WO2019078443A1 - Novel compound and organic light emitting device using same - Google Patents

Novel compound and organic light emitting device using same Download PDF

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WO2019078443A1
WO2019078443A1 PCT/KR2018/006423 KR2018006423W WO2019078443A1 WO 2019078443 A1 WO2019078443 A1 WO 2019078443A1 KR 2018006423 W KR2018006423 W KR 2018006423W WO 2019078443 A1 WO2019078443 A1 WO 2019078443A1
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oav
czl7900
8lozam
6ϊοζ
compound
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PCT/KR2018/006423
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하재승
김연환
이성재
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주식회사 엘지화학
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Priority claimed from KR1020180062161A external-priority patent/KR102109789B1/en
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Priority to CN201880018312.1A priority Critical patent/CN110494430B/en
Publication of WO2019078443A1 publication Critical patent/WO2019078443A1/en

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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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
    • C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
    • 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
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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

Abstract

The present invention provides a novel compound and an organic light emitting device using the same.

Description

【발명의 명칭】  Title of the Invention
신규한 화합물 및 이를 이용한유기발광 소자  Novel compounds and organic light emitting devices using the same
【기술분야】 TECHNICAL FIELD
관련 출원 (들)과의 상호 인용  Cross-reference with related application (s)
본 출원은 2017년 10월 19일자 한국 특허 출원 제 10— 2017-0135923호 및 2018년 5월 30일자 한국 특허 출원 게 10-2018-0062161호에 기초한 우선권의 이익을 주장하며， 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다. 본 발명은 신규한 아민계 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.  This application claims the benefit of priority based on Korean Patent Application No. 10-2017-0135923, dated October 19, 2017, and Korean Patent Application No. 10-2018-0062161, dated May 30, 2018, The entire contents of which are incorporated herein by reference. The present invention relates to a novel amine compound and an organic light emitting device comprising the same.
【배경기술】  BACKGROUND ART [0002]
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각， 우수한 콘트라스트, 빠른 웅답 시간을 가지며， 휘도， 구동 전압 및 웅답 속도 특성이 우수하여 많은 연구가 진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층， 정공수송층， 발광층, 전자수송층， 전자주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이， 음극에서는 전자가 유기물층에 주입되게 되고， 주입된 정공과 전자가 만났을 때 액시톤 (exci ton)이 형성되며， 이 액시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다.. 상가와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다. 【선행기술문헌】 In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of brightness, driving voltage, and response speed, and much research is proceeding. The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. The organic material layer may have a multilayer structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, and an exciton is formed when the injected holes and electrons meet each other. And the light is emitted when the axiton falls back to the ground state. Development of a new material for organic materials used in organic light emitting devices such as a shop is continuously required. [Prior Art Document]
【특허문헌】  [Patent Literature]
(특허문헌 0001) 한국특허 공개번호 제 10-2000-0051826호  (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826
【발명의 내용】  DISCLOSURE OF THE INVENTION
【해결하려는 과제】  [Problem to be solved]
본 발명은 신규한 아민계 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.  The present invention relates to a novel amine compound and an organic light emitting device comprising the same.
【과제의 해결 수단】  MEANS FOR SOLVING THE PROBLEMS
본 발명은  The present invention
본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다:  The present invention provides a compound represented by the following formula (1): < EMI ID =
Figure imgf000003_0001
Figure imgf000003_0001
상기 화학식 1에서  In Formula 1,
Xi 내지 X4 중, 및 ¾， ¾ 및 ¾ 또는 ¾ 및 가 하기 화학식 2의 각각 연결되고, 나머지는 수소이고，  And Xi, X4 and X4, X4 and X4 or X4 are respectively linked with the following formula (2)
Figure imgf000003_0002
Figure imgf000003_0002
a , c , d 및 e는 0 내지 3의 정수이고  a, c, d and e are an integer of 0 to 3
b는 0 내지 2의 정수이고，  b is an integer of 0 to 2,
X는 1 또는 2이고  X is 1 or 2
Ri 내지 ¾는 각각 독립적으로 수소， 중수소， 할로겐， 시아노， 치환 또는 비치환된 (^60 알킬 , 치환 또는 비치환된 알콕시 , 치환 또는 비치환된 ( 60 티오알킬 , 치환 또는 비치환된 C3-60 사이클로알킬， 치환 또는 비치환된 C6-60 아릴， 또는 트리 (d-60 알킬)실릴이고， R 1 to R 4 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C 60 alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted ( 60 thioalkyl, substituted or unsubstituted C 3 - 60 cycloalkyl, substituted or Unsubstituted C 6 -60 aryl, or tri (d-60 alkyl) silyl,
R은 각각 독립적으로 하기 화학식 3으로 표시되고  R are each independently represented by the following formula
[화학식 3]  (3)
L3 L 3
Ar2 Ar 2
상기 화학식 3에서，  In Formula 3,
Li, 및 L3는 각각 독립적으로， 단일 결합; 치환 또는 비치환된 C6- 60 아릴렌; 또는 치환 또는 비치환된 N, 0, 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴렌이고，Li, and L < 3 > each independently represent a single bond; Substituted or unsubstituted C 6 - 60 arylene; Or substituted or unsubstituted C 2 - 60 heteroarylene containing at least one hetero atom selected from the group consisting of N, O, and S,
An 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, 0， 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이다. 또한， 본 발명은 게 1 전극; 상기 게 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 게 2 전극 사이에 구바된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는， 유기 발광 소자를 제공한다. An and Ar 2 are each C independently represents a substituted or unsubstituted 6-60 aryl; Or substituted or unsubstituted C 2 -C 60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O, and S. The present invention also provides a display device comprising: a first electrode; A second electrode facing the first electrode; And at least one organic material layer sandwiched between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 do.
【발명의 효과】  【Effects of the Invention】
상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며， 유기 발광 소자에서 효율의 향상， 낮은 구동전압 및 /또는 수명 특성을 향상시킬 수 있다. 특히， 상술한 화학식 1로 표시되는 화합물은 정공주입, 정공수송， 정공주입 및 수송， 발광， 전자수송， 또는 전자주입 재료로사용될 수 있다.  The compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device. In particular, the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting material.
【도면의 간단한 설명】 ' [Brief Description of Drawings] '
도 1은 기판 (1)， 양극 (2) , 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.  Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
도 2는 기판 (1)， 양극 (2) , 정공주입층 (5)， 정공수송층 (6)， 발광층 (7)， 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도사한 것이다. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is good.
【발명을 실시하기 위한 구체적인 내용】  DETAILED DESCRIPTION OF THE INVENTION
이하， 본 발명의 이해를 돕기 위하여 보다상세히 설명한다. 본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다.  Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention. The present invention provides a compound represented by the above formula (1).
본 명세서에서，
Figure imgf000005_0001
또 다른 치환기에 연결되는 결합을 의미한다. 본 명세서에서 "치환 또는 비치환된'' 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N , 0 및 S 원자 중 1개 이상을 포함하는 헤테로고리기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나， 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대， "2 이상의 치환기가 연결된 치환기 "는 비페닐기일 수 있다. 즉, 비페닐기는 아릴기일 수도 있고， 2개의 페닐기가 연결된 치환기로 해석될 수 있다. 본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다. In the present specification,
Figure imgf000005_0001
Means a bond connected to another substituent. The term " substituted or unsubstituted ", as used herein, refers to a substituent selected from the group consisting of deuterium, halogen group, nitrile group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, An aryloxy group, an aryloxy group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamine group, An arylamine group, an arylphosphine group, or a heterocyclic group containing at least one of N, O and S atoms, or may be substituted or unsubstituted with at least one substituent selected from the group consisting of N, O and S atoms, The substituent group to which at least two substituents are connected " may be a biphenyl group, i.e., the biphenyl group may be an aryl group. And the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, a compound having the following structure may be used. It is not.
Figure imgf000006_0001
본 명세서에 있어서， 에스테르기는 에스테르기의 산소가 탄소수 1 내지 25의 직쇄， 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 25의 아릴기로 치환될 수 있다. 구체적으로， 하기 구조식의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다.
Figure imgf000006_0001
In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
Figure imgf000006_0002
본 명세서에 있어서， 이미드가의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나, 이에 한정되는 것은 아니다.
Figure imgf000006_0002
In the present specification, the number of carbon atoms of the imide is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
Figure imgf000006_0003
본 명세서에 있어서， 실릴기는 . 구체적으로 트리메틸실릴기， 트리에틸실릴기, t-부틸디메틸실릴기， 비닐디메틸실릴기， 프로필디메틸실릴기， 트리페닐실릴기， 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 붕소기는 구체적으로 트리메틸붕소기， 트리에틸븡소기， t_부틸디메틸붕소기， 트리페닐붕소기 , 페닐붕소기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 할로겐기의 예로는 불소， 염소， 브롬 또는 요오드가 있다. 본 명세서에 있어서， 상기 알킬기는 직쇄 또는 분지쇄일 수 있고， 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸， 에틸， 프로필， n-프로필， 이소프로필， 부틸， n-부틸， 이소부틸， tert-부틸, sec-부틸， 1-메틸-부틸， 1ᅳ에틸—부틸， 펜틸， n-펜틸, 이소펜틸， 네오펜틸, tert—펜틸 핵실, n—핵실， 1-메틸펜틸， 2-메틸펜틸， 4-메틸 -2-펜틸， 3 , 3-디메틸부틸, 2-에틸부틸， 헵틸， n—헵틸， 1ᅳ메틸핵실, 사이클로펜틸메틸,사이클로핵틸메틸， 옥틸， n-옥틸， tert-옥틸, 1-메틸헵틸， 2-에틸핵실， 2-프로필펜틸， n-노닐， 2 , 2-디메틸헵틸， 1-에틸-프로필, 1 , 1- 디메틸-프로필， 이소핵실， 2-메틸펜틸， 4-메틸핵실， 5-메틸핵실 등이 있으나， 이들에 한정되지 않는다. 본 명세서에 있어서， 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나， 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐， 이소프로페닐， 1-부테닐， 2-부테닐， 3-부테닐， 1-펜테닐, 2-펜테닐， 3-펜테닐， 3-메틸— 1-부테닐， 1， 3-부타디에닐， 알릴， 1-페닐비닐 -1-일, 2-페닐비닐 -1-일， 2 , 2-디페닐비닐 -1-일， 2-페닐 -2- (나프틸 -1-일)비닐 -1-일， 2 , 2-비스 (디페닐 -1-일)비닐 -1-일， 스틸베닐기， 스티레닐기 등이 있으나 이들에 한정되지 않는다. 본 명세서에 있어서， 사이클로알킬기는 특별히 한정되지 않으나， 탄소수 3 내지 60인 것이 바람직하며， 일 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필， 사이클로부틸， 사이클로펜틸, 3-메틸사이클로펜틸， 2 , 3- 디메틸사이클로펜틸， 사이클로핵실， 3-메틸사이클로핵실， 4- 메틸사이클로핵실， 2 , 3-디메틸사아클로핵실， 3， 4， 5-트리메틸사이클로핵실， 4-tert-부틸사이클로핵실， 사이클로헵틸， 사이클로옥틸 등이 있으나， 이에 한정되자 않는다. 본 명세서에 있어서， 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며， 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 30이다. 일 실사상태에 따르면， 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 ： 단환식 아릴기로는 페닐기， 바이페닐기， 터페닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기， 안트라세닐기， 페난트릴기， 파이레닐기， 페릴레닐기， 크라이세닐기， 플루오레닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 본 명세서에 있어서， 플루오레닐기는 치환될 수 있고， 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 치환되는 경우，
Figure imgf000009_0001
등이 될 수 있다. 다만， 이에 한정되는 것은 아니다. 본 명세서에 있어서, 헤테로고리기는 이종 원소로 0 , N , Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서， 탄소수는 특별히 한정되지 않으나， 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기， 퓨란기, 피롤기， 이미다졸기， 티아졸기， 옥사졸기， 옥사디아졸기， 트리아졸기, 피리딜기， 비피리딜기.， 피리미딜기， 트리아진기， 아크리딜기， 피리다진기， 피라지닐기， 퀴놀리닐기， 퀴나졸린기， 퀴녹살리닐기， 프탈라지닐기， 피리도 피리미디닐기, 피리도 피라지닐기， 피라지노 피라지닐기， 이소퀴놀린기， 인돌기， 카바졸기， 벤조옥사졸기， 벤조이미다졸기， 벤조티아졸기， 벤조카바졸기， 벤조티오펜기, 디벤조티오펜기， 벤조퓨라닐기， 페난쓰롤린기 (phenanthrol ine) , 이소옥사졸릴기， 티아디아졸릴기， 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나， 이들에만 한정되는 것은 아니다. 본 명세서에 있어서, 아르알킬기， 아르알케닐기， 알킬아릴기， 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서， 아르알킬기, 알킬아릴기， 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서， 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서， 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 탄화수소 고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 헤테로고리는 1가기가 아니고, 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 상기 화학식 1에서， 화학식 2의 결합 위치에 따라, 상기 화학식 1은 각각 하기 화학식 1-1， 1-2 , 또는 1-3으로 표시된다.
Figure imgf000006_0003
In the present specification, a silyl group is a silyl group. Specific examples include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto. In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine. In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- Pentyl, neopentyl, tert-pentyl, n-butyl, 1-methylpentyl, 2-methylpentyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like. In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, 1, 3-butadienyl, allyl, 1-yl, 2-phenylvinyl-1-yl, 2-phenyl-2- (naphthyl- (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, styrenyl, and the like. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, , 4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like. In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to the monocyclic state, the number of carbon atoms of the aryl group is 6 to 20. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, and the like. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group. In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
Figure imgf000009_0001
And the like. However, the present invention is not limited thereto. In the present specification, the heterocyclic group is a heterocyclic group containing at least one of 0, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, an isoquinoline group, an indole group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, an isoquinoline group, A benzofuranyl group, a phenanthroline group, an isoxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzothiazole group, a benzothiazole group, a benzothiophene group, a dibenzothiophene group, Thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but are not limited thereto. In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group. In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent hydrocarbon ring, and the hydrocarbon ring is not a monovalent hydrocarbon ring, Can be applied. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other. In Formula 1, Formula 1 is represented by Formula 1-1, 1-2, or 1-3 according to the bonding position of Formula 2, respectively.
[화학식 1-1]  [Formula 1-1]
Figure imgf000010_0001
Figure imgf000010_0001
[화학식 1-3] [Formula 1-3]
Figure imgf000011_0001
바람직하게는， a, b , c , d 및 e는 0이다. 또한 바람직하게는, ^ 내지 R5는 수소이다. 바람직하게는, 은 단일 결합, 페닐렌 비페닐디일， 터페닐디일， 쿼터페닐디일， 나프탈렌디일 안트라센디일， 페난쓰렌디일， 트리페닐렌디일， 피렌디일， 디메틸플루오렌디일, 메틸페닐플루오렌디일， 디페닐플루오렌디일， 디벤조퓨란디일, 다벤조티오펜디일， 카바졸디일, 또는 9-페닐 -9H- 카바졸디일이다. 보다 바람직하게는， L1은 단일 결합， 또는 페닐렌이다. 바람직하게는， L2 및 L3은 각각 독립적으로 단일 결합， 페닐렌， 비페닐디일, 터페닐디일， 쿼터페닐디일， 나프탈렌디일， 안트라센디일， 페난쓰렌디일， 트리페닐렌디일, 피렌디일, 디메틸플루오렌디일， 메틸페닐플루오렌디일， 디페닐플루오렌디일, 스피로플루오렌디일， 디벤조퓨란디일, 디벤조티오펜디일， 카바졸디일， 또는 9-페닐— 9H- 카바졸디일이다. 바람직하게는， A 및 Ar2는 각각 독립적으로 페닐， 비페닐릴, 터페닐릴， 쿼터페닐릴, 나프틸， 페난쓰레닐, 디메틸플루오레닐， 디벤조플루오레닐， 스피로플루오레닐, . 디벤조퓨라닐， 디벤조티오페닐， 카바졸릴， 또는 9-페닐 -9H-카바졸릴이다. 상기 화학식 1로 표시되는 화합물의 대표적인 예는 다음과 같다: II
Figure imgf000011_0001
Preferably, a, b, c, d and e are zero. In addition, preferably, ^ to R 5 it is hydrogen. Preferably, the silver is selected from the group consisting of a single bond, phenylene biphenyl diyl, terphenyl diyl, quaterphenyl diyl, naphthalenediyl anthracenediyl, phenanthrenediyl, triphenylene diyl, pyrandiyl, dimethylfluorenediyl, methylphenylfluorenediyl, di Phenylfluorenediyl, dibenzofuranediyl, dibenzothiophenediyl, carbazolyl, or 9-phenyl-9H-carbazolyl. More preferably, L1 is a single bond, or phenylene. Preferably, L < 2 > and L < 3 > are each independently selected from the group consisting of a single bond, phenylene, biphenyl diyl, terphenyl diyl, quaterphenyl diyl, naphthalenediyl, anthracenediyl, phenanthrenyl, triphenylene diyl, Phenyl-9H-carbazolyl, fluorenylidene, methylphenylfluorenediyl, diphenylfluorenediyl, spirofluorenediyl, dibenzofuranediyl, dibenzothiophenediyl, carbazolyl, or 9-phenyl-9H-carbazolyl. Preferably, A and Ar 2 are each independently phenyl, biphenylyl, terphenyl reel, quarter-biphenylyl, naphthyl, phenanthryl waste carbonyl, dimethyl-fluorenyl, dibenzofuran fluorenyl, spiro fluorenyl. Dibenzofuranyl, dibenzothiophenyl, carbazolyl, or 9-phenyl-9H-carbazolyl. Representative examples of the compound represented by the above formula (1) are as follows: II
Figure imgf000012_0001
Figure imgf000012_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000013_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000013_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV ετ CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV ετ
Figure imgf000014_0001
Figure imgf000014_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV n £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV n
Figure imgf000015_0001
Figure imgf000015_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 91 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 91
Figure imgf000016_0001
91
Figure imgf000016_0001
91
Figure imgf000017_0001
Figure imgf000017_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV LI CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV LI
Figure imgf000018_0001
Figure imgf000018_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 81 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 81
Figure imgf000019_0001
61
Figure imgf000019_0001
61
Figure imgf000020_0001
Figure imgf000020_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000021_0001
Figure imgf000021_0001
CZl7900/8lOZaM/X3d
Figure imgf000022_0001
CZl7900 / 8lOZaM / X3d
Figure imgf000022_0001
Figure imgf000022_0002
Figure imgf000022_0002
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000023_0001
Figure imgf000023_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000024_0001
Figure imgf000024_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000025_0001
Figure imgf000025_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000026_0001
Figure imgf000026_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 9Z CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 9Z
Figure imgf000027_0001
Figure imgf000027_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV LZ CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV LZ
Figure imgf000028_0001
Figure imgf000028_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 8Z CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 8Z
Figure imgf000029_0001
Figure imgf000029_0001
£1?ΐ78Ζ.0/6ΐ0Ζ OAV 6Z £ 1? Ϊ́78ZD.0 / 6ΐ0Ζ OAV 6Z
Figure imgf000030_0001
Figure imgf000030_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV oe CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV oe
Figure imgf000031_0001
Figure imgf000031_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000032_0001
Figure imgf000032_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000033_0001
Figure imgf000033_0001
CZl7900/8lOZaMX3d Cl7f8Z.0/6l0Z OW εε CZl7900 / 8lOZaMX3d Cl7f8Z.0 / 6l0Z OW εε
Figure imgf000034_0001
Figure imgf000034_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000035_0001
Figure imgf000035_0001
£ 8Z.0/6l0i OAV £ 8Z.0 / 6l0i OAV
Figure imgf000036_0001
Figure imgf000036_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 9ε CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 9?
Figure imgf000037_0001
Figure imgf000037_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV ze £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV ze
Figure imgf000038_0001
Figure imgf000038_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV 8C £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV 8C
Figure imgf000039_0001
Figure imgf000039_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 6ε CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 6ε
Figure imgf000040_0001
Figure imgf000040_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000041_0001
Figure imgf000041_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV If CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV If
Figure imgf000042_0001
Figure imgf000042_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000043_0001
Figure imgf000043_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000044_0001
Figure imgf000044_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000045_0001
Figure imgf000045_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV 9 £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV 9
Figure imgf000046_0001
Figure imgf000046_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV  CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 
Figure imgf000047_0001
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000048_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 8t CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 8t
Figure imgf000049_0001
Figure imgf000049_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000050_0001
Figure imgf000050_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV OS CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV OS
Figure imgf000051_0001
Figure imgf000051_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 19 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 19
Figure imgf000052_0001
Figure imgf000052_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000053_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000053_0001
Figure imgf000054_0001
Figure imgf000054_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 9 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 9
Figure imgf000055_0001
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000056_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 99 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 99
Figure imgf000057_0001
Figure imgf000057_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000058_0001
Figure imgf000058_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000059_0001
Figure imgf000059_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 6S CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 6S
Figure imgf000060_0001
Figure imgf000060_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 09 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 09
Figure imgf000061_0001
Figure imgf000061_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 19 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 19
Figure imgf000062_0001
Figure imgf000062_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV Z9 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Z9
Figure imgf000063_0001
Figure imgf000063_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV S9 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV S9
Figure imgf000064_0001
Figure imgf000064_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000065_0001
Figure imgf000065_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000066_0001
Figure imgf000066_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000067_0001
Figure imgf000067_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000068_0001
Figure imgf000068_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000069_0001
Figure imgf000069_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000070_0001
Figure imgf000070_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV OL CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV OL
Figure imgf000071_0001
Figure imgf000071_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV IL CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV IL
Figure imgf000072_0001
Figure imgf000072_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV ZL CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV ZL
Figure imgf000073_0001
Figure imgf000073_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV ZL CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV ZL
Figure imgf000074_0001
Figure imgf000074_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000076_0001
Figure imgf000076_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000077_0001
Figure imgf000077_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000078_0001
Figure imgf000078_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000079_0001
Figure imgf000079_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000080_0001
Figure imgf000080_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 08 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 08
Figure imgf000081_0001
Figure imgf000081_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 18 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 18
Figure imgf000082_0001
Figure imgf000082_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000083_0001
Figure imgf000083_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV S8 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV S8
Figure imgf000084_0001
Figure imgf000084_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 8 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 8
Figure imgf000085_0001
Figure imgf000085_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV S8 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV S8
Figure imgf000086_0001
Figure imgf000086_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000087_0001
Figure imgf000087_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV Z,8 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Z, 8
Figure imgf000088_0001
Figure imgf000088_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000089_0001
Figure imgf000089_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 68 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 68
Figure imgf000090_0001
Figure imgf000090_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000091_0001
Figure imgf000091_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 16 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 16
Figure imgf000092_0001
Figure imgf000092_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV Z6 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Z6
Figure imgf000093_0001
Figure imgf000093_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000094_0001
Figure imgf000094_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 6 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 6
Figure imgf000095_0001
Figure imgf000095_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000096_0001
Figure imgf000096_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000097_0001
Figure imgf000097_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000098_0001
Figure imgf000098_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000099_0001
Figure imgf000099_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 66 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 66
Figure imgf000100_0001
Figure imgf000100_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 001 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 001
Figure imgf000101_0001
Figure imgf000101_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000102_0001
Figure imgf000102_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000103_0001
Figure imgf000103_0002
Figure imgf000103_0001
Figure imgf000103_0002
Figure imgf000103_0003
Figure imgf000103_0004
Figure imgf000103_0003
Figure imgf000103_0004
CZl7900/8lOZaM/X3d εοι CZl7900 / 8lOZaM / X3d εοι
Figure imgf000104_0001
Figure imgf000104_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000105_0001
Figure imgf000105_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 901 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 901
Figure imgf000106_0001
Figure imgf000106_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000107_0001
반웅식 1과 같은 제조 방법으로 제조할 수 있으며， 나머지 화학식 1-2 및 1-3으로 표시되는 화합물에도 적용할 수 있다. CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000107_0001
Can be prepared by the same production method as in the above-mentioned formula (1), and the compounds represented by the other formulas (1-2) and (1-3) can also be applied.
[반웅식 1]  However,
Figure imgf000108_0001
Figure imgf000108_0001
상기 반응식 1은 아민 치환 반웅으로서， 상기 화학식 1-a로 표시되는 화합물과 상기 화학식 1-b로 표시되는 화합물을 반웅시켜, 상기 화학식 1- 1로 표시되는 화합물을 제조하는 반웅이다. 상기 반웅은 팔라듐 촉매와 염기 존재하에 수행하는 것이 바람직하며， 아민 치환 반웅을 위한 반웅기는 당업계에 알려진 바에 따라 변경이 가능하다. 바람직하게는， 상기 X는 할로겐 (보다 바람직하게는， 브로모， 또는 클로로)이다. 상기 제조 방법은 후술할 제조예에서 보다구체화될 수 있다. 또한， 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로， 본 발명은 제 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다. 본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대， 본 발명의 유기 발광 소자는 유기물 층으로서 정공주입층, 정공수송층, 발광층, 전자수송층， 전자주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다. 또한， 상기 유기물 층은 정공주입층, 정공수송층, 또는 정공 주입과 수송을 동시에 하는 충을 포함할 수 있고, 상기 정공주입층， 정공수송층， 또는 정공 주입과 수송을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한, 상기 유기물 층은 발광층을 포함할 수 있고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. 특히， 본 발명에 따른 화합물은 발광층의 도편트로 사용할 수 있다. 또한, 상기 유기물 층은 전자수송층， 또는 전자주입층을 포함할 수 있고， 상기 전자수송층， 또는 전자주입층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한， 상기 전자수송층， 전자주입층， 또는 전자수송 및 전자주입을 동시에 하는 층은 상기 화학식 1로 표시되는 화합물을 포함한다. 또한， 상기 유기물 층은 발광층 및 전자수송층을 포함하고， 상기 전자수송층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 또한， 본 발명에 따른 유기 발광 소자는， 기판 상에 양극， 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조 (normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극， 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조 ( inverted type)의 유기 발광 소자일 수 있다. 예컨대， 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다. 도 1은 기판 ( 1)， 양극 (2)， 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것아다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 도 2는 기판 (1)， 양극 (2) , 정공주입층 (5)， 정공수송층 (6)， 발광층 (7)， 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 정공주입층， 정공수송층， 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 본 발명에 따른 유기 발광 소자는， 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한， 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우， 상기 유기물충은 동일한 물질 또는 다른 물질로 형성될 수 있다. 예컨대， 본 발명에 따른 유기 발광 소자는 기판 상에 제 1 전극， 유기물층 및 게 2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때, 스퍼터링법 (sputter ing)이나 전자범 증발법 (e-beam evaporat ion)과 같은 PVD(phys ical Vapor Deposi t ion)방법을 이용하여， 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층， 정공 수송층， 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후， 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도， 기판 상에 음극 물질부터 유기물층， 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한， 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코됩, 딥코팅， 닥터 블레이딩， 잉크젯 프린팅 스크린 프린팅， 스프레이법， 를 코팅 등을 의미하지만， 이들만으로 한정되는 것은 아니다. 이와 같은 방법 외에도， 기판 상에 음극 물질로부터 유기물층， 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다 (W0 2003/012890) . 다만, 제조 방법이 이에 한정되는 것은 아니다. 일례로, 상기 제 1 전극은 양극이고, 상기 게 2 전극은 음극이거나， 또는 상기 거 U 전극은 음극이고， 상기 게 2 전극은 양극이다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐, 크름， 구리， 아연， 금과 같은 금속 또는 이들의 합금; 아연 산화물， 인듐 산화물, 인듐주석 산화물 ( IT0) , 인듐아연 산화물 ( IZ0)과 같은 금속 산화물; Ζη0 :Α1 또는 SN02 : Sb와 같은 금속과 산화물의 조합; 폴리 (3一 메틸티오펜)， 폴리 [3，4- (에틸렌- 1 2-디옥시 )티오펜 KPEDOT) , 폴리피를 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다ᅳ The above Reaction Scheme 1 is an amine substitution reaction, which is a reaction to produce the compound represented by Formula 1-1 by counterion of the compound represented by Formula 1-a and the compound represented by Formula 1-b. The reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reaction for the amine-substituted reaction can be varied as is known in the art. Preferably, X is halogen (more preferably bromo, or chloro). The above production method can be more specific in the production example to be described later. Also, the present invention provides an organic light emitting device including the compound represented by Formula 1. In one embodiment, the present invention provides a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do. The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. The organic material layer may include a hole injecting layer, a hole transporting layer, or a hole injecting and transporting hole, and the hole injecting layer, the hole transporting layer, And a compound to be displayed. In addition, the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1). In particular, the compound according to the present invention can be used as a diskette of a light emitting layer. The organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1). Further, the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound represented by the above formula (1). The organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1). In addition, the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. Fig. 1 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4. Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound represented by Formula 1 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer. The organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1). In addition, when the organic light emitting diode includes a plurality of organic layers, the organic layer may be formed of the same material or another material. For example, the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic layer, and a second electrode on a substrate. In this case, a PVD (Physical Vapor Deposition) method such as a sputtering method or an e-beam evaporation method is used to deposit a metal or a conductive metal oxide or an alloy thereof A hole transporting layer, a light emitting layer, and an electron transporting layer is formed thereon, and then a substance usable as a cathode is deposited thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. In addition, the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing screen printing, spraying, coating, and the like, but is not limited thereto. In addition to such a method, a method of forming an organic material layer from a cathode material, The organic light emitting device can be manufactured by sequentially depositing the material (WO 2003/012890). However, the manufacturing method is not limited thereto. In one example, the first electrode is an anode, the second electrode is a cathode, or the second electrode is a cathode, and the second electrode is a cathode. As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted to the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Ζη0: Α1 SN0 or 2: a combination of a metal and an oxide such as Sb; Poly (3一methylthiophene), poly [3, 4- (ethylene-1, 2-dioxy) thiophene KPEDOT), but a conductive polymer such as a polyester and blood and polyaniline, but are not limited thereto eu
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘， 칼슘， 나트륨， 칼륨， 티타늄， 인듐， 이트륨， 리튬， 가돌리늄, 알루미늄， 은， 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li¾/Al과 같은 다층 구조 물질 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 정공주입층은 전극으로부터 정공을 주입하는 층으로， 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과， 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMCKhighest occupi ed mol ecul ar orbi tal )가 양극 물질의 일함수와 주변 유기물 층의 H0M0 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린 (porphyr in) , 올리고티오펜， 아릴아민 계열의 유기물， 핵사니트릴핵사아자트리페닐렌 계열의 유기물， 퀴나크리돈 (quinacr idone)계멸의 유기물， 페릴렌 (perylene) 계열의 유기물， 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나， 이들에만 한정 되는 것은 아니다. 상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물， 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서， 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8-히드록시-퀴놀린 알루미늄 착물 (Alq3) ; 카르바졸 계열 화합물; 이량체화 스티릴 (dimer i zed styryl ) 화합물; BAlq; 10- 히드록시벤조 퀴놀린 -금속 화합물; 벤족사졸， 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리 (P—페닐렌비닐렌 KPPV) 계열의 고분자; 스피로 (spi ro) 화합물; 폴리플루오렌, 루브렌 둥이 있으나, 이들에만 한정되는 것은 아니다. 상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 둥이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체， 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체， 페난트렌 화합물， 플루오란텐 화합물 둥이 있고, 헤테로환 함유 화합물로는 카바졸 유도체， 디벤조퓨란 유도체， 래더형 퓨란 화합물， 피리미딘 유도체 등이 있으나， 이에 한정되지 않는다. 도펀트 재료로는 방향족 아민 유도체， 스트릴아민 화합물, 붕소 착체， 플루오란텐 화합물， 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서， 아릴아미노기를 갖는 피렌， 안트라센， 크리센， 페리플란텐 둥이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기， 알킬기， 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민， 스티릴디아민, 스티릴트리아민， 스티릴테트라아민 등이 있으나， 이에 한정되지 않는다. 또한， 금속 착체로는 이리듐 착체， 백금 착체 둥이 있으나, 이에 한정되지 않는다. 상기 전자수송층은 전자주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서， 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 A1 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본 -금속 착물 등이 있으나， 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히， 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘， 바륨， 칼슘， 이테르븀 및 사마륨이고， 각 경우 알루미늄 층 또는 실버층이 뒤따른다. 상기 전자주입층은 전극으로부터 전자를 주입하는 층으로， 전자를 수송하는 능력을 갖고， 음극으로부터의 전자 주입 효과， 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며， 발광층에서 생성된 여기자의 정공주입층에의 이동을 방지하고， 또한， 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄， 다이페노퀴논， 티오피란 다이옥사이드， 옥사졸， 옥사다이아졸， 트리아졸， 이미다졸， 페릴렌테트라카복실산， 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체， 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나， 이에 한정되지 않는다. 상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬， 비스 (8- 하이드록시퀴놀리나토)아연， 비스 (8-하이드록시퀴놀리나토)구리, 비스 (8- 하이드록시퀴놀리나토)망간， 트리스 (8-하이드록시퀴놀리나토)알루미늄， 트리스 (2—메틸— 8—하이드록시퀴놀리나토)알루마늄， 트리스 (8- 하이드록시퀴놀리나토)갈륨, 비스 (10-하이드록시벤조 [h]퀴놀리나토)베릴륨, 비스 ( 10-하이드록시벤조 [h]퀴놀리나토)아연， 비스 (2-메틸 -8- 퀴놀리나토)클로로갈륨, 비스 (2-메틸 -8-퀴놀리나토) ( 0-크레졸라토)갈륨， 비스 (2-메틸 -8-퀴놀리나토) (1-나프를라토)알루미늄， 비스 (2-메틸 -8- 퀴놀리나토) (2-나프를라토)갈륨 등이 있으나， 이에 한정되지 않는다. 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형， 후면 발광형 또는 양면 발광형일 수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다. 상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며， 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다. The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or Li / Al, but the present invention is not limited thereto. The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the HOMO concentration of the hole injecting material is between the work function of the anode material and H0M0 of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic material, A quinacridone-based organic material, a perylene-based organic material, an anthraquinone, a polyaniline-based material, and a polythiophene-based conductive polymer. It is not. The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer by using a hole transport material. Is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Poly (P-phenylene vinylene KPPV) series polymer; Spiro compounds; Polyfluorene, and lubrene, but are not limited thereto. The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Compounds, pyrimidine derivatives, and the like, but are not limited thereto. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, Fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherane having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted A compound in which at least one aryl vinyl group is substituted with an arylamine, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. The metal complexes include iridium complexes and platinum complexes, but are not limited thereto. The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing 5-membered ring derivative, But is not limited thereto. Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10- (2-methyl-8-quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium (0-cresolato) gallium, bis But are not limited thereto. The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used. In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device. The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
[제조예] [Manufacturing Example]
제조예 1: 화합물 A-1-1내지 A-1-3의 제조 Production Example 1: Preparation of the compounds A-1-1 to A-1-3
Figure imgf000115_0001
Figure imgf000115_0001
Figure imgf000115_0002
단계 1) 화합물 A-l-1의 제조
Figure imgf000115_0002
Step 1) Preparation of compound Al-1
9，9'-스피로바이 [플루오렌]— 2-올 (150 g, 465 匪 ol)을 DMF(400 ml)에 첨가하여 용해시킨 후 0°C에서 NBS(83.5 g, 469 隱 ol)을 천천히 적가하고 실은에서 3시간 동안 교반하였다. 상온에서 물과 클로로포름으로 추출한 후 흰색의 고체를 핵산으로 재결정하여 상기 화합물 A-1— 1(162 g, 수율 85%)을 제조하였다. 9,9'-bi-spiro [fluorene; - slowly 2-ol (150 g, 465匪ol) of DMF NBS (83.5 g, 469隱ol) at 0 ° C was added and dissolved in (400 ml) And the mixture was stirred at room temperature for 3 hours. After extraction with water and chloroform at room temperature, the white solid was recrystallized from the nucleic acid to obtain the compound A-1- 1 (162 g, yield 85%).
MS[M+H]+= 412.30 단계 2) 화합물 A-1ᅳ 2의 제조 MS [M + H] < + > = 412.30 Step 2) Preparation of compound A-
질소 분위기에서 상기 화합물 A-1-U30 g, 72.9 隱 ol), 비스 (피나콜라토)다이보론 (22.23 g, 87.5 瞧 ol) 및 아세트산칼륨 (25.06 g, 255.2 mmol)을 섞고， 다이옥산 (300 ml)을 첨가하고 교반하면서 가열하였다. 환류되는 상태에서 비스 (디벤질리딘아세톤)팔라듐 (840 mg, 0.02 mol¾>)과 트리사이클로핵실포스핀 (820 mg, 0.04 mol¾>)을 넣고 3시간 동안 가열 및 교반하였다. 반응 종료 후， 상온으로 온도를 낮춘 후 여과하였다. 여과액에 물을 붓고 클로로포름으로 추출하고， 유기층을 무수황간마그네슘으로 건조하였다. 감압 증류 후 에틸아세테이트과 핵산으로 재결정하여 상기 화합물 A-l-2(28.4 g, 85%)를 제조하였다.  Bis (pinacolato) diboron (22.23 g, 87.5 mmol) and potassium acetate (25.06 g, 255.2 mmol) were mixed in a nitrogen atmosphere and dioxane (300 ml ) Was added and heated with stirring. Bis (dibenzylidineacetone) palladium (840 mg, 0.02 mol?) And tricyclohexylphosphine (820 mg, 0.04 mol?>) Were added under reflux and heated and stirred for 3 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was recrystallized from ethyl acetate and a nucleic acid to obtain the compound A-1-2 (28.4 g, 85%).
MS[M+H]+= 459.36 단계 3) 화합물 A-1-3의 제조 MS [M + H] < + > = 459.36 Step 3) Preparation of Compound A-1-3
상기 화합물 A-l-2(30 g, 65.5 醒 ol )를 2M 수산화나트륨 용액에 투입하고 0°C로 안정화시킨 후 과산화수소 (25 ml , 131.18 mmol )를 교반하면서 첨가하여 반웅을 완결하였다. 반웅 종료 후， 물을 투입하여 30분간 교반한 후 상온으로 온도를 낮추어， 상기 화합물 A-l-3(18.28 g, 수율 80%)를 제조하였다. The compound Al-2 (30 g, 65.5 mg ol) was added to 2M sodium hydroxide solution and stabilized at 0 ° C. Then, hydrogen peroxide (25 ml, 131.18 mmol) was added with stirring to complete the reaction. After completion of the reaction, water was added thereto, stirred for 30 minutes, and then cooled to room temperature to prepare the compound Al-3 (18.28 g, yield 80%).
MS[M+H]+= 349.30 MS [M + H] < + > = 349.30
Figure imgf000116_0001
제조예 2-1: 화합물 B-1-1의 제조
Figure imgf000116_0001
Production Example 2-1: Preparation of Compound B-1-1
3,4—디히드록시 -9H-플루오렌 -9-온 (30 g, 141.3 画 ol), 4-브로모 -1，2- 디플루오로벤젠 (40.93 gᅳ 212.06 画 ol) 및 포타슘카보네이트 (82.06 g, 593.7 mmol)을 DMF(300 ml)에 첨가하여 환류 및 교반하였다. 반웅 완료 후 상온으로 식히고 필터하였다. 상온에서 물과 클로로포름으로 추출한 후 흰색의 고체를 에틸아세테이트와 핵산으로 컬럼하여 상기 화합물 B-1-1을 제조하였다 (18.06 g, 수율 35%) .  (30 g, 141.3 mole ol), 4-bromo-1,2-difluorobenzene (40.93 g? 212.06 占 퐉 ol) and potassium carbonate 82.06 g, 593.7 mmol) was added to DMF (300 ml) and refluxed and stirred. After completion of the reaction, the solution was cooled to room temperature and filtered. After extraction with water and chloroform at room temperature, the white solid was columned with ethyl acetate and nucleic acid to give the compound B-1-1 (18.06 g, yield 35%).
MS[M+H]+= 366.18 제조예 2-2: 화합물 B-1-2의 제조 MS [M + H] < + > = 366.18 Preparation Example 2-2: Preparation of compound B-1-2
상기 B— 1-1의 제조에서， 컬럼으로 분리하여 화합물 B-1-2을 제조하였다.  In the preparation of the above B-1-1, a column was used to separate the compound B-1-2.
MS[M+H]+= 366.18 、 제조예 2-3: 화합물 B-1-3의 제조 MS [M + H] < + > = 366.18, Production example 2-3: Preparation of compound B-1-3
4-브로모ᅳ1，2-디플루오로벤젠 대신 1-브로모 -2 ,3-디플루오로벤젠을 사용한 것을 제외하고는, 화합물 B-1-1의 제조와 동일한 방법으로 제조하여 B-1-3을 제조하였다.  Preparation of Compound B-1-1 was repeated except that 1-bromo-2,3-difluorobenzene was used instead of 4-bromobenzene-1,2-difluorobenzene. 1-3.
MS [M+H]+= 366.18 제조예 2-4: 화합물 B-1-4의 제조 MS [M + H] < + > = 366.18 Preparation Example 2-4: Preparation of compound B-1-4
상기 B-1— 3의 제조에서， 컬럼으로 분리하여 화합물 B-1-4를 제조하였다.  In the preparation of the above B-1-3, the compound B-1-4 was prepared by separating into a column.
MS[M+H]+= 366.18 제조예 2-5: 화합물 B-1-5의 제조 MS [M + H] < + > = 366.18 Preparation Example 2-5: Preparation of compound B-1-5
4-브로모 -1,2-디플루오로벤젠 대신 1,2—디클로로 -4,5- 디플루오로벤젠을 사용한 것을 제외하고는 화합물 B-1-1의 제조와 동일한 방법으로 화합물 B-1-5를 제조하였다. MS[M+H]+= 356. 17 제조예 2-6: 화합물 B-l-6의 제조 Compound B-1 was obtained in the same manner as in the production of Compound B-1-1 except that 1,2-dichloro-4,5-difluorobenzene was used in place of 4-bromo-1,2-difluorobenzene. -5. MS [M + H] < + > = 356. 17 Preparation Example 2-6: Preparation of compound Bl-6
4-브로모 -1， 2-디플루오로벤젠 대신 1， 4-디클로로 -2， 3- 디플루오로벤젠을 사용한 것을 제외하고는, 화합물 B-1ᅳ 1의 제조와 동일한 방법으로 화합물 B-1-6을 제조하였다.  Compound B-1 was prepared in the same manner as in the production of Compound B-1, except that 1, 4-dichloro-2,3-difluorobenzene was used in place of 4-bromo-1,2-difluorobenzene. 1-6.
MS[M+H]+= 356. 17 MS [M + H] < + > = 356.17
Figure imgf000118_0001
제조예 3-1: 화합물 A1의 제조
Figure imgf000118_0001
Production Example 3-1: Preparation of Compound A1
3 , 4—디히드록시 -9H-플루오렌 -9-온 대신 화합물 A-1-3을 사용한 것을 제외하고는， 화합물 B-1-1의 제조와 동일한 방법으로 화합물 A1을 제조하였다. Compound A1 was obtained in the same manner as in the production of Compound B-1-1, except that Compound A-1-3 was used in place of Compound A-3, 4-dihydroxy-9H-fluoren- .
MS[M+H] += 502.38 제조예 3-2 : 화합물 A2의 제조 MS [M + H] < + > = 502.38 Preparation Example 3-2: Preparation of compound A2
3 , 4-디히드록시— 9H-플루오렌 -9-온 대신 화합물 A-1-3을 사용한 것을 제외하고는， 화합물 B-1-2의 제조와 동일한 방법으로 화합물 A1을 제조하였다.  Compound A1 was prepared in the same manner as in the preparation of Compound B-1-2, except that Compound A-1-3 was used instead of 3, 4-dihydroxy-9H-fluoren-9-one.
MS[M+H] += 502.38 제조예 3-3: 화합물 A3의 제조 MS [M + H] < + > = 502.38 Preparation Example 3-3: Preparation of Compound A3
3， 4-디히드록시 -9H-플루오렌 -9-온 대신 화합물 A— 1ᅳ3을 사용한 것을 제외하고는, 화합물 B-1-3의 제조와  Compound B-1-3 was prepared in the same manner as Compound B-1 except that Compound A-1 was replaced with Compound A-1 in place of 3, 4-dihydroxy-9H-
제조하였다. .
MS[M+H]+= 502.38 제조예 3-4: 화합물 A4의 제조  MS [M + H] < + > = 502.38 Preparation Example 3-4: Preparation of Compound A4
3， 4-디히드록시 -9H-플루오렌 -9-온 대신 화합물 A— 1— 3을 사용한 것을 제외하고는， 화합물 B-1-4의 제조와 동일한 방법으로 화합물 A4를 제조하였다.  Compound A4 was prepared in the same manner as in the preparation of Compound B-1-4, except that Compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.
MS[M+H]+= 502.38 제조예 3-5: 화합불 A5의 제조 MS [M + H] < + > = 502.38 Preparation Example 3-5: Preparation of compound A5
3， 4-디히드록시 -9H-플루오렌 -9-은 대신 화합물 A— 1-3을 사용한 것을 제외하고는， 화합물 B-1— 5의 제조와 동일한 방법으로 제조하여 화합물 A5를 제조하였다.  Compound A5 was prepared in the same manner as in the preparation of Compound B-1-5, except that Compound A-1-3 was used instead of Compound A-3, 4-dihydroxy-9H-fluorene-9-.
MS[M+H]+= 492.37 제조예 3-6 : 화합물 A6의 제조  MS [M + H] < + > = 492.37 Preparation Example 3-6: Preparation of Compound A6
3， 4-디히드록시— 9H-플루오렌 -9-온 대신 화합물 A— 1— 3을 사용한 것을 제외하고는， 화합물 B-1-6의 제조와 동일한 방법으로 화합물 A6를 제조하였다. Compound A6 was synthesized in the same manner as in the preparation of Compound B-1-6, except that Compound A-1-3 was used in place of Compound A- 1-3, 4-dihydroxy-9H-fluoren- .
MS[M+H]+= 492.37 MS [M + H] < + > = 492.37
Figure imgf000120_0001
Figure imgf000120_0001
B6 제조예 4-1: 화합물 B1의 제조  B6 Preparation Example 4-1: Preparation of Compound B1
2-아미노비페닐 (80.2 瞧 ol)을 THF(250 ml)에 용해한 후 온도를 - 78°C로 낮춘 후 2.5M n-BuLi(9 ml)을 적가하고 30분 동안 교반한 후 화합물 B-1-K80.2 隱 ol )을 넣어주고 상온으로 올린 후 1시간 동안 교반하였다. 1N HC 1 ( 100 ml )를 넣어주고 30분 동안 교반한 후 층분리하여 용매를 제거한 후 에틸아세테이트와 핵산으로 컬럼하고 에틸아세테이트로 재결정하여 필터하고 건조시켰다. 그 후 건조된 고체를 아세트산 (300 ml )에 첨가한 후， 가열 및 교반하고 황산 ( 1 ml )을 적가한 후 3시간 동안 환류시켰다. 반웅 완료 후 필터하고 재결정하여 화합물 B1을 제조하였다. After 2-aminobiphenyl (80.2 瞧 ol) was dissolved in THF (250 ml), the temperature was lowered to -78 ° C, 2.5M n-BuLi (9 ml) was added dropwise and the mixture was stirred for 30 minutes. B-1-K80.2 隱 ol) was added, and the mixture was stirred at room temperature for 1 hour. 1N HCl (100 ml) was added thereto, and the mixture was stirred for 30 minutes. Then, the mixture was separated, and the solvent was removed. The solvent was removed by column chromatography using ethyl acetate and nucleic acid, followed by recrystallization from ethyl acetate. The dried solid was then added to acetic acid (300 ml), heated and stirred, sulfuric acid (1 ml) was added dropwise, and the mixture was refluxed for 3 hours. After completion of the reaction, the product was filtered and recrystallized to obtain Compound B1.
MS[M+H]+= 502.38 제조예 4-2: 화합물 B2의 제조 MS [M + H] < + > = 502.38 Preparation Example 4-2: Preparation of compound B2
화합물 B— 1-1 대신 화합물 B-1-2을 사용한 것을 제외하고는, 화합물 Except that the compound B-1-2 was used in place of the compound B-1-1, the compound
B1의 제조와동일한 방법으로 화합물 B2를 제조하였다. Compound B2 was prepared in the same manner as in the preparation of B1.
MS[M+H]+= 502.38 제조예 4-3: 화합물 B3의 제조  MS [M + H] < + > = 502.38 Preparation Example 4-3: Preparation of compound B3
화합물 B-1-1 대산 화합물 B-1-3을 사용한 것을 제외하고는， 화합물 Compound B-1-1 Compound B-1-1 was obtained in the same manner as Compound
B1의 제조와동일한 방법으로 화합물 B3을 제조하였다. Compound B3 was prepared in the same manner as in the preparation of B1.
MS[M+H]+= 502.38 제조예 4-4: 화합물 B4의 제조  MS [M + H] < + > = 502.38 Preparation Example 4-4: Preparation of compound B4
화합물 B-1-1 대신 Bᅳ 1ᅳ4을 사용한 것을 제외하고는， 화합물 B1의 제조와동일한 방법으로 화합물 B4를 제조하였다.  Compound B4 was prepared in the same manner as in the preparation of compound B1, except that B? 1? 4 was used instead of compound B-1-1.
MS[M+H]+= 502.38 제조예 4-5 : 화합물 B5의 제조 MS [M + H] < + > = 502.38 Preparation Example 4-5: Preparation of compound B5
화합물 B-1-1 대신 B— 1-5을 사용한 것을 제외하고는， 화합물 B1의 제조와 동일한 방법으로 화합물 B5를 제조하였다.  Compound B5 was prepared in the same manner as in the preparation of Compound B1, except that B-1-5 was used instead of Compound B-1-1.
MS[M+H]+= 492.37 제조예 4-6 : 화합물 B6의 제조 MS [M + H] < + > = 492.37 Preparation Example 4-6: Preparation of compound B6
화합물 B-1-1 대신 B-1-6을 사용한 것을 제외하고는， 화합물 B1의 제조와 동일한 방법으로 화합물 B6를 제조하였다. Except that B-1-6 was used in place of compound B-1-1. Compound B6 was prepared in the same manner as the preparation.
MS[M+H]+= 492.37  MS [M + H] < + > = 492.37
[실시예] [Example]
Figure imgf000122_0001
화합물 Al(15 g, 29.9 隱 ol), 다이([1,1'-바이페닐]-4-일)아민(9.81 g, 30.5 隱 ol), 및 소듐 -t-부록사이드 (4.03 g, 41.8 mol)을 자일렌에 넣고 가열 및 교반한 뒤 환류시키고 [비스 (트라이 -t-부틸포스핀)]팔라듐 (170 mg, 1 mol%)을 넣었다. 상온으로 온도를 낮추고 반웅을 종결한 후， 테트라하이드로퓨란과 에틸아세테이트를 이용해 재결정하여 화합물 1(16.4 g, 수율 74%)을 제조하였다.
Figure imgf000122_0001
(9.81 g, 30.5  ol), and sodium-t-heptoxide (4.03 g, 41.8 mol) were added to a solution of the compound Al (15 g, 29.9  ol) ) Was added to xylene, heated and stirred, refluxed, and [bis (tri-t-butylphosphine)] palladium (170 mg, 1 mol%) was added. After the temperature was lowered to room temperature, the reaction mixture was terminated and recrystallized from tetrahydrofuran and ethyl acetate to obtain Compound 1 (16.4 g, yield 74%).
MS[M+H]+= 742.89 MS [M + H] < + > = 742.89
Figure imgf000122_0002
Figure imgf000122_0002
화합물 A1 대신 화합물 A2를 사용하고， 다이 ( [1，1'-바이페닐] -4- 일)아민 대신 9，9-다이메틸- 페닐-911-플루오렌-2-아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 2를 제조하였다. Except that compound A2 was used instead of compound A1 and 9,9-dimethyl-phenyl-911-fluoren-2-amine was used instead of di [(1,1'-biphenyl] , Compound 1 was prepared in the same manner as Compound 1 to give Compound 2 .
MS[M+H]+= 706.86 MS [M + H] < + > = 706.86
Figure imgf000123_0001
화합물 A1 대신 화합물 A3를 사용하고, 다이 ([1,1 바이페닐] -4- 일)아민 대신 ^([1，1'-다이페닐]-2-일)-9，9-다이메틸- —플루오렌-2- 아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 3을 제조하였다.
Figure imgf000123_0001
Instead of compound A1, compound A3 was used, and instead of ([1,1'-diphenyl] -2-yl) -9,9-dimethyl- Fluorene-2-amine was used in place of the compound 3, to thereby prepare the compound 3. [
MS[M+H]+= 782.96 MS [M + H] < + > = 782.96
Figure imgf000123_0002
화합물 A1 대신 화합물 A4를 사용하고， 다이 ( [1,1 바이페닐] -4- 일)아민 대신 Ν-([1,1'-비페닐 ]-4-일) -(1，1' ;4'，1'-터페닐 )ᅳ4-아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 4를 제조하였다.
Figure imgf000123_0002
Compound (A4) was used instead of Compound A1, and N - ([1,1'-biphenyl] -4-yl) - (1,1 '; 4 ', 1'-terphenyl) ᅳ-4-amine was used in place of the compound 4 to prepare the compound 4.
MS[M+H]+= 818.99 실시예 5: 화합물 5의 제조
Figure imgf000124_0001
MS [M + H] < + > = 818.99 Example 5: Preparation of compound 5
Figure imgf000124_0001
int.1  int.1
A2  A2
Figure imgf000124_0002
단계 1) 화합물 int.l의 제조
Figure imgf000124_0002
Step 1) Preparation of compound int.l
화합물 A-2-1 대신 화합물 A2를 사용하고， 2-브로모 -4-클로로 -1- 아이오도벤젠 대신 3-클로로페닐보로닉산을 사용한 것을 제외하고는， 화합물 A-3-1의 제조와 동일한 방법으로 제조하여 화합물 int.l을 제조하였다.  Preparation of Compound A-3-1 Except that Compound A2 was used instead of Compound A-2-1 and 3-chlorophenylboronic acid was used instead of 2-bromo-4-chloro-1-iodobenzene To give compound int.l.
MS[M+H]+= 534.02 단계 2) 화합물 5의 제조 MS [M + H] < + > = 534.02 Step 2) Preparation of compound 5
상기 화합물 1의 제조에서， 화합물 A1 대신 화합물 int.l을 사용하고, 다이 ([1，1'-바이페닐] -4-일)아민 대신 N-페닐 -[1，1'_비페닐 ]-2-아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 5를 제조하였다.  In the preparation of the compound 1, the compound int.l was used instead of the compound A1, and N-phenyl- [1,1'-biphenyl] - 2-amine was used instead of 2-methyl-2-pyridin-2-amine, compound 5 was prepared.
MS[M+H]+= 756.87 실시예 6: 화합물 6의 제조 MS [M + H] < + > = 756.87 Example 6: Preparation of compound 6
Figure imgf000125_0001
단계 1) 화합물 int.4의 제조
Figure imgf000125_0001
Step 1) Preparation of compound int.4
상기 화합물 int.l의 제조에서， 화합물 A2 대신 화합물 A3을 사용하고， 3-클로로페닐보로닉산 대신 (4'—클로로— [1,1'-비페닐 ]— 3一 일)보로닉산을 사용한 것을 제외하고는， 화합물 int.l의 제조와 동일한 방법으로 제조하여 화합물 int.4을 제조하였다.  In the preparation of the above compound int.l, Compound A3 was used instead of Compound A2, and (4'-chloro- [1,1'-biphenyl] -3yl) boronic acid was used instead of 3-chlorophenylboronic acid , The compound int.l was prepared in the same manner as the preparation of the compound int.l to prepare the compound int.4.
MS[M+H]+= 610.12 단계 2) 화합물 6의 제조 MS [M + H] < + > = 610.12 Step 2) Preparation of compound 6
상기 화합물 1의 제조에서， 화합물 A1 대신 화합물 int.4을 사용하고， 다이 ([1，1'-바이페닐] -4-일)아민 대신 디페닐아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 6을 제조하였다.  In the preparation of the compound 1, except for using the compound int.4 instead of the compound A1 and using diphenylamine instead of the die ([1,1'-biphenyl] -4-yl) amine, To give Compound 6.
MS[M+H]+= 742.89 MS [M + H] < + > = 742.89
Figure imgf000125_0002
Figure imgf000125_0002
상기 화합물 1의 제조에서， 화합물 A1 대신 화합물 A5을 사용하고， 다이 ([1,1'-바이페닐] -4-일)아민 대신 디페닐아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 7을 제조하였다.  The same procedure as in the preparation of Compound 1 was conducted except that Compound A5 was used instead of Compound A1 and diphenylamine was used instead of the di [(1,1'-biphenyl) -4- ≪ / RTI > to give Compound 7.
MS[M+H]+= 757.91
Figure imgf000126_0001
상기 화합물 1의 제조에서， 화합물 A1 대신 화합물 A6을 사용하고， 다이 ( [1，1 ' -바이페닐] -4-일)아민 대신 디페닐아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동알한 방법으로 제조하여 화합물 8을 제조하였다. MS [M + H] < + > = 757.91
Figure imgf000126_0001
The preparation of Compound 1 was repeated except that Compound A6 was used instead of Compound A1 and diphenylamine was used instead of the di [(1,1 '-biphenyl] -4-yl) amine. To prepare Compound 8.
MS[M+H]+= 757.91 MS [M + H] < + > = 757.91
Figure imgf000126_0002
Figure imgf000126_0002
화합물 A1 대신 화합물 B1을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 9를 제조하였다.  Compound 9 was prepared in the same manner as in the preparation of Compound 1, except that Compound B1 was used instead of Compound A1.
MS[M+H]+= 742.89 실시예 10: 화합물 10의 제조 MS [M + H] < + > = 742.89 Example 10: Preparation of compound 10
Figure imgf000127_0001
상기 화합물 1의 제조에서， 화합물 A1 대신 화합물 B2을 사용하고， 다이 ([1,1'-바이페닐] -4-일)아민 대신 9,9-트리페닐-911-플루오렌-4- 아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 10을 제조하였다.
Figure imgf000127_0001
In the preparation of the compound 1, the compound B2 was used instead of the compound A1, and 9,9-triphenyl-911-fluoren-4-amine was used instead of the di [(1,1'- Compound 10 was prepared in the same manner as in the preparation of Compound 1, except that the compound 10 was used.
MS[M+H]+= 831.00 MS [M + H] < + > = 831.00
Figure imgf000127_0002
Figure imgf000127_0002
상기 화합물 1의 제조에서, 화합물 A1 대신 화합물 B3을 사용하고， 다이 ( [1，1'-바이페닐] -4-일)아민 대신 Ν-([1,1'—비페닐 ]-4-일 ΗΙ,Ι'- 비페닐 )-2-아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 11을 제조하였다.  In the preparation of the compound 1, Compound B3 was used instead of Compound A1, and N - ([1,1'-biphenyl] -4-yl Compound No. 11 was prepared in the same manner as in the preparation of Compound 1, except that Compound (11) was used instead of Compound (11).
MS[M+H]+= 742.89 실시예 12: 화합물 12의 제조 MS [M + H] < + > = 742.89 Example 12: Preparation of compound 12
Figure imgf000128_0001
상기 화합물 1의 제조에서, 화합물 A1 대신 화합물 B4을 사용하고， 다이 ([1，1'-바이페닐] -4-일)아민 대산 N-페닐 -[1,1;4'，1'-터페닐 ]-4-아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 12를 제조하였다.
Figure imgf000128_0001
In the preparation of the above compound 1, Compound B4 was used in place of Compound A1, and a compound represented by the formula [1, 1 '-biphenyl] -4-yl) Phenyl] -4-amine, the compound 12 was prepared in the same manner as in the preparation of the compound 1.
MS[M+H]+= 742.89 MS [M + H] < + > = 742.89
Figure imgf000128_0002
Figure imgf000128_0002
화합물 A-2-1 대신 화합물 B5을 사용하고， 2-브로모—4-클로로 -1- 아이오도벤젠 대신 Ν,Ν—디페닐 4— (4，4，5，5ᅳ테트라메틸 -1,3，2- 디옥사보로레인 -2-일)아닐린을 사용한 것을 제외하고는， 상기 화합물 Α-3- 1의 제조와동일한 방법으로 제조하여 화합물 13을 제조하였다.  Compound B5 was used instead of Compound A-2-1, and N, N-diphenyl 4- (4,4,5,5-tetramethyl-1, 3-1) was prepared in the same manner as in the preparation of the compound A-3- 1 except that 3, 2-dioxabororane-2-yl) aniline was used.
MS[M+H]+= 910.10 실시예 14: 화합물 14의 제조 MS [M + H] < + > = 910.10 Example 14: Preparation of compound 14
Figure imgf000129_0001
상기 화합물 1의 제조에서， 화합물 A1 대신 화합물 B6을 사용하고， 다이 바이페닐]ᅳ 4ᅳ일)아민 대신 N-페닐 -[1，1'-비페닐 ]-2-아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 14를 제조하였다.
Figure imgf000129_0001
Except for using Compound B6 instead of Compound A1 and N-phenyl- [1,1'-biphenyl] -2-amine instead of dibiphenyl] xanthylamine in the preparation of Compound 1, Compound 14 was prepared in the same manner as Compound 1.
MS[M+H]+= 910.10 MS [M + H] < + > = 910.10
Figure imgf000129_0002
Figure imgf000129_0002
상기 화합물 1의 제조에서 화합물 A1 대신 화합물 C1을 사용하고， 다이 ([1，1'-바이페닐] -4-일)아민 대신 N—페닐— [1，1'_비페닐 ]-2-아민을 사용한 것을 제외하고는， 화합물 1의 제조와 동일한 방법으로 제조하여 화합물 15를 제조하였다.  Compound C1 was used instead of Compound A1 in the preparation of Compound 1, and N-phenyl- [1,1'-biphenyl] -2-amine (Compound , Compound 15 was prepared in the same manner as Compound 1 was prepared.
MS[M+H]+= 666.79 실험예 1-1 MS [M + H] < + > = 666.79 [
ΠΌ (인듐 주석 산화물)가 1,000 A 두께로 박막 코탕된 유리 기판 (corning 7059 glass)을， 분산제를 녹인 증류수에 넣고 초음파로 '세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며， 증류수는 Millipore Co. 제품의 필터 (Filter)로 2차 걸러진 증류수를 사용하였다. IT0를 30분간 세척한 후， 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜， 아세톤， 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. 이렇게 준비된 ΠΌ 투명 전극 위에 하기 HAT 화합물을 500 A의 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 그 위에 정공을 수송하는 물질인 앞서 제조한 화합물 K900A)을 진공증착한 후， 이어서 상기 정공 수송층 위에 하기 HT2 화합물을 막두께 50 A으로 진공증착하여 정공 조절층을 형성하였다. 상기 정공 조절층 상에 하기 HI 화합물 (호스트)과 하기 D1 화합물 (도판트)을 25:1의 중량비로 진공 증착하여 300 A 두께의 발광층을 형성하였다. 그 다음에 하기 E1 화합물 (300A) 및 LiQ를 1:1 비율로 증착하여 전자주입 및 수송충으로 순차적으로 열 진공 증착하였다. 상기 전자 수송층 위에 순차적으로 12 A 두께의 리튬 플루오라이드 (LiF)와 2， 000 A 두께의 알루미늄을 증착하여 음극을 The ΠΌ (indium tin oxide) is 1,000 A glass substrate (corning 7059 glass) kotang thin film to a thickness, into a dispersing agent dissolved in distilled water and washed with ultrasonic waves. The detergent was a product of Fischer Co., Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. ITO was washed for 30 minutes and then ultrasonically washed for 2 minutes with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying. The following HAT compound was thermally vacuum deposited to a thickness of 500 A on the thus prepared " t " transparent electrode to form a hole injection layer. The compound K900A prepared above, which is a material for transporting holes, was vacuum-deposited on the hole transport layer, and then the HT2 compound was vacuum-deposited to a film thickness of 50 A on the hole transport layer to form a hole control layer. The following HI compound (host) and the following D1 compound (dopant) were vacuum deposited on the hole-transporting layer at a weight ratio of 25: 1 to form a 300 A thick light emitting layer. Then, the following E1 compounds (300A) and LiQ were vapor-deposited at a ratio of 1: 1, followed by thermal vacuum evaporation with electron injection and water-feeding. Lithium fluoride (LiF) 12 A thick and aluminum 2,000 A thick were sequentially deposited on the electron transport layer to form a cathode
Figure imgf000130_0001
상기의 과정에서 유기물의 증착 속도는 1 A/sec를 유지하였고， 리튬플루라이드는 0.2 A/sec, 알루미늄은 3 ~ 7 A/sec의 증착속도를 유지하였으며， 증착시 진공도는 1 Χ 1(Γ7 ~ 5X 10— 8 torr를 유지하였다. 실험예 1-2 내지 1-15
Figure imgf000130_0001
The deposition rate of the organic material was maintained at 1 A / sec, Lithium fluoride is 0.2 A / sec, aluminum was deposited at a rate of 3 ~ 7 A / sec, the deposition, a vacuum was maintained for 1 Χ 1 (Γ 7 ~ 5X 10- 8 torr. Experimental Example 1-2 to 1-15
- 상기 실험예 1-1과 동일한 방법으로 제조하되， 화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 소자를 제조하였다. 비교실험예 1-1 내지 1-6  - An organic light emitting device was prepared in the same manner as in Experimental Example 1-1, except that the compound described in Table 1 was used instead of Compound 1. Comparative Experimental Examples 1-1 to 1-6
상기 실험예 1-1과 동일한 방법으로 제조하되 , 화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서， HTl , HT3 , HT4는 각각 하기와 같다.  Except that the compound described in the following Table 1 was used instead of the compound 1, an organic light emitting device was prepared in the same manner as in Example 1-1. In Table 1, HT1, HT3 and HT4 are as follows.
Figure imgf000131_0001
Figure imgf000131_0001
비교실험예 1-4 Comparative Experimental Examples 1-4
상기 실험예 1-1과 동일한 방법으로 제조하되， 정공 수송층으로 화합물 1 대신 하기 HT3 화합물을 사용하고， 정공 조절층으로 화합물 HT2 대신 하기 HT5 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 소자를 제조하였다. Except that HT3 compound was used in place of Compound 1 as the hole transport layer and HT5 compound was used in place of the HT2 as the hole control layer in the same manner as in Experimental Example 1-1 Respectively.
Figure imgf000132_0001
비교실험예 1-5및 1-6
Figure imgf000132_0001
Comparative Experimental Examples 1-5 and 1-6
상기 실험예 1-1과 동일한 방법으로 제조하되， 화합물 1 대신 하기 표 1에 기재된 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 . o o o o o o o o  Was prepared in the same manner as in Experimental Example 1-1, except that the compound described in Table 1 was used instead of Compound 1. o o o o o o o o o o
Figure imgf000132_0002
상기 실험예 및 비교 실험예에서 제조한 유기 발광 소자에 전류를 인가하여， 구동 전압, 및 효율을 측정하고 그 결과를 하기 표 1에 나타내었다. 이때, 수명은 초기 휘도를 100%로 하였을 때 휘도가 95%로 감소하는데 소요되는 시간으로서 정의된다.
Figure imgf000132_0002
Current was applied to the organic light emitting device manufactured in the Experimental Example and Comparative Experimental Example to measure the driving voltage and efficiency, and the results are shown in Table 1 below. In this case, the lifetime is defined as the time required for the luminance to decrease to 95% when the initial luminance is set to 100%.
【표 1】  [Table 1]
정공 정공 전압 (V) 효율 (Cd/A) 색좌표 수명 (T95, h) 조절층 (@20mA/cm2) (@20mA/cm2) (x,y) (@20mA/cm2) 실험예 1-1 화합물 1 ΗΤ2 3.51 6.71 49.0 실험예 1—2 화합물 2 ΗΤ2 3.45 6.63 50.2 실험예 1-3 화합물 3 ΗΤ2 3.41 6.58 (0.135, 0.138) 55.2 실험예 1-4 화합물 4 ΗΤ2 3.52 6.57 (0.135, 0.138) 52.1 실험예 1-5 화합물 5 ΗΤ2 3.55 6.42 53.4 실험예 1-6 화합물 6 ΗΤ2 3.61 6.71 (0.134, 0.138) 55.1 실험예 1-7 화합물 7 ΗΤ2 3.31 6.52 (0.135, 0.138) 48.5 실험예 1-8 화합물 8 ΗΤ2 3.50 6.69 49.1 실험예 1-9 화합물 9 HT2 3.58 6.64 60.1 실험예 1-10 화합물 10 HT2 3.55 6.71 (0.135, 0.138) 57.4 실험예 1-11 화합물 11 HT2 3.61 6.58 55.8 실험예 1-12 화합물 12 HT2 3.67 6.48 56.2 실험예 1-13 화합물 13 HT2 3.34 6.82 (0.134 0.138) 51.2 실험예 1—14 화합물 14 HT2 3.42 6.72 (0.136, 0.139) 48.9 실험예 1-15 화합물 15 HT2 3.38 6.69 (0.136 0.139) 52.4 비교실험예 1-1 HT1 HT2 3.82 5.70 (0.134 0.139) 28.1 비교실험예 1-2 HT3 HT2 3.94 5.81 (0.135 0.138) 21.0 비교실험예 1-3 HT4 HT2 3.78 5.66 33.0 비교실험예 1-4 HT3 HT5 3.88 5.82 (0.136 0.139) 28.0 비교실험예 1-5 HT7 HT2 3.78 5.99 (0.135 0.138) 48.0 비교실험예 1-6 HT8 HT2 3.76 5.89 44.5 실험예 2-1 Precision holes voltage (V) Efficiency (Cd / A) color coordinate life (T95, h) controlling layer (@ 20mA / cm 2) ( @ 20mA / cm 2) (x, y) (@ 20mA / cm 2) Experiment 1 -1 Compound 1 ΗT2 3.51 6.71 49.0 Experimental Example 1-2 Compound 2 ΗΤ2 3.45 6.63 50.2 Experimental Example 1-3 Compound 3 ΗΤ2 3.41 6.58 (0.135, 0.138) 55.2 Experimental Example 1-4 Compound 4 ΗΤ2 3.52 6.57 (0.135, 0.138) 52.1 Experimental example 1-5 Compound 5? T? 2 3.55 6.42 53.4 Experimental example 1-6 Compound 6? H? 2 3.61 6.71 (0.134, 0.138) 55.1 Experimental example 1-7 Compound 7? H? 2 3.31 6.52 (0.135, 0.138) 8 ΗΤ2 3.50 6.69 49.1 Experimental Example 1-9 Compound 9 HT2 3.58 6.64 60.1 Experimental Example 1-10 Compound 10 HT2 3.55 6.71 (0.135, 0.138) 57.4 Experimental Example 1-11 Compound 11 HT2 3.61 6.58 55.8 Experimental Example 1-12 Compound 12 HT2 3.67 6.48 56.2 Experiment Example 1-13 Compound 13 HT2 3.34 6.82 (0.134 0.138) 51.2 Experimental Example 1-14 Compound 14 HT2 3.42 6.72 (0.136, 0.139) 48.9 Experimental Example 1-15 Compound 15 HT2 3.38 6.69 (0.136 0.139) 52.4 Comparative Experimental Example 1- 1 HT1 HT2 3.82 5.70 (0.134 0.139) 28.1 Comparative Experimental Example 1-2 HT3 HT2 3.94 5.81 (0.135 0.138) 21.0 Comparative Experimental Example 1-3 HT4 HT2 3.78 5.66 33.0 Comparative Experimental Example 1-4 HT3 HT5 3.88 5.82 (0.136 0.139) 28.0 Comparative Experimental Example 1-5 HT7 HT2 3.78 5.99 (0.135 0.138) 48.0 Comparative Experimental Example 1-6 HT8 HT2 3.76 5.89 44.5 Experimental Example 2-1
IT0 (인듐 주석 산화물)가 1,000 A 두께로 박막 코팅된 유리 기판 (corning 7059 glass)을， 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터 (Filter)로 2차 걸러진 증류수를 사용하였다.  A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 A was immersed in distilled water dissolved in a dispersant and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used.
o o o  she is she
ITO를 30분간 세척한 후， 증류수로 2회 반복하여 초음파 세척을 10분간 지 After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice
진행하였다. 증류수 세척이 끝난 후 이소프로필알콜， 아세 o o o o o톤， 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. 이렇게 준비된 IT0 투명 전극 위에 하기 HAT 화합물을 500 A의 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 그 위에 정공을 수송하는 물질인 하기 ΗΊΊ 화합물 (900A)을 진공 증착한 후， 이어서 상기 정공 수송층 위에 앞서 제조한 화합물 1을 막두께 50A으로 진공 증착하여 정공 조절층을 형성하였다. 상기 정공 조절층 상에 하기 HI 화합물 (호스트)과 하기 D1 화합물 (도판트)을 25:1의 중량비로 진공 증착하여 300 A 두께의 발광층을 형성하였다. 그 다음에 하기 E1 화합물 (300A)을 전자주입 및 수송층으로 순차적으로 열 진공 증착하였다. 상기 전자 수송층 위에 순차적으로 12A 두께의 리튬 플루오라이드 (LiF)와 2, 000 A 두께의 알루미늄을 증착하여 음극을 형성하여， 유기 발광 소자를 제조하였다. . After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, methanol solvent, and dried. The following HAT compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 A to form a hole injection layer. The following compound (900A), which is a material for transporting holes, was vacuum-deposited on the hole transport layer, and then the compound 1 prepared above was vacuum-deposited to a film thickness of 50 A on the hole transport layer to form a hole control layer. The following HI compound (host) and the following D1 compound (dopant) were vacuum deposited on the hole-transporting layer at a weight ratio of 25: 1 to form a 300 A thick light emitting layer. Then, the following E1 compound (300A) was sequentially vacuum deposited by electron injection and transport layer. Lithium fluoride (LiF) having a thickness of 12 A and aluminum having a thickness of 2,000 A were sequentially deposited on the electron transporting layer to form a cathode, thereby preparing an organic light emitting device.
Figure imgf000134_0001
Figure imgf000134_0001
Figure imgf000134_0002
Figure imgf000134_0002
상기의 과정에서 유기물의 증착 속도는 1 A/sec를 유지하였고， 리튬플루라이드는 0.2 A/sec, 알루미늄은 3 ~ 7 A/sec의 증착속도를 유지하였으며， 증착시 진공도는 1X10—7 ~ 5X10"8 torr를 유지하였다. 실험예 2-2내지 2-17 The deposition rate of the organic material in the above process was maintained at 1 A / sec, lithium fluoride is 0.2 A / sec, aluminum were deposited at speeds of 3 to 7 A / sec, During the deposition, a vacuum 1X10- 7 ~ 5X10 &Quot; 8 torr < / RTI > was maintained. Experimental Examples 2-2 to 2-17
상기 실험예 2—1과 동일한 방법으로 제조하되 , 화합물 1 대신 하기 표 2에 기재된 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 소자를 제조하였다. 비교실험예 2-1내지 2-6  An organic light emitting device was prepared in the same manner as in Experimental Example 2-1 except that the compound described in Table 2 was used instead of Compound 1. Comparative Experimental Examples 2-1 to 2-6
상기 실험예 2-1과 동일한 방법으로 제조하되 , 화합물 ΗΊ 및 화합물 1 대신 각각 하기 표 2에 기재된 화합물을 사용한 것을 제외하고는 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 2에서， HT3, HT4, HT5, HT6는 각각 하기와 같다. An organic light emitting device was prepared in the same manner as in Experimental Example 2-1, except that the compound described in Table 2 was used instead of the compound HΊ and Compound 1, respectively. In Table 2, HT3, HT4, HT5 and HT6 are as follows.
Figure imgf000135_0001
Figure imgf000135_0002
Figure imgf000135_0001
Figure imgf000135_0002
o o o  she is she
Figure imgf000135_0003
상기 실험예 및 비교 실험예에서 제조한 유기 발광 소자에 전류를 인가하여， 구동 전압， 및 효율을 측정하고 그 결과를 하기 표 2에 나타내었다. 이때， 수명은 초기 휘도를 100%로 하였을 때 휘도가 95%로 감소하는데 소요되는 시간으로서 정의된다.
Figure imgf000135_0003
Currents were applied to the organic light emitting devices manufactured in the Experimental Examples and Comparative Experimental Examples to measure the driving voltage and efficiency, and the results are shown in Table 2 below. In this case, the lifetime is defined as the time required for the luminance to decrease to 95% when the initial luminance is set to 100%.
【표 2]  [Table 2]
정공 정공 전압 (V) 효율 (Cd/A) 색좌표 수명 (T95, h) 조절층 (@20mA/cm2) (@20mA/cm2) (x,y) (@20mA/cm2) 실험예 2一 1 HT1 화합물 1 3.33 6.89 (0.135, 0.138) 52.0 실험예 2-2 HT1 화합물 2 3.43 6.78 (0.137, 0.134) 51.0 실험예 2-3 HT1 화합물 3 3.42 6.91 55.2 실험예 2-4 HT1 화합물 4 3.52 6.79 48.0 실험예 2-5 HT1 화합물 5 3.45 6.58 47. 1 실험예 2-6 HT1 화합물 6 3.39 6.81 49.7 실험예 2-7 HT1 화합물 7 3.55 7.01 50.5 실험예 2-8 HT1 화합물 8 3.49 6.89 53.5 실험예 2-9 HT1 화합물 9 3.51 6.71 50. 1 실험예 2-10 HT1 화합물 10 3.45 6.63 (0. 134， 0. 138) 49.8 실험예 2-11 HT1 화합물 11 3.41 6.58 47.4 실험예 2-12 HT1 화합물 12 3.39 6.81 49.7 실험예 2-13 HT1 화합물 13 3.41 6.88 51.2 실험예 2-14 HT1 화합물 14 3.52 6.68 49.8 실험예 2—15 HT1 화합물 15 3.39 6.82 49.7 실험예 2-16 화합물 10 화합물 5 3.67 7. 12 60. 1 실험예 2-17 화합물 1 화합물 11 3.71 7.08 59.1 비교실험예 2-1 HT1 HT5 3.82 5.71 33.5 비교실험예 2-2 HT3 HT5 3.78 5.89 28.2 비교실험예 2-3 HT1 HT6 3.75 5.91 35. 1 비교실험예 2-4 HT4 HT6 3.70 5.84 29.4 비교실험예 2—5 HT1 HT7 3.88 5.78 30. 1 비교실험예 2-6 HT1 HT8 3.78 5.88 (0.134 , 0.138) 32.5 본 발명에 따른 화학식의 화합물 유도체는 유기 발광 소자를 비롯한 기 전자 소자에서 정공 수송 및 정공조절 역할__■> < • ' ο o o o o o o o o o o o o o o o o을 할 수 있으며， 본 발명에 따른 소자 효율， 구동전압， 안정성 면에기기지서 우수한 특성을 ο ο o o o o o o o o o o o o o o Precision holes voltage (V) Efficiency (Cd / A) color coordinate life (T95, h) controlling layer (@ 20mA / cm 2) ( @ 20mA / cm 2) (x, y) (@ 20mA / cm 2) Experiment 2 HT1 Compound 1 3.33 6.89 (0.135, 0.138) 52.0 Experimental Example 2-2 HT1 Compound 2 3.43 6.78 (0.137, 0.134) 51.0 Experimental Example 2-3 HT1 Compound 3 3.42 6.91 55.2 Experimental Example 2-4 HT1 Compound 4 3.52 6.79 48.0 Experimental Example 2-5 HT1 Compound 5 3.45 6.58 47.1 Experimental Example 2-6 HT1 Compound 6 3.39 6.81 49.7 Experimental Example 2-7 HT1 Compound 7 3.55 7.01 50.5 Experimental Example 2-8 HT1 Compound 8 3.49 6.89 53.5 Experimental Example 2- 9 HT1 Compound 9 3.51 6.71 50.1 Experimental Example 2-10 HT1 Compound 10 3.45 6.63 (0. 134, 0. 138) 49.8 Experimental Example 2-11 HT1 Compound 11 3.41 6.58 47.4 Experimental Example 2-12 HT1 Compound 12 3.39 6.81 49.7 Experimental Example 2-13 HT1 Compound 13 3.41 6.88 51.2 Experimental Example 2-14 HT1 Compound 14 3.52 6.68 49.8 Experimental Example 2-15 HT1 Compound 15 3.39 6.82 49.7 Experimental Example 2-16 Compound 10 Compound 5 3.67 7. 12 60.1 Experimental Example 2-17 Compound 1 Compound 11 3.71 7.08 59.1 Comparative Test Example 2-1 HT1 HT5 3.82 5.71 33.5 Comparative Test Example 2-2 HT3 HT5 3.78 5.89 28.2 Comparative Test Example 2-3 HT1 HT6 3.75 5.91 35.1 Comparative Test Example 2-4 HT4 HT6 3.70 5.84 29.4 Comparative Test Example 2-5 HT1 HT7 3.88 5.78 30. 1 Comparative Test Example 2-6 HT1 HT8 3.78 5.88 (0.134, 0.138) 32.5 The compound derivative of the formula Hole-transporting and hole-control part in electrical and electronic devices, including __ ■><• a 'ο may be a oooooooooooooooo, device efficiency, driving voltage, and excellent device characteristics substation to the stability surface according to the invention ο ο oooooooooooooo
나타낸다. .
寸그  The
수수  Sorghum
【부호의 설명】  DESCRIPTION OF REFERENCE NUMERALS
기판
Figure imgf000136_0001
Board
Figure imgf000136_0001
발광층 으그  Light emitting layer
ᄆ ᅳ I  ᄆ ᅳ I
정공주입 정공수송층  Hole injection hole transport layer
발광층 전자수송층  The light emitting layer electron transporting layer

Claims

【특허청구범위】 【청구항 1】 하기 화학식 1로 표시되는 화합물: Claims: 1. A compound represented by the following formula (1):
[화학식 1]  [Chemical Formula 1]
Figure imgf000137_0001
Figure imgf000137_0001
상기 화학식 1에서，  In Formula 1,
Xi 내지 X4 중， ¾ 및 ¾ , ¾ 및 ¾ , 또는 ¾ 및 가 하기 화학식 2의 *와 각각 연결되고， 나머지는 수소이고，  / RTI &gt; and / or &lt; RTI ID = 0.0 &gt; and / or &lt; / RTI &
Figure imgf000137_0002
Figure imgf000137_0002
a , c , d 및 e는 0 내지 3의 정수이고，  a, c, d and e are integers of 0 to 3,
b는 0 내지 2의 정수이고，  b is an integer of 0 to 2,
X는 1 또는 2이고，  X is 1 or 2,
Ri 내지 R5는 각각 독립적으로 수소， 중수소， 할로겐， 시아노， 치환 또 비치환된 d-60 알킬， 치환 또는 비치환된 d-60 알콕시， 치환 또는 비치환된 d-60 티오알킬， 치환 또는 비치환된 C3-60 사이클로알킬， 치환 또는 비치환된 C6-60 아릴， 또는 트리오60 알킬)실릴이고, Ri to R 5 are each independently hydrogen, deuterium, halogen, cyano, substituted again unsubstituted d-60 alkyl, substituted or unsubstituted d- 60 alkoxy, substituted or unsubstituted d- 60 thioalkyl, substituted or unsubstituted C 3 - 60 cycloalkyl, substituted or unsubstituted C 6 - 60 aryl, or trio 60 alkyl) silyl, and,
R은 각각 독립적으로 하기 화학식 3으로 표시되고，  Each R independently represents a group represented by the following formula (3)
[화학식 3]  (3)
Figure imgf000137_0003
상기 화학식 3에서,
Figure imgf000137_0003
In Formula 3,
Li, L2 및 L3는 각각 독립적으로， 단일 결합; 치환 또는 비치환된 C6_ 60 아릴렌; 또는 치환 또는 비치환된 N, 0， 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴렌이고，Li, L 2 and L 3 are each independently a single bond; Substituted or unsubstituted C 6 _ 60 arylene; Or substituted or unsubstituted C 2 - 60 heteroarylene containing at least one hetero atom selected from the group consisting of N, O, and S,
An 및 Ar2는 각각 독립적으로 치환 또는 비치환된 C6-60 아릴; 또는 치환 또는 비치환된 N, 0， 및 S로 구성되는 군으로부터 선택되는 어느 하나 이상의 헤테로원자를 포함하는 C2-60 헤테로아릴이다. An and Ar 2 are each C independently represents a substituted or unsubstituted 6-60 aryl; Or substituted or unsubstituted C 2 -C 60 heteroaryl containing at least one hetero atom selected from the group consisting of N, O, and S.
【청구항 2】 [Claim 2]
게 1항에 있어서，  In Item 1,
상기 화학식 1은 하기 화학식 1-1， 1-2, 또는 1-3으로 표시되는， 화합물: ·  Wherein the compound represented by Formula 1 is represented by the following Formula 1-1, 1-2, or 1-3:
[화학식 1-1]  [Formula 1-1]
Figure imgf000138_0001
Figure imgf000138_0001
[화학식 1-3] [Formula 1-3]
Figure imgf000139_0001
Figure imgf000139_0001
【청구항 3】 [Claim 3]
제 1항에 있어서，  The method according to claim 1,
a, b , c , d 및 e는 0인，  a, b, c, d and e are 0,
화합물.  compound.
【청구항 4】 Claim 4
제 1항에 있어서，  The method according to claim 1,
' 은 단일 결합, 페닐렌， 비페닐디일, 터페닐디일， 쿼터페닐디일, 나프탈렌디일， 안트라센디일， 페난쓰렌디일, 트리페닐렌디일， 피렌디일， 디메틸플루오렌디일， 메틸페닐플루오렌디일, 디페닐플루오렌디일， 디벤조퓨란디일， 디벤조티오펜디일， 카바졸디일， 또는 9-페닐 -9H- 카바졸디일인, May be a single bond, a single bond, a single bond such as phenylene, biphenyl diyl, terphenyl diyl, quaterphenyl diyl, naphthalenediyl, anthracenediyl, phenanthrenediyl, triphenylene diyl, pyrandiyl, dimethylfluorenediyl, methylphenylfluorenediyl, Fluorenyl, dibenzofurandiyl, dibenzothiophenediyl, carbazolyl, or 9-phenyl-9H-carbazolyl,
화합물.  compound.
[청구항 5】 [Claim 5]
게 1항에 있어서，  In Item 1,
및 L3은 각각 독립적으로 단일 결합， 페닐렌, 비페닐디일, 터페닐디일， 쿼터페닐디일， 나프탈렌디일， 안트라센디일， 페난쓰렌디일, 트리페닐렌디일， 피렌디일， 디메틸플루오렌디일， 메틸페닐플루오렌디일， 디페닐플루오렌디일, 스피로플루오렌디일， 디벤조퓨란디일, 디벤조티오펜디일， 카바졸디일， 또는 9-페닐 -9H-카바졸디일인， And L &lt; 3 &gt; are each independently selected from the group consisting of a single bond, phenylene, biphenyldiyl, terphenyldiyl, quaterphenyldiyl, naphthalenediyl, anthracenediyl, phenanthrenediyl, triphenylene- Or a 9-phenyl-9H-carbazoyldiiyl, which is optionally substituted with one or more substituents selected from the group consisting of halogen, fluorine, fluorine, fluorine, fluorine,
화합물. compound.
【청구항 6] [Claim 6]
게 1항에 있어서，  In Item 1,
A 및 Ar2는 각각 독립적으로 페닐， 비페닐릴， 터페닐릴， 쿼터페닐릴， 나프틸, 페난쓰레닐， 디메틸플루오레닐， 디벤조플루오레닐， 스피로플루오레닐， 디벤조퓨라닐， 디벤조티오페닐， 카바졸릴， 또는 9-페닐- 9H-카바졸릴인, A and Ar 2 are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, dimethylfluorenyl, dibenzofluorenyl, spirofluorenyl, dibenzofuranyl, Dibenzothiophenyl, carbazolyl, or 9-phenyl-9H-carbazolyl,
화합물 ·  Compound
【청구항 7】 7.
제 1항에 있어서,  The method according to claim 1,
상기 화학식 1로 표시되는 화합물은 하기로 구성되는 군으로부터 선택되는 어느 하나인，  The compound represented by the formula (1) is any one selected from the group consisting of
화합물: compound:
O T O T
Figure imgf000141_0001
Figure imgf000141_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000142_0001
Figure imgf000142_0001
CZt'900/8lOra¾13d CZt'900 / 8lOra¾13d
Figure imgf000143_0001
Figure imgf000143_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000144_0001
Figure imgf000144_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000145_0001
Figure imgf000145_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000146_0001
Figure imgf000146_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV 9Π £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV 9Π
Figure imgf000147_0001
Figure imgf000147_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000148_0001
Figure imgf000148_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000149_0001
Figure imgf000149_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000150_0001
Figure imgf000150_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV OST CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV OST
Figure imgf000151_0001
Figure imgf000151_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV T9I
Figure imgf000152_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV T9I
Figure imgf000152_0001
Figure imgf000152_0002
Figure imgf000152_0002
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV Z 1 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Z 1
Figure imgf000153_0001
Figure imgf000153_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV C9I CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV C9I
Figure imgf000154_0001
Figure imgf000154_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000155_0001
Figure imgf000155_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000156_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000156_0001
Figure imgf000157_0001
Figure imgf000157_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV Λ9Ι CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Λ9Ι
Figure imgf000158_0001
Figure imgf000158_0001
e^^900/8lOZHM/X3d 851 e ^^ 900 / 8lOZHM / X3d 851
Figure imgf000159_0001
Figure imgf000159_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 6SI CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 6SI
Figure imgf000160_0001
Figure imgf000160_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000161_0001
Figure imgf000161_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 191 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 191
Figure imgf000162_0001
Figure imgf000162_0001
£Jl7900/8l0raM/X3d ε»8Ζ·0/6ΪΟί OAV Z91 £ Jl 7 900 / 8l0raM / X3d ε »8ZD · 0 / 6ΪOΟ OAV Z91
Figure imgf000163_0001
C9T
Figure imgf000164_0001
Figure imgf000163_0001
C9T
Figure imgf000164_0001
Figure imgf000164_0002
Figure imgf000164_0002
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000165_0001
Figure imgf000165_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV 991 £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV 991
Figure imgf000166_0001
Figure imgf000166_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 991 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 991
Figure imgf000167_0001
Figure imgf000167_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV Z9I CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Z9I
Figure imgf000168_0001
Figure imgf000168_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 891 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 891
Figure imgf000169_0001
Figure imgf000169_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 691 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 691
Figure imgf000170_0001
Figure imgf000170_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV OLl CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV OLl
Figure imgf000171_0001
Figure imgf000171_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV ILl CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV ILl
Figure imgf000172_0001
Figure imgf000172_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV ZLl CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV ZLl
Figure imgf000173_0001
Figure imgf000173_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000174_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000174_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000175_0001
Figure imgf000175_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV I CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV I
Figure imgf000176_0001
Figure imgf000176_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 9 I CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 9 I
Figure imgf000177_0001
Figure imgf000177_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV LLl CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV LLl
Figure imgf000178_0001
Figure imgf000178_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000179_0001
Figure imgf000179_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000180_0001
Figure imgf000180_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 081 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 081
Figure imgf000181_0001
Figure imgf000181_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV I8T CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV I8T
Figure imgf000182_0001
Figure imgf000182_0001
e^^900/8lOZHM/X3d Z8I e ^^ 900 / 8lOZHM / X3d Z8I
Figure imgf000183_0001
Figure imgf000183_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000184_0001
Figure imgf000184_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000185_0001
Figure imgf000185_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV S8I £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV S8I
Figure imgf000186_0001
Figure imgf000186_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 981 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 981
Figure imgf000187_0001
Figure imgf000187_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV Z8I CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Z8I
Figure imgf000188_0001
Figure imgf000188_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 881 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 881
Figure imgf000189_0001
CZl7900/8lOZaM/X3d 681
Figure imgf000189_0001
CZl7900 / 8lOZaM / X3d 681
Figure imgf000190_0001
Figure imgf000190_0001
Cl1-900/8lOra¾/X3d ε»8/<0/6Ι0Ζ O 061 Cl1-900 / 8lOra 占 / X3d? 8 / <0/6? I O Z O 061
Figure imgf000191_0001
Figure imgf000191_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 161 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 161
Figure imgf000192_0001
Figure imgf000192_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000193_0001
Figure imgf000193_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV S6T CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV S6T
Figure imgf000194_0001
Figure imgf000194_0001
Figure imgf000194_0002
Figure imgf000194_0002
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000195_0001
Figure imgf000195_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV 961 £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV 961
Figure imgf000196_0001
Figure imgf000196_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 961 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 961
Figure imgf000197_0001
Figure imgf000197_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000198_0001
Figure imgf000198_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000199_0001
Figure imgf000199_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000200_0001
Figure imgf000200_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV ooz CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV ooz
Figure imgf000201_0001
Figure imgf000201_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000202_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000202_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV zoz CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV zoz
Figure imgf000203_0001
Figure imgf000203_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000204_0001
Figure imgf000204_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000205_0001
Figure imgf000205_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000206_0001
Figure imgf000206_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000207_0001
Figure imgf000207_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000208_0001
Figure imgf000208_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000209_0001
Figure imgf000209_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000210_0001
Figure imgf000210_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 012 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 012
Figure imgf000211_0001
Figure imgf000211_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000212_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000212_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000213_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000213_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000214_0001
Figure imgf000214_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000215_0001
Figure imgf000215_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 9IZ CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 9IZ
Figure imgf000216_0001
Figure imgf000216_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 9X2 CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 9X2
Figure imgf000217_0001
Figure imgf000217_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000218_0001
Figure imgf000218_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000219_0001
Figure imgf000219_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000220_0001
Figure imgf000220_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV ozz CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV ozz
Figure imgf000221_0001
Figure imgf000221_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000222_0001
Figure imgf000222_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV zzz CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV zzz
Figure imgf000223_0001
Figure imgf000223_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000224_0001
Figure imgf000224_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV
Figure imgf000225_0001
CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000225_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000226_0001
Figure imgf000226_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 9ZZ CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 9ZZ
Figure imgf000227_0001
Figure imgf000227_0001
£Zt900/ lOZ i/lDd e 8Z,0/6T0∑; OAV £ Zt900 / lOZ i / lDd e 8Z, 0 / 6T0Σ; OAV
Figure imgf000228_0001
Figure imgf000228_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000229_0001
Figure imgf000229_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 6ZZ CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 6ZZ
Figure imgf000230_0001
Figure imgf000230_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 0£Z CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV 0 £ Z
Figure imgf000231_0001
Figure imgf000231_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000232_0001
Figure imgf000232_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000233_0001
Figure imgf000233_0001
Figure imgf000233_0002
Figure imgf000233_0002
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000234_0001
Figure imgf000234_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV
Figure imgf000235_0001
Figure imgf000235_0001
£Z 900/8lOZW^/13d ε»8Ζ·0/6ΪΟΖ OAV £ Z 900 / 8lOZW ^ / 13d ε »8ZD · 0 / 6ΪOZ OAV
Figure imgf000236_0001
Figure imgf000236_0001
CZl7900/8lOZaM/X3d ε»8Ζ·0/6ΪΟΖ OAV 거 U 전극; 상기 게 1 전극과 대향하여 구비된 제 2 전극; 및 상기 거 U 전극과 상기 게 2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서， 상기 유기물층 중 1층 이상은 제 1항 내지 제 7항 중 어느 하나의 항에 따른 화합물을 포함하는 것인， 유기 발광 소자. CZl7900 / 8lOZaM / X3d ε »8ZD · 0 / 6ΪΟΖ OAV Gau electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the U electrode and the second electrode, wherein at least one of the organic compound layers includes the compound according to any one of claims 1 to 7 The organic light-emitting device.
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