KR20150066202A - Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same - Google Patents

Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same Download PDF

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KR20150066202A
KR20150066202A KR1020130151461A KR20130151461A KR20150066202A KR 20150066202 A KR20150066202 A KR 20150066202A KR 1020130151461 A KR1020130151461 A KR 1020130151461A KR 20130151461 A KR20130151461 A KR 20130151461A KR 20150066202 A KR20150066202 A KR 20150066202A
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substituted
unsubstituted
aryl
alkyl
membered
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KR1020130151461A
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KR101939552B1 (en
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이경주
김치식
안희춘
양수진
문두현
전지송
조영준
이태진
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롬엔드하스전자재료코리아유한회사
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Priority to KR1020130151461A priority Critical patent/KR101939552B1/en
Priority to JP2016532095A priority patent/JP6680675B2/en
Priority to CN201480063491.2A priority patent/CN105764876A/en
Priority to TW103142315A priority patent/TW201529539A/en
Priority to CN202110960033.0A priority patent/CN113582856A/en
Priority to PCT/KR2014/011968 priority patent/WO2015084114A1/en
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Abstract

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By using the organic electroluminescent compound, an organic electroluminescent device having excellent current flow efficiency and light-emitting efficiency can be manufactured.

Description

유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자{Organic Electroluminescent Compound and Organic Electroluminescent Device Comprising the Same}TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent compound and an organic electroluminescent compound including the same,

본 발명은 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same.

표시 소자 중, 전계 발광 소자(electroluminescent device: EL device)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 display devices, an electroluminescent device (EL device) is a self-luminous display device having a wide viewing angle, an excellent contrast, and a high response speed. In 1987, Eastman Kodak Company developed an organic EL device using an aromatic diamine and an aluminum complex having low molecular weight as a light emitting layer forming material [Appl. Phys. Lett. 51, 913, 1987].

유기 전계 발광 소자에서 발광 효율을 결정하는 가장 중요한 요인은 발광 재료이다. 발광 재료로는 현재까지 형광 재료가 널리 사용되고 있으나, 전계 발광의 메커니즘상 형광 발광 재료에 비해 인광 발광 재료가 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 비스(2-(2'-벤조티에닐)-피리디네이토-N,C-3')이리듐(아세틸아세토네이트) [(acac)Ir(btp)2], 트리스(2-페닐피리딘)이리듐 [Ir(ppy)3] 및 비스(4,6-디플루오로페닐피리디네이토-N,C2)피콜리네이토이리듐 (Firpic) 등의 재료가 알려져 있다.The most important factor determining the luminous efficiency in an organic electroluminescent device is a light emitting material. Fluorescent materials have been widely used as luminescent materials to date, but the development of phosphorescent materials has been widely studied in that phosphorescent materials can improve luminous efficiency up to 4 times the theoretical efficiency of phosphorescent materials in terms of the mechanism of electroluminescence . Until now, an iridium (III) complex series has been widely known as a phosphorescent material. Each RGB has bis (2- (2'-benzothienyl) -pyridinate-N, C-3 ') iridium (acetylacetonate ) [(acac) Ir (btp ) 2], tris (2-phenylpyridine) iridium [Ir (ppy) 3] and bis (4,6-difluorophenyl pyridinyl Nei Sat -N, C2) avoid collision Ney And materials such as tolidium (Firpic) are known.

종래 기술에서, 인광용 호스트 재료로는 4,4'-N,N'-디카르바졸-비페닐(CBP)가 가장 널리 알려져 있었다. 최근에는, 일본의 파이오니어 등이 정공 차단층의 재료로 사용되던 바토큐프로인(Bathocuproine, BCP) 및 알루미늄(III)비스(2-메틸-8-퀴놀리네이트)(4-페닐페놀레이트)(Balq)등을 호스트 재료로 이용해 고성능의 유기 전계 발광 소자를 개발한 바 있다.In the prior art, 4,4'-N, N'-dicarbazole-biphenyl (CBP) is the most widely known phosphorescent host material. In recent years, Pioneer et al. Of Japan have been using bathocuproine (BCP) and aluminum (III) bis (2-methyl-8-quinolinate) (4-phenyl phenolate) Balq) as a host material and developed a high-performance organic electroluminescent device.

그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 다음과 같은 단점이 있다: (1) 유리 전이 온도가 낮고 열적 안정성이 낮아서, 진공 하에서 고온 증착 공정시 열화되며, 소자의 수명이 저하된다. (2) 유기 전계 발광 소자에서 전력효율 = [(π/전압) × 전류효율]의 관계에 있으므로 전력 효율은 전압에 반비례하는데, 인광용 호스트 재료를 사용한 유기 전계 발광 소자는 형광 재료를 사용한 유기 전계 발광 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 전계 발광 소자에 사용할 경우, 작동 수명 측면에서도 만족스럽지 못하며, 발광 효율도 여전히 개선이 요구된다.However, existing materials have advantages in terms of luminescence properties, but they have the following disadvantages: (1) They have a low glass transition temperature and a low thermal stability, which deteriorate during a high-temperature deposition process under vacuum, and the lifetime of the device deteriorates. (2) In the organic electroluminescent device, the power efficiency is in the relation of [(? / Voltage) x current efficiency], so that the power efficiency is inversely proportional to the voltage. In the organic electroluminescent device using the phosphorescent host material, The current efficiency (cd / A) is higher than that of the light emitting device, but the driving voltage is also very high, so there is no great advantage in terms of power efficiency (lm / w). (3) In addition, when used in an organic electroluminescent device, it is unsatisfactory in terms of operating life, and luminous efficiency is still required to be improved.

한편, 유기 전계 발광 소자는 이의 효율성 및 안정성을 높이기 위해 정공 주입층, 정공 전달층, 발광층, 전자 전달층 및 전자 주입층 등을 포함하는 다층 구조로 이루어진다. 이 때, 정공 전달층 등에 포함되는 화합물의 선정이 발광층으로의 정공 전달 효율, 발광 효율 및 수명 시간과 같은 소자 특성을 향상시킬 수 있는 수단으로 인식되고 있다.On the other hand, the organic electroluminescent device has a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer in order to improve its efficiency and stability. At this time, the selection of a compound contained in the hole transport layer or the like is recognized as a means for improving device characteristics such as hole transport efficiency, luminescence efficiency, and lifetime of the light emitting layer.

이와 관련해, 유기 전계 발광 소자에서 정공 주입 및 전달 재료로서 구리 프탈로시아닌(CuPc), 4,4'-비스[N-(1-나프틸)-N-페닐아미노]비페닐(NPB), N,N'-디페닐-N,N'-비스(3-메틸페닐)-(1,1'-비페닐)-4,4'-디아민(TPD), 4,4',4"-트리스(3-메틸페닐페닐아미노)트리페닐아민(MTDATA) 등이 사용되어 왔으나, 이러한 물질을 사용한 경우 유기 전계 발광 소자는 양자 효율 및 수명이 저하되는 문제가 있었다. 그 이유는 유기 전계 발광 소자를 높은 전류에서 구동하게 되면, 양극과 정공 주입층 사이에서 열 스트레스(thermal stress)가 발생하고, 이러한 열 스트레스에 의해 소자의 수명이 급격히 저하되기 때문이다. 또한, 정공 주입층에 사용되는 유기물질은 정공의 운동성이 매우 크기 때문에, 정공과 전자의 전하 밸런스(hole-electron charge balance)가 깨지고 이로 인해 양자 효율(cd/A)이 낮아지게 된다.(NPB), N, N (1-naphthyl) -NPhenylamino] biphenyl (NPB) as a hole injection and transport material in organic electroluminescent devices, (TPD), 4,4 ', 4 "-tris (3-methylphenyl) -4,4'-diamine Phenylamino) triphenylamine (MTDATA). However, when such a material is used, there is a problem that the quantum efficiency and lifetime of the organic electroluminescent device are lowered. This is because when the organic electroluminescent device is driven at a high current , Thermal stress is generated between the anode and the hole injection layer, and the lifetime of the device is rapidly lowered due to the thermal stress. The organic material used for the hole injection layer has a very high mobility Therefore, the hole-electron charge balance of holes and electrons is broken and the quantum efficiency (cd / A) is low It becomes.

한국공개특허공보 KR 2012-0029446호, 국제공개특허공보 WO 2013-065589호 및 국제공개특허공보 WO 2007-119800호는 벤조플루오렌계 치환기를 갖는 아민 유도체를 유기 전계 발광 소자용 화합물로 개시하고 있다.Korean Patent Publication Nos. KR 2012-0029446, WO 2013-065589 and WO 2007-119800 disclose an amine derivative having a benzofluorene substituent as an organic electroluminescent compound .

그러나, 상기 문헌에서 벤조플루오렌계 치환기는 모두 벤조[a]플루오렌 또는 벤조[c]플루오렌계의 치환기일 뿐, 벤조[b]플루오렌계 치환기를 갖는 아민 유도체는 구체적으로 개시하지 않고 있다.However, in the above literature, all benzofluorene substituents are benzo [a] fluorene or benzo [c] fluorene substituents, and amine derivatives having a benzo [b] fluorene substituent are not specifically disclosed .

한국공개특허공보 KR 2012-0029446 A (2012. 3. 26 공개)Korean Unexamined Patent Publication No. KR 2012-0029446 A (disclosed on March 26, 2012) 국제공개특허공보 WO 2013-065589 A1 (2013. 5. 10 공개)International Patent Publication WO 2013-065589 A1 (published on Mar. 5, 2013) 국제공개특허공보 WO 2007-119800 A1 (2007. 10. 25 공개)International Patent Publication No. WO 2007-119800 A1 (published on October 25, 2007)

본 발명의 목적은 전류효율 및 발광효율이 우수한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자를 제공하는 것이다.An object of the present invention is to provide an organic electroluminescent compound excellent in current efficiency and luminous efficiency and an organic electroluminescent device including the same.

상기의 기술적 과제를 해결하기 위해 예의 연구한 결과, 본 발명자들은 하기 화학식 1로 표시되는 유기 전계 발광 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 electroluminescent compound represented by the following general formula (1) achieves the above-mentioned object and completed the present invention.

[화학식 1][Chemical Formula 1]

Figure pat00001
Figure pat00001

상기 화학식 1에서,In Formula 1,

Ar1 내지 Ar4은 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며; Ar1과 Ar2는 융합하여 고리를 형성 할 수 있으며;Ar 1 to Ar 4 are each independently a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Ar 1 and Ar 2 may be fused to form a ring;

Ar5 는 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며;Ar 5 is substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;

L1 은 단일 결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이며;L 1 is a single bond, a substituted or unsubstituted (C 6 -C 30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene;

L2 는 치환 또는 비치환된 (C1-C30)알킬렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이며;L 2 is substituted or unsubstituted (C 1 -C 30) alkylene, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene;

R1 및 R2은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -N(R11)(R12), -Si(R13)(R14)(R15), -S(R16), -O(R17), 시아노, 니트로, 또는 하이드록시이거나; 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) N (R 11 ) (R 12 ), -Si (R 13 ) (R 14 ) (R 15 ), -S (R 16 ), -O (R 17 ), cyano, nitro or hydroxy; (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >

R11 내지 R17은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 또는 치환 또는 비치환된 (C3-C30)시클로알킬이거나; 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있으며;R 11 to R 17 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 W) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >

n 및 m은 각각 독립적으로 0 내지 1의 정수이고, 단, n과 m이 동시에 0이 될 수 없고;n and m are each independently an integer of 0 to 1, provided that n and m can not be 0 at the same time;

a는 1 내지 3의 정수이고, a가 2 이상의 정수인 경우 각각의 R1은 동일하거나 상이할 수 있으며; a is an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different;

b는 1 내지 6의 정수이고, b가 2 이상의 정수인 경우 각각의 R2는 동일하거나 상이할 수 있으며;b is an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different;

상기 헤테로아릴(렌)은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고;Wherein said heteroaryl comprises at least one heteroatom selected from B, N, O, S, P (= O), Si and P;

상기 헤테로시클로알킬은 O, S 및 N에서 선택된 하나 이상의 헤테로원자를 포함한다.The heterocycloalkyl includes one or more heteroatoms selected from O, S, and N.

본 발명에 따른 유기 전계 발광 화합물은 전류효율 및 발광효율이 우수한 유기 전계 발광 소자를 제조할 수 있는 장점이 있다.The organic electroluminescent compound according to the present invention is advantageous in manufacturing an organic electroluminescent device having excellent current efficiency and luminous efficiency.

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

본 발명은 상기 화학식 1로 표시되는 유기 전계 발광 화합물, 상기 유기 전계 발광 화합물을 포함하는 유기 전계 발광 재료 및 상기 유기 전계 발광 화합물을 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent compound represented by Formula 1, an organic electroluminescent material including the organic electroluminescent compound, and an organic electroluminescent device including the organic electroluminescent compound.

상기 화학식 1로 표시되는 유기 전계 발광 화합물에 대해 보다 구체적으로 설명하면 다음과 같다.The organic electroluminescent compound represented by Formula 1 will be described in more detail as follows.

본 발명에 기재되어 있는 "알킬"의 구체적인 예로서, 메틸, 에틸, n-프로필, 이소프로필, n-부틸, 이소부틸 및 tert-부틸 등이 있다. 본원에서 "알케닐"의 구체적인 예로서, 비닐, 1-프로페닐, 2-프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 2-메틸부트-2-에닐 등이 있다. 본원에서 "알키닐"의 예로서, 에티닐, 1-프로피닐, 2-프로피닐, 1-부티닐, 2-부티닐, 3-부티닐, 1-메틸펜트-2-이닐 등이 있다. 본원에서 "시클로알킬"의 예로서, 시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실 등이 있다. 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 "아릴(렌)"은 방향족 탄화수소에서 유래된 단일환 또는 융합환계 라디칼을 의미하고, 예로서 페닐, 비페닐, 터페닐, 나프틸, 비나프틸, 페닐나프틸, 나프틸페닐, 플루오레닐, 페닐플루오레닐, 벤조플루오레닐, 디벤조플루오레닐, 페난트레닐, 페닐페난트레닐, 안트라세닐, 인데닐, 트리페닐레닐, 피레닐, 테트라세닐, 페릴레닐, 크라이세닐, 나프타세닐, 플루오란테닐 등이 있다. 본원에서 "(5-30원)헤테로아릴(렌)"은 환 골격 원자수가 5 내지 30개이고, B, N, O, S, P(=O), Si 및 P로 이루어진 군에서 선택된 하나 이상의 헤테로원자를 포함하는 아릴기를 의미한다. 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, 비피리딜, 피라진일, 피리미딜, 피리다진일 등의 단일 환계 헤테로아릴, 벤조푸란일, 벤조티오펜일, 이소벤조푸란일, 디벤조푸란일, 디벤조티오펜일, 나프토푸란일, 나프토티오펜일, 벤조나프토푸란일, 벤조나프토티오펜일, 벤조이미다졸릴, 벤조티아졸릴, 벤조이소티아졸릴, 벤조이속사졸릴, 벤조옥사졸릴, 이소인돌릴, 인돌릴, 인돌리닐, 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.Specific examples of the "alkyl" described in the present invention include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. Specific examples of the "alkenyl" herein include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like. Examples of "alkynyl" herein include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2- Examples of "cycloalkyl" herein include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. The term " (3-7 member) heterocycloalkyl "as used herein refers to a heterocycloalkyl group having 3 to 7 ring skeletal atoms and at least one heteroatom selected from the group consisting of B, N, O, S, P (= O) Preferably one or more heteroatoms selected from O, S and N, and includes, for example, tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like. Means a single ring or fused ring radical derived from an aromatic hydrocarbon and includes, for example, phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, Anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and cricenyl < RTI ID = 0.0 > , Naphthacenyl, fluoranthenyl and the like. As used herein, the term "(5-30) heteroaryl (phenylene)" refers to a heteroaryl group having 5 to 30 ring skeletal atoms and one or more heteroatoms selected from the group consisting of B, N, O, S, P Quot; means an aryl group containing an atom. The number of heteroatoms is preferably 1 to 4, and may be a monocyclic ring system or a fused ring system condensed with at least one benzene ring, and may be partially saturated. In addition, the heteroaryl (phenylene) also includes a heteroaryl group in which at least one heteroaryl or aryl group is linked to a heteroaryl group by a single bond. Examples of such heteroaryls include furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl , Monocyclic heteroaryl such as triazolyl, tetrazolyl, furanzyl, pyridyl, bipyridyl, pyrazinyl, pyrimidyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuran Benzothiazolyl, benzoisothiazolyl, benzoisothiazolyl, benzothiophenyl, benzenaphthothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisothiazolyl, benzoxaphthyl, benzothiazolyl, Wherein the substituent is selected from the group consisting of halogen, cyano, nitro, cyano, nitro, cyano, nitro, cyano, And fused ring heteroaryl such as benzodioxolyl. As used herein, "halogen" includes F, Cl, Br, and I atoms.

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 상기 Ar1 내지 Ar5, L1 내지 L2, R1 및 R2, 및 R11 내지 R17에서 치환 알킬(렌), 치환 아릴(렌), 치환 헤테로아릴(렌), 치환 시클로알킬, 치환 헤테로시클로알킬, 및 치환 아르알킬의 치환체는 각각 독립적으로 중수소, 할로겐, 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, (C6-C30)아릴로 치환 또는 비치환된 (3-30 원)헤테로아릴, (C3-C30)시클로알킬, (3-7 원) 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, 디(C1-C30)알킬아미노, (C1-C30)알킬로 치환 또는 비치환된 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, 디(C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 하이드록시로 이루어진 군으로부터 선택되는 하나 이상인 것을 의미하고, 각각 독립적으로 (C1-C30)알킬, (C6-C21)아릴, (C6-C12)아릴로 치환 또는 비치환된 (5-21원)헤테로아릴, 및 디(C6-C21)아릴아미노로 이루어진 군으로부터 선택되는 하나 이상인 것이 바람직하다.In the term "substituted or unsubstituted" described in the present invention, "substituted" means that a hydrogen atom is replaced with another atom or another functional group (ie, a substituent) in a certain functional group. Wherein Ar 1 to Ar 5, substitution in the L 1 to L 2, R 1 and R 2, and R 11 to R 17 alkyl (arylene) of formula (I), substituted aryl (alkylene), substituted heteroaryl (alkylene), substituted (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkyl, substituted heterocycloalkyl, (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl, tri (C6-C30) (C2-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1- (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) arylamino optionally substituted by halogen, cyano, di (C1- (C6-C30) aryl (C1-C30) arylcarbonyl, di (C1-C30) alkylcarbamoyl, di , Di (C1- C30) alkyl, (C6-C30) aryl, (C6-C30) aryl, (5-21) heteroaryl, and di (C6-C21) arylamino, each of which is unsubstituted or substituted with aryl.

본원 발명의 한 양태에 따르면, 상기 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 4 중 어느 하나로 표시될 수 있고, 바람직하게는, 상기 화학식 1로 표시되는 화합물은 하기 화학식 2 또는 3으로 표시될 수 있다.According to one embodiment of the present invention, the compound represented by Formula 1 may be represented by any one of Chemical Formulas 2 to 4, and preferably, the compound represented by Chemical Formula 1 may be represented by Chemical Formula 2 or 3 have.

[화학식 2](2)

Figure pat00002
Figure pat00002

[화학식 3](3)

Figure pat00003
Figure pat00003

[화학식 4][Chemical Formula 4]

Figure pat00004
Figure pat00004

상기 화학식 2 내지 4에서, Ar1 내지 Ar5, L1 내지 L2, R1 및 R2, a 및 b 은 상기 화학식 1에서 정의된 바와 동일하다.In the general formulas (2) to (4), Ar 1 to Ar 5 , L 1 to L 2 , R 1 and R 2 , a and b are the same as defined in the above formula (1).

상기 화학식 1 내지 4에서, 상기 Ar1 내지 Ar4은 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이고, Ar1과 Ar2는 융합하여 고리를 형성 할 수 있으며; 바람직하게는 치환 또는 비치환 (C6-C21)아릴 또는 치환 또는 비치환 (5-21원)헤테로아릴이고, Ar1과 Ar2는 융합하여 고리를 형성할 수 있으며; 더 바람직하게는, 치환 또는 비치환된 (C6-C21)아릴이고, 여기서 상기 (C6-C21)아릴의 치환체는 (C1-C30)알킬, (C1-C10)알킬로 치환 또는 비치환된 (C6-C21)아릴, 및 (C6-C12)아릴로 치환 또는 비치환된 (5-21원)헤테로아릴로 이루어진 군에서 선택되는 하나 이상일 수 있고, Ar1과 Ar2는 융합하여 고리를 형성할 수 있다. 구체적으로, 상기 Ar1 내지 Ar4은 각각 독립적으로 페닐, 비페닐, 터페닐, 나프틸, 플루오레닐, 또는 벤조플루오레닐일 수 있고, 이들은 각각 독립적으로, (C1-C4)알킬, 페닐, 나프틸, 플루오레닐, 9,9-디메틸-9H-플루오레닐, 피리딜, 이소퀴놀리닐, 퀴나졸리닐, 9-페닐카바졸릴, 디벤조티오펜일 및 디벤조푸란일로 이루어진 군에서 선택되는 하나 이상으로 치환될 수 있고, Ar1과 Ar2는 융합하여 고리를 형성할 수 있다.Wherein Ar 1 to Ar 4 are each independently a substituted or unsubstituted (C 6 -C 30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl, Ar 1 and Ar 2 May be fused to form a ring; Preferably a substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5-21 membered) heteroaryl, Ar 1 and Ar 2 may be fused to form a ring; More preferably, the substituent of the (C6-C21) aryl is substituted or unsubstituted (C6-C21) alkyl substituted or unsubstituted with (C1-C10) -C21) aryl and (C6-C12) and to be at least one selected from the group consisting of a substituted or unsubstituted (5-21 membered) heteroaryl, Ar 1 and Ar 2 are aryl may form a ring fusion have. Specifically, Ar 1 to Ar 4 may each independently be phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, or benzofluorenyl, which are each independently selected from the group consisting of (C 1 -C 4) Naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, pyridyl, isoquinolinyl, quinazolinyl, 9-phenylcarbazolyl, dibenzothiophenyl and dibenzofuranyl And Ar 1 and Ar 2 may be fused to form a ring.

상기 Ar5 는 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며; 바람직하게는 치환 또는 비치환된 (C1-C20)알킬, 치환 또는 비치환된 (C6-C21)아릴, 또는 치환 또는 비치환된 (5-21원)헤테로아릴이다. 더 바람직하게는, Ar5 는 비치환된 (C1-C10)알킬; (C1-C10)알킬, (C6-C21)아릴, (6-21원)헤테로아릴 또는 디(C6-C18)아릴아미노로 치환 또는 비치환된 (C6-C18)아릴; 또는 N, O 및 S로부터 선택된 헤테로원자를 포함하고 (C1-C10)알킬 또는 (C6-C18)아릴로 치환 또는 비치환된 (6-21)원 헤테로아릴일 수 있다. 구체적으로는, Ar5 는 (C1-C4)알킬; (C1-C4)알킬, 페닐, 카바졸릴, 디페닐트리아진일, 페닐벤즈이미다졸릴 또는 디페닐아미노로 치환 또는 비치환된, 페닐, 비페닐, 나프틸, 페난트레닐 또는 플루오레닐; 페닐로 치환 또는 비치환된, 카바졸릴, 벤조카바졸릴, 디벤조티오펜일, 벤조나프토티오펜일, 또는 디벤조푸란일일 수 있다.Ar 5 is substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl; Is preferably a substituted or unsubstituted (C1-C20) alkyl, a substituted or unsubstituted (C6-C21) aryl, or a substituted or unsubstituted (5-21 member) heteroaryl. More preferably, Ar < 5 > is unsubstituted (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with (C1-C10) alkyl, (C6-C21) aryl, (6-21) heteroaryl or di (C6-C18) arylamino; Or (6-21) membered heteroaryl containing a heteroatom selected from N, O and S and substituted or unsubstituted with (C1-C10) alkyl or (C6-C18) aryl. Specifically, Ar < 5 > is (C1-C4) alkyl; (C1-C4) alkyl, phenyl, biphenyl, naphthyl, phenanthrenyl or fluorenyl substituted or unsubstituted with phenyl, carbazolyl, diphenyltriazinyl, phenylbenzimidazolyl or diphenylamino; Substituted or unsubstituted phenyl, carbazolyl, benzocarbazolyl, dibenzothiophenyl, benzonaphthothiophenyl, or dibenzofuranyl.

상기 L1 은 단일 결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이고; 바람직하게는 단일 결합, 치환 또는 비치환된 (C6-C21)아릴렌, 또는 치환 또는 비치환된 (5-21원)헤테로아릴렌이다. 더 바람직하게는 상기 L1 은 단일 결합; (C1-C10)알킬로 치환 또는 비치환된 (C6-C18)아릴렌; 또는 헤테로원자로서 질소 원자를 포함하고 (C1-C10)알킬로 치환 또는 비치환된 (5-18원)헤테로아릴렌이다. 구체적으로는, 상기 L1 은 단일 결합, 페닐 또는 피리미딜이다.Wherein L < 1 > is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene; Preferably a single bond, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5-21 member) heteroarylene. More preferably, L < 1 > is a single bond; (C6-C18) arylene substituted or unsubstituted with (C1-C10) alkyl; Or (5-18 member) heteroarylene which contains a nitrogen atom as a hetero atom and which is substituted or unsubstituted with (C1-C10) alkyl. Specifically, L < 1 > is a single bond, phenyl or pyrimidyl.

상기 L2 는 치환 또는 비치환된 (C1-C30)알킬렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이며; 바람직하게는 치환 또는 비치환된 (C1-C20)알킬렌, 치환 또는 비치환된 (C6-C21)아릴렌, 또는 치환 또는 비치환된 (5-21원)헤테로아릴렌이다. 더 바람직하게는 상기 L2 는 비치환된 (C1-C10)알킬렌; (C1-C10)알킬로 치환 또는 비치환된 (C6-C18)아릴렌; 또는 헤테로원자로서 산소 원자를 포함하고 (C1-C10)알킬로 치환 또는 비치환된 (6-21원)헤테로아릴렌이다. 구체적으로는, 상기 L2 는 (C1-C4)알킬, 페닐, 비페닐, 나프틸, 플루오레닐, 9,9-디메틸-9H-플루오레닐, 또는 디벤조푸란일이다.Said L 2 is substituted or unsubstituted (C 1 -C 30) alkylene, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene; Is preferably a substituted or unsubstituted (C1-C20) alkylene, a substituted or unsubstituted (C6-C21) arylene, or a substituted or unsubstituted (5-21 member) heteroarylene. More preferably, the L 2 is unsubstituted (C1-C10) alkylene; (C6-C18) arylene substituted or unsubstituted with (C1-C10) alkyl; Or a (6-21 membered) heteroarylene which contains an oxygen atom as a hetero atom and which is substituted or unsubstituted with (C1-C10) alkyl. Specifically, L 2 is (C 1 -C 4) alkyl, phenyl, biphenyl, naphthyl, fluorenyl, 9,9-dimethyl-9H-fluorenyl, or dibenzofuranyl.

상기 R1 및 R2은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -N(R11)(R12), -Si(R13)(R14)(R15), -S(R16), -O(R17), 시아노, 니트로, 또는 하이드록시이거나, 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고; 상기 R11 내지 R17은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 또는 치환 또는 비치환된 (C3-C30)시클로알킬이거나; 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있다. 바람직하게는, R1 및 R2은 각각 독립적으로, 수소, 치환 또는 비치환된 (C1-C20)알킬, 치환 또는 비치환된 (C6-C21)아릴, 치환 또는 비치환된 (5-21원)헤테로아릴, 또는 -N(R11)(R12)이고, 상기 R11 및 R12는 각각 독립적으로 치환 또는 비치환된 (C6-C21)아릴이다. 더 바람직하게는, R1 및 R2은 각각 독립적으로 수소; 비치환된 (C6-C18)아릴; 헤테로원자로서 질소 원자를 포함하고 비치환된 (6-18원)헤테로아릴; 또는 -N(R11)(R12)이고; 상기 R11 및 R12는 각각 독립적으로 비치환된 (C6-C18)아릴이다. 구체적으로는, 상기 R1 및 R2은 수소, 페닐, 피리딜, 피리미딜, 디페닐아미노 또는 페닐나프틸아미노이다.Wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) -N (R 11) (R 12 ), -Si (R 13) (R 14) (R 15), -S (R 16), -O (R 17), cyano, nitro, or hydroxy, or, (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI > Wherein R 11 to R 17 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted ) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur . Preferably, R 1 and R 2 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6 -C 21) aryl, substituted or unsubstituted ) heteroaryl, or -N (R 11) (R 12 ) , and wherein R 11 and R 12 are each independently a substituted or unsubstituted (C6-C21) aryl. More preferably, R 1 and R 2 are each independently selected from the group consisting of hydrogen; Unsubstituted (C6-C18) aryl; An unsubstituted (6-18 membered) heteroaryl containing a nitrogen atom as the hetero atom; Or -N (R 11) (R 12 ) a; R 11 and R 12 are each independently unsubstituted (C 6 -C 18) aryl. Specifically, R 1 and R 2 are hydrogen, phenyl, pyridyl, pyrimidyl, diphenylamino or phenylnaphthylamino.

상기 n 및 m은 각각 독립적으로 0 내지 1의 정수이고, 단, n과 m이 동시에 0이 될 수 없다.N and m are each independently an integer of 0 to 1, provided that n and m can not be 0 at the same time.

상기 a는 1 내지 3의 정수이고, a가 2 이상의 정수인 경우 각각의 R1은 동일하거나 상이할 수 있으며; 바람직하게는 a는 1이다.A is an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different; Preferably a is 1.

상기 b는 1 내지 6의 정수이고, b가 2 이상의 정수인 경우 각각의 R2는 동일하거나 상이할 수 있으며; 바람직하게는 b는 1이다.B is an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different; Preferably, b is 1.

본원 발명의 일실시예에 따르면, 상기 화학식 1 내지 4에서, 상기 Ar1 내지 Ar4은 각각 독립적으로 치환 또는 비치환 (C6-C21)아릴 또는 치환 또는 비치환 (5-21원)헤테로아릴이고, Ar1과 Ar2는 융합하여 고리를 형성할 수 있으며; 상기 Ar5는 치환 또는 비치환된 (C1-C20)알킬, 치환 또는 비치환된 (C6-C21)아릴, 또는 치환 또는 비치환된 (5-21원)헤테로아릴이고; 상기 L1은 단일 결합, 치환 또는 비치환된 (C6-C21)아릴렌, 또는 치환 또는 비치환된 (5-21원)헤테로아릴렌이고; 상기 L2는 치환 또는 비치환된 (C1-C20)알킬렌, 치환 또는 비치환된 (C6-C21)아릴렌, 또는 치환 또는 비치환된 (5-21원)헤테로아릴렌이고; 상기 R1 및 R2은 각각 독립적으로 수소, 치환 또는 비치환된 (C1-C20)알킬, 치환 또는 비치환된 (C6-C21)아릴, 치환 또는 비치환된 (5-21원)헤테로아릴, 또는 -N(R11)(R12)이고; 상기 R11 및 R12는 각각 독립적으로 치환 또는 비치환된 (C6-C21)아릴이며; 상기 n 및 m은 각각 독립적으로 0 내지 1의 정수이고, 단, n과 m이 동시에 0이 될 수 없고; 상기 a는 1 내지 3의 정수이고, a가 2 이상의 정수인 경우 각각의 R1은 동일하거나 상이할 수 있으며; 상기 b는 1 내지 6의 정수이고, b가 2 이상의 정수인 경우 각각의 R2는 동일하거나 상이할 수 있으며; 상기 헤테로아릴(렌)은 N, O 및 S 로부터 선택된 하나 이상의 헤테로원자를 포함한다.According to one embodiment of the present invention, in the general formulas (1) to (4), Ar 1 to Ar 4 each independently represent substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5-21 membered heteroaryl , Ar < 1 > and Ar < 2 > may be fused to form a ring; Wherein Ar 5 is substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6 -C 21) aryl, or substituted or unsubstituted (5-21 member) heteroaryl; Wherein L < 1 > is a single bond, substituted or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5-21 membered) heteroarylene; Wherein L 2 is substituted or unsubstituted (C 1 -C 20) alkylene, substituted or unsubstituted (C 6 -C 21) arylene, or substituted or unsubstituted (5-21 member) heteroarylene; Wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6 -C 21) aryl, substituted or unsubstituted (5-21 membered) or -N (R 11) (R 12 ) a; R 11 and R 12 are each independently a substituted or unsubstituted (C 6 -C 21) aryl; And n and m are each independently an integer of 0 to 1, provided that n and m can not be 0 at the same time; A is an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different; B is an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different; The heteroaryl (phenylene) includes at least one heteroatom selected from N, O and S.

본 발명의 다른 일실시예에 따르면, 상기 화학식 1 내지 4에서, 상기 Ar1 내지 Ar4은 치환 또는 비치환된 (C6-C21)아릴이고, 여기서 상기 (C6-C21)아릴의 치환체는 (C1-C30)알킬, (C1-C10)알킬로 치환 또는 비치환된 (C6-C21)아릴, 및 (C6-C12)아릴로 치환 또는 비치환된 (5-21원)헤테로아릴로 이루어진 군에서 선택되는 하나 이상일 수 있고, Ar1과 Ar2는 융합하여 고리를 형성할 수 있고; 상기 Ar5 는 비치환된 (C1-C10)알킬; (C1-C10)알킬, (C6-C21)아릴, (6-21원)헤테로아릴 또는 디(C6-C18)아릴아미노로 치환 또는 비치환된 (C6-C18)아릴; 또는 N, O 및 S로부터 선택된 헤테로원자를 포함하고 (C1-C10)알킬 또는 (C6-C18)아릴로 치환 또는 비치환된 (6-21)원 헤테로아릴일 수 있고; 상기 L1 은 단일 결합; (C1-C10)알킬로 치환 또는 비치환된 (C6-C18)아릴렌; 또는 헤테로원자로서 질소 원자를 포함하고 (C1-C10)알킬로 치환 또는 비치환된 (5-18원)헤테로아릴렌이고; 상기 L2 는 비치환된 (C1-C10)알킬렌; (C1-C10)알킬로 치환 또는 비치환된 (C6-C18)아릴렌; 또는 헤테로원자로서 산소 원자를 포함하고 (C1-C10)알킬로 치환 또는 비치환된 (6-21원)헤테로아릴렌이고; 상기 R1 및 R2은 각각 독립적으로 수소; 비치환된 (C6-C18)아릴; 헤테로원자로서 질소 원자를 포함하고 비치환된 (6-18원)헤테로아릴; 또는 -N(R11)(R12)이고; 상기 R11 및 R12는 각각 독립적으로 비치환된 (C6-C18)아릴이고; 상기 n 및 m은 각각 독립적으로 0 내지 1의 정수이고, 단, n과 m이 동시에 0이 될 수 없고; 상기 a는 1이고; 상기 b는 1이다.According to another embodiment of the present invention, in the above Chemical Formulas 1 to 4, Ar 1 to Ar 4 are substituted or unsubstituted (C6-C21) aryl, wherein the substituent of the (C6-C21) (C6-C21) aryl optionally substituted with (C1-C60) alkyl, (C6-C12) and one or more can be, Ar 1 and Ar 2 may form a fused ring; Ar < 5 > is unsubstituted (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with (C1-C10) alkyl, (C6-C21) aryl, (6-21) heteroaryl or di (C6-C18) arylamino; Or (6-21) membered heteroaryl comprising a heteroatom selected from N, O and S and substituted or unsubstituted with (C1-C10) alkyl or (C6-C18) aryl; L < 1 > is a single bond; (C6-C18) arylene substituted or unsubstituted with (C1-C10) alkyl; Or (5-18 member) heteroarylene which contains a nitrogen atom as a hetero atom and which is substituted or unsubstituted with (C1-C10) alkyl; Wherein L 2 is unsubstituted (C1-C10) alkylene; (C6-C18) arylene substituted or unsubstituted with (C1-C10) alkyl; Or a (6-21 membered) heteroarylene containing an oxygen atom as a hetero atom and being substituted or unsubstituted with (C1-C10) alkyl; R 1 and R 2 are each independently hydrogen; Unsubstituted (C6-C18) aryl; An unsubstituted (6-18 membered) heteroaryl containing a nitrogen atom as the hetero atom; Or -N (R 11) (R 12 ) a; Wherein R 11 and R 12 are each independently unsubstituted (C 6 -C 18) aryl; And n and m are each independently an integer of 0 to 1, provided that n and m can not be 0 at the same time; Wherein a is 1; B is 1.

상기 화학식 1의 유기 전계 발광 화합물은 보다 구체적으로 하기의 화합물로서 예시될 수 있으나, 이들에 한정되는 것은 아니다.The organic electroluminescent compound of Formula 1 may be more specifically exemplified by the following compounds, but is not limited thereto.

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

Figure pat00019
Figure pat00019

Figure pat00020
Figure pat00020

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

Figure pat00025
Figure pat00025

Figure pat00026
Figure pat00026

Figure pat00027
Figure pat00027

본 발명에 따른 유기 전계 발광 화합물은 당업자에게 공지된 합성 방법으로 제조할 수 있으며, 예를 들면 하기 반응식 1 및 2에 나타난 바와 같이 제조할 수 있다.The organic electroluminescent compound according to the present invention can be prepared by a synthesis method known to a person skilled in the art and can be prepared, for example, as shown in the following Schemes 1 and 2.

[반응식 1][Reaction Scheme 1]

Figure pat00028
Figure pat00028

[반응식 2][Reaction Scheme 2]

Figure pat00029
Figure pat00029

또한, 본 발명은 화학식 1의 유기 전계 발광 화합물을 포함하는 유기 전계 발광 재료 및 상기 재료를 포함하는 유기 전계 발광 소자를 제공한다.The present invention also provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the same.

상기 재료는 본 발명의 유기 전계 발광 화합물 단독으로 이루어질 수 있고, 유기 전계 발광 재료에 포함되는 통상의 물질들을 추가로 포함할 수도 있다.The material may be made of the organic electroluminescent compound of the present invention alone, and may further include common materials included in the organic electroluminescent material.

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 유기 전계 발광 화합물을 하나 이상 포함할 수 있다.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, and the organic material layer may include at least one organic electroluminescent compound represented by Formula 1.

상기 제1전극과 제2전극 중 하나는 애노드이고 다른 하나는 캐소드일 수 있다.　상기 유기물층은 발광층을 포함하고, 정공주입층, 정공전달층, 전자전달층, 전자주입층, 계면층(interlayer), 정공차단층 및 전자차단층에서 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, a hole blocking layer, and an electron blocking layer.

본 발명의 유기 전계 발광 화합물은 발광층 및 정공전달층 중 하나 이상에 포함될 수 있다. 정공전달층에 사용될 경우, 본 발명의 유기 전계 발광 화합물은 정공전달 재료로서 포함될 수 있다. 발광층에 사용될 경우, 본 발명의 유기 전계 발광 화합물은 호스트 재료로서 포함될 수 있다.The organic electroluminescent compound 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 transporting layer, the organic electroluminescent compound of the present invention can be included as a hole transporting material. When used in the light emitting layer, the organic electroluminescent compound of the present invention can be included as a host material.

본 발명의 유기 전계 발광 화합물이 정공전달 재료로서 포함될 경우, 발광층은 공지의 발광 재료를 포함하거나, 상기 정공 전달 재료로서 사용된 본 발명의 화합물 이외의 다른 본 발명의 화합물을 발광 재료로서 포함할 수 있다. 상기 공지의 발광 재료는 공지의 호스트 재료일 수 있고, 여기에 하나 이상의 도판트를 더 포함할 수 있다. 상기 공지의 호스트 재료는 공지의 형광 또는 인광 호스트 재료일 수 있다.When the organic electroluminescent compound of the present invention is included as a hole transporting material, the luminescent layer may contain a known luminescent material or may contain a compound of the present invention other than the compound of the present invention used as the hole transporting material as a luminescent material have. The known light emitting material may be a known host material, and may further include one or more dopants. The known host material may be a known fluorescent or phosphorescent host material.

또한, 본 발명의 유기 전계 발광 화합물이 발광층의 호스트 재료(제1 호스트 재료)로서 포함되는 경우, 여기에 하나 이상의 도판트를 더 포함할 수 있다. 또한, 제2 호스트 재료를 더 포함할 수 있고, 이 때, 제1 호스트 재료와 제 2호스트 재료의 중량비는 1:99 내지 99:1 범위이다.Further, when the organic electroluminescent compound of the present invention is included as a host material (first host material) in the light emitting layer, it may further include at least one dopant. It may further comprise a second host material, wherein the weight ratio of the first host material to the second host material is in the range of 1:99 to 99: 1.

상기 공지의 호스트 재료 또는 제2 호스트 재료로서 하기 화학식 5 내지 7로 표시되는 화합물로 구성된 군으로부터 선택되는 것이 발광 효율 면에서 특히 바람직하다.Particularly preferable in view of luminous efficiency is that the known host material or the second host material is selected from the group consisting of the compounds represented by the following formulas (5) to (7).

[화학식 5][Chemical Formula 5]

Figure pat00030
Figure pat00030

[화학식 6][Chemical Formula 6]

Figure pat00031
Figure pat00031

[화학식 7](7)

Figure pat00032
Figure pat00032

상기 화학식 3 내지 5에서,In the above formulas 3 to 5,

Cz는 하기 구조이며,Cz has the following structure,

Figure pat00033
Figure pat00033

R21 내지 R24은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (3-30원)헤테로아릴 또는 R25R26R27Si- 이며, R25 내지 R27는 각각 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 또는 치환 또는 비치환된 (C6-C30)아릴이고; L4은 단일결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이고; M은 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며; Y1 및 Y2는 -O-, -S-, -N(R31)-, -C(R32)(R33)- 이고, Y1과 Y2가 동시에 존재하는 경우는 없으며; R31 내지 R33은 각각 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴이고, R32 및 R33 은 동일하거나 상이할 수 있으며; h 및 i는 각각 독립적으로 1 내지 3의 정수이고, j, k, l 및 r은 각각 독립적으로 0 내지 4의 정수이며, h, i, j, k, l 또는 r이 2 이상의 정수인 경우 각각의 (Cz-L4), 각각의 (Cz), 각각의 R21, 각각의 R22, 각각의 R23 또는 각각의 R24는 동일하거나 상이할 수 있다.R 21 to R 24 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, substituted or unsubstituted Heteroaryl or R 25 R 26 R 27 Si-, R 25 to R 27 are each independently substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl; L 4 is a single bond, substituted or unsubstituted (C6-C30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene; M is a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Y 1 and Y 2 are -O-, -S-, -N (R 31 ) -, -C (R 32 ) (R 33 ) -, and Y 1 and Y 2 are not simultaneously present; R 31 to R 33 each independently represent a substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 W) heteroaryl ring, R 32 And R 33 may be the same or different; each of h and i is independently an integer of 1 to 3, j, k, l and r are each independently an integer of 0 to 4, and when h, i, j, k, l or r is an integer of 2 or more, (Cz-L 4 ), each (Cz), each R 21 , each R 22 , each R 23, or each R 24 may be the same or different.

구체적으로 상기 호스트 재료의 바람직한 예는 다음과 같다.Specifically, preferred examples of the host material are as follows.

Figure pat00034
Figure pat00034

Figure pat00035
Figure pat00035

Figure pat00036
Figure pat00036

Figure pat00037
Figure pat00037

Figure pat00038
Figure pat00038

Figure pat00039
Figure pat00039

Figure pat00040
Figure pat00040

Figure pat00041
Figure pat00041

Figure pat00042
Figure pat00042

Figure pat00043
Figure pat00043

Figure pat00044
Figure pat00044

Figure pat00045
Figure pat00045

Figure pat00046
Figure pat00046

Figure pat00047
Figure pat00047

상기 도판트로는 하나 이상의 인광 도판트가 바람직하다. 본 발명의 유기 전계 발광 소자에 적용되는 인광 도판트 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.The dopant is preferably at least one phosphorescent dopant. The phosphorescent dopant material to be 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) And more preferably an ortho-metallated complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt), and still more preferably an orthometallated iridium complex compound.

상기 인광 도판트는 하기 화학식 8 내지 화학식 10으로 표시되는 화합물로 구성된 군으로부터 선택되는 것이 바람직하다.The phosphorescent dopant is preferably selected from the group consisting of compounds represented by the following formulas (8) to (10).

[화학식 8][Chemical Formula 8]

Figure pat00048
Figure pat00048

[화학식 9][Chemical Formula 9]

Figure pat00049
Figure pat00049

[화학식 10][Chemical formula 10]

Figure pat00050
Figure pat00050

상기 화학식 8 내지 10에서, L은 하기구조에서 선택되고;In Formulas 8 to 10, L is selected from the following structures;

Figure pat00051
Figure pat00051

R100은 수소, 또는 치환 또는 비치환 (C1-C30)알킬이며; R101 내지 R109 및 R111 내지 R123은 각각 독립적으로 수소, 중수소, 할로겐, 할로겐이 치환 또는 비치환 (C1-C30)알킬, 시아노, 또는 치환 또는 비치환 (C1-C30)알콕시이고; R120 내지 R123는 인접 치환기간 융합고리를 이뤄 퀴놀린 형성이 가능하며; R124 내지 R127은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환(C1-C30)알킬, 또는 치환 또는 비치환 (C1-C30)아릴이며; R124 내지 R127가 아릴기인 경우 인접기와 융합고리를 이뤄 플루오렌 형성이 가능하며; R201 내지 R211은 각각 독립적으로 수소, 중수소, 할로겐, 또는 할로겐이 치환 또는 비치환 (C1-C30)알킬이며; o 및 p는 각각 독립적으로 1 내지 3의 정수이며, o 또는 p가 각각 2이상의 정수인 경우 각각의 R100은 서로 동일하거나 상이할 수 있고; d는 1 내지 3의 정수이다.R 100 is hydrogen, or substituted or unsubstituted (C 1 -C 30) alkyl; R 101 to R 109 and R 111 to R 123 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, cyano, or substituted or unsubstituted (C 1 -C 30) alkoxy; R 120 to R 123 are capable of forming a quinoline by forming an adjacent substitution period fused ring; R 124 to R 127 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 1 -C 30) aryl; When R 124 to R 127 are aryl groups, fluorine can be formed by forming a fused ring with the adjacent group; R 201 to R 211 each independently represent hydrogen, deuterium, halogen, or substituted or unsubstituted (C1-C30) alkyl by halogen; o and p are each independently an integer of 1 to 3, and when o or p is an integer of 2 or more, each R 100 may be the same or different from each other; d is an integer of 1 to 3;

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

Figure pat00052
Figure pat00052

Figure pat00053
Figure pat00053

Figure pat00054
Figure pat00054

Figure pat00055
Figure pat00055

Figure pat00056
Figure pat00056

Figure pat00057
Figure pat00057

Figure pat00058
Figure pat00058

Figure pat00059
Figure pat00059

Figure pat00060
Figure pat00060

Figure pat00061
Figure pat00061

Figure pat00062
Figure pat00062

Figure pat00063
Figure pat00063

본 발명은 추가의 양태로 유기 전계 발광 소자 제조용 조성물을 제공한다. 상기 조성물은 호스트 재료 또는 정공전달층 재료로서 본 발명의 화합물을 포함한다.The present invention provides a composition for preparing an organic electroluminescent device in a further aspect. The composition includes a compound of the present invention as a host material or a hole transporting layer material.

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 유기 전계 발광 소자용 조성물을 포함할 수 있다.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 may include the composition for an organic electroluminescent device of the present invention.

본 발명의 유기 전계 발광 소자는 화학식 1의 유기 전계 발광 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 includes the organic electroluminescent compound of Formula 1, and at the same time, may include at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound.

또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 유기 전계 발광 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.Further, in the organic electroluminescent device of the present invention, in addition to the organic electroluminescent compound of Formula 1, an organic electroluminescent compound of the group 1, 2, 4, 5 period transition metal, lanthanide series and d- The organic compound layer may further include at least one metal or complex compound selected from the group consisting of a light emitting layer and a charge generating layer.

또한, 상기 유기물층은 상기 유기 전계 발광 화합물 이외에 청색, 적색 또는 녹색 발광 화합물을 포함하는 유기발광층 하나 이상을 동시에 포함하여 백색 발광을 하는 유기 전계 발광 소자를 형성할 수 있다.In addition, the organic material layer may include at least one organic light emitting layer including a blue, red, or green light emitting compound in addition to the organic electroluminescent compound to form an organic electroluminescent device emitting white light.

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, CaO 등이 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 전달 화합물과 환원성 도판트의 혼합 영역 또는 정공 전달 화합물과 산화성 도판트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 용이해진다. 또한, 정공 전달 화합물은 산화되어 양이온으로 되므로 혼합 영역으로부터 발광 매체에 정공을 주입 및 전달하기 용이해진다. 바람직한 산화성 도판트로서는 각종 루이스산 및 억셉터(acceptor) 화합물을 들 수 있고, 바람직한 환원성 도판트로는 알칼리 금속, 알칼리 금속 화합물, 알칼리 토류 금속, 희토류 금속 및 이들의 혼합물을 들 수 있다. 또한 환원성 도판트층을 전하생성층으로 사용하여 두 개 이상의 발광층을 가진 백색 유기 전계 발광소자를 제작할 수 있다.In addition, in the organic electroluminescent device of the present invention, a mixed region of the electron transfer compound and the reducing dopant or a mixed region of the hole transport compound and the oxidative dopant is disposed on at least one surface of the pair of electrodes thus fabricated desirable. In this way, since the electron transfer compound is reduced to an anion, it becomes easy to inject and transfer electrons from the mixed region to the light emitting medium. Further, since the hole transport compound is oxidized and becomes a cation, it becomes easy to inject and transport holes from the mixed region into the light emitting medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds, and preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Also, a white organic light emitting device having two or more light emitting layers can be manufactured using a reducing dopant layer as a charge generating layer.

본 발명의 유기전계발광소자의 각층의 형성은 진공증착, 스퍼터링, 플라즈마, 이온플레이팅 등의 건식 성막법이나 스핀코팅, 디핑, 플로우 코팅 등의 습식 성막법 중 어느 하나의 방법을 적용할 수 있다.The formation of each layer of the organic electroluminescent device of the present invention can be performed by a dry film formation method such as vacuum deposition, sputtering, plasma or ion plating, or a wet film formation method such as spin coating, dipping or flow coating .

습식 성막법의 경우, 각 층을 형성하는 재료를 에탄올, 클로로포름, 테트라하이드로퓨란, 디옥산 등의 적절한 용매에 용해 또는 분산시켜 박막을 형성하는데, 그 용매는 각 층의 재료가 용해 또는 분산되는 것이라면 어느 것이어도 된다.In the case of the wet film formation method, a thin film is formed by dissolving or dispersing a material forming each layer in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, etc., and the solvent is a solvent in which the material of each layer is dissolved or dispersed Either way.

이하에서, 본 발명의 상세한 이해를 위하여 본 발명의 대표 화합물을 들어 본 발명에 따른 유기 전계 발광 화합물, 이의 제조방법 및 소자의 발광특성을 설명한다.Hereinafter, the organic electroluminescent compound according to the present invention, the method for producing the same, and the luminescent characteristics of the device will be described with reference to the representative compound of the present invention for a detailed understanding of the present invention.

[[ 실시예Example 1] 화합물 C- 1] Compound C- 1 의1 of 제조 Produce

Figure pat00064
Figure pat00064

화합물 1-1의 제조Preparation of Compound 1-1

반응용기에 화합물 6-브로모인단온(50 g, 237 mmol), 프탈알데하이드 (35 g, 261 mmol) 및 에틸알콜600 mL을 넣고, 3시간 동안 환류하였다. 반응용액을 0℃로 냉각하여 석출된 고체를 여과하고 차가운 메틸알콜로 씻어주어 화합물 1-1 (47 g, 64 %)를 얻었다.To the reaction vessel, compound 6-bromine (50 g, 237 mmol), phthalaldehyde (35 g, 261 mmol) and ethyl alcohol (600 mL) were added and refluxed for 3 hours. The reaction solution was cooled to 0 deg. C, and the precipitated solid was filtered and washed with cold methyl alcohol to obtain Compound 1-1 (47 g, 64%).

화합물 1-2의 제조Preparation of Compound 1-2

반응용기에 요오드 (13.5 g, 53.2mmol), 하이포아인산 (25 mL, 243mmol, 50% 수용액), 아세트산 800mL을 넣고 100℃에서 30분간 교반하였다. 여기에 화합물 1-1를 천천히 적가한 후, 밤새교반하였다. 반응 용액을 상온으로 냉각하고 석출된 고체를 여과하고 차가운 메틸알콜로 씻어주어 화합물 1-2 (41.5g, 92%)을 얻었다.Iodine (13.5 g, 53.2 mmol), hypophosphorous acid (25 mL, 243 mmol, 50% aqueous solution) and 800 mL of acetic acid were added to the reaction vessel, followed by stirring at 100 DEG C for 30 minutes. Compound 1-1 was slowly added dropwise thereto, followed by stirring overnight. The reaction solution was cooled to room temperature, and the precipitated solid was filtered and washed with cold methyl alcohol to obtain Compound 1-2 (41.5 g, 92%).

화합물 1-3의 제조Preparation of compounds 1-3

반응용기에 화합물 1-2 (39g, 132mmol), 수산화칼륨 (37g, 660mmol), 요오드화칼륨 (2.2g, 13.3mmol), 벤질트리에틸암모늄 클로라이드(1.5g, 6.6mmol), 증류수 700mL, 디메틸설폭사이드 700mL를 넣고 상온에서 15분간 교반하였다. 여기에 요오드화메틸 (37g, 330mmol)을 넣고 상온에서 밤새 교반하였다. 반응용액은 에틸아세테이트로 희석하고 증류수로 세척하였다. 추출한 유기층을 황산마그네슘으로 건조시킨 후 회전 증발기로 용매를 제거하였다. 이 후 컬럼 크로마토그래피로 정제하여 화합물 1-3 (33 g, 77 %)를 얻었다. To the reaction vessel were added Compound 1-2 (39g, 132mmol), potassium hydroxide (37g, 660mmol), potassium iodide (2.2g, 13.3mmol), benzyltriethylammonium chloride (1.5g, 6.6mmol), distilled water 700mL, dimethylsulfoxide And the mixture was stirred at room temperature for 15 minutes. Methyl iodide (37 g, 330 mmol) was added thereto, followed by stirring overnight at room temperature. The reaction solution was diluted with ethyl acetate and washed with distilled water. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 1-3 (33 g, 77%).

화합물 C-1의 제조Preparation of Compound C-1

반응용기에 화합물 1-3 (10g, 31 mmol), 디비페닐-4-릴아민(9.9g, 31mmol), 팔라듐(II) 아세테이트(0.25g, 1.24mmol), 트리-t-부틸포스핀 (1mL, 3.1mmol 50% 자일렌용액), 소디움 t-부톡사이드 4.5g (46.5 mmol), o-자일렌 150mL를 넣고 1시간 동안 환류하였다. 상온으로 식힌 반응용액은 에틸 아세테이트로 희석하고 물로 여러 번 씻어주었다. 무수 황산마그네슘으로 수분을 제거하였다. 감압증류하고 컬럼 크로마토그래피로 정제하여 화합물 C-1 (9.6 g, 55%)을 얻었다. 화합물 C-1의 물성을 하기 표 1에 나타낸다.
To the reaction vessel was added compound 1-3 (10 g, 31 mmol), dibiphenyl-4-ylamine (9.9 g, 31 mmol), palladium (II) acetate (0.25 g, 1.24 mmol), tri-t-butylphosphine , 3.1 mmol 50% xylene solution), 4.5 g (46.5 mmol) of sodium t-butoxide and 150 mL of o-xylene were added and refluxed for 1 hour. The reaction solution cooled to room temperature was diluted with ethyl acetate and washed several times with water. Water was removed with anhydrous magnesium sulfate. The mixture was distilled under reduced pressure and purified by column chromatography to obtain Compound C-1 (9.6 g, 55%). The physical properties of the compound C-1 are shown in Table 1 below.

[[ 실시예Example 2] 화합물 C- 2] Compound C- 43 의43 제조 Produce

Figure pat00065
Figure pat00065

화합물 2-1의 제조Preparation of Compound 2-1

화합물 2-1은 6-브로모인단온 대신에 5-브로모인단온을 사용한 것을 제외하고는 실시예 1의 1-1부터 1-3의 합성과 동일한 방식으로 진행하여 제조하였다.Compound 2-1 was prepared by proceeding in the same manner as in the synthesis of 1-1 to 1-3 of Example 1, except that a 5-bromo mono-terminated was used in place of the 6-bromo single-point.

화합물 C-43의 제조Preparation of Compound C-43

반응용기에 화합물 2-1 (10g, 31 mmol), 디비페닐-4-릴아민(9.9g, 31mmol), 팔라듐(II) 아세테이트(0.25g, 1.24mmol), 트리-t-부틸포스핀 (1mL, 3.1mmol 50% 자일렌 용액), 소디움 t-부톡사이드 (4.5g, 46.5 mmol), o-자일렌 150mL를 넣고 1시간 동안 환류하였다. 상온으로 식힌 반응용액은 에틸 아세테이트로 희석하고 물로 여러 번 씻어주었다. 무수 황산마그네슘으로 수분을 제거하였다. 감압증류하고 컬럼 크로마토그래피로 정제하여 화합물 C-43 (10.8g, 62%)을 얻었다. 화합물 C-43의 물성을 하기 표 1에 나타낸다.
The reaction vessel was charged with compound 2-1 (10 g, 31 mmol), dibiphenyl-4-ylamine (9.9 g, 31 mmol), palladium (II) acetate (0.25 g, 1.24 mmol), tri-t-butylphosphine , 3.1 mmol 50% xylene solution), sodium t-butoxide (4.5 g, 46.5 mmol) and o-xylene (150 mL) were added and refluxed for 1 hour. The reaction solution cooled to room temperature was diluted with ethyl acetate and washed several times with water. Water was removed with anhydrous magnesium sulfate. The residue was subjected to distillation under reduced pressure and purified by column chromatography to obtain Compound C-43 (10.8 g, 62%). The physical properties of the compound C-43 are shown in Table 1 below.

[[ 실시예Example 3] 화합물 C- 3] Compound C- 71 의71 of 제조 Produce

Figure pat00066
Figure pat00066

화합물 3-1의 제조Preparation of Compound 3-1

반응 용기에 11H-벤조[b]플루오렌-11-온 (41.5 g, 181 mmol), 테트라하이드로푸란 550mL을 넣고 반응 용액을 0℃로 냉각하여 페닐마그네슘브로마이드 (78mL, 235 mmol, 3M 디에틸에테르 용액)을 천천히 적가하였다. 반응용액은 상온에서 1시간 동안 교반하였다. 염화암모늄 수용액으로 반응을 종류하고 에틸 아세테이트로 희석한 후, 물로 씻어주었다. 무수 황산마그네슘으로 수분을 제거하였다. 감압증류하고 컬럼 크로마토그래피로 정제하여 화합물 3-1 (56g, 99%)를 얻었다.11H-benzo [b] fluorene-11-one (41.5 g, 181 mmol) and 550 mL of tetrahydrofuran were placed in a reaction vessel, and the reaction solution was cooled to 0 ° C to obtain phenylmagnesium bromide (78 mL, 235 mmol, Solution) was slowly added dropwise. The reaction solution was stirred at room temperature for 1 hour. The reaction was quenched with aqueous ammonium chloride solution, diluted with ethyl acetate, and washed with water. Water was removed with anhydrous magnesium sulfate. The mixture was distilled under reduced pressure and purified by column chromatography to obtain Compound 3-1 (56 g, 99%).

화합물 3-2의 제조Preparation of Compound 3-2

반응용기에 화합물 3-1 (28 g, 90.3 mmol), 4-브로모트리페닐아민 (88 g, 271 mmol) 및 메틸렌클로라이드(MC) (600 mL)을 넣고, 질소 조건을 만들었다. Eaton`s reagent 3mL를 천천히 적가하였다. 상온에서 2시간 교반 후, 증류수를 넣에 반응을 종료하고, 메틸렌클로라이드로 추출하였다. 추출한 유기층을 황산마그네슘으로 건조시킨 후 회전 증발기로 용매를 제거하였다. 이 후 컬럼 크로마토그래피로 정제하여 화합물 3-2 (38.9 g, 70 %)를 얻었다.Compound 3-1 (28 g, 90.3 mmol), 4-bromotriphenylamine (88 g, 271 mmol) and methylene chloride (MC) (600 mL) were added to the reaction vessel to make nitrogen atmosphere. 3 mL of Eaton`s reagent was slowly added dropwise. After stirring at room temperature for 2 hours, distilled water was added to terminate the reaction, and the mixture was extracted with methylene chloride. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound 3-2 (38.9 g, 70%).

화합물 C-71의 제조Preparation of Compound C-71

반응용기에 화합물 3-2 (10 g, 16.27 mmol), 2-나프틸보론산 (3.4 g, 19.5 mmol), 테트라키스(트리페닐포스핀)팔라듐 (0.7 g, 0.65 mmol), 탄산칼륨 (5.6 g, 40.7 mmol), 톨루엔 60 mL, 에탄올 20 mL을 넣고, 증류수 20 ml를 첨가한 후 120?에서 3시간 교반하였다. 반응이 끝나면 증류수로 세척하고 에틸 아세테이트로 유기층을 추출하였다. 추출한 유기층을 황산마그네슘으로 건조시킨 후 회전 증발기로 용매를 제거하였다. 이 후 컬럼 크로마토그래피로 정제하여 화합물 C-71 (7.6 g, 71 %)를 얻었다. 화합물 C-71의 물성을 하기 표 1에 나타낸다.
To the reaction vessel was added compound 3-2 (10 g, 16.27 mmol), 2-naphthylboronic acid (3.4 g, 19.5 mmol), tetrakis (triphenylphosphine) palladium (0.7 g, 0.65 mmol) g, 40.7 mmol), toluene (60 mL) and ethanol (20 mL) were added, and 20 mL of distilled water was added thereto, followed by stirring at 120? for 3 hours. After the completion of the reaction, the organic layer was washed with distilled water and extracted with ethyl acetate. The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. Thereafter, the residue was purified by column chromatography to obtain Compound C-71 (7.6 g, 71%). The physical properties of the compound C-71 are shown in Table 1 below.

[[ 실시예Example 4] 화합물 C- 4] Compound C- 89 의89's 제조 Produce

Figure pat00067
Figure pat00067

화합물 C-89의 제조Preparation of Compound C-89

반응용기에 화합물 1-3 (5g, 15.4 mmol), 9-페닐-9H,9'H-3,3'-비카바졸 (6.6g, 16.2mmol), 요오드화구리 (1.47 g, 7.73mmol), 디아미노사이클로헥산 (3.7mL, 30.9mmol), 인산칼륨 (9.85g, 46.4 mmol), o-자일렌 100mL를 넣고 2시간 동안 환류하였다. 상온으로 식힌 반응용액은 에틸 아세테이트로 희석하고 물로 여러 번 씻어주었다. 무수 황산마그네슘으로 수분을 제거하였다. 감압증류하고 컬럼 크로마토그래피로 정제하여 4.8g (47%)의 C-89을 얻었다. 화합물 C-89의 물성을 하기 표 1에 나타낸다.To the reaction vessel were added compound 1-3 (5 g, 15.4 mmol), 9-phenyl-9H, 9'H-3,3'-bicarbazole (6.6 g, 16.2 mmol), copper iodide (1.47 g, 7.73 mmol) Diaminocyclohexane (3.7 mL, 30.9 mmol), potassium phosphate (9.85 g, 46.4 mmol) and o-xylene (100 mL) were added and refluxed for 2 hours. The reaction solution cooled to room temperature was diluted with ethyl acetate and washed several times with water. Water was removed with anhydrous magnesium sulfate. Purification by vacuum distillation and purification by column chromatography gave 4.8 g (47%) of C-89. The physical properties of the compound C-89 are shown in Table 1 below.

[[ 실시예Example 5] 화합물 C- 5] Compound C- 125 의125 제조 Produce

Figure pat00068
Figure pat00068

화합물 5-1의 제조Preparation of Compound 5-1

반응용기에 디벤조푸란 (21 g, 127 mmol) 및 테트라하이드로푸란 330 mL 을 넣고, 질소조건을 만든 후 -78℃로 온도를 내렸다. 여기에 n-부틸리튬 50 mL (2.5 M, 115 mmol)을 천천히 적가하였다. 2시간 동안 -78℃에서 교반 후, 330 mL 의 테트라하이드로푸란에 녹아있는 11H-벤조[B]플루오렌-11-온 (26 g, 115 mmol)을 천천히 적가하였다. 적가가 끝나면 반응온도를 상온으로 서서히 올려주고 밤새 교반하였다. 반응이 끝나면, 반응 용액에 염화암모늄 수용액을 넣어 반응을 종료하고, 메틸렌클로라이드(MC)로 추출하였다. 유기층을 황산마그네슘으로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼 크로마토그래피로 정제하여 화합물 5-1 (44 g, 96 %)를 얻었다.The reaction vessel was charged with dibenzofuran (21 g, 127 mmol) and 330 mL of tetrahydrofuran, under nitrogen atmosphere, and then cooled to -78 째 C. 50 mL (2.5 M, 115 mmol) of n-butyllithium was slowly added dropwise thereto. After stirring for 2 hours at -78 [deg.] C, 11H-benzo [B] fluorene-11-one (26 g, 115 mmol) dissolved in 330 mL of tetrahydrofuran was slowly added dropwise. When the dropwise addition was over, the reaction temperature was slowly raised to room temperature and stirred overnight. When the reaction was completed, the reaction solution was quenched with an aqueous solution of ammonium chloride and extracted with methylene chloride (MC). The organic layer was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator. The solvent was then purified by column chromatography to obtain Compound 5-1 (44 g, 96%).

화합물 5-2의 제조Preparation of Compound 5-2

반응용기에 화합물 5-1 (44 g, 110 mmol), 4-브로모트리페닐아민 (89 g, 276 mmol) 및 메틸렌클로라이드(MC) 550 mL을 넣고, 0℃로 온도를 내렸다. 여기에 에톤스촉매 (2.4 ml, 2.2 mmol)을 넣고 상온으로 반응온도를 올려주었다. 추가로 3시간 교반한뒤, 반응 용액에 염화암모늄 수용액을 넣어 반응을 종료하고, 메틸렌클로라이드(MC)로 추출하였다. 유기층을 황산마그네슘으로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼 크로마토그래피로 정제하여 화합물 5-2(55 g, 71 %)를 얻었다.Compound 5-1 (44 g, 110 mmol), 4-bromotriphenylamine (89 g, 276 mmol) and methylene chloride (MC) (550 mL) were added to the reaction vessel and the temperature was lowered to 0 占 폚. Etonose catalyst (2.4 ml, 2.2 mmol) was added thereto, and the reaction temperature was increased to room temperature. After further stirring for 3 hours, an aqueous solution of ammonium chloride was added to the reaction solution to terminate the reaction and extracted with methylene chloride (MC). The organic layer was dried over magnesium sulfate, and the solvent was removed by a rotary evaporator. The solvent was then purified by column chromatography to obtain Compound 5-2 (55 g, 71%).

화합물 compound C-125C-125 의 제조Manufacturing

반응용기에 화합물 5-2 (10 g, 14.1 mmol), 2-나프탈레닐보론산 (2.6 g, 15.6 mmol), 테트라키스(트리페닐포스핀)팔라듐 (0.8 g, 0.71 mmol), 탄산칼륨 (4.7 g, 34.1 mmol), 톨루엔 70 mL, 에탄올 17 mL을 넣고, 증류수 17 ml를 첨가한 후 120?에서 3시간 교반하였다. 반응이 끝나면 증류수로 세척하고 메틸렌클로라이드(MC)로 유기층을 추출하였다. 추출한 유기층을 황산마그네슘으로 건조시킨 후 회전 증발기로 용매를 제거하였다. 이 후 컬럼 크로마토그래피로 정제하여 화합물 C-125 (8.4 g, 80 %)를 얻었다. 화합물 C-125의 물성을 하기 표 1에 나타낸다.(10 g, 14.1 mmol), 2-naphthalenylboronic acid (2.6 g, 15.6 mmol), tetrakis (triphenylphosphine) palladium (0.8 g, 0.71 mmol) and potassium carbonate 4.7 g, 34.1 mmol), 70 mL of toluene and 17 mL of ethanol were added, and 17 mL of distilled water was added, followed by stirring at 120? For 3 hours. After the reaction was completed, the organic layer was washed with distilled water and extracted with methylene chloride (MC). The extracted organic layer was dried with magnesium sulfate and the solvent was removed by a rotary evaporator. The residue was purified by column chromatography to obtain the compound C-125 (8.4 g, 80%). The physical properties of the compound C-125 are shown in Table 1 below.

Figure pat00069
Figure pat00069

[소자 [device 제조예1Production Example 1 ] 본 발명에 따른 유기 ] The organic 전계Field 발광 화합물을 이용한  Using a luminescent compound OLEDOLED 소자 제작 Device fabrication

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(지오마텍 제조)로부터 얻어진 투명전극 ITO 박막(10Ω/□)을, 아세톤, 이소프로판알콜을 순차적으로 사용하여 초음파 세척을 실시한 후, 이소프로판알콜에 넣어 보관한 후 사용하였다. 다음으로 진공 증착 장비의 기판 홀더에 ITO기판을 장착한 후, 진공 증착장비 내의 셀에 N1,N1'-([1,1'-비페닐]-4,4'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-디페닐벤젠 -1,4-디아민) 을 넣고 챔버 내의 진공도가 10E-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에 C-1을 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 하기 [표 2]의 화합물 H- 1를 넣고, 또 다른 셀에는 도판트로서 D-1을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 호스트와 도판트 전체에 대하여 도판트를 15%중량으로 도핑 함으로서 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-디(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸을 넣고, 또다른 셀에는 리튬 퀴놀레이트를 각각 넣은 후, 두 물질을 같은속도로 증발시켜 50%중량으로 도핑 함으로서 30nm의 전자 전달층을 증착하였다. 이어서 전자 주입층으로 리튬 퀴놀레이트를 2nm 두께로 증착한 후, 다른 진공 증착장비를 이용하여 Al 음극을 150nm의 두께로 증착하여 OLED 소자를 제작하였다. 재료 별로 각 화합물은 10E-6 torr 하에서 진공 승화 정제하여 사용하였다.An OLED device having a structure using the light emitting material of the present invention was fabricated. First, a transparent electrode ITO thin film (10? /?) Obtained from a glass for OLED (manufactured by Geomatec) was subjected to ultrasonic cleaning using acetone and isopropanol in succession, and then stored in isopropanol for storage. Next, an ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus, and then N1, N1 '- ([1,1'-biphenyl] -4,4'-diyl) bis N 4, N 4 -diphenylbenzene-1,4-diamine) was introduced into the chamber and evacuated until the degree of vacuum in the chamber reached 10E -6 torr. Then, current was applied to the cell to evaporate it, Lt; RTI ID = 0.0 > 60nm < / RTI > Subsequently, C-1 was placed in another cell in the vacuum vapor deposition apparatus, and a current was applied to the cell to evaporate it, thereby depositing a hole transport layer having a thickness of 20 nm on the hole injection layer. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. The compound H- 1 shown in [Table 2] was added as a host to one cell in the vacuum vapor deposition apparatus, D-1 was added to another cell as a dopant, and the two substances were vaporized at different rates to form a host and a dopant Doped with 15% by weight of the dopant to deposit a 30-nm thick light-emitting layer on the hole-transporting layer. (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) - 1 as an electron transfer layer on one side of the light emitting layer, Phenyl-1H-benzo [d] imidazole, lithium quinolate was added to another cell, and the two materials were evaporated at the same rate and doped with 50% by weight to deposit an electron transport layer of 30 nm. Then, lithium quinolate was deposited to a thickness of 2 nm as an electron injecting layer, and then an Al cathode was deposited to a thickness of 150 nm using another vacuum vapor deposition equipment to fabricate an OLED device. Each compound was purified by vacuum sublimation under 10E- 6 torr.

그 결과, 3.5 mA/cm2의 전류가 흘렀으며, 1500 cd/m2의 녹색발광이 확인되었다.
As a result, a current of 3.5 mA / cm < 2 > flowed and green luminescence of 1500 cd / m < 2 > was confirmed.

[소자 [device 제조예2Production Example 2 ] 본 발명에 따른 유기발광화합물을 이용한 ] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication

정공전달층으로서 C-71을 사용하고 호스트로서 하기 [표 2]의 화합물 H-2와 H-3을 사용 한 것 외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다. C-71 was used as the hole transporting layer, and as a host OLED devices were fabricated in the same manner as in Example 1 except that the compounds H-2 and H-3 shown in Table 2 were used.

그 결과, 14.0 mA/cm2의 전류가 흘렀으며, 700 cd/m2의 청색발광이 확인되었다.
As a result, a current of 14.0 mA / cm < 2 > flowed and blue light emission of 700 cd / m < 2 >

[소자 [device 제조예3Production Example 3 ] 본 발명에 따른 유기 발광화합물을 이용한 ] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication

정공전달층으로서 C-89을 20nm 두께로 증착한 것 이외에는 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.An OLED device was fabricated in the same manner as in Example 1 except that C-89 was deposited to a thickness of 20 nm as a hole transporting layer.

그 결과, 1.9 mA/cm2의 전류가 흘렀으며, 900 cd/m2의 녹색발광이 확인되었다
The result was a current of 1.9 mA / cm 2 flowed, it was confirmed that green light emission of 900 cd / m 2

[소자 [device 제조예4Production Example 4 ] 본 발명에 따른 유기발광화합물을 이용한 ] Using the organic luminescent compound according to the present invention OLEDOLED 소자 제작 Device fabrication

정공전달층으로서 C-125을 사용하고 호스트로서 H-2와 H-3을 사용 한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.OLED devices were fabricated in the same manner as in Example 1 except that C-125 was used as the hole transport layer and H-2 and H-3 were used as the host.

그 결과, 25.0 mA/cm2의 전류가 흘렀으며, 1200 cd/m2의 청색발광이 확인되었다.
As a result, a current of 25.0 mA / cm < 2 > flowed and blue luminescence of 1200 cd / m < 2 > was confirmed.

[[ 비교예1Comparative Example 1 ] 종래의 발광재료를 이용한 ] Using a conventional light emitting material OLEDOLED 소자 제작 Device fabrication

정공전달층으로서 하기 [표 2]의 화합물 T-1을 20nm 두께로 증착한 것 이외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.OLED devices were fabricated in the same manner as in Example 1, except that Compound T-1 shown in [Table 2] below was deposited as a hole transporting layer to a thickness of 20 nm.

그 결과, 26.1 mA/cm2의 전류가 흘렀으며, 9800 cd/m2의 녹색발광이 확인되었다.
As a result, a current of 26.1 mA / cm < 2 > flowed, and green emission of 9800 cd / m < 2 > was confirmed.

[ [ 비교예2Comparative Example 2 ] 종래의 발광재료를 이용한 ] Using a conventional light emitting material OLEDOLED 소자 제작 Device fabrication

정공전달층으로서 T-1을 사용하고 호스트로서 H-2와 H-3을 사용 한 것 외에는 실시예1과 동일한 방법으로 OLED소자를 제작하였다.OLED devices were fabricated in the same manner as in Example 1 except that T-1 was used as the hole transport layer and H-2 and H-3 were used as the host.

그 결과, 141.2 mA/cm2의 전류가 흘렀으며, 2800 cd/m2의 청색발광이 확인되었다.
As a result, a current of 141.2 mA / cm < 2 > flowed and blue light emission of 2800 cd / m < 2 >

본 발명에서 개발한 유기 전자 재료용 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 전자 재료용 화합물을 사용한 소자는 발광특성이 뛰어나고 수명 특성이 좋다.
It was confirmed that the luminescent properties of the compounds for organic electronic materials developed in the present invention exhibit excellent characteristics compared to the conventional materials. Further, the device using the compound for organic electronic material according to the present invention has excellent luminescence characteristics and good lifetime characteristics.

Figure pat00070
Figure pat00070

Claims (7)

하기 화학식 1로 표시되는 유기 전계 발광 화합물.
[화학식 1]
Figure pat00071

상기 화학식 1에서,
Ar1 내지 Ar4은 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며; Ar1과 Ar2는 융합하여 고리를 형성 할 수 있으며;
Ar5 는 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이며;
L1 은 단일 결합, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이며;
L2 는 치환 또는 비치환된 (C1-C30)알킬렌, 치환 또는 비치환된 (C6-C30)아릴렌, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이며;
R1 및 R2은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아르(C1-C30)알킬, -N(R11)(R12), -Si(R13)(R14)(R15), -S(R16), -O(R17), 시아노, 니트로, 또는 하이드록시이거나; 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있고;
R11 내지 R17은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 또는 치환 또는 비치환된 (C3-C30)시클로알킬이거나; 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있으며, 상기 형성된 지환족 또는 방향족 고리의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 치환될 수 있으며;
n 및 m은 각각 독립적으로 0 내지 1의 정수이고, 단, n과 m이 동시에 0이 될 수 없고;
a는 1 내지 3의 정수이고, a가 2 이상의 정수인 경우 각각의 R1은 동일하거나 상이할 수 있으며;
b는 1 내지 6의 정수이고, b가 2 이상의 정수인 경우 각각의 R2는 동일하거나 상이할 수 있으며;
상기 헤테로아릴(렌)은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함하고;
상기 헤테로시클로알킬은 O, S 및 N에서 선택된 하나 이상의 헤테로원자를 포함한다.An organic electroluminescent compound represented by the following formula (1).
[Chemical Formula 1]
Figure pat00071

In Formula 1,
Ar 1 to Ar 4 are each independently a substituted or unsubstituted (C6-C30) aryl, or a substituted or unsubstituted (5-30 membered) heteroaryl; Ar 1 and Ar 2 may be fused to form a ring;
Ar 5 is substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, or substituted or unsubstituted (5-30 membered) heteroaryl;
L 1 is a single bond, a substituted or unsubstituted (C 6 -C 30) arylene, or a substituted or unsubstituted (5-30 membered) heteroarylene;
L 2 is substituted or unsubstituted (C 1 -C 30) alkylene, substituted or unsubstituted (C 6 -C 30) arylene, or substituted or unsubstituted (5-30 membered) heteroarylene;
R 1 and R 2 are each independently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, substituted or unsubstituted (C 6 -C 30) aryl, Substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) N (R 11 ) (R 12 ), -Si (R 13 ) (R 14 ) (R 15 ), -S (R 16 ), -O (R 17 ), cyano, nitro or hydroxy; (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >
R 11 to R 17 each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5-30 W) Heteroaryl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, or substituted or unsubstituted (C3-C30) cycloalkyl; (3-30 membered) monovalent or polycyclic alicyclic or aromatic ring linked to an adjacent substituent, and the carbon atom of the alicyclic or aromatic ring formed may be substituted with one or more heteroatoms selected from nitrogen, oxygen and sulfur ≪ / RTI >
n and m are each independently an integer of 0 to 1, provided that n and m can not be 0 at the same time;
a is an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different;
b is an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different;
Wherein said heteroaryl comprises at least one heteroatom selected from B, N, O, S, P (= O), Si and P;
The heterocycloalkyl includes one or more heteroatoms selected from O, S, and N. 제1항에 있어서, 상기 Ar1 내지 Ar5, L1 내지 L2, R1 및 R2, 및 R11 내지 R17에서 치환 알킬(렌), 치환 아릴(렌), 치환 헤테로아릴(렌), 치환 시클로알킬, 치환 헤테로시클로알킬, 및 치환 아르알킬의 치환체는 각각 독립적으로 중수소, 할로겐, 할로겐으로 치환 또는 비치환된 (C1-C30)알킬, (C1-C30)알콕시, (C6-C30)아릴, (C6-C30)아릴로 치환 또는 비치환된 (3-30 원)헤테로아릴, (C3-C30)시클로알킬, (3-7 원) 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, 디(C1-C30)알킬아미노, (C1-C30)알킬로 치환 또는 비치환된 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, 디(C1-C30)알킬(C6-C30)아릴, 카르복실, 니트로 및 하이드록시로 이루어진 군으로부터 선택되는 하나 이상인, 유기 전계 발광 화합물.According to claim 1, substituted at the Ar 1 to Ar 5, L 1 to L 2, R 1 and R 2, and R 11 to R 17 alkyl (alkylene), substituted aryl (alkylene), substituted heteroaryl (alkylene) (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) alkoxy substituted by halogen, halogen, (C3-C30) cycloalkyl, (3-7 membered) heterocycloalkyl, tri (C1-C30) alkylsilyl substituted with (C6-C30) aryl, (C2-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1- (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) aryl optionally substituted with (Cl-C30) alkynyl, cyano, di (C6-C30) aryl (C1-C30) arylcarbonyl, di (C6-C30) arylboronyl, di ) Alkyl, di (C1- C30) alkyl (C6-C30) aryl, carboxyl, nitro, and hydroxy. 제1항에 있어서, 상기 화학식 1로 표시되는 화합물이 하기 화학식 2 내지 4 중 어느 하나로 표시되는 것인, 유기 전계 발광 화합물:
[화학식 2]
Figure pat00072

[화학식 3]
Figure pat00073

[화학식 4]
Figure pat00074

상기 화학식 2 내지 4에서, Ar1 내지 Ar5, L1 및 L2, R1 및 R2, a 및 b 은 제1항에서 정의된 바와 동일하다.The organic electroluminescent compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (2) to (4)
(2)
Figure pat00072

(3)
Figure pat00073

[Chemical Formula 4]
Figure pat00074

In the above Chemical Formulas 2 to 4, Ar 1 to Ar 5 , L 1 and L 2 , R 1 and R 2 , a and b are the same as defined in claim 1. 제1항에 있어서, 상기 Ar1 내지 Ar4은 각각 독립적으로 치환 또는 비치환 (C6-C21)아릴 또는 치환 또는 비치환 (5-21원)헤테로아릴이고, Ar1과 Ar2는 융합하여 고리를 형성할 수 있으며;
상기 Ar5 는 치환 또는 비치환된 (C1-C20)알킬, 치환 또는 비치환된 (C6-C21)아릴, 또는 치환 또는 비치환된 (5-21원)헤테로아릴이고;
상기 L1 은 단일 결합, 치환 또는 비치환된 (C6-C21)아릴렌, 또는 치환 또는 비치환된 (5-21원)헤테로아릴렌이고;
상기 L2 는 치환 또는 비치환된 (C1-C20)알킬렌, 치환 또는 비치환된 (C6-C21)아릴렌, 또는 치환 또는 비치환된 (5-21원)헤테로아릴렌이고;
상기 R1 및 R2은 각각 독립적으로 수소, 치환 또는 비치환된 (C1-C20)알킬, 치환 또는 비치환된 (C6-C21)아릴, 치환 또는 비치환된 (5-21원)헤테로아릴, 또는 -N(R11)(R12)이고;
상기 R11 및 R12는 각각 독립적으로 치환 또는 비치환된 (C6-C21)아릴이며;
상기 n 및 m은 각각 독립적으로 0 내지 1의 정수이고, 단, n과 m이 동시에 0이 될 수 없고;
상기 a는 1 내지 3의 정수이고, a가 2 이상의 정수인 경우 각각의 R1은 동일하거나 상이할 수 있으며;
상기 b는 1 내지 6의 정수이고, b가 2 이상의 정수인 경우 각각의 R2는 동일하거나 상이할 수 있으며;
상기 헤테로아릴(렌)은 N, O 및 S 로부터 선택된 하나 이상의 헤테로원자를 포함하는, 유기 전계 발광 화합물.2. The method of claim 1, wherein Ar 1 to Ar 4 each independently represent a substituted or unsubstituted (C6-C21) aryl or substituted or unsubstituted (5-21 W) and the heteroaryl group, Ar 1 and Ar 2 is a fused ring Lt; / RTI >
Wherein Ar 5 is substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6 -C 21) aryl, or substituted or unsubstituted (5-21 member) heteroaryl;
Wherein L < 1 > is a single bond, substituted or unsubstituted (C6-C21) arylene, or substituted or unsubstituted (5-21 membered) heteroarylene;
Wherein L 2 is substituted or unsubstituted (C 1 -C 20) alkylene, substituted or unsubstituted (C 6 -C 21) arylene, or substituted or unsubstituted (5-21 member) heteroarylene;
Wherein R 1 and R 2 are each independently selected from the group consisting of hydrogen, substituted or unsubstituted (C 1 -C 20) alkyl, substituted or unsubstituted (C 6 -C 21) aryl, substituted or unsubstituted (5-21 membered) or -N (R 11) (R 12 ) a;
R 11 and R 12 are each independently a substituted or unsubstituted (C 6 -C 21) aryl;
And n and m are each independently an integer of 0 to 1, provided that n and m can not be 0 at the same time;
A is an integer of 1 to 3, and when a is an integer of 2 or more, each R 1 may be the same or different;
B is an integer of 1 to 6, and when b is an integer of 2 or more, each R 2 may be the same or different;
Wherein said heteroaryl (R) comprises at least one heteroatom selected from N, O and S. 제1항에 있어서, 상기 Ar1 내지 Ar4은 치환 또는 비치환된 (C6-C21)아릴이고, 여기서 상기 (C6-C21)아릴의 치환체는 (C1-C30)알킬, (C1-C10)알킬로 치환 또는 비치환된 (C6-C21)아릴, 및 (C6-C12)아릴로 치환 또는 비치환된 (5-21원)헤테로아릴로 이루어진 군에서 선택되는 하나 이상일 수 있고, Ar1과 Ar2는 융합하여 고리를 형성할 수 있고;
상기 Ar5 는 비치환된 (C1-C10)알킬; (C1-C10)알킬, (C6-C21)아릴, (6-21원)헤테로아릴 또는 디(C6-C18)아릴아미노로 치환 또는 비치환된 (C6-C18)아릴; 또는 N, O 및 S로부터 선택된 헤테로원자를 포함하고 (C1-C10)알킬 또는 (C6-C18)아릴로 치환 또는 비치환된 (6-21)원 헤테로아릴일 수 있고;
상기 L1 은 단일 결합; (C1-C10)알킬로 치환 또는 비치환된 (C6-C18)아릴렌; 또는 헤테로원자로서 질소 원자를 포함하고 (C1-C10)알킬로 치환 또는 비치환된 (5-18원)헤테로아릴렌이고;
상기 L2 는 비치환된 (C1-C10)알킬렌; (C1-C10)알킬로 치환 또는 비치환된 (C6-C18)아릴렌; 또는 헤테로원자로서 산소 원자를 포함하고 (C1-C10)알킬로 치환 또는 비치환된 (6-21원)헤테로아릴렌이고;
상기 R1 및 R2은 각각 독립적으로 수소; 비치환된 (C6-C18)아릴; 헤테로원자로서 질소 원자를 포함하고 비치환된 (6-18원)헤테로아릴; 또는 -N(R11)(R12)이고;
상기 R11 및 R12는 각각 독립적으로 비치환된 (C6-C18)아릴이고;
상기 n 및 m은 각각 독립적으로 0 내지 1의 정수이고, 단, n과 m이 동시에 0이 될 수 없고;
상기 a는 1이고;
상기 b는 1인, 유기 전계 발광 화합물.The compound of claim 1 wherein Ar 1 to Ar 4 are substituted or unsubstituted (C6-C21) aryl wherein the substituent of the (C6-C21) aryl is selected from the group consisting of (C1-C30) unsubstituted or substituted by (C6-C21) aryl, and (C6-C12) aryl, and to be at least one selected from the group consisting of substituted or unsubstituted (5-21 membered) heteroaryl, Ar 1 and Ar 2 Can be fused to form a ring;
Ar < 5 > is unsubstituted (C1-C10) alkyl; (C6-C18) aryl unsubstituted or substituted with (C1-C10) alkyl, (C6-C21) aryl, (6-21) heteroaryl or di (C6-C18) arylamino; Or (6-21) membered heteroaryl comprising a heteroatom selected from N, O and S and substituted or unsubstituted with (C1-C10) alkyl or (C6-C18) aryl;
L < 1 > is a single bond; (C6-C18) arylene substituted or unsubstituted with (C1-C10) alkyl; Or (5-18 member) heteroarylene which contains a nitrogen atom as a hetero atom and which is substituted or unsubstituted with (C1-C10) alkyl;
Wherein L 2 is unsubstituted (C1-C10) alkylene; (C6-C18) arylene substituted or unsubstituted with (C1-C10) alkyl; Or a (6-21 membered) heteroarylene containing an oxygen atom as a hetero atom and being substituted or unsubstituted with (C1-C10) alkyl;
R 1 and R 2 are each independently hydrogen; Unsubstituted (C6-C18) aryl; An unsubstituted (6-18 membered) heteroaryl containing a nitrogen atom as the hetero atom; Or -N (R 11) (R 12 ) a;
Wherein R 11 and R 12 are each independently unsubstituted (C 6 -C 18) aryl;
And n and m are each independently an integer of 0 to 1, provided that n and m can not be 0 at the same time;
Wherein a is 1;
And b is 1, the organic electroluminescent compound. 제1항에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물로 이루어진 군으로부터 선택되는, 유기 전계 발광 화합물.
Figure pat00075

Figure pat00076

Figure pat00077

Figure pat00078

Figure pat00079

Figure pat00080

Figure pat00081

Figure pat00082

Figure pat00083

Figure pat00084

Figure pat00085

Figure pat00086

Figure pat00087

Figure pat00088

Figure pat00089

Figure pat00090

Figure pat00091

Figure pat00092

Figure pat00093

Figure pat00094

Figure pat00095

Figure pat00096

Figure pat00097
The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following compounds.
Figure pat00075

Figure pat00076

Figure pat00077

Figure pat00078

Figure pat00079

Figure pat00080

Figure pat00081

Figure pat00082

Figure pat00083

Figure pat00084

Figure pat00085

Figure pat00086

Figure pat00087

Figure pat00088

Figure pat00089

Figure pat00090

Figure pat00091

Figure pat00092

Figure pat00093

Figure pat00094

Figure pat00095

Figure pat00096

Figure pat00097
 제1항에 기재된 유기 전계 발광 화합물을 포함하는, 유기 전계 발광 소자.An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
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