KR20140044043A - Novel organic electroluminescence compounds and organic electroluminescence device containing the same - Google Patents

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

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KR20140044043A
KR20140044043A KR1020120109953A KR20120109953A KR20140044043A KR 20140044043 A KR20140044043 A KR 20140044043A KR 1020120109953 A KR1020120109953 A KR 1020120109953A KR 20120109953 A KR20120109953 A KR 20120109953A KR 20140044043 A KR20140044043 A KR 20140044043A
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substituted
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membered
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heteroaryl
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안희춘
양정은
이태진
박소미
이경주
권혁주
김봉옥
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롬엔드하스전자재료코리아유한회사
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Priority to KR1020120109953A priority Critical patent/KR20140044043A/en
Priority to PCT/KR2013/008868 priority patent/WO2014054898A1/en
Priority to TW102135967A priority patent/TW201432022A/en
Publication of KR20140044043A publication Critical patent/KR20140044043A/en

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Abstract

The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same. The compound according to the present invention improves light emitting properties and lifetime properties. Moreover, the compound according to the present invention can provide an organic electroluminescent device with improved light emitting properties and current efficiency.

Description

신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자{Novel organic electroluminescence compounds and organic electroluminescence device containing the same}Novel organic electroluminescence compounds and organic electroluminescence device containing the same

본 발명은 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다. The present invention relates to a novel organic electroluminescent 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[참조: Appl. Phys. Lett. 51, 913, 1987].Among display devices, an electroluminescence device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response speed. In 1987, Eastman Kodak Company first developed an organic EL device using an aromatic diamine and an aluminum complex having a low molecular weight 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 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 for determining the luminous efficiency in the organic EL device is the luminescent material. As a luminescent material, a fluorescent luminescent material has been widely used, but the development of a phosphorescent luminescent material has been extensively studied in view of the fact that phosphorescent luminescent material can improve luminescent efficiency up to 4 times theoretically compared to a fluorescent luminescent material in 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 Ir (btp) 2 ], tris (2-phenylpyridine) iridium [Ir (ppy) 3 ] And bis (4,6-difluorophenylpyridinate-N, C2) picolinato is iridium [Firpic] are known.

발광 재료는 색순도, 발광 효율 및 안정성을 향상시키기 위해 호스트 재료에 발광 재료(도펀트)를 혼합하여 사용하기도 한다. 이와 같은 발광 재료(도펀트)/호스트 재료 체계를 사용할 때, 호스트 재료는 발광 소자의 효율과 성능에 큰 영향을 미치므로, 그 선택이 중요하다. 종래 기술에서, 인광용 호스트 재료로는 4,4’-N,N'-디카르바졸-비페닐(CBP)이 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 EL 소자를 개발한 바 있다.The light emitting material may be a mixture of a light emitting material (dopant) and a host material in order to improve color purity, luminous efficiency and stability. When using such a light emitting material (dopant) / host material system, the selection is important because the host material has a great influence on the efficiency and performance of the light emitting device. In the prior art, 4,4'-N, N'-dicarbazole-biphenyl (CBP) was most widely known as a 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 to develop a high-performance organic EL device.

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, the conventional phosphorescent host materials are advantageous from the viewpoint of luminescence characteristics, but they have the following disadvantages: (1) the material is changed when the glass transition temperature is low and the thermal stability is low and the high temperature deposition process is performed 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) In addition, when used in an organic EL device, it is unsatisfactory in terms of operating life, and luminous efficiency is still required to be improved.

한편, 유기 EL 소자에서 정공 주입 및 수송 재료로서 구리 프탈로시아닌(CuPc), 4,4'-비스[N-(1-나프틸)-N-페닐아미노]바이페닐(NPB), N,N'-디페닐-N,N'-비스(3-메틸페닐)-(1,1'-바이페닐)-4,4'-다이아민(TPD), 4,4',4"-트리스(3-메틸페닐페닐아미노)트리페닐아민(MTDATA) 등이 사용되어 왔으나, 이러한 물질을 사용한 경우 유기 EL 소자는 양자 효율 및 수명이 저하되는 문제가 있었다. 그 이유는 유기 EL 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. On the other hand, in the organic EL device, as a hole injecting and transporting material, copper phthalocyanine (CuPc), 4,4'-bis [N- (1-naphthyl) -N- phenylamino] biphenyl (NPB) (TPD), 4,4 ', 4 "-tris (3-methylphenylphenyl) -4,4'-diamine Amino) triphenylamine (MTDATA). However, when such a material is used, there is a problem that the quantum efficiency and lifetime of the organic EL device are lowered because when the organic EL device is driven at a high current, Since the thermal stress is generated between the hole injection layers and the lifetime of the device is rapidly lowered due to the thermal stress. Further, since the organic material used for the hole injection layer has a very high hole mobility, The electron-hole charge balance is broken and the quantum efficiency (cd / A) is lowered.

한국 공개특허공보 제2011-0129766호는 카바졸이 벤조푸란, 벤조티오펜과 같은 헤테로아릴과 융합되어 형성된 다환계 화합물의 탄소 위치에 아릴 또는 헤테로아릴이 결합된 화합물을 유기 전계 발광 소자용 화합물로 개시하고 있다. 그러나, 상기 문헌에 개시된 화합물들을 포함한 유기 EL 소자들은 전력 효율, 발광 효율, 양자 효율 및 수명 등의 측면에서 여전히 만족스럽지 않다. Korean Unexamined Patent Publication No. 2011-0129766 discloses a compound in which an aryl or heteroaryl is bonded to a carbon position of a polycyclic compound formed by carbazole fused with a heteroaryl such as benzofuran or benzothiophene as a compound for an organic EL device. It is starting. However, organic EL devices including the compounds disclosed in the above documents are still unsatisfactory in terms of power efficiency, luminous efficiency, quantum efficiency, and lifetime.

한국 공개특허공보 제2011-0129766호 (2011.12.02 공개)Korean Unexamined Patent Publication No. 2011-0129766 (published Dec. 2, 2011)

따라서 본 발명의 목적은 첫째, 기존의 재료보다 발광 효율 및 소자 수명이 우수한 유기 전계 발광 화합물을 제공하는 것이며, 둘째, 상기 유기 전계 발광 화합물을 포함하는 고효율 및 장수명의 유기 전계 발광 소자를 제공하는 것이다. Accordingly, an object of the present invention is to firstly provide an organic electroluminescent compound having better luminous efficiency and device life than conventional materials, and secondly, to provide a high efficiency and long life organic electroluminescent device including the organic electroluminescent compound. .

상기의 기술적 과제를 해결하기 위해 예의 연구한 결과, 본 발명자들은 하기 화학식 1로 표시되는 화합물이 상술한 목적을 달성함을 발견하여 본 발명을 완성하였다.As a result of earnest research to solve the above technical problem, the present inventors have found that the compound represented by the following Chemical 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,

X는 -O-, -S-, -CR1R2- 또는 -NR3-이고;X is -O-, -S-, -CR 1 R 2 -or -NR 3- ;

L1은 치환 또는 비치환된 (5-30원)헤테로아릴렌, 또는 치환 또는 비치환된 (C6-C30)아릴렌이고;L 1 is substituted or unsubstituted (5- to 30-membered) heteroarylene, or substituted or unsubstituted (C6-C30) arylene;

Ar1 내지 Ar4는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C6-C30)아릴렌, 치환 또는 비치환된 (5-30원)헤테로아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이거나;Ar 1 to Ar 4 are each independently substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (5- to 30-membered) heteroaryl, or substituted Or unsubstituted (5- to 30-membered) heteroarylene;

Ar1과 Ar2 또는 Ar3와 L1은 결합하고 있는 질소와 함께 질소 함유 (5-30원)헤테로아릴을 형성할 수 있고;Ar 1 and Ar 2 or Ar 3 and L 1 may form a nitrogen containing (5- to 30-membered) heteroaryl together with the nitrogen to which they are bound;

R1 내지 R3 는 각각 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원) 헤테로아릴이거나, 인접한 치환체와 함께 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고;R 1 to R 3 Are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, or with adjacent substituents (3 -30 membered) monocyclic or polycyclic alicyclic or aromatic rings;

R4 및 R5는 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (3-7원) 헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, -NR11R12, -SiR13R14R15, -SR16, -OR17, -COR18 또는 -B(OR19)(OR20)이고;R 4 and R 5 are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl , Substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) Heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , -COR 18 or -B (OR 19 ) (OR 20 );

R11 내지 R20은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알케닐, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이거나, 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있으며;R 11 to R 20 are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl , Substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cyclo Alkenyl, substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl or linked to an adjacent substituent To form a (3-30 membered) monocyclic or polycyclic alicyclic or aromatic ring, 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;

m 및 n은 각각 독립적으로 1 내지 4의 정수이며, 2 이상의 정수인 경우 각각의 R4 및 각각의 R5는 동일하거나 상이할 수 있고;m and n are each independently integers of 1 to 4, and when integers of 2 or more, each of R 4 and each R 5 may be the same or different;

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

본 발명에 따른 화합물은 발광 효율이 우수하고 수명 특성이 뛰어나다. 또한, 본 발명에 따른 화합물은 발광 특성이 우수하고 전류 효율이 향상된 유기 전계 발광 소자를 제공할 수 있다.The compound according to the present invention has excellent luminous efficiency and excellent lifespan characteristics. In addition, the compound according to the present invention can provide an organic electroluminescent device having excellent light emission characteristics and improved current efficiency.

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 전계 발광 화합물, 상기 유기 전계 발광 화합물을 포함하는 유기 전계 발광 재료 및 상기 재료를 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 comprising the material.

본 발명의 상기 화학식 1로 표시되는 화합물에 대해 보다 구체적으로 설명하면 다음과 같다.Hereinafter, the compound represented by Chemical Formula 1 of the present invention will be described in more detail.

상기 화학식 1에서, 바람직하게는, In the above formula (1), preferably,

X는 -O-, -S-, -CR1R2- 또는 -NR3-이고;X is -O-, -S-, -CR 1 R 2 -or -NR 3- ;

L1은 치환 또는 비치환된 (C6-C30)아릴렌이고;L 1 is substituted or unsubstituted (C6-C30) arylene;

Ar1 내지 Ar4는 각각 독립적으로 치환 또는 비치환된 (C6-C15)아릴, 치환 또는 비치환된 (C6-C15)아릴렌, 치환 또는 비치환된 (5-15원)헤테로아릴, 또는 치환 또는 비치환된 (5-15원)헤테로아릴렌이거나, Ar1과 Ar2 또는 Ar3와 L1은 결합하고 있는 질소와 함께 질소 함유 (5-15원)헤테로아릴을 형성할 수 있고;Ar 1 to Ar 4 are each independently substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted (C6-C15) arylene, substituted or unsubstituted (5- to 15-membered) heteroaryl, or substituted Or unsubstituted (5- to 15-membered) heteroarylene, or Ar 1 and Ar 2 or Ar 3 and L 1 may form a nitrogen-containing (5- to 15-membered) heteroaryl together with the nitrogen to which it is bound;

R1 내지 R3 는 각각 독립적으로 치환 또는 비치환된 (C1-C15)알킬, 치환 또는 비치환된 (C6-C15)아릴, 또는 치환 또는 비치환된 (5-15원)헤테로아릴이고; R 1 to R 3 Are each independently substituted or unsubstituted (C1-C15) alkyl, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (5- to 15-membered) heteroaryl;

R4 및 R5는 각각 독립적으로 수소, 할로겐, 치환 또는 비치환된 (C1-C10)알킬, 치환 또는 비치환된 (C6-C15)아릴, 치환 또는 비치환된 (5-15원)헤테로아릴 또는 -SiR13R14R15이고;R 4 and R 5 are each independently hydrogen, halogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted (5- to 15-membered) heteroaryl Or -SiR 13 R 14 R 15 ;

R13 내지 R15은 각각 독립적으로 치환 또는 비치환된 (C1-C10)알킬이다.R 13 to R 15 are each independently substituted or unsubstituted (C1-C10) alkyl.

상기 화학식 1에서, 보다 바람직하게는, In Formula 1, more preferably,

X는 -O-, -S-, -CR1R2- 또는 -NR3-이고;X is -O-, -S-, -CR 1 R 2 -or -NR 3- ;

L1은 치환 또는 비치환된 (C6-C15)아릴렌이고;L 1 is substituted or unsubstituted (C6-C15) arylene;

Ar1 내지 Ar4는 각각 독립적으로 비치환된 (C6-C15)아릴, 비치환된 (C6-C15)아릴렌, 치환 또는 비치환된 (5-15원)헤테로아릴, 또는 치환 또는 비치환된 (5-15원)헤테로아릴렌이거나, Ar1과 Ar2 또는 Ar3와 L1은 결합하고 있는 질소와 함께 질소 함유 (5-15원)헤테로아릴을 형성할 수 있고;Ar 1 to Ar 4 are each independently unsubstituted (C6-C15) aryl, unsubstituted (C6-C15) arylene, substituted or unsubstituted (5- to 15-membered) heteroaryl, or substituted or unsubstituted (5-15 membered) heteroarylene, or Ar 1 and Ar 2 or Ar 3 and L 1 together with the nitrogen to which they are bound may form a nitrogen containing (5-15 membered) heteroaryl;

R1 및 R2는 각각 독립적으로 치환 또는 비치환된 (C1-C10)알킬, 또는 치환 또는 비치환된 (C6-C15)아릴이고;R 1 and R 2 are each independently substituted or unsubstituted (C1-C10) alkyl, or substituted or unsubstituted (C6-C15) aryl;

R3은 치환 또는 비치환된 (C6-C15)아릴이고;R 3 is substituted or unsubstituted (C6-C15) aryl;

R4 및 R5는 각각 독립적으로 수소, 비치환된 (C1-C10)알킬 또는 -SiR13R14R15이고;R 4 and R 5 are each independently hydrogen, unsubstituted (C1-C10) alkyl or -SiR 13 R 14 R 15 ;

R13 내지 R15은 각각 독립적으로 치환 또는 비치환된 (C1-C10)알킬이다.R 13 to R 15 are each independently substituted or unsubstituted (C1-C10) alkyl.

본 발명에 기재되어 있는 “(C1-C30)알킬”은 탄소수가 1 내지 30개인 직쇄 또는 분지쇄 알킬을 의미하고, 여기에서 탄소수가 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 “(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 15개인 것이 바람직하다. 상기 아릴의 예로서, 페닐, 비페닐, 터페닐, 나프틸, 플루오레닐, 페난트레닐, 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 아릴 기를 의미한다. 여기에서 환 골격 원자수가 5 내지 15개인 것이 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.The "(C1-C30) alkyl" described in the present invention means straight chain or branched chain alkyl having 1 to 30 carbon atoms, more preferably having 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 and 1-methylpent-2-onyl. 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. 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. As used herein, the term "(C6-C30) aryl (phenylene)" means a single ring or fused ring radical derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, wherein the number of carbon atoms in the ring is 6 to 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, 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. Here, it is preferable that the number of the ring skeleton atoms is 5 to 15. 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, pyrazinyl, pyrimidinyl and pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, di Benzoimidazolyl, benzothiazolyl, benzothiazolyl, benzoisothiazolyl, benzooxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, Fused heterocyclic heteroaryl such as norbornyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxaphyl, phenanthridinyl, benzodioxolyl and the like. "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 1 에서, 치환 알킬, 치환 알케닐, 치환 알키닐, 치환 알콕시, 치환 시클로알킬, 치환 시클로알케닐, 치환 헤테로시클로알킬, 치환 아릴(렌), 또는 치환 헤테로아릴(렌)의 치환체는 서로 독립적으로 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, (C1-C30)알킬, 할로(C1-C30)알킬, (C2-C30)알케닐, (C2-C30)알키닐, (C1-C30)알콕시, (C1-C30)알킬티오, (C3-C30)시클로알킬, (C3-C30)시클로알케닐, (3-7원)헤테로시클로알킬, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C6-C30)아릴로 치환되거나 비치환된 (5-30원)헤테로아릴, (5-30원)헤테로아릴로 치환되거나 비치환된 (C6-C30)아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, 아미노, 모노 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, (C6-C30)아릴(5-30원)헤테로아릴아미노, (C1-C30)알킬카보닐, (C1-C30)알콕시카보닐, (C6-C30)아릴카보닐, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬 및 (C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 1종 이상인 것이 바람직하다. Also, in the term "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, substituted alkyl, substituted alkenyl, substituted alkynyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl, substituted aryl (ene), or substituted heteroaryl (lene) substituents Independently deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30) alkyl, halo (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1 -C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3-7 membered) heterocycloalkyl, (C6-C30) aryloxy, (C6 -C30) arylthio, (5- to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl, (C6-C30) aryl, unsubstituted or substituted by (5--30 membered) heteroaryl, tri ( C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, amino, mono or Di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C1-C30) alkyl (C6-C30) aryl Mino, (C6-C30) aryl (5--30membered) heteroarylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30 ) Arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6-C30) ar (C1-C30) alkyl and (C1-C30) It is preferably at least one member selected from the group consisting of alkyl (C6-C30) aryl.

본 발명에 따른 화합물로는 대표적으로 하기의 화합물을 들 수 있다.Representative examples of the compound according to the present invention include 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

Figure pat00019
Figure pat00019

Figure pat00020
Figure pat00020

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

본 발명에 따른 화합물은 당업자에게 공지된 합성 방법으로 제조할 수 있으며, 예를 들면 하기 반응식 1에 따라 제조할 수 있다.The compounds according to the invention can be prepared by synthetic methods known to those skilled in the art, for example, according to Scheme 1 below.

[반응식 1][Reaction Scheme 1]

Figure pat00025
Figure pat00025

본 발명은 화학식 1의 유기 전계 발광 화합물을 포함하는 유기 전계 발광 재료 및 상기 재료를 포함하는 유기 전계 발광 소자를 제공한다. 상기 재료는 본 발명의 유기 전계 발광 화합물 단독으로 이루어질 수 있고, 유기 전계 발광 재료에 포함되는 통상의 물질들을 추가로 포함할 수도 있다. 본 발명에 따른 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 갖고, 상기 유기물층은 상기 화학식 1의 화합물을 하나 이상 포함한다.The present invention provides an organic electroluminescent material comprising an organic electroluminescent compound of Formula 1 and an organic electroluminescent device comprising the material. The material may be composed of the organic electroluminescent compound of the present invention alone, and may further include conventional materials included in the organic electroluminescent material. 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 제1 전극과 제2전극 중 하나는 애노드이고 다른 하나는 캐소드일 수 있다. 상기 유기물층은 발광층을 포함하고, 정공 주입층, 정공 수송층, 전자 전달층, 전자 주입층, 계면층(interlayer) 및 정공 차단층에서 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 layer may include a light emitting layer, and may further include one or more layers selected from 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 있다. 상기 발광층은 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 a hole transporting layer, the compound of Formula 1 of the present invention can be included as a hole transporting material. When used in the light emitting layer, the compound of Formula 1 of the present invention can be included as a host material. The light emitting layer may preferably further include one or more dopants, and if necessary, may further include a compound other than the compound of Formula 1 of the present invention as a second host material.

상기 제2호스트 재료는 공지된 인광 호스트라면 어느 것이든 사용 가능하나, 하기 화학식 2 내지 화학식 4로 표시되는 화합물로 구성된 군으로부터 선택되는 것이 발광 효율 면에서 특히 바람직하다. The second host material may be any known phosphorescent host, but is preferably selected from the group consisting of compounds represented by the following formulas (2) to (4) in view of luminous efficiency.

[화학식 2](2)

H-(Cz-L4)h-M H- (Cz-L 4) h -M

[화학식 3](3)

H-(Cz)i-L4-MH- (Cz) i -L 4 -M

[화학식4][Chemical Formula 4]

Figure pat00026
Figure pat00026

상기 화학식 2 내지 4에서,In the above Chemical Formulas 2 to 4,

Cz는 하기 구조이며, Cz has the following structure,

Figure pat00027
Figure pat00027

R21 내지 R24은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원) 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)- 또는 -C(R32)(R33)-이고, Y1과 Y2가 동시에 존재하지는 않으며; R31 내지 R33은 각각 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 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 m 은 각각 독립적으로 0 내지 4의 정수이며, h, i, j, k, l 또는 m이 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 ) — or —C (R 32 ) (R 33 ) —, wherein Y 1 and Y 2 are not present simultaneously; R 31 to R 33 are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, and 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 m are each independently an integer of 0 to 4, and when h, i, j, k, l or m 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 제2 호스트 재료의 바람직한 예는 다음과 같다.Specifically, preferred examples of the second host material are as follows.

Figure pat00028
Figure pat00028

Figure pat00029
Figure pat00029

Figure pat00030
Figure pat00030

Figure pat00031
Figure pat00031

Figure pat00032
Figure pat00032

Figure pat00033
Figure pat00033

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

본 발명의 유기 전계 발광 소자 제조에 사용되는 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 used in the organic electroluminescent device of the present invention, at least one phosphorescent dopant is preferable. The phosphorescent dopant material to be applied to the organic electroluminescent device of the present invention is not particularly limited, but is preferably a complex compound of a metal atom selected from iridium (Ir), osmium (Os), copper (Cu) and platinum (Pt) , An iridium (Ir), an osmium (Os), a copper (Cu) and a platinum (Pt) are more preferable, and an orthometallated iridium complex compound is even more preferable.

상기 인광 도펀트는 하기 화학식 5로 표시되는 화합물로 구성된 군으로부터 선택되는 것이 바람직하다.The phosphorescent dopant is preferably selected from the group consisting of compounds represented by the following formula (5).

[화학식 5] [화학식 6] [화학식 7][Formula 5] [Formula 6] [Formula 7]

Figure pat00041
Figure pat00042
Figure pat00043
Figure pat00041
Figure pat00042
Figure pat00043

상기 화학식 5 내지 7에서, L은 하기 구조 중에서 선택되고;In Chemical Formulas 5 to 7, L is selected from the following structures;

Figure pat00044
Figure pat00044

R100은 수소, 또는 치환 또는 비치환된 (C1-C30)알킬이며; R101 내지 R109 및 R111 내지 R123은 각각 독립적으로 수소, 중수소, 할로겐, 할로겐이 치환 또는 비치환된 (C1-C30)알킬, 시아노, 또는 치환 또는 비치환된 (C1-C30)알콕시이고; R120 내지 R123는 인접 치환기가 서로 연결되어 융합고리를 형성하는데, 예를 들어 퀴놀린 형성이 가능하며; R124 내지 R127은 각각 독립적으로 수소, 중수소, 할로겐, 치환 또는 비치환된 (C1-C30)알킬, 또는 치환 또는 비치환된 (C1-C30)아릴이며; R124 내지 R127가 아릴기인 경우 인접기가 서로 연결되어 융합고리를 형성하는데, 예를 들어 플루오렌 형성이 가능하며; R201 내지 R211은 각각 독립적으로 수소, 중수소, 할로겐, 또는 할로겐이 치환 또는 비치환된 (C1-C30)알킬이며; f 및 g는 각각 독립적으로 1 내지 3의 정수이며, f 또는 g가 각각 2이상의 정수인 경우 각각의 R100은 서로 동일하거나 상이할 수 있고; n은 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, (C 1 -C 30) alkyl, substituted or unsubstituted (C 1 -C 30) alkyl, cyano, or substituted or unsubstituted (C 1 -C 30) alkoxy; R 120 to R 123 are adjacent substituents connected to each other to form a fused ring, for example, quinoline formation is possible; R 124 to R 127 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C1-C30) aryl; When R 124 to R 127 are aryl groups, the adjacent groups are connected to each other to form a fused ring, for example, fluorene formation is possible; R 201 To R 211 are each independently hydrogen, deuterium, halogen, or (C1-C30) alkyl substituted or unsubstituted with halogen; f and g are each independently an integer of 1 to 3, and when f or g is an integer of 2 or more, each 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 pat00045
Figure pat00045

Figure pat00046
Figure pat00046

Figure pat00047
Figure pat00047

Figure pat00048
Figure pat00048

Figure pat00049
Figure pat00049

Figure pat00050
Figure pat00050

Figure pat00051
Figure pat00051

Figure pat00052
Figure pat00052

Figure pat00053
Figure pat00053

Figure pat00054
Figure pat00054

Figure pat00055
Figure pat00055

Figure pat00056
Figure pat00056

본 발명은 추가의 양태로 유기 전계 발광소자 제조용 재료를 제공한다. 상기 재료는 호스트 재료 또는 정공 수송층 재료로서 본 발명의 화합물을 포함한다. 본 발명의 화합물이 호스트 재료로 포함될 경우 상기 재료는 제2 호스트 재료를 추가로 포함할 수 있으며, 이때 제1 호스트 재료와 제2 호스트 재료의 중량비는 1:99 내지 99:1 범위이다.The present invention further provides a material for manufacturing an organic electroluminescent device in a further aspect. The material includes the compound of the present invention as a host material or a hole transporting layer material. When the compound of the present invention is contained as a host material, the material 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.

또한, 본 발명의 유기 전계 발광 소자는 제1전극; 제2전극; 및 상기 제1전극과 제2전극 사이에 개재되는 1층 이상의 유기물층을 가지며, 상기 유기물층은 본 발명의 유기 전계 발광 소자용 재료를 포함한다.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 the material for the organic electroluminescence device of the present invention.

본 발명의 유기 전계 발광 소자는 유기물층이 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 at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound.

또한, 본 발명의 유기 전계 발광 소자에 있어서, 유기물층에 상기 화학식 1의 화합물 이외에 1족, 2족, 4주기, 5주기 전이금속, 란탄 계열 금속 및 d-전이원소의 유기 금속으로 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 containing a blue, red or green light emitting compound known in the art, in addition to the compound of the present invention. Further, if necessary, it may further include a yellow or orange light emitting layer.

본 발명의 유기 전계 발광 소자에 있어서, 한 쌍의 전극의 적어도 한쪽의 내측 표면에, 칼코제나이드(chalcogenide)층, 할로겐화 금속층 및 금속 산화물층으로부터 선택되는 1층(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 halogenated metal layer and a metal oxide layer on at least one inner surface of a pair of electrodes (hereinafter, these are referred to as "surface layers"). ) It is preferable to arrange the above. 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. Preferred examples of the chalcogenide are SiO X (1 = X = 2), AlO X (1 = X = 1.5), SiON or SiAlON, and the preferred examples of the metal halide are LiF, MgF 2 , CaF 2 , fluoride Rare earth metals and the like, and 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 도펀트의 혼합 영역 또는 정공 수송 화합물과 산화성 도펀트의 혼합 영역을 배치하는 것도 바람직하다. 이러한 방식에 의해 전자 전달 화합물이 음이온으로 환원되므로 혼합 영역으로부터 발광 매체에 전자를 주입 및 전달하기 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 전하 생성층으로 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 transfer 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, 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 transporting 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. Further, a white organic electroluminescent device having two or more light emitting layers can be manufactured using a reductive dopant layer as a charge generation layer.

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

[실시예 1] 화합물 C-2의 제조Example 1 Preparation of Compound C-2

Figure pat00057
Figure pat00057

화합물 1-1의 제조Preparation of Compound 1-1

2-브로모니트로벤젠 30g(148mmol), 4-다이벤조티오펜 보론산 41g(178mmol), 테트라키스(트리페닐포스핀)팔라듐(O)[Pd(PPh3)4] 6.5g(5.9 mmol), Na2CO3 39g(370mmol), 톨루엔 600mL 및 에탄올(EtOH) 200 mL를 넣고, H2O 200mL를 첨가한 후 120℃로 2시간 동안 교반하였다. 반응이 끝나면 증류수로 씻고 에틸 아세테이트(EA)로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼으로 정제하여 화합물1-1, 39g(86%)을 수득하였다.30 g (148 mmol) of 2-bromonitrobenzene, 41 g (178 mmol) of 4-dibenzothiophene boronic acid, palladium (O) [Pd (PPh 3 ) 4 ] 6.5 g (5.9 mmol) tetrakis (triphenylphosphine) 39 g (370 mmol) of Na 2 CO 3 , 600 mL of toluene and 200 mL of ethanol (EtOH) were added thereto, and 200 mL of H 2 O was added thereto, followed by stirring at 120 ° C. for 2 hours. After the reaction, the mixture was washed with distilled water, extracted with ethyl acetate (EA), the organic layer was dried over MgSO 4 , the solvent was removed with a rotary evaporator, and purified by column to obtain compound 1-1, 39 g (86%).

화합물 1-2의 제조Preparation of Compound 1-2

둥근 바닥 플라스크(RBF)에 2-(다이벤조티오펜-4-일)-니트로벤젠 39g(128mmol), 트리에틸 포스파이트[P(OEt)3] 300mL 및 1,2-다이클로로벤젠 300mL를 넣고 150℃에서 8시간 동안 교반하였다. 진공 증류로 용매를 제거하여 수득한 조 생성물을 컬럼으로 정제하여 화합물 1-2, 21g(61%)을 수득하였다.Into a round bottom flask (RBF) was added 39 g (128 mmol) of 2- (dibenzothiophen-4-yl) -nitrobenzene, 300 mL of triethyl phosphite [P (OEt) 3 ], and 300 mL of 1,2-dichlorobenzene. Stir at 150 ° C. for 8 hours. The crude product obtained by removing the solvent by vacuum distillation was purified by column to give 21 g (61%) of compound 1-2.

화합물 2-1의 제조Preparation of Compound 2-1

4-브로모-2-플루오로니트로벤젠 15g(68mmol), 페닐 보론산 9.1g(75mmol), Pd(PPh3)4 3.5g(4.6mmol), Na2CO3 18g(170mmol), 톨루엔 270mL 및 EtOH 90mL를 넣고, H2O 90mL를 첨가한 후 120℃로 2시간 동안 교반하였다. 반응이 끝나면 증류수로 씻고 EA로 추출한 뒤 유기층을 MgSO4로 건조시킨 후 회전 증발기로 용매를 제거한 후 컬럼으로 정제하여 화합물 2-1, 9.2g(62%)을 수득하였다.15 g (68 mmol) 4-bromo-2-fluoronitrobenzene, 9.1 g (75 mmol) phenyl boronic acid, 3.5 g (4.6 mmol) Pd (PPh 3 ) 4 , 18 g (170 mmol) Na 2 CO 3 , 270 mL toluene and 90 mL of EtOH was added, 90 mL of H 2 O was added thereto, and the mixture was stirred at 120 ° C. for 2 hours. After the reaction was washed with distilled water, extracted with EA, the organic layer was dried with MgSO 4 and the solvent was removed on a rotary evaporator and purified by a column to obtain compound 2-1, 9.2g (62%).

화합물 2-2의 제조Preparation of Compound 2-2

5H-[1]벤조티에노[3,2-c]카바졸 8.8g(40.5mmol)을 180mL의 다이메틸포름아미드(DMF)에 녹이고 NaH 1.9g(60%, 광유 중, 48.6mmol)을 천천히 넣었다. 15분간 교반한 후 이 용액에 20mL DMF에 녹아 있는 4-플루오로-2-페닐니트로벤젠 8.8g(40.5mmol)을 천천히 적가하였다. 반응 용액은 상온에서 4시간 동안 교반하고 메탄올로 급냉하였다. EA/H2O로 끝처리한 조 생성물을 컴럼으로 정제하여 화합물 2-2, 19g(100%)을 수득하였다.Dissolve 8.8 g (40.5 mmol) of 5H- [1] benzothieno [3,2-c] carbazole in 180 mL of dimethylformamide (DMF) and slowly dissolve 1.9 g of NaH (60%, 48.6 mmol in mineral oil). Put in. After stirring for 15 minutes, 8.8 g (40.5 mmol) of 4-fluoro-2-phenylnitrobenzene dissolved in 20 mL DMF was slowly added dropwise to this solution. The reaction solution was stirred at room temperature for 4 hours and quenched with methanol. The crude product, finished with EA / H 2 O, was purified by comum to yield 19 g (100%) of compound 2-2.

화합물 2-3의 제조Preparation of Compound 2-3

RBF에 2-페닐-4-(벤조티에노[3,2-c]카바졸릴)-니트로벤젠 19g(40.3mmol), P(OEt)3 80mL 및 1,2-다이클로로벤젠 120mL를 넣고 150℃ 에서 8시간 동안 교반하였다. 진공 증류로 용매를 제거하여 얻은 조 생성물을 컬럼으로 정제하여 화합물 2-3, 12g(68%)을 수득하였다.Into RBF, 19 g (40.3 mmol) of 2-phenyl-4- (benzothieno [3,2-c] carbazolyl) -nitrobenzene, 80 mL of P (OEt) 3 and 120 mL of 1,2-dichlorobenzene were added and the temperature was 150 ° C. Stirred for 8 h. The crude product obtained by removing the solvent by vacuum distillation was purified by column to give 12 g (68%) of compound 2-3.

화합물 C-2의 제조Preparation of Compound C-2

RBF에 3-(벤조티에노[3,2-c]카바졸릴)-카바졸 10g(22.8mmol), 9-페닐-3-브로모카바졸 8g(25mmol), CuI 2g(11.4 mmol), 에틸렌다이아민 1.5mL(22.8mmol), 칼륨 포스페이트 12g(57mmol) 및 톨루엔 200mL를 넣고 8시간 동안 환류하였다. 반응 혼합물을 상온으로 식힌 후 고체를 여과하여 메틸렌 클로라이드(MC)로 씻었다. 여액을 감압증류하고 컬럼 정제하여 화합물 C-2, 11g(71%)의 생성물을 수득하였다.10 g (22.8 mmol) 3- (benzothieno [3,2-c] carbazolyl) -carbazole in RBF, 8 g (25 mmol) 9-phenyl-3-bromocarbazole, 2 g (11.4 mmol) CuI, ethylenedia 1.5 mL (22.8 mmol) of potassium, 12 g (57 mmol) of potassium phosphate and 200 mL of toluene were added and refluxed for 8 hours. After cooling the reaction mixture to room temperature, the solid was filtered and washed with methylene chloride (MC). The filtrate was distilled under reduced pressure and column purification to give the product of compound C-2, 11g (71%).

UV=308nm, PL=383nm, mp=241℃, MS/EIMS 계산치: 679.21, 실측치: 679.83UV = 308 nm, PL = 383 nm, mp = 241 ° C., MS / EIMS calculated: 679.21, found: 679.83

[실시예 2] 화합물 C-6의 제조Example 2 Preparation of Compound C-6

Figure pat00058
Figure pat00058

화합물 2-4는 실시예 1의 화합물 2-3의 합성법과 동일하게 합성할 수 있다. RBF 250mL에 화합물 2-3 5.9g(14 mmol), 3-브로모-N,N-다이페닐아닐린 5g(15mmol), CuI 1.3g(6.9mmol), K3PO4 8.9g(42mmol), 에틸렌다이아민 1.9ml(28mmol) 및 톨루엔 70mL를 넣고, 120℃로 밤새 교반하였다. 반응 혼합물은 EA/H2O로 끝처리하고, MgSO4로 수분을 제거한 후, 감압증류하였다. 조 생성물을 MC:헥산(Hx)으로 컬럼 크로마토그래피를 통해 화합물 C-6, 6.9g(74%)을 하얀색 고체로 수득하였다.Compound 2-4 can be synthesized in the same manner as in Synthesis of Compound 2-3 of Example 1. 5.9 g (14 mmol) of Compound 2-3, 5 g (15 mmol) of 3-bromo- N, N -diphenylaniline, 1.3 g (6.9 mmol) of CuI, 8.9 g (42 mmol) of K 3 PO 4 , ethylene in 250 mL of RBF 1.9 ml (28 mmol) of diamine and 70 mL of toluene were added and stirred at 120 ° C. overnight. The reaction mixture was finished with EA / H 2 O, dried with MgSO 4 , and then distilled under reduced pressure. The crude product was column chromatographed with MC: hexane (Hx) to give 6.9 g (74%) of compound C-6 as a white solid.

UV =314nm, PL= 381nm, mp= 236℃, MS/EIMS 계산치: 665.25, 실측치: 665.78UV = 314 nm, PL = 381 nm, mp = 236 ° C., MS / EIMS calcd: 665.25, found: 665.78

[실시예 3] 화합물 C-62의 제조Example 3 Preparation of Compound C-62

Figure pat00059
Figure pat00059

화합물 5-1의 제조Preparation of Compound 5-1

2L RBF에 다이페닐아민 20g(118mmol), 4-브로모-4’-요오도페닐 63.6g(177mmol), 트리스(다이벤질리덴아세톤)다이팔라듐(O)[Pd2(dba)3] 3.2g(3.5mmol), 트리(o-톨릴)포스핀[P(o-tol)3] 2.9g(9.4mmol), 나트륨 3급-부톡사이드(NaOtBu) 22.7g(236mmol) 및 톨루엔 1000mL를 넣고, 120 ℃ 하에서 1시간 동안 교반하였다. 반응 혼합물은 EA/H2O 로 끝처리하고, MgSO4로 수분을 제거한후, 감압증류하였다. 조 생성물을 MC:Hx으로 컬럼 크로마토그래피하여, 화합물 5-1 13.4g(28%)을 수득하였다. 20 g (118 mmol) diphenylamine in 2 L RBF, 63.6 g (177 mmol) 4-bromo-4'-iodophenyl, tris (dibenzylideneacetone) dipalladium (O) [Pd 2 (dba) 3 ] 3.2 g (3.5 mmol), tri (o-tolyl) phosphine [P ( o -tol) 3 ] 2.9 g (9.4 mmol), sodium tert-butoxide (NaO t Bu) 22.7 g (236 mmol) and 1000 mL of toluene Put, and stirred for 1 hour under 120 ℃. The reaction mixture was finished with EA / H 2 O, dried with MgSO 4 , and then distilled under reduced pressure. The crude product was column chromatographed with MC: Hx to give 13.4 g (28%) of compound 5-1.

화합물 C-62의 제조Preparation of Compound C-62

RBF 250mL에 화합물 2-4, 6.3g(15mmol), 화합물 5-1, 6.6g(16.5mmol), CuI 1.4g(7.5mmol), K3PO4 9.5g(45mmol), 에틸렌다이아민 2mL(30mmol) 및 톨루엔 75mL를 넣고, 120℃로 8시간 동안 교반하였다. 반응 혼합물은 EA/H2O 로 끝처리하고, MgSO4로 수분을 제거한후, 감압증류하였다. 조 생성물을 MC:Hx으로 컬럼 크로마토그래피를 통해 화합물 C-62, 7.6g(68%)을 하얀색 고체로 수득하였다.In 250 mL RBF, compound 2-4, 6.3 g (15 mmol), compound 5-1, 6.6 g (16.5 mmol), CuI 1.4 g (7.5 mmol), K 3 PO 4 9.5 g (45 mmol), 2 mL (30 mmol) ethylenediamine ) And 75 mL of toluene were added and stirred at 120 ° C. for 8 hours. The reaction mixture was finished with EA / H 2 O, dried with MgSO 4 , and then distilled under reduced pressure. The crude product was column chromatographed with MC: Hx to give 7.6 g (68%) of compound C-62 as a white solid.

UV=344nm, PL=397nm, mp= 173℃ MS/EIMS 계산치: 741.28, 실측치: 741.88UV = 344 nm, PL = 397 nm, mp = 173 ° C. MS / EIMS calcd: 741.28, found: 741.88

[실시예 4] 화합물 C-71의 제조Example 4 Preparation of Compound C-71

Figure pat00060
Figure pat00060

화합물 3-1의 제조Preparation of Compound 3-1

RBF에 화합물 1-2 20g(73mmol), 3-브로모요오도벤젠 41g(146mmol), CuI 7g(36.5mmol), 에틸렌다이아민 9mL(146mmol), 세슘 카보네이트 45g(146mmol) 및 톨루엔 400mL를 넣고 3시간 동안 환류하였다. 반응 혼합물을 상온으로 식힌후 고체는 여과하여 MC로 씻었다. 여액을 감압증류하고 컬럼 크로마토그래피로 정제하여 화합물 3-1, 23g(54%)의 생성물을 수득하였다.Into RBF, add 20 g (73 mmol) of Compound 1-2, 41 g (146 mmol) of 3-bromoiodobenzene, 7 g (36.5 mmol) of CuI, 9 mL (146 mmol) of ethylenediamine, 45 g (146 mmol) of cesium carbonate, and 400 mL of toluene. Reflux for hours. After cooling the reaction mixture to room temperature, the solid was filtered and washed with MC. The filtrate was distilled under reduced pressure and purified by column chromatography to give 23 g (54%) of the product of compound 3-1.

화합물 4-2의 제조Preparation of Compound 4-2

RBF에 화합물 4-1, 25g(77mmol), 아닐린 14g(154mmol), 팔라듐(II) 아세테이트[Pd(OAc)2] 0.35g(1.54mmol), 트리-3급-부틸포스핀[P(tBu)3] 3mL(7.7 mmol), 세슘 카보네이트 50g(154mmol) 및 크실렌 400mL를 넣고 8시간 동안 환류하였다. 반응 혼합물을 상온으로 식힌후 고체는 여과하여 MC로 씻었다. 여액을 감압증류하고 컬럼 정제하여 화합물 4-2, 20g(77%)의 생성물을 수득하였다. Compound 4-1, 25 g (77 mmol), aniline 14 g (154 mmol) in RBF, palladium (II) acetate [Pd (OAc) 2 ] 0.35 g (1.54 mmol), tri-tert-butylphosphine [P (tBu) 3 ] 3mL (7.7 mmol), cesium carbonate 50g (154mmol) and xylene 400mL was added to reflux for 8 hours. After cooling the reaction mixture to room temperature, the solid was filtered and washed with MC. The filtrate was distilled under reduced pressure and column purified to give 20 g (77%) of the product 4-2.

화합물 C-71의 제조Preparation of Compound C-71

RBF에 화합물 3-1, 10g(23.3mmol), 화합물 4-2, 7.9g(23.3mmol), Pd2(dba)3 0.43g(0.47mmol), P(tBu)3 1mL(2.4mmol), 나트륨 3급-부톡사이드 3.5g(35mmol) 및 크실렌 120mL를 넣고 8시간 동안 환류하였다. 반응 혼합물을 상온으로 식힌후 고체는 여과하여 MC로 씻었다. 여액을 감압증류하고 컬럼 정제하여 화합물 C-71, 10.2g(64%)을 수득하였다. RBF Compound 3-1, 10 g (23.3 mmol), Compound 4-2, 7.9 g (23.3 mmol), Pd 2 (dba) 3 0.43 g (0.47 mmol), P (tBu) 3 1 mL (2.4 mmol), sodium 3.5 g (35 mmol) of tert-butoxide and 120 mL of xylene were added and refluxed for 8 hours. After cooling the reaction mixture to room temperature, the solid was filtered and washed with MC. The filtrate was distilled under reduced pressure and column purification to give 10.2 g (64%) of compound C-71.

UV=310nm, PL=383nm, mp=205℃ MS/EIMS 계산치: 683.24, 실측치: 683.86UV = 310 nm, PL = 383 nm, mp = 205 ° C. MS / EIMS calcd: 683.24, found: 683.86

[소자 실시예1] 본 발명에 따른 유기 전계 발광 화합물을 이용한 OLED 소자 제작Device Example 1 Fabrication of an OLED Device Using an Organic Electroluminescent Compound According to the Present Invention

본 발명의 발광 재료를 이용한 구조의 OLED 소자를 제작하였다. 우선, OLED용 글래스(삼성-코닝사 제조)로부터 얻어진 투명전극 ITO 박막(15Ω/□)을, 트리클로로에틸렌, 아세톤, 에탄올 및 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'-디일)비스(N1-(나프탈렌-1-일)-N4,N4-다이페닐벤젠-1,4-다이아민)을 넣고 챔버 내의 진공도가 10-6 torr에 도달할 때까지 배기시킨 후, 셀에 전류를 인가하여 증발시켜 ITO 기판 위에 60nm 두께의 정공 주입층을 증착하였다. 이어서, 진공 증착 장비 내의 다른 셀에C-2를 넣고, 셀에 전류를 인가하여 증발시켜 정공 주입층 위에 20nm 두께의 정공 수송층을 증착하였다. 정공 주입층 및 정공 수송층을 형성시킨 후, 그 위에 발광층을 다음과 같이 증착시켰다. 진공 증착 장비 내의 한쪽 셀에 호스트로서 5-(4-([1,1':4',1''-터페닐]-3-일)피리미딘-2-일)-5H-벤조[4,5]티에노[3,2-c]카바졸을 넣고, 또 다른 셀에는 도펀트로서 D-1을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 도펀트와 호스트 합계량에 대해 도펀트를 15중량%의 양으로 도핑함으로써 상기 정공 수송층위에 30nm 두께의 발광층을 증착하였다. 이어서 상기 발광층 위에 전자 전달층으로서 한쪽 셀에 2-(4-(9,10-다이(나프탈렌-2-일)안트라센-2-일)페닐)-1-페닐-1H-벤조[d]이미다졸을 넣고, 또다른 셀에는 리튬 퀴놀레이트(lithium quinolate)를 각각 넣은 후, 두 물질을 같은 속도로 증발시켜 각각 50중량%의 양으로 도핑함으로써 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. 재료별로 각 화합물은 10-6 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 (15 OMEGA / square) obtained from a glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic cleaning using trichlorethylene, acetone, ethanol and distilled water sequentially and then 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 -diphenylbenzene-1,4-diamine) and evacuated until the vacuum in the chamber reaches 10 -6 torr, and then the current It was applied and evaporated to deposit a 60 nm thick hole injection layer on the ITO substrate. Subsequently, C-2 was placed in another cell in the vacuum deposition apparatus, and a 20 nm-thick hole transport layer was deposited on the hole injection layer by evaporation by applying a current to the cell. A hole injecting layer and a hole transporting layer were formed, and then a light emitting layer was deposited thereon as follows. 5- (4-([1,1 ': 4', 1 ''-terphenyl] -3-yl) pyrimidin-2-yl) -5H-benzo [4, as host in one cell in the vacuum deposition equipment 5] Add thieno [3,2-c] carbazole, add D-1 as a dopant in another cell, and then evaporate the two materials at different rates to 15% by weight of the dopant relative to the total amount of dopant and host. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping in a positive amount. Then, 2- (4- (9,10-di (naphthalen-2-yl) anthracen-2-yl) phenyl) -1-phenyl-1H-benzo [d] imidazole in one cell as an electron transporting layer on the light emitting layer. In another cell, lithium quinolate was added to each cell, and then the two materials were evaporated at the same rate and doped in an amount of 50% by weight, respectively, thereby depositing an electron transport layer having a thickness 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 used by vacuum sublimation purification under 10 -6 torr.

그 결과, 13.1mA/cm2의 전류가 흘렀으며, 5350cd/m2의 녹색 발광이 확인되었다. As a result, a current of 13.1 mA / cm 2 flowed, and green light emission of 5350 cd / m 2 was confirmed.

[소자 실시예 2] 본 발명에 따른 유기 전계 발광 화합물을 이용한 OLED 소자 제작[Device Embodiment 2] Fabrication of OLED device using organic electroluminescent compound according to the present invention

정공 수송층으로서 C-71을 20nm 두께로 증착하고 발광층으로서 진공 증착 장비내의 한쪽 셀에 9-(4-([1,1':3',1''-터페닐]-4-일)피리미딘-2-일)-3-(다이벤조[b,d]티오펜4-일)-9H-카바졸을 넣고, 또 다른 셀에는 도펀트로서 C-71 is deposited to a thickness of 20 nm as a hole transporting layer and 9- (4-([1,1 ': 3', 1 ''-terphenyl] -4-yl) pyrimidine in one cell in the vacuum deposition equipment as a light emitting layer. -2-yl) -3- (dibenzo [b, d] thiophen4-yl) -9H-carbazole, and another cell as dopant

D-25를 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 도펀트와 호스트 합계량에 대해 도펀트를 15중량%의 양으로 도핑함으로써 상기 정공 수송층 위에 30nm 두께의 발광층을 증착한 것 이외에는 소자 실시예1과 동일한 방법으로 OLED소자를 제작하였다.After each of the D-25s, the two materials were evaporated at different rates to dope the dopant in an amount of 15% by weight based on the total amount of the dopant and the host, thereby depositing a 30 nm thick light emitting layer on the hole transport layer. An OLED device was manufactured in the same manner.

그 결과, 24.1 mA/cm2의 전류가 흘렀으며, 11000 cd/m2의 녹색 발광이 확인되었다. As a result, a current of 24.1 mA / cm 2 flowed, and green light emission of 11000 cd / m 2 was confirmed.

[소자 실시예 3] 본 발명에 따른 유기 전계 발광 화합물을 이용한 OLED 소자 제작[Device Embodiment 3] Fabrication of OLED device using organic electroluminescent compound according to the present invention

정공 수송층으로서 C-6을 20nm 두께로 증착하고 발광층으로서 진공 증착 장비내의 한쪽 셀에 9-(4-([1,1'-바이페닐]-4-일)퀴나졸린-2-일)-9'-페닐-9H,9'H-3,3'-바이카바졸을 넣고, 또 다른 셀에는 도펀트로서 D-78을 각각 넣은 후, 두 물질을 다른 속도로 증발시켜 3중량%의 양으로 도핑함으로써 상기 정공 수송층 위에 30nm 두께의 발광층을 증착한 것 이외에는 소자 실시예 1과 동일한 방법으로 OLED 소자를 제작하였다. 그 결과, 50.4mA/cm2의 전류가 흘렀으며, 7000 cd/m2의 적색 발광이 확인되었다. C-6 was deposited to a thickness of 20 nm as a hole transporting layer and 9- (4-([1,1'-biphenyl] -4-yl) quinazolin-2-yl) -9 in one cell in the vacuum deposition equipment as a light emitting layer. Add '-phenyl-9H, 9'H-3,3'-bicarbazole, add D-78 as dopant in another cell, and evaporate the two materials at different rates to dope in 3% by weight. The OLED device was manufactured by the same method as Device Example 1, except that a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. As a result, a current of 50.4 mA / cm 2 flowed, and red light emission of 7000 cd / m 2 was confirmed.

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

정공 수송층으로서 N,N'-다이(4-바이페닐)-N,N'-다이(4-바이페닐)-4,4'-다이아미노바이페닐을 20nm 두께로 증착하였고 발광 재료로서 호스트에는 4,4‘-N,N'-다이카바졸-바이페닐을, 도펀트로는 화합물 Ir(ppy)3(D-15)을 사용하고, 정공 수송층위에 30nm 두께의 발광층을 증착하고, 정공 저지층으로 알루미늄(III) 비스(2-메틸-8-퀴놀리네이토)-4-페닐페놀레이트를 10nm 두께로 증착한 것 외에는 소자 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl as a hole transporting layer was deposited to a thickness of 20 nm and 4 on the host as a light emitting material. , 4'-N, N'-dicarbazole-biphenyl, compound Ir (ppy) 3 (D-15) as a dopant, a light emitting layer having a thickness of 30 nm was deposited on the hole transporting layer, and a hole blocking layer An OLED device was manufactured in the same manner as in Example 1, except that aluminum (III) bis (2-methyl-8-quinolinate) -4-phenylphenolate was deposited to a thickness of 10 nm.

그 결과, 8.30 mA/cm2의 전류가 흘렀으며, 2750 cd/m2의 녹색 발광이 확인되었다. As a result, a current of 8.30 mA / cm 2 flowed, and green light emission of 2750 cd / m 2 was confirmed.

[비교예 2] 종래에 발광 재료를 이용한 OLED 소자 제작[Comparative Example 2] Fabrication of an OLED Device Using a Light-Emitting Material

정공 수송층으로서 N,N'-다이(4-바이페닐)-N,N'-다이(4-바이페닐)-4,4'-다이아미노바이페닐을 20nm 두께로 증착 하였고 발광 재료로서 호스트에는 CBP를, 도펀트로는 D-80을 사용해서 정공 수송층위에 30nm 두께의 발광층을 증착하고 정공 저지층으로 알루미늄(III) 비스(2-메틸-8-퀴놀리네이토)-4-페닐페놀레이트를 10nm 두께로 증착한 것 외에는 소자 실시예 1과 동일한 방법으로 OLED소자를 제작하였다.N, N'-di (4-biphenyl) -N, N'-di (4-biphenyl) -4,4'-diaminobiphenyl was deposited to a thickness of 20 nm as the hole transport layer and CBP was applied to the host as a light emitting material. As a dopant, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer using D-80, and 10 nm of aluminum (III) bis (2-methyl-8-quinolinate) -4-phenylphenolate was used as the hole blocking layer. An OLED device was manufactured in the same manner as in Device Example 1, except that the film was deposited with a thickness.

그 결과, 32.1A/cm2의 전류가 흘렀으며, 1700cd/m2의 적색 발광이 확인되었다.As a result, a current of 32.1 A / cm 2 flowed, and red light emission of 1700 cd / m 2 was confirmed.

본 발명에서 개발한 유기 전계 발광 화합물들의 발광 특성이 종래의 재료 대비 우수한 특성을 보이는 것을 확인할 수 있었다. 또한 본 발명에 따른 유기 전계 발광 화합물을 사용한 소자는 발광 특성이 뛰어나고 전류 효율이 향상된다.It was confirmed that the organic electroluminescent compounds developed in the present invention exhibited excellent luminescent properties compared to the conventional materials. Further, the device using the organic electroluminescent compound according to the present invention has excellent luminescent characteristics and improved current efficiency.

Claims (6)

하기 화학식 1로 표시되는 유기 전계 발광 화합물:
[화학식 1]
Figure pat00061

상기 화학식 1에서,
X는 -O-, -S-, -CR1R2- 또는 -NR3-이고,
L1은 치환 또는 비치환된 (5-30원)헤테로아릴렌, 또는 치환 또는 비치환된 (C6-C30)아릴렌이고;
Ar1 내지 Ar4는 각각 독립적으로 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (C6-C30)아릴렌, 치환 또는 비치환된 (5-30원)헤테로아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴렌이거나;
Ar1과 Ar2 또는 Ar3와 L1은 결합하고 있는 질소와 함께 질소 함유 (5-30원)헤테로아릴을 형성할 수 있고;
R1 내지 R3 는 각각 독립적으로 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 5-30원 헤테로아릴이거나, 인접한 치환체와 함께 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 환을 형성할 수 있고;
R4 및 R5는 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, 치환 또는 비치환된 (C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아릴, 치환 또는 비치환된 (5-30원)헤테로아릴, -NR11R12, -SiR13R14R15, -SR16, -OR17, -COR18 또는 -B(OR19)(OR20)이고;
R11 내지 R20은 각각 독립적으로 수소, 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, 치환 또는 비치환 (C1-C30)알킬, 치환 또는 비치환된 (C2-C30)알케닐, 치환 또는 비치환된 (C2-C30)알키닐, 치환 또는 비치환된 (C1-C30)알콕시, 치환 또는 비치환된 (C3-C30)시클로알킬, 치환 또는 비치환된 (C3-C30)시클로알케닐, 치환 또는 비치환된 (3-7원)헤테로시클로알킬, 치환 또는 비치환된 (C6-C30)아릴, 또는 치환 또는 비치환된 (5-30원)헤테로아릴이거나, 인접한 치환체와 연결되어 (3-30원) 단일환 또는 다환의 지환족 또는 방향족 고리를 형성할 수 있고, 상기 형성된 지환족 또는 방향족 환의 탄소 원자는 질소, 산소 및 황으로부터 선택되는 하나 이상의 헤테로원자로 대체될 수 있으며;
m 및 n은 각각 독립적으로 1 내지 4의 정수이며, 2 이상의 정수인 경우 각각의 R4 및 각각의 R5는 동일하거나 상이할 수 있고;
상기 헤테로아릴(렌)은 B, N, O, S, P(=O), Si 및 P로부터 선택된 하나 이상의 헤테로원자를 포함한다.An organic electroluminescent compound represented by the following Formula 1:
[Chemical Formula 1]
Figure pat00061

In Formula 1,
X is -O-, -S-, -CR 1 R 2 -or -NR 3- ,
L 1 is substituted or unsubstituted (5- to 30-membered) heteroarylene, or substituted or unsubstituted (C6-C30) arylene;
Ar 1 to Ar 4 are each independently substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C30) arylene, substituted or unsubstituted (5- to 30-membered) heteroaryl, or substituted Or unsubstituted (5- to 30-membered) heteroarylene;
Ar 1 and Ar 2 or Ar 3 and L 1 may form a nitrogen containing (5- to 30-membered) heteroaryl together with the nitrogen to which they are bound;
R 1 to R 3 Are each independently substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted 5-30 membered heteroaryl, or (3-30 with adjacent substituents) Raw) monocyclic or polycyclic alicyclic or aromatic rings;
R 4 and R 5 are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl , Substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (3- to 7-membered) Heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (5- to 30-membered) heteroaryl, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , -COR 18 or -B (OR 19 ) (OR 20 );
R 11 to R 20 are each independently hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxy, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, Substituted or unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C3-C30) cycloal Kenyl, substituted or unsubstituted (3-7 membered) heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5- to 30-membered) heteroaryl, or linked to an adjacent substituent (3-30 member) to form a monocyclic or polycyclic alicyclic or aromatic ring, 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;
m and n are each independently integers of 1 to 4, and when integers of 2 or more, each of R 4 and each R 5 may be the same or different;
The heteroaryl comprises at least one heteroatom selected from B, N, O, S, P (= O), Si and P. 제1항에 있어서,
X가 -O-, -S-, -CR1R2- 또는 -NR3-이고;
L1이 치환 또는 비치환된 (C6-C30)아릴렌이고;
Ar1 내지 Ar4가 각각 독립적으로 치환 또는 비치환된 (C6-C15)아릴, 치환 또는 비치환된 (C6-C15)아릴렌, 치환 또는 비치환된 (5-15원) 헤테로아릴, 또는 치환 또는 비치환된 (5-15원) 헤테로아릴렌이거나, Ar1과 Ar2 또는 Ar3와 L1은 결합하고 있는 질소와 함께 질소 함유 (5-15원)헤테로아릴을 형성할 수 있고;
R1 내지 R3 이 각각 독립적으로 치환 또는 비치환된 (C1-C15)알킬, 치환 또는 비치환된 (C6-C15)아릴, 또는 치환 또는 비치환된 (5-15원)헤테로아릴이고;
R4 및 R5가 각각 독립적으로 수소, 할로겐, 치환 또는 비치환된 (C1-C10)알킬, 치환 또는 비치환된 (C6-C15)아릴, 치환 또는 비치환된 (5-15원) 헤테로아릴 또는 -SiR13R14R15이고;
R13 내지 R15가 각각 독립적으로 치환 또는 비치환된 (C1-C10)알킬인 것을 특징으로 하는 유기 전계 발광 화합물.The method of claim 1,
X is -O-, -S-, -CR 1 R 2 -or -NR 3- ;
L 1 is substituted or unsubstituted (C6-C30) arylene;
Ar 1 to Ar 4 are each independently substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted (C6-C15) arylene, substituted or unsubstituted (5- to 15-membered) heteroaryl, or substituted Or unsubstituted (5- to 15-membered) heteroarylene, or Ar 1 and Ar 2 or Ar 3 and L 1 may form a nitrogen-containing (5- to 15-membered) heteroaryl together with the nitrogen to which it is bound;
R 1 to R 3 Each independently represent substituted or unsubstituted (C1-C15) alkyl, substituted or unsubstituted (C6-C15) aryl, or substituted or unsubstituted (5- to 15-membered) heteroaryl;
R 4 and R 5 are each independently hydrogen, halogen, substituted or unsubstituted (C1-C10) alkyl, substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted (5- to 15-membered) heteroaryl Or -SiR 13 R 14 R 15 ;
An organic electroluminescent compound, wherein R 13 to R 15 are each independently substituted or unsubstituted (C1-C10) alkyl. 제1항에 있어서,
X가 -O-, -S-, -CR1R2- 또는 -NR3-이고;
L1이 치환 또는 비치환된 (C6-C15)아릴렌이고;
Ar1 내지 Ar4가 각각 독립적으로 비치환된 (C6-C15)아릴, 비치환된 (C6-C15)아릴렌, 치환 또는 비치환된 (5-15원)헤테로아릴, 또는 치환 또는 비치환된 (5-15원)헤테로아릴렌이거나, Ar1과 Ar2 또는 Ar3와 L1은 결합하고 있는 질소와 함께 질소 함유 (5-15원)헤테로아릴을 형성할 수 있고;
R1 및 R2가 각각 독립적으로 치환 또는 비치환된 (C1-C10)알킬, 또는 치환 또는 비치환된 (C6-C15)아릴이고;
R3이 치환 또는 비치환된 (C6-C15)아릴이고;
R4 및 R5가 각각 독립적으로 수소, 비치환된 (C1-C10)알킬 또는 -SiR13R14R15이고;
R13 내지 R15가 각각 독립적으로 치환 또는 비치환된 (C1-C10)알킬인 것을 특징으로 하는 유기 전계 발광 화합물.The method of claim 1,
X is -O-, -S-, -CR 1 R 2 -or -NR 3- ;
L 1 is substituted or unsubstituted (C6-C15) arylene;
Ar 1 to Ar 4 are each independently unsubstituted (C6-C15) aryl, unsubstituted (C6-C15) arylene, substituted or unsubstituted (5- to 15-membered) heteroaryl, or substituted or unsubstituted (5-15 membered) heteroarylene, or Ar 1 and Ar 2 or Ar 3 and L 1 together with the nitrogen to which they are bound may form a nitrogen containing (5-15 membered) heteroaryl;
R 1 and R 2 are each independently substituted or unsubstituted (C1-C10) alkyl, or substituted or unsubstituted (C6-C15) aryl;
R 3 is substituted or unsubstituted (C6-C15) aryl;
R 4 and R 5 are each independently hydrogen, unsubstituted (C1-C10) alkyl or -SiR 13 R 14 R 15 ;
An organic electroluminescent compound, wherein R 13 to R 15 are each independently substituted or unsubstituted (C1-C10) alkyl. 제1항에 있어서,
상기 L1 , Ar1 내지 Ar4 , R1 내지 R5 , 및 R11 내지 R20 에서 치환 알킬, 치환 알케닐, 치환 알키닐, 치환 알콕시, 치환 시클로알킬, 치환 시클로알케닐, 치환 헤테로시클로알킬, 치환 아릴(렌) 및 치환 헤테로아릴(렌)의 치환체는 서로 독립적으로 중수소, 할로겐, 시아노, 카르복실, 니트로, 히드록시, (C1-C30)알킬, 할로(C1-C30)알킬, (C2-C30)알케닐, (C2-C30)알키닐, (C1-C30)알콕시, (C1-C30)알킬티오, (C3-C30)시클로알킬, (C3-C30)시클로알케닐, (3-7원) 헤테로시클로알킬, (C6-C30)아릴옥시, (C6-C30)아릴티오, (C6-C30)아릴로 치환되거나 비치환된 (5-30원)헤테로아릴, (5-30원)헤테로아릴로 치환되거나 비치환된 (C6-C30)아릴, 트리(C1-C30)알킬실릴, 트리(C6-C30)아릴실릴, 디(C1-C30)알킬(C6-C30)아릴실릴, (C1-C30)알킬디(C6-C30)아릴실릴, 아미노, 모노 또는 디(C1-C30)알킬아미노, 모노 또는 디(C6-C30)아릴아미노, (C1-C30)알킬(C6-C30)아릴아미노, (C6-C30)아릴(5-30원)헤테로아릴아미노, (C1-C30)알킬카보닐, (C1-C30)알콕시카보닐, (C6-C30)아릴카보닐, 디(C6-C30)아릴보로닐, 디(C1-C30)알킬보로닐, (C1-C30)알킬(C6-C30)아릴보로닐, (C6-C30)아르(C1-C30)알킬 및 (C1-C30)알킬(C6-C30)아릴로 이루어진 군으로부터 선택되는 1종 이상인 것을 특징으로 하는 유기 전계 발광 화합물.The method of claim 1,
Substituted alkyl, substituted alkenyl, substituted alkynyl, substituted alkoxy, substituted cycloalkyl, substituted cycloalkenyl, substituted heterocycloalkyl at L 1 , Ar 1 to Ar 4 , R 1 to R 5 , and R 11 to R 20 , Substituents of substituted aryl (ene) and substituted heteroaryl (ene) are independently of each other deuterium, halogen, cyano, carboxyl, nitro, hydroxy, (C1-C30) alkyl, halo (C1-C30) alkyl, ( C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cycloalkyl, (C3-C30) cycloalkenyl, (3- 7-membered) (5- to 30-membered) heteroaryl unsubstituted or substituted with heterocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, (C6-C30) aryl (C6-C30) aryl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, unsubstituted or substituted with heteroaryl, (C1) -C30) alkyldi (C6-C30) arylsilyl, amino, mono or di (C1-C30) alkylamino, mono or di (C6-C30) Arylamino, (C1-C30) alkyl (C6-C30) arylamino, (C6-C30) aryl (5--30membered) heteroarylamino, (C1-C30) alkylcarbonyl, (C1-C30) alkoxycarbonyl , (C6-C30) arylcarbonyl, di (C6-C30) arylboronyl, di (C1-C30) alkylboronyl, (C1-C30) alkyl (C6-C30) arylboronyl, (C6 -C30) at least one member selected from the group consisting of ar (C1-C30) alkyl and (C1-C30) alkyl (C6-C30) aryl. 제1항에 있어서, 상기 화학식 1로 표시되는 화합물이 하기 화합물로부터 선택되는 유기 전계 발광 화합물.
Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

Figure pat00067

Figure pat00068

Figure pat00069

Figure pat00070

Figure pat00071

Figure pat00072

Figure pat00073

Figure pat00074

Figure pat00075

Figure pat00076

Figure pat00077

Figure pat00078

Figure pat00079

Figure pat00080

Figure pat00081

Figure pat00082

Figure pat00083

Figure pat00084
The organic electroluminescent compound according to claim 1, wherein the compound represented by Formula 1 is selected from the following compounds.
Figure pat00062

Figure pat00063

Figure pat00064

Figure pat00065

Figure pat00066

Figure pat00067

Figure pat00068

Figure pat00069

Figure pat00070

Figure pat00071

Figure pat00072

Figure pat00073

Figure pat00074

Figure pat00075

Figure pat00076

Figure pat00077

Figure pat00078

Figure pat00079

Figure pat00080

Figure pat00081

Figure pat00082

Figure pat00083

Figure pat00084
 제1항의 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.An organic electroluminescent device comprising the compound of claim 1.
KR1020120109953A 2012-10-04 2012-10-04 Novel organic electroluminescence compounds and organic electroluminescence device containing the same KR20140044043A (en)

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