KR101618409B1 - Organic compounds and organic electro luminescence device comprising the same - Google Patents

Organic compounds and organic electro luminescence device comprising the same Download PDF

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KR101618409B1
KR101618409B1 KR1020130120465A KR20130120465A KR101618409B1 KR 101618409 B1 KR101618409 B1 KR 101618409B1 KR 1020130120465 A KR1020130120465 A KR 1020130120465A KR 20130120465 A KR20130120465 A KR 20130120465A KR 101618409 B1 KR101618409 B1 KR 101618409B1
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KR20150042335A (en
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김태형
이용환
이인혁
김은진
백영미
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주식회사 두산
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Abstract

본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층에 사용됨에 따라 유기 전계 발광 소자의 발광효율, 구동 전압, 수명 등을 향상시킬 수 있다.The present invention relates to a novel compound and an organic electroluminescent device including the same, and the compound according to the present invention is used for an organic compound layer, preferably a light emitting layer, of an organic electroluminescent device, And the like can be improved.

Description

유기 화합물 및 이를 포함하는 유기 전계 발광 소자{ORGANIC COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE COMPRISING THE SAME}TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device including the organic compound.

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

유기 전계 발광 소자에서는 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic layer in the anode, and electrons are injected into the organic layer in the cathode. When the injected holes and electrons meet, an exciton is formed. When the exciton falls to the ground state, light is emitted. At this time, the material used as the organic material layer can be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material and the like depending on its function.

상기 발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다.The luminescent material may be classified into blue, green and red luminescent materials according to luminescent colors and yellow and orange luminescent materials necessary to realize better natural colors. Further, in order to increase the color purity and to increase the luminous efficiency through energy transfer, a host / dopant system can be used as a luminescent material.

도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 이때, 인광 도판트는 이론적으로 형광 도판트에 비해 최대 4배의 발광 효율을 향상시킬 수 있기 때문에 인광 도판트 뿐만 아니라 인광 호스트에 대한 연구가 많이 진행되고 있다.The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since the phosphorescent dopant can theoretically improve the luminous efficiency up to 4 times as compared with the fluorescent dopant, studies on the phosphorescent dopant as well as the phosphorescent host have been conducted.

현재 발광층에 사용되는 형광 도판트/호스트 물질로는 안트라센 유도체들이 알려져 있다. 또한 발광층에 사용되는 인광 도판트 물질로는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등의 Ir을 포함하는 금속 착체 화합물이 알려져 있고, 인광 호스트 물질로는 4,4-dicarbazolybiphenyl(CBP)가 알려져 있다.Currently, anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer. As phosphorescent dopant materials used for the light emitting layer, metal complex compounds including Ir such as Firpic, Ir (ppy) 3 , (acac) Ir (btp) 2 and the like are known. As phosphorescent host materials, 4,4-dicarbazolybiphenyl (CBP) is known.

그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 떨어지기 때문에 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다.However, existing materials have advantages in terms of luminescent properties, but their thermal stability is poor due to their low glass transition temperature, which is not satisfactory in terms of lifetime of an organic electroluminescent device.

상기한 문제점을 해결하기 위해 본 발명은 유리전이온도가 높고, 열적 안정성이 우수하며, 정공과 전자의 결합력을 향상시킬 수 있는 신규 유기 화합물을 제공하는 것을 목적으로 한다.In order to solve the above problems, it is an object of the present invention to provide a novel organic compound which has a high glass transition temperature, is excellent in thermal stability and can improve the bonding force between holes and electrons.

또 본 발명은 상기 유기 화합물을 포함하여 구동전압, 발광효율 등이 향상된 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device including the organic compound and having improved driving voltage, luminescent efficiency and the like.

상기한 목적을 달성하기 위해 본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.In order to accomplish the above object, the present invention provides a compound represented by the following general formula (1).

[화학식 1][Chemical Formula 1]

Figure 112013091458803-pat00001
Figure 112013091458803-pat00001

상기 화학식 1에서,In Formula 1,

L1 및 L2는 단일결합, 치환 또는 비치환된 C6~C18의 아릴렌기이거나, 치환 또는 비치환된 핵원자수 5 내지 18의 헤테로아릴렌기이고,L 1 and L 2 are a single bond, a substituted or unsubstituted C 6 -C 18 arylene group, a substituted or unsubstituted heteroarylene group having 5 to 18 nucleus atoms,

X1 내지 X3는 각각 독립적으로 N 또는 C(R11)이고, 이때, 적어도 하나 이상은 N이며,X 1 to X 3 are each independently N or C (R 11 ), wherein at least one is N,

R1 내지 R4, R11 및 Ar1은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,R 1 to R 4 , R 11 and Ar 1 are each independently hydrogen, deuterium, halogen, cyano, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, A C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 40 arylamine group, A C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 40 arylboron group, A C 6 to C 40 arylphosphine group, a C 6 to C 40 arylphosphine oxide group, and a C 6 to C 40 arylsilyl group,

R1 내지 R4는 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며,R 1 to R 4 may combine with adjacent groups to form a condensed ring,

상기 R1 내지 R4, R11 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상으로 치환될 수 있으며, 이때, 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이하고,The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group and alkylsilyl group of R 1 to R 4 , R 11 and Ar 1 , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of, C A C 3 to C 40 cycloalkyl group, a C 3 to C 40 heterocycloalkyl group, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 40 arylamine group, a C 3 to C 40 cycloalkyl group, value to 6 ~ C 40 aryl group of boron, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide groups and at least one member selected from the group consisting of C 6 ~ C 40 aryl group in the silyl It may be, at this time, and if these are substituted by multiple substituents, same or different from each other,

m 및 n은 각각 독립적으로 0 내지 4의 정수이다.m and n are each independently an integer of 0 to 4;

본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1의 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device including a cathode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes one or more compounds represented by Formula 1 .

여기서 상기 화학식 1의 화합물을 포함하는 유기물층은 인광발광층일 수 있다.Here, the organic compound layer including the compound of Formula 1 may be a phosphorescent light-emitting layer.

본 발명에서의 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다.In the present invention, alkyl is a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, However, the present invention is not limited thereto.

본 발명에서의 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다.The alkenyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include vinyl, allyl, Isopropenyl, 2-butenyl, and the like, but the present invention is not limited thereto.

본 발명에서의 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다.Alkynyl in the present invention is a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include ethynyl, 2- 2-propynyl, and the like, but are not limited thereto.

본 발명에서의 아릴은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등이 있는데, 이에 한정되지 않는다.The aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

본 발명에서의 헤테로아릴은 핵원자수 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함하는 것으로 해석한다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다.The heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. In addition, it is understood that a form in which two or more rings are pendant or condensed with each other may be included, and further includes a condensed form with an aryl group. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; Imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

본 발명에서의 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, aryloxy is a monovalent substituent represented by RO-, and R represents aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.

본 발명에서의 알킬옥시는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.The alkyloxy in the present invention is a monovalent substituent group represented by R'O-, wherein R 'represents 1 to 40 alkyl, and includes a linear, branched or cyclic structure. . Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

본 발명에서의 아릴아민은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.The arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

본 발명에서의 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.The cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

본 발명에서의 헤테로시클로알킬은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다.Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon of the ring, preferably 1 to 3 carbons, is N, O, S or Se. ≪ / RTI > Examples of such heterocycloalkyls include, but are not limited to, morpholine, piperazine, and the like.

본 발명에서의 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 40의 아릴로 치환된 실릴을 의미한다.The alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.

본 발명에서의 축합 고리는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.The condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.

본 발명에 따른 화학식 1로 표시되는 화합물은 열적 안정성 및 인광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명에 따른 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우 종래의 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 가지는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능, 수명이 크게 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound represented by the formula (1) according to the present invention has excellent thermal stability and phosphorescence properties and can be used as a material of an organic material layer of an organic electroluminescent device. In particular, when the compound represented by Formula 1 according to the present invention is used as a phosphorescent host material, it is possible to produce an organic electroluminescent device having excellent light emitting performance, low driving voltage, high efficiency and long life time as compared with conventional host materials, A full-color display panel having greatly improved performance and lifetime can be manufactured.

이하, 본 발명을 상세히 설명한다.
Hereinafter, the present invention will be described in detail.

1. 신규 유기 화합물1. New organic compounds

본 발명에 따른 신규 화합물은 디벤조퓨란(dibenzo[b,d]furan), 6원 헤테로환, 인돌 모이어티(indole moiety)가 결합하여 기본 골격을 이루며, 이러한 기본 골격에 다양한 치환체가 결합된 구조로서 상기 화학식 1로 표시되는 것을 특징으로 한다.The novel compound according to the present invention has a basic structure in which dibenzo [b, d] furan, a 6-membered heterocycle, and an indole moiety are bonded to form a basic skeleton. Is represented by the formula (1).

디벤조퓨란(dibenzo[b,d]furan)은 삼중항 에너지가 크고 전기화학적으로 안정하다. 이러한 디벤조퓨란(dibenzo[b,d]furan)에 전자끄는기(electron withdrawing group, EWG)인 6원 함질소 헤테로환(예를 들어, 피리딘, 피리미딘, 트리아진)과, 전자주는기(electron donating group, EDG)인 인돌 모이어티(indole moiety)가 결합된 본 발명의 화학식 1로 표시되는 화합물은 전자 흡수성이 큰 전자끄는기(electron withdrawing group, EWG)와 전자 공여성이 큰 전자주는기(electron donating group, EDG)를 모두 가져 분자 전체가 바이폴라(bipolar) 특성을 나타내 정공과 전자의 결합력이 높기 때문에 인광 발광층에서 호스트로서 유리할 뿐만 아니라, 정공 수송층, 정공 주입층에도 적용될 수 있다.Dibenzo [b, d] furan has a high triplet energy and is electrochemically stable. This dibenzo [b, d] furan has an electron withdrawing group (EWG), a six-membered nitrogen heterocycle (for example, pyridine, pyrimidine and triazine) (EWG) having a large electron absorbing property and a large electron donating group (EWG) having an indole moiety, which is an electron donating group (EDG) (EDG), the whole molecule exhibits a bipolar characteristic and is highly advantageous as a host in a phosphorescent light emitting layer because of its high bonding strength with holes and electrons, and can also be applied to a hole transport layer and a hole injection layer.

또한 본 발명의 화학식 1로 표시되는 화합물은 방향족 환(aromatic ring) 또는 헤테로방향족 환(heteroaromatic ring) 치환체로 인해 화합물의 분자량이 유의적으로 증대되어 유리전이온도가 향상됨에 따라 종래의 CBP(4,4-dicarbazolybiphenyl)보다 높은 열적 안정성을 나타낸다. 본 발명의 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에도 효과가 있다.In addition, since the compound represented by Formula 1 of the present invention has an aromatic ring or a heteroaromatic ring substituent, the molecular weight of the compound is significantly increased and the glass transition temperature is improved, 4-dicarbazolybiphenyl). The compound represented by the general formula (1) of the present invention is also effective for inhibiting crystallization of the organic material layer.

따라서 본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 정공 주입층, 정공 수송층 또는 발광층의 재료로 사용할 경우, 종래의 유기물층 재료(예를 들어, CBP)에 비해 유기 전계 발광 소자의 효율 및 수명을 향상시킬 수 있다. 또한 이러한 유기 전계 발광 소자 수명 향상은 풀 칼라 유기 발광 패널의 성능을 극대화시킬 수 있다.Therefore, when the compound represented by the formula (1) of the present invention is used as a material for the hole injection layer, the hole transporting layer or the light emitting layer of an organic electroluminescent device, the efficiency and the efficiency of the organic electroluminescent device The life can be improved. Further, the lifetime of the organic electroluminescent device can be maximized by maximizing the performance of the full-color organic electroluminescent panel.

본 발명의 화학식 1로 표시되는 화합물에서, 상기 L1 및 L2는 2가(divalent) 그룹의 연결기(linker)로서 단일결합, 치환 또는 비치환된 C6~C40의 아릴렌기 또는, 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴렌기이다.In the compound represented by the formula (1) of the present invention, L 1 and L 2 are a divalent group linker, a single bond, a substituted or unsubstituted C 6 -C 40 arylene group, And a heteroarylene group having 5 to 40 unsubstituted nuclear atoms.

상기 C6~C40의 아릴렌기와, 핵원자수 5 내지 40의 헤테로아릴렌기는 특별히 한정되지 않으나, 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 트리아졸릴렌기, 피리디닐렌기, 피리미디닐렌기 등을 들 수 있다.The C 6 -C 40 arylene group and the heteroarylene group having 5 to 40 nucleus atoms are not particularly limited, but a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, an indenylene group, a pyranthrenylene group , A carbazolyl group, a thiophenylene group, an indolylene group, a prolinylene group, a quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, Nylene group and the like.

구체적으로, 상기 L1 및 L2는 각각 독립적으로 단일결합, 페닐렌기, 또는 비페닐렌기인 것이 바람직하다.Specifically, it is preferable that L 1 and L 2 each independently represent a single bond, a phenylene group, or a biphenylene group.

본 발명의 화학식 1로 표시되는 화합물에서, 상기 X1 내지 X3는 각각 독립적으로 N 또는 C(R11)이며, 적어도 하나 이상은 N을 포함하는데, X1 내지 X3가 모두 N인 것이 바람직하다. 또한 X1 내지 X3 중 둘 이상이 C(R11)인 경우, 복수 개의 R11은 서로 동일하거나 상이하며, R11은 수소인 것이 바람직하다.In the compound represented by formula (1) of the present invention, each of X 1 to X 3 is independently N or C (R 11 ), and at least one of them includes N, and X 1 to X 3 are all preferably N Do. When two or more of X 1 to X 3 are C (R 11 ), a plurality of R 11 s are the same as or different from each other, and R 11 is preferably hydrogen.

본 발명의 화학식 1로 표시되는 화합물에서, 상기 R1 및 R2는 서로 결합하여 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리를 형성할 수 있다. 구체적으로 R1 및 R2는 서로 결합하여 벤젠, 나프탈렌, 인돌, 플루오렌, 카바졸을 형성하는 것이 바람직하다.In the compound represented by formula (1) of the present invention, R 1 and R 2 may be bonded to each other to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, and a condensed heteroaromatic ring. Specifically, R 1 and R 2 are preferably bonded to each other to form benzene, naphthalene, indole, fluorene, or carbazole.

본 발명의 화학식 1로 표시되는 화합물에서, 상기 R3 및 R4는 각각 독립적으로 수소, C6~C40의 아릴기 또는, 핵원자수 5 내지 40의 헤테로아릴기인 것이 바람직하다.In the compound represented by the general formula (1) of the present invention, it is preferable that each of R 3 and R 4 is independently hydrogen, a C 6 to C 40 aryl group, or a heteroaryl group having 5 to 40 nuclear atoms.

특히, R3는 수소, 페닐기, 나프틸기, 플루오렌기, 카바졸기, 디벤조싸이오펜기, 디벤조퓨란기, 디벤조셀레노펜기, 디벤조실롤기로 이루어진 군에서 선택되는 것이 더욱 바람직하다.Particularly, it is more preferable that R 3 is selected from the group consisting of hydrogen, a phenyl group, a naphthyl group, a fluorene group, a carbazole group, a dibenzothiophene group, a dibenzofurane group, a dibenzoselenophene group and a dibenzosilyl group.

본 발명의 화학식 1로 표시되는 화합물에서, 상기 Ar1은 수소, C6~C40의 아릴기 또는, 핵원자수 5 내지 40의 헤테로아릴기인 것이 바람직하다.In the compound represented by the general formula (1) of the present invention, Ar 1 is preferably hydrogen, a C 6 to C 40 aryl group, or a heteroaryl group having 5 to 40 nuclear atoms.

상기 R1 내지 R4, R11 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 이때 복수개의 치환기로 치환될 경우 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group and alkylsilyl group of R 1 to R 4 , R 11 and Ar 1 , An alkylboron group, an arylboron group, an arylphosphine group, an arylphosphine oxide group and an arylsilyl group are each independently selected from the group consisting of deuterium, a halogen, a cyano group, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, an aryloxy group of nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 ~ C 40, alkyloxy group of C 1 ~ C 40 of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C group 1 ~ C 40 alkyl silyl, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 aryl group of boron, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ 1 or more substituents selected from the group consisting of C 40 aryl silyl And when they are substituted with a plurality of substituents, they may be the same or different from each other.

이러한 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 2 내지 10으로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하다.The compound represented by the formula (1) of the present invention is preferably selected from the group consisting of compounds represented by the following formulas (2) to (10).

[화학식 2](2)

Figure 112013091458803-pat00002
Figure 112013091458803-pat00002

[화학식 3](3)

Figure 112013091458803-pat00003
Figure 112013091458803-pat00003

[화학식 4][Chemical Formula 4]

Figure 112013091458803-pat00004
Figure 112013091458803-pat00004

[화학식 5][Chemical Formula 5]

Figure 112013091458803-pat00005
Figure 112013091458803-pat00005

[화학식 6][Chemical Formula 6]

Figure 112013091458803-pat00006
Figure 112013091458803-pat00006

[화학식 7](7)

Figure 112013091458803-pat00007
Figure 112013091458803-pat00007

[화학식 8][Chemical Formula 8]

Figure 112013091458803-pat00008
Figure 112013091458803-pat00008

[화학식 9][Chemical Formula 9]

Figure 112013091458803-pat00009
Figure 112013091458803-pat00009

[화학식 10][Chemical formula 10]

Figure 112013091458803-pat00010
Figure 112013091458803-pat00010

상기 화학식 2 내지 10에서, X1 내지 X3, L1, L2, R1 내지 R4, Ar1, m 및 n 은 상기 화학식 1에서의 정의한 바와 동일하고,Wherein X 1 to X 3 , L 1 , L 2 , R 1 to R 4 , Ar 1 , m and n are the same as defined in Formula 1,

Y1은 N(R12), O, S, Se, C(R13)(R14), Si(R15) (R16)로 이루어진 군에서 선택되며,Y 1 is selected from the group consisting of N (R 12), O, S, Se, C (R 13) (R 14), Si (R 15) (R 16),

R5, R6 및 R12 내지 R16은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,R 5 , R 6 and R 12 To R 16 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, C 6 to C 40 aryl , A heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 40 arylamine group, a C 3 to C 40 cycloalkyl group , A heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 40 arylboron group, a C 6 to C 40 arylphosphine is selected from the pingi, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 of the group consisting of aryl silyl,

상기 R5 , R6, R12 내지 R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상으로 치환될 수 있으며, l는 0 내지 4의 정수이다.R 5 , R 6 , R 12 An alkyl group of 1 to R 16, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, The arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently selected from the group consisting of deuterium, halogen, cyano group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, A C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 40 arylamine group, A C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 40 arylboron group, C 6 to C 40 aryl phosphine groups, C 6 to C 40 aryl phosphine oxide groups, and C 6 to C 40 arylsilyl groups, and l is 0 Lt; / RTI >

이러한 본 발명의 화학식 1로 표시되는 화합물의 예로는 하기 화합물들(C-1 내지 C-129)을 들 수 있지만, 본 발명의 화학식 1로 표시되는 화합물이 하기 화합물들로 한정되는 것은 아니다.Examples of the compound represented by the formula (1) of the present invention include the following compounds (C-1 to C-129), but the compound represented by the formula (1) of the present invention is not limited to the following compounds.

Figure 112013091458803-pat00011
Figure 112013091458803-pat00011

Figure 112013091458803-pat00012
Figure 112013091458803-pat00012

Figure 112013091458803-pat00013
Figure 112013091458803-pat00013

Figure 112013091458803-pat00014
Figure 112013091458803-pat00014

Figure 112013091458803-pat00015
Figure 112013091458803-pat00015

Figure 112013091458803-pat00016
Figure 112013091458803-pat00016

Figure 112013091458803-pat00017
Figure 112013091458803-pat00017

Figure 112013091458803-pat00018
Figure 112013091458803-pat00018

Figure 112013091458803-pat00019
Figure 112013091458803-pat00019

본 발명의 화학식 1로 표시되는 화합물은 하기 합성예를 참조하여 다양하게 합성할 수 있다.
The compounds represented by formula (1) of the present invention can be synthesized in various ways with reference to the following Synthesis Examples.

2. 유기 2. Organic 전계Field 발광 소자 Light emitting element

본 발명은 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다. 이때, 상기 화합물은 단독으로 사용되거나, 또는 2 이상이 혼합되어 사용될 수 있다.The present invention relates to an organic electroluminescent device comprising at least an anode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by Formula 1 An organic electroluminescent device is provided. At this time, the compounds may be used alone or in combination of two or more.

상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있다. 여기서 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.The one or more organic material layers may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Here, the organic compound layer including the compound represented by Formula 1 is preferably a light emitting layer.

본 발명의 유기 전계 발광 소자의 발광층은 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층 재료, 바람직하게는 청색, 녹색, 적색의 인광 호스트 재료로 포함할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 구체적으로 상기 화학식 1로 표시되는 화합물은 녹색 및/또는 적색의 인광 호스트, 형광 호스트, 또는 도펀트 재료로서 유기 전계 발광 소자에 포함되는 것이 바람직하다.The light emitting layer of the organic electroluminescent device of the present invention may include a host material, wherein the host material may include a compound represented by the above formula (1). When the compound represented by Formula 1 is contained as a light emitting layer material of an organic electroluminescent device, preferably a blue, green, or red phosphorescent host material, the bonding strength between holes and electrons in the light emitting layer is increased. (Luminous efficiency and power efficiency), lifetime, luminance, driving voltage and the like can be improved. Specifically, the compound represented by Formula 1 is preferably included in the organic electroluminescent device as a green and / or red phosphorescent host, a fluorescent host, or a dopant material.

본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있다. 상기 전자 수송층 위에는 전자 주입층이 추가로 적층될 수 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. An electron injection layer may be further stacked on the electron transport layer.

또한 본 발명의 유기 전계 발광 소자의 구조는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.Further, the structure of the organic electroluminescent device of the present invention may be a structure in which an anode, one or more organic material layers and a cathode are sequentially laminated, and an insulating layer or an adhesive layer is inserted into the interface between the electrode and the organic material layer.

본 발명의 유기 전계 발광 소자는 상기 유기물층 중 1층 이상 (예컨대, 발광층)이 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당업계에 공지된 재료 및 방법을 이용하여 다른 유기물층 및 전극을 형성하여 제조될 수 있다.The organic electroluminescent device of the present invention may be formed by using materials and methods known in the art, except that at least one of the organic layers (for example, the light emitting layer) includes the compound represented by the above formula (1) And electrodes.

상기 유기물층은 진공 증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

본 발명의 유기 전계 발광 소자에 포함되는 기판으로는 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다.As the substrate included in the organic electroluminescent device of the present invention, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

또 양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등이 사용될 수 있다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black may be used.

또한 음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 사용될 수 있다.The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof and a multilayer such as LiF / Al or LiO 2 / Structural materials and the like can be used.

또 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며, 당 업계에 알려진 통상의 물질이 사용될 수 있다.
The hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer are not particularly limited, and ordinary materials known in the art can be used.

이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐, 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.
Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[[ 준비예Preparation Example 1]  One] ICIC -1의 합성Synthesis of -1

Figure 112013091458803-pat00020
Figure 112013091458803-pat00020

50 ml의 anhydrous tetrahydrofuran 용매에 magnesium (14.5 g, 598 mmol), iodine (3.0 g, 12 mmol)를 녹인 후, anhydrous tetrahydrofuran 130 ml에 4-bromodibenzo[b,d]furan (147.7 g, 598 mmol)를 녹인 용액을 30분간 한 방울 씩 첨가한다. 이 혼합물을 80?에서 2시간 동안 교반한 후 상온에서 식힌다. 그 후, anhydrous tetrahydrofuran 390 ml에 녹인 1,3,5-trichlorotriazine (110.3 g, 598 mmol) 용액을 3시간 동안 교반시키면서 한 방울씩 첨가한다.After dissolving magnesium (14.5 g, 598 mmol) and iodine (3.0 g, 12 mmol) in 50 ml of anhydrous tetrahydrofuran solvent, 4-bromodibenzo [b, d] furan (147.7 g, 598 mmol) was added to 130 ml of anhydrous tetrahydrofuran Add the dissolved solution for 30 minutes. The mixture is stirred at 80 ° C for 2 hours and then cooled at room temperature. Then, 1,3,5-trichlorotriazine (110.3 g, 598 mmol) dissolved in 390 ml of anhydrous tetrahydrofuran is added dropwise with stirring for 3 hours.

반응이 종결된 후, 감압 증류하여 유기 용매를 제거하고 컬럼크로마토그래피로 정제한 후 methanol로 재결정을 실시하여 얻어낸 결정을 여과하여 IC-1 (40.89 g, 수율 65%)을 얻었다.After the reaction was completed, the organic solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography. Recrystallization was performed with methanol, and the obtained crystals were filtered to obtain IC-1 (40.89 g, yield 65%).

1H-NMR: δ 7.32 (m, 3H), 7.66 (d, 1H), 7.85 (m, 3H)
 1 H-NMR: δ 7.32 ( m, 3H), 7.66 (d, 1H), 7.85 (m, 3H)

[[ 준비예Preparation Example 2]  2] ICIC -2의 합성Synthesis of -2

Figure 112013091458803-pat00021
Figure 112013091458803-pat00021

준비예 1에서 사용된 4-bromodibenzo[b,d]furan 대신 2-bromodibenzo[b,d]furan (147.7 g, 598 mmol)를 사용하는 것을 제외하고는 상기 준비예 1과 동일한 과정을 수행하여 IC-2를 얻었다.The procedure of Preparation Example 1 was repeated except that 2-bromodibenzo [b, d] furan (147.7 g, 598 mmol) was used instead of 4-bromodibenzo [b, -2.

1H-NMR: δ 7.35 (m, 2H), 7.70 (m, 3H), 7.85 (m, 2H)
 1 H-NMR: δ 7.35 ( m, 2H), 7.70 (m, 3H), 7.85 (m, 2H)

[[ 준비예Preparation Example 3]  3] ICIC -3의 합성Synthesis of -3

Figure 112013091458803-pat00022
Figure 112013091458803-pat00022

질소 기류 하에서 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (2.59 g, 7.03 mmol)과 3-bromo-9H-carbazole (2.07 g, 8.43 mmol), NaOH (0.84 g, 21.08 mmol) 및 THF/H2O (40 ml/20 ml)를 혼합한 다음, 40?에서 Pd(PPh3)4 (0.48 g, 5 mol%)를 넣고 80?에서 12시간 동안 교반하였다.9H-carbazole (2.59 g, 7.03 mmol) and 3-bromo-9H-pyrazole-3-carbaldehyde carbazole (2.07 g, 8.43 mmol) , NaOH (0.84 g, 21.08 mmol) and THF / H 2 O (40 ml / 20 ml) , and then, Pd (PPh 3) 4 ( 0.48 g in 40?, 5 mol mixing %), And the mixture was stirred at 80? For 12 hours.

반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:MC = 3:1 (v/v))로 정제하여 IC-3 (2.15 g, 수율 75%)을 얻었다.After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO 4 and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-3 (2.15 g, yield 75%).

1H-NMR: δ 7.29 (m, 3H), 7.55 (m, 11H), 7.88 (m, 3H), 8.12 (d, 1H), 8.53 (d, 1H), 10.33 (s, 1H)
 1 H-NMR:? 7.29 (m, 3H), 7.55 (m, 11H), 7.88 (m, 3H), 8.12

[[ 준비예Preparation Example 4]  4] ICIC -4의 합성Synthesis of -4

Figure 112013091458803-pat00023
Figure 112013091458803-pat00023

질소 기류 하에서 상기 준비예 3에서 얻은 IC-3 (18.85 g, 46.17 mmol), 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol), K2CO3 (6.38 g, 46.17 mmol), nitrobenzene (200 ml)를 혼합하고 190?에서 12시간 동안 교반하였다.(18.85 g, 46.17 mmol), 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol), Cu powder (0.29 g, 4.62 mmol) and K 2 CO 3 6.38 g, 46.17 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190? For 12 hours.

반응 종결 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리하여 MgSO4를 사용하여 물을 제거하였다. 물이 제거된 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:MC = 3:1 (v/v))로 정제하여 IC-4 (20.81 g, 수율 80%)를 얻었다.After completion of the reaction, the nitrobenzene was removed. The organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The solvent was removed from the organic layer from which water had been removed and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-4 (20.81 g, yield 80%).

1H-NMR: δ 7.30 (m, 5H), 7.60 (m, 12H), 7.91 (m, 4H), 8.51 (m, 2H)
 1 H-NMR: δ 7.30 ( m, 5H), 7.60 (m, 12H), 7.91 (m, 4H), 8.51 (m, 2H)

[[ 준비예Preparation Example 5]  5] ICIC -5의 합성Synthesis of -5

Figure 112013091458803-pat00024
Figure 112013091458803-pat00024

질소 기류 하에서 7-chloro-3-phenyl-3,10-dihydropyrrolo[3,2-a]carbazole (2.23 g, 7.03 mmol)과 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (3.11 g, 8.43 mmol), X-phos (0.33 g, 0.70 mmol), Cs2CO3 (4.58 g, 14.06 mmol) 및 Toluene/Ethanol/H2O (80 ml/20 ml/20 ml)를 혼합한 다음, Pd(OAc)2 (0.08 g, 5 mol%)를 넣고 110?에서 6시간 동안 교반하였다.3-phenyl-3,10-dihydropyrrolo [3,2-a] carbazole (2.23 g, 7.03 mmol) and 9-phenyl-3- (4,4,5,5-tetramethyl- , 3,2-dioxaborolan-2-yl ) -9H-carbazole (3.11 g, 8.43 mmol), X-phos (0.33 g, 0.70 mmol), Cs 2 CO 3 (4.58 g, 14.06 mmol) and Toluene / Ethanol / H 2 O (80 ml / 20 ml / 20 ml) was mixed and Pd (OAc) 2 (0.08 g, 5 mol%) was added thereto and stirred at 110? For 6 hours.

반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:MC = 3:1 (v/v))로 정제하여 IC-5 (2.21 g, 수율 60%)을 얻었다.After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was added with MgSO 4 and filtered. The solvent was removed from the obtained organic layer and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain IC-5 (2.21 g, yield 60%).

1H NMR: δ 6.52 (d, 1H), 7.30 (m, 2H), 7.54 (m, 15H), 7.94 (m, 5H), 8.55 (d, 1H), 10.33 (s, 1H)
 1 H NMR:? 6.52 (d, 1 H), 7.30 (m, 2H), 7.54 (m, 15H), 7.94

[[ 준비예Preparation Example 6]  6] ICIC -6의 합성Synthesis of -6

Figure 112013091458803-pat00025
Figure 112013091458803-pat00025

IC-3 대신 IC-5 (24.17 g, 46.17 mmol)를 사용하는 것을 제외하고는 준비예 4와 동일한 과정을 수행하여 IC-6을 얻었다.Except using IC-5 (24.17 g, 46.17 mmol) instead of IC-3 The same procedure as in Preparation Example 4 was carried out to obtain IC-6.

1H NMR: δ 6.52 (d, 1H), 7.30 (m, 3H), 7.58 (m, 14H), 7.69 (d, 1H), 7.77 (m, 2H), 7.98 (m, 5H), 8.18 (d, 1H), 8.57 (d, 1H)
 1 H NMR:? 6.52 (d, 1 H), 7.30 (m, 3H), 7.58 (m, 14H), 7.69 , ≪ / RTI > 1H), 8.57 (d, 1H)

[[ 준비예Preparation Example 7]  7] ICIC -7의 합성Synthesis of -7

Figure 112013091458803-pat00026
Figure 112013091458803-pat00026

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 2-(dibenzo[b,d]thiophen-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.18 g, 7.03 mmol)를 사용하고, 3-bromo-9H-carbazole 대신 8-bromo-11H-benzo[a]carbazole (2.50 g, 8.43 mmol)을 사용하는 것을 제외하고는 준비예 3과 동일한 과정을 수행하여 IC-7을 얻었다.(Dibenzo [b, d] thiophen-4-yl) - 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2- dioxaborolan- Bromo-11H-benzo [a] carbazole (2.50 g, 7.03 mmol) was used instead of 3-bromo-9H- , 8.43 mmol), IC-7 was obtained.

1H-NMR: δ 7.57 (m, 7H), 7.77 (s, 1H), 7.87 (d, 1H), 7.98 (d, 1H), 8.16 (m, 3H), 8.45 (m, 3H), 10.24 (s, 1H)
 1 H-NMR:? 7.57 (m, 7H), 7.77 (s, IH), 7.87 (d, IH), 7.98 s, 1 H)

[[ 준비예Preparation Example 8]  8] ICIC -8의 합성Synthesis of -8

Figure 112013091458803-pat00027
Figure 112013091458803-pat00027

IC-3 대신 IC-7 (18.44 g, 46.17 mmol)을 사용하고, 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol) 대신 1-bromo-4-iodobenzene (19.59 g, 69.26 mmol)을 사용하는 것을 제외하고는 준비예 4와 동일한 과정을 수행하여 IC-8을 얻었다.1-bromo-4-iodobenzene (19.59 g, 69.26 mmol) was used instead of 1-bromo-3-iodobenzene (19.59 g, 69.26 mmol) using IC-7 (18.44 g, 46.17 mmol) instead of IC- , IC-8 was obtained by carrying out the same procedure as in Preparation Example 4. [

1H NMR: δ 7.55 (m, 10H), 7.76 (s, 1H), 7.99 (m, 2H), 8.16 (m, 4H), 8.45 (m, 3H)
 1 H NMR:? 7.55 (m, 10H), 7.76 (s, IH), 7.99 (m, 2H), 8.16 (m, 4H), 8.45

[[ 준비예Preparation Example 9]  9] ICIC -9의 합성Synthesis of -9

Figure 112013091458803-pat00028
Figure 112013091458803-pat00028

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.06 g, 7.03 mmol)를 사용하고, 3-bromo-9H-carbazole 대신 10-bromo-7H-benzo[c]carbazole (2.50 g, 8.43 mmol)을 사용하는 것을 제외하고는 준비예 3과 동일한 과정을 수행하여 IC-9를 얻었다.Dibenzo [b, d] furan-4-yl) - 9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Bromo-7H-benzo [c] carbazole (2.50 g, 7.03 mmol) instead of 3-bromo-9H- , 8.43 mmol) was used as the starting material, to obtain IC-9.

1H-NMR: δ 7.36 (m, 3H), 7.66 (m, 6H), 7.81 (m, 5H), 8.16 (d, 1H), 8.54 (d, 1H), 10.12 (s, 1H)
 1 H-NMR:? 7.36 (m, 3H), 7.66 (m, 6H), 7.81 (m, 5H), 8.16 (d,

[[ 준비예Preparation Example 10]  10] ICIC -10의 합성Synthesis of -10

Figure 112013091458803-pat00029
Figure 112013091458803-pat00029

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 대신 2-(9,9-dimethyl-9H-fluoren-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.25 g, 7.03 mmol)를 사용하고, 3-bromo-9H-carbazole 대신 2-bromo-11,11-dimethyl-5,11-dihydroindeno[1,2-b]carbazole (3.05 g, 8.43 mmol)을 사용하는 것을 제외하고는 준비예 3과 동일한 과정을 수행하여 IC-10을 얻었다.(9,9-dimethyl-9H-fluoren-3-yl) -9-phenyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- ) 2-bromo-11,11-dimethyl-5, 3-bromo-9H-carbazole was used instead of 3-bromo- IC-10 was obtained in the same manner as in Preparation Example 3 except that 11-dihydroindeno [1,2-b] carbazole (3.05 g, 8.43 mmol) was used.

1H-NMR: δ 1.73 (s, 12H), 7.26 (m, 2H), 7.40 (m, 2H), 7.58 (m, 5H), 7.69 (d, 1H), 7.77 (s, 1H), 7.87 (m, 2H), 8.09 (m, 3H), 10.19 (s, 1H)
 1 H-NMR: δ 1.73 ( s, 12H), 7.26 (m, 2H), 7.40 (m, 2H), 7.58 (m, 5H), 7.69 (d, 1H), 7.77 (s, 1H), 7.87 ( m, 2 H), 8.09 (m, 3 H), 10.19 (s, 1 H)

[[ 합성예Synthetic example 1] C-1의 합성 1] Synthesis of C-1

<단계 1> 2-<Step 1> 2- chlorochloro -4-(-4-( dibenzodibenzo [b,d]furan-4-[b, d] furan-4- ylyl )-6-) -6- phenylphenyl -1,3,5--1,3,5- triazinetriazine 의 합성Synthesis of

Figure 112013091458803-pat00030
Figure 112013091458803-pat00030

50 ml의 anhydrous tetrahydrofuran 용매에 magnesium (14.5 g, 598 mmol), iodine (3.0 g, 12 mmol)를 녹인 후, anhydrous tetrahydrofuran 130ml에 bromobenzene (93.89 g, 598 mmol)를 녹인 용액을 30분간 한 방울씩 첨가한다. 이 혼합물을 80?에서 2시간 동안 교반한 후 상온에서 식힌다. 그 후, anhydrous tetrahydrofuran 390 ml에 녹인 IC-1 (189.05 g, 598 mmol) 용액을 3시간 동안 교반시키면서 한 방울씩 첨가한다.After dissolving magnesium (14.5 g, 598 mmol) and iodine (3.0 g, 12 mmol) in 50 ml of anhydrous tetrahydrofuran, bromobenzene (93.89 g, 598 mmol) was dissolved in 130 ml of anhydrous tetrahydrofuran do. The mixture is stirred at 80 ° C for 2 hours and then cooled at room temperature. Then, a solution of IC-1 (189.05 g, 598 mmol) dissolved in 390 ml of anhydrous tetrahydrofuran is added dropwise with stirring for 3 hours.

반응이 종결된 후 감압 증류하여 유기 용매를 제거하고 컬럼크로마토그래피로 정제한 후 methanol로 재결정을 실시하여 얻어낸 결정을 여과하여 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (162.58 g, 수율 86%)을 얻었다.After the reaction was completed, the organic solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography and recrystallized from methanol. The resulting crystals were filtered to obtain 2-chloro-4- (dibenzo [b, d] furan- -6-phenyl-1,3,5-triazine (162.58 g, yield 86%).

GC-Mass (이론치: 357.79 g/mol, 측정치: 357 g/mol)GC-Mass (357.79 g / mol, measured: 357 g / mol)

<단계 2> C-1의 합성<Step 2> Synthesis of C-1

Figure 112013091458803-pat00031
Figure 112013091458803-pat00031

질소 기류 하에서 IC-3 (8.45 g, 20.7 mmol), 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine (8.87 g, 24.8 mmol), NaH (746 mg, 31.1 mmol) 및 DMF(300 ml)를 혼합하고 상온에서 3시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후 컬럼 크로마토그래피로 정제하여 목적 화합물인 C-1 (8.91 g, 수율 59%)을 얻었다.(8.45 g, 20.7 mmol) and 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- mmol), NaH (746 mg, 31.1 mmol) and DMF (300 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, and the solid compound was filtered and purified by column chromatography to obtain the target compound C-1 (8.91 g, yield 59%).

GC-Mass (이론치: 729.82 g/mol, 측정치: 729 g/mol)
GC-Mass (calculated: 729.82 g / mol, measured: 729 g / mol)

[[ 합성예Synthetic example 2] C-2의 합성 2] Synthesis of C-2

<단계 1> 2-([1,1'-<Step 1> Synthesis of 2 - ([1,1'- biphenylbiphenyl ]-3-] -3- ylyl )-4-)-4- chlorochloro -6-(-6- ( dibenzodibenzo [b,d]furan-2-[b, d] furan-2- ylyl )-1,3,5-triazine의 합성) -1,3,5-triazine

Figure 112013091458803-pat00032
Figure 112013091458803-pat00032

bromobenzene 대신 3-bromo-1,1'-biphenyl (139.39 g, 598 mmol)을 사용하고, IC-1 대신 IC-2 (189.05 g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazine (176.43 g, 수율 68%)을 얻었다.except that 3-bromo-1,1'-biphenyl (139.39 g, 598 mmol) was used in place of bromo- benzene and IC-2 (189.05 g, 598 mmol) was used in place of IC- Biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3,5 -triazine (176.43 g, yield 68%).

GC-Mass (이론치: 433.89 g/mol, 측정치: 433 g/mol)GC-Mass (calculated: 433.89 g / mol, measured: 433 g / mol)

<단계 2> C-2의 합성<Step 2> Synthesis of C-2

Figure 112013091458803-pat00033
Figure 112013091458803-pat00033

bromobenzene 대신 IC-4 (336.96 g, 598 mmol)을 사용하고, IC-1 대신 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazine (259.46 g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 목적 화합물인 C-2 (369.21 g, 수율 70%)을 얻었다.([1,1'-biphenyl] -3-yl) -4-chloro-6- (dibenzo [b, d] The same procedure as in <Step 1> of Synthesis Example 1 was carried out except that furan-2-yl) -1,3,5-triazine (259.46 g, 598 mmol) was used to obtain the desired compound C-2 (369.21 g, yield 70%).

GC-Mass (이론치: 882.02 g/mol, 측정치: 882 g/mol)
GC-Mass (calculated: 882.02 g / mol, measured: 882 g / mol)

[[ 합성예Synthetic example 3] C-3의 합성 3] Synthesis of C-3

<단계 1> 2-<Step 1> 2- chlorochloro -4,6--4,6- bisbis (( dibenzodibenzo [b,d]furan-4-[b, d] furan-4- ylyl )-1,3,5-) -1,3,5- triazinetriazine 의 합성Synthesis of

Figure 112013091458803-pat00034
Figure 112013091458803-pat00034

bromobenzene 대신 4-bromodibenzo[b,d]furan (147.75 g, 598 mmol)을 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 2-chloro-4,6-bis(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (203.54 g, 수율 76%)을 얻었다.4-bromobenzo [b, d] furan (147.75 g, 598 mmol) was used in place of 4-bromobenzene instead of 2-chloro-4,6-bis [b, d] furan-4-yl) -1,3,5-triazine (203.54 g, yield 76%).

GC-Mass (이론치: 447.87 g/mol, 측정치: 447 g/mol)GC-Mass (calculated: 447.87 g / mol, measured: 447 g / mol)

<단계 2> C-3의 합성<Step 2> Synthesis of C-3

Figure 112013091458803-pat00035
Figure 112013091458803-pat00035

bromobenzene 대신 IC-4 (336.96 g, 598 mmol)을 사용하고, IC-1 대신 2-chloro-4,6-bis(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (267.82 g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 목적 화합물인 C-3 (289.33 g, 수율 54%)을 얻었다.(336.96 g, 598 mmol) instead of 2-chloro-4,6-bis (dibenzo [b, d] furan-4-yl) -1,3,5-triazine (289.33 g, yield 54%) was obtained by carrying out the same procedure as in <Step 1> of Preparation Example 1, except that the title compound (267.82 g, 598 mmol) was used.

GC-Mass (이론치: 896.00 g/mol, 측정치: 896 g/mol)
GC-Mass (896.00 g / mol, measured: 896 g / mol)

[[ 합성예Synthetic example 4] C-4의 합성 4] Synthesis of C-4

<단계 1> 2-<Step 1> 2- chlorochloro -4-(-4-( dibenzodibenzo [b,d]furan-4-[b, d] furan-4- ylyl )-6-() -6- ( naphthalennaphthalen -1--One- ylyl )-1,3,5-triazine의 합성) -1,3,5-triazine

Figure 112013091458803-pat00036
Figure 112013091458803-pat00036

bromobenzene 대신 1-bromonaphthalene (123.82 g, 598 mmol)을 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-(naphthalen-1-yl)-1,3,5-triazine (187.79 g, 수율 77%)을 얻었다.dibenzo [b, d] furan-4-one was obtained by following the same procedure as in <Step 1> of Preparation Example 1, except that 1-bromonaphthalene (123.82 g, 598 mmol) yl) -6- (naphthalen-1-yl) -1,3,5-triazine (187.79 g, yield 77%).

GC-Mass (이론치: 407.85 g/mol, 측정치: 407 g/mol)GC-Mass (theory: 407.85 g / mol, measurement: 407 g / mol)

<단계 2> C-4의 합성&Lt; Step 2 > Synthesis of C-4

Figure 112013091458803-pat00037
Figure 112013091458803-pat00037

IC-3 대신 IC-5 (10.83 g, 20.7 mmol)를 사용하고, 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-(naphthalen-1-yl)-1,3,5-triazine (10.11 g, 24.8 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 2>와 동일한 과정을 수행하여 목적 화합물인 C-4 (11.85 g, 수율 64%)을 얻었다.Instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine using IC-5 (10.83 g, 20.7 mmol) Except that 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6- (naphthalen-1-yl) -1,3,5-triazine (10.11 g, 24.8 mmol) (11.85 g, yield 64%) was obtained by carrying out the same procedure as <Step 2> of the synthesis example 1 with the aimed compound C-4.

GC-Mass (이론치: 895.02 g/mol, 측정치: 895 g/mol)
GC-Mass (calculated: 895.02 g / mol, measured: 895 g / mol)

[[ 합성예Synthetic example 5] C-5의 합성 5] Synthesis of C-5

<단계 1> 2-<Step 1> 2- chlorochloro -4-(-4-( dibenzodibenzo [b,d]furan-4-[b, d] furan-4- ylyl )-6-() -6- ( pyridinpyridine -2--2- ylyl )-1,3,5-) -1,3,5- triazinetriazine 의 합성Synthesis of

Figure 112013091458803-pat00038
Figure 112013091458803-pat00038

bromobenzene 대신 2-bromopyridine (94.48g, 598 mmol)을 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-(pyridin-2-yl)-1,3,5-triazine (128.73 g, 수율 60%)을 얻었다.dibenzo [b, d] furan-4-one was obtained by following the procedure of <Step 1> of Preparation Example 1, except that 2-bromopyridine (94.48 g, 598 mmol) yl) -6- (pyridin-2-yl) -1,3,5-triazine (128.73 g, yield 60%).

GC-Mass (이론치: 358.78 g/mol, 측정치: 358 g/mol)GC-Mass (theory: 358.78 g / mol, measured: 358 g / mol)

<단계 2> C-5의 합성<Step 2> Synthesis of C-5

Figure 112013091458803-pat00039
Figure 112013091458803-pat00039

bromobenzene 대신 IC-6 (405.81 g, 598 mmol)을 사용하고, IC-1 대신 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-(pyridin-2-yl)-1,3,5-triazine (214.55 g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 목적 화합물인 C-5 (181.95 g, 수율 33%)를 얻었다.(dibenzo [b, d] furan-4-yl) -6- (pyridin-2-yl) - (181.95 g, yield 33%) was obtained by carrying out the same procedure as in <Step 1> of Synthesis Example 1, except that 1,3,5-triazine (214.55 g, 598 mmol) .

GC-Mass (이론치: 922.04 g/mol, 측정치: 922 g/mol)
GC-Mass (calculated: 922.04 g / mol, measured: 922 g / mol)

[[ 합성예Synthetic example 6] C-6의 합성 6] Synthesis of C-6

<단계 1> 4-(4-<Step 1> Synthesis of 4- (4- chlorochloro -6-(-6- ( dibenzodibenzo [b,d]furan-4-[b, d] furan-4- ylyl )-1,3,5-) -1,3,5- triazintriazin -2--2- ylyl )-N,N-diphenylaniline의 합성) -N, N-diphenylaniline

Figure 112013091458803-pat00040
Figure 112013091458803-pat00040

bromobenzene 대신 4-bromo-N,N-diphenylaniline (193.87g, 598 mmol)을 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 4-(4-chloro-6-(dibenzo[b,d]furan-4-yl)-1,3,5-triazin-2-yl)-N,N-diphenylaniline (244.88 g, 수율 78%)을 얻었다.(4-bromo-N, N-diphenylaniline (193.87 g, 598 mmol) was used in place of bromobenzene in Step 1 of Preparation Example 1, [b, d] furan-4-yl) -1,3,5-triazin-2-yl) -N, N-diphenylaniline (244.88 g, yield 78%).

GC-Mass (이론치: 525.00 g/mol, 측정치: 525 g/mol)GC-Mass (calculated: 525.00 g / mol, measured: 525 g / mol)

<단계 2> C-6의 합성<Step 2> Synthesis of C-6

Figure 112013091458803-pat00041
Figure 112013091458803-pat00041

IC-3 대신 IC-7 (8.27 g, 20.7 mmol)를 사용하고, 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine 대신 4-(4-chloro-6-(dibenzo[b,d]furan-4-yl)-1,3,5-triazin-2-yl)-N,N-diphenylaniline (13.02 g, 24.8 mmol)를 사용하는 것을 제외하고는, 합성예 1의 <단계 2>와 동일한 과정을 수행하여 목적 화합물인 C-6 (9.19 g, 수율 50%)을 얻었다.Instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine using IC-7 (8.27 g, 20.7 mmol) Using 4-chloro-6- (dibenzo [b, d] furan-4-yl) -1,3,5-triazin-2-yl) -N, N-diphenylaniline (13.02 g, 24.8 mmol) , The target compound C-6 (9.19 g, yield 50%) was obtained in the same manner as in < Step 2 >

GC-Mass (이론치: 888.04 g/mol, 측정치: 888 g/mol)
GC-Mass (calculated: 888.04 g / mol, measured: 888 g / mol)

[[ 합성예Synthetic example 7] C-7의 합성 7] Synthesis of C-7

<단계 1> 9-(4-(4-&Lt; Step 1 > 9- (4- (4- chlorochloro -6-(-6- ( dibenzodibenzo [b,d]furan-2-[b, d] furan-2- ylyl )-1,3,5-) -1,3,5- triazintriazin -2-yl)phenyl)-9H-carbazole의 합성-2-yl) phenyl) -9H-carbazole

Figure 112013091458803-pat00042
Figure 112013091458803-pat00042

bromobenzene 대신 9-(4-bromophenyl)-9H-carbazole (192.67g, 598 mmol)을 사용하고, IC-1 대신 IC-2 (189.05g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 9-(4-(4-chloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole (134.47 g, 수율 43%)을 얻었다.except that 9- (4-bromophenyl) -9H-carbazole (192.67 g, 598 mmol) was used in place of bromobenzene and IC-2 (189.05 g, 598 mmol) Dibenzo [b, d] furan-2-yl) -1,3,5-triazin-2-yl) phenyl) - 9H-carbazole (134.47 g, yield 43%).

GC-Mass (이론치: 522.98 g/mol, 측정치: 522 g/mol)GC-Mass (calculated: 522.98 g / mol, measured: 522 g / mol)

<단계 2> C-7의 합성<Step 2> Synthesis of C-7

Figure 112013091458803-pat00043
Figure 112013091458803-pat00043

bromobenzene 대신 IC-8 (331.59 g, 598 mmol)을 사용하고, IC-1 대신 9-(4-(4-chloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole (312.74 g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 목적 화합물인 C-7 (253.15 g, 수율 44%)을 얻었다.(4-chloro-6- (dibenzo [b, d] furan-2-yl) -1,3-dihydroxybenzoate was used instead of IC- The same procedure as in <Step 1> of Synthesis Example 1 was carried out except that 5-triazin-2-yl) phenyl) -9H-carbazole (312.74 g, 598 mmol) g, yield: 44%).

GC-Mass (이론치: 962.12 g/mol, 측정치: 962 g/mol)
GC-Mass (calculated: 962.12 g / mol, measured: 962 g / mol)

[[ 합성예Synthetic example 8] C-8의 합성 8] Synthesis of C-8

<단계 1> 2-<Step 1> 2- chlorochloro -4-(-4-( dibenzodibenzo [b,d]furan-2-[b, d] furan-2- ylyl )-6-(9,9-) -6- (9,9- dimethyldimethyl -9H--9H- fluorenfluoren -3-yl)-1,3,5-triazine의 합성-3-yl) -1,3,5-triazine

Figure 112013091458803-pat00044
Figure 112013091458803-pat00044

bromobenzene 대신 3-bromo-9,9-dimethyl-9H-fluorene (163.35g, 598 mmol)을 사용하고, IC-1 대신 IC-2 (189.05g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 화합물 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-(9,9-dimethyl-9H-fluoren-3-yl)-1,3,5-triazine (161.55 g, 수율 57%)을 얻었다.except that 3-bromo-9,9-dimethyl-9H-fluorene (163.35 g, 598 mmol) was used in place of bromobenzene and IC-2 (189.05 g, 598 mmol) Dibenzo [b, d] furan-2-yl) -6- (9,9-dimethyl-9H-fluoren-3-yl) - 1,3,5-triazine (161.55 g, yield 57%).

GC-Mass (이론치: 473.95 g/mol, 측정치: 473 g/mol)GC-Mass (calculated: 473.95 g / mol, measured: 473 g / mol)

<단계 2> C-8의 합성<Step 2> Synthesis of C-8

Figure 112013091458803-pat00045
Figure 112013091458803-pat00045

IC-3 대신 IC-9 (7.94 g, 20.7 mmol)를 사용하고, 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-(9,9-dimethyl-9H-fluoren-3-yl)-1,3,5-triazine (11.75 g, 24.8 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 2>와 동일한 과정을 수행하여 목적 화합물인 C-8 (13.42 g, 수율 79%)을 얻었다.Instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine using IC-9 (7.94 g, 20.7 mmol) 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (9,9-dimethyl-9H- fluoren- mmol), the target compound C-8 (13.42 g, yield 79%) was obtained in the same manner as in <Step 2> of Synthesis Example 1.

GC-Mass (이론치: 820.93 g/mol, 측정치: 820 g/mol)
GC-Mass (calculated: 820.93 g / mol, measured: 820 g / mol)

[[ 합성예Synthetic example 9] C-9의 합성 9] Synthesis of C-9

<단계 1> 2-<Step 1> 2- chlorochloro -4-(-4-( dibenzodibenzo [b,d]furan-2-[b, d] furan-2- ylyl )-6-(6-) -6- (6- phenylpyridinphenylpyridine -3--3- ylyl )-1,3,5-triazine 의 합성) -1,3,5-triazine

Figure 112013091458803-pat00046
Figure 112013091458803-pat00046

bromobenzene 대신 5-bromo-2-phenylpyridine (139.98g, 598 mmol)을 사용하고, IC-1 대신 IC-2 (189.05g, 598 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 1>과 동일한 과정을 수행하여 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-(6-phenylpyridin-3-yl)-1,3,5-triazine (161.23 g, 수율 62%)을 얻었다.Step 1> of Synthesis Example 1 was repeated except that 5-bromo-2-phenylpyridine (139.98 g, 598 mmol) was used instead of bromobenzene and IC-2 (189.05 g, 598 mmol) Dibenzo [b, d] furan-2-yl) -6- (6-phenylpyridin-3-yl) -1,3,5-triazine (161.23 g, yield 62 %).

GC-Mass (이론치: 434.88 g/mol, 측정치: 434 g/mol)GC-Mass (calculated: 434.88 g / mol, measured: 434 g / mol)

<단계 2> C-9의 합성<Step 2> Synthesis of C-9

Figure 112013091458803-pat00047
Figure 112013091458803-pat00047

IC-3 대신 IC-10 (9.84 g, 20.7 mmol)를 사용하고, 2-chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine 대신 2-chloro-4-(dibenzo[b,d]furan-2-yl)-6-(6-phenylpyridin-3-yl)-1,3,5-triazine (10.78 g, 24.8 mmol)를 사용하는 것을 제외하고는 합성예 1의 <단계 2>와 동일한 과정을 수행하여 목적 화합물인 C-9 (9.95 g, 수율 55%)을 얻었다.Instead of 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine using IC-10 (9.84 g, 20.7 mmol) 2-chloro-4- (dibenzo [b, d] furan-2-yl) -6- (6-phenylpyridin- 3- yl) -1,3,5-triazine (10.78 g, 24.8 mmol) , The target compound C-9 (9.95 g, yield 55%) was obtained in the same manner as in <Step 2> of Synthesis Example 1,

GC-Mass (이론치: 874.04 g/mol, 측정치: 874 g/mol)
GC-Mass (calculated: 874.04 g / mol, measured: 874 g / mol)

[[ 실시예Example 1 내지 9] 녹색 유기  1 to 9] green organic 전계Field 발광 소자 제조 Light emitting device manufacturing

합성예 1 내지 9에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.The compounds synthesized in Synthesis Examples 1 to 9 were subjected to high purity sublimation purification by a conventionally known method, and a green organic electroluminescent device was fabricated according to the following procedure.

먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech), the substrate was cleaned using UV for 5 minutes, The substrate was transferred.

이렇게 준비된 ITO 투명 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 합성예 1 내지 9에서 합성한 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.
M-MTDATA (60 nm) / TCTA (80 nm) / each compound synthesized in Synthesis Examples 1 to 9 + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) on the ITO transparent substrate ) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

[[ 비교예Comparative Example 1 내지 2] 녹색 유기  1 to 2] green organic 전계Field 발광 소자 제조 Light emitting device manufacturing

발광층 형성시 발광 호스트 물질로서 합성예 1의 화합물 대신 CBP 및 Ref-1을 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 소자를 제조하였다.
A device was prepared in the same manner as in Example 1, except that CBP and Ref-1 were used instead of the compound of Synthesis Example 1 as a luminescent host material in forming the light emitting layer.

상기 실시예 1 내지 9 및 비교예 1, 2에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, BCP, CBP 및 Ref-1의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , BCP, CBP and Ref-1 used in Examples 1 to 9 and Comparative Examples 1 and 2 are as follows.

Figure 112013091458803-pat00048
Figure 112013091458803-pat00048

Figure 112013091458803-pat00049
Figure 112013091458803-pat00049

Figure 112013091458803-pat00050

Figure 112013091458803-pat00050

[[ 평가예Evaluation example 1] One]

실시예 1 내지 9 및 비교예 1, 2에서 제조한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.The driving voltage, current efficiency and emission peak at the current density of 10 mA / cm 2 were measured for each of the green organic electroluminescent devices prepared in Examples 1 to 9 and Comparative Examples 1 and 2, Respectively.

샘플Sample 호스트Host 구동 전압(V)The driving voltage (V) EL 피크(nm)EL peak (nm) 전류효율(cd/A)Current efficiency (cd / A) 실시예 1Example 1 C-1C-1 6.606.60 519519 42.042.0 실시예 2Example 2 C-2C-2 6.556.55 520520 41.541.5 실시예 3Example 3 C-3C-3 6.456.45 518518 41.241.2 실시예 4Example 4 C-4C-4 6.506.50 518518 41.941.9 실시예 5Example 5 C-5C-5 6.506.50 518518 41.741.7 실시예 6Example 6 C-6C-6 6.606.60 521521 41.041.0 실시예 7Example 7 C-7C-7 6.406.40 522522 40.740.7 실시예 8Example 8 C-8C-8 6.456.45 522522 40.840.8 실시예 9Example 9 C-9C-9 6.506.50 521521 41.541.5 비교예 1Comparative Example 1 CBPCBP 6.936.93 516516 38.238.2 비교예 2Comparative Example 2 Ref-1Ref-1 6.756.75 517517 40.240.2

상기 표 1에 나타낸 바와 같이, 본 발명의 화합물을 녹색 유기 전계 발광 소자의 발광층에 적용한 실시예 1 내지 9는 종래 CBP 및 Ref-1를 녹색 유기 전계 발광 소자의 발광층에 적용한 비교예 1 및 2에 비해 효율 및 구동전압이 우수한 것을 확인할 수 있었다.
As shown in Table 1, Examples 1 to 9, in which the compound of the present invention was applied to a light emitting layer of a green organic electroluminescent device, were compared with Comparative Examples 1 and 2 in which CBP and Ref-1 were applied to a light emitting layer of a green organic electroluminescent device The efficiency and the driving voltage were superior.

[[ 실시예Example 10 내지 12] 적색 유기  10 to 12] Red organic 전계Field 발광 소자 제조 Light emitting device manufacturing

합성예 6 내지 8에서 합성된 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제조하였다.The compounds synthesized in Synthesis Examples 6 to 8 were subjected to high purity sublimation purification by a conventionally known method, and then a red organic electroluminescent device was manufactured according to the following procedure.

먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후, UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1500 Å was ultrasonically washed with distilled water. After washing with distilled water, ultrasonic cleaning was performed using a solvent such as isopropyl alcohol, acetone, and methanol, and the substrate was dried and transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tec). Then, the substrate was cleaned using UV for 5 minutes, The substrate was transferred to an evaporator.

이렇게 준비된 ITO 투명 기판(전극) 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 합성예 6 내지 8에서 합성한 각각의 화합물 + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.
M-MTDATA (60 nm) / TCTA (80 nm) / each compound synthesized in Synthesis Examples 6 to 8 + 10% (piq) 2 Ir (acac) (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

[[ 비교예Comparative Example 3] 적색 유기  3] Red organic 전계Field 발광 소자 제조 Light emitting device manufacturing

발광층 형성시 발광 호스트 물질로서 합성예 6의 화합물 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 10과 동일한 과정으로 소자를 제조하였다.
A device was fabricated in the same manner as in Example 10, except that CBP was used instead of the compound of Synthesis Example 6 as a luminescent host material in forming the light emitting layer.

상기 실시예 10 내지 12 및 비교예 3에서 사용된 m-MTDATA, (piq)2Ir(acac), BCP, NPB 및 CBP의 구조는 하기와 같다.The structures of m-MTDATA, (piq) 2 Ir (acac), BCP, NPB and CBP used in Examples 10 to 12 and Comparative Example 3 are as follows.

Figure 112013091458803-pat00051
Figure 112013091458803-pat00051

Figure 112013091458803-pat00052

Figure 112013091458803-pat00052

[[ 평가예Evaluation example 2] 2]

실시예 10 내지 12 및 비교예 3에서 제조한 각각의 적색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.The driving voltage and current efficiency at the current density of 10 mA / cm 2 were measured for each red organic electroluminescent device manufactured in Examples 10 to 12 and Comparative Example 3, and the results are shown in Table 2 below.

샘플Sample 호스트Host 구동 전압(V)The driving voltage (V) 전류효율(cd/A)Current efficiency (cd / A) 실시예 10Example 10 C-6C-6 4.904.90 13.013.0 실시예 11Example 11 C-7C-7 4.954.95 12.512.5 실시예 12Example 12 C-8C-8 4.854.85 12.712.7 비교예 3Comparative Example 3 CBPCBP 5.255.25 8.28.2

상기 표 2에 나타낸 바와 같이, 본 발명의 화합물을 적색 유기 전계 발광 소자의 발광층에 적용한 실시예 10 내지 12는 종래 CBP를 적색 유기 전계 발광 소자의 발광층에 적용한 비교예 3에 비해 효율 및 구동전압이 우수한 것을 확인할 수 있었다.As shown in Table 2, in Examples 10 to 12 in which the compound of the present invention was applied to the light emitting layer of a red organic electroluminescent device, compared to Comparative Example 3 in which CBP was applied to the light emitting layer of a red organic electroluminescent device, I was able to confirm that it was excellent.

Claims (9)

하기 화학식 2 내지 4 및 6 내지 10으로 표시되는 화합물로 이루어진 군에서 선택되는 화합물:
[화학식 2]
Figure 112016006353761-pat00053

[화학식 3]
Figure 112016006353761-pat00054

[화학식 4]
Figure 112016006353761-pat00055

[화학식 6]
Figure 112016006353761-pat00056

[화학식 7]
Figure 112016006353761-pat00057

[화학식 8]
Figure 112016006353761-pat00058

[화학식 9]
Figure 112016006353761-pat00059

[화학식 10]
Figure 112016006353761-pat00060

상기 화학식 2 내지 4 및 6 내지 10에서,
L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기, 또는 핵원자수 5 내지 18의 헤테로아릴렌기이고,
X1 내지 X3는 각각 독립적으로 N 또는 C(R11)이고, 이때, 적어도 하나 이상은 N이며,
Y1은 N(R12), O, S, Se, C(R13)(R14) 및 Si(R15)(R16)로 이루어진 군에서 선택되며,
R3 내지 R6 및 R11 내지 R16은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,
Ar1은 핵원자수 5 내지 40의 헤테로아릴기이고,
상기 R3 내지 R6 및 R11 내지 R16의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴실릴기와, 상기 Ar1의 헤테로아릴기는 각각 독립적으로, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C40의 아릴보론기, C6~C40의 아릴포스핀기, C6~C40의 아릴포스핀옥사이드기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상으로 치환될 수 있으며,
m 및 n은 각각 독립적으로 0 내지 4의 정수이고,
l 및 p는 각각 독립적으로 0 내지 4의 정수이다.Compounds represented by the following formulas (2) to (4) and (6) to (10)
(2)
Figure 112016006353761-pat00053

(3)
Figure 112016006353761-pat00054

[Chemical Formula 4]
Figure 112016006353761-pat00055

[Chemical Formula 6]
Figure 112016006353761-pat00056

(7)
Figure 112016006353761-pat00057

[Chemical Formula 8]
Figure 112016006353761-pat00058

[Chemical Formula 9]
Figure 112016006353761-pat00059

[Chemical formula 10]
Figure 112016006353761-pat00060

In the above Chemical Formulas 2 to 4 and 6 to 10,
L 1 and L 2 are each independently a single bond, a C 6 to C 18 arylene group, or a heteroarylene group having 5 to 18 nuclear atoms,
X 1 to X 3 are each independently N or C (R 11 ), wherein at least one is N,
Y 1 is selected from the group consisting of N (R 12), O, S, Se, C (R 13) (R 14) and Si (R 15) (R 16 ),
R 3 to R 6 and R 11 to R 16 each independently represent hydrogen, deuterium, halogen, cyano, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C 40 alkynyl, A C 6 to C 40 aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C 6 to C 40 aryloxy group, a C 1 to C 40 alkyloxy group, a C 6 to C 40 arylamine group, A C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 1 to C 40 alkylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 40 arylboron group, A C 6 to C 40 arylphosphine group, a C 6 to C 40 arylphosphine oxide group, and a C 6 to C 40 arylsilyl group,
Ar 1 is a heteroaryl group having 5 to 40 nuclear atoms,
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, cycloalkyl group, heterocycloalkyl group and alkylsilyl group of R 3 to R 6 and R 11 to R 16 , alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group, said Ar 1 heteroaryl group, each independently of, deuterium, halogen, cyano, C alkyl group of 1 ~ C 40, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, an aryloxy group of a heteroaryl group of C 6 ~ C 40 aryl group, the number of nuclear atoms of 5 to 40, C 6 ~ C 40 of, C 1 ~ alkyloxy of C 40, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ of C 40 alkyl group of boron, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl group consisting of Lt; RTI ID = 0.0 &gt; 1, &lt; / RTI &gt;
m and n are each independently an integer of 0 to 4,
l and p each independently represent an integer of 0 to 4; 삭제delete 제1항에 있어서,
상기 Y1은 N(R12)이고, R12는 페닐기인 것을 특징으로 하는 화합물.The method according to claim 1,
Wherein Y 1 is N (R 12 ) and R 12 is a phenyl group. 제1항에 있어서,
상기 Y1은 C(R13)(R14)이고, R13 및 R14는 메틸기인 것을 특징으로 하는 화합물.The method according to claim 1,
Wherein Y 1 is C (R 13 ) (R 14 ), and R 13 and R 14 are methyl groups. 제1항에 있어서,
상기 L1 및 L2는 각각 독립적으로 단일결합, 페닐렌 또는 비페닐렌인 것을 특징으로 하는 화합물.The method according to claim 1,
Wherein L 1 and L 2 are each independently a single bond, phenylene or biphenylene. 제1항에 있어서,
상기 X1 내지 X3는 N인 것을 특징으로 하는 화합물.The method according to claim 1,
Wherein X 1 to X 3 are N. 삭제delete 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며,
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 및 제3항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.A cathode, and at least one organic layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes the compound according to any one of claims 1 to 6. 제8항에 있어서,
상기 화합물을 포함하는 유기물층은 인광 발광층인 것을 특징으로 하는 유기 전계 발광 소자.9. The method of claim 8,
Wherein the organic compound layer containing the compound is a phosphorescent light-emitting layer.
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