KR101536163B1 - New organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Abstract

상기 유기발광화합물은 인광 호스트 물질로서 유기전기발광소자에 적용될 수 있으며, 이 경우 유기전기발광소자의 발광효율 및 소자 수명을 향상시킬 수 있다.
The present invention provides an organic electroluminescent compound represented by the following Formula 1 and an organic electroluminescent device comprising the same:
[Chemical Formula 1]

The organic luminescent compound may be applied to an organic electroluminescent device as a phosphorescent host material. In this case, the luminescent efficiency and lifetime of the organic electroluminescent device can be improved.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same.

The present invention relates to a novel organic light emitting compound and an organic electroluminescent device including the same.

The most important factor determining the luminous efficiency in an OLED is a light emitting material. Fluorescent materials are widely used as luminescent materials to date, but the development of a phosphorescent material on the mechanism of electroluminescence is one of the best ways to improve the luminous efficiency up to 4 times theoretically. Until now, iridium (III) complexes have been widely known as phosphorescent materials. Materials such as (acac) Ir (btp) 2, Ir (ppy) 3 and Firpic are known for each RGB. Recently, many phosphorescent materials have been studied in Japan and Europe.

CBP is the most widely known host material for a phosphorescent light emitting material, and a high efficiency OLED using a hole blocking layer such as BCP and BAlq is known. In Pioneer Japan, a high performance OLED using a BAlq derivative as a host is known .

However, existing materials have advantages in terms of luminescent properties, but they have disadvantages such as low glass transition temperature and very poor thermal stability, which can cause material changes when subjected to a high temperature deposition process under vacuum. Because OLEDs have power efficiency = (π / voltage) ㅧ current efficiency, the power efficiency is inversely proportional to the voltage. OLEDs using real phosphorescent materials have significantly higher current efficiency (cd / A) than OLEDs using fluorescent materials. However, when conventional materials such as BAlq and CBP are used as hosts for phosphorescent materials, OLEDs using fluorescent materials (Lm / w) because the driving voltage is higher than that of the conventional device. In addition, since the lifetime of the OLED device is never satisfactory, development of a more stable and more excellent host material is required.

The present invention relates to a novel organic electroluminescent compound which can be applied to an organic electroluminescent device as a phosphorescent host material and can lower a driving voltage when applied to an organic electroluminescent device and can improve luminous efficiency, brightness, thermal stability, The purpose is to provide.

It is another object of the present invention to provide an organic light emitting device employing the above compound.

The present invention provides an organic electroluminescent compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In this formula,

One of X and Y is a nitrogen atom and the other is a carbon atom or a simple bond substituted by at least one C1 to C5 alkyl group;

R1 or R2 is

A halogen atom, a nitrile, CF ₃ , Si (CH ₃ ) ₃ or Si (C ₆ H ₅ ) _3, or a hydrogen atom, a linear or branched alkyl group having from 1 to 10 carbon atoms,

,

,

,

,

,

,

,

,

,

,

,

또는

이거나,Heavy hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3, Si (C 6 H 5) 3, substituted or unsubstituted alkyl of C1 ~ C5 ring is phenyl, by Phenyl, naphthyl, phenanthrenyl, and the like substituted or unsubstituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, And examples thereof include fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole , quinoline, _{indole, -Si (C 6 H 5)} 3,

,

,

,

,

,

,

,

,

,

,

,

or

Lt; / RTI &

,

,

,

,

,

,

,

,

,

,

,

및

로 이루어진 군으로부터 선택되는 하나 이상으로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이며, X가 하나 이상의 C1~C5의 알킬기로 치환된 탄소원자 또는 단순결합인 경우 R1은 부존재이며, Y가 하나 이상의 C1~C5의 알킬기로 치환된 탄소원자 또는 단순결합인 경우 R2는 부존재이며;Small wish Here, linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3, Si (C 6 H 5) 3, substituted or unsubstituted alkyl of C1 ~ C5-substituted phenyl, Phenyl, naphthyl, phenanthrenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole and triazole , Fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, imidazole, quinoline, _{indole, -Si (C 6 H 5)} 3,

,

,

,

,

,

,

,

,

,

,

,

And

Or a heteroaryl group having 5 to 60 carbon atoms, and when X is a carbon atom or a simple bond substituted by at least one C1 to C5 alkyl group, R1 is absent , When Y is a carbon atom substituted by at least one C1 to C5 alkyl group or a simple bond, R2 is absent;

R3 and R4 are, each independently, a hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3 or Si (C ₆ H _{5) 3,} or,

Small wish chair, C1 ~ C10 linear or branched alkyl, halogen, _{nitrile, CF 3, Si (CH 3} ) 3, Si (C 6 H 5) 3, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl Phenyl, naphthyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, cyano, , Pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline or indole group, and R3 And R4 may be connected to form a benzene ring or a naphthalene ring;

R5 and R6 are, each independently, a hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3 or Si (C ₆ H _{5) 3,} or,

Small wish chair, C1 ~ C10 linear or branched alkyl, halogen, _{nitrile, CF 3, Si (CH 3} ) 3, Si (C 6 H 5) 3, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl Phenyl, naphthyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, cyano, , Pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, indole, quinolinyl, Lt; / RTI >

Wherein R7 and R9 are, each independently, a hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3 or _{Si (C 6 H 5) 3} .

Further, according to the present invention,

An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

At least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more.

The organic electroluminescent compound according to the present invention can be applied to an organic electroluminescent device as a phosphorescent host material. When applied to an organic electroluminescent device, the electroluminescent compound lowers a driving voltage and improves luminous efficiency, brightness, thermal stability, and device life.

In addition, the organic electroluminescent device manufactured using the organic electroluminescent compound of the present invention has high efficiency and long life.

The present invention relates to organic electroluminescent compounds represented by the following general formula (1)

[Chemical Formula 1]

In this formula,

One of X and Y is a nitrogen atom and the other is a carbon atom or a simple bond substituted by at least one C1 to C5 alkyl group;

R1 or R2 is

A halogen atom, a nitrile, CF ₃ , Si (CH ₃ ) ₃ or Si (C ₆ H ₅ ) _3, or a hydrogen atom, a linear or branched alkyl group having from 1 to 10 carbon atoms,

,

,

,

,

,

,

,

,

,

,

,

또는

이거나,Heavy hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3, Si (C 6 H 5) 3, substituted or unsubstituted alkyl of C1 ~ C5 ring is phenyl, by Phenyl, naphthyl, phenanthrenyl, and the like substituted or unsubstituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, And examples thereof include fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole , quinoline, _{indole, -Si (C 6 H 5)} 3,

,

,

,

,

,

,

,

,

,

,

,

or

Lt; / RTI &

,

,

,

,

,

,

,

,

,

,

,

및

로 이루어진 군으로부터 선택되는 하나 이상으로 치환된 6~30의 아릴기 또는 5~60의 헤테로아릴기이며, X가 하나 이상의 C1~C5의 알킬기로 치환된 탄소원자 또는 단순결합인 경우 R1은 부존재이며, Y가 하나 이상의 C1~C5의 알킬기로 치환된 탄소원자 또는 단순결합인 경우 R2는 부존재이며;Small wish Here, linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3, Si (C 6 H 5) 3, substituted or unsubstituted alkyl of C1 ~ C5-substituted phenyl, Phenyl, naphthyl, phenanthrenyl which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole and triazole , Fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, imidazole, quinoline, _{indole, -Si (C 6 H 5)} 3, -Si (C 6 H 5) 3,

,

,

,

,

,

,

,

,

,

,

,

And

Or a heteroaryl group having 5 to 60 carbon atoms, and when X is a carbon atom or a simple bond substituted by at least one C1 to C5 alkyl group, R1 is absent , When Y is a carbon atom substituted by at least one C1 to C5 alkyl group or a simple bond, R2 is absent;

R3 and R4 are, each independently, a hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3 or Si (C ₆ H _{5) 3,} or,

Small wish chair, C1 ~ C10 linear or branched alkyl, halogen, _{nitrile, CF 3, Si (CH 3} ) 3, Si (C 6 H 5) 3, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl Phenyl, naphthyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, cyano, , Pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline or indole group, and R3 And R4 may be connected to form a benzene ring or a naphthalene ring;

R5 and R6 are, each independently, a hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3 or Si (C ₆ H _{5) 3,} or,

Small wish chair, C1 ~ C10 linear or branched alkyl, halogen, _{nitrile, CF 3, Si (CH 3} ) 3, Si (C 6 H 5) 3, phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl Phenyl, naphthyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl substituted or unsubstituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, cyano, , Pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, indole, quinolinyl, Lt; / RTI >

Wherein R7 and R9 are, each independently, a hydrogen atom, a linear or branched alkyl, halogen, nitrile of _{C1 ~ C10, CF 3, Si} (CH 3) 3 or _{Si (C 6 H 5) 3} .

,

,

,

,

,

,

,

,

,

,

,

,

,

또는

일 수 있다.In the organic luminescent compound of the present invention, preferably, the aryl group or the heteroaryl group having 6 to 30 carbon atoms is phenyl, naphthyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, Benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, benzothiazole,

,

,

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,

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,

,

or

Lt; / RTI >

More preferably in the organic luminescent compound of the present invention,

Wherein R1 or R2 is

,

,

,

,

또는

이거나,Substituted or unsubstituted pyridinyl, pyrimidinyl, triazinyl, benzothiazole, carbazole, benzimidazole, benzothiazole, imidazole, imidazole, imidazole,

,

,

,

,

or

Lt; / RTI &

,

,

,

및

로 이루어진 군으로부터 선택되는 하나 이상으로 치환된 페닐, 나프틸, 트리아지닐,

,

또는

이며, X가 하나 이상의 C1~C5의 알킬기로 치환된 탄소원자 또는 단순결합인 경우 R1은 부존재이며, Y가 하나 이상의 C1~C5의 알킬기로 치환된 탄소원자 또는 단순결합인 경우 R2는 부존재이며;Phenyl substituted with one or more substituents selected from the group consisting of phenyl, naphthyl and pyridinyl substituted or unsubstituted with C1 to C5 alkyl groups, phenyl substituted with C1 to C10 straight or branched alkyl, C1 to C10 alkyl, Decyl, triazinyl, triazole, benzoxazole, benzothiazole, carbazole, benzimidazole, indole,

,

,

,

And

Phenyl, naphthyl, triazinyl, < RTI ID = 0.0 >

,

or

And when X is a carbon atom or a simple bond substituted by at least one C1-C5 alkyl group, R1 is absent, and when Y is a carbon atom or a simple bond substituted by at least one C1-C5 alkyl group, R2 is absent;

R3 and R4 are connected to form a benzene ring or a naphthalene ring;

R5 and R6 each independently represent a hydrogen atom, a phenyl group substituted or unsubstituted with at least one phenyl group, a naphthyl group, a phenanthrenyl group substituted with at least one C1-C5 alkyl group, a pyridinyl group, a pyrimidinyl group, A pyrazinyl or isoquinolinyl group;

R7 and R9 may be a C1 to C5 linear or branched alkyl group.

The organic luminescent compound of the present invention can be usefully used as a phosphorescent host material,

In particular, phosphorescent green host materials or phosphorescent red host materials may be usefully employed.

The organic luminescent compound of the present invention may have the chemical structure shown in the following [first group (s)].

[First group (group)]

The present invention also relates to

An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,

Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of the present invention singly or in combination of two or more thereof.

The organic light emitting compound may be included in the light emitting layer as a phosphorescent host material.

The phosphorescent host material may be a green or red light emitting compound.

The organic electroluminescent device

An anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and a cathode stacked in this order.

Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the following examples do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which a cathode (a hole injection electrode), a hole injection layer (HIL) and / or a hole transport layer (HTL), a light emitting layer (EML) Preferably, an electron blocking layer (EBL) may be additionally provided between the anode and the light emitting layer, and an electron transport layer (ETL), an electron injection layer (EIL) or a hole blocking layer (HBL) have.

In the method of manufacturing an organic electroluminescence device according to the present invention, a cathode material is coated on the surface of a substrate by a conventional method to form a cathode. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness. As the material for the positive electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity may be used.

Next, a hole injection layer (HIL) material is formed on the surface of the anode by vacuum thermal deposition or spin coating using a conventional method. Examples of such hole injection layer materials include copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m-MTDATA), 4,4' Amino) phenoxybenzene (m-MTDAPB), starburst type amines such as 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine (TCTA), 4,4' Triphenylamine (2-TNATA) or IDE406 available from Idemitsu, for example.

A hole transport layer (HTL) material is vacuum-deposited or spin coated on the surface of the hole injection layer by a conventional method to form a hole transport layer. As the hole transporting layer material, bis (N- (1-naphthyl-n-phenyl)) benzidine (? -NPD), N, N'- -Benzidine (NPB) or N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-diphenyl-4,4'-diamine (TPD).

A light emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, a single luminescent material or a luminescent host material among the luminescent layer materials used may be a phosphorescent host material in the case of green and red, and the organic luminescent compound of the present invention may be used as a phosphorescent host material. In addition, tris (8-hydroxyquinolinolato) aluminum (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-diphenylethenyl) -1,1'-biphenyl) Spiro) material, spiro-DPVBi (spiro-4,4'-bis (2,2-diphenylethenyl) -1,1'- biphenyl), LiPBO (2- (2- benzoxazolyl) Phenol lithium salts), bis (diphenylvinyl) benzene, aluminum-quinoline metal complexes, imidazole, thiazole and oxazole metal complexes.

Among the light emitting layer materials, IDE102 and IDE105 available from Idemitsu as phosphorescent dopants and tris (2-phenylpyridine) iridium (III) (Ir (ppy ) 3), iridium (III) bis [(4,6-difluorophenyl) pyridinate-N, C-2 '] picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys Platy (II) octaethylporphyrin (PtOEP), TBE002 (Cobion), etc. may be used.

An electron transport layer (ETL) material is formed on the surface of the light emitting layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the electron transporting material to be used is not particularly limited, and tris (8-hydroxyquinolinolato) aluminum (Alq3) can be preferably used.

Alternatively, by further forming a hole blocking layer (HBL) between the light emitting layer and the electron transporting layer and using a phosphorescent dopant together with the light emitting layer, it is possible to prevent the phenomenon that the triplet excitons or holes are diffused into the electron transporting layer.

The hole blocking layer can be formed by vacuum thermal deposition and spin coating using a hole blocking layer material in a conventional manner. In the case of the hole blocking layer material, there is no particular limitation, but (8-hydroxyquinolinolato Lithium biphenoxide (BAlq), bathocuproine (BCP), LiF, etc. may be used as the lithium salt (Li), bis (8-hydroxy-2-methylquinolinonato)

An electron injection layer (EIL) material is formed on the surface of the electron transport layer by vacuum thermal deposition or spin coating using a conventional method. In this case, the material of the electron injection layer to be used is not particularly limited, and preferably materials such as LiF, Liq, Li2O, BaO, NaCl, and CsF can be used.

Finally, a negative electrode is formed on the surface of the electron injecting layer by vacuum thermal deposition using a conventional method.

At this time, as the negative electrode material to be used, lithium, aluminum, aluminum-lithium, calcium, magnesium, (Mg-Ag) or the like may be used. In the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode capable of transmitting light.

The organic electroluminescent device according to the present invention may be manufactured in the order as described above, that is, in the order of anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode, Electron injection layer / electron transporting layer / hole blocking layer / light emitting layer / hole transporting layer / hole injecting layer / anode.

Hereinafter, a method of synthesizing the compounds of the present invention will be described with reference to representative examples. However, the method of synthesizing the compounds of the present invention is not limited to the following exemplified methods, and the compounds of the present invention can be produced by the methods exemplified below and by methods known in the art.

Synthetic example  1: Synthesis of Compound 1 [Reaction Scheme 1]

Preparation of intermediate compound [1-1]

In a nitrogen flask, 50 g (327.69 mmol) of compound 8-chloroimidazo [1,2-a] pyridine, 82 g (491.15 mmol) of (2-nitrophenyl) boronic acid, tetrakis (triphenylphosphine) palladium g (6.55 mmol) of potassium carbonate, 67.9 g (491.15 mmol) of potassium carbonate, 50 mL of distilled water and 500 mL of tetrahydrofuran, and the mixture was stirred at 50 DEG C for 24 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, and 50.9 g (65%) of intermediate compound [1-1] as a yellow solid was produced using dichloromethane and methanol Respectively.

Preparation of intermediate compound [1-2]

50 g (209 mmol) of the compound [1-1], 109 mL (627 mmol) of triethylphosphite and 150 m of isopropylbenzene were placed in a reaction flask and stirred at 150 ° C for 12 hours. After completion of the reaction, the reaction solution is concentrated under reduced pressure. The concentrate was separated and purified by column chromatography to obtain 30.3 g (70%) of intermediate compound [1-2] as a yellow solid.

Preparation of compound [1]

In a nitrogen atmosphere, 3 g (14.47 mmol) of the compound [1-2] and 60 mL of dimethylformamide are placed in a reaction flask, and the mixture is suspended and stirred. 947 mg (21.7 mmol) of sodium hydride was added to the reaction solution, stirred for 20 minutes, 6 g (533.49 mmol) of 2-chloro-4,6-diphenyltriazine was added thereto, and the mixture was stirred for 4 hours. After completion of the reaction, 60 mL of distilled water is added and stirred for 30 minutes. The resulting solid is filtered and washed with purified water and methanol. The filtered solid was recrystallized from toluene to obtain 3 g (78%) of the target compound [1] as a white solid.

Synthetic example  2: Compound 3  synthesis

To the reaction flask, 3 g (14.47 mmol) of the compound [1-2], 5.9 g (17.36 mmol) of 2- (3-chlorophenyl) (0.27 g, 0.28 mmol), potassium t-butoxide (2 g, 21.7 mmol), and 50 mL of tri-t-butylphosphine (0.3 mL, 0.57 mmol) were added and refluxed with 60 mL of xylene for 12 hours. After completion of the reaction, saturated aqueous ammonium solution is poured into the reaction solution and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure. The concentrate was recrystallized from toluene to obtain 8.5 g (68%) of the target compound [3] as a white solid.

Synthesis Example 3: Synthesis of Compound 52

[Reaction Scheme 2]

Preparation of intermediate compound [2-1]

50 g (327.69 mmol) of the compound [2-1], 53.1 g (393.23 mmol) of 1- (2-aminophenyl) ethanone, 1.4 g (6.55 mmol) of palladium (II) acetate, 67.9 g mmol), 6.3 mL (13.1 mmol) of 50% tri-t-butylphosphine, and 600 mL of toluene under reflux for 24 hours. After completion of the reaction, saturated aqueous ammonium solution is poured into the reaction solution and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then purified by column chromatography to obtain 55.1 g (67%) of intermediate compound [2-1] as a yellow solid.

Preparation of intermediate compound [2-2]

 In a nitrogen atmosphere, 50 g (198.98 mmol) of the compound [2-1] and 600 mL of tetrahydrofuran are placed in a reaction flask and stirred. 99.4 mL (298.47 mmol) of 3M methylmagnesium chloride was slowly added dropwise to the reactor and stirred at room temperature for 24 hours. After completion of the reaction, the reaction solution is slowly poured into a saturated aqueous ammonium solution and the organic layer is separated with ethyl acetate. The organic layer is separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain 40.4 g (76%) of yellow intermediate compound [2-2].

Preparation of intermediate compounds [2-3], [2-4]

 In a nitrogen atmosphere, 40 g (149.62 mmol) of the compound [2-2] and 400 mL of dichloromethane are added to a reaction flask and stirred. 29.1 mL (448.86 mmol) of sulfonic acid was added to the reactor and stirred at room temperature for 12 hours. After completion of the reaction, the saturated aqueous ammonium solution was poured and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and then purified by column chromatography to obtain 14.5 g (39%) of intermediate compound [2-3] as white solid and 15.2 g (41%) of [2-4] as white solid.

Preparation of compound [52]

(12.03 mmol) of the compound [2-4] and 4.9 g (14.43 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine were obtained in the same manner as in Synthesis Example 2 ), 54 mg (0.24 mmol) of palladium (II) acetate, 1.7 g (18.04 mmol) of potassium t-butoxide, 0.23 mL (0.48 mmol) of 50% tri-t-butylphosphine and 60 mL of xylene. 3.9 g (68%) of the desired compound [52] was obtained.

Synthesis Example 4: Synthesis of Compound 151

[Reaction Scheme 4]

Intermediate Preparation of compound [3-1]

(19.09 mmol) of the compound 6H-imidazole [1,2-a] pyrrolo [2,3-e] pyridine, 2,2'-dibromo-9,9 ' (0.76 mmol) of potassium t-butoxide and 0.37 ml (0.76 mmol) of 50% tri-t-butylphosphine in the same manner as in Example 1, except that 9 g (19.09 mmol) of spirobi [fluorene], 85 mg ) And 100 mL of xylene, and the resultant product was separated and purified by column chromatography to obtain 5.6 g (54%) of intermediate compound [3-1] as a yellow solid.

Preparation of intermediate compound [3-2]

In a nitrogen atmosphere, 5.5 g (9.99 mmol) of the compound [3-1] and 100 mL of tetrahydrofuran were added to the reaction flask, and the mixture was completely cooled to -78 ° C. At the same temperature, 4.8 mL (11.99 mmol) of 2.5 M normal-butyl lithium was slowly added dropwise, followed by stirring for 10 minutes. 1.7 ml (11.99 mmol) of trimethylborate was added at the same temperature, and the mixture was stirred at room temperature. After completion of the reaction, the saturated aqueous ammonium solution was poured and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and dichloromethane and hexane were used to synthesize 2.5 g (49%) of an intermediate compound [3-2] as a white solid.

Preparation of compound [151]

In the same manner as in Synthesis Example 1, 2.5 g (4.85 mmol) of the compound [3-2], 1.3 g (4.85 mmol) of 2-chloro-4,6-diphenyltriazine, tetrakis (triphenylphosphine) (72%) of the target compound [151] as a white solid was obtained using 112 mg (0.09 mmol) of palladium, 1 g (7.27 mmol) of potassium carbonate, 5 mL of distilled water and 5 mL of 1,4-

Compounds 1 to 182 were prepared in the same manner as in Synthesis Examples 1 to 4, and the results are shown in [Table 2].

[Second group (group)]

Hereinafter, the present invention will be described in more detail by way of examples. However, the following examples are intended to further illustrate the present invention, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Comparative Example 1

Wherein the compound represented by the following formula (a) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / LiF (30 nm) / compound (30 nm) / compound a + compound 30 nm / ITO / 2-TNATA 0.5 nm) / Al (60 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning the substrate in acetone, isopropyl alcohol and pure water for 15 minutes each, Ozone was cleaned and used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer, α-NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by Formula (a) and a compound represented by Formula (c) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a light emitting layer with a thickness of 30 nm. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injection layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to produce an organic light emitting device as shown in the third table group. This is referred to as Comparative Sample 1.

Comparative Example 2

Wherein the compound represented by the following formula (b) is used as a phosphorescent green host and the compound represented by the following formula (c) is used as a phosphorescent green dopant, and 2-TNATA (4,4 ' (N, N'-di (naphthylene-1-yl) -N, N'-diphenylbenzidine) was used as a hole transport layer material (30 nm) / Alq ₃ (30 nm) / LiF (30 nm) / compound (30 nm) / compound (30 nm) / ITO / 2-TNATA 0.5 nm) / Al (60 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Washed and used. 2-TNATA was vacuum deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. A compound represented by the formula (a) and a compound represented by the formula (c) (doping ratio: 10%) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq ₃ compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in the following [third group (group)]. This is referred to as Comparative Sample 2.

Comparative Example 3

2-TNATA (4,4 ', 4 "-tris (N-naphthalen-2-yl) thiophene) is used as a host by using a compound represented by the formula -N-phenylamino) -triphenylamine was used as a hole injection layer material and? -NPD (naphthalene-1-yl) -N, N'-diphenylbenzidine was used as a hole transport layer material, (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / Al (30 nm) / Compound (a) 60 nm).

The anode was prepared by cutting Corning's 15 Ω / cm ² (1000 Å) ITO glass substrate to a size of 50 mm × 50 mm × 0.7 mm and ultrasonically cleaning it in acetone, isopropyl alcohol and pure water for 15 minutes each, Washed and used. 2-TANATA was vacuum-deposited on the substrate to form a hole injection layer having a thickness of 80 nm. On top of the hole injection layer,? -NPD was vacuum deposited to form a hole transport layer having a thickness of 30 nm. Compound (a) represented by Formula (a) and Compound d (10% doped) represented by Formula (d) were vacuum deposited on the hole transport layer to form a 30 nm thick light emitting layer. Then, an Alq3 compound was vacuum deposited on the light emitting layer to a thickness of 30 nm to form an electron transporting layer. LiF 0.5 nm (electron injecting layer) and Al 60 nm (cathode) were sequentially vacuum-deposited on the electron transporting layer to form an organic light emitting device as shown in the third table group (third group). This is referred to as Comparative Sample 3.

Example 1 ~ 153.

In the same manner as in Comparative Example 1 except that phosphorescent green host compounds were used instead of the phosphorescent host compound a in the above-mentioned synthesis example in the above Comparative Example 1, ITO / 2-TNATA (30 nm) / Alq ₃ (30 nm) / LiF (0.5 nm) / Al (80 nm) /? -NPD (30 nm) / [phosphorescent green host compound 1 to 153 + compound c 60 nm) was fabricated. These are referred to as Samples 1 to 153, respectively.

Evaluation Example 1: Evaluation of luminescence characteristics of Comparative Samples 1 and 2 and Samples 1 to 153

The luminescence brightness, the luminescence efficiency and the luminescence peak were evaluated using Keithleysourcemeter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 1 to 153, Group)]. The samples showed green emission peak values in the 511 to 517 nm range.

[Group 3]

Samples 1 to 153 exhibited improved luminescence characteristics as compared to Comparative Samples 1 and 2, as shown in the [third set of group (s)] above.

Evaluation Example 2: Evaluation of life characteristics of Comparative Samples 1 and 2 and Samples 1 to 153

Comparative samples 1 and 2 and samples 1 to 153 were measured for time to reach 97% of life on the basis of 3000 nits using an LTS-1004AC life measuring device manufactured by ENC technology, and the results are shown in the following [ (Group)].

[Group 4]

Samples 1 to 153 exhibited improved lifespan characteristics as compared to Comparative Samples 1 and 2, as shown in the [fourth set of group (s)] above.

Examples 154-162.

In the same manner as in Comparative Example 3, except that the compounds represented by the chemical formulas 154 to 162 shown in the above synthesis examples were used as the host compound in the light emitting layer instead of the compound a as the phosphorescent host compound in the light emitting layer in Comparative Example 3, An organic light emitting device having a structure of TNATA (80 nm) /? -NPD (30 nm) / [one of host compounds 154 to 162 + compound d] (30 nm) / Alq3 (30 nm) / LiF (0.5 nm) / Al . These are referred to as Samples 154 to 162, respectively.

Evaluation Example 3: Evaluation of luminescence characteristics of Comparative Sample 3 and Samples 154 to 162

Comparative Example 3 and Samples 154 to 162 were evaluated for light emission luminance, luminous efficiency and emission peak using Keithley SMU 235 and PR650, respectively, and the results are shown in the following [fifth group (group)]. The samples showed a red emission peak value in the range of 610 to 616 nm.

[Fifth group (group)]

Samples 154 to 162 exhibited the same level of luminescence characteristics as those of Comparative Sample 3, as shown in the above [fifth group (group)].

Evaluation Example 4: Evaluation of life characteristics of Comparative Sample 3 and Samples 154 to 162

The life span of the comparative sample 3 and the samples 154 to 162 was evaluated by using a life evaluation device (LTS-1004C) in a DC mode in which the intensity of light emission decreased to 70% of the initial value based on the luminance of 5000 nits, The results are shown below in the sixth group (group).

[Group 6]

Samples 154 to 162 showed improved lifetime characteristics as compared to Comparative Sample 3, as shown in the [sixth set of group (s)] above.

Claims (10)

An organic light-emitting compound represented by the following formula (1):
[Chemical Formula 1]

In this formula,
One of X and Y is a nitrogen atom and the other is a carbon atom or a simple bond substituted by at least one C1 to C5 alkyl group;
R1 or R2 is
Substituted or unsubstituted phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, imidazole, imidazole, Pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, Triazole, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole, -Si (C ₆ H ₅ ) _3,

,

,

,

,

,

,

,

,

,

,

,

or

Lt; / RTI &
Substituted or unsubstituted phenyl, biphenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, Substituted or unsubstituted phenyl, naphthyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole (C ₆ H ₅ ) ₃ , -Si (C ₆ H ₅ ) ₃ , -Si (C ₆ H ₅ ), and the like. _3,

,

,

,

,

,

,

,

,

,

,

,

And

, Or a C5-60 heteroaryl group, and when X is a carbon atom or a simple bond substituted by at least one C1-C5 alkyl group, R1 is absent , When Y is a carbon atom substituted by at least one C1 to C5 alkyl group or a simple bond, R2 is absent;
R3 and R4 are hydrogen atoms, R3 and R4 may be connected to form a benzene ring or a naphthalene ring;
R5 and R6 are each independently a hydrogen atom,
Phenyl, naphthyl, phenanthryl, substituted or unsubstituted phenyl optionally substituted with one or more substituents selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, Thienyl, thiazol, benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, dibenzothiophene, dibenzothiophene, dibenzothiophene, Benzimidazole, indole, quinolinyl, or isoquinolinyl group;
R7 and R8 are each independently a hydrogen atom, a C1-C10 linear alkyl group, or a C3-C10 branched chain alkyl group. The method according to claim 1,
The aryl group or the C5-60 heteroaryl group of the C6-30 aryl group may be substituted with a substituent selected from the group consisting of phenyl, naphthyl, phenanthrenyl, fluorenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, imidazole, triazole , Benzoxazole, benzothiazole, carbazole, dibenzofuran, dibenzothiophene, benzimidazole, quinoline, indole,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

≪ / RTI > delete The method according to claim 1,
Wherein the organic light emitting compound is any one of the following compounds 1 to 182:

The method according to claim 1,
Wherein the organic light emitting compound is a phosphorescent host material in a material for an organic electroluminescence device. 6. The method of claim 5,
Wherein the phosphorescent host material is a green or red luminescent compound. An organic electroluminescent device in which an organic thin film layer composed of one layer or a plurality of layers including at least a light emitting layer is sandwiched between a cathode and an anode,
Wherein at least one of the organic thin film layers contains the organic electroluminescent compound of claim 1 singly or in combination of two or more. 8. The method of claim 7,
Wherein the organic electroluminescent compound is contained in the light emitting layer as a phosphorescent host material. 9. The method of claim 8,
Wherein the phosphorescent host material is a green or red luminescent compound. 10. The method according to any one of claims 7 to 9,
The organic electroluminescent device
Wherein the anode, the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, the electron injecting layer, and the cathode are stacked in this order.