KR20120047038A - Amine derivatives and organoelectroluminescent device employing the same - Google Patents

Amine derivatives and organoelectroluminescent device employing the same Download PDF

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KR20120047038A
KR20120047038A KR1020100108676A KR20100108676A KR20120047038A KR 20120047038 A KR20120047038 A KR 20120047038A KR 1020100108676 A KR1020100108676 A KR 1020100108676A KR 20100108676 A KR20100108676 A KR 20100108676A KR 20120047038 A KR20120047038 A KR 20120047038A
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제종태
김정수
고상원
김시인
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에스에프씨 주식회사
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
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Abstract

PURPOSE: Amine derivatives are provided to have excellent power efficiency and luminous efficiency, to have excellent color purity of green color, and to manufacture an organic electroluminescence with excellent efficiency and lifetime properties. CONSTITUTION: An amine derivative is in chemical formula 1. In chemical formula 1, X is a single bond or CR11R12, Y is a single bond or CR13R14, and R1-14 is selected from substituted or unsubstituted C1-10 alkyl, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted C6-50 aryl, substituted or unsubstituted C3-50 hetero aryl group, substituted or unsubstituted C1-20 alkoxy, substituted or unsubstituted C6-30 aryloxy, substituted or unsubstituted C1-20 alkylamino, substituted or unsubstituted C6-30 arylamino group, substituted or unsubstituted C1-20 alkylsilyl, substituted or unsubstituted C6-30 arylsilyl, substituted or unsubstituted C1-50 arylalkylamino group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, cyano group, halogen group, germanium group, deuterium and hydrogen.

Description

아민 유도체 및 이를 포함하는 유기전계발광소자 {Amine derivatives and organoelectroluminescent device employing the same}Amine derivatives and organoelectroluminescent device employing the same

본 발명은 아민 유도체 및 이를 포함하는 유기전계발광소자에 관한 것으로서, 더욱 구체적으로는 전력효율 및 발광효율이 우수한 아민 유도체 및 이를 도입한 유기전계발광소자에 관한 것이다.The present invention relates to an amine derivative and an organic electroluminescent device comprising the same, and more particularly, to an amine derivative having excellent power efficiency and luminous efficiency and an organic electroluminescent device introducing the same.

유기전계발광소자 (이하, 유기 EL 소자라 함)는 정공주입전극인 제 1 전극 (애노드 전극)과 전자주입전극인 제 2 전극 (캐소드 전극) 사이에 형성된 형광성 또는 인광성 유기 화합물 박막 (이하, 유기막이라고 함)에 전자 및 정공을 주입하면, 전자와 정공이 결합하여 쌍을 이룸으로써 생성된 엑시톤 (exciton)이 여기 상태로부터 기저 상태로 떨어지면서 소멸하여 발광하는 원리를 이용한 능동 발광형 표시 소자로서, 경량화가 가능하며, 부품이 간소하여 제작공정이 간단하고, 응답속도가 빠르며, 고화질의 넓은 시야각을 확보하고 있다는 등의 장점들을 갖는다. 또한, 동영상을 완벽하게 구현할 수 있고, 고색순도 구현이 가능하며, 초박형화 및 초경량화가 가능하고, 소비 전력 및 구동전압이 낮아서 휴대용 전자기기에 적합한 전기적 특성을 갖고 있다.An organic electroluminescent device (hereinafter referred to as an organic EL device) is a fluorescent or phosphorescent organic compound thin film formed between a first electrode (anode electrode) which is a hole injection electrode and a second electrode (cathode electrode) which is an electron injection electrode (hereinafter, When the electrons and holes are injected into the organic layer, the excitons generated by the combination of electrons and holes are paired to fall from the excited state to the ground state. As a result, it is possible to reduce the weight, and the components are simple, so that the manufacturing process is simple, the response speed is fast, and the wide viewing angle of high quality is secured. In addition, video can be fully realized, high color purity can be realized, ultra-thin and ultra-light, and power consumption and driving voltage are low, which makes it suitable for portable electronic devices.

미국 등록특허 US 6951693, 한국 등록특허 KR 0736619 및 KR 0788254에서 보는 바와 같이 안트라센과 결합한 질소에 두 개의 치환기를 도입하는 형태의 분자구조를 중심으로 연구가 진행되어 왔다.As shown in US 6951693, KR 0736619, and KR 0788254, research has been focused on the molecular structure of introducing two substituents into anthracene-coupled nitrogen.

상술한 바와 같이, 유기전계발광소자에 아민을 채용한 많은 연구가 이루어지고 있지만, 현재까지는 요구되는 휘도, 효율, 구동 안정성 및 수명 등의 특성을 충분히 만족시키지 못하고 있는 실정이며, 따라서 이를 해결하기 위한 다양한 기술개발이 시급한 실정이다. 특히 발광층 도판트 물질로서 새로운 아민 유도체에 대한 많은 연구가 필요한 상황이다.
As described above, many studies have been conducted in which amines have been employed in organic light emitting diodes, but until now, they have not sufficiently satisfied characteristics such as brightness, efficiency, driving stability, and lifespan. Various technological developments are urgently needed. In particular, many studies on new amine derivatives as light emitting layer dopant materials are needed.

본 발명이 이루고자 하는 첫 번째 기술적 과제는 유기전계발광소자에 사용할 경우 전력효율 및 발광효율이 우수한 아민 유도체를 제공하는 것이다.The first technical problem to be achieved by the present invention is to provide an amine derivative having excellent power efficiency and luminous efficiency when used in an organic light emitting device.

또한 본 발명이 이루고자 하는 두 번째 기술적 과제는 상기 아민 유도체를 포함하는 유기전계발광소자를 제공하는 것이다.In addition, the second technical problem to be achieved by the present invention is to provide an organic electroluminescent device comprising the amine derivative.

상기 기술적 과제를 달성하기 위해서, 본 발명은 하기 화학식 1로 표시되는 아민 유도체를 제공한다.In order to achieve the above technical problem, the present invention provides an amine derivative represented by the following formula (1).

< 화학식 1 ><Formula 1>

Figure pat00001
Figure pat00001

상기 화학식 1에서, In Chemical Formula 1,

X는 단결합 또는 CR11R12이고, X is a single bond or CR 11 R 12 ,

Y는 단결합 또는 CR13R14이며, Y is a single bond or CR 13 R 14 ,

R1 내지 R14는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로 아릴기, 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 탄소수 1 내지 50의 아릴알킬아미노기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 시아노기, 할로겐기, 게르마늄기, 중소수 및 수소로 이루어진 군으로부터 선택되고, R 1 to R 14 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero atom having 3 to 50 carbon atoms Aryl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms 6 Arylamino group of 30 to 30, substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino group having 1 to 50 carbon atoms, substituted or Unsubstituted alkenyl, substituted or unsubstituted alkynyl, cyano, halogen, germanium, small to medium and hydrogen;

R1 내지 R14는 인접한 치환체와 탄소수 3 내지 60의 알킬렌, 탄소수 3 내지 60의 알케닐렌으로 연결되어 포화 또는 불포화 알킬 고리 또는 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, R 1 To R 14 may be connected to an adjacent substituent and alkylene having 3 to 60 carbon atoms, alkenylene having 3 to 60 carbon atoms to form a saturated or unsaturated alkyl ring or a monocyclic or polycyclic aromatic ring,

A는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이고, A is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

l은 1 내지 6의 정수이며, m은 1 내지 4의 정수이고, n은 1 내지 6의 정수이며, 이때, l, m, n이 2 이상인 경우 R1 내지 R14는 각각 같거나 다를 수 있다.l is an integer of 1 to 6, m is an integer of 1 to 4, n is an integer of 1 to 6, wherein when l, m, n is 2 or more, R 1 to R 14 may be the same or different. .

본 발명은 두 번째 기술적 과제를 해결하기 위하여, 애노드; 캐소드; 및 상기 애노드와 캐소드 사이에 상기 화학식 1에 따른 아민 유도체를 포함하는 층을 구비한 유기전계발광소자를 제공한다.
The present invention, in order to solve the second technical problem, an anode; Cathode; And it provides an organic electroluminescent device having a layer comprising an amine derivative according to the formula (1) between the anode and the cathode.

상기에서 살펴본 바와 같이, 본 발명에 따른 화학식 (1)의 화합물을 유기박막층에 포함하는 유기전계발광소자는 녹색의 색순도가 우수하며, 효율 및 수명특성이 우수하기 때문에 디스플레이 및 조명 등에 유용하게 사용될 수 있다.
As described above, the organic light emitting device including the compound of formula (1) according to the present invention in the organic thin film layer has excellent green color purity, and has excellent efficiency and lifespan characteristics, and thus may be usefully used for display and lighting. have.

도 1a 내지 1e는 본 발명의 바람직한 실시예에 따른 유기전계발광소자들의 적층구조를 나타낸 단면도들이다. 1A to 1E are cross-sectional views illustrating a lamination structure of an organic light emitting display device according to a preferred embodiment of the present invention.

본 발명은 전자수송층 재료로 사용할 수 있는 하기 화학식 1로 표시되는 아민 유도체에 관한 것으로써 구동 효율 및 발광효율이 우수한 특성을 나타낸다. The present invention relates to an amine derivative represented by the following formula (1) which can be used as an electron transport layer material, and exhibits excellent driving efficiency and luminous efficiency.

< 화학식 1 ><Formula 1>

Figure pat00002
Figure pat00002

상기 화학식 1에서, In Chemical Formula 1,

X는 단결합 또는 CR11R12이고, X is a single bond or CR 11 R 12 ,

Y는 단결합 또는 CR13R14이며, Y is a single bond or CR 13 R 14 ,

R1 내지 R14는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로 아릴기, 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 탄소수 1 내지 50의 아릴알킬아미노기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 시아노기, 할로겐기, 게르마늄기, 중소수 및 수소로 이루어진 군으로부터 선택되고, R 1 R 14 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero aryl group having 3 to 50 carbon atoms , Substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms 6 to 30 Arylamino group, substituted or unsubstituted C1-C20 alkylsilyl group, substituted or unsubstituted C6-C30 arylsilyl group, substituted or unsubstituted C1-C50 arylalkylamino group, substituted or unsubstituted Alkenyl group, substituted or unsubstituted alkynyl group, cyano group, halogen group, germanium group, small and medium numbers and hydrogen,

R1 내지 R14는 인접한 치환체와 탄소수 3 내지 60의 알킬렌, 탄소수 3 내지 60의 알케닐렌으로 연결되어 포화 또는 불포화 알킬 고리 또는 단일환 또는 다환의 방향족 고리를 형성할 수 있으며, R 1 To R 14 may be connected to an adjacent substituent and alkylene having 3 to 60 carbon atoms, alkenylene having 3 to 60 carbon atoms to form a saturated or unsaturated alkyl ring or a monocyclic or polycyclic aromatic ring,

A는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이고, A is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,

l은 1 내지 6의 정수이며, m은 1 내지 4의 정수이고, n은 1 내지 6의 정수이며, 이때, l, m, n이 2 이상인 경우 R1 내지 R14 는 각각 같거나 다를 수 있다.l is an integer of 1 to 6, m is an integer of 1 to 4, n is an integer of 1 to 6, wherein when l, m, n is 2 or more, R 1 to R 14 may be the same or different. .

본 발명의 일실시예에 따르면, 상기 X, Y, A, R1 내지 R14는 수소, 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, 탄소수 1 - 40의 알킬기, 탄소수 1 - 40의 알콕시기, 탄소수 1 - 40의 알케닐, 탄소수 1 - 40의 알키닐기, 탄소수 1 - 40의 알킬아미노기, 탄소수 6 - 40의 아릴아미노기, 탄소수 3 - 40의 헤테로아릴아미노기, 탄소수 1 - 40의 알킬실릴기, 탄소수 6 - 40의 아릴실릴기, 탄소수 6 - 40의 아릴기, 탄소수 3 - 40의 아릴옥시기, 탄소수 3 - 40의 헤테로아릴기, 게르마늄기, 인, 보론으로 이루어진 군으로부터 선택된 하나 이상의 치환기에 의해서 치환될 수 있다. According to an embodiment of the present invention, the X, Y, A, R 1 R 14 is hydrogen, deuterium, cyano group, halogen group, hydroxy group, nitro group, alkyl group of 1 to 40 carbon atoms, alkoxy group of 1 to 40 carbon atoms, alkenyl of 1 to 40 carbon atoms, alkynyl group of 1 to 40 carbon atoms, An alkylamino group having 1 to 40 carbon atoms, an arylamino group having 6 to 40 carbon atoms, a heteroarylamino group having 3 to 40 carbon atoms, an alkylsilyl group having 1 to 40 carbon atoms, an arylsilyl group having 6 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms It may be substituted by one or more substituents selected from the group consisting of, an aryloxy group having 3 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron.

본 발명의 다른 일실시예에 의하면, 상기 화학식 1에서 A는 치환 또는 비치환된 안트라센, 치환 또는 비치환된 파이렌, 치환 또는 비치환된 트리페닐렌, 치환 또는 비치환된 플루오란텐, 치환 또는 비치환된 스피로화합물로 이루어진 군 중에서 선택되는 것이 바람직하며, 구체적은 예시로는 하기 화학식들을 들 수 있다. According to another embodiment of the present invention, A in Formula 1 is substituted or unsubstituted anthracene, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthene, substituted Or it is preferably selected from the group consisting of an unsubstituted spiro compound, specific examples thereof include the following formula.

Figure pat00003

Figure pat00003

본 발명에 따른 아민 유도체의 구체적인 예시로는 하기 화학식 2 내지 화학식 231로 표시되는 군으로부터 선택된 어느 하나의 화합물을 들 수 있으나, 본 발명이 이에 제한되는 것은 아니다.
Specific examples of the amine derivative according to the present invention may include any one compound selected from the group represented by the following Chemical Formulas 2 to 231, but the present invention is not limited thereto.

Figure pat00004
Figure pat00005
Figure pat00004
Figure pat00005

[화학식 2] [화학식 3][Formula 2] [Formula 3]

Figure pat00006
Figure pat00007
Figure pat00006
Figure pat00007

[화학식 4] [화학식 5][Formula 4] [Formula 5]

Figure pat00008
Figure pat00009
Figure pat00008
Figure pat00009

[화학식 6] [화학식 7][Formula 6] [Formula 7]

Figure pat00010
Figure pat00011
Figure pat00010
Figure pat00011

[화학식 8] [화학식 9][Formula 8] [Formula 9]

Figure pat00012
Figure pat00013
Figure pat00012
Figure pat00013

[화학식 10] [화학식 11][Formula 10] [Formula 11]

Figure pat00014
Figure pat00015
Figure pat00014
Figure pat00015

[화학식 12] [화학식 13][Formula 12] [Formula 13]

Figure pat00016
Figure pat00017
Figure pat00016
Figure pat00017

[화학식 14] [화학식 15][Formula 14] [Formula 15]

Figure pat00018
Figure pat00019
Figure pat00018
Figure pat00019

[화학식 16] [화학식 17][Formula 16] [Formula 17]

Figure pat00020
Figure pat00021
Figure pat00020
Figure pat00021

[화학식 18] [화학식 19][Formula 18] [Formula 19]

Figure pat00022
Figure pat00023
Figure pat00022
Figure pat00023

[화학식 20] [화학식 21][Formula 20] [Formula 21]

Figure pat00024
Figure pat00025
Figure pat00024
Figure pat00025

[화학식 22] [화학식 23][Formula 22] [Formula 23]

Figure pat00026
Figure pat00027
Figure pat00026
Figure pat00027

[화학식 24] [화학식 25][Formula 24] [Formula 25]

Figure pat00028
Figure pat00029
Figure pat00028
Figure pat00029

[화학식 26] [화학식 27][Formula 26] [Formula 27]

Figure pat00030
Figure pat00031
Figure pat00030
Figure pat00031

[화학식 28] [화학식 29][Formula 28] [Formula 29]

Figure pat00032
Figure pat00033
Figure pat00032
Figure pat00033

[화학식 30] [화학식 31][Formula 30] [Formula 31]

Figure pat00034
Figure pat00035
Figure pat00034
Figure pat00035

[화학식 32] [화학식 33][Formula 32] [Formula 33]

Figure pat00036
Figure pat00037
Figure pat00036
Figure pat00037

[화학식 34] [화학식 35][Formula 34] [Formula 35]

Figure pat00038
Figure pat00039
Figure pat00038
Figure pat00039

[화학식 36] [화학식 37][Formula 36] [Formula 37]

Figure pat00040
Figure pat00041
Figure pat00040
Figure pat00041

[화학식 38] [화학식 39][Formula 38] [Formula 39]

Figure pat00042
Figure pat00043
Figure pat00042
Figure pat00043

[화학식 40] [화학식 41][Formula 40] [Formula 41]

Figure pat00044
Figure pat00045
Figure pat00044
Figure pat00045

[화학식 42] [화학식 43][Formula 42] [Formula 43]

Figure pat00046
Figure pat00047
Figure pat00046
Figure pat00047

[화학식 44] [화학식 45][Formula 44] [Formula 45]

Figure pat00048
Figure pat00049
Figure pat00048
Figure pat00049

[화학식 46] [화학식 47][Formula 46] [Formula 47]

Figure pat00050
Figure pat00051
Figure pat00050
Figure pat00051

[화학식 48] [화학식 49][Formula 48] [Formula 49]

Figure pat00052
Figure pat00053
Figure pat00052
Figure pat00053

[화학식 50] [화학식 51][Formula 50] [Formula 51]

Figure pat00054
Figure pat00055
Figure pat00054
Figure pat00055

[화학식 52] [화학식 53][Formula 52] [Formula 53]

Figure pat00056
Figure pat00057
Figure pat00056
Figure pat00057

[화학식 54] [화학식 55][Formula 54] [Formula 55]

Figure pat00058
Figure pat00059
Figure pat00058
Figure pat00059

[화학식 56] [화학식 57][Formula 56] [Formula 57]

Figure pat00060
Figure pat00061
Figure pat00060
Figure pat00061

[화학식 58] [화학식 59][Formula 58] [Formula 59]

Figure pat00062
Figure pat00063
Figure pat00062
Figure pat00063

[화학식 60] [화학식 61][Formula 60] [Formula 61]

Figure pat00064
Figure pat00065
Figure pat00064
Figure pat00065

[화학식 62] [화학식 63][Formula 62] [Formula 63]

Figure pat00066
Figure pat00067
Figure pat00066
Figure pat00067

[화학식 64] [화학식 65][Formula 64] [Formula 65]

Figure pat00068
Figure pat00069
Figure pat00068
Figure pat00069

[화학식 66] [화학식 67][Formula 66] [Formula 67]

Figure pat00070
Figure pat00071
Figure pat00070
Figure pat00071

[화학식 68] [화학식 69][Formula 68] [Formula 69]

Figure pat00072
Figure pat00073
Figure pat00072
Figure pat00073

[화학식 70] [화학식 71][Formula 70] [Formula 71]

Figure pat00074
Figure pat00075
Figure pat00074
Figure pat00075

[화학식 72] [화학식 73][Formula 72] [Formula 73]

Figure pat00076
Figure pat00077
Figure pat00076
Figure pat00077

[화학식 74] [화학식 75][Formula 74] [Formula 75]

Figure pat00078
Figure pat00079
Figure pat00078
Figure pat00079

[화학식 76] [화학식 77][Formula 76] [Formula 77]

Figure pat00080
Figure pat00081
Figure pat00080
Figure pat00081

[화학식 78] [화학식 79][Formula 78] [Formula 79]

Figure pat00082
Figure pat00083
Figure pat00082
Figure pat00083

[화학식 80] [화학식 81][Formula 80] [Formula 81]

Figure pat00084
Figure pat00085
Figure pat00084
Figure pat00085

[화학식 82] [화학식 83][Formula 82] [Formula 83]

Figure pat00086
Figure pat00087
Figure pat00086
Figure pat00087

[화학식 84] [화학식 85][Formula 84] [Formula 85]

Figure pat00088
Figure pat00089
Figure pat00088
Figure pat00089

[화학식 86] [화학식 87][Formula 86] [Formula 87]

Figure pat00090
Figure pat00091
Figure pat00090
Figure pat00091

[화학식 88] [화학식 89][Formula 88] [Formula 89]

Figure pat00092
Figure pat00093
Figure pat00092
Figure pat00093

[화학식 90] [화학식 91][Formula 90] [Formula 91]

Figure pat00094
Figure pat00095
Figure pat00094
Figure pat00095

[화학식 92] [화학식 93][Formula 92] [Formula 93]

Figure pat00096
Figure pat00097
Figure pat00096
Figure pat00097

[화학식 94] [화학식 95][Formula 94] [Formula 95]

Figure pat00098
Figure pat00099
Figure pat00098
Figure pat00099

[화학식 96] [화학식 97][Formula 96] [Formula 97]

Figure pat00100
Figure pat00101
Figure pat00100
Figure pat00101

[화학식 98] [화학식 99][Formula 98] [Formula 99]

Figure pat00102
Figure pat00103
Figure pat00102
Figure pat00103

[화학식 100] [화학식 101][Formula 100] [Formula 101]

Figure pat00104
Figure pat00105
Figure pat00104
Figure pat00105

[화학식 102] [화학식 103][Formula 102] [Formula 103]

Figure pat00106
Figure pat00107
Figure pat00106
Figure pat00107

[화학식 104] [화학식 105][Formula 104] [Formula 105]

Figure pat00108
Figure pat00109
Figure pat00108
Figure pat00109

[화학식 106] [화학식 107][Formula 106] [Formula 107]

Figure pat00110
Figure pat00111
Figure pat00110
Figure pat00111

[화학식 108] [화학식 109]

Figure pat00112
Figure pat00113
[Formula 108] [Formula 109]
Figure pat00112
Figure pat00113

[화학식 110] [화학식 111][Formula 110] [Formula 111]

Figure pat00114
Figure pat00115
Figure pat00114
Figure pat00115

[화학식 112] [화학식 113][Formula 112] [Formula 113]

Figure pat00116
Figure pat00117
Figure pat00116
Figure pat00117

[화학식 114] [화학식 115][Formula 114] [Formula 115]

Figure pat00118
Figure pat00119
Figure pat00118
Figure pat00119

[화학식 116] [화학식 117][Formula 116] [Formula 117]

Figure pat00120
Figure pat00121
Figure pat00120
Figure pat00121

[화학식 118] [화학식 119][Formula 118] [Formula 119]

Figure pat00122
Figure pat00123
Figure pat00122
Figure pat00123

[화학식 120] [화학식 121][Formula 120] [Formula 121]

Figure pat00124
Figure pat00125
Figure pat00124
Figure pat00125

[화학식 122] [화학식 123][Formula 122] [Formula 123]

Figure pat00126
Figure pat00127
Figure pat00126
Figure pat00127

[화학식 124] [화학식 125][Formula 124] [Formula 125]

Figure pat00128
Figure pat00129
Figure pat00128
Figure pat00129

[화학식 126] [화학식 127][Formula 126] [Formula 127]

Figure pat00130
Figure pat00131
Figure pat00130
Figure pat00131

[화학식 128] [화학식 129][Formula 128] [Formula 129]

Figure pat00132
Figure pat00133
Figure pat00132
Figure pat00133

[화학식 130] [화학식 131][Formula 130] [Formula 131]

Figure pat00134
Figure pat00135
Figure pat00134
Figure pat00135

[화학식 132] [화학식 133][Formula 132] [Formula 133]

Figure pat00136
Figure pat00137
Figure pat00136
Figure pat00137

[화학식 134] [화학식 135][Formula 134] [Formula 135]

Figure pat00138
Figure pat00139
Figure pat00138
Figure pat00139

[화학식 136] [화학식 137][Formula 136] [Formula 137]

Figure pat00140
Figure pat00141
Figure pat00140
Figure pat00141

[화학식 138] [화학식 139][Formula 138] [Formula 139]

Figure pat00142
Figure pat00143
Figure pat00142
Figure pat00143

[화학식 140] [화학식 141][Formula 140] [Formula 141]

Figure pat00144
Figure pat00145
Figure pat00144
Figure pat00145

[화학식 142] [화학식 143][Formula 142] [Formula 143]

Figure pat00146
Figure pat00147
Figure pat00146
Figure pat00147

[화학식 144] [화학식 145][Formula 144] [Formula 145]

Figure pat00148
Figure pat00149
Figure pat00148
Figure pat00149

[화학식 146] [화학식 147][Formula 146] [Formula 147]

Figure pat00150
Figure pat00151
Figure pat00150
Figure pat00151

[화학식 148] [화학식 149][Formula 148] [Formula 149]

Figure pat00152
Figure pat00153
Figure pat00152
Figure pat00153

[화학식 150] [화학식 151][Formula 150] [Formula 151]

Figure pat00154
Figure pat00155
Figure pat00154
Figure pat00155

[화학식 152] [화학식 153][Formula 152] [Formula 153]

Figure pat00156
Figure pat00157
Figure pat00156
Figure pat00157

[화학식 154] [화학식 155][Formula 154] [Formula 155]

Figure pat00158
Figure pat00159
Figure pat00158
Figure pat00159

[화학식 156] [화학식 157][Formula 156] [Formula 157]

Figure pat00160
Figure pat00161
Figure pat00160
Figure pat00161

[화학식 158] [화학식 159][Formula 158] [Formula 159]

Figure pat00162
Figure pat00163
Figure pat00162
Figure pat00163

[화학식 160] [화학식 161][Formula 160] [Formula 161]

Figure pat00164
Figure pat00165
Figure pat00164
Figure pat00165

[화학식 162] [화학식 163][Formula 162] [Formula 163]

Figure pat00166
Figure pat00167
Figure pat00166
Figure pat00167

[화학식 164] [화학식 165][Formula 164] [Formula 165]

Figure pat00168
Figure pat00169
Figure pat00168
Figure pat00169

[화학식 166] [화학식 167][Formula 166] [Formula 167]

Figure pat00170
Figure pat00171
Figure pat00170
Figure pat00171

[화학식 168] [화학식 169][Formula 168] [Formula 169]

Figure pat00172
Figure pat00173
Figure pat00172
Figure pat00173

[화학식 170] [화학식 171][Formula 170] [Formula 171]

Figure pat00174
Figure pat00175
Figure pat00174
Figure pat00175

[화학식 172] [화학식 173][Formula 172] [Formula 173]

Figure pat00176
Figure pat00177
Figure pat00176
Figure pat00177

[화학식 174] [화학식 175][Formula 174] [Formula 175]

Figure pat00178
Figure pat00179
Figure pat00178
Figure pat00179

[화학식 176] [화학식 177][Formula 176] [Formula 177]

Figure pat00180
Figure pat00181
Figure pat00180
Figure pat00181

[화학식 178] [화학식 179][Formula 178] [Formula 179]

Figure pat00182
Figure pat00183
Figure pat00182
Figure pat00183

[화학식 180] [화학식 181][Formula 180] [Formula 181]

Figure pat00184
Figure pat00185
Figure pat00184
Figure pat00185

[화학식 182] [화학식 183][Formula 182] [Formula 183]

Figure pat00186
Figure pat00187
Figure pat00186
Figure pat00187

[화학식 184] [화학식 185][Formula 184] [Formula 185]

Figure pat00188
Figure pat00189
Figure pat00188
Figure pat00189

[화학식 186] [화학식 187][Formula 186] [Formula 187]

Figure pat00190
Figure pat00191
Figure pat00190
Figure pat00191

[화학식 188] [화학식 189][Formula 188] [Formula 189]

Figure pat00192
Figure pat00193
Figure pat00192
Figure pat00193

[화학식 190] [화학식 191][Formula 190] [Formula 191]

Figure pat00194
Figure pat00195
Figure pat00194
Figure pat00195

[화학식 192] [화학식 193][Formula 192] [Formula 193]

Figure pat00196
Figure pat00197
Figure pat00196
Figure pat00197

[화학식 194] [화학식 195][Formula 194] [Formula 195]

Figure pat00198
Figure pat00199
Figure pat00198
Figure pat00199

[화학식 196] [화학식 197][Formula 196] [Formula 197]

Figure pat00200
Figure pat00201
Figure pat00200
Figure pat00201

[화학식 198] [화학식 199][Formula 198] [Formula 199]

Figure pat00202
Figure pat00203
Figure pat00202
Figure pat00203

[화학식 200] [화학식 201][Formula 200] [Formula 201]

Figure pat00204
Figure pat00205
Figure pat00204
Figure pat00205

[화학식 202] [화학식 203][Formula 202] [Formula 203]

Figure pat00206
Figure pat00207
Figure pat00206
Figure pat00207

[화학식 204] [화학식 205][Formula 204] [Formula 205]

Figure pat00208
Figure pat00209
Figure pat00208
Figure pat00209

[화학식 206] [화학식 207][Formula 206] [Formula 207]

Figure pat00210
Figure pat00211
Figure pat00210
Figure pat00211

[화학식 208] [화학식 209][Formula 208] [Formula 209]

Figure pat00212
Figure pat00213
Figure pat00212
Figure pat00213

[화학식 210] [화학식 211][Formula 210] [Formula 211]

Figure pat00214
Figure pat00215
Figure pat00214
Figure pat00215

[화학식 212] [화학식 213][Formula 212] [Formula 213]

Figure pat00216
Figure pat00217
Figure pat00216
Figure pat00217

[화학식 214] [화학식 215][Formula 214] [Formula 215]

Figure pat00218
Figure pat00219
Figure pat00218
Figure pat00219

[화학식 216] [화학식 217][Formula 216] [Formula 217]

Figure pat00220
Figure pat00221
Figure pat00220
Figure pat00221

[화학식 218] [화학식 219][Formula 218] [Formula 219]

Figure pat00222
Figure pat00223
Figure pat00222
Figure pat00223

[화학식 220] [화학식 221][Formula 220] [Formula 221]

Figure pat00224
Figure pat00225
Figure pat00224
Figure pat00225

[화학식 222] [화학식 223][Formula 222] [Formula 223]

Figure pat00226
Figure pat00227
Figure pat00226
Figure pat00227

[화학식 224] [화학식 225][Formula 224] [Formula 225]

Figure pat00228
Figure pat00229
Figure pat00228
Figure pat00229

[화학식 226] [화학식 227][Formula 226] [Formula 227]

Figure pat00230
Figure pat00231
Figure pat00230
Figure pat00231

[화학식 228] [화학식 229][Formula 228] [Formula 229]

Figure pat00232
Figure pat00233
Figure pat00232
Figure pat00233

[화학식 230] [화학식 231]
[Formula 230] [Formula 231]

본 발명에서 사용되는 치환기인 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, tert-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있고, 상기 알킬기 중 하나 이상의 수소 원자는 할로겐 원자, 히드록시기, 니트로기, 시아노기, 실릴기(이 경우 "알킬실릴기"라 함), 치환 또는 비치환된 아미노기(-NH2, -NH(R), -N(R')(R''), R'과 R"은 서로 독립적으로 탄소수 1 내지 10의 알킬기이며, 이 경우 "알킬아미노기"라 함), 아미디노기, 히드라진기, 히드라존기, 카르복실기, 술폰산기, 인산기, 탄소수 1 내지 20의 알킬기, 탄소수 1 내지 20의 할로겐화된 알킬기, 탄소수 1 내지 20의 알케닐기, 탄소수 1 내지 20의 알키닐기, 탄소수 1 내지 20의 헤테로알킬기, 탄소수 6 내지 20의 아릴기, 탄소수 6 내지 20의 아릴알킬기, 탄소수 6 내지 20의 헤테로아릴기 또는 탄소수 6 내지 20의 헤테로아릴알킬기로 치환될 수 있다.Specific examples of the alkyl group which is a substituent used in the present invention include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, iso-amyl, hexyl, and the like. Halogen atom, hydroxy group, nitro group, cyano group, silyl group (in this case referred to as "alkylsilyl group"), substituted or unsubstituted amino group (-NH 2 , -NH (R), -N (R ') (R ''), R 'and R "are independently of each other an alkyl group having 1 to 10 carbon atoms, in this case," alkylamino group "), amidino group, hydrazine group, hydrazone group, carboxyl group, sulfonic acid group, phosphoric acid group, 1 carbon atom An alkyl group of 20 to 20 carbon atoms, a halogenated alkyl group of 1 to 20 carbon atoms, an alkenyl group of 1 to 20 carbon atoms, an alkynyl group of 1 to 20 carbon atoms, a heteroalkyl group of 1 to 20 carbon atoms, an aryl group of 6 to 20 carbon atoms, and 6 to 20 carbon atoms Arylalkyl group, a heteroaryl group of 6 to 20 carbon atoms or 6 to It may be substituted with 20 heteroarylalkyl groups.

본 발명의 화합물에서 사용되는 치환기인 알콕시기의 구체적인 예로는 메톡시, 에톡시, 프로폭시, 이소부틸옥시, sec-부틸옥시, 펜틸옥시, iso-아밀옥시, 헥실옥시 등을 들 수 있고, 상기 알콕시기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.Specific examples of the alkoxy group which is a substituent used in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like. At least one hydrogen atom of the alkoxy group may be substituted with the same substituent as in the alkyl group.

상기 본 발명의 화합물에서 사용되는 치환기인 아릴기는 하나 이상의 고리를 포함하는 카보시클릭 방향족 시스템을 의미하며, 상기 고리들은 펜던트 방법으로 함께 부착되거나 또는 융합(fused)될 수 있다. 아릴기의 구체적인 예로는 페닐, 나프틸, 테트라히드로나프틸, 플루오란테닐, 피렌닐, 안트라센닐, 펜안트레닐 등과 같은 방향족 그룹을 들 수 있고, 상기 아릴기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다 (예를 들어, 아미노기로 치환되는 경우는 "아릴아미노기", 실릴기로 치환되는 경우는 "아릴실릴기", 옥시기로 치환되는 경우는 "아릴옥시기"라 함).An aryl group, which is a substituent used in the compound of the present invention, means a carbocyclic aromatic system including one or more rings, and the rings may be attached or fused together by a pendant method. Specific examples of the aryl group may include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl, fluoranthenyl, pyrenyl, anthracenyl, phenanthrenyl, and the like, and at least one hydrogen atom of the aryl group may be Substituted with the same substituent as in the case (for example, when substituted with an amino group is an "arylamino group", when substituted with a silyl group is "arylsilyl group", when substituted with an oxy group is called "aryloxy group"). ).

본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기는 N, O, P, Si 또는 S 중에서 선택된 1, 2 또는 3개의 헤테로 원자를 포함하고, 나머지 고리 원자가 탄소인 탄소수 3 내지 50의 고리 방향족 시스템을 의미하며, 상기 고리들은 펜던트 방법으로 함께 부착되거나 또는 융합(fused)될 수 있다. 그리고 상기 헤테로아릴기 중 하나 이상의 수소 원자는 상기 알킬기의 경우와 마찬가지의 치환기로 치환가능하다.The heteroaryl group which is a substituent used in the compound of the present invention means a ring aromatic system having 3 to 50 carbon atoms containing 1, 2 or 3 hetero atoms selected from N, O, P, Si or S, and the remaining ring atoms are carbon. The rings may be attached or fused together in a pendant manner. At least one hydrogen atom of the heteroaryl group may be substituted with the same substituent as in the alkyl group.

본 발명에 따른 유기전계발광소자는 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 상기 화학식 (1)로 표시되는 아민 유도체를 함유한 층을 포함하는 것이 특징이다. An organic light emitting display device according to the present invention includes an anode; Cathode; And a layer containing an amine derivative represented by the formula (1) between the anode and the cathode.

구체적으로 본 발명에 따른 유기전계발광소자는 상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 포함할 수도 있는데, 상기 정공주입층, 정공수송층, 전자수송층 및 전자주입층은 정공 또는 전자들을 발광 고분자로 효율적으로 전달시켜 줌으로써 발광 고분자 내에서 발광 결합의 확률을 높이는 역할을 한다.Specifically, the organic light emitting device according to the present invention may include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer between the anode and the cathode, the hole injection layer The hole transport layer, the electron transport layer, and the electron injection layer serve to increase the probability of light emitting coupling in the light emitting polymer by efficiently transferring holes or electrons to the light emitting polymer.

본 발명에 따른 아민 유도체는 애노드 및 캐소드 사이의 전자수송층 중에 포함되는 것이 바람직하다. 또한 본 발명의 일실시예에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자 등에 사용될 수 있다. The amine derivative according to the present invention is preferably included in the electron transport layer between the anode and the cathode. In addition, the organic light emitting display device according to an embodiment of the present invention can be used for a display device, a display device and a monochrome or white lighting device.

정공주입층 및 정공수송층은 애노드로부터 정공이 주입되고, 주입된 정공이 수송되는 것을 용이하게 하기 위해서 적층되는 것으로서, 이러한 정공수송층용 물질로는 이온화 포텐셜이 작은 전자공여성 분자들이 사용되는데, 주로 트리페닐아민을 기본골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다. The hole injection layer and the hole transport layer are laminated to facilitate the injection of holes from the anode and the transport of the injected holes. As the material for the hole transport layer, electron donor molecules having small ionization potential are used. Diamine, triamine or tetraamine derivatives based on amines are frequently used.

본 발명에서도, 상기 정공수송층의 재료로서, 당업계에 통상적으로 사용되는 것인 한, 다양한 물질을 제한 없이 사용할 수 있으며, 예를 들어, N, N'-비스(3-메틸페닐)-N, N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD) 또는 N, N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(α-NPD) 등을 사용할 수 있다. 또한, 상기 정공수송층의 하부에는 정공주입층 (HIL: Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있다. 예를 들어 하기 화학식 2 내지 화학식 4에 열거된 CuPc 또는 스타버스트(Starburst)형 아민류인 TCTA, m-MTDATA, IDE406 (이데미쯔사 재료) 등을 사용할 수 있다.In the present invention, as the material of the hole transport layer, as long as it is commonly used in the art, various materials can be used without limitation, for example, N, N ' -bis (3-methylphenyl) -N, N ' -Diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD) or N, N' -di (naphthalen-1-yl) -N, N' -diphenyl benzidine (α-NPD ) Can be used. In addition, a hole injection layer (HIL) may be further stacked below the hole transport layer, and the hole injection layer material may be used without particular limitation as long as it is commonly used in the art. For example, CuPc or Starburst type amines, such as TCTA, m-MTDATA, IDE406 (manufactured by Idemitsu Corp.) and the like listed in the following Chemical Formulas 2 to 4 may be used.

Figure pat00234
Figure pat00235
Figure pat00236
Figure pat00234
Figure pat00235
Figure pat00236

CuPC TCTA m-MTDATA         CuPC TCTA m-MTDATA

한편, 상기 전자수송층은 캐소드로부터 공급된 전자를 발광층으로 원활히 수송하고 상기 발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다. 이러한 전자수송층 재료로는 통상 8-히드록시퀴놀린 알루미늄 (Alq3), PBD(2-(4-바이페닐)-5-(4-t-부틸페닐)-1,3,4-옥사디아졸), TNF(2,4,7-트리니트로플로오렌), BMD, BND 등이 사용되고 있는데, 본 발명에서는 상기 [화학식 1]의 아민 유도체를 사용하여 전력효율 및 발광효율을 향상시켰다.On the other hand, the electron transport layer serves to increase the chance of recombination in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the light emitting layer and suppressing the movement of holes that are not bonded in the light emitting layer. Such electron transport layer materials typically include 8-hydroxyquinoline aluminum (Alq 3), PBD (2- (4-biphenyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole), TNF (2,4,7-trinitrofluoroene), BMD, BND and the like are used, in the present invention by using the amine derivative of the formula [1] to improve the power efficiency and luminous efficiency.

한편, 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선시키는 기능을 수행하는 전자주입층 (EIL: Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당업계에서 통상적으로 사용되는 것이면 특별한 제한 없이 사용될 수 있으며, 예를 들어, LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.Meanwhile, an electron injection layer (EIL) may be further stacked on the upper portion of the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, it may be used a material such as LiF, NaCl, CsF, Li 2 O, BaO.

더 나아가, 본 발명에 따른 유기전계발광소자는 상기 언급한 정공주입층, 정공수송층, 전자수송층 및 전자주입층 이외에도, 정공저지층 또는 전자저지층 등과 같은 부가적 기능성 적층 구조들을 더 포함할 수도 있다. 이때, 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 정공저지층을 이루는 물질은 특별히 제한되지는 않으나, 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며, 대표적으로 BAlq, BCP, TPBI 등을 사용할 수 있다. Furthermore, in addition to the above-described hole injection layer, hole transport layer, electron transport layer, and electron injection layer, the organic light emitting device according to the present invention may further include additional functional laminated structures such as a hole blocking layer or an electron blocking layer. . At this time, the hole blocking layer serves to prevent such a problem by using a material having a very low HOMO level because the life and efficiency of the device is reduced when holes are introduced into the cathode through the organic light emitting layer. The material constituting the hole blocking layer is not particularly limited, but must have an ionization potential higher than that of the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

보다 구체적으로, 하기 도 1a 내지 도 1e에는 다양한 형태의 적층 구조를 갖는 유기전계발광소자들을 도시하였으며, 이를 참조하면, 도 1a의 유기전계발광소자는 애노드/정공주입층/발광층/캐소드로 이루어진 구조를 갖고, 도 1b의 유기전계발광소자는 애노드/정공주입층/발광층/전자주입층/캐소드로 이루어진 구조를 갖는다. 또한, 도 1c의 유기전계발광소자는 애노드/정공주입층/정공수송층/발광층/캐소드의 구조를 갖고, 도 1d에 도시된 유기전계발광소자는 애노드/정공주입층/정공수송층/발광층/전자주입층/캐소드의 구조를 갖는다. 마지막으로, 도 1e의 유기전계발광소자는 애노드/정공주입층/정공수송층/발광층/전자수송층/전자주입층/캐소드의 구조를 갖는다.More specifically, FIGS. 1A to 1E illustrate organic light emitting diodes having various types of stacked structures. Referring to this, the organic light emitting diode of FIG. 1A includes an anode / hole injection layer / light emitting layer / cathode. The organic electroluminescent device of FIG. 1B has a structure consisting of an anode / hole injection layer / light emitting layer / electron injection layer / cathode. In addition, the organic light emitting display device of FIG. 1c has a structure of an anode / hole injection layer / hole transporting layer / light emitting layer / cathode, and the organic light emitting device shown in FIG. 1d includes an anode / hole injection layer / hole transporting layer / light emitting layer / electron injection Has a structure of layers / cathodes. Finally, the organic light emitting display device of FIG. 1E has a structure of an anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode.

한편, 본 발명에 따른 유기전계발광소자는 상기 아민 유도체를, 애노드 및 캐소드 사이에 개재되는 다양한 적층 구조 내에 포함할 수 있지만, 애노드 및 캐소드 사이의 전자수송층 중에 포함되는 것이 바람직하다.On the other hand, the organic electroluminescent device according to the present invention may include the amine derivative in a variety of laminated structures interposed between the anode and the cathode, it is preferably included in the electron transport layer between the anode and the cathode.

이하, 본 발명에 따른 유기전계발광소자를 제조하는 방법에 관하여 도 1a 내지 1e를 참조하여 설명한다. Hereinafter, a method of manufacturing an organic light emitting display device according to the present invention will be described with reference to FIGS. 1A to 1E.

먼저, 기판 상부에 애노드용 물질을 코팅한다. 기판으로는 통상적인 발광 소자에서 사용되는 기판을 사용하는데, 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유리기판 또는 투명 플라스틱 기판이 바람직하다. 또한, 애노드 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2) 또는 산화아연(ZnO) 등의 당업계에서 통상적으로 사용되고 있는 물질들이 사용될 수 있다. 상기 애노드 상부로는 정공주입층이 진공 열증착 또는 스핀코팅 등의 방법에 의해서 선택적으로 적층되며, 그 다음으로 상기 정공주입층 상부에 정공수송층을 진공 열증착 또는 스핀코팅 등의 방법에 의해서 형성된다.First, an anode material is coated on the substrate. As the substrate, a substrate used in a conventional light emitting device is used. A glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is preferable. In addition, as the anode material, materials commonly used in the art, such as transparent and conductive indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO), may be used. have. The hole injection layer is selectively stacked on the anode by vacuum thermal deposition or spin coating, and then the hole transport layer is formed on the hole injection layer by vacuum thermal deposition or spin coating. .

다음으로는, 상기 정공수송층 상부에 발광층을 적층한 후, 그 위에 선택적으로 정공저지층을 진공 열증착 또는 스핀코팅 방법에 의해서 형성한다. 마지막으로, 이러한 정공저지층 위에 전자수송층을 진공 열증착 또는 스핀코팅 방법을 통해 증착한 후에 전자주입층을 선택적으로 형성하고, 상기 전자주입층 상부에 캐소드 형성용 금속을 진공 열증착함으로써 본 발명에 따른 유기전계발광소자를 제조할 수 있게 된다. 한편, 캐소드 형성용 금속으로는, 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리튬(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면발광소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수도 있다.
Next, after the light emitting layer is laminated on the hole transport layer, a hole blocking layer is selectively formed thereon by vacuum thermal evaporation or spin coating. Finally, the electron transport layer is deposited on the hole blocking layer by vacuum thermal deposition or spin coating, and then an electron injection layer is selectively formed, and the cathode forming metal is vacuum-deposited on the electron injection layer. The organic electroluminescent device according to the present invention can be manufactured. On the other hand, as the cathode forming metal, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) or the like, and a transmissive cathode using ITO or IZO may be used to obtain a front light emitting device.

이하, 본 발명을 하기 실시예를 통하여 본 발명을 보다 상세하게 설명하고자 하나, 하기의 실시예는 단지 설명의 목적을 위한 것으로 본 발명을 제한하기 위한 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to the following examples, but the following examples are for illustrative purposes only and are not intended to limit the present invention.

합성예Synthetic example 1. 화학식 5의 합성 1.Synthesis of Formula 5

합성예Synthetic example 1-1. <1-b>의 합성 1-1. Synthesis of <1-b>

하기 반응식 1에 의하여 <1-b>를 합성하였다.<1-b> was synthesized according to Scheme 1 below.

[반응식 1]

Figure pat00237
[Reaction Scheme 1]
Figure pat00237

1L 둥근 바닥 플라스크에 브로모벤젠 44.3g(0.282mol), THF 250ml를 넣은 후 , 영하 78도 까지 냉각시켰다. 이어서, 노르말부틸리튬 163ml (0.2613mol)을 천천히 적가하고, 동일한 온도에서 1시간 교반 한 후, 2,6-디브로모안트라퀴논 30g (0.1045mol)을 첨가하였다. 상기 반응 결과물을 상온으로 승온 한 후, 12시간 동안 교반하였고, 반응물에 2N 염산 300ml를 첨가하였다. 결과물을 층 분리하여 유기층을 MgSO4로 건조하고, 여과 및 여액 농축 과정을 수행하여 <1-a>를 제조하였다.      44.3 g (0.282 mol) of bromobenzene and 250 ml of THF were added to a 1 L round bottom flask, and then cooled to minus 78 degrees. Subsequently, 163 ml (0.2613 mol) of normal butyllithium was slowly added dropwise, stirred for 1 hour at the same temperature, and then 30 g (0.1045 mol) of 2,6-dibromoanthraquinone was added. The reaction product was warmed to room temperature, stirred for 12 hours, and 300 ml of 2N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was dried over MgSO 4, filtered, and concentrated through a filtrate to prepare <1-a>.

1L의 둥근바닥 플라스크에 <1-a>를 넣은 후 KI 52g (0.3135mol), NaH2PO2-H2O 66.5g (0.627mol), 아세트산 600ml를 첨가하여 5시간 동안 환류 냉각시켰다. 결과물은 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정시켜서 생성된 고체를 여과한 후, 감압 건조하여 <1-b> 19g( 45%)을 제조하였다.
After putting <1-a> into a 1 L round bottom flask, 52 g (0.3135 mol) of KI, 66.5 g (0.627 mol) of NaH 2 PO 2 -H 2 O, and 600 ml of acetic acid were added and refluxed for 5 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed resultant was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give <1-b> 19 g (45%).

합성예Synthetic example 1-2. <1-c>의 합성 1-2. Synthesis of <1-c>

하기 반응식 2에 의하여 <1-c>를 합성하였다.<1-c> was synthesized by the following Scheme 2.

[반응식 2]Scheme 2

Figure pat00238
Figure pat00238

500ml의 둥근바닥 플라스크에 페닐하이드라진40g(0.3699mol), 2-메틸싸이클로헥사논 41.5g(0.3699mol), 아세트산 240ml을 넣은 후 6시간 동안 환류시킨다. 반응이 완료 된 후 반응액을 수산화나트륨으로 염기화시킨다.40 g (0.3699 mol) of phenylhydrazine, 41.5 g (0.3699 mol) of 2-methylcyclohexanone, and 240 ml of acetic acid were added to a 500 ml round bottom flask, followed by reflux for 6 hours. After the reaction is completed, the reaction solution is basified with sodium hydroxide.

물과 에틸렌아세테이트로 추출하여 중성화시킨 후 유기층을 황산 마그네슘으로 무수처리하여 감압 농축한 후 헥산과 메틸렌클로라이드를 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 <1-c>을 57.5g ( 84%) 제조하였다.
After neutralization with water and ethylene acetate, the organic layer was anhydrous with magnesium sulfate, concentrated under reduced pressure, and 57.5g (84%) of <1-c> obtained by column chromatography using hexane and methylene chloride as a developing solvent. ) Was prepared.

합성예Synthetic example 1-3. <1-d>의 합성 1-3. Synthesis of <1-d>

하기 반응식 3에 의하여 <1-d>를 합성하였다.<1-d> was synthesized according to Scheme 3 below.

[반응식 3]Scheme 3

Figure pat00239
Figure pat00239

질소분위기의 500ml 둥근바닥 플라스크 에 화학식 1로부터 얻은 <1-a> 50g(0.2699mol)를 톨루엔 150ml에 녹인 후, 영하 20도로 온로를 낮춘다. 1.6M 메틸리튬 260ml(0.1753mol)을 위 용액에 천천히 적가 한 후 영하 20도에서 3시간동안 반응시킨다. 반응이 완료된 후 반응액에 톨루엔과 물의 1:1 용액 200ml을 천천히 붓는다. 층분리하여 유기층을 황산 마그네슘으로 무수처리 하여 감압 농축한 후 헥산과 메틸렌클로라이드를 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 <1-d>을 47.3g (87%) 제조하였다.
50 g (0.2699 mol) of <1-a> obtained from Chemical Formula 1 were dissolved in 150 ml of toluene in a 500 ml round bottom flask in a nitrogen atmosphere, and the furnace was lowered to minus 20 degrees. 260 ml (0.1753 mol) of 1.6 M methyllithium are slowly added dropwise to the solution, followed by reaction at -20 ° C for 3 hours. After the reaction was completed, slowly pour 200ml of 1: 1 solution of toluene and water into the reaction solution. The layers were separated and the organic layer was treated with anhydrous magnesium sulfate, concentrated under reduced pressure, and 47.3 g (87%) of <1-d> obtained by column chromatography using hexane and methylene chloride as a developing solvent was prepared.

합성예Synthetic example 1-3. <화학식 5>의 합성 1-3. Synthesis of <Formula 5>

하기 반응식 4에 의하여 <화학식 5>를 합성하였다.<Chemical Formula 5> was synthesized by the following Scheme 4.

[반응식 4]Scheme 4

Figure pat00240
Figure pat00240

250ml 둥근 바닥 플라스크에 반응식 1에서 합성한 <1-b> 10g (0.0205mol), 반응식 3에서 합성한 <1-d> 9.9g (0.0492mol), 팔라듐아세테이트 0.18g(0.82mmol), 바이넵 0.51g(0.82mmol), 소듐 텨셔리 부톡사이드 7.8g(0.082mol), 톨루엔 80ml를 넣고 12 시간 동안 환류시킨다. 반응이 완료되면 뜨거운 상태에서 뷰흐너 깔대기에 셀라이트를 깔고 여과한다. 여액을 농축한 후, toluene으로 재결정 실시한다. 재결정 방법을 여러 번 반복하여 연노란색의 고체 <화학식 5> 6.9 g (46 %)을 얻었다.<1-b> 10 g (0.0205 mol) synthesized in Scheme 1, <1-d> 9.9 g (0.0492 mol) synthesized in Scheme 3, 0.18 g (0.82 mmol) of Palladium Acetate, 0.51 in 250 ml round bottom flask g (0.82 mmol), 7.8 g (0.082 mol) of sodium cushion butoxide, and 80 ml of toluene were added and refluxed for 12 hours. When the reaction is complete, place a celite and filter on a Buchner funnel in the hot state. The filtrate is concentrated and then recrystallized from toluene. The recrystallization method was repeated several times to obtain 6.9 g (46%) of a pale yellow solid.

MS(MALDI-TOF): m/z 728.41[M]+ MS (MALDI-TOF): m / z 728.41 [M] +

Anal.Calcd for C54H52N2 : C, 88.97; H, 7.19; N, 3.84 . Found: C, 88.96; H, 7.21; N, 3.93
Anal.Calcd for C 54 H 52 N 2 : C, 88.97; H, 7. 19; N, 3.84. Found: C, 88.96; H, 7. 21; N, 3.93

합성예Synthetic example 2. 화학식 14의 합성 2. Synthesis of Chemical Formula 14

합성예Synthetic example 2-1. <2-a>의 합성 2-1. Synthesis of <2-a>

하기 반응식 5에 의하여 <2-a>를 합성하였다.<2-a> was synthesized according to Scheme 5 below.

[반응식 5]Scheme 5

Figure pat00241
Figure pat00241

반응식 2에서 사용한 2-메틸싸이클로헥사논 대신 3,4-디메틸 싸이클로헥사논을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <2-a>를 23.5g (82%) 제조하였다.
23.5 g (82%) of <2-a> was prepared by the same method except that 3,4-dimethyl cyclohexanone was used instead of 2-methylcyclohexanone used in Scheme 2.

합성예Synthetic example 2-2. <2-b>의 합성 2-2. Synthesis of <2-b>

하기 반응식 6에 의하여 <2-b>를 합성하였다.<2-b> was synthesized according to Scheme 6 below.

[반응식 6]Scheme 6

Figure pat00242
Figure pat00242

250ml 반응기에 <2-a> 20g(0.301mol)과 아세트산 120ml을 넣고 교반시킨다. 외부온도를 영도로 낮춘 후 위의 용액에 소듐시아노보로하이드라이드(NaCNBH3) 18.9g(0.6198mol)을 5회에 나누어 천천히 투입한다. 투입완료 후 상온에서 3시간교반한다. 20 g (0.301 mol) of <2-a> and 120 ml of acetic acid are added to a 250 ml reactor and stirred. After the external temperature was lowered to zero, 18.9 g (0.6198 mol) of sodium cyanoborohydride (NaCNBH3) was slowly added to the solution. Stir at room temperature after 3 hours.

반응 완료 후 물 100ml를 넣은 후 수산화트륨을 넣어 염기화시킨다. 에틸아세테이트 와 물을 넣고 추출하여 중화시킨다. 유기층을 무수처리 하여 감압 농축한 후 헥산과 에틸아세테이트을 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 <2-b>을 16.7 g(83%) 제조하였다.
After completion of the reaction, 100ml of water was added, followed by addition of sodium hydroxide to make it basic. Add ethyl acetate and water to neutralize the extract. The organic layer was anhydrous, concentrated under reduced pressure, and then 16.7 g (83%) of <2-b> obtained by column chromatography using hexane and ethyl acetate as a developing solvent was obtained.

합성예Synthetic example 2-3. <화학식 14>의 합성 2-3. Synthesis of <Formula 14>

하기 반응식 7에 의하여 <화학식 14>를 합성하였다.<Formula 14> was synthesized by the following Scheme 7.

[반응식 7]Scheme 7

Figure pat00243
Figure pat00243

반응식 4에서 사용한 <1-b> 대신 <2-b>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <화학식14> 를 5.7g (48%) 제조하였다.5.7 g (48%) of <Chemical Formula 14> was prepared by the same method as the method except that <2-b> was used instead of <1-b> in Scheme 4.

MS(MALDI-TOF): m/z 728.41[M]+ MS (MALDI-TOF): m / z 728.41 [M] +

Anal.Calcd for C54H52N2 : C, 88.97; H, 7.19; N, 3.84. Found: C, 88.95; H, 7.20; N, 3.85
Anal.Calcd for C 54 H 52 N 2 : C, 88.97; H, 7. 19; N, 3.84. Found: C, 88.95; H, 7. 20; N, 3.85

합성예Synthetic example 3. 화학식 75의 합성 3. Synthesis of Chemical Formula 75

합성예Synthetic example 3-1. <3-a>의 합성 3-1. Synthesis of <3-a>

하기 반응식 8에 의하여 <3-a>를 합성하였다.<3-a> was synthesized according to Scheme 8 below.

[반응식 8]Scheme 8

Figure pat00244
Figure pat00244

반응식 2에서 사용한 2-메틸싸이클로헥사논 대신 2,6-디메틸싸이클로헥사논을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <3-a>를 32g (85%) 제조하였다.
32g (85%) of <3-a> was prepared by the same method except that 2,6-dimethylcyclohexanone was used instead of 2-methylcyclohexanone used in Scheme 2.

합성예Synthetic example 3-2. <3-b>의 합성 3-2. Synthesis of <3-b>

하기 반응식 9에 의하여 <3-b>를 합성하였다.<3-b> was synthesized by the following Scheme 9.

[반응식 9]Scheme 9

Figure pat00245
Figure pat00245

반응식 6에서 사용한 <2-a> 대신 <3-a>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <화학식14> 를 68.7g (93%) 제조하였다.
Except for using <3-a> instead of <2-a> used in Scheme 6 68.7g (93%) was prepared in the same manner.

합성예Synthetic example 3-3. <화학식 75>의 합성 3-3. Synthesis of <Formula 75>

하기 반응식 10에 의하여 <화학식 75>를 합성하였다.<Chemical Formula 75> was synthesized by the following Scheme 10.

[반응식 10]Scheme 10

Figure pat00246
Figure pat00246

반응식 4에서 사용한 <1-b> 대신 2,6-디브로모파이렌을 사용한 것과 <1-d>대신 <3-b>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <화학식75> 를 5.9g (52%) 제조하였다.Except for using 2,6-dibromopyrene instead of <1-b> in Scheme 4 and <3-b> instead of <1-d>, the compound was synthesized in the same manner to give <Chemical Formula 75> 5.9 g (52%) was prepared.

MS(MALDI-TOF): m/z 600.35[M]+ MS (MALDI-TOF): m / z 600.35 [M] +

Anal.Calcd for C44H44N2 : C, 87.96; H, 7.38; N, 4.66. Found: C, 87.89; H, 7.42; N, 4.69
Anal.Calcd for C 44 H 44 N 2 : C, 87.96; H, 7. 38; N, 4.66. Found: C, 87.89; H, 7. 42; N, 4.69

합성예Synthetic example 4. 화학식 101의 합성 4. Synthesis of Formula 101

합성예Synthetic example 4-1. <4-a>의 합성 4-1. Synthesis of <4-a>

하기 반응식 11에 의하여 <4-a>를 합성하였다.<4-a> was synthesized by the following Scheme 11.

[반응식 11]Scheme 11

Figure pat00247
Figure pat00247

500 ml 둥근 바닥 플라스크에 9-브로모페난쓰롤린 30g (0.1166mol), 디벤조하이드라존 27.5g(0.14mol), 팔라듐 아세테이트 1.05g(4.664 mmol), 바이넵 0.18g(4.664mmol), 소듐 텨셔리 부톡사이드 44.8g(0.4664mol), 톨루엔 240ml를 넣고,12 시간 동안 환류시킨다. 반응이 완료되면 뜨거운 상태에서 뷰흐너 깔대기에 셀라이트를 깔고 여과한다. 여액을 농축한 후, 헥산과 에틸아세테이트을 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 <4-a>을 31.7 g (73%) 제조하였다.
30 g (0.1166 mol) of 9-bromophenanthrosine, 27.5 g (0.14 mol) of dibenzohydrazone, 1.05 g (4.664 mmol) of palladium acetate, 0.18 g (4.664 mmol), sodium soap in a 500 ml round bottom flask Add 44.8 g (0.4664 mol) of sherry butoxide, 240 ml of toluene, and reflux for 12 hours. When the reaction is complete, place a celite and filter on a Buchner funnel in the hot state. After concentrating the filtrate, 31.7 g (73%) of <4-a> obtained by column chromatography using hexane and ethyl acetate as developing solvents were prepared.

합성예Synthetic example 4-2. <4-b>의 합성 4-2. Synthesis of <4-b>

하기 반응식 12에 의하여 <4-b>를 합성하였다.<4-b> was synthesized by the following Scheme 12.

[반응식 12][Reaction Scheme 12]

Figure pat00248
Figure pat00248

500 ml 둥근 바닥 플라스크에 반응식 11에서 얻은 <4-a>30g(0.0805mol), 싸이클로펜타논 6.78g(0.0805mol), 파라-톨루엔설포닉산 45.9g(0.2415mol), 에탄올 200ml을 넣고 12시간 동안 환류시킨다. 반응이 완료되면 수산화나트륨을 넣어 염기화시킨다. 에틸아세테이트 와 물을 넣고 추출하여 중화시킨다. 유기층을 무수처리 하여 감압 농축한 후 헥산과 에틸아세테이트을 전개용매로 사용하여 컬럼크로마토그래피로 분리하여 얻은 <4-b>을 15.7 g (76%) 제조하였다.
In a 500 ml round bottom flask, 30 g (0.0805 mol) of <4-a> obtained in Scheme 11, 6.78 g (0.0805 mol) of cyclopentanone, 45.9 g (0.2415 mol) of para-toluenesulphonic acid, and 200 ml of ethanol were added for 12 hours. Reflux. When the reaction is completed, sodium hydroxide is added to make the base. Add ethyl acetate and water to neutralize the extract. The organic layer was anhydrous, concentrated under reduced pressure, and then 15.7 g (76%) of <4-b> obtained by column chromatography using hexane and ethyl acetate as a developing solvent was prepared.

합성예Synthetic example 4-3. <4-c>의 합성 4-3. Synthesis of <4-c>

하기 반응식 13에 의하여 <4-c>를 합성하였다.<4-c> was synthesized by the following Scheme 13.

[반응식 13]Scheme 13

Figure pat00249
Figure pat00249

반응식 6에서 사용한 <2-a> 대신 <4-b>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <4-c> 를 11g (85%) 제조하였다.
Except for using <4-b> instead of <2-a> used in Scheme 6 it was synthesized in the same manner to give 11g (85%) of <4-c>.

합성예Synthetic example 4-4. <화학식 101>의 합성 4-4. Synthesis of <Formula 101>

하기 반응식 14에 의하여 <화학식 101>를 합성하였다.<Chemical Formula 101> was synthesized by the following Scheme 14.

[반응식 14][Reaction Scheme 14]

Figure pat00250
Figure pat00250

반응식 4에서 사용한 <1-b> 대신 브로모트리페닐렌을 사용한 것과 <1-d>대신 <4-c>을 사용한 것을 제외하고는 동일한 방법으로 합성하여 <화학식101> 를 3.6g (46%) 제조하였다.
3.6 g (46%) of <Formula 101> was synthesized in the same manner except that bromotriphenylene was used instead of <1-b> in Scheme 4 and <4-c> instead of <1-d>. ) Was prepared.

MS(MALDI-TOF): m/z 485.21[M]+ MS (MALDI-TOF): m / z 485.21 [M] +

Anal.Calcd for C37H27N : C, 91.51; H, 5.60; N, 2.88. Found: C, 91.52; H, 5.58; N, 2.89
Anal.Calcd for C 37 H 27 N : C, 91.51; H, 5. 60; N, 2.88. Found: C, 91.52; H, 5.58; N, 2.89

합성예Synthetic example 5. 화학식 195의 합성 5. Synthesis of Chemical Formula 195

합성예Synthetic example 5-1. <5-a>의 합성 5-1. Synthesis of <5-a>

하기 반응식 15에 의하여 <5-a>를 합성하였다.<5-a> was synthesized according to Scheme 15 below.

[반응식 15][Reaction Scheme 15]

Figure pat00251
Figure pat00251

250ml 둥근 바닥 플라스크에 브롬 92.1g(0.576mol), 염화 알루미늄 28.17 g(0.0211mol)을 넣고 외부온도를 영도로 낮춘다.In a 250 ml round bottom flask, 92.1 g (0.576 mol) of bromine and 28.17 g (0.0211 mol) of aluminum chloride are added and the external temperature is reduced to zero.

위 용액에 디벤조수베론 20g(0.096mol)을 30분동안 적가한다. 적가 후 1시간 정도 교반시킨 후 상온으로 승온시킨다. 반응 완료 후 외부온도를 영도로 낮춘 다음 물 100ml를 천천히 적가한다. 메틸클로라이드 100ml를 넣고 추출한 후 유기층을 중탄산나트륨 수용액으로 중화시킨다. 유기층을 무수처리한 후 유기용매를 감압농축하여, 헥산과 디클로로메탄을 전개용매로 사용하여 칼럼크로마토그래피로 분리하여 얻은 <5-a> 16g (47%)를 제조하였다.
20 g (0.096 mol) of dibenzosuberon was added dropwise to the solution for 30 minutes. After dropping, the mixture was stirred for about 1 hour and then heated to room temperature. After the reaction was completed, the external temperature was lowered to zero, and then 100 ml of water was slowly added dropwise. 100 ml of methyl chloride was added to the mixture, and the organic layer was neutralized with an aqueous sodium bicarbonate solution. After the anhydrous organic layer was treated, the organic solvent was concentrated under reduced pressure, and 16 g (47%) of the resulting compound was separated by column chromatography using hexane and dichloromethane as a developing solvent.

합성예Synthetic example 5-2. <5-c>의 합성 5-2. Synthesis of <5-c>

하기 반응식 16에 의하여 <5-c>를 합성하였다.<5-c> was synthesized according to Scheme 16 below.

[반응식 16][Reaction Scheme 16]

Figure pat00252
Figure pat00252

100ml 둥근 바닥 플라스크에 질소 분위기 하에서 2-브로모바이페닐 14.46g (0.047mol)을 테트라하이드로퓨란 50ml에 녹인 후 영하 78도로 냉각시킨다. 냉각후 n-뷰틸리튬(1.6M 헥산용액) 29.5ml(0.047mol)을 천천히 적가한다. 적가 후 상온에서 1시간 교반시킨다.In a 100 ml round bottom flask, 14.46 g (0.047 mol) of 2-bromobiphenyl was dissolved in 50 ml of tetrahydrofuran under a nitrogen atmosphere and cooled to minus 78 degrees. After cooling, 29.5 ml (0.047 mol) of n-butyllithium (1.6 M hexane solution) was slowly added dropwise. After dropping, the mixture is stirred at room temperature for 1 hour.

250ml 둥근 바닥 플라스크에 질소 분위기 하에서 <5-a> 15g(0.041mol)을 테트라하이드로퓨란 용액에 녹인다. 위 용액에 100ml 반응기의 용액을 천천히 적가한다. 상온에서 4시간 교반 후 2N 염산용액 70ml를 넣는다. 층 분리 후 유기용매를 감압 제거한 후 얻은 <5-b>에 아세트산 30ml, 메탄설포닉산 2ml를 넣고 2시간 정도 환류시킨다.Dissolve 15 g (0.041 mol) of <5-a> in a tetrahydrofuran solution in a 250 ml round bottom flask under nitrogen atmosphere. To the above solution is slowly added dropwise a solution of a 100 ml reactor. After stirring for 4 hours at room temperature, 70 ml of 2N hydrochloric acid solution is added. After separating the layers, the organic solvent was removed under reduced pressure, and 30 ml of acetic acid and 2 ml of methanesulphonic acid were added to <5-b> to reflux for about 2 hours.

상온으로 식힌 후 메틸클로라이드와 물로 추출한 후 층분리 하여 유기층을 무수처리 후 유기용매를 감압농축하여, 헥산과 디클로로메탄으로 재결정하여, <5-c> 7.6g (37%)를 제조하였다.
After cooling to room temperature, the mixture was extracted with methyl chloride and water, and the layers were separated. The organic layer was treated with anhydrous, and the organic solvent was concentrated under reduced pressure. The crystals were recrystallized from hexane and dichloromethane to give <7.6c (7.6%).

합성예Synthetic example 5-3. <화학식 194>의 합성 5-3. Synthesis of <Formula 194>

하기 반응식 17에 의하여 <화학식 194>를 합성하였다.<Formula 194> was synthesized by the following Scheme 17.

[반응식 17][Reaction Scheme 17]

Figure pat00253
Figure pat00253

반응식 4에서 사용한 <1-b> 대신 <5-c>를 사용한 것을 제외하고는 동일한 방법으로 합성하여 <화학식194> 를 2.8g (51%) 제조하였다.
Except for using <5-c> instead of <1-b> used in Scheme 4 it was synthesized in the same manner to give 2.8g (51%) of <Formula 194>.

MS(MALDI-TOF): m/z 752.43[M]+ MS (MALDI-TOF): m / z 752.43 [M] +

Anal.Calcd for C55H54N2 : C, 88.90; H, 7.33; N, 3.77. Found: C, 88.92; H, 7.29; N, 3.80
Anal.Calcd for C 55 H 54 N 2 : C, 88.90; H, 7. 33; N, 3.77. Found: C, 88.92; H, 7. 29; N, 3.80

실시예Example 1 ~ 5: 유기 발광다이오드의 제조 1 to 5: manufacturing of organic light emitting diodes

ITO 글래스의 발광 면적이 2mm x 2mm 크기가 되도록 패터닝한 후 세정하였다. 기판을 진공 챔버에 장착한 후 베이스 압력이 1x10-6 torr가 되도록 한 후 유기물을 상기 ITO위에 DNTPD(700Å), NPD(300Å), ADN + 본 발명에 의해 제조된 화합물 (3%)(300Å), Alq3 (350Å), LiF(5Å), Al(1,000Å)의 순서로 성막하였으며, 0.4mA에서 측정을 하였다.
The light emitting area of the ITO glass was patterned to have a size of 2 mm x 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure is 1x10 -6 torr, and the organic material is placed on the ITO DNTPD (700 kPa), NPD (300 kPa), ADN + Compound (3%) (300 kPa) prepared by the present invention. , Alq 3 (350 Å), LiF (5 Å), and Al (1,000 Å) were formed in this order and measured at 0.4 mA.

비교예Comparative example 1 One

비교예를 위한 유기발광다이오드 소자는 상기 실시예의 소자구조에서 발명에 의해 제조된 화합물 대신 C545T를 사용한 점을 제외하고 동일하게 제작하였다.The organic light emitting diode device for the comparative example was manufactured in the same manner except that C545T was used instead of the compound prepared by the invention in the device structure of the above example.

구분division 도판트Dopant 호스트Host VV Cd/ACd / A 발광색Luminous color 비교예1Comparative Example 1 C545TC545T ADNADN 6.096.09 11.4611.46 청록색Turquoise 실시예1Example 1 55 ADNADN 3.733.73 23.5623.56 청록색Turquoise 실시예2Example 2 1414 ADNADN 3.743.74 22.4522.45 청록색Turquoise 실시예3Example 3 7575 ADNADN 3.883.88 23.6123.61 청록색Turquoise 실시예4Example 4 101101 ADNADN 3.763.76 21.2521.25 청록색Turquoise 실시예5Example 5 194194 ADNADN 3.583.58 22.9922.99 청록색Turquoise

상기 표에서 보는 바와 같이 본 발명에 의하여 확보된 유기화합물은 비교예 1에 비하여 구동전압이 낮고, 발광효율이 우수한 특성을 보인다.As shown in the above table, the organic compound obtained by the present invention has a lower driving voltage and excellent luminous efficiency than Comparative Example 1.

Claims (8)

하기 화학식 1로 표시되는 아민 유도체:
< 화학식 1 >
Figure pat00254

상기 화학식 1에서,
X는 단결합 또는 CR11R12이고,
Y는 단결합 또는 CR13R14이며,
R1 내지 R14는 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 탄소수 6 내지 50의 아릴기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로 아릴기, 치환 또는 비치환된 탄소수 1 내지 20의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬아미노기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴아미노기, 치환 또는 비치환된 탄소수 1 내지 20의 알킬실릴기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴실릴기, 치환 또는 비치환된 탄소수 1 내지 50의 아릴알킬아미노기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 시아노기, 할로겐기, 게르마늄기, 중소수 및 수소로 이루어진 군으로부터 선택되고,
R1 내지 R14는 인접한 치환체와 탄소수 3 내지 60의 알킬렌, 탄소수 3 내지 60의 알케닐렌으로 연결되어 포화 또는 불포화 알킬 고리 또는 단일환 또는 다환의 방향족 고리를 형성할 수 있으며,
A는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기이고,
l은 1 내지 6의 정수이며, m은 1 내지 4의 정수이고, n은 1 내지 6의 정수이며, 이때, l, m, n이 2 이상인 경우 R1 내지 R14는 각각 같거나 다를 수 있다.An amine derivative represented by the following formula (1):
<Formula 1>
Figure pat00254

In Chemical Formula 1,
X is a single bond or CR 11 R 12 ,
Y is a single bond or CR 13 R 14 ,
R 1 to R 14 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted hetero atom having 3 to 50 carbon atoms Aryl group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms 6 Arylamino group of 30 to 30, substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino group having 1 to 50 carbon atoms, substituted or Unsubstituted alkenyl, substituted or unsubstituted alkynyl, cyano, halogen, germanium, small to medium and hydrogen;
R 1 To R 14 may be connected to an adjacent substituent and alkylene having 3 to 60 carbon atoms, alkenylene having 3 to 60 carbon atoms to form a saturated or unsaturated alkyl ring or a monocyclic or polycyclic aromatic ring,
A is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms,
l is an integer of 1 to 6, m is an integer of 1 to 4, n is an integer of 1 to 6, wherein when l, m, n is 2 or more, R 1 to R 14 may be the same or different. . 제1항에 있어서,
상기 X, Y, A, R1 내지 R14는 수소, 중수소, 시아노기, 할로겐기, 히드록시기, 니트로기, 탄소수 1 - 40의 알킬기, 탄소수 1 - 40의 알콕시기, 탄소수 1 - 40의 알케닐, 탄소수 1 - 40의 알키닐기, 탄소수 1 - 40의 알킬아미노기, 탄소수 6 - 40의 아릴아미노기, 탄소수 3 - 40의 헤테로아릴아미노기, 탄소수 1 - 40의 알킬실릴기, 탄소수 6 - 40의 아릴실릴기, 탄소수 6 - 40의 아릴기, 탄소수 3 - 40의 아릴옥시기, 탄소수 3 - 40의 헤테로아릴기, 게르마늄기, 인, 보론으로 이루어진 군으로부터 선택된 하나 이상의 치환기에 의해서 치환된 것을 특징으로 하는 아민 유도체. The method of claim 1,
X, Y, A, R 1 to R 14 are hydrogen, deuterium, cyano group, halogen group, hydroxy group, nitro group, C1-40 alkyl group, C1-40 alkoxy group, C1-40 alkenyl , Alkynyl group having 1 to 40 carbon atoms, alkylamino group having 1 to 40 carbon atoms, arylamino group having 6 to 40 carbon atoms, heteroarylamino group having 3 to 40 carbon atoms, alkylsilyl group having 1 to 40 carbon atoms, arylsilyl having 6 to 40 carbon atoms It is substituted by one or more substituents selected from the group consisting of a group, an aryl group having 6 to 40 carbon atoms, an aryloxy group having 3 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, a germanium group, phosphorus and boron. Amine derivatives. 제1항에 있어서,
상기 A는 치환 또는 비치환된 안트라센, 치환 또는 비치환된 파이렌, 치환 또는 비치환된 트리페닐렌, 치환 또는 비치환된 플루오란텐, 치환 또는 비치환된 스피로화합물로 이루어진 군 중에서 선택되는 것을 특징으로 하는 아민 유도체.The method of claim 1,
A is selected from the group consisting of substituted or unsubstituted anthracene, substituted or unsubstituted pyrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthene, substituted or unsubstituted spiro compound An amine derivative characterized by the above. 제3항에 있어서,
상기 A는 하기 화학식으로 표시되는 화합물 중에서 선택된 어느 하나인 것을 특징으로 하는 아민 유도체:
Figure pat00255
The method of claim 3,
A is an amine derivative, characterized in that any one selected from compounds represented by the following formula:
Figure pat00255
 제1항에 있어서,
하기 [화학식 2] 내지 [화학식 231]로 표시되는 군으로부터 선택된 어느 하나의 화합물인 것을 특징으로 하는 아민 유도체:

Figure pat00256
Figure pat00257

[화학식 2] [화학식 3]
Figure pat00258
Figure pat00259

[화학식 4] [화학식 5]
Figure pat00260
Figure pat00261

[화학식 6] [화학식 7]
Figure pat00262
Figure pat00263

[화학식 8] [화학식 9]
Figure pat00264
Figure pat00265

[화학식 10] [화학식 11]
Figure pat00266
Figure pat00267

[화학식 12] [화학식 13]
Figure pat00268
Figure pat00269

[화학식 14] [화학식 15]
Figure pat00270
Figure pat00271

[화학식 16] [화학식 17]
Figure pat00272
Figure pat00273

[화학식 18] [화학식 19]
Figure pat00274
Figure pat00275

[화학식 20] [화학식 21]
Figure pat00276
Figure pat00277

[화학식 22] [화학식 23]
Figure pat00278
Figure pat00279

[화학식 24] [화학식 25]
Figure pat00280
Figure pat00281

[화학식 26] [화학식 27]
Figure pat00282
Figure pat00283

[화학식 28] [화학식 29]
Figure pat00284
Figure pat00285

[화학식 30] [화학식 31]
Figure pat00286
Figure pat00287

[화학식 32] [화학식 33]
Figure pat00288
Figure pat00289

[화학식 34] [화학식 35]
Figure pat00290
Figure pat00291

[화학식 36] [화학식 37]
Figure pat00292
Figure pat00293

[화학식 38] [화학식 39]
Figure pat00294
Figure pat00295

[화학식 40] [화학식 41]
Figure pat00296
Figure pat00297

[화학식 42] [화학식 43]
Figure pat00298
Figure pat00299

[화학식 44] [화학식 45]
Figure pat00300
Figure pat00301

[화학식 46] [화학식 47]
Figure pat00302
Figure pat00303

[화학식 48] [화학식 49]
Figure pat00304
Figure pat00305

[화학식 50] [화학식 51]
Figure pat00306
Figure pat00307

[화학식 52] [화학식 53]
Figure pat00308
Figure pat00309

[화학식 54] [화학식 55]
Figure pat00310
Figure pat00311

[화학식 56] [화학식 57]
Figure pat00312
Figure pat00313

[화학식 58] [화학식 59]
Figure pat00314
Figure pat00315

[화학식 60] [화학식 61]
Figure pat00316
Figure pat00317

[화학식 62] [화학식 63]
Figure pat00318
Figure pat00319

[화학식 64] [화학식 65]
Figure pat00321

[화학식 66] [화학식 67]
Figure pat00322
Figure pat00323

[화학식 68] [화학식 69]
Figure pat00324
Figure pat00325

[화학식 70] [화학식 71]
Figure pat00326
Figure pat00327

[화학식 72] [화학식 73]
Figure pat00328
Figure pat00329

[화학식 74] [화학식 75]
Figure pat00330
Figure pat00331

[화학식 76] [화학식 77]
Figure pat00332
Figure pat00333

[화학식 78] [화학식 79]
Figure pat00334
Figure pat00335

[화학식 80] [화학식 81]
Figure pat00336
Figure pat00337

[화학식 82] [화학식 83]
Figure pat00338
Figure pat00339

[화학식 84] [화학식 85]
Figure pat00340
Figure pat00341

[화학식 86] [화학식 87]
Figure pat00342
Figure pat00343

[화학식 88] [화학식 89]
Figure pat00344
Figure pat00345

[화학식 90] [화학식 91]
Figure pat00346
Figure pat00347

[화학식 92] [화학식 93]
Figure pat00348
Figure pat00349

[화학식 94] [화학식 95]
Figure pat00350
Figure pat00351

[화학식 96] [화학식 97]
Figure pat00352
Figure pat00353

[화학식 98] [화학식 99]
Figure pat00354
Figure pat00355

[화학식 100] [화학식 101]
Figure pat00356
Figure pat00357

[화학식 102] [화학식 103]
Figure pat00358
Figure pat00359

[화학식 104] [화학식 105]
Figure pat00361

[화학식 106] [화학식 107]
Figure pat00362
Figure pat00363

[화학식 108] [화학식 109]
Figure pat00364
Figure pat00365

[화학식 110] [화학식 111]
Figure pat00366
Figure pat00367

[화학식 112] [화학식 113]
Figure pat00368
Figure pat00369

[화학식 114] [화학식 115]
Figure pat00370
Figure pat00371

[화학식 116] [화학식 117]
Figure pat00372
Figure pat00373

[화학식 118] [화학식 119]
Figure pat00374
Figure pat00375

[화학식 120] [화학식 121]
Figure pat00376
Figure pat00377

[화학식 122] [화학식 123]
Figure pat00378
Figure pat00379

[화학식 124] [화학식 125]
Figure pat00380
Figure pat00381

[화학식 126] [화학식 127]
Figure pat00382
Figure pat00383

[화학식 128] [화학식 129]
Figure pat00384
Figure pat00385

[화학식 130] [화학식 131]
Figure pat00386
Figure pat00387

[화학식 132] [화학식 133]
Figure pat00388
Figure pat00389

[화학식 134] [화학식 135]
Figure pat00390
Figure pat00391

[화학식 136] [화학식 137]
Figure pat00392
Figure pat00393

[화학식 138] [화학식 139]
Figure pat00394
Figure pat00395

[화학식 140] [화학식 141]
Figure pat00396
Figure pat00397

[화학식 142] [화학식 143]
Figure pat00398
Figure pat00399

[화학식 144] [화학식 145]
Figure pat00400
Figure pat00401

[화학식 146] [화학식 147]
Figure pat00402
Figure pat00403

[화학식 148] [화학식 149]
Figure pat00404
Figure pat00405

[화학식 150] [화학식 151]
Figure pat00406
Figure pat00407

[화학식 152] [화학식 153]
Figure pat00408
Figure pat00409

[화학식 154] [화학식 155]
Figure pat00410
Figure pat00411

[화학식 156] [화학식 157]
Figure pat00412
Figure pat00413

[화학식 158] [화학식 159]
Figure pat00414
Figure pat00415

[화학식 160] [화학식 161]
Figure pat00416
Figure pat00417

[화학식 162] [화학식 163]
Figure pat00418
Figure pat00419

[화학식 164] [화학식 165]
Figure pat00420
Figure pat00421

[화학식 166] [화학식 167]
Figure pat00422
Figure pat00423

[화학식 168] [화학식 169]
Figure pat00424
Figure pat00425

[화학식 170] [화학식 171]
Figure pat00426
Figure pat00427

[화학식 172] [화학식 173]
Figure pat00428
Figure pat00429

[화학식 174] [화학식 175]
Figure pat00430
Figure pat00431

[화학식 176] [화학식 177]
Figure pat00432
Figure pat00433

[화학식 178] [화학식 179]
Figure pat00434
Figure pat00435

[화학식 180] [화학식 181]
Figure pat00436
Figure pat00437

[화학식 182] [화학식 183]
Figure pat00438
Figure pat00439

[화학식 184] [화학식 185]
Figure pat00440
Figure pat00441

[화학식 186] [화학식 187]
Figure pat00442
Figure pat00443

[화학식 188] [화학식 189]
Figure pat00444
Figure pat00445

[화학식 190] [화학식 191]
Figure pat00446
Figure pat00447

[화학식 192] [화학식 193]
Figure pat00448
Figure pat00449

[화학식 194] [화학식 195]
Figure pat00450
Figure pat00451

[화학식 196] [화학식 197]
Figure pat00452
Figure pat00453

[화학식 198] [화학식 199]
Figure pat00454
Figure pat00455

[화학식 200] [화학식 201]
Figure pat00456
Figure pat00457

[화학식 202] [화학식 203]
Figure pat00458
Figure pat00459

[화학식 204] [화학식 205]
Figure pat00460
Figure pat00461

[화학식 206] [화학식 207]
Figure pat00462
Figure pat00463

[화학식 208] [화학식 209]
Figure pat00464
Figure pat00465

[화학식 210] [화학식 211]
Figure pat00466
Figure pat00467

[화학식 212] [화학식 213]
Figure pat00468
Figure pat00469

[화학식 214] [화학식 215]
Figure pat00470
Figure pat00471

[화학식 216] [화학식 217]
Figure pat00472
Figure pat00473

[화학식 218] [화학식 219]
Figure pat00474
Figure pat00475

[화학식 220] [화학식 221]
Figure pat00476
Figure pat00477

[화학식 222] [화학식 223]
Figure pat00478
Figure pat00479

[화학식 224] [화학식 225]
Figure pat00480
Figure pat00481

[화학식 226] [화학식 227]
Figure pat00482
Figure pat00483

[화학식 228] [화학식 229]
Figure pat00484
Figure pat00485

[화학식 230] [화학식 231]
The method of claim 1,
An amine derivative characterized in that the compound of any one selected from the group represented by the following [Formula 2] to [Formula 231]:

Figure pat00256
Figure pat00257

[Formula 2] [Formula 3]
Figure pat00258
Figure pat00259

[Formula 4] [Formula 5]
Figure pat00260
Figure pat00261

[Formula 6] [Formula 7]
Figure pat00262
Figure pat00263

[Formula 8] [Formula 9]
Figure pat00264
Figure pat00265

[Formula 10] [Formula 11]
Figure pat00266
Figure pat00267

[Formula 12] [Formula 13]
Figure pat00268
Figure pat00269

[Formula 14] [Formula 15]
Figure pat00270
Figure pat00271

[Formula 16] [Formula 17]
Figure pat00272
Figure pat00273

[Formula 18] [Formula 19]
Figure pat00274
Figure pat00275

[Formula 20] [Formula 21]
Figure pat00276
Figure pat00277

[Formula 22] [Formula 23]
Figure pat00278
Figure pat00279

[Formula 24] [Formula 25]
Figure pat00280
Figure pat00281

[Formula 26] [Formula 27]
Figure pat00282
Figure pat00283

[Formula 28] [Formula 29]
Figure pat00284
Figure pat00285

[Formula 30] [Formula 31]
Figure pat00286
Figure pat00287

[Formula 32] [Formula 33]
Figure pat00288
Figure pat00289

[Formula 34] [Formula 35]
Figure pat00290
Figure pat00291

[Formula 36] [Formula 37]
Figure pat00292
Figure pat00293

[Formula 38] [Formula 39]
Figure pat00294
Figure pat00295

[Formula 40] [Formula 41]
Figure pat00296
Figure pat00297

[Formula 42] [Formula 43]
Figure pat00298
Figure pat00299

[Formula 44] [Formula 45]
Figure pat00300
Figure pat00301

[Formula 46] [Formula 47]
Figure pat00302
Figure pat00303

[Formula 48] [Formula 49]
Figure pat00304
Figure pat00305

[Formula 50] [Formula 51]
Figure pat00306
Figure pat00307

[Formula 52] [Formula 53]
Figure pat00308
Figure pat00309

[Formula 54] [Formula 55]
Figure pat00310
Figure pat00311

[Formula 56] [Formula 57]
Figure pat00312
Figure pat00313

[Formula 58] [Formula 59]
Figure pat00314
Figure pat00315

[Formula 60] [Formula 61]
Figure pat00316
Figure pat00317

[Formula 62] [Formula 63]
Figure pat00318
Figure pat00319

[Formula 64] [Formula 65]
Figure pat00321

[Formula 66] [Formula 67]
Figure pat00322
Figure pat00323

[Formula 68] [Formula 69]
Figure pat00324
Figure pat00325

[Formula 70] [Formula 71]
Figure pat00326
Figure pat00327

[Formula 72] [Formula 73]
Figure pat00328
Figure pat00329

[Formula 74] [Formula 75]
Figure pat00330
Figure pat00331

[Formula 76] [Formula 77]
Figure pat00332
Figure pat00333

[Formula 78] [Formula 79]
Figure pat00334
Figure pat00335

[Formula 80] [Formula 81]
Figure pat00336
Figure pat00337

[Formula 82] [Formula 83]
Figure pat00338
Figure pat00339

[Formula 84] [Formula 85]
Figure pat00340
Figure pat00341

[Formula 86] [Formula 87]
Figure pat00342
Figure pat00343

[Formula 88] [Formula 89]
Figure pat00344
Figure pat00345

[Formula 90] [Formula 91]
Figure pat00346
Figure pat00347

[Formula 92] [Formula 93]
Figure pat00348
Figure pat00349

[Formula 94] [Formula 95]
Figure pat00350
Figure pat00351

[Formula 96] [Formula 97]
Figure pat00352
Figure pat00353

[Formula 98] [Formula 99]
Figure pat00354
Figure pat00355

[Formula 100] [Formula 101]
Figure pat00356
Figure pat00357

[Formula 102] [Formula 103]
Figure pat00358
Figure pat00359

[Formula 104] [Formula 105]
Figure pat00361

[Formula 106] [Formula 107]
Figure pat00362
Figure pat00363

[Formula 108] [Formula 109]
Figure pat00364
Figure pat00365

[Formula 110] [Formula 111]
Figure pat00366
Figure pat00367

[Formula 112] [Formula 113]
Figure pat00368
Figure pat00369

[Formula 114] [Formula 115]
Figure pat00370
Figure pat00371

[Formula 116] [Formula 117]
Figure pat00372
Figure pat00373

[Formula 118] [Formula 119]
Figure pat00374
Figure pat00375

[Formula 120] [Formula 121]
Figure pat00376
Figure pat00377

[Formula 122] [Formula 123]
Figure pat00378
Figure pat00379

[Formula 124] [Formula 125]
Figure pat00380
Figure pat00381

[Formula 126] [Formula 127]
Figure pat00382
Figure pat00383

[Formula 128] [Formula 129]
Figure pat00384
Figure pat00385

[Formula 130] [Formula 131]
Figure pat00386
Figure pat00387

[Formula 132] [Formula 133]
Figure pat00388
Figure pat00389

[Formula 134] [Formula 135]
Figure pat00390
Figure pat00391

[Formula 136] [Formula 137]
Figure pat00392
Figure pat00393

[Formula 138] [Formula 139]
Figure pat00394
Figure pat00395

[Formula 140] [Formula 141]
Figure pat00396
Figure pat00397

[Formula 142] [Formula 143]
Figure pat00398
Figure pat00399

[Formula 144] [Formula 145]
Figure pat00400
Figure pat00401

[Formula 146] [Formula 147]
Figure pat00402
Figure pat00403

[Formula 148] [Formula 149]
Figure pat00404
Figure pat00405

[Formula 150] [Formula 151]
Figure pat00406
Figure pat00407

[Formula 152] [Formula 153]
Figure pat00408
Figure pat00409

[Formula 154] [Formula 155]
Figure pat00410
Figure pat00411

[Formula 156] [Formula 157]
Figure pat00412
Figure pat00413

[Formula 158] [Formula 159]
Figure pat00414
Figure pat00415

[Formula 160] [Formula 161]
Figure pat00416
Figure pat00417

[Formula 162] [Formula 163]
Figure pat00418
Figure pat00419

[Formula 164] [Formula 165]
Figure pat00420
Figure pat00421

[Formula 166] [Formula 167]
Figure pat00422
Figure pat00423

[Formula 168] [Formula 169]
Figure pat00424
Figure pat00425

[Formula 170] [Formula 171]
Figure pat00426
Figure pat00427

[Formula 172] [Formula 173]
Figure pat00428
Figure pat00429

[Formula 174] [Formula 175]
Figure pat00430
Figure pat00431

[Formula 176] [Formula 177]
Figure pat00432
Figure pat00433

[Formula 178] [Formula 179]
Figure pat00434
Figure pat00435

[Formula 180] [Formula 181]
Figure pat00436
Figure pat00437

[Formula 182] [Formula 183]
Figure pat00438
Figure pat00439

[Formula 184] [Formula 185]
Figure pat00440
Figure pat00441

[Formula 186] [Formula 187]
Figure pat00442
Figure pat00443

[Formula 188] [Formula 189]
Figure pat00444
Figure pat00445

[Formula 190] [Formula 191]
Figure pat00446
Figure pat00447

[Formula 192] [Formula 193]
Figure pat00448
Figure pat00449

[Formula 194] [Formula 195]
Figure pat00450
Figure pat00451

[Formula 196] [Formula 197]
Figure pat00452
Figure pat00453

[Formula 198] [Formula 199]
Figure pat00454
Figure pat00455

[Formula 200] [Formula 201]
Figure pat00456
Figure pat00457

[Formula 202] [Formula 203]
Figure pat00458
Figure pat00459

[Formula 204] [Formula 205]
Figure pat00460
Figure pat00461

[Formula 206] [Formula 207]
Figure pat00462
Figure pat00463

[Formula 208] [Formula 209]
Figure pat00464
Figure pat00465

[Formula 210] [Formula 211]
Figure pat00466
Figure pat00467

[Formula 212] [Formula 213]
Figure pat00468
Figure pat00469

[Formula 214] [Formula 215]
Figure pat00470
Figure pat00471

[Formula 216] [Formula 217]
Figure pat00472
Figure pat00473

[Formula 218] [Formula 219]
Figure pat00474
Figure pat00475

[Formula 220] [Formula 221]
Figure pat00476
Figure pat00477

[Formula 222] [Formula 223]
Figure pat00478
Figure pat00479

[Formula 224] [Formula 225]
Figure pat00480
Figure pat00481

[Formula 226] [Formula 227]
Figure pat00482
Figure pat00483

[Formula 228] [Formula 229]
Figure pat00484
Figure pat00485

[Formula 230] [Formula 231]
애노드; 캐소드; 및 상기 애노드와 캐소드 사이에 제1항 내지 제5항 중 어느 한 항에 따른 아민 유도체를 포함하는 층을 구비한 유기전계발광소자.Anode; Cathode; And a layer including an amine derivative according to any one of claims 1 to 5 between the anode and the cathode. 제6항에 있어서,
상기 애노드와 캐소드 사이에 정공주입층, 정공수송층, 발광층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 6,
An organic light emitting device comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the anode and the cathode. 제6항에 있어서,
상기 아민 유도체는 상기 애노드 및 캐소드 사이의 전자수송층에 포함되는 것을 특징으로 하는 유기전계발광소자.The method of claim 6,
The amine derivative is an organic light emitting device, characterized in that included in the electron transport layer between the anode and the cathode.
KR1020100108676A 2010-11-03 2010-11-03 Amine derivatives and organoelectroluminescent device employing the same KR20120047038A (en)

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