1>

<1-l> (8 g, 13 mmol), acetic acid (80 mL) and sulfuric acid (2 mL) are placed in a 250 mL round bottom flask and refluxed. When the reaction is completed, the reaction temperature is cooled to room temperature and the resulting solid is filtered. Washed three times with water and methanol, and then recrystallized with toluene and methanol to obtain Compound 1 (4.7 g, 80.0%).

MS [M] ^&lt; ⁺ & gt ^; : 585.21

Elemental analysis: Theoretical value C, 90.23; H, 4.65; N, 2.39; O, 2.73 actual value C, 90.23; H, 4.65; N, 2.39; , 2.73

Synthesis Example 2. Synthesis of Chemical 6

Synthesis Example 2-1. Synthesis of <2-a>

<2-a> was synthesized by the following reaction scheme [14].

[Reaction Scheme 14]

<2-a>

Methyl-4-bromo-1-iodo-2-naphthoate (74.8 g, 191 mmol) was reacted with methyl 5-bromo-2-iodobenzoate in the same manner as in [Reaction Scheme 1] &Lt; 2-a > (34.0 g, 52.7%).

Synthesis Example 2-2. Synthesis of <2-b>

<2-b> was synthesized by the following Reaction Scheme 15.

[Reaction Scheme 15]

&Lt; 2-a > < 2-b &

<2-b> (25.9 g, 90.0%) was obtained by reacting <2-a> in place of <1-a> by the same synthetic method as in [scheme 2].

Synthesis Example 2-3. Synthesis of <2-c>

<2-c> was synthesized by the following reaction scheme [16].

[Reaction Scheme 16]

<2-b> <2-c>

<2-c> (14.4 g, 59.2%) was obtained by reacting <2-b> instead of <1-b> by the same synthetic method as in [Reaction Scheme 3].

Synthesis Example 2-4. Synthesis of <2-d>

<2-d> was synthesized by the following Reaction Scheme (17).

[Reaction Scheme 17]

<2-c> <2-d>

<2-c> was reacted instead of <1-d> to obtain <2-d> (11.1 g, 86.0%) according to the same synthetic method as in [Reaction Scheme 5].

Synthesis Example 2-5. Synthesis of <2-e>

<2-e> was synthesized by the following Reaction Scheme 18.

[Reaction Scheme 18]

&Lt; 2-d > < 2-e &

2-d> (12.0 g, 27 mmol) was reacted with 2-naphthaleneboronic acid (10.8 g, 63 mmol) instead of <1-e>> (10.9 g, 75.0%) was obtained

Synthesis Example 2-6. Synthesis of <2-f>

&Lt; 2-f > was synthesized according to the following Reaction Scheme (19).

[Reaction Scheme 19]

<2-f>

Sodium hydride (5.45 g, 136 mmol, 60%) and tetrahydrofuran (66 mL) are added to a 250 mL round bottom flask and stirred. Phenol (12.8 g, 136 mmol) is added dropwise. A mixture of 4-chloro-3-nitropyridine (10.8 g, 68 mmol) and tetrahydrofuran (44 mL) was added dropwise and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture is cooled to room temperature, water is added, and the reaction is terminated. The organic layer was extracted with dichloromethane, and the resulting organic layer was concentrated under reduced pressure, and <2-f> (13.3 g, 90.0%) was obtained by column chromatography using ethyl acetate and heptane as eluent.

Synthesis Example 2-7. Synthesis of <2-g>

&Lt; 2-g > was synthesized by the following Reaction Scheme (20).

[Reaction Scheme 20]

<2-f> <2-g>

<2-f> (13.2 g, 61 mmol), iron (10.4 g, 186 mmol) and ethanol (13.2 mL, 50%) were placed in a 100 mL round bottom flask and refluxed. Add ethanol (4.1 mL, 50%) with hydrochloric acid (0.7 mL, 37%) and add dropwise. After completion of the dropwise addition, reflux is carried out for 3 hours. After completion of the reaction, an aqueous sodium hydroxide solution is added and the mixture is basified. After cooling to room temperature, filtrate with celite. The filtrate was concentrated under reduced pressure and <2-g> (8.4 g, 74.0%) was obtained by column chromatography using ethyl acetate and heptane as eluent.

Synthesis Example 2-8. Synthesis of Compound 6

<2-h> was synthesized by the following Reaction Scheme (21).

[Reaction Scheme 21]

<2-g> <2-h>

<2-h> (8.6 g, 63.8%) was obtained by reacting <2-g> (8.4 g, 45 mmol) in place of <1-j> by the same synthetic method as that of [Reaction Scheme 11].

Synthesis Example 2-9. Synthesis of <2-i>

<2-i> was synthesized by the following reaction scheme [22].

[Reaction Scheme 22]

<2-h> <2-e> <2-i>

<2-i> (8.1 g, 60.0%) was obtained in the same manner as in [scheme 12].

Synthesis Example 2-10. Synthesis of Compound 6

<Compound 6> was synthesized according to the following Reaction Scheme 23.

[Reaction Scheme 23]

    <2-i> <Compound 6>

<Compound 6> (4.7 g, 60.0%) was obtained in the same manner as in [Scheme 13].

MS [M] ^&lt; ⁺ & gt ^; : 685.24

Elemental analysis: Theoretical value C, 91.07; H, 4.56; N, 2.04; O, 2.33 actual value C, 91.07; H, 4.56; N, 2.04; , 2.33

Synthesis Example 3. Synthesis of Compound 23

Synthesis Example 3-1. Synthesis of <3-a>

<3-a> was synthesized by the following reaction scheme [24].

[Reaction Scheme 24]

<3-a>

3-a> (28.8 g, 61.0%) was obtained by reacting 9-phenanthreneboronic acid (26.8 g, 121 mmol) instead of 1-naphthylboronic acid in the same manner as in [Reaction Scheme 1].

Synthesis Example 3-2. Synthesis of <3-b>

<3-b> was synthesized by the following Reaction Scheme 25.

[Reaction Scheme 25]

&Lt; 3-a > < 3-b &

<3-b> (22.2 g, 80.0%) was obtained by reacting <3-a> instead of <1-b> by the same synthetic method as in [scheme 2].

Synthesis Example 3-3. Synthesis of <3-c>

<3-c> was synthesized by the following reaction scheme.

[Reaction Scheme 26]

<3-b> <3-c>

<3-c> (13.2 g, 63.0%) was obtained by reacting <3-b> instead of <1-b> by the same synthetic method as in [scheme 3].

Synthesis Example 3-4. Synthesis of <3-d>

<3-d> was synthesized by the following reaction scheme [27].

[Reaction Scheme 27]

<3-c> <3-d>

<3-c> was reacted with <3-c> instead of <1-c> by the same synthetic method as in [Reaction Scheme 4] to obtain <3-d> (11.1 g, 70.0%).

Synthesis Example 3-5. Synthesis of <3-e>

<3-e> was synthesized by the following Reaction Scheme 28.

[Reaction Scheme 28]

<3-d> <3-e>

3-d> (11.0 g, 25 mmol) and 1-naphthaleneboronic acid (9.9 g, 58 mmol) instead of 2-naphthaleneboronic acid were used in the same manner as in [Reaction Scheme 18] ) Was reacted to obtain <3-e> (10.0 g, 75.0%).

Synthesis Example 3-6. Synthesis of <3-f>

<3-f> was synthesized by the following Reaction Scheme 29.

[Reaction Scheme 29]

<1-h> <3-f>

(19.5 g, 89 mmol), diphenylamine (16.6 g, 98 mmol), palladium (II) acetate (0.8 g, 3.6 mmol), sodium tert-butoxide (34.2 g, 356 mmol) was added and the reaction temperature was raised to 50 캜. Tri-tert-butylphosphine (0.7 g, 3.6 mmol) was added and refluxed. After completion of the reaction, the reaction mixture is cooled to room temperature and extracted with water and ethyl acetate. The obtained organic layer was treated with anhydrous sodium sulfate, concentrated under reduced pressure, and then <3-f> (16.4 g, 60.0%) was obtained by column chromatography using ethyl acetate and heptane as eluent.

Synthesis Example 3-7. Synthesis of <3-g>

<3-g> was synthesized by the following Reaction Scheme 30.

[Reaction Scheme 30]

<3-f> <3-g>

<3-g> (12.4 g, 91.0%) was obtained by reacting <3-f> (16.0 g, 52 mmol) in place of <1-i> by the same synthetic method as that of [scheme 10].

Synthesis Example 3-8. Synthesis of <3-h>

<3-h> was synthesized by the following reaction scheme [31].

[Reaction Scheme 31]

<3-g> <3-h>

3-h> (10.9 g, 63.8%) was obtained by reacting <3-g> (12.0 g, 46 mmol) in place of <1-j> by the same synthetic method as that of [Reaction Scheme 11].

Synthesis Example 3-9. Synthesis of <3-i>

<3-i> was synthesized by the following Reaction Formula 32.

[Reaction Scheme 32]

<3-h><3-e><3-i>

3-i> (8.8 g, 60.0%) was obtained by reacting <3-h> instead of <1-k> and <3-e> .

Synthesis Example 3-10. Synthesis of Compound 23

<Compound 23> was synthesized by the following Reaction Scheme 33.

[Reaction Scheme 33]

<3-i> <Compound 23>

<Compound 23> (4.7 g, 60.0%) was obtained by reacting <3-i> instead of <1-l> by the same synthetic method as that of [Reaction Scheme 13].

MS [M] ^&lt; ⁺ & gt ^; : 760.29

Elemental analysis: Theoretical value C, 91.55; H, 4.77; N, 3.68 Actual value C, 91.55; H, 4.77; N, 3.68

Synthesis Example 4. Synthesis of Compound 25

Synthesis Example 4-1. Synthesis of <4-a>

<4-a> was synthesized according to the following Reaction Scheme 34.

[Reaction Scheme 34]

<1-h> <4-a>

2-Naphthol (15.6 g, 108 mmol) was reacted with phenol in the same manner as in [Reaction Scheme 9] to obtain <4-a> (13.3 g, 61.0%).

Synthesis Example 4-2. Synthesis of <4-b>

<4-b> was synthesized by the following Reaction Scheme 35.

[Reaction Scheme 35]

&Lt; 4-a > < 4-b &

<4-b> (10.1 g, 91.0%) was obtained by reacting <4-a> instead of <1-i> by the same synthetic method as in [Reaction formula 10].

Synthesis Example 4-3. Synthesis of <4-c>

<4-c> was synthesized according to the following Reaction Scheme 36.

[Reaction Scheme 36]

<4-b> <4-c>

<4-c> (9.4 g, 63.8%) was obtained by reacting <4-b> instead of <1-j> by the same synthetic method as in [Reaction Scheme 11].

Synthesis Example 4-4. Synthesis of <4-d>

<4-d> was synthesized by the following Reaction Scheme 37.

[Reaction Scheme 37]

<4-c> <3-e> <4-d>

4-d> (8.1 g, 60.0%) was obtained by reacting <3-e> instead of <4-c> and <1-f> in place of <1-k> .

Synthesis Example 4-5. Synthesis of Compound 25

&Lt; Compound 25 > was synthesized by the following reaction scheme.

[Reaction Scheme 38]

   <4-d> <Compound 25>

<25> (4.7 g, 80.0%) was obtained by reacting <4-d> instead of <1-l> by the same synthetic method as in [Reaction Scheme 13].

MS [M] ^&lt; ⁺ & gt ^; : 735.26

Elemental analysis: Theoretical value C, 91.40; H, 4.52; N, 1.90; O, 2.17 actual value C, 91.40; H, 4.52; N, 1.90; O, 2.17

Synthesis Example 5. Synthesis of Compound 28

Synthesis Example 5-1. Synthesis of <5-a>

&Lt; 5-a > &gt; was synthesized by the following reaction scheme [39].

[Reaction Scheme 39]

<1-c> <5-a>

<5-a> (12.2 g, 86.0%) was obtained by reacting <1-c> instead of <1-d> by the same synthetic method as in [Reaction Scheme 5].

Synthesis Example 5-2. Synthesis of <5-b>

<5-b> was synthesized by the following Reaction Scheme 40.

[Reaction Scheme 40]

<1-h> <5-b>

5-b> (19.5 g, 61.0%) was obtained by reacting 3-hydroxypyridine (18.2 g, 192 mmol) instead of phenol by the same synthetic method as in Reaction Scheme 9.

Synthesis Example 5-3. Synthesis of <5-c>

&Lt; 5-c > was synthesized by the following reaction scheme [41].

[Reaction Scheme 41]

<5-b> <5-c>

<5-c> (14.2 g, 91.0%) was obtained by reacting <5-b> instead of <1-i> by the same synthetic method as that of [scheme 10].

Synthesis Example 5-4. Synthesis of <5-d>

<5-d> was synthesized by the following reaction scheme [42].

[Reaction Scheme 42]

<5-c> <5-d>

5-d> (14.2 g, 63.8%) was obtained by reacting <5-c> instead of <1-j> by the same synthetic method as in [Reaction Scheme 11].

Synthesis Example 5-5. Synthesis of <5-e>

<5-e> was synthesized by the following reaction scheme [43].

[Reaction Scheme 43]

<5-d> <5-a> <5-e>

5-e> (10.6 g, 60.0%) was prepared by reacting <5-a> instead of <5-d> and <1-f> with the same synthetic method as in [Reaction Scheme 12] .

Synthesis Example 5-6. Synthesis of <5-f>

<5-f> was synthesized according to the following scheme (Scheme 44).

[Reaction Scheme 44]

<5-e> <5-f>

<5-f> (6.1 g, 80.0%) was obtained by reacting <5-e> instead of <1-l> by the same synthetic method as in [Reaction Scheme 13].

Synthesis Example 5-7. Synthesis of <5-g>

&Lt; 5-g > was synthesized according to the following reaction scheme [45].

[Reaction Scheme 45]

<5-g>

To a 100 mL round bottom flask was added aniline (4.2 g, 45 mmol), 4-bromobiphenyl (10.5 g, 45 mmol), tris (dibenzylideneacetone) dipalladium (0) (1.1 g, 1.8 mmol) and sodium tert-butoxide (8.7 g, 90 mmol) were added to the solution, and the mixture was refluxed. After completion of the reaction, the reaction mixture is cooled to room temperature and extracted with water and ethyl acetate. The resulting organic layer was treated with anhydrous sodium sulfate, concentrated under reduced pressure, and then <5-g> (6.6 g, 60.0%) was obtained by column chromatography using dichloromethane and heptane as developing solvents.

Synthesis Example 5-8. Synthesis of Compound 28

<Compound 28> was synthesized by the following Reaction Scheme 46.

[Reaction Scheme 46]

&Lt; 5-f > < 5-g &

(6.0 g, 11 mmol), <5-g> (6.5 g, 27 mmol), palladium (II) acetate (0.1 g, 0.4 mmol), sodium tert-butoxide (4.3 g, 44 mmol) and heated to a reaction temperature of 50 占 폚. Tri-tert-butylphosphine (0.3 g, 0.4 mmol) was added and refluxed. After completion of the reaction, the reaction mixture is cooled to room temperature and extracted with water and ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then subjected to column chromatography using ethyl acetate and heptane as eluent to obtain Compound 28 (5.8 g, 60.0%).

MS [M] ^&lt; ⁺ & gt ^; : 870.34

Elemental analysis: Theoretical value C, 86.87; H, 4.86; N, 6.43; O, 1.84 actual value C, 86.87; H, 4.86; N, 6.43; O, 1.84

Synthesis Example 6. Synthesis of Compound 36

Synthesis Example 6-1. Synthesis of <6-a>

&Lt; 6-a > was synthesized by the following reaction scheme [47].

[Reaction Scheme 47]

<1-k> <5-a> <6-a>

<6-a> (7.0 g, 60.0%) was obtained by reacting <5-a> instead of <1-f> by the same synthetic method as in [Reaction Scheme 12].

Synthesis Example 6-2. Synthesis of <6-b>

<6-b> was synthesized by the following Reaction Scheme 48.

[Reaction Scheme 48]

<6-a> <6-b>

6-b> (4.1 g, 80.0%) was obtained by reacting <6-a> instead of <1-l> by the same synthetic method as in [Reaction Scheme 13].

Synthesis Example 6-3. Synthesis of <6-c>

&Lt; 6-c > was synthesized by the following reaction scheme [49].

[Reaction Scheme 49]

<6-c>

Amino-2-methylpyridine (3.8 g, 35 mmol) was used instead of aniline and l-bromo-4- (trimethylsilyl) benzene , 35 mmol) was reacted to obtain <6-c> (4.5 g, 50.0%).

Synthesis Example 6-4. Synthesis of Compound 36

&Lt; Compound 36 > was synthesized by the following reaction scheme [Reaction formula 50].

[Reaction Scheme 50]

<6-b> <6-c> <Compound 36>

6-c> (4.6 g, 18 mmol) was used instead of <6-b> (4.0 g, 7 mmol) and <5-g> instead of <5-f> <Compound 36> (3.6 g, 55.0%) was obtained.

MS [M] ^&lt; ⁺ & gt ^; : 891.38

Elemental analysis: Theoretical value C, 78.08; H, 5.99; N, 7.85; O, 1.79; Si, 6.30 Actual value C, 78.08; H, 5.99; N, 7.85; O, 1.79; Si, 6.30

Synthesis Example 7. Synthesis of Compound 41

Synthesis Example 7-1. Synthesis of <7-a>

<7-a> was synthesized by the following Reaction Scheme (51).

[Reaction Scheme 51]

<7-a>

7-a> (23.6 g, 52.7%) was obtained by reacting 4-crescibenonic acid (29.1 g, 107 mmol) instead of 1-naphthalenevoronic acid in the same manner as in [Reaction Scheme 1].

Synthesis Example 7-2. Synthesis of <7-b>

<7-b> was synthesized by the following Reaction Scheme 52.

[Reaction Scheme 52]

<7-a> <7-b>

7-b> (20.6 g, 90.0%) was obtained by reacting <7-a> instead of <1-a> by the same synthetic method as in [Reaction Scheme 2].

Synthesis Example 7-3. Synthesis of <7-c>

<7-c> was synthesized by the following Reaction Scheme 53.

[Reaction Scheme 53]

<7-b> <7-c>

<7-c> (11.0 g, 56.0%) was obtained by reacting <7-b> instead of <1-b> by the same synthetic method as in [Reaction Scheme 3].

Synthesis Example 7-4. Synthesis of <7-d>

<7-d> was synthesized by the following reaction scheme.

[Reaction Scheme 54]

<7-c> <7-d>

<7-c> was reacted with <7-c> instead of <1-d> by the same synthetic method as in [Reaction Scheme 5] to obtain <7-d> (11.3 g, 86.0%).

Synthesis Example 7-5. Synthesis of <7-e>

<7-e> was synthesized by the following Reaction Scheme 55.

[Reaction Scheme 55]

<5-d> <7-d> <7-e>

7-e> (9.1 g, 60.0%) was obtained by reacting <7-d> instead of <5-d> and <1-f> in place of <1-k> .

Synthesis Example 7-6. Synthesis of <7-f>

<7-f> was synthesized by the following reaction scheme.

[Reaction Scheme 56]

<7-e> <7-f>

<7-f> (5.3 g, 80.0%) was obtained by reacting <7-e> instead of <1-l> by the same synthetic method as in [Reaction Scheme 13].

Synthesis Example 7-7. Synthesis of <7-g>

<7-g> was synthesized by the following Reaction Scheme (57).

[Reaction Scheme 57]

    <7-g>

7-g> (4.5 g, 50.0%) was obtained by reacting 1-bromonaphthalene <8.5 g, 41 mmol> instead of 4-bromobiphenyl by the same synthetic method as in [Reaction Formula 45].

Synthesis Example 7-8. Synthesis of Compound 41

<Compound 41> was synthesized by the following Reaction Scheme 58.

[Reaction Scheme 58]

&Lt; 7-f > < 7-g &

7-g> (4.1 g, 19 mmol) was used instead of <7-f> (5.0 g, 8 mmol) and <5-g> in place of <5-f> (Compound 41) (3.9 g, 55.0%).

MS [M] ^&lt; ⁺ & gt ^; : 918.34

Elemental analysis: Theoretical value C, 87.56; H, 4.61; N, 6.10; O, 1.74 actual value C, 87.56; H, 4.61; N, 6.10; O, 1.74

Examples 1 to 4: Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber and the base pressure was adjusted to 1 × 10 ^-6 torr, the organic material was injected onto the ITO using DNTPD (700 Å), α-NPD (300 Å) BD1 (3 wt%) was co-evaporated (300 Å) as the dopant of the compounds of Examples 1 to 4 and then Alq ₃ (350 Å), LiF (5 Å) and Al (1000 Å) , And 0.4 mA.

[DNTPD] [[alpha] -NPD]

[BD1] [Alq _3]

Comparative Examples 1 to 2

The organic light emitting devices for Comparative Examples 1 and 2 were fabricated in the same manner except that the following compounds [101] and [102] were used in place of the compound prepared by the invention in the device structures of Examples 1 to 4, The structure is as follows.

[Compound 101] [Compound 102]

Examples 5 to 7: Preparation of organic light emitting diode

The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the substrate was allowed to have a pressure of 1 × 10 ^-6 torr, and then DNTPD (700 Å), α-NPD (300 Å) (3 wt%) prepared in Preparation Examples 5 to 7 were co-evaporated (300 Å) and then Alq ₃ (350 Å), LiF (5 Å) and Al (1000 Å) , And 0.4 mA.

[Compound 101]

Comparative Examples 3 to 4

The organic light emitting devices for Comparative Examples 3 to 4 were fabricated in the same manner except that the following [Compound 103] and [Compound 104] were used in place of the compound prepared by the invention in the device structures of Examples 5 to 7, The structure is as follows.

[Compound 103] [Compound 104]

The voltage, luminance, color coordinates, and lifetime of the organic light emitting device manufactured according to Examples 1 to 7 and Comparative Examples 1 to 4 were measured, and the results are shown in Table 1 below. T ₈₀ means the time required for the luminance to decrease from the initial luminance (5000 nits) to 80%.

division Host Dopant Voltage (V) Brightness (Cd / m2) CIEx CIEy T ₈₀ Example 1 Compound 1 BD1 3.8 713 0.136 0.097 59 Example 2 Compound 6 BD1 3.8 735 0.137 0.099 63 Example 3 Compound 23 BD1 3.8 710 0.137 0.098 60 Example 4 Compound 25 BD1 3.8 698 0.138 0.098 59 Comparative Example 1 Compound 101 BD1 4.1 562 0.138 0.097 42 Comparative Example 2 Compound 102 BD1 4.2 612 0.138 0.098 51 Example 5 Compound 101 Compound 28 3.9 729 0.136 0.110 85 Example 6 Compound 101 Compound 36 3.8 711 0.137 0.105 92 Example 7 Compound 101 Compound 41 3.7 723 0.135 0.101 101 Comparative Example 3 Compound 101 Compound 103 4.2 515 0.149 0.166 46 Comparative Example 4 Compound 101 Compound 104 4.1 550 0.145 0.185 57

As shown in Table 1, the organic electroluminescent compound according to the present invention has lower driving voltage and longer lifetime than the anthracene host compound of the prior art. (Examples 1 to 4) It is also found that the color purity of blue is improved and the lifetime is improved as compared with the case of using the pyrene-based arylamine compound. (Examples 5 to 7) Accordingly, there is a high possibility of application as an organic light emitting element for realizing a full color.

Claims (15)

An organic luminescent compound represented by the following formula (I):
(I)

In the above formula (I)
X is NR _11, O, S, or SiR ₁₂ R _13,
A ₁ and A ₂ are the same or different and are each independently an aromatic ring or a heteroaromatic ring and at least one of A ₁ and A ₂ is a heteroaromatic ring containing at least one N,
Z ₁ and Z ₂ are the same or different from each other and each independently represents a monovalent or polycyclic aromatic ring, a monocyclic or polycyclic heteroaromatic ring, a 5- to 6-membered heteroaromatic ring fused with an aromatic ring, A 6-membered heteroaromatic ring is fused to a single-ring or multi-ring aromatic ring,
R ₁ to R ₁₃ are the same or different from each other and each independently represents hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted carbon number A substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C2-C20 alkynyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted hetero atom, O, N, S and P A substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, a substituted or unsubstituted C1-C30 alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C1-C30 arylthio group, a substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted C5-C30 arylamine group , A substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 5 to 30 carbon atoms, a cyano group, a nitro group, a hydroxyl group and a halogen group,
R ₁ to R ₁₃ may combine with each other or adjacent substituents to form a saturated or unsaturated ring. The method according to claim 1,
Wherein R ₁ to R ₁₃ are further substituted by one or more substituents and at least one of the substituents is selected from the group consisting of deuterium, cyano, halogen, hydroxy, nitro, alkyl having 1 to 24 carbon atoms, halogenated alkyl having 1 to 24 carbon , An alkenyl group having 1 to 24 carbon atoms, an alkynyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an arylalkyl group having 6 to 24 carbon atoms, a heteroaryl group having 2 to 24 carbon atoms, An alkoxy group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms, an arylamino group having 3 to 24 carbon atoms, a heteroarylamino group having 1 to 24 carbon atoms, an alkylsilyl group having 1 to 24 carbon atoms, an arylsilyl group having 3 to 24 carbon atoms And an aryloxy group having 3 to 24 carbon atoms. The method according to claim 1,
remind

And

Are each the same or different and independently selected from the following C1 to C15:

C1 C2 C3 C4

C5 C6 C7 C8

C9 C10 C11 C12

C13 C14 C15
In the above C1 to C15,
Wherein A ₁ to A ₁₀ are the same as or different from each other and each independently N or CR, R and R 'are the same as defined for R ₁ to R ₁₃ in the above formula (1) . The method according to claim 1,
R ₁ to R ₁₀ are the same or different from each other and each independently represents hydrogen, deuterium, a halogen group, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, Substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 5 -C 30 aryl, substituted or unsubstituted C 2 -C 20 cycloalkyl, A substituted heteroaryl group having 2 to 30 carbon atoms, and an organic luminescent compound represented by the following formula:
[Structural formula Q]

In the above formula [Q]
* Means a site bound to R ₁ to R ₁₀ of the above formula (I)
L is a substituted or unsubstituted alkylene group having 1 to 60 carbon atoms, a substituted or unsubstituted alkylene group having 2 to 60 carbon atoms Substituted or unsubstituted C2-C60 alkynylene groups, substituted or unsubstituted C3-C60 alkynylene groups, substituted or unsubstituted C2- A substituted or unsubstituted C2 to C30 heteroarylene group, a substituted or unsubstituted C3 to C30 cycloalkyl, a substituted or unsubstituted C1 to C50 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, A substituted or unsubstituted C2-C60 heteroarylene group in which at least one unsubstituted C 6 -C 60 arylene group and a substituted or unsubstituted C 3 -C 30 cycloalkyl are fused together and n is 0 to 2 And when n is 2, a plurality of L's are the same or different from each other,
Ar ₁ to Ar ₂ are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms An aryl group and a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms having a hetero atom O, N, S or P,
Ar ₁ to Ar ₂ may be linked to each other or adjacent substituents to form a condensed ring of aliphatic, aromatic, aliphatic hetero or aromatic hetero. 5. The method of claim 4,
Wherein R ₉ and R ₁₀ are each a substituent represented by the above formula [Q], and R ₉ and R ₁₀ are the same or different from each other. 5. The method of claim 4,
Wherein Ar ₁ and Ar ₂ are each independently any one selected from the following [substituent (s) B1] to [substituent B46]:
[Substituent B1] [Substituent B2] [Substituent B3]

[Substituent B4] [Substituent B5] [Substituent B6]

[Substituent B7] [Substituent B8] [Substituent B9]

[Substituent B10] [Substituent B11] [Substituent B12]

[Substituent B13] [Substituent B14] [Substituent B15]

[Substituent B16] [Substituent B17] [Substituent B18]

[Substituent B19] [Substituent B20] [Substituent B21]

[Substituent B22] [Substituent B23] [Substituent B24]

[Substituent B25] [Substituent B26] [Substituent B27]

[Substituent B28] [Substituent B29] [Substituent B30]

[Substituent B31] [Substituent B32] [Substituent B33]

[Substituent B34] [Substituent B35] [Substituent B36]

[Substituent B37] [Substituent B38] [Substituent B39]

[Substituent B40] [Substituent B41] [Substituent B42]

[Substituent B43] [Substituent B44] [Substituent B45]

[Substituent B46]

In the above [substituents B1] to [substituent B46]
R represents a hydrogen atom, a heavy hydrogen atom, a cyano group, a halogen group, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 18 carbon atoms, an arylalkyl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, A silyl group, an arylsilyl group having 6 to 18 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms, and n is an integer of 0 to 12 , And when n is 2 or more, the plurality of R's may be the same or different from each other and fused with adjacent substituents to form a ring. The method according to claim 1,
The organic luminescent compound represented by the above formula (I) is any one selected from the following [compounds 1] to [41]:

[Compound 1] [Compound 2] [Compound 3]

[Compound 4] [Compound 5] [Compound 6]

[Compound 7] [Compound 8] [Compound 9]

[Compound 10] [Compound 11] [Compound 12]

[Compound 13] [Compound 14] [Compound 15]

[Compound 16] [Compound 17] [Compound 18]

[Compound 19] [Compound 20] [Compound 21]

[Compound 22] [Compound 23] [Compound 24]

[Compound 25] [Compound 26] [Compound 27]

[Compound 28] [Compound 29] [Compound 30]

[Compound 31] [Compound 32] [Compound 33]

[Compound 34] [Compound 35] [Compound 36]

[Compound 37] [Compound 38] [Compound 39]

[Compound 40] [Compound 41] A first electrode; A second electrode facing the first electrode; And at least one organic layer interposed between the first electrode and the second electrode,
The organic electroluminescent device according to claim 1, wherein the at least one organic layer comprises at least one organic electroluminescent compound represented by formula (I) according to claim 1. 9. The method of claim 8,
Wherein the organic layer includes at least one of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport functions, a light emitting layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection functions The organic electroluminescent device comprising: 9. The method of claim 8,
Wherein the organic layer interposed between the first electrode and the second electrode comprises a light emitting layer. 11. The method of claim 10,
Wherein the light emitting layer comprises at least one host compound and at least one dopant compound,
Wherein the at least one host compound and at least one dopant compound are selected from the organic luminescent compounds represented by the formula (I). 12. The method of claim 11,
The light emitting layer may further include at least one dopant compound selected from an organic compound having an organic luminescent compound represented by Formula (I), at least one host compound selected from anthracene derivatives, pyrene derivatives, and fluorene derivatives, and an arylamine derivative To the organic electroluminescent device. 9. The method of claim 8,
Wherein the one or more organic layers are independently formed by a single molecular deposition method or a solution process. 9. The method of claim 8,
Wherein the organic layer further comprises one or more organic light emitting layers emitting red, green or blue light to emit white light. 9. The method of claim 8,
Wherein the organic electroluminescent device is used in a device selected from a flat panel display device, a flexible display device, a monochromatic or white flat panel illumination device, and a monochromatic or white flexible illumination device.

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