KR20090086015A - Anthracene derivatives and organoelectroluminescent device including the same - Google Patents

Anthracene derivatives and organoelectroluminescent device including the same Download PDF

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KR20090086015A
KR20090086015A KR1020080072415A KR20080072415A KR20090086015A KR 20090086015 A KR20090086015 A KR 20090086015A KR 1020080072415 A KR1020080072415 A KR 1020080072415A KR 20080072415 A KR20080072415 A KR 20080072415A KR 20090086015 A KR20090086015 A KR 20090086015A
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KR101068224B1 (en
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제종태
이상해
김성훈
류고운
윤재상
김남이
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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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • 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
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass

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Abstract

An anthracene derivative is provided to improve power efficiency and luminous efficiency and to prepare an organic electroluminescence device with excellent lifetime. An anthracene derivative has a structure represented by chemical formula 1. An organic electroluminescence device comprises an anode, a cathode, and a layer which is interposed between anode and cathode and contains the anthracene derivative. The organic electroluminescence device further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole block layer, an electron transport layer, an electron injection layer, and an electron blocking layer between anode and cathode.

Description

안트라센 유도체 및 이를 포함하는 유기전계발광소자{Anthracene derivatives and organoelectroluminescent device including the same}Anthracene derivatives and organic electroluminescent devices including the same {Anthracene derivatives and organoelectroluminescent device including the same}

본 발명은 안트라센 유도체 및 상기 안트라센 유도체를 채용한 유기전계발광소자에 관한 것으로서, 더욱 상세하게는 유기전계발광소자에 사용하는 경우 전력효율 및 발광효율을 향상시키고, 또한 긴 수명을 갖게 하는 안트라센 유도체 및 상기 안트라센 유도체를 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to an anthracene derivative and an organic light emitting device employing the anthracene derivative, and more particularly, when used in an organic light emitting device, an anthracene derivative to improve power efficiency and luminous efficiency, and to have a long lifetime, and It relates to an organic electroluminescent device comprising the anthracene derivative.

유기전계발광소자 (이하, 유기 EL 소자라 함)는 정공주입전극인 제1 전극 (애노드 전극)과 전자주입전극인 제2 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 전기 적 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.

초창기의 대표적 유기전계발광소자는 1969년 구르니 (Gurnee)에 의해서 공지된 단층구조의 것으로서 (미국등록특허 제3,172,862호 및 미국등록특허 제3,173,050호), 100V 이상의 과도한 구동전압을 필요로 하기 때문에 실용화되기 어렵다는 문제점이 있었다. 따라서, 이러한 문제점을 해결하고자, 1987년 이스트만 코닥사 (Eastman Kodak co.)의 Tang에 의해 약 6 내지 14V 정도의 현저히 낮은 구동전압을 갖는 다층구조의 유기전계발광소자가 개발되었으며 (C. W. Tang et al., Appl . Phys . Lett., 51, 913(1987); J. Applied Phys., 65, 3610(1989); US4,356,429), 현재는 정공주입층, 정공수송층, 전자수송층 및 전자주입층 등과 같은 다양한 기능성 적층구조들을 갖는 유기전계발광소자들이 지속적으로 개발되고 있는 추세이다.Representative organic electroluminescent devices of the early days have a single layer structure known by Gurnee in 1969 (US Patent No. 3,172,862 and US Patent No. 3,173,050), and are practically used because they require excessive driving voltage of 100 V or more. There was a problem that it is difficult to be. Therefore, in order to solve this problem, a multi-layered organic electroluminescent device having a significantly low driving voltage of about 6 to 14 V was developed by Tang of Eastman Kodak Co. in 1987 (CW Tang et al. ., Appl . Phys . Lett ., 51, 913 (1987); J. Applied. Phys ., 65, 3610 (1989); US 4,356,429), and now organic light emitting devices having various functional laminated structures such as a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer are continuously being developed.

한편, 종래의 유기전계발광소자에는 안트라센 및 그 유도체가 다양한 용도로 채용된 바 있는데, "ADN"이라는 약어로 잘 알려진 9,10-디(2-나프틸)안트라센 (미국등록특허 제5,935,721호), 9-나프틸-10-페닐안트라센 유도체 (미국공개특허공보 제2006/0014046호) 및 9-비페닐-10-나프틸안트라센 유도체 (국제특허공개공보 제2005/080527호) 등은 발광층의 호스트로서 사용된 바 있고, 비스-안트라센을 발광층으로 사용하여 유기전계발광소자의 수명을 개선시킨 기술도 개시된 바 있다 (미국등록특허 제6,534,199호). 또한, 정공수송층 (HTL)에 안트라센 유도체를 채용한 기술도 개시된 바 있으며 (미국등록특허 제6,465,115호 및 미국등록특허 제5,759,444호), 그 밖에도 다양한 용도로 안트라센 및 그 유도체가 유기전계발광소 자에 채용된 바 있다.On the other hand, anthracene and its derivatives have been employed in various conventional organic electroluminescent devices, and 9,10-di (2-naphthyl) anthracene, which is well known as an abbreviation of "ADN" (US Patent No. 5,935,721). , 9-naphthyl-10-phenylanthracene derivatives (US Patent Publication No. 2006/0014046) and 9-biphenyl-10-naphthylanthracene derivatives (International Patent Publication No. 2005/080527) and the like are hosts of the light emitting layer. As a light emitting layer, bis-anthracene has been used as a light emitting layer to improve the lifespan of an organic light emitting display device (US Pat. No. 6,534,199). In addition, a technique using an anthracene derivative in the hole transport layer (HTL) has also been disclosed (US Pat. No. 6,465,115 and US Pat. No. 5,759,444), and anthracene and its derivatives have been applied to organic electroluminescent devices for various purposes. It was adopted.

상술한 바와 같이, 유기전계발광소자에 안트라센을 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 호스트 (host)에 도펀트 (dopant)를 도핑하는 에너지 이동 원리를 기본으로 하는 호스트-게스트 시스템에 있어서, 발광층 호스트 물질로서 새로운 안트라센 유도체에 대한 많은 연구가 필요한 상황이다.As described above, many studies have been made in which anthracene is employed in the organic light emitting display device, but until now, the present conditions have not sufficiently satisfied characteristics such as brightness, efficiency, driving stability, and lifespan. Various technological developments are urgently needed. In particular, in a host-guest system based on the principle of energy transfer in which a dopant is doped to a light emitting layer host, a lot of research on a new anthracene derivative as a light emitting layer host material is required.

따라서, 본 발명이 달성하고자 하는 첫 번째 과제는 유기전계발광소자의 전력효율 및 발광효율을 향상시키면서, 또한 긴 수명을 갖게 하는 안트라센 유도체를 제공하는 것이다.Accordingly, the first object of the present invention is to provide an anthracene derivative that improves the power efficiency and luminous efficiency of an organic light emitting display device and also has a long lifetime.

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

상기 첫 번째 과제를 달성하기 위하여 본 발명은 하기 화학식 1의 안트라센 유도체를 제공한다.In order to achieve the first object of the present invention provides an anthracene derivative of the formula (1).

Figure 112008053423335-PAT00002
(1)
Figure 112008053423335-PAT00002
(One)

상기 식에서 X1 내지 X10은 각각 독립적으로 수소 원자, 중수소 원자, 할로겐 원자, 탄소수 1 내지 10인 알킬실릴, 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 10 내지 60의 축합방향족환, 치환 또는 비치환된 스티릴기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 비닐기, 치환 또는 비치환된 카르보닐기, 치환 또는 비치환된 카르복실기, 치환 또는 비치환된 아릴치오기, 치환 또는 비치환된 탄소수 4 내지 40의 시클로알칸, 치환 또는 비치환된 탄소수 4 내지 20의 시클로알켄, 치환 또는 비치환된 탄소수 1 내지 60의 알콕시, 치환 또는 비치환된 탄소수 1 내지 60의 직쇄, 분기 또는 환상의 알킬기 또는 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기 또는 탄소수 3 내지 40의 헤테로아릴기이며, Wherein X 1 to X 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an alkylsilyl having 1 to 10 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted condensed aromatic ring having 10 to 60 carbon atoms, a substituted or Unsubstituted styryl group, substituted or unsubstituted amino group, substituted or unsubstituted vinyl group, substituted or unsubstituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted aryl group, substituted or unsubstituted carbon number 4 to 40 cycloalkane, substituted or unsubstituted cycloalkene having 4 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 60 carbon atoms, substituted or unsubstituted straight chain, branched or cyclic alkyl group having 1 to 60 carbon atoms or Each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms,

상기 치환된 알콕시, 직쇄, 분기 또는 환상의 알킬기, 아미노기, 비닐기, 카르보닐기, 카르복실기, 아릴치오기, 탄소수 4 내지 40의 시클로알칸 또는 탄소수 4 내지 20의 시클로알켄은 탄소수 1 내지 10의 알콕시기, 시아노기, 탄소수 1 내지 10의 알킬아미노기, 탄소수 1 내지 10의 알킬실릴기, 할로겐기, 탄소수 6 내지 10의 아릴기, 탄소수 6 내지 10의 아릴옥시기, 탄소수 6 내지 10의 아릴아미노기, 탄소수 6 내지 10의 아릴실릴기, 탄소수 3 내지 19의 헤테로아릴기 또는 수소로 이루어진 군으로부터 선택된 하나 이상의 치환기에 의해서 치환된 것이며, Substituted Alkoxy, straight chain, branched or cyclic alkyl group, amino group, vinyl group, carbonyl group, carboxyl group, aryl group, cycloalkane having 4 to 40 carbon atoms or cycloalkene having 4 to 20 carbon atoms, alkoxy group having 1 to 10 carbon atoms, cyano group, C1-C10 alkylamino group, C1-C10 alkylsilyl group, halogen group, C6-C10 aryl group, C6-C10 aryloxy group, C6-C10 arylamino group, C6-C10 Is substituted by one or more substituents selected from the group consisting of an arylsilyl group, a heteroaryl group having 3 to 19 carbon atoms or hydrogen,

상기 치환된 탄소수 6 내지 60의 아릴기, 탄소수 3 내지 40의 헤테로아릴기, 탄소수 10 내지 60의 축합방향족환 또는 치환된 스티릴기는 수소 원자, 중수소 원자, 할로겐 원자, 탄소수 1 내지 10인 알킬실릴, 탄소수 1내지 20의 알킬기, 탄소수 1 내지 10의 알콕시기, 시아노기, 탄소수 1 내지 10의 알킬아미노기, 탄소수 1 내지 10의 알킬실릴기, 할로겐기, 탄소수 6 내지 10의 아릴기, 탄소수 6 내지 10의 아릴옥시기, 탄소수 6 내지 10의 아릴아미노기, 탄소수 6 내지 10의 아릴실릴기, 탄소수 3 내지 19의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 치환 기에 의해서 치환된 것이고, 상기 치환체는 각각 독립적으로 인접하는 그룹과 결합하여 환을 형성할 수 있으며,The substituted aryl group having 6 to 60 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, condensed aromatic ring having 10 to 60 carbon atoms or substituted styryl group is hydrogen atom, deuterium atom, halogen atom, alkyl silyl having 1 to 10 carbon atoms , An alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cyano group, an alkylamino group having 1 to 10 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, a halogen group, an aryl group having 6 to 10 carbon atoms, and 6 to 6 carbon atoms. A aryloxy group having 10, an arylamino group having 6 to 10 carbon atoms, an arylsilyl group having 6 to 10 carbon atoms and a heteroaryl group having 3 to 19 carbon atoms, which is substituted with one or more substituents, each of which is independently Can combine with adjacent groups to form a ring,

여기에서 X1 내지 X10 중 적어도 어느 하나 이상은 중수소에 의하여 치환된 탄소수 6 내지 60의 아릴기 또는 탄소수 3 내지 40의 헤테로아릴기이다.At least any one of X 1 to X 10 here is an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms substituted with deuterium.

또한 본 발명은 상기 화학식 1의 X2, X7, X5 및 X10 중 적어도 어느 하나 이상은

Figure 112008053423335-PAT00003
인 것을 특징으로 하는 안트라센 유도체를 제공한다.In addition, the present invention is at least one of X2, X7, X5 and X10 of the formula (1)
Figure 112008053423335-PAT00003
It provides an anthracene derivative characterized in that.

본 발명은 상기 안트라센 유도체로서 하기 화학식 2의 구조를 갖는 안트라센 유도체를 제공한다.The present invention provides an anthracene derivative having the structure of Formula 2 as the anthracene derivative.

_

Figure 112008053423335-PAT00004
Figure 112008053423335-PAT00005
Figure 112008053423335-PAT00006
Figure 112008053423335-PAT00007
_
Figure 112008053423335-PAT00004
Figure 112008053423335-PAT00005
Figure 112008053423335-PAT00006
Figure 112008053423335-PAT00007

Figure 112008053423335-PAT00008
Figure 112008053423335-PAT00008

Figure 112008053423335-PAT00009
Figure 112008053423335-PAT00009

Figure 112008053423335-PAT00010
Figure 112008053423335-PAT00010

Figure 112008053423335-PAT00011
Figure 112008053423335-PAT00011

Figure 112008053423335-PAT00012
Figure 112008053423335-PAT00012

Figure 112008053423335-PAT00013
Figure 112008053423335-PAT00014
Figure 112008053423335-PAT00015
Figure 112008053423335-PAT00013
Figure 112008053423335-PAT00014
Figure 112008053423335-PAT00015

Figure 112008053423335-PAT00016
Figure 112008053423335-PAT00017
Figure 112008053423335-PAT00018
Figure 112008053423335-PAT00019
Figure 112008053423335-PAT00016
Figure 112008053423335-PAT00017
Figure 112008053423335-PAT00018
Figure 112008053423335-PAT00019

Figure 112008053423335-PAT00020
Figure 112008053423335-PAT00020

Figure 112008053423335-PAT00021
Figure 112008053423335-PAT00022
Figure 112008053423335-PAT00023
Figure 112008053423335-PAT00024
Figure 112008053423335-PAT00021
Figure 112008053423335-PAT00022
Figure 112008053423335-PAT00023
Figure 112008053423335-PAT00024

Figure 112008053423335-PAT00025
Figure 112008053423335-PAT00026
Figure 112008053423335-PAT00025
Figure 112008053423335-PAT00026

Figure 112008053423335-PAT00027
Figure 112008053423335-PAT00028
Figure 112008053423335-PAT00027
Figure 112008053423335-PAT00028

Figure 112008053423335-PAT00029
Figure 112008053423335-PAT00030
Figure 112008053423335-PAT00029
Figure 112008053423335-PAT00030

Figure 112008053423335-PAT00031
Figure 112008053423335-PAT00032
Figure 112008053423335-PAT00033
Figure 112008053423335-PAT00034
Figure 112008053423335-PAT00031
Figure 112008053423335-PAT00032
Figure 112008053423335-PAT00033
Figure 112008053423335-PAT00034

Figure 112008053423335-PAT00035
Figure 112008053423335-PAT00035

Figure 112008053423335-PAT00036
Figure 112008053423335-PAT00036

Figure 112008053423335-PAT00037
Figure 112008053423335-PAT00037

Figure 112008053423335-PAT00038
Figure 112008053423335-PAT00038

Figure 112008053423335-PAT00039
Figure 112008053423335-PAT00039

본 발명은 상기 두 번째 과제를 달성하기 위하여, 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되며, 상기 화학식 1 또는 2의 안트라센 유도체를 포 함하는 층을 구비한 유기전계발광소자를 제공한다.The present invention, in order to achieve the second object, an anode; Cathode; And it is interposed between the anode and the cathode, and provides an organic electroluminescent device having a layer containing the anthracene derivative of the formula (1) or (2).

또한 본 발명에 따른 유기전계발광소자는 상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 정공저지층, 전자수송층, 전자주입층 및 전자저지층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하며, 상기 안트라센 유도체를 포함하는 층은 발광층이다.In addition, the organic light emitting device according to the present invention further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode, The layer containing the anthracene derivative is a light emitting layer.

본 발명에 따른 안트라센 유도체는 유기전계발광소자에 사용되는 경우 전력효율 및 발광효율을 동등 이상으로 향상, 유지시키면서도, 월등히 우수한 수명특성을 갖는 유기전계발광소자를 제조할 수 있게 한다.When the anthracene derivative according to the present invention is used in an organic light emitting device, it is possible to manufacture an organic light emitting device having an excellent lifespan while improving and maintaining power efficiency and luminous efficiency at an equivalent or higher.

이하, 본 발명을 더욱 상세하게 설명하기로 한다.Hereinafter, the present invention will be described in more detail.

본 발명은 종래 발광층 호스트 물질 등에 폭넓게 사용되고 있는 안트라센 유도체의 휘도, 효율, 구동 안정성 및 수명 등의 특성을 개선하기 위한 것이며, 특히 상기 화학식 1로 표시되는 구조를 갖는 안트라센 유도체가 뛰어난 전력효율, 발광효율 및 수명특성을 갖는다는 점에 착안하여 완성한 것이다.The present invention is to improve the characteristics such as brightness, efficiency, driving stability and lifespan of anthracene derivatives widely used in conventional light emitting layer host materials, etc. In particular, anthracene derivatives having the structure represented by Formula 1 have excellent power efficiency and luminous efficiency. And focusing on having a lifespan characteristic.

상기 화학식 1의 안트라센 유도체를 살펴보면, 본 발명에 따른 안트라센 유도체는 안트라센을 기본골격으로 하며, 상기 안트라센 유도체의 치환기(X1 내지 X10) 중 적어도 하나 이상은 하나 이상의 수소가 중수소에 의하여 치환된 탄소수 6 내지 60의 아릴기이다.Looking at the anthracene derivative of Formula 1, the anthracene derivative according to the present invention is an anthracene as a basic skeleton, at least one or more of the substituents (X1 to X10) of the anthracene derivative is 6 to 6 carbon atoms substituted by deuterium 60 is an aryl group.

즉, 본 발명에 따른 안트라센 유도체는 안트라센 유도체에 치환되는 아릴기 가 중수소로 치환된 구조를 가지며, 상기 구조의 안트라센 유도체가 유기전계발광소자에 사용되는 경우 유기전계발광소자의 수명 등과 같은 특성이 놀랍게 향상된다.That is, the anthracene derivative according to the present invention has a structure in which the aryl group substituted in the anthracene derivative is substituted with deuterium, and when the anthracene derivative of the structure is used in an organic light emitting device, the characteristics such as the lifespan of the organic light emitting device are surprisingly surprising. Is improved.

상기 안트라센 유도체에 대한 본 발명의 일 실시예에서, 상기 아릴기는 중수소가 5개 치환된 페닐기이며, 상기 페닐기는 상기 안트라센 구조의 2번, 6번, 9번 및 10번 위치 중 적어도 어느 하나 이상의 위치에 결합한다. 이러한 중수소-치환 페닐기가 안트라센 구조에 결합함으로써 유기전계발광소자의 수명 특성이 놀랍게 향상되지며, 이는 하기 실시예에서 보다 상세히 설명한다. 하지만, 본 발명의 범위는 상기 중수소-치환 페닐기에 제한되지 않는다.In one embodiment of the present invention for the anthracene derivative, the aryl group is a phenyl group substituted with 5 deuterium, the phenyl group is at least any one of positions 2, 6, 9 and 10 of the anthracene structure To combine. By combining such deuterium-substituted phenyl group with the anthracene structure, the lifespan characteristics of the organic light emitting display device are surprisingly improved, which will be described in more detail in the following examples. However, the scope of the present invention is not limited to the deuterium-substituted phenyl group.

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 3 내지 20의 헤테로아릴기 또는 탄소수 6 내지 20의 헤테로아릴알킬기로 치 환될 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, C3-C20 heteroaryl group or C6 It may hwandoel value to a heteroarylalkyl group 20.

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 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).The 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 include aromatic groups such as phenyl, naphthyl, tetrahydronaphthyl and the like, and one or more hydrogen atoms of the aryl group may be substituted with the same substituents as in the case of the alkyl group (for example, When substituted with an amino group, an "arylamino group", when substituted with a silyl group, an "arylsilyl group", and when substituted with an oxy group, "aryloxy group".

본 발명의 화합물에서 사용되는 치환기인 헤테로아릴기는 N, O, P 또는 S 중에서 선택된 1, 2 또는 3개의 헤테로 원자를 포함하고, 나머지 고리 원자가 탄소인 탄소수 3 내지 30의 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.Heteroaryl group which is a substituent used in the compound of the present invention means a ring aromatic system having 3 to 30 carbon atoms containing 1, 2 or 3 hetero atoms selected from N, O, P 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 발명은 상기 안트라센 유도체의 일 예로 상기 화학식 2의 구조를 갖는 안트라센 유도체를 제공한다. 하지만, 본 발명의 범위는 이에 제한되지 않으며, 상기 화학식 1의 구조를 만족하는 한 변형된 다양한 구조의 안트라센 유도체가 가능하며, 이는 본 발명의 범위에 속한다.The present invention provides an anthracene derivative having the structure of Formula 2 as an example of the anthracene derivative. However, the scope of the present invention is not limited thereto, and as long as it satisfies the structure of Chemical Formula 1, anthracene derivatives of various modifications may be possible, which belongs to the scope of the present invention.

또한, 본 발명은 상기 두 번째 기술적 과제를 달성하기 위해서, 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재된 상기 화학식 1 및 2로 표시되는 안트라센 유도체를 포함하는 층을 구비한 유기전계발광소자를 제공한다.In addition, the present invention, in order to achieve the second technical problem, an anode; Cathode; And it provides an organic electroluminescent device having a layer comprising an anthracene derivative represented by the formula (1) and (2) interposed between the anode and the cathode.

즉, 본 발명에 따른 안트라센 유도체는 상술한 바와 같이 다양한 형태가 가능하며, 본 발명에 따른 유기전계발광소자는 본 발명에 따른 안트라센 유도체의 형태 중 적어도 하나 이상을 사용한다.That is, the anthracene derivative according to the present invention may have various forms as described above, and the organic light emitting device according to the present invention uses at least one or more of the forms of the anthracene derivative according to the present invention.

본 발명에 따른 유기전계발광소자는 상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 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.The organic light emitting device according to the present invention may further include at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer and an electron injection layer between the anode and the cathode, the hole injection layer, hole transport layer , The electron transport layer and the electron injection layer serves to increase the probability of light emitting bonds in the light emitting polymer by efficiently transferring holes or electrons to the light emitting polymer.

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. 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 있으며, 예를 들어 CuPc, 스타버스트(Starburst)형 아민류인 TCTA, m-MTDATA, IDE406 (이데미쯔사 재료) 등을 사용할 수 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. 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 also be used without particular limitation as long as it is commonly used in the art. For example, CuPc, TCTA which is a starburst type amine, m-MTDATA, IDE406 (made by Idemitsu Corp.), etc. can be used.

Figure 112008053423335-PAT00040
Figure 112008053423335-PAT00040

CuPcCuPc

Figure 112008053423335-PAT00041
Figure 112008053423335-PAT00041

TCTATCTA

Figure 112008053423335-PAT00042
Figure 112008053423335-PAT00042

m-MTDATAm-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 당업계에서 사용되는 물질인 한 특별히 제한되지 않으며, 예를 들어, 8-히드록시퀴놀린 알루미늄 (Alq3), PBD(2-(4-비페닐일)-5-(4-t-부틸페닐)-1,3,4-옥사디아졸), TNF(2,4,7-트리니트로 플루오레논), BMD, BND 등을 사용할 수 있다.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 material is not particularly limited as long as it is a material used in the art, for example, 8-hydroxyquinoline aluminum (Alq 3), PBD (2- (4-biphenylyl) -5- (4- t-butylphenyl) -1,3,4-oxadiazole), TNF (2,4,7-trinitro fluorenone), BMD, BND and the like can be used.

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 등 과 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. have. 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 안트라센 유도체를, 애노드 및 캐소드 사이에 개재되는 다양한 적층 구조 내에 포함할 수 있지만, 바람직하게는, 상기 안트라센 유도체는 애노드 및 캐소드 사이의 발광층 중에 사용할 수 있으며, 보다 바람직하게는 상기 발광층의 호스트 물질로 사용할 수 있다. 하지만, 다른 적층 구조층에 본 발명의 안트라센 유도체가 사용될 수 있으며, 이는 본 발명의 범위에 속한다.On the other hand, the organic electroluminescent device according to the present invention may include the anthracene derivative in a variety of laminated structures interposed between the anode and the cathode, preferably, the anthracene derivative may be used in the light emitting layer between the anode and the cathode More preferably, it can be used as a host material of the light emitting layer. However, the anthracene derivative of the present invention may be used in other laminated structure layers, which is within the scope of the present invention.

또한, 상기 안트라센 유도체를 포함하는 상기 발광층의 두께는 5nm 내지 500nm일 수 있는데, 두께가 5nm 미만인 경우에는 발광 효율이 저하되고, 500nm를 초과하는 경우에는 구동 전압이 상승되어 바람직하지 못하기 때문이다. 하지만, 본 발명의 범위는 상기 수치 범위에 제한되지 않으며, 본 발명에 따른 안트라센 유도체를 유기전계발광소자에 사용하는 한 본 발명의 범위에 속한다.In addition, the thickness of the light emitting layer including the anthracene derivative may be 5 nm to 500 nm, because when the thickness is less than 5 nm, the luminous efficiency is lowered, and when it exceeds 500 nm, the driving voltage is increased, which is not preferable. However, the scope of the present invention is not limited to the above numerical range, and is within the scope of the present invention as long as the anthracene derivative according to the present invention is used in the organic electroluminescent device.

이하, 본 발명에 따라 제조된 유기전계발광소자에 관한 다양한 형태를 도 1a 내지 1e를 참조하여 설명한다.Hereinafter, various forms of the organic light emitting display device manufactured according to the present invention will be described with reference to FIGS. 1A to 1E.

상기 도면을 참조하여, 본 발명에 따른 유기전계발광소자의 제조방법을 살펴보면 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.Referring to the drawings, a method of manufacturing an organic light emitting display device according to the present invention is first coated with an anode material 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. 마지막으 로, 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 metal for forming cathode is formed on the electron injection layer by vacuum thermal deposition. It is possible to manufacture an organic light emitting device according to. 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.

하지만, 도 1a 내지 도 1e를 통하여 알 수 있듯이, 상기 캐소드와 애노드 사이의 층간 구조는 사용하고자 하는 유기전계발광소자의 특성에 따라 일부 생략, 변형될 수 있으나, 이러한 구조에 상관없이 본 발명에 따른 안트라센 유도체를 상기 캐소드와 애노드 사이의 임의의 층에 사용하는 모든 유기전계발광소자에 대하여 본 발명의 범위는 미친다.However, as can be seen through FIGS. 1A to 1E, the interlayer structure between the cathode and the anode may be partially omitted or modified according to the characteristics of the organic light emitting device to be used, regardless of the structure according to the present invention. The scope of the present invention extends to all organic electroluminescent devices in which anthracene derivatives are used in any layer between the cathode and anode.

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.

실시예Example 1 One

2,7-2,7- 디페닐Diphenyl -9,10--9,10- 비스(펜타듀테리오페닐)안트라센의Of bis (pentadierterophenyl) anthracene 합성 및 이를 이용한  Synthesis and Using the Same 유기전계발광소자의Of organic light emitting device 제조 Produce

실시예Example 1-1 1-1

2,7-2,7- 디브로모Dibromo -9,10-디히드록시-9,10--9,10-dihydroxy-9,10- 디페닐안트라센의Diphenylanthracene 합성 synthesis

먼저 하기 반응식에 따라 2,7-디브로모-9,10-디히드록시-9,10-디페닐안트라센을 합성하였다.First, 2,7-dibromo-9,10-dihydroxy-9,10-diphenylanthracene was synthesized according to the following scheme.

Figure 112008053423335-PAT00043
Figure 112008053423335-PAT00043

상기 반응을 살펴보면, 1 리터의 둥근바닥 플라스크에 펜타듀테리오브로모벤젠(pentaduteriobromobenzene) 40.0 ml (0.38 mol), THF 520 mL를 넣은 후, 영하 78℃까지 냉각시켰다. 이어서, n-부틸리튬 205.6 mL (1.6M, 0.33 mol)를 천천히 적가하고, 동일한 온도에서 30분 동안 교반한 후, 2,7-디브로모안트라퀴논(2,7-dibromoanthraquinone) 34.4g (0.09 mol)를 첨가하였다. 상기 반응 결과물을 상온으로 승온한 후 반응물에 2 N 염산 260 ml를 첨가하였다. 결과물을 층 분리하여 유기층을 농축 후 후속 반응을 진행하는 단계로 진행하였다.Looking at the reaction, 40.0 ml (0.38 mol) of pentauteriobromobenzene (0.38 mol) and THF 520 mL were added to a 1 liter round bottom flask, and then cooled to minus 78 ° C. Then, 205.6 mL (1.6M, 0.33 mol) of n-butyllithium was slowly added dropwise, stirred at the same temperature for 30 minutes, and then 34.4 g (2,7-dibromoanthraquinone) 34.4 g (0.09) mol) was added. After raising the reaction product to room temperature, 260 ml of 2 N hydrochloric acid was added to the reaction. The resulting layer was separated and the organic layer was concentrated and proceeded to the subsequent reaction.

실시예Example 1-2 1-2

2,7-2,7- 디브로모Dibromo -9,10-디히드록시-9,10--9,10-dihydroxy-9,10- 디페닐안트라센의Diphenylanthracene 합성 synthesis

이후, 상기 합성된 2,7-디브로모-9,10-디히드록시-9,10-디페닐안트라센으로 부터 2,7-디브로모-9,10-비스(펜타듀테리오페닐)안트라센을 합성하였는데, 반응식은 아래와 같다.Then, 2,7-dibromo-9,10-bis (pentaduteriophenyl) from the synthesized 2,7-dibromo-9,10-dihydroxy-9,10-diphenylanthracene Anthracene was synthesized, and the reaction scheme is as follows.

Figure 112008053423335-PAT00044
Figure 112008053423335-PAT00044

상기 반응을 살펴보면, 500 mL의 둥근바닥 플라스크에 반응식 4로부터 얻은 2,7-디브로모-9,10-디히드록시-9,10-비스(펜타듀테리오페닐)안트라센을 넣은 후, KI 46.8 g (0.28 mol), NaH2PO2-H2O 49.6 g (0.56 mol), 아세트산 350 ml를 첨가하여 3시간 동안 환류냉각시켰다. 결과물을 상온으로 냉각하고, 여과한 다음, 과량의 물과 메탄올로 세척하였다. 세척 결과물을 건조시킨 다음, 톨루엔으로 재결정하여 생성된 고체를 여과한 후, 감압 건조하여 2,7-디브로모-9,10-비스(펜타듀테리오페닐)안트라센 (2,7-dibromo-9,10-bis(pentaduteriophenyl)anthracene) 45.9 g (실시예 1-1의 2,7-디브로모안트라퀴논 대비 수득률 85%)을 수득하는 단계로 진행하였다.Looking at the reaction, in a 500 mL round bottom flask was added 2,7-dibromo-9,10-dihydroxy-9,10-bis (pentaduteriophenyl) anthracene from Scheme 4, and then KI 46.8 g (0.28 mol), 49.6 g (0.56 mol) of NaH 2 PO 2 -H 2 O, and 350 ml of acetic acid were added and reflux-cooled for 3 hours. The result was cooled to room temperature, filtered and washed with excess water and methanol. The washed result was dried and then recrystallized with toluene, and the resulting solid was filtered and dried under reduced pressure to give 2,7-dibromo-9,10-bis (pentaduteriophenyl) anthracene (2,7-dibromo- 45.9 g of 9,10-bis (pentaduteriophenyl) anthracene) (85% yield of 2,7-dibromoanthraquinone of Example 1-1) was obtained.

실시예Example 1-3 1-3

2,7-2,7- 디페닐Diphenyl -9,10--9,10- 비스(펜타듀테리오페닐)안트라센의Of bis (pentadierterophenyl) anthracene 합성 synthesis

상기 실시예 1-2의 합성 생성물로부터 2,7-디페닐-9,10-비스(펜타듀테리오페닐)안트라센을 하기 반응식에 따라 합성하였다.2,7-diphenyl-9,10-bis (pentaduteriophenyl) anthracene was synthesized from the synthesis product of Example 1-2 according to the following scheme.

Figure 112008053423335-PAT00045
Figure 112008053423335-PAT00045

상기 반응을 살펴보면, 먼저 500ml 둥근바닥 플라스크에 상기 반응에서 수득한 2,7-디브로모-9,10-비스(펜타듀테리오페닐)안트라센 11.5 g (0.023 mol), 4-페닐보론산 (4-phenylboric acid) 8.4 g (0.069 mol), 탄산칼륨 10.4 g (0.076 mol), Pd(PPh3)4 1.4 g (0.001 mol), 물 40ml, 톨루엔 150ml 및 에탄올 40 ml를 넣고, 24 시간 동안 환류냉각하며 반응시켰다. 반응 종료 후, 반응 결과물을 상온으로 냉각한 후, 반응물을 여과한 뒤, 여액을 물을 사용하여 층분리하여 유기층을 분리하여 감압농축한 다음, 관크로마토그래피를 이용하여 분리하여, 본 발명에 따른 2,7-디페닐-9,10-비스(펜타듀테리오페닐)안트라센 4.8 g (수득률 42.0%)을 제조하였으며, 이에 대한 1H-NMR 그래프를 도 2에 나타내었다.In the reaction, first, 11.5 g (0.023 mol) of 2,7-dibromo-9,10-bis (pentaduteriophenyl) anthracene obtained in the reaction in a 500 ml round bottom flask, 4-phenylboronic acid ( 4-phenylboric acid) 8.4 g (0.069 mol), potassium carbonate 10.4 g (0.076 mol), Pd (PPh 3 ) 4 1.4 g (0.001 mol), 40 ml of water, 150 ml of toluene and 40 ml of ethanol were added and refluxed for 24 hours. The reaction was cooled. After the completion of the reaction, the reaction product was cooled to room temperature, the reaction product was filtered, the filtrate was separated by layering with water, the organic layer was separated and concentrated under reduced pressure, and then separated by tube chromatography, according to the present invention. 4.8 g (yield 42.0%) of 2,7-diphenyl-9,10-bis (pentaduteriophenyl) anthracene was prepared, and a 1 H-NMR graph thereof is shown in FIG. 2.

실시예Example 1-4 1-4

유기전계발광소자의Of organic light emitting device 제조 Produce

실시예 1-3의 반응생성물을 이용하여 유기전계발광소자를 하기의 방법에 따 라 제조하였다.Using the reaction product of Example 1-3, an organic light emitting display device was manufactured according to the following method.

먼저, ITO 글라스의 발광 면적이 2mm × 2mm가 되도록 기판 상에 패터닝한 다음 세정하였다. 상기 기판을 진공 챔버에 장착한 후, 베이스 압력이 1 × 10-6 torr가 되도록 한 다음, 공지의 방법을 사용하여, 상기 ITO 글라스 상에 CuPC (200Å), NPD (400Å), 실시예 1-3의 안트라센 유도체 + C545T(하기 화학식 3) (5%) (200Å), Alq3 (350Å), LiF (5Å), Al (1000Å)의 순서로 성막하였다. 제조된 유기전계발광소자의 발광특성은 0.4 mA/cm2에서 1,621 Cd/m2 (6.12 V), 수명은 335시간(T80)을 나타내었다.First, the light emitting area of the ITO glass was patterned on the substrate so as to be 2 mm x 2 mm, and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 −6 torr, and then CuPC (200 kPa), NPD (400 kPa), Example 1- was placed on the ITO glass using a known method. Anthracene derivative of 3 + C545T (Formula 3) (5%) (200 Pa), Alq 3 (350 Pa), LiF (5 Pa), Al (1000 Pa) in the order of the film. The luminescence properties of the fabricated organic electroluminescent device were 1,621 Cd / m 2 (6.12 V) at 0.4 mA / cm 2 and the lifetime was 335 hours (T 80 ).

Figure 112008053423335-PAT00046
Figure 112008053423335-PAT00046

실시예Example 2  2

9-9- 펜타듀테리오페닐Pentadutheriophenyl -10--10- 펜안스릴안트라센의Of pen anthryl anthracene 합성 및 이를 이용한  Synthesis and Using the Same 유기전계발광소자의Of organic light emitting device 제조 Produce

실시예Example 2-1 2-1

9-9- 펜타듀테리오페닐안트라센의Of pentaduteriophenylanthracene 합성 synthesis

9-펜타듀테리오페닐안트라센을 하기 반응식에 따라 합성하였다.9-Pentaduteriophenylanthracene was synthesized according to the following scheme.

Figure 112008053423335-PAT00047
Figure 112008053423335-PAT00047

상기 반응을 살펴보면, 먼저 500ml의 3-목 둥근바닥 플라스크에 상기 실시예 1-1에서 제조된 펜타듀테리오페닐보론산(phenyl Boric aicd) 9.6g(0.076mol), 9-브로모안트라센(9-Bromoanthracene) 15g(0.058g), 탄산칼륨 16.1g(0.117mol), Pd(PPh3)4 2.7g(0.002mol), 물 75ml, 톨루엔 150ml 및 에탄올150ml를 넣고 환류반응시켰다. 상기 반응 종료 후, 층 분리하여 수층은 제거하고 유기층을 감압 농축하여, 관크로마토그래피를 이용하여 펜타듀테리오페닐안트라센 13.6g(수득률 89.9%)을 수득하였다.Looking at the reaction, first pentaduteriophenyl boric acid (phenyl Boric aicd) prepared in Example 1-1 in a 500ml three-neck round bottom flask 9.6g (0.076mol), 9-bromoanthracene (9 15 g (0.058 g) of bromoanthracene, 16.1 g (0.117 mol) of potassium carbonate, 2.7 g (0.002 mol) of Pd (PPh 3 ) 4 , 75 ml of water, 150 ml of toluene and 150 ml of ethanol were added to reflux. After completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure, and 13.6 g (yield 89.9%) of pentaduteriophenylanthracene was obtained using tube chromatography.

실시예Example 2-2 2-2

9-9- 펜타듀테리오페닐Pentadutheriophenyl -10--10- 브로모안트라센의Bromoanthracene 합성 synthesis

9-펜타듀테리오페닐-10-브로모안트라센을 하기 반응식에 따라 합성하였다.9-Pentaduteriophenyl-10-bromoanthracene was synthesized according to the following scheme.

Figure 112008053423335-PAT00048
Figure 112008053423335-PAT00048

상기 반응을 살펴보면, 먼저 1L의 3-목 둥근바닥 플라스크에 상기 실시예 2-1에서 제조된 9-펜타듀테리오페닐안트라센 13.6g(0.052mol), 디클로로메탄 272ml를 넣고 상온에서 결정을 녹인 후, 0℃로 냉각한 후, Br2 10.1g (0.063mol)을 디클로로메탄 50ml에 희석시켜 천천히 투입하며 반응시켰다. 상기 반응 종료 후 층 분리하여 수층은 제거하고 유기층을 감압 농축하여, MeOH로 결정을 석출시킨 후 재결정하여 노란색의 9-페닐-10-브로모안트라센 결정 13.4g(수득률 75.5%)를 얻었다.Looking at the reaction, first, 13.6 g (0.052 mol) of 9-pentadiuteriophenylanthracene prepared in Example 2-1 and 272 ml of dichloromethane were dissolved in a 1 L three-neck round bottom flask, and the crystals were dissolved at room temperature. After cooling to 0 ° C., Br 2 10.1 g (0.063 mol) was diluted in 50 ml of dichloromethane and reacted slowly. After completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure, crystals were precipitated with MeOH, and recrystallized to obtain 13.4 g (yield 75.5%) of yellow 9-phenyl-10-bromoanthracene crystals.

실시예Example 2-3 2-3

9-9- 펜타듀테리오페닐Pentadutheriophenyl -10--10- 페난스릴안트라센의Of phenanthrylanthracene 합성 synthesis

9-펜타듀테리오페닐-10-페난스릴안트라센을 하기 반응식에 따라 합성하였다.9-Pentaduteriophenyl-10-phenanthrylanthracene was synthesized according to the following scheme.

Figure 112008053423335-PAT00049
Figure 112008053423335-PAT00049

상기 반응을 살펴보면, 500ml의 3-목 둥근바닥 플라스크에 상기 실시예 1-4에서 제조된 9-펜타듀테리오페닐-10-브로모안트라센 13.4g (0.040mol), 9-페난스렌보론산 14.3g (0.064mol), 탄산칼륨 22.2g(0.161mol), Pd(PPh3)4 2.3g(0.002mol), 물 26ml, 톨루엔 134ml 및 에탄올 134ml를 넣고 환류시켰다. 상기 반응 종료 후, 층 분리하여 수층은 제거하고 유기층을 감압 농축한 뒤 톨루엔으로 재결정하여 본 발명에 따른 9-펜타듀테리오페닐-10-페난스릴안트라센 9.2g(수득률 53.2%)을 제조하였으며, 이에 대한 1H-NMR 그래프를 도 3에 나타내었다.Looking at the reaction, in a 500 ml three-neck round bottom flask 93.4 pentaduteriophenyl-10-bromoanthracene prepared in Example 1-4 (0.040mol), 9-phenanthrenboronic acid 14.3 g (0.064 mol), 22.2 g (0.161 mol) of potassium carbonate, 2.3 g (0.002 mol) of Pd (PPh 3 ) 4 , 26 ml of water, 134 ml of toluene, and 134 ml of ethanol were refluxed. After completion of the reaction, the layers were separated, the aqueous layer was removed, the organic layer was concentrated under reduced pressure and recrystallized with toluene to prepare 9.2 g (yield 53.2%) of 9-pentadiuteriophenyl-10-phenanthrylanthracene according to the present invention. 1 H-NMR graph for this is shown in FIG. 3.

실시예Example 2-4 2-4

본 발명에 따른 According to the invention 유기전계발광소자의Of organic light emitting device 제조 Produce

실시예 1-3의 안트라센 유도체 대신 실시예 2-3의 안트라센 유도체를 사용하였다는 점, 도판트로서 C545T 대신에 하기 화학식 4의 1,6-디페닐아미노피렌을 사용하였다는 점을 제외하고는, 상기 실시예 1-4와 동일한 방법으로 유기전계발광소 자를 제조하였다. 제조된 유기전계발광소자의 발광특성은 0.4 mA/cm2에서 766 Cd/m2 (5.65 V), 수명은 494시간(T80)을 나타내었다.Anthracene derivatives of Examples 2-3 were used instead of the anthracene derivatives of Examples 1-3, except that 1,6-diphenylaminopyrene of Formula 4 was used instead of C545T as a dopant. In the same manner as in Example 1-4, an organic light emitting diode was manufactured. The luminescence properties of the fabricated organic electroluminescent device were 766 Cd / m 2 (5.65 V) at 0.4 mA / cm 2 , and the lifetime was 494 hours (T 80 ).

Figure 112008053423335-PAT00050
Figure 112008053423335-PAT00050

실시예Example 3 3

9-9- 펜타듀테리오페닐Pentadutheriophenyl -10--10- 피레닐안트라센의Pyrenylanthracene 합성 및 이를 이용한  Synthesis and Using the Same 유기전계발광Organic electroluminescence 소자의 제조Manufacture of device

실시예Example 3-1 3-1

9-9- 펜타듀테리오페닐Pentadutheriophenyl -10-(1--10- (1- 피레닐Pyrenyl )) 페닐안트라센의Of phenylanthracene 합성 synthesis

실시예 2-3의 반응에서 페난스렌 보론산 대신 피렌 보론산을 이용하여 9-펜타듀테리오페닐-10-(1-피레닐)페닐안트라센을 합성하였으며, 이에 대한 1H-NMR 그래프를 도 4에 나타내었다.In the reaction of Example 2-3, 9-pentaduteriophenyl-10- (1-pyrenyl) phenylanthracene was synthesized using pyrene boronic acid instead of phenanthrene boronic acid, and a 1 H-NMR graph for this is shown. 4 is shown.

실시예Example 3-2 3-2

본 발명에 따른 According to the invention 유기전계발광소자의Of organic light emitting device 제조 Produce

실시예 1-3의 안트라센 유도체 대신에 실시예 3-1의 안트라센 유도체를 사용하였다는 점과 도판트로서 C545T 대신에 하기 화학식 5의 화합물을 사용하였다는 점을 제외하고는, 상기 실시예 1-4와 동일한 방법에 따라서 유기전계발광소자를 제조하였다. 제조된 유기전계발광소자의 발광특성은 0.4 mA/cm2에서 852 Cd/m2 (5.10 V), 수명은 127시간(T80)을 나타내었다.Example 1- except that the anthracene derivative of Example 3-1 was used instead of the anthracene derivative of Examples 1-3 and the compound of Formula 5 was used instead of C545T as the dopant. An organic light emitting diode device was manufactured according to the same method as in Example 4. The luminescence properties of the fabricated organic electroluminescent device were 852 Cd / m 2 (5.10 V) at 0.4 mA / cm 2 , and the lifetime was 127 hours (T 80 ).

Figure 112008053423335-PAT00051
Figure 112008053423335-PAT00051

비교예Comparative example 1 One

종래기술에 따른 According to the prior art 유기전계발광소자의Of organic light emitting device 제조 Produce

실시예 1-3의 안트라센 유도체 대신에 2,7,9,10-테트라페닐안트라센을 사용하였다는 점을 제외하고는, 상기 실시예 1-4와 동일한 방법에 따라 유기전계발광소 자를 제조하였다. 제조된 유기전계발광소자의 발광특성은 0.4 mA/cm2에서 1,146 Cd/m2 (6.08 V), 수명은 250시간(T80)을 나타내었다.An organic light emitting diode was manufactured according to the same method as Example 1-4 except for using 2,7,9,10-tetraphenylanthracene instead of the anthracene derivative of Example 1-3. The luminescence properties of the fabricated organic electroluminescent device were 1,146 Cd / m 2 (6.08 V) at 0.4 mA / cm 2 , and the lifetime was 250 hours (T 80 ).

비교예Comparative example 2 2

종래기술에 따른 According to the prior art 유기전계발광소자의Of organic light emitting device 제조 Produce

실시예 2-3의 안트라센 유도체 대신에 9-페닐-10-펜안스릴안트라센을 사용하였다는 점을 제외하고는, 상기 실시예 2-4와 동일한 방법에 따라서 유기전계발광소자를 제조하였다. 제조된 유기전계발광소자의 발광특성은 0.4 mA/cm2에서 663 Cd/m2 (5.36 V), 수명은 296hr(T80)를 나타내었다.An organic light emitting display device was manufactured according to the same method as Example 2-4 except for using 9-phenyl-10-phenanthrylanthracene instead of the anthracene derivative of Example 2-3. The luminescence properties of the fabricated organic electroluminescent device were 663 Cd / m 2 (5.36 V) at 0.4 mA / cm 2 and the lifetime was 296 hr (T 80 ).

비교예Comparative example 3 3

종래기술에 따른 According to the prior art 유기전계발광소자의Of organic light emitting device 제조 Produce

실시예 3-1의 안트라센 유도체 대신에 9-페닐-10-(1-피레닐)페닐안트라센을 사용하였다는 점을 제외하고는, 상기 실시예 3-2와 동일한 방법에 따라서 유기전계발광소자를 제조하였다. 제조된 유기전계발광소자의 발광특성은 0.4 mA/cm2에서An organic light emitting display device was manufactured in the same manner as in Example 3-2, except that 9-phenyl-10- (1-pyrenyl) phenylanthracene was used instead of the anthracene derivative of Example 3-1. Prepared. The emission characteristics of the manufactured organic light emitting display device was 0.4 mA / cm 2

845 Cd/m2 (5.94 V), 수명은 108hr(T80)를 나타내었다.845 Cd / m 2 (5.94 V), lifetime was 108 hrs (T 80 ).

하기 표 1은 실시예 1, 2, 3 및 비교예 1, 2, 3에 따른 유기전계발광소자의 다양한 특성에 대한 비교 실험 결과이다.Table 1 below shows comparative test results for various characteristics of organic light emitting diodes according to Examples 1, 2, and 3 and Comparative Examples 1, 2 and 3.

Figure 112008053423335-PAT00052
Figure 112008053423335-PAT00052

표 1을 참조하면, 실시예 1, 2 및 3 따른 유기전계발광소자가 비교예 1, 2 및 3에 따른 유기전계발광소자에 비해서 전력효율 및 발광효율이 동등 이상이며, 특히 수명특성이 우수하다는 사실을 알 수 있다. 보다 이를 구체적으로 살펴보면, 동일한 구조에 수소 대신에 중수소의 치환기가 치환된 실시예 1, 2 및 3의 안트라센 유도체를 사용하는 유기전계발광소자가 수소 구조의 안트라센 유도체를 사용하는 유기전계발광소자인 비교예 1, 2, 3에 비하여 최소 123%(실시예 3) 최대 167%(실시예 2)까지 수명이 증가하는 것을 알 수 있다. 즉, 안트라센 유도체의 치환기를 중수소로 치환시킴으로써 동일하거나 향상된 전력효율을 유지하면서도, 매우 뛰어난 수명특성을 갖는 유기전계발광소자를 제조할 수 있는 본 발명은 종래의 기술에 따른 유기전계발광소자 재료에 비하여 매우 우수하다.Referring to Table 1, the organic light emitting display device according to Examples 1, 2 and 3 has the same or higher power efficiency and luminous efficiency than the organic light emitting display device according to Comparative Examples 1, 2 and 3, and particularly has excellent life characteristics. I can see the fact. More specifically, the organic electroluminescent device using the anthracene derivatives of Examples 1, 2 and 3 in which the deuterium substituent is substituted for hydrogen in the same structure is an organic electroluminescent device using the anthracene derivative of the hydrogen structure. It can be seen that the lifespan is increased by at least 123% (Example 3) and up to 167% (Example 2) compared to Examples 1, 2, and 3. That is, the present invention can manufacture an organic light emitting display device having a very excellent lifespan while maintaining the same or improved power efficiency by substituting the substituent of an anthracene derivative with deuterium, compared to the organic light emitting display device material according to the prior art. Very excellent.

도 1a 내지 1e는 본 발명의 바람직한 실시예에 따른 유기전계발광소자들의 적층 구조를 나타낸 단면도들이다.1A to 1E are cross-sectional views illustrating a laminated structure of organic light emitting diodes according to an exemplary embodiment of the present invention.

도 2는 실시예 1에서 제조된 본 발명에 따른 안트라센 유도체에 대한 1H-NMR 스펙트럼이다.2 is a 1 H-NMR spectrum of the anthracene derivative according to the present invention prepared in Example 1. FIG.

도 3은 실시예 2에서 제조된 본 발명에 따른 안트라센 유도체에 대한 1H-NMR 스펙트럼이다.3 is a 1 H-NMR spectrum of the anthracene derivative according to the present invention prepared in Example 2. FIG.

도 4는 실시예 3에서 제조된 본 발명에 따른 안트라센 유도체에 대한 1H-NMR 스펙트럼이다.4 is a 1 H-NMR spectrum of the anthracene derivative according to the present invention prepared in Example 3. FIG.

Claims (6)

하기 식 1의 안트라센 유도체:Anthracene derivative of Formula 1
Figure 112008053423335-PAT00053
(1)
Figure 112008053423335-PAT00053
(One) 상기 식에서 X1 내지 X10은 각각 독립적으로 수소 원자, 중수소 원자, 할로겐 원자, 탄소수 1 내지 10인 알킬실릴, 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 10 내지 60의 축합방향족환, 치환 또는 비치환된 스티릴기, 치환 또는 비치환된 아미노기, 치환 또는 비치환된 비닐기, 치환 또는 비치환된 카르보닐기, 치환 또는 비치환된 카르복실기, 치환 또는 비치환된 아릴치오기, 치환 또는 비치환된 탄소수 4 내지 40의 시클로알칸, 치환 또는 비치환된 탄소수 4 내지 20의 시클로알켄, 치환 또는 비치환된 탄소수 1 내지 60의 알콕시, 치환 또는 비치환된 탄소수 1 내지 60의 직쇄, 분기 또는 환상의 알킬기 또는 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 60의 아릴기 또는 탄소수 3 내지 40의 헤테로아릴기이며, Wherein X 1 to X 10 are each independently a hydrogen atom, a deuterium atom, a halogen atom, an alkylsilyl having 1 to 10 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted condensed aromatic ring having 10 to 60 carbon atoms, a substituted or Unsubstituted styryl group, substituted or unsubstituted amino group, substituted or unsubstituted vinyl group, substituted or unsubstituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted aryl group, substituted or unsubstituted carbon number 4 to 40 cycloalkane, substituted or unsubstituted cycloalkene having 4 to 20 carbon atoms, substituted or unsubstituted alkoxy having 1 to 60 carbon atoms, substituted or unsubstituted straight chain, branched or cyclic alkyl group having 1 to 60 carbon atoms or Each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms, 상기 치환된 알콕시, 직쇄, 분기 또는 환상의 알킬기, 아미노기, 비닐기, 카르보닐기, 카르복실기, 아릴치오기, 탄소수 4 내지 40의 시클로알칸 또는 탄소수 4 내지 20의 시클로알켄은 탄소수 1 내지 10의 알콕시기, 시아노기, 탄소수 1 내지 10의 알킬아미노기, 탄소수 1 내지 10의 알킬실릴기, 할로겐기, 탄소수 6 내지 10의 아릴기, 탄소수 6 내지 10의 아릴옥시기, 탄소수 6 내지 10의 아릴아미노기, 탄소수 6 내지 10의 아릴실릴기, 탄소수 3 내지 19의 헤테로아릴기 또는 수소로 이루어진 군으로부터 선택된 하나 이상의 치환기에 의해서 치환된 것이며, Substituted Alkoxy, straight chain, branched or cyclic alkyl group, amino group, vinyl group, carbonyl group, carboxyl group, aryl group, cycloalkane having 4 to 40 carbon atoms or cycloalkene having 4 to 20 carbon atoms, alkoxy group having 1 to 10 carbon atoms, cyano group, C1-C10 alkylamino group, C1-C10 alkylsilyl group, halogen group, C6-C10 aryl group, C6-C10 aryloxy group, C6-C10 arylamino group, C6-C10 Is substituted by one or more substituents selected from the group consisting of an arylsilyl group, a heteroaryl group having 3 to 19 carbon atoms or hydrogen, 상기 치환된 탄소수 6 내지 60의 아릴기, 탄소수 3 내지 40의 헤테로아릴기, 탄소수 10 내지 60의 축합방향족환 또는 스티릴기는 수소 원자, 중수소 원자, 할로겐 원자, 탄소수 1 내지 10인 알킬실릴, 탄소수 1 내지 20의 알킬기, 탄소수 1 내지 10의 알콕시기, 시아노기, 탄소수 1 내지 10의 알킬아미노기, 탄소수 1 내지 10의 알킬실릴기, 할로겐기, 탄소수 6 내지 10의 아릴기, 탄소수 6 내지 10의 아릴옥시기, 탄소수 6 내지 10의 아릴아미노기, 탄소수 6 내지 10의 아릴실릴기, 탄소수 3 내지 19의 헤테로아릴기로 이루어진 군으로부터 선택된 하나 이상의 치환기에 의해서 치환된 것이고, 상기 치환체는 각각 독립적으로 인접하는 그룹과 결합하여 환을 형성할 수 있으며,The substituted aryl group having 6 to 60 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, condensed aromatic ring having 10 to 60 carbon atoms, or styryl group is hydrogen atom, deuterium atom, halogen atom, alkyl silyl having 1 to 10 carbon atoms, carbon number An alkyl group of 1 to 20 carbon atoms, an alkoxy group of 1 to 10 carbon atoms, a cyano group, an alkylamino group of 1 to 10 carbon atoms, an alkylsilyl group of 1 to 10 carbon atoms, a halogen group, an aryl group of 6 to 10 carbon atoms, and a 6 to 10 carbon atoms One or more substituents selected from the group consisting of an aryloxy group, an arylamino group having 6 to 10 carbon atoms, an arylsilyl group having 6 to 10 carbon atoms, and a heteroaryl group having 3 to 19 carbon atoms, each of which is independently adjacent Can combine with groups to form rings, 여기에서 X1 내지 X10 중 적어도 어느 하나 이상은 중수소에 의하여 치환된 탄소수 6 내지 60의 아릴기 또는 탄소수 3 내지 40의 헤테로아릴기임.Wherein at least one of X 1 to X 10 is an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms substituted with deuterium. 제 1항에 있어서, 식 1의 X2, X7, X5 및 X10 중 적어도 어느 하나 이상은
Figure 112008053423335-PAT00054
인 것을 특징으로 하는 안트라센 유도체.The method of claim 1, wherein at least one of X2, X7, X5, and X10 of Formula 1 is
Figure 112008053423335-PAT00054
Anthracene derivatives, characterized in that. 제 1항에 있어서, 상기 안트라센 유도체는 하기 식으로부터 선택되는 구조를 갖는 것을 특징으로 하는 안트라센 유도체.The anthracene derivative according to claim 1, wherein the anthracene derivative has a structure selected from the following formula. _
Figure 112008053423335-PAT00055
Figure 112008053423335-PAT00056
Figure 112008053423335-PAT00057
Figure 112008053423335-PAT00058
_
Figure 112008053423335-PAT00055
Figure 112008053423335-PAT00056
Figure 112008053423335-PAT00057
Figure 112008053423335-PAT00058
Figure 112008053423335-PAT00059
Figure 112008053423335-PAT00059
Figure 112008053423335-PAT00060
Figure 112008053423335-PAT00060
Figure 112008053423335-PAT00061
Figure 112008053423335-PAT00061
Figure 112008053423335-PAT00062
Figure 112008053423335-PAT00062
Figure 112008053423335-PAT00063
Figure 112008053423335-PAT00063
Figure 112008053423335-PAT00064
Figure 112008053423335-PAT00065
Figure 112008053423335-PAT00066
Figure 112008053423335-PAT00064
Figure 112008053423335-PAT00065
Figure 112008053423335-PAT00066
Figure 112008053423335-PAT00067
Figure 112008053423335-PAT00068
Figure 112008053423335-PAT00069
Figure 112008053423335-PAT00070
Figure 112008053423335-PAT00067
Figure 112008053423335-PAT00068
Figure 112008053423335-PAT00069
Figure 112008053423335-PAT00070
Figure 112008053423335-PAT00071
Figure 112008053423335-PAT00071
Figure 112008053423335-PAT00072
Figure 112008053423335-PAT00073
Figure 112008053423335-PAT00074
Figure 112008053423335-PAT00075
Figure 112008053423335-PAT00072
Figure 112008053423335-PAT00073
Figure 112008053423335-PAT00074
Figure 112008053423335-PAT00075
Figure 112008053423335-PAT00076
Figure 112008053423335-PAT00077
Figure 112008053423335-PAT00076
Figure 112008053423335-PAT00077
Figure 112008053423335-PAT00078
Figure 112008053423335-PAT00079
Figure 112008053423335-PAT00078
Figure 112008053423335-PAT00079
Figure 112008053423335-PAT00080
Figure 112008053423335-PAT00081
Figure 112008053423335-PAT00080
Figure 112008053423335-PAT00081
Figure 112008053423335-PAT00082
Figure 112008053423335-PAT00083
Figure 112008053423335-PAT00084
Figure 112008053423335-PAT00085
Figure 112008053423335-PAT00082
Figure 112008053423335-PAT00083
Figure 112008053423335-PAT00084
Figure 112008053423335-PAT00085
Figure 112008053423335-PAT00086
Figure 112008053423335-PAT00086
Figure 112008053423335-PAT00087
Figure 112008053423335-PAT00087
Figure 112008053423335-PAT00088
Figure 112008053423335-PAT00088
Figure 112008053423335-PAT00089
Figure 112008053423335-PAT00089
Figure 112008053423335-PAT00090
Figure 112008053423335-PAT00090
 애노드; Anode; 캐소드; 및 Cathode; And 상기 애노드 및 캐소드 사이에 개재되며, 청구항 1 내지 3의 안트라센 유도체를 포함하는 층을 구비한 유기전계발광소자.An organic electroluminescent device having a layer interposed between the anode and the cathode and comprising the anthracene derivative of claims 1 to 3. 제 4항에 있어서, 상기 유기전계발광소자는 상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 정공저지층, 전자수송층, 전자주입층 및 전자저지층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 4, wherein the organic light emitting device further comprises at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer and an electron blocking layer between the anode and the cathode. An organic light emitting display device, characterized in that. 제 4항에 있어서, 상기 안트라센 유도체를 포함하는 층은 발광층인 것을 특징으로 하는 유기전계발광소자.The organic light emitting device of claim 4, wherein the layer including the anthracene derivative is a light emitting layer.
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