KR101551466B1 - New organic electroluminescent compounds and organic electroluminescent device comprising the same - Google Patents

Abstract

[화학식2]

상기 유기발광화합물은 인광 녹색 호스트 물질, 형광 녹색 호스트 물질, 정공주입층 물질 및 정공수송층 물질로서 유기전기발광소자에 적용될 수 있으며, 이 경우 유기전기발광소자의 발광효율 및 소자 수명을 향상시킬 수 있다.
The present invention provides organic electroluminescent compounds represented by the following general formulas (1) and (2) and organic electroluminescent devices comprising the same:
[Chemical Formula 1]

(2)

The organic electroluminescent compound may be applied to an organic electroluminescent device as a phosphorescent green host material, a fluorescent green host material, a hole injecting layer material, and a hole transporting layer material. In this case, the luminous 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, and more particularly, to a novel organic light emitting compound used as a green light emitting material and an organic light emitting device employing the same.

Generally, an organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. That is, when a voltage is applied between the two electrodes when the organic layer is positioned between the anode and the cathode, holes are injected into the organic layer and holes are injected into the organic layer. When the injected holes and electrons meet, an exciton is formed. When the exciton falls back to the ground state, light is emitted.

In 1950, Bernanose observed the emission of organic thin films by applying a high alternating voltage to organic thin films. In 1965, an anthracene single crystal was injected with current to generate singlet excitons, ≪ / RTI >

As a method for efficiently forming an organic light emitting device, research has been conducted to manufacture an organic material layer in a device in a multilayer structure instead of a single layer. In 1987, an organic electroluminescent device having a multilayer structure divided into a hole layer and a functional layer of a light emitting layer by Tang has been proposed. Most organic light emitting devices currently used include a substrate, an anode, and a hole An electron transport layer for selectively transporting electrons, an electron injection layer for receiving electrons from the cathode, and a cathode. The electron transport layer includes a hole injection layer, a hole transport layer for selectively transporting holes, a light emission layer for recombining holes and electrons,

The reason why the EL elements are formed in a multilayer structure is that the moving speeds of holes and electrons are different from each other. Therefore, when an appropriate hole injecting layer, a transfer layer, an electron transporting layer and an electron injecting layer are formed, holes and electrons can be effectively transferred. The balance between the holes and the electrons can be balanced to increase the luminous efficiency.

The electrons injected from the electron injecting layer and the holes injected from the hole injecting layer recombine to form excitons in the light emitting layer. The excitons fall from the singlet excited state to the ground state, and emit light is referred to as fluorescence. In the triplet excited state, Luminescence is referred to as phosphorescence. Theoretically, when carriers are recombined in the light emitting layer and excitons are generated, the ratio of singlet and triplet excitons is generated at a ratio of 1: 3. When phosphorescent emission is used, the internal quantum efficiency can be increased up to 100%.

In general, a carbazole ring compound such as CBP (4,4-dicarbazolylbiphenyl) is used as a phosphorescent host material, and a metal complex compound containing a heavy atom such as Ir or Pt is widely used as a phosphorescent guest material.

However, CBP, which is a phosphorescent host material currently used, has a low Tg of about 110 DEG C and crystallization in the device is easily occurred, and thus the lifespan of the organic electroluminescent device is extremely short to about 150 hours.

The present invention can be applied to an organic light emitting device as a phosphorescent green host material, a fluorescent green host material, a hole injecting layer material, or a hole transporting layer material. When applied to an organic light emitting device, a driving voltage can be lowered. , An organic luminescent compound capable of improving thermal stability and device lifetime.

Another object of the present invention is to provide an organic light emitting device using 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,

X and Y are each independently a carbon atom substituted or unsubstituted with a nitrogen atom, an oxygen atom, a sulfur atom, at least one C1 to C10 straight chain alkyl group or a C3 to C10 branched alkyl group, or a simple bond, , An oxygen atom, a sulfur atom or a simple bond, R1 and R2 are absent, and when Y is the carbon atom, the oxygen atom, the sulfur atom or the simple bond, R3 and R4 are absent;

Z is a nitrogen atom or a carbon atom;

O, P and Q are each independently a nitrogen atom or a carbon atom;

A, B, C and D are absent or carbon atoms;

R1 and R3 are each independently a simple bond,

(C1-C10) straight chain alkyl, C3-C10 branched alkyl, C1-C10 alkoxy, halogen, nitrile, CF3, Si (CH3) 3, phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole , Imidazole, triazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzothiazole, carbazole, quinolinyl, isoquinoline An arylene group having 6 to 30 carbon atoms or a heteroarylene group having 5 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen, an indole, and a pyrenyl group;

,

또는

이며;

,

or

;

R2 and R4 are each independently selected from the group consisting of deuterium atoms, C1 to C10 linear alkyls, C3 to C10 branched alkyls, C1 to C10 alkoxy, halogen, nitrile, CF3, Si (CH3) 3, phenyl, naphthyl, Pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, ≪ / RTI > or is unsubstituted or substituted with one or more substituents selected from the group consisting of

From the group consisting of phenyl, pyridinyl, pyrimidinyl and triazinyl groups substituted with one or more substituents selected from the group consisting of phenyl, phenoxy, phenyl mercapto (ph-s-), biphenyl, triphenyl and pyridinyl groups An aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected;

이며, 상기 Ar1 및 Ar2는 각각 독립적으로 C1~C10의 직쇄 알킬, C3~C10의 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3및 Si(CH3)3로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 나프틸, 페난트레닐, 플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 벤조티오페닐, 벤즈이미다졸, 벤조옥사졸, 벤즈티아졸, 카바졸, 퀴놀리닐, 이소퀴놀리닐, 인돌 또는 피레닐기이며;

, Ar1 and Ar2 are each independently selected from the group consisting of C1 to C10 linear alkyl, C3 to C10 branched alkyl, C1 to C10 alkoxy, halogen, nitrile, CF3 and Si (CH3) Substituted or unsubstituted phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothio Phenyl, benzimidazole, benzoxazole, benzothiazole, carbazole, quinolinyl, isoquinolinyl, indole or pyrenyl group;

R5 and R6 are each independently selected from the group consisting of hydrogen, deuterium atoms, C1 to C10 linear alkyl, C3 to C10 branched alkyl, C1 to C10 alkoxy, halogen, nitrile, CF3, Si (CH3) Thiadiazole, pyrazinyl, pyridazinylpyridinyl, pyrimidinyl and triarylpiperazinyl, pyrimidinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, Gt; is optionally substituted with one or more substituents selected from the group consisting < RTI ID = 0.0 > of: < / RTI &

From the group consisting of phenyl, pyridinyl, pyrimidinyl and triazinyl groups substituted with one or more substituents selected from the group consisting of phenyl, phenoxy, phenyl mercapto (ph-s-), biphenyl, triphenyl and pyridinyl groups An aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected,
Provided that when Q is nitrogen, R < 6 > does not exist.

The present invention provides an organic electroluminescent compound represented by the following general formula (2): < EMI ID =

(2)

In this formula,

X and Y are a nitrogen atom or a carbon atom; X and Y can not be the same atom; when X is a carbon atom, R1 and R2 are absent; when Y is a carbon atom, R3 and R4 are absent;

O, P, Q and R are each independently a nitrogen atom or a carbon atom;

R1, R3 and R5 are each independently a simple bond,

A straight chain alkyl of C1 to C10, a branched chain alkyl of C3 to C10, a C1 to C10 alkoxy, a halogen, a nitrile, CF3, Si (CH3) 3, phenyl, pyridinyl, pyrimidinyl, pyrazinyl, A pyridinylene, a pyrimidinylene, a pyrazinylene, a pyridazinylene, a triazienylene, a naphthylene or a phenanthrenylene group substituted or unsubstituted with at least one substituent selected from the group consisting of a nitrogen atom and a nitrogen atom;

R2, R4 and R6 are each independently selected from the group consisting of C1 to C10 linear alkyl, C3 to C10 branched alkyl, C1 to C10 alkoxy, halogen, nitrile, CF3, Si (CH3) 3, phenyl, pyridinyl, pyrimidinyl , Phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl or phenanthrenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of pyridinyl, pyridazinyl and triazinyl groups to be.

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 green host material, a fluorescent green host material, a hole injecting layer material, or a hole transporting layer material. When applied to an organic light emitting device, 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,

X and Y are each independently a carbon atom substituted or unsubstituted with a nitrogen atom, an oxygen atom, a sulfur atom, at least one C1 to C10 straight chain alkyl group or a C3 to C10 branched alkyl group, or a simple bond, , An oxygen atom, a sulfur atom or a simple bond, R1 and R2 are absent, and when Y is the carbon atom, the oxygen atom, the sulfur atom or the simple bond, R3 and R4 are absent;

Z is a nitrogen atom or a carbon atom;

O, P and Q are each independently a nitrogen atom or a carbon atom;

A, B, C and D are absent or carbon atoms;

R1 and R3 are each independently a simple bond,

(C1-C10) straight chain alkyl, C3-C10 branched alkyl, C1-C10 alkoxy, halogen, nitrile, CF3, Si (CH3) 3, phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole , Imidazole, triazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzothiazole, carbazole, quinolinyl, isoquinoline An arylene group having 6 to 30 carbon atoms or a heteroarylene group having 5 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of a halogen, an indole, and a pyrenyl group;

,

또는

이며;

,

or

;

R2 and R4 are each independently selected from the group consisting of deuterium atoms, C1 to C10 linear alkyls, C3 to C10 branched alkyls, C1 to C10 alkoxy, halogen, nitrile, CF3, Si (CH3) 3, phenyl, naphthyl, Pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, ≪ / RTI > or is unsubstituted or substituted with one or more substituents selected from the group consisting of

From the group consisting of phenyl, pyridinyl, pyrimidinyl and triazinyl groups substituted with one or more substituents selected from the group consisting of phenyl, phenoxy, phenyl mercapto (ph-s-), biphenyl, triphenyl and pyridinyl groups An aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms, which is substituted or unsubstituted with at least one substituent selected;

이며, 상기 Ar1 및 Ar2는 각각 독립적으로 C1~C10의 직쇄 알킬, C3~C10의 분지쇄 알킬, C1~C10의 알콕시, 할로겐, 니트릴, CF3및 Si(CH3)3로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 치환 또는 비치환된 페닐, 나프틸, 페난트레닐, 플루오레닐, 피롤, 피라졸, 이미다졸, 트리아졸, 피리디닐, 피리미디닐, 피라지닐, 피리다지닐, 트리아지닐, 벤조티오페닐, 벤즈이미다졸, 벤조옥사졸, 벤즈티아졸, 카바졸, 퀴놀리닐, 이소퀴놀리닐, 인돌 또는 피레닐기이며;

, Ar1 and Ar2 are each independently selected from the group consisting of C1 to C10 linear alkyl, C3 to C10 branched alkyl, C1 to C10 alkoxy, halogen, nitrile, CF3 and Si (CH3) Substituted or unsubstituted phenyl, naphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothio Phenyl, benzimidazole, benzoxazole, benzothiazole, carbazole, quinolinyl, isoquinolinyl, indole or pyrenyl group;

R5 and R6 are each independently selected from the group consisting of hydrogen, deuterium atoms, C1 to C10 linear alkyl, C3 to C10 branched alkyl, C1 to C10 alkoxy, halogen, nitrile, CF3, Si (CH3) Thiadiazole, pyrazinyl, pyridazinylpyridinyl, pyrimidinyl and triarylpiperazinyl, pyrimidinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, pyridazinyl, Gt; is optionally substituted with one or more substituents selected from the group consisting < RTI ID = 0.0 > of: < / RTI &

From the group consisting of phenyl, pyridinyl, pyrimidinyl and triazinyl groups substituted with one or more substituents selected from the group consisting of phenyl, phenoxy, phenyl mercapto (ph-s-), biphenyl, triphenyl and pyridinyl groups An aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms which is substituted or unsubstituted with at least one substituent selected,
Provided that when Q is nitrogen, R < 6 > does not exist.

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

및

로 이루어진 군으로부터 선택되며, 상기에서 R7, R8, R9, R10, R11, R12, R13 및 R14는 각각 독립적으로 수소, C1~C10의 직쇄 알킬기 또는 C3~C10의 분지쇄 알킬기일 수 있다. The heteroaryl of 6 to 30 carbon atoms or the heteroaryl of 5 to 60 carbon atoms is preferably selected from phenyl, naphthyl, biphenyl, binaphthyl, phenanthrenyl, fluorenyl, pyrrole, pyrazole, imidazole, triazole, oxazole, Benzothiazole, benzothiazole, carbazole, benzothiazole, thiadiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, Quinolinyl, isoquinolinyl, indole, pyrenyl,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

And

Wherein R7, R8, R9, R10, R11, R12, R13 and R14 are each independently hydrogen, a C1-C10 straight-chain alkyl group or a C3-C10 branched-chain alkyl group.

Here, the aryl group having 6 to 30 carbon atoms or the heteroaryl group having 5 to 60 carbon atoms is an aryl group having 6 to 30 carbon atoms, a heteroarylene group having 5 to 60 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 5 to 60 carbon atoms Means included.

More preferably, in Formula 1,

X and Y are each independently a carbon atom substituted or unsubstituted with a nitrogen atom, an oxygen atom, a sulfur atom, at least one C1 to C5 straight chain alkyl group or a C3 to C5 branched alkyl group, or a simple bond, , An oxygen atom, a sulfur atom or a simple bond, R1 and R2 are absent, and when Y is the carbon atom, the oxygen atom, the sulfur atom or the simple bond, R3 and R4 are absent;

Z is a nitrogen atom or a carbon atom;

O, P and Q are each independently a nitrogen atom or a carbon atom, with the proviso that O, P and Q are both carbon atoms or not both nitrogen atoms;

A, B, C and D are absent or carbon atoms;

R1 and R3 are each independently a simple bond,

,

또는

이며; Phenylene, naphthalene, biphenylene, binaphthalene, or biphenylene substituted or unsubstituted with at least one C1 to C5 straight-chain alkyl group or C3 to C5 branched alkyl group,

,

or

;

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

또는

이거나,R2 and R4 are each independently selected from the group consisting of C1-C10 linear alkyl, C3-C10 branched alkyl, Si (CH3) 3, phenyl, pyridinyl, phenoxy, phenylmercapto (ph- Phenyl, phenanthrenyl, pyrazole, oxazole, oxadiazole, thiophenyl, thiazole, thiadiazole, pyridinyl, pyrimidinyl, pyrimidinyl, Pyrazinyl, pyridazinyl, triazinyl, benzothiophenyl, benzimidazole, benzoxazole, benzothiazole, carbazole, quinolinyl, isoquinolinyl, indole,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

or

Lt; / RTI &

A phenyl group substituted with a triazinyl group substituted with two phenyl groups,

이며, 상기 Ar1 및 Ar2는 페닐기이며,

, Ar1 and Ar2 are phenyl groups,

R7, R8, R9, R10, R11, R12, R13 and R14 are each independently a C1-C5 straight-chain alkyl group or a C3-C5 branched-chain alkyl group;

R5 and R6 are each independently a phenyl group or a phenyl group substituted with a triazinyl group substituted with two phenyl groups.

The present invention relates to an organic luminescent compound represented by the following general formula (2)

(2)

In this formula,

X and Y are a nitrogen atom or a carbon atom; X and Y can not be the same atom; when X is a carbon atom, R1 and R2 are absent; when Y is a carbon atom, R3 and R4 are absent;

O, P, Q and R are each independently a nitrogen atom or a carbon atom;

R1, R3 and R5 are each independently a simple bond,

A straight chain alkyl of C1 to C10, a branched chain alkyl of C3 to C10, a C1 to C10 alkoxy, a halogen, a nitrile, CF3, Si (CH3) 3, phenyl, pyridinyl, pyrimidinyl, pyrazinyl, A pyridinylene, a pyrimidinylene, a pyrazinylene, a pyridazinylene, a triazienylene, a naphthylene or a phenanthrenylene group substituted or unsubstituted with at least one substituent selected from the group consisting of a nitrogen atom and a nitrogen atom;

R2, R4 and R6 are each independently selected from the group consisting of C1 to C10 linear alkyl, C3 to C10 branched alkyl, C1 to C10 alkoxy, halogen, nitrile, CF3, Si (CH3) 3, phenyl, pyridinyl, pyrimidinyl , Phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, naphthyl or phenanthrenyl group substituted or unsubstituted with at least one substituent selected from the group consisting of pyridinyl, pyridazinyl and triazinyl groups to be.

In Formula 2, more preferably,

X and Y are a nitrogen atom or a carbon atom; X and Y can not be the same atom; when X is a carbon atom, R1 and R2 are absent; when Y is a carbon atom, R3 and R4 are absent;

One of O, P, Q and R is a nitrogen atom and the other is a carbon atom;

R1, R3 and R5 are each independently a simple bond or a phenylene group;

R2, R4 and R6 are each independently a phenyl group, or a triazinyl group substituted with two phenyl groups.

The organic luminescent compound of the present invention can be usefully used as a phosphorescent green host material, a fluorescent green host material, a hole injection layer material, or a hole transport layer material.

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 organic electroluminescent device as a phosphorescent green host material, a fluorescent green host material, a hole injection layer material, or a hole transport layer material.

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. As the hole injection layer material, the organic light emitting compound of the present invention can be used. In addition, copper phthalocyanine (CuPc), 4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine (m- 4,4 ', 4 "-tris (3-methylphenylamino) phenoxybenzene (m-MTDAPB) which is a starburst type amine, 4,4' (TCTA), 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenylamino) -triphenylamine (2-TNATA) or IDE406 available from Idemitsu .

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. In this case, the hole transport layer material may be an organic light emitting compound of the present invention. In addition, the hole transport layer material may be an organic light emitting compound of the present invention, and examples thereof include bis (N- (1-naphthyl-n-phenyl) (NPB) or N, N'-biphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl- '-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, the organic luminescent compound of the present invention may be used as a phosphorescent or fluorescent green host material in the case of a single luminescent material or luminescent host material among the luminescent layer materials to be used. In addition, tris (8-hydroxyquinolinolato) aluminum (8q-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl) (Spiro-4,4'-bis (2,2-biphenylethenyl) -1,1'-biphenyl), LiPBO (2- (2-benzoxazolyl) - phenol lithium salt), bis (biphenylvinyl) benzene, aluminum-quinoline metal complex, 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.

Synthesis of Compound [1]

[Reaction Scheme 1]

Preparation of intermediate compound [1-1]

(0.373 mol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 70.0 g (0.448 mol) of 3-chlorophenylboronic acid and 77.3 g mol) was dissolved in 1 L of 1,4-dioxane, 560 mL of purified water was added, and 8.62 g (7.46 mmol) of tetrakis (triphenylphosphine) palladium was added thereto, followed by reflux stirring for 12 hours. After completion of the reaction, slowly cool to room temperature, and then filter the reaction solution. The filtered solid was washed with purified water and methanol, and recrystallized from dichloromethane and hexane and methanol to obtain 95 g (74%) of intermediate compound [1-1].

Preparation of compound [1]

Preparation of intermediate compound 5-bromo-l-phenyl-lH-pyrrolo [3,2-b] pyridine

(0.609 mol) of iodobenzene, 12.9 g (0.203 mol) of copper powder and 211 g (1.52 mol) of potassium carbonate were added to a solution of 5-bromo-lH- pyrrolo [3,2- And the mixture was refluxed with 1.5 L of dimethylformamide for 12 hours. The reaction solution is cooled to room temperature, and the organic layer is separated from ethyl acetate and saturated brine. The organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was crystallized from dichloromethane and methanol to obtain 194 g of intermediate compound 5-bromo-1-phenyl-lH-pyrrolo [3,2- 71%).

Preparation of intermediate compound 5- (2-nitrophenyl) -1-phenyl-lH-pyrrolo [3,2-b] pyridine

(0.575 mol) of 5-bromo-1-phenyl-1H-pyrrolo [3,2-b] pyridine, 80 g (0.479 mol) of 2-nitrobenzeneboronic acid and potassium carbonate (K2CO3) g (0.719 mol) was added to 1.5 L of 1,4-dioxane and stirred. 16.6 g (14.4 mmol) of tetrakis (triphenylphosphine) palladium is added at about 70 DEG C and 300 mL of purified water is added dropwise. The reaction was refluxed and stirred for 24 hours, then cooled to room temperature and extracted with ethyl acetate and saturated brine. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography (dichloromethane / hexane = 1/15) to obtain 124 g of intermediate compound 5- (2-nitrophenyl) -1-phenyl-lH- pyrrolo [3,2- b] (82%).

Preparation of intermediate compound [1-2]

100 g (0.317 mol) of the intermediate compound 5- (2-nitrophenyl) -1-phenyl-lH-pyrrolo [3,2-b] pyridine are added to 500 ml of cumene anhydride under nitrogen flow and stirred. Add 218 mL (1.27 mol) of triethylphosphite [P (OEt) 3] slowly to the reaction. After completion of the dropwise addition, the reaction mixture is refluxed and stirred for 24 hours. The reaction is cooled to room temperature and the solvent is concentrated under reduced pressure. The concentrate was crystallized from dichloromethane and hexane to give 58 g (65%) of the intermediate compound [1-2].

Preparation of compound [1]

50 g (0.176 mol) of the intermediate compound [2] and 74 g (0.212 mol) of the intermediate compound [1-1] 2- (3-chlorophenyl) 25.0 g (0.265 mol) of sodium tert-butoxide, 0.8 g (3.53 mmol) of palladium acetate and 3.5 mL (7.1 mmol) of 50% tri-tert-butylphosphine are dissolved in 1000 mL of xylene and refluxed with stirring for 3 hours. After completion of the reaction, dichloromethane was added to dissolve it, and the mixture was washed with purified water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized from dichloromethane and methanol to give 64.6 g (62%) of the desired compound [1] as a pale yellow solid.

Synthesis of Compound [117]

[Reaction Scheme 2]

Preparation of intermediate compound 5-bromo-1- (phenylsulfonyl) -lH-pyrrolo [3,2-b] pyridine [117-1]

To 100 mL of tetrahydrofuran was added 16.3 g (60% in mineral oil) (406 mmol) of sodium hydride and the mixture was stirred under a nitrogen stream. The reaction is cooled to 0 < 0 > C. 50 g (254 mmol) of 5-bromo-lH-pyrrolo [3,2-b] pyridine are dissolved in 200 mL of tetrahydrofuran, and then slowly added dropwise to the reaction mixture. After the dropwise addition is complete, the reaction is stirred at 0 < 0 > C for one hour. 53.8 g (305 mmol) of benzenesulfonyl chloride was added dropwise to the reaction mixture at the same temperature, and the mixture was stirred at room temperature for 4 hours. Saturated ammonium chloride is added to the reaction and extracted with ethyl acetate. The extracted organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by column chromatography (ethyl acetate / hexane = 1/4) to obtain the target compound intermediate 5-bromo-1- (phenylsulfonyl) -lH- pyrrolo [3,2- b] 117-1] (55.6 g, 65%).

Preparation of Intermediate 1- (2- (1- (phenylsulfonyl) -lH-pyrrolo [3,2-b] pyridin-5-yl) phenyl) ethanone

 50 g (148 mmol) of 2-acetylphenylboronic acid and 26.8 g (163 mmol) of 2-acetylphenylboronic acid were added to a solution of the intermediate 5-bromo-1- (phenylsulfonyl) , 30.7 g (223 mmol) of potassium carbonate are added to 1 L of 1,4-dioxane and the mixture is stirred. 1.7 g (1.5 mmol) of tetrakis (triphenylphosphine) palladium is added at about 80 DEG C and 200 mL of purified water is added dropwise. The reaction is refluxed and stirred for 12 hours and then cooled to room temperature. The saturated brine is added to the reaction and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography (dichloromethane / hexane = 1/10) to obtain the desired compound intermediate 1- (2- (1- (phenylsulfonyl) -lH-pyrrolo [3,2- b] -5-yl) phenyl) ethanone (33.5 g, 60%).

Preparation of intermediate 2- (2- (1- (phenylsulfonyl) -lH-pyrrolo [3,2-b] pyridin-5- yl) phenyl) propan-

 30 g (78 mmol) of Intermediate 1- (2- (1- (phenylsulfonyl) -lH-pyrrolo [3,2- b] pyridin-5- yl) phenyl) ethanone was dissolved in tetrahydrofuran 500 mL, and 114 mL (160 mmol) of methylmagnesium bromide (1.4 M in THF: toluene = 1: 3) is slowly added dropwise at room temperature. After stirring for 13 hours at room temperature, saturated ammonium chloride is added slowly to terminate the reaction and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography (dichloromethane / hexane = 1/5) to obtain the desired compound intermediate 2- (2- (1- (phenylsulfonyl) -lH- pyrrolo [3,2- b] Yl) phenyl) propan-2-ol (19.4 g, 62%).

Preparation of Intermediate 9,9-Dimethyl-l- (phenylsulfonyl) -l, 9-dihydroindeno [l, 2-b] pyrrolo [2,3- e]

 15 g (38 mmol) of the intermediate 2- (2- (1- (phenylsulfonyl) -lH-pyrrolo [3,2- b] pyridin-5- yl) phenyl) propan- Dissolve in 500 mL of methane and add 23 mL (344 mmol) of methanesulfonic acid slowly dropwise at room temperature. After completion of the dropwise addition, water is added to the reaction mixture, and the mixture is stirred for 30 minutes. The organic layer is separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was purified by column chromatography (dichloromethane / hexane = 1/10) to obtain the target compound intermediate 9,9-dimethyl-1- (phenylsulfonyl) -1,9-dihydroindeno [1,2 -b] pyrrolo [2,3-e] pyridine (7.7 g, 54%).

Preparation of intermediate 9,9-dimethyl-1,9-dihydroindeno [l, 2- b] pyrrolo [2,3-e] pyridine [117-2]

 Intermediate 7 g (18.7 mmol) of 9,9-dimethyl-l- (phenylsulfonyl) -l, 9-dihydroindeno [l, 2 -b pyrrolo [2,3- e] pyridine was dissolved in tetrahydrofuran , And 56.1 mL (1.0 M in tetrahydrofuran solution, 56.1 mmol) of tetrabutylammonium fluoride is slowly added to the reaction mixture. The reaction is stirred at ambient temperature for 3 hours. Water is added to the reaction mixture, and the mixture is stirred. The mixture is extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was purified by column chromatography (ethyl acetate / hexane = 1/10) to obtain the target compound intermediate 9,9-dimethyl-1,9-dihydroindeno [l, 2-b] pyrrolo [ 3-e] pyridine [117-2] (3.1 g, 72%).

Preparation of compound [117]

The intermediate compound 9,9-dimethyl-1,9-dihydroindeno [l, 2- b] pyrrolo [2,3-e] pyridine [117-2] (10 g, 42.7 mmol) 17.6 g (51.2 mmol) of 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 4.1 g (64 mmol) of sodium tert- butoxide, 0.19 g (0.85 mmol) of triethylamine and 0.8 mL (1.7 mmol) of 50% tri-tert-butylphosphine are dissolved in 200 mL of xylene and stirred under reflux for 3 hours. After completion of the reaction, dichloromethane was added to dissolve it, and the mixture was washed with purified water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized from dichloromethane and methanol to give 13.4 g (58%) of the desired compound [117] as a pale yellow solid.

Synthesis of Compound [137]

[Reaction Scheme 3]

Preparation of Intermediate 6-bromo-1- (phenylsulfonyl) -lH-pyrrolo [3,2-b] pyridine Compound [137-1]

To 100 mL of tetrahydrofuran was added 16.3 g (60% in mineral oil) (406 mmol) of sodium hydride and the mixture was stirred under a nitrogen stream. The reaction is cooled to 0 < 0 > C. 50 g (254 mmol) of 5-bromo-lH-pyrrolo [3,2-b] pyridine are dissolved in 200 mL of tetrahydrofuran, and then slowly added dropwise to the reaction mixture. After the dropwise addition is complete, the reaction is stirred at 0 < 0 > C for one hour. 53.8 g (305 mmol) of benzenesulfonyl chloride was added dropwise to the reaction mixture at the same temperature, and the mixture was stirred at room temperature for 4 hours. Saturated ammonium chloride is added to the reaction and extracted with ethyl acetate. The extracted organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by column chromatography (ethyl acetate / hexane = 1/4) to obtain the target compound intermediate 6-bromo-1- (phenylsulfonyl) -lH- pyrrolo [3,2- b] 137-1] (62%).

Preparation of Intermediate 6-phenoxy-l- (phenylsulfonyl) -lH-pyrrolo [3,2-b] pyridine

A mixture of 50 g (148.3 mmol) of the intermediate 6-bromo-l- (phenylsulfonyl) -lH-pyrrolo [3,2-b] pyridine [137-1], 16 mL (178 mmol) (74.1 mmol) of copper (I) and 32 g (222.4 mmol) of copper (I) were placed in a reaction vessel and stirred under reflux for 1 hour. The reaction was cooled in a stream of nitrogen and 2.2 mL (25.2 mmol) of phenol was further added thereto, followed by reflux stirring for 2 hours. Cool the reaction mixture to room temperature, add 500 mL of dichloromethane and stir to remove the solid by filtration. The organic layer is washed with 1 M NaOH solution (100 mL X 5), dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by column chromatography (ethyl acetate / hexane = 1/5) to obtain 37.4 g of 6-phenoxy-1- (phenylsulfonyl) -lH- pyrrolo [3,2- b] (72%).

Preparation of Intermediate 1- (phenylsulfonyl) -1H-benzofuro [3,2-b] pyrrolo [2,3-e]

 35 g (100 mmol) of the intermediate 6-phenoxy-l- (phenylsulfonyl) -lH-pyrrolo [3,2- b] pyridine and 26 g (116 mmol) of palladium acetate were dissolved in 99% trifluoroacetic acid 240 mL (3.1 mol), and the mixture was stirred under reflux for 1 hour. After cooling the reaction mixture to room temperature, 1000 mL of diethyl ether is added and stirred, and the resulting solid is filtered off. Concentrate the organic layer and add 300 mL of hexane to the concentrate and concentrate again under reduced pressure to remove the acid residue. The concentrate was purified by column chromatography (ethyl acetate / hexane = 1/5) to obtain the desired compound 1- (phenylsulfonyl) -1H-benzofuro [3,2- b] pyrrolo [2,3- e] pyridine (6.6 g, 19%).

Preparation of Intermediate 1H-benzofuro [3,2-b] pyrrolo [2,3-e] pyridine [137-2]

6 g (17.2 mmol) of Intermediate 1- (phenylsulfonyl) -1H-benzofuro [3,2-b] pyrrolo [2,3- e] pyridine was dissolved in 50 mL of tetrahydrofuran, tetrabutylammonium fluoride 51.7 mL (1.0 M in tetrahydrofuran solution, 51.7 mmol) is slowly added to the reaction. The reaction is stirred at ambient temperature for 3 hours. Water is added to the reaction mixture, and the mixture is stirred. The mixture is extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was purified by column chromatography (ethyl acetate / hexane = 1/5) to obtain the desired compound intermediate 1H-benzofuro [3,2- b] pyrrolo [2,3- e] ] Of 2.7 g (74%).

Preparation of compound [137]

The intermediate compound [1-1] 2- (3-tert-Butoxycarbonylamino) pyridine hydrochloride 19.8 g (57.6 mmol) of sodium methoxide, 6.9 g (72 mmol) of sodium tert-butoxide, 0.22 g (1.0 mmol) of palladium acetate and 50 0.93 mL (1.9 mmol) of tri-tert-butylphosphine is dissolved in 200 mL of xylene and the mixture is refluxed with stirring for 3 hours. After completion of the reaction, dichloromethane was added to dissolve it, and the mixture was washed with purified water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized from dichloromethane and methanol to yield 14.9 g (60%) of the desired compound [137] as a pale yellow solid.

Synthesis of compound [146]

[Reaction Scheme 4]

The intermediate compound 1- (2- (1- Phenyl -1H- Pyrrolo [3,2-b] pyridine -5- Amino ) Phenyl ) Ethanone  Manufacturing

(183.1 mmol) of 5- bromo-1-phenyl- lH-pyrrolo [3,2-b] pyridine, 28.5 mL (234.3 mmol) of 1- g (91.5 mmol) of potassium carbonate and 50.6 g (366.1 mmol) of potassium carbonate are dissolved in 500 mL of diphenyl ether and stirred overnight at 180 ° C. After completion of the reaction, the reaction solution is cooled to room temperature, and the organic layer is separated from ethyl acetate and saturated brine. The organic layer was collected, dried, filtered and concentrated under reduced pressure. The concentrate was crystallized using dichloromethane and hexane to obtain 34.2 g (57%) of intermediate compound 1- (2- (1-phenyl-1H-pyrrolo [3,2- b] pyridin- ).

Preparation of Intermediate 2- (2- (l-phenyl-lH-pyrrolo [3,2-b] pyridin-

30 g (91.6 mmol) of intermediate 1- (2- (l-phenyl-lH-pyrrolo [3,2- b] pyridin-5-ylamino) phenyl) ethanone was dissolved in 300 mL of tetrahydrofuran under a nitrogen stream, 131 mL (183.3 mmol) of methylmagnesium bromide (1.4M in THF: toluene = 1: 3) is slowly added dropwise at room temperature. After stirring for 13 hours at room temperature, saturated ammonium chloride is added slowly to terminate the reaction and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography (dichloromethane / hexane = 1/5) to obtain the desired intermediate intermediate 2- (2- (l-phenyl- lH- pyrrolo [3,2- b] pyridin- Ylamino) phenyl) propan-2-ol was prepared in an amount of 20.1 g (64%).

Preparation of Intermediate 10,10-Dimethyl-l-phenyl-5,10-dihydro-lH-benzo [g] pyrrolo [3,2- b] [1,8] naphthyridine [146-1]

20 g (58.2 mmol) of the intermediate 2- (2- (1- (phenylsulfonyl) -lH-pyrrolo [3,2- b] pyridin-5-yl) phenyl) propan- Dissolve in 500 mL of methane and add 34 mL (524.1 mmol) of methanesulfonic acid slowly at room temperature. After completion of the dropwise addition, water is added to the reaction mixture, and the mixture is stirred for 30 minutes. The organic layer is separated, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The concentrate was purified by column chromatography (ethyl acetate / hexane = 1/10) to obtain the title compound intermediate 10,10-dimethyl-1-phenyl-5,10-dihydro-1H- benzo [g] 3,2-b] [1,8] naphthyridine [146-1] (9.9 g, 52%).

Preparation of compound [146]

Benzo [g] pyrrolo [3,2-b] [1,8] naphthyridine [146-1] 9.7 12.3 g (35.8 mmol) of intermediate compound [1-1] 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine, 4.3 g of sodium tert-butoxide 0.13 g (0.6 mmol) of palladium acetate and 0.58 mL (1.2 mmol) of 50% tri-tert-butylphosphine are dissolved in 200 mL of xylene and stirred under reflux for 3 hours. After completion of the reaction, dichloromethane was added to dissolve it, and the mixture was washed with purified water, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The concentrate was crystallized from dichloromethane and methanol to give 12.1 g (64%) of the desired compound [146] as a pale yellow solid.

Compounds 1 to 179 were prepared according to the methods of Schemes 1 to 4 above, and the results are shown below in the second set of groups.

[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. Preparation of Comparative Sample 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) / Alq3 (30 nm) / LiF (0.5 nm) / compound (30 nm) / compound a + nm) / Al (60 nm).

An 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 each for 15 minutes in acetone isopropyl alcohol and pure water, and then UV ozone cleaning for 30 minutes Respectively.

2-TNATA was vacuum deposited on the top of the device plate 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 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 produce an organic light emitting device as shown in Table 2. [ This is referred to as Comparative Sample 1.

Comparative Example 2. Production of Comparative Sample 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) / Alq3 (30 nm) / LiF (0.5 nm) / compound (30 nm) / compound (30 nm) / ITO / 2-TNATA nm) / Al (60 nm).

An anode was prepared by cutting Corning's 15 Ω / cm 2 (1000 Å) ITO glass substrate into 50 mm × 50 mm × 0.7 mm size, ultrasonically cleaning each for 15 minutes in acetone, isopropyl alcohol and pure water, Respectively. 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 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 [second group (group)]. This is referred to as Comparative Sample 2.

Example  1 to 179

In Comparative Example 1, the phosphorescent host compound a was used instead of the phosphorescent host compound a in the synthesis examples. (30 nm) / [phosphorescence green host compound 1 to 179 + compound c (10%)] (30 nm) /? -NPD An organic light emitting device having a structure of Alq3 (30 nm) / LiF (0.5 nm) / Al (60 nm) was fabricated. These are referred to as Samples 1 to 179, respectively.

Evaluation Example 1: Evaluation of luminescence characteristics

1) Evaluation of luminescent characteristics of Samples 1 to 179

The emission luminance, the luminous efficiency, and the emission peak were evaluated using Keithley source meter "2400" and KONIKA MINOLTA "CS-2000" for Comparative Samples 1 and 2 and Samples 1 to 179 prepared in the above Comparative Examples and Examples, respectively , And the results are shown in the following [third group (group)]. The samples showed green emission peak values in the 511-517 nm range.

[Group 3]

Samples 1 to 179 exhibited improved luminescence characteristics as compared to Comparative Samples 1 and 2, as confirmed from the above [third group (裙)].

Evaluation Example 2: Life characteristic evaluation

1) Evaluation of life characteristics of Samples 1 to 179

For Comparative Samples 1 and 2 and Samples 1 to 179 prepared in the above Comparative Examples and Examples, the time at which the lifetime reaches 97% based on 3000 nits was measured using an LTS-1004AC life measuring device manufactured by ENC Technologies, Inc. Respectively. The results are shown below in the fourth group (group).

[Group 4]

Samples 1 to 179 exhibited improved lifespan characteristics as compared to Comparative Samples 1 and 2, as confirmed from [fourth set of group (s)] above.

Claims (10)

Is any one of the following compounds 1 to 146, compounds 151 to 156, and compounds 165 to 179:

delete delete delete delete delete delete The method according to claim 1,
Wherein the organic light emitting compound is a phosphorescent green host material, a fluorescent green host material, a hole injection layer material, or a hole transporting layer material in a material for an organic electroluminescence device. 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. 10. The method of claim 9,
Wherein the organic electroluminescent compound is contained in at least one of a phosphorescent green host material, a fluorescent green host material, a hole injection layer material, and a hole transport layer material.