KR20130011955A - Novel organic electroluminescence compounds and organic electroluminescence device using the same - Google Patents

Novel organic electroluminescence compounds and organic electroluminescence device using the same Download PDF

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KR20130011955A
KR20130011955A KR1020120078704A KR20120078704A KR20130011955A KR 20130011955 A KR20130011955 A KR 20130011955A KR 1020120078704 A KR1020120078704 A KR 1020120078704A KR 20120078704 A KR20120078704 A KR 20120078704A KR 20130011955 A KR20130011955 A KR 20130011955A
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substituted
compound
unsubstituted
alkyl
aryl
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KR1020120078704A
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김치식
김희숙
이효정
김혜미
문두현
황수진
이선우
양수진
이수현
이경주
신효님
박경진
조영준
권혁주
김봉옥
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롬엔드하스전자재료코리아유한회사
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Priority to JP2014521569A priority Critical patent/JP2014521604A/en
Priority to CN201280045815.0A priority patent/CN104039778A/en
Priority to TW101126210A priority patent/TW201307335A/en
Priority to PCT/KR2012/005841 priority patent/WO2013012298A1/en
Publication of KR20130011955A publication Critical patent/KR20130011955A/en

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Abstract

PURPOSE: A novel organic light emitting compound and an organic electroluminescent device containing the same are provided to enhance light emitting efficiency and to prepare an OLED device with improved power consumption. CONSTITUTION: A novel organic light emitting compound is denoted by chemical formula 1. An organic electroluminescent device contains the compound. The organic electroluminescent device comprises: a first electrode, a second electrode, one or more organic layer inserted between the first and second electrodes. The organic layer contains one or more compound of chemical formula 1.

Description

신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자{Novel organic electroluminescence compounds and organic electroluminescence device using the same}Novel organic electroluminescence compounds and organic electroluminescence device using the same

본 발명은 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계 발광 소자 에 관한 것이다.The present invention relates to a novel organic light emitting compound and an organic electroluminescent device comprising the same.

표시 소자 중, 전계 발광 소자(electroluminescence device: EL 소자)는 자체 발광형 표시 소자로서 시야각이 넓고 콘트라스트가 우수할 뿐만 아니라 응답속도가 빠르다는 장점을 가지고 있다. 1987년 이스트만 코닥(Eastman Kodak)사는 발광층 형성용 재료로서 저분자인 방향족 디아민과 알루미늄 착물을 이용하고 있는 유기 EL 소자를 처음으로 개발하였다[Appl. Phys. Lett. 51, 913, 1987].Among the display elements, an electroluminescence device (EL element) is a self-luminous display element and has advantages of wide viewing angle, excellent contrast and fast response speed. In 1987, Eastman Kodak developed for the first time an organic EL device using a low molecular weight aromatic diamine and an aluminum complex as a material for forming a light emitting layer [Appl. Phys. Lett. 51, 913, 1987].

유기 EL 소자에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 발광 재료가 널리 사용되고 있으나, 전계 발광의 메커니즘상 인광 발광 재료가 형광 발광 재료에 비해 이론적으로 4배까지 발광 효율을 개선시킬 수 있다는 점에서 인광 발광 재료의 개발 연구가 널리 수행되고 있다. 현재까지 이리듐(III)착물 계열이 인광 발광 재료로 널리 알려져 있으며, 각 RGB 별로는 (acac)Ir(btp)2(비스(2-(2'-벤조티에닐)-피리디네이토-N,C-3')이리듐(아세틸아세토네이트)), Ir(ppy)3(트리스(2-페닐피리딘)이리듐) 및 Firpic (비스(4,6-디플루오로페닐피리디네이토-N,C2)피콜리네이토이리듐) 등의 재료가 알려져 있다.The most important factor that determines the luminous efficiency in the organic EL device is the light emitting material. Fluorescent light emitting materials are widely used as the light emitting materials. However, researches on the development of phosphorescent light emitting materials are widely used in that phosphorescent light emitting materials can theoretically improve light emission efficiency by four times compared to fluorescent light emitting materials due to the mechanism of electroluminescence. Is being performed. To date, iridium (III) complexes are widely known as phosphorescent materials, and for each RGB, (acac) Ir (btp) 2 (bis (2- (2'-benzothienyl) -pyridinate-N, C -3 ') Iridium (acetylacetonate)), Ir (ppy) 3 (tris (2-phenylpyridine) iridium) and Firpic (bis (4,6-difluorophenylpyridinate-N, C2) Materials, such as colonine to iridium), are known.

발광 재료는 색순도, 발광효율 및 안정성을 향상시키기 위해 호스트 재료와 도펀트를 혼합한 도펀트/호스트재료의 체계로 사용하기도 한다. 이와 같은 체계를 사용할 때, 호스트 재료는 발광 소자의 효율과 성능에 큰 영향을 미치므로, 그 선택이 중요하다. 종래 기술에서, 인광용 호스트 재료로는 4,4’-비스(카바졸-9-일)-비페닐(CBP)이 가장 널리 알려져 있었다. 최근에는, 일본의 파이오니어 등이 정공 저지층의 재료로 사용되던 바토큐프로인(Bathocuproine, BCP) 및 알루미늄(III)비스(2-메틸-8-퀴놀리네이트)(4-페닐페놀레이트)(Balq) 등을 호스트 재료로 이용해 고성능의 유기 EL 소자를 개발한 바 있다.The light emitting material may also be used as a dopant / host material system in which a host material and a dopant are mixed to improve color purity, luminous efficiency and stability. When using such a scheme, the host material has a great influence on the efficiency and performance of the light emitting device, so the selection is important. In the prior art, 4,4'-bis (carbazol-9-yl) -biphenyl (CBP) was the most widely known phosphorescent host material. Recently, Batocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenylphenolate), in which Pioneer et al., Japan, were used as a material for the hole blocking layer, He developed a high-performance organic EL device using Balq) as a host material.

그러나 기존의 이러한 인광용 호스트 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 다음과 같은 단점이 있다: (1) 유리 전이 온도가 낮고 열적 안정성이 낮아서, 진공 하에서 고온 증착 공정을 거칠 때, 물질이 변한다. (2) 유기 EL 소자에서 전력효율 = [(π/전압) × 전류효율]의 관계에 있으므로 전력 효율은 전압에 반비례한다. 그러나, 인광용 호스트 재료를 사용한 유기 EL 소자는 형광 재료를 사용한 유기 EL 소자에 비해 전류 효율(cd/A)은 높으나, 구동 전압 역시 상당히 높기 때문에 전력 효율(lm/w) 면에서 큰 이점이 없다. (3) 또한, 유기 EL 소자에 사용할 경우, 작동 수명 측면에서도 만족스럽지 못하며, 발광 효율도 여전히 개선이 요구된다.However, existing phosphorescent host materials have advantages in terms of luminescence properties, but have the following disadvantages: (1) The glass transition temperature is low and the thermal stability is low, so that the material changes when subjected to a high temperature deposition process under vacuum. . (2) Since the power efficiency = [(π / voltage) x current efficiency] in the organic EL device, the power efficiency is inversely proportional to the voltage. However, the organic EL device using the phosphorescent host material has a higher current efficiency (cd / A) than the organic EL device using the fluorescent material, but the driving voltage is also very high, so there is no great advantage in terms of power efficiency (lm / w). . (3) Also, when used in an organic EL element, it is not satisfactory in terms of operating life, and the luminous efficiency is still required to be improved.

한편, 한국특허공보 제 KR0948700호에는 아릴카바졸기 골격에 질소를 포함하는 헤테로아릴이 치환된 유기전기발광 소자용 화합물을 언급하고 있다. 그러나 상기문헌에는 카바졸골격의 3번 위치에 방향족 고리가 융합된 헤테로시클로알킬 또는 시클로알킬기가 치환되고, 9번 위치에 치환 또는 비치환된 헤테로아릴이 직접 또는 간접적으로 연결된 화합물을 구체적으로 개시하고 있지 않다. Meanwhile, Korean Patent Publication No. KR0948700 refers to a compound for an organic electroluminescent device in which a heteroaryl containing nitrogen is substituted in an arylcarbazole group skeleton. However, the above documents specifically disclose compounds in which a heterocycloalkyl or cycloalkyl group in which an aromatic ring is fused at position 3 of a carbazole skeleton is substituted, and in which the substituted or unsubstituted heteroaryl at position 9 is directly or indirectly connected. Not.

한국특허공보 제 KR0948700호 (2010.03.12)Korean Patent Publication No. KR0948700 (2010.03.12)

Appl. Phys. Lett. 51, 913, 1987Appl. Phys. Lett. 51, 913, 1987

따라서 본 발명의 목적은 첫째로, 상기한 문제점들을 해결하기 위하여 기존의 재료보다 발광 효율 및 소자 수명이 좋으며, 적절한 색좌표를 갖는 우수한 골격의 유기 발광 화합물을 제공하는 것이며 둘째로, 상기 유기 발광 화합물을 발광 재료로서 채용하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic light emitting compound having excellent luminous efficiency and device life, and having an appropriate color coordinate, in order to solve the above problems, and secondly, to solve the above organic light emitting compound. It is to provide a high efficiency and long life organic electroluminescent element employed as a light emitting material.

상기의 기술적 과제를 해결하기 위해 예의 연구한 결과, 본 발명자들은 하기 화학식 1로 표시되는 유기발광 화합물이 상술한 목적을 달성함을 발견하여 본 발명을 완성하였다.As a result of intensive studies to solve the above technical problems, the present inventors have found that an organic luminescent compound represented by the following general formula (1) achieves the above-mentioned object and completed the present invention.

[화학식 1] [Formula 1]

Figure pat00001
Figure pat00001

상기 화학식 1에서, In Formula 1,

L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (3-30원)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C6-C30)시클로알킬렌이고; L 1 and L 2 are each independently a single bond, a substituted or unsubstituted (3- to 30-membered) heteroarylene, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (C6-C30 ) Cycloalkylene;

X1 및 X2은각각 독립적으로 CR' 또는 N이며; X 1 and X 2 are each independently CR ′ or N;

Y은 -O-, -S-, -CR5R6- 또는 -NR7-이고; Y is -O-, -S-, -CR 5 R 6 -or -NR 7- ;

Ar1, Ar2 및 R'는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고; Ar 1 , Ar 2 and R ′ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3 -30 membered) heteroaryl;

R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (5-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17, 시아노, 나이트로 또는 하이드록시이고, 인접한 치환체와 함께 단일환 또는 다환의 (C5-C30) 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R 1 to R 4 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (5- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl,- NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17, cyano, nitro or hydroxy, and monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring with adjacent substituents And carbon atoms of the alicyclic or aromatic ring formed may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur;

R5 내지 R7 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (5-7원)헤테로시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 함께 단일환 또는 다환의 (C5-C30) 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R 5 to R 7 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) heteroaryl, substituted or unsubstituted (5- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C3-C30) cycloalkyl, or monocyclic or polycyclic (C5- C30) may form an alicyclic or aromatic ring, wherein the carbon atoms of the formed alicyclic or aromatic ring may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur;

a 및 c는 각각 독립적으로 1 내지 4의 정수이며, a 또는 c가 2 이상의 정수인 경우 각각의 R1 또는 각각의 R3은 동일하거나 상이할 수 있고; a and c are each independently an integer of 1 to 4, and when a or c is an integer of 2 or more, each R 1 or each R 3 may be the same or different;

b 및 d는 각각 독립적으로 1 내지 3의 정수이며, b 또는 d가 2 이상의 정수인 경우 각각의 R2 또는 각각의 R4는 동일하거나 상이할 수 있고; b and d are each independently integers of 1 to 3, and when b or d is an integer of 2 or more, each R 2 or each R 4 may be the same or different;

상기 헤테로아릴렌, 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.The heteroarylene, heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.

본 발명에 따른 유기 발광 화합물은 발광 효율이 좋고 재료의 수명특성이 뛰어나 소자의 구동수명이 매우 우수한 OLED 소자를 제조할 수 있는 장점이 있다. 또한, 본 발명에 따른 유기 전자재료용 화합물은 전자전달 효율이 높아 소자 제작시 결정화를 방지할 뿐만 아니라 층 형성이 양호하여 소자의 전류특성을 개선시킴으로서 소자의 구동전압을 저하시키고 동시에 전력효율이 향상된 OLED 소자를 제조할 수 있는 장점이 있다.The organic light emitting compound according to the present invention has the advantage of being able to manufacture an OLED device having a good luminous efficiency and excellent life characteristics of the material and excellent driving life of the device. In addition, the compound for an organic electronic material according to the present invention has high electron transfer efficiency, which prevents crystallization during device fabrication and improves current characteristics of the device due to good layer formation, thereby lowering the driving voltage of the device and improving power efficiency. There is an advantage to manufacture an OLED device.

이하에서 본 발명을 더욱 상세히 설명하나, 이는 설명을 위한 것으로 본 발명의 범위를 제한하는 방법으로 해석되어서는 안 된다. Hereinafter, the present invention will be described in more detail, but this is for explanation and should not be construed as a method of limiting the scope of the present invention.

본 발명은 상기 화학식 1로 표시되는 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic light emitting compound represented by Chemical Formula 1 and an organic electroluminescent device including the same.

본 발명에 기재되어 있는 “(C1-C30)알킬”은 탄소수가 1 내지 30개인 직쇄 또는 분지쇄 알킬을 의미하고, 여기에서 탄소수가 1 내지 20개인 것이 바람직하고, 1 내지 10개인 것이 더 바람직하다. 상기 알킬의 구체적인 예로서, 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸 및 3급-부틸 등이 있다. 본원에서 “(C2-C30)알케닐”은 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알케닐을 의미하고, 여기에서 탄소수가 2 내지 20개인 것이 바람직하고, 2 내지 10개인 것이 더 바람직하다. 상기 알케닐의 구체적인 예로서, 비닐, 1-프로페닐, 2-프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 2-메틸부트-2-에닐 등이 있다. 본원에서 “(C2-C30)알키닐”은 탄소수가 2 내지 30개인 직쇄 또는 분지쇄 알키닐을 의미하고, 여기에서 탄소수가 2 내지 20개 인 것이 바람직하고, 2 내지 10개인 것이 더 바람직하다. 상기 알키닐의 예로서, 에티닐, 1-프로피닐, 2-프로피닐, 1-부티닐, 2-부티닐, 3-부티닐, 1-메틸펜트-2-이닐 등이 있다. 본원에서 “(C3-C30)시클로알킬”은 탄소수가 3 내지 30개인 단일환 또는 다환 탄화수소를 의미하고, 여기에서 탄소수가 3 내지 20개인 것이 바람직하고, 3 내지 7개인 것이 더 바람직하다. 상기 시클로알킬의 예로서, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등이 있다. 본원에서 “(C6-C30)시클로알킬렌”은 탄소수가 6 내지 30개인 시클로알킬에서 수소원자가 하나 더 제거된 것이고, 여기에서 탄소수가 6 내지 20개인 것이 바람직하고, 6 내지 12개인 것이 더 바람직하다. 본원에서 “(3-7원) 헤테로시클로알킬”은 환 골격 원자수가 3 내지 7개이고, B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자, 바람직하게는 O, S 및 N에서 선택되는 하나 이상의 헤테로원자를 포함하는 시클로알킬을 의미하고, 예를 들어, 테트라히드로푸란, 피롤리딘, 티올란, 테트라히드로피란 등이 있다. 본원에서 “(C6-C30)아릴(렌)”은 탄소수가 6 내지 30개인 방향족 탄화수소에서 유래된 단일환 또는 융합환계 라디칼을 의미하고, 여기에서 환 골격 탄소수가 6 내지 20개인 것이 바람직하고, 6 내지 15개인 것이 더 바람직하다. 상기 아릴의 예로서, 페닐, 비페닐, 터페닐, 나프틸, 플루오레닐, 페난트레닐, 안트라세닐, 인데닐, 트리페닐레닐, 피레닐, 테트라세닐, 페릴레닐, 크라이세닐, 나프타세닐, 플루오란테닐 등이 있다. 본원에서 “(3-30원) 헤테로아릴(렌)”은 환 골격 원자수가 3 내지 30개이고, B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자를 포함하는 아릴 기를 의미한다. 여기에서 환 골격 원자수가 5 내지 20개인 것이 바람직하고, 5 내지 15개인 것이 더 바람직하다. 헤테로원자수는 바람직하게는 1 내지 4개이고, 단일 환계이거나 하나 이상의 벤젠환과 축합된 융합환계일 수 있으며, 부분적으로 포화될 수도 있다. 또한, 본원에서 상기 헤테로아릴(렌)은 하나 이상의 헤테로아릴 또는 아릴기가 단일 결합에 의해 헤테로아릴기와 연결된 형태도 포함한다. 상기 헤테로아릴의 예로서, 푸릴, 티오펜일, 피롤릴, 이미다졸릴, 피라졸릴, 티아졸릴, 티아디아졸릴, 이소티아졸릴, 이속사졸릴, 옥사졸릴, 옥사디아졸릴, 트리아진일, 테트라진일, 트리아졸릴, 테트라졸릴, 푸라잔일, 피리딜, 피라진일, 피리미딘일, 피리다진일 등의 단일 환계 헤테로아릴, 벤조푸란일, 벤조티오펜일, 이소벤조푸란일, 디벤조푸란일, 디벤조티오펜일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인다졸릴, 벤조티아디아졸릴, 퀴놀릴, 이소퀴놀릴, 신놀리닐, 퀴나졸리닐, 퀴녹살리닐, 카바졸릴, 페녹사진일, 페난트리딘일, 벤조디옥솔릴 등의 융합 환계 헤테로아릴 등이 있다. 본원에서 “할로겐”은 F, Cl, Br 및 I 원자를 포함한다.“(C 1 -C 30) alkyl” described in the present invention means straight or branched chain alkyl having 1 to 30 carbon atoms, and preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. . Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. As used herein, "(C2-C30) alkenyl" means a straight or branched chain alkenyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. As used herein, "(C2-C30) alkynyl" means straight or branched chain alkynyl having 2 to 30 carbon atoms, preferably 2 to 20 carbon atoms, more preferably 2 to 10 carbon atoms. Examples of the alkynyl include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. As used herein, "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. As used herein, "(C6-C30) cycloalkylene" is one from which hydrogen atoms are further removed from cycloalkyl having 6 to 30 carbon atoms, preferably having 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. . As used herein, “(3-7 membered) heterocycloalkyl” has 3 to 7 ring skeleton atoms, and at least one heteroatom selected from the group consisting of B, N, O, S, P (═O), Si and P, Preferred are cycloalkyls comprising at least one heteroatom selected from O, S and N, for example tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. As used herein, "(C6-C30) aryl (ene)" means a monocyclic or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein 6 to 20 ring skeleton carbon atoms are preferable, and 6 More preferably 15. Examples of such aryls include phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, , Fluoranthenyl, and the like. As used herein, “(3- to 30-membered) heteroaryl (ene)” has 3 to 30 ring skeleton atoms, and at least one hetero selected from the group consisting of B, N, O, S, P (═O), Si and P It means an aryl group containing an atom. Here, the number of the atoms of the ring skeleton is preferably 5 to 20, more preferably 5 to 15. The number of heteroatoms is preferably 1 to 4, and may be a single ring system or a fused ring system condensed with one or more benzene rings, and may be partially saturated. In addition, the heteroaryl (ene) herein also includes a form in which one or more heteroaryl or an aryl group is connected to a heteroaryl group by a single bond. Examples of the heteroaryl include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxdiazolyl, triazinyl, tetrazinyl Monocyclic heteroaryl such as triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzooxazolyl, isoindoleyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, shin Fused ring heteroaryl such as nolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenantridinyl, and benzodioxolyl. "Halogen" herein includes F, Cl, Br and I atoms.

또한 본 발명에 기재되어 있는 “치환 또는 비치환”이라는 기재에서 ‘치환’은 어떤 작용기에서 수소 원자가 다른 원자 또는 다른 작용기 (즉, 치환체)로 대체되는 것을 뜻한다. 상기 화학식 1의 L1, L2, R', Ar1, Ar2, R1 내지 R4, R5 내지 R7 및 R11 내지 R17에서 치환 알킬, 치환 아릴(렌), 치환 헤테로아릴(렌), 치환 시클로알킬(렌), 치환 헤테로시클로알킬 및 치환 아랄킬의 치환체는 각각 독립적으로 중수소, 할로겐, 할로겐으로 치환되거나 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴로 치환되거나 비치환된 (3-30원)헤테로아릴, (C3-C30)시클로알킬, (5-7원)헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미한다.In addition, in the description of "substituted or unsubstituted" described in the present invention, 'substituted' means that a hydrogen atom is replaced by another atom or another functional group (ie, a substituent) in a certain functional group. In Formula 1, L 1 , L 2 , R ′, Ar 1 , Ar 2 , R 1 to R 4 , R 5 to R 7 and R 11 to R 17 , substituted alkyl, substituted aryl (ene), substituted heteroaryl ( And substituents of substituted cycloalkyl (ene), substituted heterocycloalkyl and substituted aralkyl are each independently (C 1 -C 30) alkyl, (C 6 -C 30) aryl, unsubstituted or substituted with deuterium, halogen, halogen ( (3- to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, (5- to 7-membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6) -C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2-C30) alky Nyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30) arylbo Ronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) alkyl ( C6-C30) aryl, carboxyl, nitro And it means one or more selected from the group consisting of hydroxy.

상기 화학식 1에서, 상기 L1 및 L2은 각각 독립적으로 단일결합, (3-30원)헤테로아릴렌, 또는 (C6-C30)아릴렌이고; X1 및 X2은 각각 독립적으로 CR' 또는 N이며; Y은 -O-, -S-, -CR5R6- 또는 -NR7-이고; Ar1, Ar2 및R'은 각각 독립적으로 수소, (C1-C30)알킬, (C6-C30)아릴, 또는 (3-30원)헤테로아릴이며; R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (3-30원)헤테로아릴, -NR11R12 또는 -SiR13R14R15이고, 상기 R3은 인접한 치환체와 함께 단일환 또는 다환의 (C5-C30) 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R5 내지 R7 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, 또는 (3-30원)헤테로아릴이고; 상기 L1및 L2의 아릴렌 및 헤테로아릴렌, Ar1, Ar2, R', R1 내지 R4, R5 내지 R7 및 R11 내지 R17의 알킬, 아릴 및 헤테로아릴은 각각 중수소, 할로겐, 할로겐으로 치환되거나 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴로 치환되거나 비치환된 (3-30원)헤테로아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노 및(C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.In Formula 1, L 1 and L 2 are each independently a single bond, a (3- to 30-membered) heteroarylene, or (C6-C30) arylene; X 1 and X 2 are each independently CR ′ or N; Y is -O-, -S-, -CR 5 R 6 -or -NR 7- ; Ar 1 , Ar 2 and R ′ are each independently hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, or (3-30 membered) heteroaryl; R 1 to R 4 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (3- to 30-membered) heteroaryl, —NR 11 R 12 or —SiR 13 R 14 R 15 , R 3 may form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring with adjacent substituents, wherein the carbon atoms of the formed alicyclic or aromatic rings are selected from nitrogen, oxygen and sulfur Can be replaced with one or more heteroatoms; R 5 to R 7 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, or (3--30 membered) heteroaryl; The arylene and heteroarylene of L 1 and L 2 , Ar 1 , Ar 2 , R ′, alkyl, aryl and heteroaryl of R 1 to R 4 , R 5 to R 7 and R 11 to R 17 are deuterium, respectively. (C1-C30) alkyl unsubstituted or substituted with halogen, halogen, (C6-C30) aryl, (3- to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, tri (C1-C30) Alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, N-carbazolyl, di ( At least one selected from the group consisting of C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino and (C1-C30) alkyl (C6-C30) aryl It may be further substituted with a substituent.

상기 화학식 1에서, 상기 L1 및 L2은 바람직하게는 각각 독립적으로 단일결합, (3-20원)헤테로아릴렌, 또는 (C6-C20)아릴렌이고, 상기 아릴렌은 (C1-C10)알킬 또는 (C6-C20)아릴로 더 치환될 수 있다. 상기 X1 및 X2은 각각 독립적으로 CR' 또는 N이며, 여기에서 R'는 바람직하게는 (C6-C20)아릴이고, 상기 아릴은 (C6-C20)아릴로 더 치환될 수 있다. 상기 Y는 -O-, -S-, -CR5R6- 또는 -NR7-이고, 여기에서 R5 및 R6은 바람직하게는 각각 독립적으로 (C1-C10)알킬이고, R7은 바람직하게는 (C6-20)아릴이다. 상기 Ar1 및 Ar2은 바람직하게는 각각 독립적으로 수소, 또는 (C6-C20)아릴이고, 상기 아릴은 중수소, 할로겐, (C1-C10)알킬, (C6-C20)아릴, (C6-C20)아릴로 치환되거나 비치환된 (3-20원)헤테로아릴, 트리(C1-C10)알킬실릴, 트리(C6-C20)아릴실릴, 디(C1-C10)알킬(C6-C20)아릴실릴, (C1-C10)알킬디(C6-C20)아릴실릴, 또는 디(C6-C30)아릴아미노로 더 치환될 수 있다. 상기 R1 내지 R4은 바람직하게는 각각 독립적으로 수소, 할로겐, (C6-C20)아릴, -NR11R12 또는 -SiR13R14R15이고, 상기 R3은 인접한 치환체와 함께 단일환 또는 다환의 (C5-C30) 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고, 상기 R11 내지 R17는 바람직하게는 각각 독립적으로 (C6-C20)아릴이다.In Formula 1, L 1 and L 2 are each independently a single bond, a (3- to 20-membered) heteroarylene, or (C6-C20) arylene, wherein the arylene is (C1-C10) It may be further substituted with alkyl or (C6-C20) aryl. X 1 and X 2 are each independently CR ′ or N, wherein R ′ is preferably (C6-C20) aryl, and the aryl may be further substituted with (C6-C20) aryl. Y is —O—, —S—, —CR 5 R 6 — or —NR 7 —, wherein R 5 and R 6 are each independently (C 1 -C 10) alkyl, and R 7 is preferred Preferably (C6-20) aryl. Ar 1 and Ar 2 are each independently hydrogen or (C6-C20) aryl, and the aryl is deuterium, halogen, (C1-C10) alkyl, (C6-C20) aryl, (C6-C20) (3-20 membered) heteroaryl unsubstituted or substituted with aryl, tri (C1-C10) alkylsilyl, tri (C6-C20) arylsilyl, di (C1-C10) alkyl (C6-C20) arylsilyl, ( C1-C10) alkyldi (C6-C20) arylsilyl, or di (C6-C30) arylamino. R 1 to R 4 are each independently hydrogen, halogen, (C6-C20) aryl, -NR 11 R 12 or -SiR 13 R 14 R 15 , wherein R 3 is a monocyclic ring with adjacent substituents or May form a polycyclic (C5-C30) alicyclic or aromatic ring, and the carbon atoms of the formed alicyclic or aromatic ring may be replaced with one or more heteroatoms selected from nitrogen, oxygen, and sulfur, and R 11 to R 17 is preferably each independently (C6-C20) aryl.

구체적으로는, 상기 L1 및 L2 은 각각 독립적으로 단일결합, 페닐렌, 비페닐렌, 터페닐렌, 인데닐렌, 플루오레닐렌, 트리페닐레닐렌, 피렌일렌, 페릴렌일렌, 크라이세닐렌, 나프타세닐렌, 플루오란텐일렌, 티오페닐렌, 피롤릴렌, 피라졸릴렌, 티아졸릴렌, 옥사졸릴렌,옥사디아졸릴렌, 트리아진일렌, 테트라진일렌, 트리아졸릴렌, 퓨라잔일렌, 피리딜렌, 벤조퓨란일렌, 벤조티오펜일렌, 인돌릴렌, 벤조이미다졸릴렌,벤조티아졸릴렌, 벤조이소티아졸릴렌, 벤조이속사졸릴렌, 벤조옥사졸릴렌, 벤조티아디아졸릴렌, 다이벤조퓨란닐렌 또는 다이벤조싸이오페닐렌이고; 상기 Ar1, Ar2 및 R'은 각각 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필,n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실,n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 비페닐, 플루오레닐, 플루오란텐일, 터페닐, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 퀴놀릴, 트리아진일, 벤조퓨란일,다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 퀴녹살리닐 또는 N-카바졸릴이고; R1 내지 R4는 각각 독립적으로 수소, 중수소, 클로로, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸,n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 안트릴, 비페닐, 플루오레닐, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 인데닐, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴,옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, N-카바졸릴, 다이메틸아미노, 다이에틸아미노, 메틸페닐아미노, 다이페닐아미노, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸다이메틸실릴, 다이메틸페닐실릴 또는 트리페닐실릴이고; a 내지 d는 각각 독립적으로 1 또는 2의 정수, 더 바람직하게는 1이고; 상기 Ar1, Ar2, R' 및 R1 내지 R4의 치환기는 각각 중수소, 클로로, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸,n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 9,9-다이메틸플루오레닐, 9,9-다이페닐플루오레닐, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 다이벤조티오펜일, 벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, N-카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 다이메틸아미노, 다이에틸아미노, 메틸페닐아미노, 다이페닐아미노, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸다이메틸실릴, 다이메틸페닐실릴 및 메틸디페닐실릴, 트리페닐실릴, 및 N-페닐카바졸릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있다.Specifically, L 1 and L 2 are each independently a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, peryleneylene, chrysenylene , Naphthacenylene, fluoranthhenylene, thiophenylene, pyrroylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazineylene, tetrazinylene, triazolylene, furazanthylene, Pyridylene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, benzothiadiazolylene, dibenzo Furanylene or dibenzothiophenylene; Ar 1 , Ar 2 and R ′ are each independently hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl , n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl , Fluorenyl, fluoranthenyl, terphenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, quinolyl, tria True, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, quinoxyl Salinyl or N-carbazolyl; R 1 to R 4 are each independently hydrogen, deuterium, chloro, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n Hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, Naphthyl, anthryl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthasenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, Benzoimidazolyl, indenyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazineyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl , Carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl, N-carbazolyl, dimethylamino, diethylamino, memethol Phenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t- butyl) silyl, t- butyl-dimethyl-silyl, dimethyl phenyl silyl or triphenyl silyl gt; a to d are each independently an integer of 1 or 2, more preferably 1; The substituents of Ar 1 , Ar 2 , R ′ and R 1 to R 4 are each deuterium, chloro, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n -Pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluor Propyl, perfluorobutyl, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl , Peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuran 1, dibenzothiophenyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, N-carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, di Methylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl and methyldiphenylsilyl, tri Phenylsilyl, and N-phenylcarbazolyl may be further substituted with one or more substituents selected from the group consisting of:

본 발명에 따른 유기 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있다.The organic luminescent compound according to the present invention can be more specifically exemplified as the following compounds.

Figure pat00002
Figure pat00002

Figure pat00003
Figure pat00003

Figure pat00004
Figure pat00004

Figure pat00005
Figure pat00005

Figure pat00006
Figure pat00006

Figure pat00007
Figure pat00007

Figure pat00008
Figure pat00008

Figure pat00009
Figure pat00009

Figure pat00010
Figure pat00010

Figure pat00011
Figure pat00011

Figure pat00012
Figure pat00012

Figure pat00013
Figure pat00013

Figure pat00014
Figure pat00014

Figure pat00015
Figure pat00015

Figure pat00016
Figure pat00016

Figure pat00017
Figure pat00017

Figure pat00018
Figure pat00018

본 발명에 따른 유기 발광 화합물은 하기 반응식 1 또는 2에 나타난 바와 같이 제조될 수 있다.The organic light emitting compound according to the present invention can be prepared as shown in Scheme 1 or 2.

[반응식 1][Reaction Scheme 1]

Figure pat00019
Figure pat00019

[반응식 2]Scheme 2

Figure pat00020
Figure pat00020

상기 반응식 1 및 2에서, Ar1, Ar2, L1, L2, Y, X1, X2, R1 내지 R4, a, b, c 및 d는 화학식 1에서의 정의와 동일하고, Hal는 할로겐이다.In Schemes 1 and 2, Ar 1 , Ar 2 , L 1 , L 2 , Y, X 1 , X 2 , R 1 to R 4 , a, b, c and d are the same as defined in Formula 1, Hal is halogen.

본 발명은 추가의 양태로 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다. 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극 및 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖고, 상기 유기물층은 상기 화학식 1의 화합물을 하나 이상 포함한다. The present invention provides, in a further aspect, an organic electroluminescent device comprising the compound of formula (1). An organic electroluminescent device according to the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer contains at least one compound of the formula (1).

상기 제1전극과 제2전극 중 하나는 애노드이고 다른 하나는 캐소드일 수 있다. 상기 유기물층은 발광층을 포함하고, 정공 주입층, 정공 수송층, 전자 수송층, 전자 주입층, 계면층(interlayer) 및 정공 저지층에서 선택되는 1층 이상을 더 포함할 수 있다.One of the first electrode and the second electrode may be an anode and the other may be a cathode. The organic material layer may further include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an interlayer and a hole blocking layer.

본 발명의 화학식 1의 화합물은 상기 발광층 및 정공 수송층 중 하나 이상에 포함될 수 있다. 정공 수송층에 사용될 경우, 본 발명의 화학식 1의 화합물은 정공 수송재료로서 포함될 수 있다. 발광층에 사용될 경우, 본 발명의 화학식 1의 화합물은 호스트 재료로서 포함될 수 있고; 바람직하게는 하나 이상의 도펀트를 추가로 더 포함할 수 있으며; 필요한 경우, 본 발명의 화학식 1의 화합물 이외의 다른 화합물을 제2 호스트 재료로 추가로 포함할 수 있다.The compound of Formula 1 of the present invention may be included in at least one of the light emitting layer and the hole transporting layer. When used in the hole transport layer, the compound of formula 1 of the present invention may be included as the hole transport material. When used in the light emitting layer, the compound of Formula 1 of the present invention can be included as a host material; Preferably further comprising one or more dopants; If desired, a compound other than the compound of formula (1) of the present invention may be further included as a second host material.

상기 도펀트로는 하나 이상의 인광 도펀트가 바람직하다. 본 발명의 유기 전계 발광 소자에 적용되는 인광 도펀트 재료는 특별히 제한되지는 않으나, 이리듐(Ir), 오스뮴(Os), 구리(Cu) 및 백금(Pt)으로부터 선택되는 금속 원자의 착체 화합물이 바람직하고, 이리듐(Ir), 오스뮴(Os), 구리(Cu) 및 백금(Pt)으로부터 선택되는 금속 원자의 오르토 메탈화 착체 화합물이 더욱 바람직하며, 오르토 메탈화 이리듐 착체 화합물이 더더욱 바람직하다.As the dopant, at least one phosphorescent dopant is preferable. The phosphorescent dopant material applied to the organic electroluminescent device of the present invention is not particularly limited, but a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) is preferable. More preferred are ortho metallized complex compounds of metal atoms selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and even more preferred are ortho metallized iridium complex compounds.

상기 인광 도펀트는 하기 화학식 2 내지 화학식 4로 표시되는 화합물로 구성된 군으로부터 선택되는 것이 바람직하다.The phosphorescent dopant is preferably selected from the group consisting of the compounds represented by the following Chemical Formulas 2 to 4.

[화학식 2] [화학식 3] [화학식 4][Formula 2] [Formula 3] [Formula 4]

Figure pat00021
Figure pat00022
Figure pat00023
Figure pat00021
Figure pat00022
Figure pat00023

상기 화학식 2 내지 4에서, L은 하기 구조에서 선택되고;In the above formulas 2 to 4, L is selected from the following structures;

Figure pat00024
Figure pat00024

R100은 수소, 치환 또는 비치환된 (C1-C30)알킬, 또는 치환 또는 비치환된 (C3-C30)시클로알킬이며; R101 내지 R109 및 R111 내지 R127은 각각 독립적으로 수소, 중수소, 할로겐, 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C3-C30)시클로알킬, 시아노, 또는 치환 또는 비치환된 (C1-C30)알콕시이고; R201 내지 R211은 각각 독립적으로 수소, 중수소, 할로겐, 또는 할로겐으로 치환 또는 비치환된(C1-C30)알킬, 또는 치환 또는 비치환된 (C3-C30)시클로알킬이며; f 및 g는 각각 독립적으로 1 내지 3의 정수이며, h는 1 또는 2의 정수이며, f 내지 h가 각각 2이상의 정수인 경우 각각의 R100은 서로 동일하거나 상이할 수 있고; n은 1 내지 3의 정수이다. R 100 is hydrogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 3 -C 30) cycloalkyl; R 101 to R 109 and R 111 to R 127 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl unsubstituted or substituted with halogen, substituted or unsubstituted (C3-C30) cycloalkyl, cyano Or substituted or unsubstituted (C1-C30) alkoxy; R 201 to R 211 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl unsubstituted or substituted with halogen, or (C3-C30) cycloalkyl unsubstituted or substituted; f and g are each independently integers of 1 to 3, h is an integer of 1 or 2, and when f to h are each an integer of 2 or more, each of R 100 may be the same or different from each other; n is an integer of 1 to 3;

상기 인광 도펀트 재료의 구체적인 예로는 다음과 같다. Specific examples of the phosphorescent dopant material are as follows.

Figure pat00025
Figure pat00026
Figure pat00027
Figure pat00028
Figure pat00029
Figure pat00030
Figure pat00031
Figure pat00032
Figure pat00033
Figure pat00034
Figure pat00035
Figure pat00036
Figure pat00025
Figure pat00026
Figure pat00027
Figure pat00028
Figure pat00029
Figure pat00030
Figure pat00031
Figure pat00032
Figure pat00033
Figure pat00034
Figure pat00035
Figure pat00036

또한, 본 발명의 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가지며, 상기 유기물층은 발광층을 포함하며, 상기 발광층은 본 발명의 유기전계발광소자용 조성물 및 인광 도펀트 재료를 포함하며, 상기 유기전계발광소자용 조성물은 호스트 재료로 사용된다.Further, the organic electroluminescent device of the present invention includes a first electrode; A second electrode; And at least one organic material layer interposed between the first electrode and the second electrode, wherein the organic material layer includes a light emitting layer, and the light emitting layer comprises the composition for an organic electroluminescence device of the present invention and a phosphorescent dopant material, A composition for an electroluminescent device is used as a host material.

본 발명의 유기 전계 발광 소자는 유기물층에 화학식 1의 화합물을 포함하고, 이와 동시에 아릴아민계 화합물 또는 스티릴아릴아민계 화합물로 이루어진 군으로부터 선택된 하나 이상의 화합물을 포함할 수 있다. The organic electroluminescent device of the present invention may include one or more compounds selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound in addition to the compound of Formula 1 in the organic material layer.

또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄계열금속 및 d-전이원소의 유기금속으로 이루어진 군으로부터 선택되는 하나 이상의 금속 또는 착체화합물을 더 포함할 수도 있고, 나아가 상기 유기물층은 발광층 및 전하생성층을 더 포함할 수 있다.In addition, in the organic electroluminescent device of the present invention, in addition to the compound of Formula 1, an organic compound selected from the group consisting of Group 1, Group 2, Group 4, Group 5 transition metal, Lanthanide series metal and d- And the organic layer may further include a light emitting layer and a charge generating layer.

또한, 본 발명의 상기 유기 전계 발광 소자는 본 발명의 화합물 이외에 당업계에 알려진 청색, 적색 또는 녹색 발광 화합물을 포함하는 발광층 하나 이상을 더 포함함으로써 백색 발광을 할 수 있다. 또한, 필요에 따라, 황색 또는 오렌지색 발광층을 더 포함할 수도 있다.In addition, the organic electroluminescent device of the present invention may emit white light by further including at least one light emitting layer including a blue, red or green light emitting compound known in the art in addition to the compound of the present invention. In addition, if necessary, a yellow or orange light emitting layer may be further included.

본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 일층(이하, 이들을 “표면층”이라고 지칭함) 이상을 배치하는 것이 바람직하다. 구체적으로는, 발광 매체층 측의 양극 표면에 규소 및 알루미늄의 금속의 칼코제나이드(산화물을 포함한다)층을, 또한 발광매체층 측의 음극 표면에 할로겐화 금속층 또는 금속 산화물층을 배치하는 것이 바람직하다. 이것에 의해 구동의 안정화를 얻을 수 있다. 상기 칼코제나이드의 바람직한 예로는 SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON 또는 SiAlON 등이 있고, 할로겐화 금속의 바람직한 예로는 LiF, MgF2, CaF2, 불화 희토류 금속 등이 있으며, 금속 산화물의 바람직한 예로는 Cs2O, Li2O, MgO, SrO, BaO, CaO등이 있다.In the organic electroluminescent device of the present invention, one layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer (hereinafter referred to as " surface layer ") is formed on the inner surface of at least one of the pair of electrodes, Or more. Concretely, it is preferable to dispose a halogenated metal layer or a metal oxide layer on the surface of the anode on the side of the light emitting medium layer and on the surface of the cathode on the side of the light emitting medium layer, with a chalcogenide (including oxide) layer of a metal of silicon and aluminum Do. Thus, stabilization of the drive can be obtained. Preferable examples of the chalcogenide include SiO X (1? X ? 2), AlO x (1? X ? 1.5), SiON or SiAlON. Preferred examples of the halogenated metal include LiF, MgF 2 , CaF 2 , Rare-earth metals, etc. Preferred examples of the metal oxides include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.

또한, 본 발명의 유기 전계 발광 소자에 있어서, 이렇게 제작된 한 쌍의 전극의 적어도 한쪽의 표면에 전자 수송 화합물과 환원성 도펀트의 혼합 영역 또는 정공 수송 화합물과 산화성 도펀트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 수송 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 수송하기 용이해진다. 또한, 정공 수송 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 수송하기 용이해진다. 바람직한 산화성 도펀트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도펀트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도펀트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In the organic electroluminescent device of the present invention, it is also preferable to arrange a mixed region of the electron transport compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant on at least one surface of the pair of electrodes thus fabricated . In this way, the electron transport compound is reduced to an anion, thereby facilitating the injection and transport of electrons from the mixed region to the light emitting medium. In addition, since the hole transport compound is oxidized to become a cation, it is easy to inject and transport holes from the mixed region to the light emitting medium. Preferred oxidative dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. In addition, a white organic electroluminescent device having two or more light emitting layers may be manufactured using a reducing dopant layer as a charge generating layer.

이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 전자 재료용 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, a compound for an organic electronic material according to the present invention, a method for preparing the same, and a light emitting property of a device will be described with reference to a representative compound of the present invention for a detailed understanding of the present invention.

[실시예 1] 화합물 C-52의 제조Example 1 Preparation of Compound C-52

Figure pat00037
Figure pat00037

화합물 1-1의 제조Preparation of Compound 1-1

다이벤조[b,d]티오펜-4-일보론산 (14g, 61mmol), 3-브로모-9H-카바졸 (10g, 41mmol)과 K2CO3 (19.1g, 138mmol)을 톨루엔(200mL)/EtOH(100mL)/ 증류수(100mL)의 혼합용매에 녹인 후, Pd(PPh3)4 (2.3g, 2mmol)을 첨가시켰다. 상기 반응혼합물을 120℃에서 5시간 동안 교반시킨 다음, 실온으로 식히고 EA(800mL)로 추출하여 얻어진 유기층을 증류수(200mL)로 씻어준 다음, 감압 증류하여 유기용매를 제거시켰다. 얻어진 고체는 메탄올로 씻어 필터한 후 건조시켰다. 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 1-1 (10g, 71%)을 얻었다.Toluene (200 mL) with dibenzo [b, d] thiophen-4-ylboronic acid (14 g, 61 mmol), 3-bromo-9H-carbazole (10 g, 41 mmol) and K 2 CO 3 (19.1 g, 138 mmol). After dissolving in a mixed solvent of / EtOH (100 mL) / distilled water (100 mL), Pd (PPh 3 ) 4 (2.3 g, 2 mmol) was added. The reaction mixture was stirred at 120 ° C. for 5 hours, cooled to room temperature and extracted with EA (800 mL). The organic layer was washed with distilled water (200 mL), and then distilled under reduced pressure to remove the organic solvent. The obtained solid was washed with methanol, filtered and dried. Silica gel column chromatography and recrystallization to give the compound 1-1 (10g, 71%).

화합물 1-2의 제조Preparation of Compound 1-2

바이페닐-4-일보론산 (50g, 250mmol), 1,3-다이브로모벤젠 (46mL, 380mmol)과Na2CO3 (66g, 630mmol)을 톨루엔(700mL)/EtOH(320mL)/ 증류수(320mL)의 혼합용매에 녹인 후, Pd(PPh3)2Cl2 (5.6g, 8mmol)을 첨가시켰다. 상기 반응혼합물을 120℃에서 5시간 동안 교반시킨 다음, 실온으로 식히고 EA(1.5L)로 추출하여 얻어진 유기층을 증류수(400mL)로 씻어준 다음, 감압 증류하여 유기용매를 제거시켰다. 얻어진 고체는 메탄올로 씻어 필터한 후 건조시켰다. 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 1-2 (28g, 56%)을 얻었다.Biphenyl-4-ylboronic acid (50 g, 250 mmol), 1,3-dibromobenzene (46 mL, 380 mmol) and Na 2 CO 3 (66 g, 630 mmol) were added to toluene (700 mL) / EtOH (320 mL) / distilled water (320 mL). After dissolving in a mixed solvent of Pd (PPh 3 ) 2 Cl 2 (5.6 g, 8 mmol) was added. The reaction mixture was stirred at 120 ° C. for 5 hours, cooled to room temperature and extracted with EA (1.5 L). The organic layer was washed with distilled water (400 mL), and then distilled under reduced pressure to remove the organic solvent. The obtained solid was washed with methanol, filtered and dried. Silica gel column chromatography and recrystallization to give the compound 1-2 (28g, 56%).

화합물 1-3의 제조Preparation of Compound 1-3

화합물 1-2 (20g, 65mmol)을 THF (350mL)에 녹인 후 -78℃에서 n-BuLi (헥산에서 2.5 M, 39mL, 97mmol)를 첨가시킨 후 한 시간 동안 교반시켰다. 상기 반응물에 B(OMe)3 (11mL, 97mmol)를 천천히 첨가하여 2시간 동안 교반시켰다. 그런 다음, 염화암모늄 수용액 (50mL)로 반응을 종결시킨 후 EA(1L)로 추출하여 얻어진 유기층을 증류수(200mL)로 씻어준다. 상기 얻어진 유기층은 무수 MgSO4를 이용하여 잔여 수분을 제거시킨 뒤 감압 증류하여 용매를 제거시켰다. 얻어진 고체를 재결정방법으로 분리하여 화합물 1-3 (14g, 79%)을 얻었다.Compound 1-2 (20 g, 65 mmol) was dissolved in THF (350 mL) and n-BuLi (2.5 M in hexane, 39 mL, 97 mmol) was added at -78 ° C, followed by stirring for 1 hour. B (OMe) 3 (11 mL, 97 mmol) was slowly added to the reaction and stirred for 2 hours. Then, the reaction was terminated with an aqueous solution of ammonium chloride (50 mL) and extracted with EA (1 L). The organic layer was washed with distilled water (200 mL). The obtained organic layer was removed with residual water using anhydrous MgSO 4 and then distilled under reduced pressure to remove the solvent. The obtained solid was isolated by recrystallization to give compound 1-3 (14 g, 79%).

화합물 1-4의 제조Preparation of Compound 1-4

화합물 1-3 (14g, 51mmol), 2,4-다이클로로피리미딘 (11g, 77mmol)과 Na2CO3 (13.5g, 128mmol)을 톨루엔(130mL)/EtOH(65mL)/증류수(65mL)의 혼합용매에 녹인 후, Pd(PPh3)4 (3g, 2.6mmol)을 첨가시켰다. 상기 반응혼합물을 120℃에서 5시간 동안 교반시킨 다음, 실온으로 식히고 EA(300mL)로 추출하여 얻어진 유기층을 증류수(100mL)로 씻어준 다음, 감압 증류하여 유기용매를 제거시켰다. 얻어진 고체는 메탄올로 씻어 필터한 후 건조시켰다. 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 화합물 1-4 (8g, 46%)을 얻었다.Compound 1-3 (14 g, 51 mmol), 2,4-dichloropyrimidine (11 g, 77 mmol) and Na 2 CO 3 (13.5 g, 128 mmol) were dissolved in toluene (130 mL) / EtOH (65 mL) / distilled water (65 mL). After dissolving in a mixed solvent, Pd (PPh 3 ) 4 (3 g, 2.6 mmol) was added. The reaction mixture was stirred at 120 ° C. for 5 hours, cooled to room temperature and extracted with EA (300 mL). The organic layer was washed with distilled water (100 mL), and then distilled under reduced pressure to remove the organic solvent. The obtained solid was washed with methanol, filtered and dried. Compound 1-4 (8 g, 46%) was obtained by silica gel column chromatography and recrystallization.

화합물 C-52의 제조Preparation of Compound C-52

화합물 1-1 (5g, 14mmol)을 DMF (100mL)에 녹인 후, 교반하면서 NaH (0.9g, 22mmol)을 천천히 첨가시켰다. 30분 교반 후 화합물 1-4 (5.4g, 16mmol)을 DMF (50mL)에 녹여, 상기 반응물에 천천히 넣어준 후 4시간동안 교반시켰다. 상기 반응혼합물을 증류수 (300mL)에 천천히 넣어 30분간 교반시켜 얻어진 고체를 실리카겔 컬럼크로마토그래피와 재결정법으로 분리하여 목적화합물 C-52 (2.4g, 26%)을 얻었다.Compound 1-1 (5 g, 14 mmol) was dissolved in DMF (100 mL), then NaH (0.9 g, 22 mmol) was slowly added while stirring. After stirring for 30 minutes, Compound 1-4 (5.4 g, 16 mmol) was dissolved in DMF (50 mL), and slowly added to the reaction mixture, followed by stirring for 4 hours. The reaction mixture was slowly added to distilled water (300 mL) and stirred for 30 minutes. The solid obtained was separated by silica gel column chromatography and recrystallization to obtain the target compound C-52 (2.4 g, 26%).

[실시예 2] 화합물 C-54의 제조Example 2 Preparation of Compound C-54

Figure pat00038
Figure pat00038

화합물 2-1의 제조Preparation of Compound 2-1

카바졸 (25g, 149.5mmol), 1,3-다이브로모벤젠 (57mL, 448.5mmol), CuI (14.2g, 74.7mmol), 에틸렌다이아민 (5mL, 74.7mmol) 및 K3PO4 (95g, 448.5mmol)를 톨루엔 (450mL)로 녹인 후 120℃에서 24시간 동안 환류교반시켰다. 반응이 완료되면 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 2-1 (42g, 85%)을 얻었다.Carbazole (25 g, 149.5 mmol), 1,3-dibromobenzene (57 mL, 448.5 mmol), CuI (14.2 g, 74.7 mmol), ethylenediamine (5 mL, 74.7 mmol) and K 3 PO 4 (95 g, 448.5 mmol) was dissolved in toluene (450 mL) and then refluxed at 120 ° C. for 24 hours. After the reaction was completed, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and column separation was performed to obtain Compound 2-1 (42 g, 85%).

화합물 2-2의 제조Preparation of Compound 2-2

화합물 2-1 (42g, 130.3mmol)을 THF (500mL)로 녹이고 -78℃로 냉각시켰다. 10분후 n-BuLi (67mL, 169.4mmol) (헥산에서 2.5M)을 천천히 첨가하고 1시간동안 교반시킨 다음, B(OMe)3 (23mL, 208.5mmol)을 천천히 첨가하고 24시간동안 교반시켰다. 반응이 완료되면 1M HCl을 첨가하고 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 MC/헥산으로 재결정하여 화합물 2-2 (25g, 67%)를 얻었다.Compound 2-1 (42 g, 130.3 mmol) was dissolved in THF (500 mL) and cooled to -78 ° C. After 10 minutes n-BuLi (67 mL, 169.4 mmol) (2.5 M in hexane) was added slowly and stirred for 1 h, then B (OMe) 3 (23 mL, 208.5 mmol) was added slowly and stirred for 24 h. After the reaction was completed, 1M HCl was added, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and recrystallized with MC / hexane to give Compound 2-2 (25g, 67%). Got it.

화합물 2-3의 제조Preparation of Compound 2-3

화합물 2-2 (8.9g, 30.9mmol), 2,4-다이클로로피리미딘 (6.9g, 46.6mmol), Pd(PPh3)4 (1.8g, 1.5mmol)과 Na2CO3 (8.2g, 77mmol)를 톨루엔(120mL)/EtOH(40mL)의 혼합용매에 녹인 후 120℃에서 24시간동안 교반시켰다. 교반이 완료된 후 증류수를 천천히 가하여 반응을 종결시킨 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 2-3 (7g, 63.6%)을 얻었다.Compound 2-2 (8.9 g, 30.9 mmol), 2,4-dichloropyrimidine (6.9 g, 46.6 mmol), Pd (PPh 3 ) 4 (1.8 g, 1.5 mmol) and Na 2 CO 3 (8.2 g, 77 mmol) was dissolved in a mixed solvent of toluene (120 mL) / EtOH (40 mL) and stirred at 120 ° C. for 24 hours. After stirring was completed, distilled water was slowly added to terminate the reaction. Then, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and column separation was performed. Compound 2-3 (7g, 63.6%) Got.

화합물 C-54의 제조Preparation of Compound C-54

NaH (674mg, 16.8mmol)을 DMF에 녹여 교반시켰다. 화합물 1-1 (4.7g, 13.5mmol) 을 DMF에 녹인 후, 상기 NaH 용액에 첨가하여 1시간 동안 교반시켰다. 화합물 2-3 (4g, 11.2mmol)을 DMF에 녹인 후 교반시키고, 여기에 상기 화합물 1-1의 혼합용액을 첨가하고 실온에서 24시간 교반시켰다. 반응이 끝나면 생성된 고체를 거른 후, EA로 씻어주고 컬럼으로 분리하여 화합물 C-54 (4g, 44%)를 얻었다. NaH (674 mg, 16.8 mmol) was dissolved in DMF and stirred. Compound 1-1 (4.7 g, 13.5 mmol) was dissolved in DMF, added to the NaH solution, and stirred for 1 hour. Compound 2-3 (4 g, 11.2 mmol) was dissolved in DMF and stirred, and then a mixed solution of compound 1-1 was added thereto, followed by stirring at room temperature for 24 hours. After the reaction was completed, the resulting solids were filtered, washed with EA and separated by column to obtain compound C-54 (4 g, 44%).

[실시예 3] 화합물 C-56의 제조Example 3 Preparation of Compound C-56

Figure pat00039
Figure pat00039

화합물 3-1의 제조Preparation of Compound 3-1

2,4,6-트리클로로피리미딘 (10g, 54.51mmol), 페닐보론산 (16.6g, 136.29mmol), Pd(PPh3)4 (3.15g, 2.72mmol), 2M K2CO3 (50mL), 톨루엔 (100mL) 및 EtOH (30mL)를 혼합하고 환류 교반시켰다. 4시간 후 상온으로 냉각하고 증류수를 넣었다. EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 3-1 (7g, 48%)을 얻었다. 2,4,6-trichloropyrimidine (10 g, 54.51 mmol), phenylboronic acid (16.6 g, 136.29 mmol), Pd (PPh 3 ) 4 (3.15 g, 2.72 mmol), 2M K 2 CO 3 (50 mL) , Toluene (100 mL) and EtOH (30 mL) were mixed and stirred at reflux. After 4 hours, cooled to room temperature and distilled water was added. The organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was performed to remove the solvent, and column separation was performed to obtain compound 3-1 (7g, 48%).

화합물 C-56의 제조Preparation of Compound C-56

NaH (875mg, 21.8mmol)을 DMF에 녹여 교반시켰다. 화합물 1-1 (5.1g, 14.5mmol)을 DMF에 녹인 후, 상기 NaH 용액에 첨가하여 1시간 동안 교반시켰다. 화합물 3-1 (4.7g, 17.5mmol)을 DMF에 녹인 후 교반시키고, 여기에 상기 화합물 1-1의 혼합용액을 첨가하고 실온에서 24시간 교반시켰다. 반응이 끝나면 생성된 고체를 거른 후, EA로 씻어주고 컬럼으로 분리하여 화합물 C-56 (4.5g, 53%)를 얻었다. NaH (875 mg, 21.8 mmol) was dissolved in DMF and stirred. Compound 1-1 (5.1 g, 14.5 mmol) was dissolved in DMF, added to the NaH solution, and stirred for 1 hour. Compound 3-1 (4.7 g, 17.5 mmol) was dissolved in DMF, and then stirred. The mixed solution of compound 1-1 was added thereto, and stirred at room temperature for 24 hours. After the reaction was completed, the produced solid was filtered, washed with EA and separated by column to obtain compound C-56 (4.5g, 53%).

[실시예 4] 화합물 C-63의 제조Example 4 Preparation of Compound C-63

Figure pat00040
Figure pat00040

화합물 4-1의 제조Preparation of Compound 4-1

화합물 1-1 (20g, 57mmol), 13-다이브로모벤젠 (54g, 226mmol), CuI (5g, 28mmol), K3PO4 (36g, 169mmol) 및 톨루엔 (280mL)을 혼합하고 80℃에서 10분간 교반시킨 후, 에틸렌다이아민 (3.5mL, 51mmol)을 첨가시키고 140℃에서 12시간동안 교반시켰다. 반응 종결 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 흰색 고체의 화합물 4-1 (13g, 45%)을 얻었다.Compound 1-1 (20 g, 57 mmol), 13-dibromobenzene (54 g, 226 mmol), CuI (5 g, 28 mmol), K 3 PO 4 (36 g, 169 mmol) and toluene (280 mL) were mixed and 10 min at 80 ° C. After stirring, ethylenediamine (3.5 mL, 51 mmol) was added and stirred at 140 ° C. for 12 h. After completion of the reaction, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was performed to remove the solvent, and column separation was performed to obtain a white solid compound 4-1 (13g, 45%).

화합물 4-2의 제조Preparation of Compound 4-2

화합물 4-1 (13g, 25mmol)을 THF (125mL)로 녹이고 질소 대기 하에서 교반시키면서 -78℃에서 n-BuLi (13mL, 헥산에서 2.25M 용액)을 천천히 첨가시켰다. 동온도에서 1시간 교반하고, 동온도에서 B(OMe)3 (4.8ml, 42mmol)을 천천히 넣은 후 상온으로 온도를 올려 12시간동안 교반시켰다. 반응 종결 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 재결정하여 흰색 고체의 화합물 4-2 (9g, 77%)를 얻었다.Compound 4-1 (13 g, 25 mmol) was dissolved in THF (125 mL) and n-BuLi (13 mL, 2.25 M solution in hexane) was added slowly at −78 ° C. while stirring under nitrogen atmosphere. After stirring for 1 hour at the same temperature, B (OMe) 3 (4.8ml, 42mmol) was slowly added at the same temperature and the temperature was raised to room temperature and stirred for 12 hours. After completion of the reaction, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and recrystallization to obtain a compound 4-2 (9g, 77%) as a white solid.

화합물 4-3의 제조Preparation of Compound 4-3

2,4,6-트리클로로-1,3,5-트리아진 (10.1g, 54.51mmol), 페닐보론산 (16.6g, 136.29mmol), Pd(PPh3)4 (3.15g, 2.72mmol), 2M K2CO3 (50mL), 톨루엔 (100mL)와 EtOH (30mL)를 혼합하고 환류 교반시켰다. 4시간 후 상온으로 냉각시키고 증류수를 가하였다. EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 4-3 (7g, 48%)을 얻었다. 2,4,6-trichloro-1,3,5-triazine (10.1 g, 54.51 mmol), phenylboronic acid (16.6 g, 136.29 mmol), Pd (PPh 3 ) 4 (3.15 g, 2.72 mmol), 2M K 2 CO 3 (50 mL), toluene (100 mL) and EtOH (30 mL) were mixed and stirred at reflux. After 4 hours, the mixture was cooled to room temperature and distilled water was added. The organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , and the solvent was distilled off under reduced pressure to obtain a compound 4-3 (7 g, 48%).

화합물 C-63의 제조Preparation of Compound C-63

화합물 4-3 (4g, 15.1mmol), 화합물 4-2 (8.5g, 18.11mmol), Pd(PPh3)4 (872mg, 0.755mmol), Na2CO3 (4.8g, 45mmol), 톨루엔 (76mL), EtOH (20mL) 및 증류수 (20mL)을 혼합하고 120℃에서 12시간 교반시켰다. 반응 종결 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼분리하여 화합물 C-63 (9g, 90%)을 얻었다.Compound 4-3 (4 g, 15.1 mmol), Compound 4-2 (8.5 g, 18.11 mmol), Pd (PPh 3 ) 4 (872 mg, 0.755 mmol), Na 2 CO 3 (4.8 g, 45 mmol), toluene (76 mL ), EtOH (20 mL) and distilled water (20 mL) were mixed and stirred at 120 ° C for 12 hours. After completion of the reaction, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and column separation was performed to obtain compound C-63 (9g, 90%).

[실시예 5] 화합물 C-81의 제조Example 5 Preparation of Compound C-81

Figure pat00041
Figure pat00041

화합물 5-1의 제조Preparation of Compound 5-1

1,3-다이브로모벤젠 (58g, 246mmol), 페닐보론산 (20g, 164mmol), Pd(PPh3)4 (5.6g, 4.8mmol)과 Na2CO3 (52g, 492mmol)를 톨루엔 (1L)와 EtOH (250mL)의 혼합용매로 녹인 후 90℃에서 3시간동안 교반시켰다. 교반이 완료된 후 증류수를 천천히 가하여 반응을 종결시킨 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 5-1 (26g, 70%)을 얻었다.1,3-dibromobenzene (58g, 246mmol), phenylboronic acid (20g, 164mmol), Pd (PPh 3 ) 4 (5.6g, 4.8mmol) and Na 2 CO 3 (52g, 492mmol) toluene (1L) After melting with a mixed solvent of EtOH (250mL) and stirred at 90 ℃ for 3 hours. After stirring was completed, distilled water was slowly added to terminate the reaction, followed by extracting the organic layer with EA, removing residual moisture using anhydrous MgSO 4 , distilling under reduced pressure to remove the solvent, and then column separating the compound 5-1 (26g, 70%) Got.

화합물 5-2의 제조Preparation of Compound 5-2

화합물 5-1 (26g, 111mmol)을 THF (500mL)로 녹이고 -78℃로 냉각시켰다. 10분후 n-BuLi (66.6ml, 166.5mmol) (헥산에서 2.5M)을 천천히 첨가하고 1시간동안 교반시킨 다음, B(OMe)3 (24.7ml, 222mmol)을 천천히 첨가하고 24시간동안 교반시켰다. 반응이 완료되면 1M HCl을 첨가하고 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 MC/헥산으로 재결정하여 화합물 5-2 (14.3g, 65%)를 얻었다.
Compound 5-1 (26 g, 111 mmol) was dissolved in THF (500 mL) and cooled to -78 ° C. After 10 minutes n-BuLi (66.6 ml, 166.5 mmol) (2.5 M in hexane) was added slowly and stirred for 1 h, then B (OMe) 3 (24.7 ml, 222 mmol) was added slowly and stirred for 24 h. After the reaction was completed, 1M HCl was added, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and recrystallized with MC / hexane to give compound 5-2 (14.3 g, 65%). Got.

화합물 5-3의 제조Preparation of Compound 5-3

화합물 5-2 (14.3g, 72mmol), 1-아이오도-4-브로모벤젠 (30.6g, 108.3mmol), Pd(PPh3)4 (3.3g, 2.9mmol)과 Na2CO3 (22.9g, 216mmol)를 톨루엔(500mL)/EtOH(120mL)의 혼합용매에 녹인 후 120℃에서 24시간동안 교반시켰다. 교반이 완료된 후 증류수를 천천히 가하여 반응을 종결시킨 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 5-3 (20g, 90%)을 얻었다.Compound 5-2 (14.3 g, 72 mmol), 1-iodo-4-bromobenzene (30.6 g, 108.3 mmol), Pd (PPh 3 ) 4 (3.3 g, 2.9 mmol) and Na 2 CO 3 (22.9 g , 216 mmol) was dissolved in a mixed solvent of toluene (500 mL) / EtOH (120 mL) and stirred at 120 ° C. for 24 hours. After stirring was completed, distilled water was slowly added to terminate the reaction. Then, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and column separation was performed. Compound 5-3 (20g, 90%) Got.

화합물 5-4의 제조Preparation of Compound 5-4

화합물 5-3 4(25g, 80.8mmol)을 THF (610mL)로 녹이고 -78℃로 냉각시켰다. 10분후 n-BuLi (48.5ml, 121.2mmol) (헥산에서 2.5M)을 천천히 첨가하고 1시간동안 교반시킨 다음, B(OMe)3 (18ml, 161.7mmol)을 천천히 첨가하고 24시간동안 교반시켰다. 반응이 완료되면 1M HCl을 첨가하고 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 MC/헥산으로 재결정하여 화합물 5-4 (16g, 73%)를 얻었다.Compound 5-3 4 (25 g, 80.8 mmol) was dissolved in THF (610 mL) and cooled to -78 ° C. After 10 minutes n-BuLi (48.5ml, 121.2mmol) (2.5M in hexane) was added slowly and stirred for 1 hour, then B (OMe) 3 (18ml, 161.7mmol) was added slowly and stirred for 24 hours. After the reaction was completed, 1M HCl was added, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , distillation under reduced pressure was carried out to remove the solvent, and recrystallized with MC / hexane to give compound 5-4 (16g, 73%). Got it.

화합물 5-5의 제조Preparation of Compound 5-5

화합물 5-4 (16g, 58.3mmol), 2,4-다이클로로피리미딘 (11.3g, 75.8mmol), Pd(PPh3)4 (3.4g, 2.91mmol)과 Na2CO3 (15.4g, 146mmol)를 톨루엔(300mL)/EtOH(70mL)의 혼합용매에 녹인 후 120℃에서 24시간동안 교반시켰다. 교반이 완료된 후 증류수를 천천히 가하여 반응을 종결시킨 후 EA로 유기층을 추출하고 무수 MgSO4를 이용하여 잔여 수분을 제거한 뒤 감압 증류하여 용매를 제거한 후 컬럼 분리하여 화합물 5-5 (10g, 50%)을 얻었다.Compound 5-4 (16 g, 58.3 mmol), 2,4-dichloropyrimidine (11.3 g, 75.8 mmol), Pd (PPh 3 ) 4 (3.4 g, 2.91 mmol) and Na 2 CO 3 (15.4 g, 146 mmol) ) Was dissolved in a mixed solvent of toluene (300 mL) / EtOH (70 mL) and stirred at 120 ° C. for 24 hours. After stirring was completed, distilled water was slowly added to terminate the reaction. Then, the organic layer was extracted with EA, residual water was removed using anhydrous MgSO 4 , and the solvent was distilled off under reduced pressure to remove the solvent, followed by column separation to obtain compound 5-5 (10 g, 50%). Got.

화합물 C-81의 제조Preparation of Compound C-81

NaH (875mg, 21.8mmol)을 DMF에 녹여 교반시켰다. 화합물 1-1 (5g, 14.5mmol)을 DMF에 녹인 후, 상기 NaH 용액에 첨가하여 1시간 동안 교반시켰다. 화합물 5-5 (6.11g, 17.5mmol)을 DMF에 녹인 후 교반시키고, 여기에 상기 화합물 1-1의 혼합용액을 첨가하고 실온에서 24시간 교반시켰다. 반응이 끝나면 생성된 고체를 거른 후, EA로 씻어주고 컬럼으로 분리하여 화합물 C-81 (5g, 53%)를 얻었다. NaH (875 mg, 21.8 mmol) was dissolved in DMF and stirred. Compound 1-1 (5 g, 14.5 mmol) was dissolved in DMF, added to the NaH solution, and stirred for 1 hour. Compound 5-5 (6.11 g, 17.5 mmol) was dissolved in DMF, followed by stirring. A mixed solution of compound 1-1 was added thereto and stirred at room temperature for 24 hours. After the reaction was completed, the resulting solid was filtered, washed with EA and separated by column to obtain compound C-81 (5 g, 53%).

[실시예 6] 화합물 C-104의 제조Example 6 Preparation of Compound C-104

Figure pat00042
Figure pat00042

화합물 6-1의 제조Preparation of Compound 6-1

다이벤조[b,d]티오펜-4-일 보론산 (30 g, 130 mmol), 3-브로모아이오도벤젠 (34 ml, 260 mmol), Na2CO3 (41 g, 390 mmol) 및 Pd(PPh3)4 (7.5 g, 6.5 mmol)을 톨루엔 300 mL, EtOH 100 mL 및 정제수 100 mL 에 투입 후 100oC에서 3시간 동안 교반 하였다. 반응 종결 후 실온으로 냉각 한 뒤 정치하여 수층을 제거 하였다. 유층은 농축 후 MC로 트리츄레이션한 후 여과하여 화합물 6-1 (33 g, 74 %)을 얻었다. Dibenzo [b, d] thiophen-4-yl boronic acid (30 g, 130 mmol), 3-bromoiodobenzene (34 ml, 260 mmol), Na 2 CO 3 (41 g, 390 mmol) and Pd (PPh 3 ) 4 (7.5 g, 6.5 mmol) was added to 300 mL of toluene, 100 mL of EtOH, and 100 mL of purified water, followed by stirring at 100 ° C. for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and left to stand to remove the aqueous layer. The oil layer was concentrated, triturated with MC, and filtered to obtain compound 6-1 (33 g, 74%).

화합물 6-2의 제조Preparation of Compound 6-2

화합물 6-1(33g, 96mmol)을 THF(650ml)에 녹이고 -78oC에서 2.5 M n-BuLi (헥산에서 2.5 M) (50 ml, 125 mmol)을 첨가한 후 한 시간 동안 교반하였다. B(Oi-Pr)3(35 ml, 154 mmol)을 천천히 첨가하여 2시간 동안 교반하였다. 2M HCl을 첨가하여 퀀칭한 후 증류수와 EA로 추출하였다. MC와 헥산으로 재결정하여 화합물 6-2 (22 g, 76 %)를 얻었다.Compound 6-1 (33 g, 96 mmol) was dissolved in THF (650 ml) and 2.5 M n-BuLi (2.5 M in hexane) (50 ml, 125 mmol) was added at -78 ° C and stirred for an hour. B (Oi-Pr) 3 (35 ml, 154 mmol) was added slowly and stirred for 2 hours. After quenching with the addition of 2M HCl and extracted with distilled water and EA. Recrystallization with MC and hexane gave compound 6-2 (22 g, 76%).

화합물 6-3의 제조Preparation of Compound 6-3

화합물 6-2 (17 g, 55 mmol), 3-브로모카바졸 (13 ml, 55 mmol), K2CO3 (23 g, 163 mmol) 및 Pd(PPh3)4 (3 g, 2.7 mmol)을 톨루엔 300 mL, EtOH 100 mL, 정제수 100 mL 에 투입 후 100oC에서 3시간 동안 교반 하였다. 반응 종결 후 실온으로 냉각 한 뒤 정치하여 수층을 제거 하였다. 유층은 농축 후 MC로 트리츄레이션한 후 여과하여 화합물 6-3 (14 g, 62 %)을 얻었다. Compound 6-2 (17 g, 55 mmol), 3-bromocarbazole (13 ml, 55 mmol), K 2 CO 3 (23 g, 163 mmol) and Pd (PPh 3 ) 4 (3 g, 2.7 mmol) Was added to 300 mL of toluene, 100 mL of EtOH, and 100 mL of purified water, followed by stirring at 100 o C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and left to stand to remove the aqueous layer. The oil layer was concentrated, triturated with MC, and filtered to obtain compound 6-3 (14 g, 62%).

화합물 C-104의 제조Preparation of Compound C-104

화합물 6-3 (5 g, 12 mmol), 2-클로로-4,6-다이페닐-1,3,5-트리아진 (3.2 g, 12 mmol)을 DMF 57 mL에 현탁한 뒤 60% NaH (684 mg, 17.1 mmol)를 상온에서 투입 하였다. 12시간 동안 교반하였다. 정제수(1L) 투입 후 감압여과하였다. 얻어진 고체를 MeOH/EA로 트리츄레이션하고 MC로 녹여 실리카 필터한 후 MC/n-헥산으로 트리츄레이션하여 목적화합물 104 (1.7 g, 22 %) 얻었다.Compound 6-3 (5 g, 12 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.2 g, 12 mmol) was suspended in 57 mL of DMF followed by 60% NaH ( 684 mg, 17.1 mmol) was added at room temperature. Stir for 12 hours. Purified water (1L) and filtered under reduced pressure. The obtained solid was triturated with MeOH / EA, dissolved in MC, silica filtered, and triturated with MC / n-hexane to obtain the target compound 104 (1.7 g, 22%).

상기 실시예 1 내지 6에서 제조된 화합물 및 이로부터 용이하게 제조할 수 있는 다른 화합물에 대한 데이터를 하기 표 1에 나타내었다.Data for the compounds prepared in Examples 1 to 6 and other compounds that can be easily prepared therefrom are shown in Table 1 below.

화합물compound MassMass Yield(%)Yield (%) m.pm.p UV(nm)UV (nm) PL(nm)PL (nm) 4242 688.8688.8 3636 206206 342342 453453 4444 582.7582.7 5454 240240 344344 449449 4848 687687 5555 209209 335335 455455 5252 655.8655.8 2222 236236 336336 450450 5454 669669 4444 251251 344344 463463 5656 580.7580.7 5353 208208 290290 455455 5757 581.7581.7 5858 280280 334334 469469 5959 669.8669.8 4242 254254 344344 428428 6161 657657 3030 246246 356356 395395 6262 657.8657.8 4646 265265 296296 425425 6363 657.2657.2 9090 260260 334334 439439 6868 656.8656.8 7575 220220 344344 456456 8181 656.8656.8 5353 164164 340340 449449 9494 697697 2727 173173 342342 443443 9595 697697 6666 260260 360360 447447 9797 657657 3939 202202 352352 409409 9999 657657 1717 217217 362362 392392 100100 640.7640.7 7474 182182 338338 459459 101101 657657 4141 236236 352352 459459 102102 630.7630.7 7070 241241 390390 429429 103103 671.8671.8 1313 132132 344344 471471 104104 658658 2222 248248 344344 471471 105105 657.8657.8 4343 313313 342342 520520

[실험예 1] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Experimental Example 1 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

본 발명의 발광 재료를 이용하여 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올, 증류수를 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판올에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-바이페닐]-4,4'-다이일)비스(N1-(나프탈렌-1-일)-N4,N4-다이페닐 벤젠-1,4-다이아민) (N1,N1'-([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4- diphenylbenzene-1,4-diamine))을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 N,N'-다이(4-바이페닐)-N,N'-다이(4-바이페닐)-4,4'-다이아미노 바이페닐 (N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl)을 넣고, 셀에 전류를 인가하여 증발시켜 정공주입층 위에 20nm 두께의 정공전달층을 증착하였다. 정공주입층, 정공전달층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 본 발명의 화합물 C-42를 넣고, 또 다른 셀에는 도판트로서 화합물 D-48을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 15중량%으로 도핑함으로서 상기 정공전달층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 이어서 상기 발광층 위에 전자 전달층으로써 한쪽 셀에 2-(4-(9,10-다이(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸 (2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole)을 넣고, 또 다른 셀에는 리튬 퀴놀레이트 (Lithium quinolate)를 각각 넣은 후, 두 물질을 같은 속도로 증발시켜 50중량%으로 도핑 함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로 리튬 퀴놀레이트(Lithium quinolate)를 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device was manufactured using the light emitting material of the present invention. First, a transparent electrode ITO thin film (15? /?) Obtained from a glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water sequentially and stored in isopropanol Respectively. Next, the ITO substrate is mounted on the substrate holder of the vacuum deposition apparatus, and then N 1 , N 1 ′ -([1,1′-biphenyl] -4,4′-diyl) bis ( N 1-(naphthalen- 1 -yl) -N 4 , N 4 -diphenyl benzene-1,4-diamine) (N 1 , N 1 ' -([1,1'-biphenyl] -4,4' -diyl) bis (N 1- (naphthalen-1-yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine)) and evacuated until the vacuum in the chamber reaches 10 -6 torr. A current was applied to the cell and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diamino biphenyl (N, N'- Di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl) was added, and a 20 nm-thick hole transport layer was deposited on the hole injection layer by evaporation by applying a current to the cell. . After the hole injection layer and the hole transport layer were formed, the light emitting layer was deposited thereon as follows. Compound C-42 of the present invention as a host in one cell in the vacuum deposition equipment, Compound D-48 as a dopant in each cell, and then the two materials were evaporated at different rates to be doped at 15% by weight. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. Subsequently, one cell as the electron transporting layer on the light emitting layer, followed by 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1 in one cell as the electron transporting layer on the light emitting layer -Phenyl-1H-benzo [d] imidazole (2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole Lithium quinolate was added to each cell, and the two materials were evaporated at the same rate to be doped at 50% by weight to deposit an electron transport layer of 30 nm. Subsequently, Lithium quinolate was deposited to a thickness of 2 nm as an electron injection layer, and an Al cathode was deposited to a thickness of 150 nm using another vacuum deposition equipment to manufacture an OLED device. Each compound was used by vacuum sublimation purification under 10 -6 torr.

그 결과, 4.4 V의 전압에서 2.17 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다. As a result, a current of 2.17 mA / cm 2 flowed at a voltage of 4.4 V, and green light emission of 1000 cd / m 2 was confirmed.

[실시예 2] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 2 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-44, 도판트에는 화합물 D-1을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.1 V의 전압에서 4.39 mA/cm2의 전류가 흘렀으며, 2030 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound C-44 was used for the host and Compound D-1 for the dopant. As a result, a current of 4.39 mA / cm 2 flowed at a voltage of 3.1 V, and green light emission of 2030 cd / m 2 was confirmed.

[실시예 3] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 3 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-52, 도판트에는 화합물 D-9을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.5 V의 전압에서 2.35 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound C-52 was used for the host and Compound D-9 was used for the dopant. As a result, a current of 2.35 mA / cm 2 flowed at a voltage of 3.5 V, and green light emission of 1000 cd / m 2 was confirmed.

[실시예 4] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 4 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-54, 도판트에는 화합물 D-1을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.8 V의 전압에서 2.21 mA/cm2의 전류가 흘렀으며, 1050 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound C-54 was used for the host and Compound D-1 was used for the dopant. As a result, a current of 2.21 mA / cm 2 flowed at a voltage of 3.8 V, and green light emission of 1050 cd / m 2 was confirmed.

[실시예 5] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 5 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-56, 도판트에는 화합물 D-1을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 2.7 V의 전압에서 3.41 mA/cm2의 전류가 흘렀으며, 1510 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound C-56 was used as a light emitting material and Compound D-1 was used as a dopant. As a result, a current of 3.41 mA / cm 2 flowed at a voltage of 2.7 V, and green light emission of 1510 cd / m 2 was confirmed.

[실시예 6] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 6 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-57, 도판트에는 화합물 D-48을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 4.1 V의 전압에서 5.65 mA/cm2의 전류가 흘렀으며, 2160 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound C-57 was used for the host and Compound D-48 was used for the dopant. As a result, a current of 5.65 mA / cm 2 flowed at a voltage of 4.1 V, and green light emission of 2160 cd / m 2 was confirmed.

[실시예 7] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 7 OLED device fabrication using organic light emitting compound according to the present invention

발광재료로서 호스트에는 화합물 C-59, 도판트에는 화합물 D-48을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.8 V의 전압에서 3.56 mA/cm2의 전류가 흘렀으며, 1470 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound C-59 was used for the host and Compound D-48 was used for the dopant. As a result, a current of 3.56 mA / cm 2 flowed at a voltage of 3.8 V, and green light emission of 1470 cd / m 2 was confirmed.

[실시예 8] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 8 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-61, 도판트에는 화합물 D-9을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 2.7 V의 전압에서 2.69 mA/cm2의 전류가 흘렀으며, 1130 cd/m2의 녹색발광이 확인되었다. An OLED device was manufactured in the same manner as in Example 1, except that Compound C-61 was used for the host and Compound D-9 was used for the dopant. As a result, a current of 2.69 mA / cm 2 flowed at a voltage of 2.7 V, and green light emission of 1130 cd / m 2 was confirmed.

[실시예 9] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 9 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-62, 도판트에는 화합물 D-1을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 2.6 V의 전압에서 2.51 mA/cm2의 전류가 흘렀으며, 890 cd/m2의 녹색발광이 확인되었다.An OLED device was manufactured in the same manner as in Example 1, except that Compound C-62 was used for the host and Compound D-1 was used for the dopant. As a result, a current of 2.51 mA / cm 2 flowed at a voltage of 2.6 V, and green light emission of 890 cd / m 2 was confirmed.

[실시예 10] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 10 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-68, 도판트에는 화합물 D-48을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 2.6 V의 전압에서 3.98 mA/cm2의 전류가 흘렀으며, 1100 cd/m2의 녹색발광이 확인되었다.An OLED device was manufactured in the same manner as in Example 1, except that Compound C-68 was used for the host and Compound D-48 was used for the dopant. As a result, a current of 3.98 mA / cm 2 flowed at a voltage of 2.6 V, and green light emission of 1100 cd / m 2 was confirmed.

[실시예 11] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 11 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-81, 도판트에는 화합물 D-1을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.0 V의 전압에서 2.60 mA/cm2의 전류가 흘렀으며, 1070 cd/m2의 녹색발광이 확인되었다.An OLED device was manufactured in the same manner as in Example 1, except that Compound C-81 was used for the host and Compound D-1 for the dopant. As a result, a current of 2.60 mA / cm 2 flowed at a voltage of 3.0 V, and green light emission of 1070 cd / m 2 was confirmed.

[실시예 12] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작 Example 12 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물C-100, 도판트에는 화합물 D-48을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 4.9 V의 전압에서 9.29 mA/cm2의 전류가 흘렀으며, 4210 cd/m2의 녹색발광이 확인되었다.An OLED device was manufactured in the same manner as in Example 1, except that Compound C-100 was used as a light emitting material and Compound D-48 was used as a dopant. As a result, a current of 9.29 mA / cm 2 flowed at a voltage of 4.9 V, and green light emission of 4210 cd / m 2 was confirmed.

[실시예 13] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작 Example 13 Fabrication of OLED Device Using Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-101, 도판트에는 화합물 D-1을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 4.0 V의 전압에서 9.75 mA/cm2의 전류가 흘렀으며, 3630 cd/m2의 녹색발광이 확인되었다.An OLED device was manufactured in the same manner as in Example 1, except that Compound C-101 was used as a light emitting material and Compound D-1 was used as a dopant. As a result, a current of 9.75 mA / cm 2 flowed at a voltage of 4.0 V, and green light emission of 3630 cd / m 2 was confirmed.

[실시예 14] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작 Example 14 Fabrication of an OLED Device Using an Organic Light Emitting Compound According to the Present Invention

발광재료로서 호스트에는 화합물 C-102, 도판트에는 화합물 D-1을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 3.7 V의 전압에서 4.00 mA/cm2의 전류가 흘렀으며, 1870 cd/m2의 녹색발광이 확인되었다.An OLED device was manufactured in the same manner as in Example 1, except that Compound C-102 was used as a light emitting material and Compound D-1 was used as a dopant. As a result, a current of 4.00 mA / cm 2 flowed at a voltage of 3.7 V, and green light emission of 1870 cd / m 2 was confirmed.

[실시예 15] 본 발명에 따른 유기 발광 화합물을 이용한 OLED 소자 제작Example 15 Fabrication of OLED Devices Using Organic Light-Emitting Compounds According to the Present Invention

발광재료로서 호스트에는 화합물 C-104, 도판트에는 화합물 D-9을 사용한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. 그 결과, 2.6 V의 전압에서 2.42 mA/cm2의 전류가 흘렀으며, 1010 cd/m2의 녹색발광이 확인되었다.An OLED device was manufactured in the same manner as in Example 1, except that Compound C-104 was used for the host and Compound D-9 was used for the dopant. As a result, a current of 2.42 mA / cm 2 flowed at a voltage of 2.6 V, and green light emission of 1010 cd / m 2 was confirmed.

[비교예 1] 종래에 발광재료를 이용한 OLED 소자 제작[Comparative Example 1] Fabrication of OLED device using light emitting material

발광재료로서 호스트에는 4,4‘-N,N'-다이카바졸-바이페닐 (4,4‘-N,N'-dicarbazole-biphenyl), 도판트로는 화합물 Ir(ppy)3 을 사용하고, 정공전달층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 알루미늄(III)비스(2-메틸-8-퀴놀리네이토)4-페닐페놀레이트 (aluminum(III)bis(2-methyl-8-quinolinato) 4-phenylphenolate)을 10nm 두께로 증착한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.4,4'-N, N'-dicarbazole-biphenyl (4,4'-N, N'-dicarbazole-biphenyl) is used as a light emitting material, and the compound Ir (ppy) 3 is used as a dopant, A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer, and aluminum (III) bis (2-methyl-8-quinolinate) 4-phenylphenolate (aluminum (III) bis (2-methyl-8) was used as the hole blocking layer. OLED device was manufactured in the same manner as in Example 1, except that -quinolinato) 4-phenylphenolate) was deposited to a thickness of 10 nm.

그 결과, 4.8 V의 전압에서 2.89 mA/cm2의 전류가 흘렀으며, 1000 cd/m2의 녹색발광이 확인되었다. As a result, a current of 2.89 mA / cm 2 flowed at a voltage of 4.8 V, and green light emission of 1000 cd / m 2 was confirmed.

본 발명에서 개발한 유기 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 전자 재료용 화합물을 발광용 호스트 재료로 사용한 소자는 발광특성이 뛰어날 뿐만 아니라 구동전압을 강하시켜줌으로써 전력효율의 상승을 유도하여 소비전력을 개선시킬 수 있었다.It was confirmed that the luminescence properties of the organic light emitting compounds developed in the present invention showed superior properties compared to the conventional materials. In addition, the device using the organic electronic material compound according to the present invention as a light emitting host material was excellent in the light emitting characteristics, it was possible to improve the power consumption by inducing the increase in power efficiency by lowering the driving voltage.

Claims (6)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure pat00043

상기 화학식 1에서,
L1 및 L2은 각각 독립적으로 단일결합, 치환 또는 비치환된 (3-30원)헤테로아릴렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (C6-C30)시클로알킬렌이고;
X1 및 X2은각각 독립적으로 CR' 또는 N이며;
Y은 -O-, -S-, -CR5R6- 또는 -NR7-이고;
Ar1, Ar2 및 R'는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (3-30원)헤테로아릴이고;
R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (5-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -NR11R12, -SiR13R14R15, -SR16, -OR17, 시아노, 나이트로 또는 하이드록시이고, 인접한 치환체와 함께 단일환 또는 다환의 (C5-C30) 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
R5 내지 R7 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴, 치환 또는 비치환된 (5-7원)헤테로시클로알킬, 또는 치환 또는 비치환된 (C3-C30)시클로알킬이거나, 인접한 치환체와 함께 단일환 또는 다환의 (C5-C30) 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
a 및 c는 각각 독립적으로 1 내지 4의 정수이며, a 또는 c가 2 이상의 정수인 경우 각각의 R1 또는 각각의 R3은 동일하거나 상이할 수 있고;
b 및 d는 각각 독립적으로 1 내지 3의 정수이며, b 또는 d가 2 이상의 정수인 경우 각각의 R2 또는 각각의 R4는 동일하거나 상이할 수 있고;
상기 헤테로아릴렌, 헤테로시클로알킬 및 헤테로아릴은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.
A compound represented by the following formula (1):
[Formula 1]
Figure pat00043

In Chemical Formula 1,
L 1 and L 2 are each independently a single bond, a substituted or unsubstituted (3- to 30-membered) heteroarylene, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted (C6-C30 ) Cycloalkylene;
X 1 and X 2 are each independently CR ′ or N;
Y is -O-, -S-, -CR 5 R 6 -or -NR 7- ;
Ar 1 , Ar 2 and R ′ are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (3 -30 membered) heteroaryl;
R 1 to R 4 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3- to 30-membered) Heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (5- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) ar (C1-C30) alkyl,- NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17, cyano, nitro or hydroxy, and monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring with adjacent substituents And carbon atoms of the alicyclic or aromatic ring formed may be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
R 5 to R 7 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-30 membered) heteroaryl, substituted or unsubstituted (5-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl, or monocyclic or polycyclic (C5) with adjacent substituents -C30) an alicyclic or aromatic ring can be formed, and the carbon atoms of the formed alicyclic or aromatic ring can be replaced with one or more heteroatoms selected from nitrogen, oxygen and sulfur;
a and c are each independently an integer of 1 to 4, and when a or c is an integer of 2 or more, each R 1 or each R 3 may be the same or different;
b and d are each independently integers of 1 to 3, and when b or d is an integer of 2 or more, each R 2 or each R 4 may be the same or different;
The heteroarylene, heterocycloalkyl and heteroaryl include one or more heteroatoms selected from B, N, O, S, P (= 0), Si and P.
제1항에 있어서, 상기 L1, L2, R', Ar1, Ar2, R1 내지 R4, R5 내지 R7 및 R11 내지 R17에서 치환 알킬, 치환 아릴(렌), 치환 헤테로아릴(렌), 치환 시클로알킬(렌), 치환 헤테로시클로알킬 및 치환 아랄킬의 치환체는 각각 독립적으로 중수소, 할로겐, 할로겐으로 치환되거나 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴로 치환되거나 비치환된 (3-30원)헤테로아릴, (C3-C30)시클로알킬, (5-7원)헤테로시클로알킬, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, (C2-C30)알케닐, (C2-C30)알키닐, 시아노, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬, (C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 히드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 특징으로 하는 화합물.The method of claim 1, wherein the substituted alkyl, substituted aryl (ene), substituted at L 1 , L 2 , R ′, Ar 1 , Ar 2 , R 1 to R 4 , R 5 to R 7 and R 11 to R 17 Substituents of heteroaryl (ene), substituted cycloalkyl (ene), substituted heterocycloalkyl and substituted aralkyl are each independently (C 1 -C 30) alkyl unsubstituted or substituted with deuterium, halogen, halogen, (C 6 -C 30) Aryl, (3- to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, (C3-C30) cycloalkyl, (5- to 7-membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, Tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, (C2-C30) alkenyl, (C2- Alkynyl, cyano, N-carbazolyl, di (C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino, di (C6-C30 Aryl boronyl, di (C1-C30) alkyl boronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl, (C1-C30) ) Alkyl (C6-C30) aryl, carboxyl, Compound, characterized in that at least one selected from the group consisting of hydroxy and Trojan. 제1항에 있어서, 상기 L1 및 L2은 각각 독립적으로 단일결합, (3-30원)헤테로아릴렌, 또는 (C6-C30)아릴렌이고; X1 및 X2은 각각 독립적으로 CR' 또는 N이며; Y은 -O-, -S-, -CR5R6- 또는 -NR7-이고; Ar1, Ar2 및R'은 각각 독립적으로 수소, (C1-C30)알킬, (C6-C30)아릴, 또는 (3-30원)헤테로아릴이며; R1 내지 R4은 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, (3-30원)헤테로아릴, -NR11R12 또는 -SiR13R14R15이고, 상기 R3은 인접한 치환체와 함께 단일환 또는 다환의 (C5-C30) 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; R5 내지 R7 및 R11 내지 R17는 각각 독립적으로 수소, 중수소, 할로겐, (C1-C30)알킬, (C6-C30)아릴, 또는 (3-30원)헤테로아릴이고; 상기 L1및 L2의 아릴렌 및 헤테로아릴렌, Ar1, Ar2, R', R1 내지 R4, R5 내지 R7 및 R11 내지 R17의 알킬, 아릴 및 헤테로아릴은 각각 중수소, 할로겐, 할로겐으로 치환되거나 비치환된 (C1-C30)알킬, (C6-C30)아릴, (C6-C30)아릴로 치환되거나 비치환된 (3-30원)헤테로아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, N-카바졸릴, 디(C1-C30)알킬아미노, 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노 및(C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것을 특징으로 하는 화합물.The compound of claim 1, wherein L 1 and L 2 are each independently a single bond, a (3- to 30-membered) heteroarylene, or a (C6-C30) arylene; X 1 and X 2 are each independently CR ′ or N; Y is -O-, -S-, -CR 5 R 6 -or -NR 7- ; Ar 1 , Ar 2 and R ′ are each independently hydrogen, (C 1 -C 30) alkyl, (C 6 -C 30) aryl, or (3-30 membered) heteroaryl; R 1 to R 4 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, (3- to 30-membered) heteroaryl, —NR 11 R 12 or —SiR 13 R 14 R 15 , R 3 may form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring with adjacent substituents, wherein the carbon atoms of the formed alicyclic or aromatic rings are selected from nitrogen, oxygen and sulfur Can be replaced with one or more heteroatoms; R 5 to R 7 and R 11 to R 17 are each independently hydrogen, deuterium, halogen, (C1-C30) alkyl, (C6-C30) aryl, or (3--30 membered) heteroaryl; The arylene and heteroarylene of L 1 and L 2 , Ar 1 , Ar 2 , R ′, alkyl, aryl and heteroaryl of R 1 to R 4 , R 5 to R 7 and R 11 to R 17 are deuterium, respectively. (C1-C30) alkyl unsubstituted or substituted with halogen, halogen, (C6-C30) aryl, (3- to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, tri (C1-C30) Alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, N-carbazolyl, di ( At least one selected from the group consisting of C1-C30) alkylamino, di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino and (C1-C30) alkyl (C6-C30) aryl Compound which can be further substituted by a substituent. 제1항에 있어서, 상기 L1 및 L2 은 각각 독립적으로 단일결합, 페닐렌, 비페닐렌, 터페닐렌, 인데닐렌, 플루오레닐렌, 트리페닐레닐렌, 피렌일렌, 페릴렌일렌, 크라이세닐렌, 나프타세닐렌, 플루오란텐일렌, 티오페닐렌, 피롤릴렌, 피라졸릴렌, 티아졸릴렌, 옥사졸릴렌, 옥사디아졸릴렌, 트리아진일렌, 테트라진일렌, 트리아졸릴렌, 퓨라잔일렌, 피리딜렌, 벤조퓨란일렌, 벤조티오펜일렌, 인돌릴렌, 벤조이미다졸릴렌, 벤조티아졸릴렌, 벤조이소티아졸릴렌, 벤조이속사졸릴렌, 벤조옥사졸릴렌, 벤조티아디아졸릴렌, 다이벤조퓨란닐렌 또는 다이벤조티오페닐렌이고; 상기 Ar1, Ar2 및 R'은 각각 독립적으로 수소, 메틸, 에틸, n-프로필, i-프로필,n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 비페닐, 플루오레닐, 플루오란텐일, 터페닐, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 퀴놀릴, 트리아진일, 벤조퓨란일,다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 퀴녹살리닐 또는 N-카바졸릴이고; R1 내지 R4는 각각 독립적으로 수소, 중수소, 클로로, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 안트릴, 비페닐, 플루오레닐, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 인데닐, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 벤조티오펜일, 다이벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, 티아졸릴,옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, N-카바졸릴, 다이메틸아미노, 다이에틸아미노, 메틸페닐아미노, 다이페닐아미노, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸다이메틸실릴, 다이메틸페닐실릴 또는 트리페닐실릴이고; a 내지 d는 각각 독립적으로 1 또는 2이고; 상기 Ar1, Ar2, R' 및 R1 내지 R4의 치환기는 각각 중수소, 클로로, 플루오르, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, n-헵틸, n-옥틸, 2-에틸헥실, n-노닐, 데실, 도데실, 헥사데실, 트리플루오르메틸, 퍼플루오르에틸, 트리플루오르에틸, 퍼플루오르프로필, 퍼플루오르부틸, 페닐, 나프틸, 비페닐, 9,9-다이메틸플루오레닐, 9,9-다이페닐플루오레닐, 플루오란텐일, 트리페닐렌일, 피렌일, 크라이세닐, 나프타세닐, 페릴렌일, 피리딜, 피롤릴, 퓨란일, 티오펜일, 이미다졸릴, 벤조이미다졸릴, 피라진일, 피리미딘일, 피리다진일, 퀴놀릴, 트리아진일, 벤조퓨란일, 다이벤조퓨란일, 다이벤조티오펜일, 벤조티오펜일, 피라졸릴, 인돌릴, 카바졸릴, N-카바졸릴, 티아졸릴, 옥사졸릴, 벤조티아졸릴, 벤조옥사졸릴, 페난트롤린일, 다이메틸아미노, 다이에틸아미노, 메틸페닐아미노, 다이페닐아미노, 트리메틸실릴, 트리에틸실릴, 트리프로필실릴, 트리(t-부틸)실릴, t-부틸다이메틸실릴, 다이메틸페닐실릴 및 메틸디페닐실릴, 트리페닐실릴, 및 N-페닐카바졸릴로 이루어진 군으로부터 선택되는 하나 이상의 치환기로 더 치환될 수 있는 것을 특징으로 하는 화합물.The method of claim 1, wherein L 1 and L 2 are each independently a single bond, phenylene, biphenylene, terphenylene, indenylene, fluorenylene, triphenylenylene, pyrenylene, peryleneylene, Cry Senylene, naphthacelene, fluoranthhenylene, thiophenylene, pyrroylene, pyrazolylene, thiazolylene, oxazolylene, oxadiazolylene, triazineylene, tetrazinylene, triazolylene, furazanyl Benzene, pyridylene, benzofuranylene, benzothiophenylene, indolylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, benzothiadiazolylene, Dibenzofuranylene or dibenzothiophenylene; Ar 1 , Ar 2 and R ′ are each independently hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl , n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl , Fluorenyl, fluoranthenyl, terphenyl, pyrenyl, chrysenyl, naphthacenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, quinolyl, tria True, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, quinoxyl Salinyl or N-carbazolyl; R 1 to R 4 are each independently hydrogen, deuterium, chloro, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n -Hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, Naphthyl, anthryl, biphenyl, fluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthasenyl, peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, Benzoimidazolyl, indenyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazineyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, pyrazolyl, indolyl , Carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzooxazolyl, phenanthrolinyl, N-carbazolyl, dimethylamino, diethylamino, memethol Phenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t- butyl) silyl, t- butyl-dimethyl-silyl, dimethyl phenyl silyl or triphenyl silyl gt; a to d are each independently 1 or 2; The substituents of Ar 1 , Ar 2 , R ′ and R 1 to R 4 are each deuterium, chloro, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n -Pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluor Propyl, perfluorobutyl, phenyl, naphthyl, biphenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl , Peryleneyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, dibenzofuran 1, dibenzothiophenyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, N-carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolineyl, c Methylamino, diethylamino, methylphenylamino, diphenylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri (t-butyl) silyl, t-butyldimethylsilyl, dimethylphenylsilyl and methyldiphenylsilyl, tri And phenylsilyl, and N-phenylcarbazolyl, which may be further substituted with one or more substituents selected from the group consisting of: 제 1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물로부터 선택되는 것을 특징으로 하는 화합물.
Figure pat00044

Figure pat00045

Figure pat00046

Figure pat00047

Figure pat00048

Figure pat00049

Figure pat00050

Figure pat00051

Figure pat00052

Figure pat00053

Figure pat00054

Figure pat00055

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Figure pat00060
The compound of claim 1, wherein the compound represented by Chemical Formula 1 is selected from the following compounds.
Figure pat00044

Figure pat00045

Figure pat00046

Figure pat00047

Figure pat00048

Figure pat00049

Figure pat00050

Figure pat00051

Figure pat00052

Figure pat00053

Figure pat00054

Figure pat00055

Figure pat00056

Figure pat00057

Figure pat00058

Figure pat00059

Figure pat00060
제1항에 따른 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자. An organic electroluminescent device comprising the compound according to claim 1.
KR1020120078704A 2011-07-21 2012-07-19 Novel organic electroluminescence compounds and organic electroluminescence device using the same KR20130011955A (en)

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