KR20150070617A - 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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KR20150070617A
KR20150070617A KR1020130157052A KR20130157052A KR20150070617A KR 20150070617 A KR20150070617 A KR 20150070617A KR 1020130157052 A KR1020130157052 A KR 1020130157052A KR 20130157052 A KR20130157052 A KR 20130157052A KR 20150070617 A KR20150070617 A KR 20150070617A
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KR101667447B1 (en
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배형찬
백영미
이인혁
김은진
김영배
김태형
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주식회사 두산
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Abstract

The present invention relates to novel benzo pyrrole carbazole-based compounds having excellent hole injection and transport ability, light emitting ability, etc, and to an organic electroluminescent device comprising the same in one or more organic layers, thereby improving properties such as luminous efficiency, driving voltage, lifespan, etc.

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 상기 화합물을 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic compound and an organic electroluminescent device including the compound.

유기 전계 발광 소자는 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. 상기 유기물층에 포함되는 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. The material contained in the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, or the like depending on its function.

상기 발광 물질은 발광색에 따라 청색, 녹색, 적색의 발광 물질과, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색의 발광 물질로 구분될 수 있다. 또한 색순도의 증가와 에너지 전이를 통해 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. A host / dopant system can be used as a luminescent material to increase the luminous efficiency through increase of color purity and energy transfer.

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 유리전이온도가 낮고 열적 안정성이 좋지 않아 유기 전계 발광 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있으며, 발광 특성 측면에서도 여전히 개선이 필요하다.However, since the conventional materials have low glass transition temperature and poor thermal stability, they are not satisfactory in terms of lifetime in organic electroluminescent devices, and still need improvement in terms of luminescent properties.

대한민국 공개특허 2011-0066763Korea public patent 2011-0066763

상기한 문제점을 해결하기 위해 본 발명은 유리 전이온도가 높으며 열적 안정성이 우수하고, 발광 특성이 뛰어난 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 having a high glass transition temperature, excellent thermal stability, and excellent luminescent properties.

또 본 발명은 상기 유기 화합물을 포함하는 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.Another object of the present invention is to provide an organic electroluminescent device comprising the organic compound.

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 pat00001
Figure pat00001

상기 화학식 1에서,In Formula 1,

R1과 R2 및 R2와 R3 중 적어도 하나는 서로 결합하여 하기 화학식 2로 표시되는 축합 고리를 형성하며,At least one of R 1 and R 2 and R 2 and R 3 is bonded to each other to form a condensed ring represented by the following formula (2)

[화학식 2](2)

Figure pat00002
Figure pat00002

상기 화학식 2에서,In Formula 2,

점선은 화학식 1과 결합되는 부분이고,The dotted line is a moiety bonded to the formula (1)

X1은 CAr2Ar3, NAr4, O, S 및 SiAr5Ar6로 이루어진 군에서 선택되며,X 1 is selected from the group consisting of CAr 2 Ar 3 , NAr 4 , O, S and SiAr 5 Ar 6 ,

축합 고리를 형성하는 것을 제외한 상기 R1 내지 R10은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있으며,R 1 to R 10 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, nitro, C 1 to C 40 alkyl, C 2 to C 40 alkenyl, C 2 to C A C 3 to C 40 cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkenyl group, C 6 -C 60 alkyloxy, C 6 -C 60 aryloxy, C 3 -C 40 alkylsilyl, C 6 -C 60 arylsilyl, C 1 -C 40 alkylboron, C 6 -C 60 the arylboronic group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of an aryl amine of the C 60 or the, form a condensed ring by combining adjacent tile In addition,

상기 Ar1 내지 Ar6 은 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,Each of Ar 1 to Ar 6 is independently a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 6 heteroaryl group, 40 alkylsilyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 pingi, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 of is selected from the group consisting of an aryl amine,

상기 R1내지 R10 및 Ar1 내지 Ar6의 알킬기, 알케닐기, 알키닐기 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상으로 치환 또는 비치환될 수 있다. 이때, 복수개의 치환기로 치환될 경우 복수개의 치환기는 서로 동일하거나 상이할 수 있다.Alkyl group of the R 1 to R 10 and Ar 1 to Ar 6, an alkenyl group, an alkynyl group a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, each independently, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ alkynyl group of C 40 , A C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group , A C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group , C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ by at least one member selected from the group consisting of an aryl amine of the C 60 can be unsubstituted or substituted . At this time, when a plurality of substituents are substituted, a plurality of substituents may be the same or different.

한편 본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다. 본 발명에서 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.According to another aspect of the present invention, there is provided an organic electroluminescent device comprising a cathode, 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 the above formula The organic electroluminescent device includes the organic electroluminescent device. In the present invention, alkyl means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

본 발명에서 알케닐(alkenyl)은 탄소-탄소 이중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkenyl means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

본 발명에서 알키닐(alkynyl)은 탄소-탄소 삼중 결합을 1개 이상 가진 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkynyl means a monovalent substituent derived from a straight-chain or branched-chain unsaturated hydrocarbon having 2 to 40 carbon atoms and having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.

본 발명에서 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 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryl 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 발명에서 헤테로아릴은 핵원자수 5 내지 60의 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 포함될 수 있다. 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 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heteroaryl means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 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. It is also possible to include a form in which two or more rings are pendant or condensed with each other, and further, a condensed form with an aryl group may be included. Examples of such heteroaryls include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

본 발명에서 아릴옥시는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 6 내지 60의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있으나, 이에 한정되지는 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 발명에서 알킬옥시는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함할 수 있다. 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyloxy is a monovalent substituent group represented by R'O-, wherein R 'represents alkyl having 1 to 40 carbon atoms, and includes a linear, branched or cyclic structure can do. Examples of alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy and pentoxy.

본 발명에서 아릴아민은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.In the present invention, arylamine refers to an amine substituted with aryl having 6 to 60 carbon atoms.

본 발명에서 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, cycloalkyl 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 발명에서 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 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heterocycloalkyl means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbons, of the ring is N, O, S or Se Lt; / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

본 발명에서 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 60의 아릴로 치환된 실릴을 의미한다.In the present invention, alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms, and arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.

본 발명에서 축합고리는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다.In the present invention, the condensed rings refer to condensed aliphatic rings, condensed aromatic rings, condensed heteroaliphatic rings, condensed heteroaromatic rings, or a combination thereof.

본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명의 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 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound represented by the general formula (1) of the present invention has excellent thermal stability and luminescent 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 of 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 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 발명의 화합물은 벤조피롤카바졸(benzo pyrrole carbazole) 기본 골격에 5원 방향족환, 또는 5원 헤테로 방향족환이 축합되고, 다양한 치환체가 결합된 것으로, 상기 화학식 1로 표시된다. The compound of the present invention is a benzopyrrole carbazole basic skeleton having a 5-membered aromatic ring or a 5-membered heteroaromatic ring condensed with various substituents bonded thereto.

본 발명의 화합물과 같이 전자 공여성이 큰 전자주는기(electron donating group, EDG) 특성을 가져 정공 수송성이 우수한 벤조피롤카바졸 기본 골격에 전자 흡수성이 큰 전자끄는기(electron withdrawing group, EWG)가 도입될 경우, 정공과 전자의 결합력이 높고 분자 전체가 양극성(bipolar)을 가지기 때문에 인광 발광층에서 호스트로서 유리하게 적용할 수 있을 뿐만 아니라 전자수송층에도 적용될 수 있다. 또한 치환기로 전자 공여성이 큰 전자주는기(electron donating group, EDG)가 도입될 경우 정공 수송층, 정공 주입층에도 적용될 수 있다.Electron donating groups (EWG) having electron-donating group (EDG) characteristics such as compounds of the present invention and having high electron-absorbing property on benzopyrrole carbazole basic skeleton having excellent hole transportability It can be applied to an electron transporting layer as well as being advantageously applied as a host in a phosphorescent light emitting layer because of its high bonding force between holes and electrons and having a bipolar structure as a whole. Also, when the electron donating group (EDG) is introduced as the substituent, the electron donating group can be applied to the hole transporting layer and the hole injecting layer.

또한 본 발명의 화합물은 다양한 방향족 환(aromatic ring) 치환체로 인해 분자량이 유의적으로 증대됨으로써 높은 유리전이온도를 가지기 때문에 종래의 유기물층 재료(예를 들어, CBP)보다 열적 안정성이 우수하다. In addition, the compound of the present invention is superior in thermal stability to conventional organic material layers (for example, CBP) because it has a high glass transition temperature because its molecular weight is significantly increased due to various aromatic ring substituents.

따라서 본 발명의 화합물을 유기 전계 발광 소자의 정공 주입층, 정공 수송층, 전자 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.Accordingly, when the compound of the present invention is used as a material for a hole injection layer, a hole transporting layer, an electron transporting layer, or a light emitting layer of an organic electroluminescent device, the efficiency and lifetime of the organic electroluminescent device are improved compared to a conventional organic material layer material (for example, CBP) 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.

이러한 본 발명의 화합물은 유기 전계 발광 소자의 특성을 고려할 때, X1은 NAr4, O 또는 S인 것이 바람직하고, NAr4인 것이 더욱 바람직하다.When these compounds of the present invention consider the characteristics of the organic light emitting device, X 1 is NAr 4, preferably of O or S, and more preferably 4 NAr.

또한 본 발명의 화합물에서, 화합물의 넓은 밴드갭과 열안정성을 고려했을 때, Ar1 내지 Ar6는 각각 독립적으로 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C6~C40의 아릴아민기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되는 것이 바람직하다.In addition, in the compound of the present invention, in consideration of the wide bandgap and thermal stability of the compound, Ar 1 to Ar 6 each independently represent a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, C it is selected from the 6 ~ C 40 aryl amine group, and the group consisting of C 6 ~ C 40 aryl group in the silyl preferred.

또 본 발명의 화합물에서, R1 내지 R10는 각각 독립적으로 수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 것이 바람직하다.In the compound of the present invention, each of R 1 to R 10 independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, A heteroaryl group, and an arylamine group having 6 to 60 carbon atoms.

구체적으로, 본 발명의 화합물에서 Ar1 내지 Ar6 및 R1 내지 R10(축합 고리를 형성하지 않는 것)는 각각 독립적으로 수소 또는 하기 S1 내지 S205로 이루어진 구조(치환체)에서 선택되는 것이 바람직하다.Specifically, in the compound of the present invention, Ar 1 to Ar 6 and R 1 to R 10 (which do not form a condensed ring) are each independently selected from hydrogen or a structure (substituent) composed of the following S1 to S205 .

Figure pat00003
Figure pat00003

Figure pat00004
Figure pat00004

Figure pat00005
Figure pat00005

Figure pat00006
Figure pat00006

Figure pat00007
Figure pat00007

이러한 본 발명의 화합물은 하기 화학식 3 내지 6으로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하다.The compound of the present invention is preferably selected from the group consisting of compounds represented by the following formulas (3) to (6).

[화학식 3](3)

Figure pat00008
Figure pat00008

[화학식 4][Chemical Formula 4]

[화학식 5][Chemical Formula 5]

Figure pat00010
Figure pat00010

[화학식 6][Chemical Formula 6]

Figure pat00011
Figure pat00011

상기 화학식 3 내지 6에서,In the above formulas 3 to 6,

X1, R1 내지 R10, Ar1은 상기 화학식 1에서 정의된 바와 같다.X 1 , R 1 to R 10, and Ar 1 are as defined in Formula 1 above.

본 발명의 화합물은 하기 예시된 화합물들로 구체화될 수 있다. 그러나 본 발명의 화합물이 하기 예시된 화합물들로 한정되는 것은 아니다.The compounds of the present invention may be embodied by the following exemplified compounds. However, the compounds of the present invention are not limited to the following exemplified compounds.

Figure pat00012
Figure pat00012

Figure pat00013
Figure pat00013

Figure pat00014
Figure pat00014

Figure pat00015
Figure pat00015

Figure pat00016
Figure pat00016

Figure pat00017
Figure pat00017

Figure pat00018
Figure pat00018

Figure pat00019
Figure pat00019

Figure pat00020
Figure pat00020

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

Figure pat00025
Figure pat00025

Figure pat00026
Figure pat00026

Figure pat00027
Figure pat00027

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

Figure pat00041
Figure pat00041

Figure pat00042
Figure pat00042

이러한 본 발명의 화학식 1의 화합물은 하기 합성예를 참조하여 다양하게 합성할 수 있다.
The compounds of formula (I) of the present invention can be synthesized in various ways with reference to the following synthesis examples.

2. 유기 전계 발광 소자2. Organic electroluminescent device

본 발명의 다른 측면은 상기한 본 발명에 따른 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자에 관한 것이다.Another aspect of the present invention relates to an organic electroluminescent device comprising the compound represented by Formula 1 according to the present invention.

구체적으로, 본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 1종 이상 포함하는 유기 전계 발광 소자를 제공한다.More specifically, the present invention provides an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the organic layers includes an organic electric field A light emitting device is provided.

상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있다. 바람직하게는 상기 화학식 1로 표시되는 화합물은 발광층 물질로서 유기 전계 발광 소자에 포함될 수 있다. 이 경우 유기 전계 발광 소자는 발광효율, 휘도, 전력효율, 열적 안정성 및 소자 수명이 향상될 수 있다.The organic material layer containing the compound represented by Formula 1 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. Preferably, the compound represented by Formula 1 may be included in an organic electroluminescent device as a light emitting layer material. In this case, the light emitting efficiency, brightness, power efficiency, thermal stability, and device lifetime of the organic electroluminescent device can be improved.

특히 본 발명의 화학식 1로 표시되는 화합물은 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료인 것이 바람직하며, 발광층의 인광 호스트인 것이 더욱 바람직하다.In particular, the compound represented by the general formula (1) of the present invention is preferably a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, more preferably a phosphorescent host of the light emitting layer.

이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 것일 수 있다. 이때 정공 주입층, 정공 수송층, 전자 수송층 및 발광층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 1종 이상 포함할 수 있다. 상기 전자 수송층 위에는 전자 주입층이 위치할 수도 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode sequentially laminated. At this time, at least one of the hole injecting layer, the hole transporting layer, the electron transporting layer and the light emitting layer may contain at least one compound represented by the above formula (1). An electron injection layer may be disposed on the electron transport layer.

또한 본 발명의 유기 전계 발광 소자는 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조로 이루어질 수도 있다.Also, the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is interposed between the electrode and the organic layer interface.

본 발명의 유기 전계 발광 소자에서 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지는 않는다.In the organic electroluminescent device of the present invention, the organic material layer containing the compound represented by Formula 1 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 소자는 유기물층 중 1층 이상을 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다.The organic electroluminescent device of the present invention is manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that one or more layers of the organic layers are formed so as to include the compound represented by Formula 1 .

예컨대, 기판으로는 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 사용될 수 있다.For example, a silicon wafer, quartz or glass plate, a metal plate, a plastic film or a sheet can be used as the substrate.

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 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에 한정되는 것은 아니다.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 and polyaniline; Or carbon black, but are not limited thereto.

음극 물질로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에 한정되는 것은 아니다.Examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.

정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층으로 사용되는 물질은 당업계에 알려진 통상의 물질이라면 특별히 한정되지 않는다.
The material used for the hole injecting layer, the hole transporting layer, the electron injecting layer and the electron transporting layer is not particularly limited as long as it is a conventional material known in the art.

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 the following examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of the present invention.

[준비예 1] Core1의 합성[Preparation Example 1] Synthesis of Core1

<단계 1> 3H-naphtho[1,2-g]indole의 합성<Step 1> Synthesis of 3H-naphtho [1,2-g] indole

Figure pat00043
Figure pat00043

질소 기류 하에서 1-nitrophenanthrene(20 g, 89.59 mmol)을 800ml THF에 녹인 후 -40℃로 내리고 vinylmagnesium bromide(35.27 g, 268.78 mmol)을 넣는다. 20분 교반 후 포화된 NH4Cl 수용액을 사용하여 반응을 종결시킨 후 에틸아세테이트로 유기층을 분리하여 MgSO4를 사용하여 물을 제거하였다. 물이 제거된 유기층에서 용매를 제거한 후 컬럼 크로마토그래피(Hexane:MC = 5:1 (v/v))로 정제하여 3H-naphtho[1,2-g]indole 12.6g(yield 65 %)을 얻었다.1-Nitrophenanthrene (20 g, 89.59 mmol) is dissolved in 800 ml of THF under a nitrogen stream and then cooled to -40 ° C and vinylmagnesium bromide (35.27 g, 268.78 mmol) is added. After stirring for 20 minutes, the reaction was terminated using saturated aqueous NH 4 Cl. The organic layer was separated with ethyl acetate and the 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 = 5: 1 (v / v)) to obtain 12.6 g of 3H-naphtho [1,2- .

1H-NMR : δ 6.45 (d, 1H), 7.27 (d, 1H), 7.71 (m, 2H), 7.88 (m, 3H), 8.12(d, 1H), 8.93(m, 2H), 11.35(s, 1H) 1 H-NMR: δ 6.45 ( d, 1H), 7.27 (d, 1H), 7.71 (m, 2H), 7.88 (m, 3H), 8.12 (d, 1H), 8.93 (m, 2H), 11.35 ( s, 1 H)

<단계 2> 3-phenyl-3H-naphtho[1,2-g]indole의 합성<Step 2> Synthesis of 3-phenyl-3H-naphtho [1,2-g] indole

Figure pat00044
Figure pat00044

질소 기류 하에서 화합물인 3H-naphtho[1,2-g]indole(12.6g, 57.99mmol), Iodobenzene(17.74g, 86.98mmol), Cu powder(1.9g, 28.99mmol), K2CO3(12g, 86.98mmol) 및 nitrobenzene(200ml)를 혼합하고 190℃에서 12시간 동안 교반하였다. 반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 3-phenyl-3H-naphtho[1,2-g]indole 12.7g (yield: 75 %)을 획득하였다.3H-naphtho the compound in a nitrogen stream [1,2-g] indole (12.6g , 57.99mmol), Iodobenzene (17.74g, 86.98mmol), Cu powder (1.9g, 28.99mmol), K 2 CO 3 (12g, 86.98 mmol) and nitrobenzene (200 ml) were mixed and stirred at 190 占 폚 for 12 hours. After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed, and the residue was purified by column chromatography to obtain 12.7 g (yield: 75%) of 3-phenyl-3H-naphtho [1,2-g] indole.

1H-NMR : δ 6.52 (d, 1H), 6.58 (m, 6H), 7.72 (m, 2H), 7.85 (m, 3H), 8.12(d, 1H), 8.94(m, 2H) One2H), 7.85 (m, 2H), 8.12 (d, 1H), 8.94 (m, 2H)

<단계 3> 9-nitro-3-phenyl-3H-naphtho[1,2-g]indole의 합성<Step 3> Synthesis of 9-nitro-3-phenyl-3H-naphtho [1,2-g] indole

Figure pat00045
Figure pat00045

질소 기류 하에서 화합물인 3-phenyl-3H-naphtho[1,2-g]indole(12.7g, 43.34mmol)를 1,4-dioxane(400ml)에 넣은 후 교반하였다. 15ml의 질산을 24ml의 상수에 희석한 용매에 상기 혼합물을 투입하고 60℃에서 0.5시간 동안 교반하였다. 반응이 종결된 후 400ml의 상수를 가하고 1,4-dioxane을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 9-nitro-3-phenyl-3H-naphtho[1,2-g]indole 8.0g (yield: 55 %)을 획득하였다.3-phenyl-3H-naphtho [1,2-g] indole (12.7 g, 43.34 mmol) was added to 1,4-dioxane (400 ml) under nitrogen flow and stirred. The mixture was added to a solvent in which 15 ml of nitric acid was diluted to 24 ml of a constant water, and the mixture was stirred at 60 ° C for 0.5 hours. After completion of the reaction, a constant of 400 ml was added, 1,4-dioxane was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . The solvent of the organic layer was removed and the residue was purified by column chromatography to obtain 8.0 g (yield: 55%) of 9-nitro-3-phenyl-3H-naphtho [1,2-g] indole.

1H-NMR : δ 6.52 (d, 1H), 6.58 (m, 6H), 7.72 (m, 2H), 7.88 (d, 1H), 8.08(t, 1H), 8.51(d, 1H), 8.89(m, 2H) One(D, 1H), 8.58 (d, 1H), 8.89 (m, 2H), 7.88 , 2H)

<단계 4> Core1의 합성<Step 4> Synthesis of Core1

Figure pat00046
Figure pat00046

질소 기류 하에서 9-nitro-3-phenyl-3H-naphtho[1,2-g]indole(8.0g, 23.66mmol)과 triphenylphosphine(15.4g, 59.15mmol), 1,2-dichlorobenzene(120ml)를 넣은 후 12시간 동안 교반하였다. 반응 종료 후 디스틸레이션을 통해 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층은 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 Core1 4.8g (yield: 66 %)을 획득하였다.(8.0 g, 23.66 mmol), triphenylphosphine (15.4 g, 59.15 mmol) and 1,2-dichlorobenzene (120 ml) were placed in a nitrogen stream under nitrogen atmosphere Stir for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed through distillation and extracted with dichloromethane. The extracted organic layer was dried with MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 4.8 g (yield: 66%) of Core 1 was obtained by column chromatography.

1H-NMR : δ 6.52 (d, 1H), 6.58 (m, 6H), 7.72 (m, 2H), 7.88 (m, 3H), 8.12(d, 1H), 8.51(d, 1H), 11.15(s, 1H)
 One1H), 8.51 (d, 1H), 11.15 (m, 2H), 7.88 (m, 2H) , 1H)

[준비예 2] Core2의 합성[Preparation Example 2] Synthesis of Core2

<단계 1> 8H-naphtho[1,2-f]indole과 1H-naphtho[2,1-e]indole의 합성<Step 1> Synthesis of 8H-naphtho [1,2-f] indole and 1H-naphtho [2,1-e] indole

Figure pat00047
Figure pat00047

1-nitrophenanthrene 대신 2-nitrophenanthrene(30g, 134.39mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 1>과 동일한 과정을 수행하여 8H-naphtho[1,2-f]indole 10.21g (yield 35%), 1H-naphtho[2,1-e]indole 9.34g (yield: 32 %)을 획득하였다. Step 1 of Preparation Example 1 was repeated except that 2-nitrophenanthrene (30 g, 134.39 mmol) was used instead of 1-nitrophenanthrene to obtain 10.21 g of 8H-naphtho [1,2- yield 35%) and 1H-naphtho [2,1-e] indole 9.34 g (yield: 32%).

1H-NMR : δ 6.45 (d, 1H), 7.27 (d, 1H), 7.73 (m, 2H), 7.88 (m, 2H) 7, 8.13(s, 1H), 8.93(m, 2H), 11.22(s, 1H) One(M, 2H), 7.23 (d, IH), 7.73 (m, 2H) s, 1 H)

1H-NMR : δ 6.45 (d, 1H), 7.27 (d, 1H), 7.72 (m, 2H), 7.85 (d, 1H), 8.13(d, 1H), 8.98(m, 2H) 11.25(s, 1H) One(M, 2H), 7.25 (d, IH), 7.72 (d, IH), 7.85 1H)

<단계 2> 8-phenyl-8H-naphtho[1,2-f]indole의 합성<Step 2> Synthesis of 8-phenyl-8H-naphtho [1,2-f] indole

Figure pat00048
Figure pat00048

3H-naphtho[1,2-g]indole 대신 8H-naphtho[1,2-f]indole(10.21g, 47.05mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 2>와 동일한 과정을 수행하여 8-phenyl-8H-naphtho[1,2-f]indole 8.5g (yield: 62 %)을 획득하였다. Except that 8H-naphtho [1,2-f] indole (10.21 g, 47.05 mmol) was used instead of 3H-naphtho [1,2-g] indole in Step 2 of Preparation Example 1 To obtain 8.5 g (yield: 62%) of 8-phenyl-8H-naphtho [1,2-f] indole.

1H-NMR : δ 6.52 (d, 1H), 7.60 (m, 6H), 7.74 (m, 2H), 7.85 (m, 2H) 8.12(m, 2H), 8.95(m, 2H) One2H), 8.95 (m, 2H), 7.85 (m, 2H), 7.85 (m,

<단계 3> 1-nitro-8-phenyl-8H-naphtho[1,2-f]indole의 합성<Step 3> Synthesis of 1-nitro-8-phenyl-8H-naphtho [1,2-f] indole

Figure pat00049
Figure pat00049

3-phenyl-3H-naphtho[1,2-g]indole 대신 8-phenyl-8H-naphtho[1,2-f]indole(8.5g, 29.01mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 3>과 동일한 과정을 수행하여 1-nitro-8-phenyl-8H-naphtho[1,2-f]indole 5.0g (yield: 52 %)을 획득하였다. Preparation Example 1] was repeated except that 8-phenyl-8H-naphtho [1,2-f] indole (8.5 g, 29.01 mmol) was used instead of 3-phenyl-3H-naphtho [ (Yield: 52%) of 1-nitro-8-phenyl-8H-naphtho [1,2-f] indole was obtained.

1H-NMR : δ 6.52 (m, 3H), 7.58 (m, 6H), 7.69 (m, 2H), 7.85 (m, 2H) 8.10(m, 2H), 8.51(d, 1H), 8.81(d, 1H) 8.95(s, 1H) One(M, 2H), 8.51 (d, 1H), 8.81 (m, 2H), 7.85 (m, 2H) 1H) 8.95 (s, 1 H)

<단계 4> Core2의 합성<Step 4> Synthesis of Core2

Figure pat00050
Figure pat00050

9-nitro-3-phenyl-3H-naphtho[1,2-g]indole 대신 1-nitro-8-phenyl-8H-naphtho[1,2-f]indole(5.0g, 14.79mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 4>와 동일한 과정을 수행하여 Core2 2.7g (yield: 61 %)을 획득하였다. Except that 1-nitro-8-phenyl-8H-naphtho [1,2-f] indole (5.0 g, 14.79 mmol) was used instead of 9-nitro-3-phenyl-3H-naphtho [ (Yield: 61%) was obtained by performing the same procedure as in [Step 4] of [Preparation Example 1].

1H-NMR : δ 6.48 (d, 1H), 7.55 (m, 6H), 7.73 (m, 2H), 7.88 (m, 2H) 8.13(m, 2H), 11.18(s, 1H)
 One2H), 8.18 (s, IH), 7.38 (d, IH)

[준비예 3] Core3의 합성[Preparation Example 3] Synthesis of Core 3

<단계 1> 1-phenyl-1H-naphtho[2,1-e]indole의 합성<Step 1> Synthesis of 1-phenyl-1H-naphtho [2,1-e] indole

Figure pat00051
Figure pat00051

3H-naphtho[1,2-g]indole 대신 1H-naphtho[2,1-e]indole(9.34g, 43.04mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 2>와 동일한 과정을 수행하여 1-phenyl-1H-naphtho[2,1-e]indole 8.57g (yield: 68 %)을 획득하였다. Step 2 of Preparation Example 1 was repeated except that 1H-naphtho [2,1-e] indole (9.34 g, 43.04 mmol) was used instead of 3H-naphtho [1,2- To obtain 8.57 g (yield: 68%) of 1-phenyl-1H-naphtho [2,1-e] indole.

1H-NMR : δ 6.52 (s, 3H) 7.60 (m, 6H), 7.15 (m, 2H), 7.88 (m, 3H) 8.13(d, 1H), 8.92(m, 2H) One2H), 7.88 (m, 3H) 8.13 (d, IH), 8.92 (m, 2H)

<단계 2> 9-nitro-1-phenyl-1H-naphtho[2,1-e]indole의 합성<Step 2> Synthesis of 9-nitro-1-phenyl-1H-naphtho [2,1-e] indole

Figure pat00052
Figure pat00052

3-phenyl-3H-naphtho[1,2-g]indole 대신 1-phenyl-1H-naphtho[2,1-e]indole(8.57g, 29.26mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 3>과 동일한 과정을 수행하여 9-nitro-1-phenyl-1H-naphtho[2,1-e]indole 5.2g (yield: 53 %)을 획득하였다. Preparation Example 1] was repeated except that 1-phenyl-1H-naphtho [2,1-e] indole (8.57 g, 29.26 mmol) was used instead of 3-phenyl-3H-naphtho [ (Yield: 53%) of 9-nitro-1-phenyl-1H-naphtho [2,1-e] indole was obtained.

1H-NMR : δ 6.50 (d, 1H) 7.55 (m, 6H), 7.72 (m, 2H), 7.88 (d, 1H) 8.08(t, 1H), 8.52(d, 1H), 8.92(m, 2H) One(D, IH), 8.52 (d, IH), 8.92 (m, 2H), 7.88 )

<단계 3> Core3의 합성<Step 3> Synthesis of Core 3

Figure pat00053
Figure pat00053

9-nitro-3-phenyl-3H-naphtho[1,2-g]indole 대신 9-nitro-1-phenyl-1H-naphtho[2,1-e]indole(5.2g, 15.51mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 4>와 동일한 과정을 수행하여 Core3 2.9g (yield: 62 %)을 획득하였다. Phenyl-1H-naphtho [2,1-e] indole (5.2 g, 15.51 mmol) was used instead of 9-nitro-3-phenyl-3H-naphtho [ , And 2.9 g (yield: 62%) of Core 3 was obtained by performing the same procedure as in [Step 4] of [Preparation Example 1].

1H-NMR : δ 6.52 (d, 1H) 7.58 (m, 6H), 7.72 (m, 2H), 7.88 (m, 2H) 8.11(d, 1H), 11.12(s, 1H)
 One(D, IH), 11.12 (s, IH), 7.72 (m, 2H)

[준비예 4] Core4의 합성[Preparation Example 4] Synthesis of Core 4

<단계 1> (E)-2-(2-(naphthalen-1-yl)vinyl)thiophene의 합성<Step 1> Synthesis of (E) -2- (2- (naphthalen-1-yl) vinyl) thiophene

Figure pat00054
Figure pat00054

질소 기류 하에서 (E)-1-(2-bromovinyl)naphthalene(20g, 85.83mmol), thiophen-2-ylboronic acid(13g, 102.99mmol), K2CO3(35.5g, 257.49mmol), 400ml/100ml의 THF/H2O를 넣고 교반하였다. 40℃에서 Pd(PPh3)4(2.97g, 2.57mmol)를 넣고 80℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 (E)-2-(2-(naphthalen-1-yl)vinyl)thiophene 16.4g (yield: 81 %)을 획득하였다.(E) -1- (2-bromovinyl) naphthalene (20 g, 85.83 mmol), thiophen-2-ylboronic acid (13 g, 102.99 mmol), K 2 CO 3 (35.5 g, 257.49 mmol) Of THF / H 2 O were added and stirred. Pd (PPh 3) at 40 ℃ into the 4 (2.97g, 2.57mmol) and stirred under reflux at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 16.4 g (yield: 81%) of (E) -2- (2- (naphthalen-1-yl) vinyl) thiophene was obtained by column chromatography.

1H-NMR : δ 6.95 (m, 3H) 7.17 (t, 1H), 7.52(m, 3H), 7.69 (d, 1H) 7.78(d, 1H), 7.96(m, 2H), 8.08(d, 1H) One7.88 (d, IH), 7.96 (m, 2H), 8.08 (d, IH) )

<단계 2> phenanthro[1,2-b]thiophene의 합성<Step 2> Synthesis of phenanthro [1,2-b] thiophene

Figure pat00055
Figure pat00055

질소 기류 하에서 (E)-2-(2-(naphthalen-1-yl)vinyl)thiophene(16.4g, 69.39mmol), Iodine(18.11g, 138.78 mmol), 300ml의 cyclohexane을 넣고 80℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 phenanthro[1,2-b]thiophene 10.7g (yield: 66 %)을 획득하였다.Iodine (18.11 g, 138.78 mmol) and 300 ml of cyclohexane were added to the flask under nitrogen atmosphere at 80 ° C. for 12 hours And the mixture was refluxed and stirred. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and 10.7 g (yield: 66%) of phenanthro [1,2-b] thiophene was obtained by column chromatography.

1H-NMR : δ 7.75 (m, 7H), 8.12 (d, 1H), 8.93 (m, 2H) One1H-NMR:? 7.75 (m, 7H), 8.12 (d, 1H), 8.93

<단계 3> 9-nitrophenanthro[1,2-b]thiophene의 합성<Step 3> Synthesis of 9-nitrophenanthro [1,2-b] thiophene

Figure pat00056
Figure pat00056

3-phenyl-3H-naphtho[1,2-g]indole 대신 phenanthro[1,2-b]thiophene(10.7g, 45.66mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 3>과 동일한 과정을 수행하여 목적 화합물인 9-nitrophenanthro[1,2-b]thiophene 6.7g (yield: 53 %)을 획득하였다. Step 3 of Preparation Example 1] was repeated except that phenanthro [1,2-b] thiophene (10.7 g, 45.66 mmol) was used instead of 3-phenyl-3H-naphtho [ The same procedure was carried out to obtain 6.7 g (yield: 53%) of 9-nitrophenanthro [1,2-b] thiophene as a target compound.

1H-NMR : δ 7.72 (m, 4H), 7.88 (d, 1H), 8.52 (d, 1H), 8.82 (d, 1H) 8.95(d, 1H) One8.95 (d, IH), 8.82 (d, IH), 8.82 (d,

<단계 4> Core4의 합성<Step 4> Synthesis of Core4

Figure pat00057
Figure pat00057

9-nitro-3-phenyl-3H-naphtho[1,2-g]indole 대신 9-nitrophenanthro[1,2-b]thiophene(6.7g, 24.01mmol)을 사용하는 것을 제외하고는 [준비예 1]의 <단계 4>와 동일한 과정을 수행하여 Core4 3.8g (yield: 64 %)을 획득하였다. Preparation Example 1] was repeated except that 9-nitrophenanthro [1,2-b] thiophene (6.7 g, 24.01 mmol) was used instead of 9-nitro-3-phenyl-3H- (Yield: 64%) was obtained by performing the same process as that of < Step 4 >.

1H-NMR : δ 7.71 (m, 7H), 8.15 (d, 1H), 11.18 (s, 1H)
 One1H-NMR:? 7.71 (m, 7H), 8.15 (d, 1H), 11.18

[준비예 5] Core5의 합성[Preparation Example 5] Synthesis of Core 5

<단계 1(E)-2-(2-(naphthalen-1-yl)vinyl)furan의 합성Step 1 Synthesis of (E) -2- (2- (naphthalen-1-yl) vinyl) furan

Figure pat00058
Figure pat00058

thiophen-2-ylboronic acid 대신 furan-2-ylboronic acid(11.4g, 102.99mmol)을 사용하는 것을 제외하고는 [준비예 4]의 <단계 1>과 동일한 과정을 수행하여 (E)-2-(2-(naphthalen-1-yl)vinyl)furan 13.6g (yield: 72 %)을 획득하였다. (E) -2- (4-fluorophenyl) -2-methyl-thiophene-2-ylboronic acid was obtained in the same manner as [Step 1] of [Preparation Example 4], except that furan- (Yield: 72%) of 2- (naphthalen-1-yl) vinyl) furan.

1H-NMR : δ 6.52 (d, 1H), 6.95 (m, 3H), 7.55 (m, 3H), 7.78(m, 2H), 7.96(m, 2H), 8.10(d, 1H) One2H), 7.96 (m, 2H), 8.10 (d, IH), 7.55 (m,

<단계 2> 13-nitrodibenzo[b,mn]xanthene의 합성<Step 2> Synthesis of 13-nitrodibenzo [b, mn] xanthene

Figure pat00059
Figure pat00059

(E)-2-(2-(naphthalen-1-yl)vinyl)thiophene 대신 (E)-2-(2-(naphthalen-1-yl)vinyl)furan(13.6g, 61.80mmol)을 사용하는 것을 제외하고는 [준비예 4]의 <단계 2>과 동일한 과정을 수행하여 13-nitrodibenzo[b,mn]xanthene 7.8g (yield: 58 %)을 획득하였다. (E) -2- (2- (naphthalen-1-yl) vinyl) furan (13.6 g, 61.80 mmol) was used instead of (E) -2- (Yield: 58%) of 13-nitrodibenzo [b, mn] xanthene was obtained in the same manner as in [Step 2] of [Preparation Example 4].

1H-NMR : δ 6.66 (d, 1H), 7.52 (d, 1H), 7.74 (m, 2H), 7.86(m, 3H), 8.14(d, 1H), 8.96(m, 2H) One2H), 7.86 (m, 3H), 8.14 (d, IH), 8.96 (m, 2H)

<단계 3> 9-nitrophenanthro[1,2-b]furan의 합성<Step 3> Synthesis of 9-nitrophenanthro [1,2-b] furan

Figure pat00060
Figure pat00060

phenanthro[1,2-b]thiophene 대신 13-nitrodibenzo[b,mn]xanthene(7.8g, 35.77mmol)을 사용하는 것을 제외하고는 [준비예 4]의 <단계 3>와 동일한 과정을 수행하여 9-nitrophenanthro[1,2-b]furan 4.5g (yield: 48 %)을 획득하였다. Step 3 of Preparation Example 4 was repeated except that 13-nitrodibenzo [b, mn] xanthene (7.8 g, 35.77 mmol) was used instead of phenanthro [1,2- b] thiophene to obtain 9 -nitrophenanthro [l, 2-b] furan (yield: 48%).

1H-NMR : δ 6.66 (d, 1H), 7.52 (d, 1H), 7.74 (m, 2H), 7.88(d, 1H), 8.11(t, 1H), 8.53(d, 1H), 8.82 (d, 1H), 8.95(d, 1H) One1H), 8.52 (d, 1H), 8.82 (d, 1H), 7.84 (d, , &Lt; / RTI &gt; 1H), 8.95 (d, 1H)

<단계 4> Core5의 합성<Step 4> Synthesis of Core5

Figure pat00061
Figure pat00061

9-nitrophenanthro[1,2-b]thiophene 대신 9-nitrophenanthro[1,2-b]furan(4.5g, 17.17mmol)을 사용하는 것을 제외하고는 [준비예 4]의 <단계 4>와 동일한 과정을 수행하여 Core5 2.5g (yield: 63 %)을 획득하였다. Step 4 of Preparation Example 4 was repeated except that 9-nitrophenanthro [1,2-b] furan (4.5 g, 17.17 mmol) was used in place of 9-nitrophenanthro [1,2- b] thiophene To obtain Core5 2.5 g (yield: 63%).

1H-NMR : δ 6.68 (d, 1H), 7.55 (d, 1H), 7.72 (m, 2H), 7.85(m, 3H), 8.12(d, 1H), 11.13(s, 1H)
 One(D, IH), 7.72 (m, 2H), 7.85 (m, 3H), 8.12

[합성예 1] Inv 88의 합성[Synthesis Example 1] Synthesis of Inv 88

Figure pat00062
Figure pat00062

질소 기류 하에서 Core1(3.0g, 9.79mmol), 4-chloro-2-phenylpyrimidine(2.24g, 11.75mmol), Pd(OAc)2(0.1g, 0.48mmol), NaO(t-bu)(2.82g, 29.37mmol), P(t-bu)3(0.39g, 1.95mmol) 및 Toluene(80ml)을 혼합한 다음, 110℃에서 12시간 동안 교반하였다. 반응이 종결된 후 에틸아세테이트로 추출한 다음, MgSO4로 수분을 제거하고, 컬럼크로마토그래피로 정제하여 목적 화합물인 Inv 88 (2.5g, 수율 57%)을 얻었다.Pd (OAc) 2 (0.1 g, 0.48 mmol), NaO (t-bu) (2.82 g, 0.78 mmol), 4-chloro-2-phenylpyrimidine (2.24 g, 11.75 mmol) 29.37 mmol), P (t-bu) 3 (0.39 g, 1.95 mmol) and Toluene (80 ml) were mixed and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the residue was purified by column chromatography using MgSO 4 to obtain Inv 88 (2.5 g, yield 57%).

GC-Mass (이론치: 460.53 g/mol, 측정치: 460 g/mol)
GC-Mass (theory: 460.53 g / mol, measurement: 460 g / mol)

[합성예 2] Inv 106의 합성[Synthesis Example 2] Synthesis of Inv 106

Figure pat00063
Figure pat00063

질소 기류 하에서 Core1(3.0g, 9.79mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine(3.1g, 11.74mmol), NaH(0.39g, 9.79mmol) 및 DMF(80ml)를 혼합하고 상온에서 3시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후, 컬럼크로마토그래피로 정제하여 목적 화합물인 Inv 106 (3.5g, 수율 67%)를 얻었다. (3.0 g, 9.79 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.1 g, 11.74 mmol), NaH (0.39 g, 9.79 mmol) and DMF (80 ml) Were mixed and stirred at room temperature for 3 hours. After completion of the reaction, water was added thereto, and the solid compound was filtered and purified by column chromatography to obtain the title compound Inv 106 (3.5 g, yield 67%).

GC-Mass (이론치: 537.61 g/mol, 측정치: 537 g/mol)
GC-Mass (calculated: 537.61 g / mol, measured: 537 g / mol)

[합성예 3] Inv 107의 합성[Synthesis Example 3] Synthesis of Inv 107

Figure pat00064
Figure pat00064

4-chloro-2-phenylpyrimidine 대신 4-chloro-2,6-diphenylpyrimidine(3.13g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 107 (3.3g, 수율 63%)을 얻었다. The procedure of Synthesis Example 1 was repeated except that 4-chloro-2,6-diphenylpyrimidine (3.13 g, 11.74 mmol) was used instead of 4-chloro-2-phenylpyrimidine to obtain the target compound Inv 107 63%).

GC-Mass (이론치: 536.62 g/mol, 측정치: 536 g/mol)
GC-Mass (calculated: 536.62 g / mol, measured: 536 g / mol)

[합성예 4] Inv 141의 합성[Synthesis Example 4] Synthesis of Inv 141

Figure pat00065
Figure pat00065

4-chloro-2-phenylpyrimidine 대신 4-(4-chlorophenyl)-2,6-diphenylpyrimidine(4.02g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 141(3.6g, 수율 61%)를 얻었다. The procedure of Synthesis Example 1 was repeated except that 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (4.02 g, 11.74 mmol) was used instead of 4-chloro-2- 3.6 g, yield: 61%).

GC-Mass (이론치: 612.72 g/mol, 측정치: 612 g/mol)
GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[합성예 5] Inv 168의 합성[Synthesis Example 5] Synthesis of Inv 168

Figure pat00066
Figure pat00066

4-chloro-2-phenylpyrimidine 대신 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine(4.03g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 168(3.6g, 수율 60%)을 얻었다. The same procedure as in Synthesis Example 1 was carried out except that 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.03 g, 11.74 mmol) was used in place of 4-chloro-2-phenylpyrimidine To obtain Inv 168 (3.6 g, yield 60%) as a target compound.

GC-Mass (이론치: 613.71 g/mol, 측정치: 613 g/mol)
GC-Mass (theory: 613.71 g / mol, measured: 613 g / mol)

[합성예 6] Inv 199의 합성[Synthesis Example 6] Synthesis of Inv 199

Figure pat00067
Figure pat00067

4-chloro-2-phenylpyrimidine 대신 4-(2-chloropyrimidin-4-yl)benzonitrile(2.53g, 11.74mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 199(2.9g, 수율 62%)을 얻었다. The same procedure as in Synthesis Example 1 was carried out except that 4- (2-chloropyrimidin-4-yl) benzonitrile (2.53 g, 11.74 mmol) was used in place of 4-chloro-2-phenylpyrimidine to obtain the desired compound Inv 199 g, yield: 62%).

GC-Mass (이론치: 485.54 g/mol, 측정치: 485 g/mol)
GC-Mass (calculated: 485.54 g / mol, measured: 485 g / mol)

[합성예 7] Inv 223의 합성[Synthesis Example 7] Synthesis of Inv 223

Figure pat00068
Figure pat00068

Core1 대신 Core2(3g, 9.79mmol)을 사용하고, 4-chloro-2-phenylpyrimidine 대신 2-(3-chlorophenyl)-4-phenylpyrimidine(3.13g, 11.74mmol)을 사용한 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 223(3.0g, 수율 58%)을 얻었다. The same procedure as in Synthesis Example 1 was carried out except that Core 2 (3 g, 9.79 mmol) was used instead of Core 1 and 2- (3-chlorophenyl) -4-phenylpyrimidine (3.13 g, 11.74 mmol) was used in place of 4-chloro-2- Was performed to obtain Inv 223 (3.0 g, yield 58%) as a target compound.

GC-Mass (이론치: 536.62 g/mol, 측정치: 536 g/mol)
GC-Mass (calculated: 536.62 g / mol, measured: 536 g / mol)

[합성예 8] Inv 225 의 합성[Synthesis Example 8] Synthesis of Inv 225

Figure pat00069
Figure pat00069

질소 기류 하에서 Core2(3.0g, 9.79mmol), 4-bromo-N,N-diphenylaniline(3.8g, 11.74mmol), Cu powder(0.31g, 4.89mmol), K2CO3(2.02g, 14.68mmol), 및 nitrobenzene(80ml)를 혼합하고 190℃에서 12시간 동안 교반하였다. 반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 Inv 225(3.5g, 수율 65%)을 얻었다.Core2 conducted in a nitrogen atmosphere (3.0g, 9.79mmol), 4- bromo-N, N-diphenylaniline (3.8g, 11.74mmol), Cu powder (0.31g, 4.89mmol), K 2 CO 3 (2.02g, 14.68mmol) , And nitrobenzene (80 ml) were mixed and stirred at 190 占 폚 for 12 hours. After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removal of the organic layer solvent, the residue was purified by column chromatography to give the desired compound Inv 225 (3.5 g, yield 65%).

GC-Mass (이론치: 549.66 g/mo, 측정치: 549 g/mol)
GC-Mass (calculated: 549.66 g / mol, measured: 549 g / mol)

[합성예 9] Inv 232의 합성[Synthesis Example 9] Synthesis of Inv 232

Figure pat00070
Figure pat00070

4-bromo-N,N-diphenylaniline 대신 2-bromo-4,6-diphenylpyridine (3.64g, 11.74mmol)를 사용하는 것을 제외하고는 합성예 8과 동일한 과정을 수행하여 목적 화합물인 Inv 232 (3.3g, 수율 63%)를 얻었다. Except that 2-bromo-4,6-diphenylpyridine (3.64 g, 11.74 mmol) was used in place of 4-bromo-N, N-diphenylaniline , Yield: 63%).

GC-Mass (이론치: 535.64 g/mol, 측정치: 535 g/mol)
GC-Mass (calculated: 535.64 g / mol, measured: 535 g / mol)

[합성예 10] Inv 233의 합성[Synthesis Example 10] Synthesis of Inv 233

Figure pat00071
Figure pat00071

4-bromo-N,N-diphenylaniline 대신 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine(4.5g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 8과 동일한 과정을 수행하여 목적 화합물인 Inv 233(3.8g, 수율 64%)을 얻었다. (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.5 g, 11.74 mmol) was used in place of 4-bromo-N, N-diphenylaniline (Inv 233, 3.8 g, yield 64%) was obtained.

GC-Mass (이론치: 613.71 g/mol, 측정치: 613 g/mol)
GC-Mass (theory: 613.71 g / mol, measured: 613 g / mol)

[합성예 11] Inv 253의 합성[Synthesis Example 11] Synthesis of Inv 253

Figure pat00072
Figure pat00072

4-bromo-N,N-diphenylaniline 대신 9-(4-bromophenyl)-9H-carbazole(3.78g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 8과 동일한 과정을 수행하여 목적 화합물인 Inv 253(3.3g, 수율 62%)을 얻었다. Except that 9- (4-bromophenyl) -9H-carbazole (3.78 g, 11.74 mmol) was used in place of 4-bromo-N, N-diphenylaniline to obtain the target compound Inv 253 3.3 g, yield 62%).

GC-Mass (이론치: 547.65 g/mol, 측정치: 547 g/mol)
GC-Mass (calculated: 547.65 g / mol, measured: 547 g / mol)

[합성예 12] Inv 274의 합성[Synthesis Example 12] Synthesis of Inv 274

Figure pat00073
Figure pat00073

Core2 대신 Core3(3.0g 9.79mmol)을 사용하고 4-bromo-N,N-diphenylaniline 대신 2-bromo-4,6-diphenylpyrimidine(3.6g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 8과 동일한 과정을 수행하여 목적 화합물인 Inv 274(3.46 g, 수율 66%)을 얻었다. Was obtained in the same manner as in Synthesis Example 8, except that Core 3 (3.0 g, 9.79 mmol) was used in place of Core 2 and 2-bromo-4,6-diphenylpyrimidine (3.6 g, 11.74 mmol) was used in place of 4-bromo-N, N-diphenylaniline. Was performed to obtain Inv 274 (3.46 g, yield 66%) as a target compound.

GC-Mass (이론치: 536.62 g/mol, 측정치: 536 g/mol)
GC-Mass (calculated: 536.62 g / mol, measured: 536 g / mol)

[합성예 13] Inv 278의 합성[Synthesis Example 13] Synthesis of Inv 278

Figure pat00074
Figure pat00074

Core1 대신 Core3(3.0g, 9.79mmol)을 사용하고, 4-chloro-2-phenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-(4-chlorophenyl)-1,3,5-triazine(5.82g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 278 (4.5 g, 수율 60%)을 얻었다. Instead of Core 1, Core 3 (3.0 g, 9.79 mmol) was used and 2,4-di (biphenyl-3-yl) -6- (4-chlorophenyl) -1,3,5-triazine (4.5 g, yield 60%) was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound (5.82 g, 11.74 mmol) was used.

GC-Mass (이론치: 765.9 g/mol, 측정치: 765 g/mol)
GC-Mass (calculated: 765.9 g / mol, measured: 765 g / mol)

[합성예 14] Inv 284의 합성[Synthesis Example 14] Synthesis of Inv 284

Figure pat00075
Figure pat00075

2,4-di(biphenyl-3-yl)-6-(4-chlorophenyl)-1,3,5-triazine 대신 4-(3-chlorophenyl)-2,6-diphenylpyrimidine(4.02g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 13과 동일한 과정을 수행하여 목적 화합물인 Inv 284(3.4g, 수율 57%)를 얻었다. 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.02 g, 11.74 mmol) instead of 2,4-di (biphenyl-3-yl) -6- The procedure of Synthesis Example 13 was repeated to obtain Inv 284 (3.4 g, yield 57%) as a target compound.

GC-Mass (이론치: 612.72 g/mol, 측정치: 612 g/mol)
GC-Mass (calculated: 612.72 g / mol, measured: 612 g / mol)

[합성예 15] Inv 364의 합성[Synthesis Example 15] Synthesis of Inv 364

Figure pat00076
Figure pat00076

Core1 대신 Core4(3.0g, 12.13mmol)를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Inv 364(3.3g, 수율 58%)을 얻었다. The same procedure as in Synthesis Example 2 was carried out except that Core 4 (3.0 g, 12.13 mmol) was used instead of Core 1 to obtain Inv 364 (3.3 g, yield 58%) as a target compound.

GC-Mass (이론치: 478.57 g/mol, 측정치: 478 g/mol)
GC-Mass (calculated: 478.57 g / mol, measured: 478 g / mol)

[합성예 16] Inv 376의 합성[Synthesis Example 16] Synthesis of Inv 376

Figure pat00077
Figure pat00077

Core2 대신 Core4(3.0g, 12.13mmol)를 사용하고, 4-bromo-N,N-diphenylaniline 대신 2-(5-bromobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine(6.75g, 14.55mmol)을 사용하는 것을 제외하고는 합성예 8과 동일한 과정을 수행하여 목적 화합물인 Inv 376 (4.9 g, 수율 62%)을 얻었다. Except that Core 4 (3.0 g, 12.13 mmol) was used instead of Core 2 and 2- (5-bromobiphenyl-3-yl) -4,6-diphenyl-1,3,5-triazine 6.75 g, 14.55 mmol) was used in place of the compound obtained in Synthesis Example 8 to obtain the target compound Inv 376 (4.9 g, yield 62%).

GC-Mass (이론치: 630.76 g/mol, 측정치: 630 g/mol)
GC-Mass (calculated: 630.76 g / mol, measured: 630 g / mol)

[합성예 17] Inv 373의 합성[Synthesis Example 17] Synthesis of Inv 373

Figure pat00078
Figure pat00078

Core1 대신 Core4(3.0g, 12.13mmol)를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Inv 373(3.8g, 수율 57%)을 얻었다. The procedure of Synthesis Example 5 was repeated except that Core 4 (3.0 g, 12.13 mmol) was used instead of Core 1, to obtain the target compound Inv 373 (3.8 g, yield 57%).

GC-Mass (이론치: 554.66 g/mol, 측정치: 554 g/mol)
GC-Mass (calculated: 554.66 g / mol, measured: 554 g / mol)

[합성예 18] Inv 451의 합성[Synthesis Example 18] Synthesis of Inv 451

Figure pat00079
Figure pat00079

Core1 대신 Core5(3.0g, 12.97mmol)를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Inv 451(3.5g, 수율 59%)을 얻었다. The procedure of Synthesis Example 3 was repeated, except that Core 5 (3.0 g, 12.97 mmol) was used instead of Core 1 to obtain the target compound Inv 451 (3.5 g, yield 59%).

GC-Mass (이론치: 461.51 g/mol, 측정치: 461 g/mol)
GC-Mass (calculated: 461.51 g / mol, measured: 461 g / mol)

[합성예 19] Inv 455의 합성[Synthesis Example 19] Synthesis of Inv 455

Figure pat00080
Figure pat00080

4-chloro-2,6-diphenylpyrimidine 대신 2-(4-chlorophenyl)-4,6-di(naphthalen-2-yl)-1,3,5-triazine(6.89g, 15.56mmol)을 사용하는 것을 제외하고는 합성예 18과 동일한 과정을 수행하여 목적 화합물인 Inv 455(4.8g, 수율 58%)을 얻었다. Except using 2- (4-chlorophenyl) -4,6-di (naphthalen-2-yl) -1,3,5-triazine (6.89 g, 15.56 mmol) instead of 4-chloro-2,6-diphenylpyrimidine , The target compound Inv 455 (4.8 g, yield: 58%) was obtained in the same manner as in Synthesis Example 18.

GC-Mass (이론치: 587.67 g/mol, 측정치: 587 g/mol)
GC-Mass (calculated: 587.67 g / mol, measured: 587 g / mol)

[합성예 20] Inv 467의 합성[Synthesis Example 20] Synthesis of Inv 467

Figure pat00081
Figure pat00081

Core2 대신 Core5(3.0g, 12.97mmol)를 사용하고 4-bromo-N,N-diphenylaniline 대신 4'-bromobiphenyl-3,5-dicarbonitrile(4.4g, 15.56mmol)을 사용하는 것을 제외하고는 합성예 8과 동일한 과정을 수행하여 목적 화합물인 Inv 467(3.5g, 수율 62%)을 얻었다. Except that Core 5 (3.0 g, 12.97 mmol) was used in place of Core 2 and 4'-bromobiphenyl-3,5-dicarbonitrile (4.4 g, 15.56 mmol) was used in place of 4-bromo-N, N-diphenylaniline. (Inv 467) (3.5 g, yield 62%) was obtained.

GC-Mass (이론치: 433.46 g/mol, 측정치: 433 g/mol)
GC-Mass (calculated: 433.46 g / mol, measured: 433 g / mol)

[합성예 21] Inv 212의 합성[Synthesis Example 21] Synthesis of Inv 212

Figure pat00082
Figure pat00082

4-chloro-2-phenylpyrimidine 대신 2-chloro-4-phenylquinazoline (2.82g, 11.75mmol)을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 212 (3.0g, 수율 61%)을 얻었다. Except that 2-chloro-4-phenylquinazoline (2.82 g, 11.75 mmol) was used in place of 4-chloro-2-phenylpyrimidine to obtain the desired compound Inv 212 (3.0 g, yield 61% ).

GC-Mass (이론치: 510.59 g/mol, 측정치: 510 g/mol)
GC-Mass (calculated: 510.59 g / mol, measured: 510 g / mol)

[합성예 22] Inv 216의 합성[Synthesis Example 22] Synthesis of Inv 216

Figure pat00083
Figure pat00083

4-chloro-2-phenylpyrimidine 대신 2-chloro-4-(4-(naphthalen-1-yl)phenyl)quinazoline(4.3g, 11.75mmol)를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv 216(3.4g, 수율 55%)을 얻었다. The same procedure as in Synthesis Example 1 was carried out except that 2-chloro-4- (4- (naphthalen-1-yl) phenyl) quinazoline (4.3 g, 11.75 mmol) was used in place of 4-chloro-2- The target compound Inv 216 (3.4 g, yield 55%) was obtained.

GC-Mass (이론치: 636.74 g/mol, 측정치: 636 g/mol)
GC-Mass (calculated: 636.74 g / mol, measured: 636 g / mol)

[합성예 23] Inv 293의 합성[Synthesis Example 23] Synthesis of Inv 293

Figure pat00084
Figure pat00084

2,4-di(biphenyl-3-yl)-6-(4-chlorophenyl)-1,3,5-triazine 대신 2-chloro-4-(4-(naphthalen-2-yl)phenyl)quinazoline(4.3g, 11.74mmol)을 사용하는 것을 제외하고는 합성예 13과 동일한 과정을 수행하여 목적 화합물인 Inv 293 (3.5 g, 수율 57%)을 얻었다. 2-chloro-4- (4- (naphthalen-2-yl) phenyl) quinazoline (4.3) instead of 2,4-di (biphenyl-3- g, 11.74 mmol), the title compound was obtained as a white solid. The title compound, Inv 293 (3.5 g, yield 57%) was obtained.

GC-Mass (이론치: 636.74 g/mol, 측정치: 636 g/mol)
GC-Mass (calculated: 636.74 g / mol, measured: 636 g / mol)

[합성예 24] Inv 383의 합성[Synthesis Example 24] Synthesis of Inv 383

Figure pat00085
Figure pat00085

2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine 대신 4-(biphenyl-4-yl)-2-chloroquinazoline(3.84g, 12.13mmol)를 사용하는 것을 제외하고는 합성예 17과 동일한 과정을 수행하여 목적 화합물인 Inv 383(3.3g, 수율 52%)을 얻었다. Synthesis was carried out except that 4- (biphenyl-4-yl) -2-chloroquinazoline (3.84 g, 12.13 mmol) was used instead of 2- (3-chlorophenyl) -4,6- diphenyl- The procedure of Example 17 was repeated to obtain Inv 383 (3.3 g, yield 52%) as a target compound.

GC-Mass (이론치: 527.64 g/mol, 측정치: 527 g/mol)
GC-Mass (calculated: 527.64 g / mol, measured: 527 g / mol)

[실시예 1 내지 20] 녹색 유기 전계 발광 소자의 제조[Examples 1 to 20] Preparation of green organic electroluminescent device

상기 합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 소자를 제조하였다.The compound synthesized in the above Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and a 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 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)/ 90% 합성예 1 내지 20 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.
10 nm Ir (ppy) 3 (30 nm) / BCP (10 nm) of m-MTDATA (60 nm) / TCTA (80 nm) / 90% compounds of each of Synthetic Examples 1 to 20 on an ITO transparent substrate (electrode) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in this order.

[비교예 1] 녹색 유기 전계 발광 소자의 제조[Comparative Example 1] Production of green organic electroluminescent device

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

실시예 1 내지 20 및 비교예 1에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, BCP 및 CBP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , BCP and CBP used in Examples 1 to 20 and Comparative Example 1 are as follows.

Figure pat00086
Figure pat00086

Figure pat00087

Figure pat00087

[평가예 1][Evaluation Example 1]

실시예 1 내지 20 및 비교예 1에서 제조한 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압, 전류효율 및 발광피크를 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 the green organic electroluminescent devices prepared in Examples 1 to 20 and Comparative Example 1, and the results are shown in Table 1 below.

샘플Sample 호스트Host 구동 전압(V)The driving voltage (V) 발광피크(nm)Emission peak (nm) 전류효율(cd/A)Current efficiency (cd / A) 실시예 1Example 1 Inv-88Inv-88 6.416.41 516516 41.241.2 실시예 2Example 2 Inv-106Inv-106 6.576.57 517517 42.342.3 실시예 3Example 3 Inv-107Inv-107 6.446.44 516516 43.543.5 실시예 4Example 4 Inv-141Inv-141 6.736.73 514514 45.645.6 실시예 5Example 5 Inv-168Inv-168 6.676.67 517517 44.244.2 실시예 6Example 6 Inv-199Inv-199 6.656.65 516516 43.343.3 실시예 7Example 7 Inv-223Inv-223 6.666.66 517517 45.445.4 실시예 8Example 8 Inv-225Inv-225 6.736.73 517517 41.541.5 실시예 9Example 9 Inv-232Inv-232 6.526.52 514514 43.143.1 실시예 10Example 10 Inv-233Inv-233 6.536.53 516516 45.245.2 실시예 11Example 11 Inv-253Inv-253 6.486.48 518518 43.343.3 실시예 12Example 12 Inv-274Inv-274 6.486.48 517517 43.643.6 실시예 13Example 13 Inv-278Inv-278 6.726.72 516516 42.742.7 실시예 14Example 14 Inv-284Inv-284 6.806.80 517517 43.343.3 실시예 15Example 15 Inv-364Inv-364 6.636.63 516516 42.742.7 실시예 16Example 16 Inv-376Inv-376 6.756.75 516516 42.842.8 실시예 17Example 17 Inv-373Inv-373 6.556.55 516516 43.943.9 실시예 18Example 18 Inv-451Inv-451 6.636.63 518518 41.341.3 실시예 19Example 19 Inv-455Inv-455 6.626.62 516516 44.244.2 실시예 20Example 20 Inv-467Inv-467 6.516.51 516516 41.441.4 비교예 1Comparative Example 1 CBPCBP 6.936.93 516516 38.238.2

상기 표1에 나타낸 바와 같이, 본 발명의 화합물을 녹색 유기 전계 발광 소자의 발광층에 사용한 경우(실시예 1 내지 20)가 종래 CBP를 녹색 유기 전계 발광 소자에 사용한 경우(비교예1)보다 효율 및 구동전압이 우수한 것을 확인할 수 있다.
As shown in Table 1, when the compound of the present invention was used for the light emitting layer of the green organic electroluminescent device (Examples 1 to 20), the efficiency and the efficiency of the conventional organic electroluminescent device (Comparative Example 1) It can be confirmed that the driving voltage is excellent.

[실시예 21 내지 24] 적색 유기 전계 발광 소자의 제조[Examples 21 to 24] Preparation of red organic electroluminescent device

합성예에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제조하였다.The compound synthesized in Synthesis Example was 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 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)/ 90% 합성예 21 내지 24 각각의 화합물 + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.
(60 nm) / TCTA (80 nm) / 90% of each compound of Synthetic Examples 21 to 24 + 10% (piq) 2 Ir (acac) (30 nm) / BCP 10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm).

[비교예 2] 적색 유기 전계 발광 소자의 제조[Comparative Example 2] Production of red organic electroluminescent device

발광층 형성시 발광 호스트 물질로서 합성예 21의 화합물 대신 CBP를 사용하는 것을 제외하고는 실시예 21과 동일한 과정으로 소자를 제조하였다.
A device was fabricated in the same manner as in Example 21 except that CBP was used instead of the compound of Synthesis Example 21 as a luminescent host material in forming the light emitting layer.

상기 실시예 21 내지 24 및 비교예 2에서 사용된 m-MTDATA, TCTA, BCP 및 CBP의 구조는 상기와 같고, (piq)2Ir(acac)의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, BCP and CBP used in Examples 21 to 24 and Comparative Example 2 are as described above, and the structure of (piq) 2 Ir (acac) is as follows.

Figure pat00088

Figure pat00088

[평가예 2][Evaluation Example 2]

실시예 21 내지 24 및 비교예 2에서 제조된 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 the organic electroluminescent devices manufactured in Examples 21 to 24 and Comparative Example 2, 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 21Example 21 Inv-212Inv-212 4.734.73 12.312.3 실시예 22Example 22 Inv-216Inv-216 4.684.68 13.113.1 실시예 23Example 23 Inv-293Inv-293 4.654.65 12.312.3 실시예 24Example 24 Inv-383Inv-383 4.694.69 12.912.9 비교예 2Comparative Example 2 CBPCBP 5.255.25 8.28.2

상기 표2에 나타낸 바와 같이, 본 발명의 화합물을 적색 유기 전계 발광 소자의 발광층에 사용한 경우(실시예 21 내지 24)가 종래 CBP를 적색 유기 전계 발광 소자에 사용한 경우(비교예2)보다 효율 및 구동전압이 우수한 것을 확인할 수 있다.As shown in Table 2, when the compound of the present invention was used for the light emitting layer of the red organic electroluminescent device (Examples 21 to 24), the efficiency and the efficiency of the conventional CBP used for the red organic electroluminescent device It can be confirmed that the driving voltage is excellent.

Claims (8)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure pat00089

상기 화학식 1에서,
R1과 R2 및 R2와 R3 중 적어도 하나는 하기 화학식 2로 표시되는 축합 고리를 형성하며,
[화학식 2]
Figure pat00090

상기 화학식 1에서,
X1은 CAr2Ar3, NAr4, O, S 및 SiAr5Ar6로 이루어진 군에서 선택되고,
상기 R1 내지 R10은 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있으며,
상기 Ar1 내지 Ar6 은 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고,
상기 R1 내지 R10 및 Ar1 내지 Ar6의 알킬기, 알케닐기, 알키닐기 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기 및 아릴아민기는 각각 독립적으로, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택된 1종 이상으로 치환될 수 있다.A compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00089

In Formula 1,
At least one of R 1 and R 2 and R 2 and R 3 forms a condensed ring represented by the following formula (2)
(2)
Figure pat00090

In Formula 1,
X 1 is selected from the group consisting of CAr 2 Ar 3 , NAr 4 , O, S and SiAr 5 Ar 6 ,
Wherein R 1 to R 10 each independently represent hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ alkynyl group of C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 of, C 3 ~ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 aryl silyl group, a alkyl boronic of C 1 ~ C 40, an aryl boronic a C 6 ~ C 60, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ selected from the group consisting of C 60 aryl amine, or by combining adjacent groups may form a fused ring,
Each of Ar 1 to Ar 6 is independently a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, A C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group, a C 3 to C 6 heteroaryl group, 40 alkylsilyl group, C 6 ~ C 60 aryl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 pingi, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 of is selected from the group consisting of an aryl amine,
Alkyl group of the R 1 to R 10 and Ar 1 to Ar 6, an alkenyl group, an alkynyl group a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkyloxy group, an aryloxy group, an alkylsilyl group, an arylsilyl group, alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an arylamine group, each independently, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ alkynyl group of C 40 , A C 3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group , A C 6 to C 60 aryloxy group, a C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group may be substituted with C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide of the group and a C 6 ~ 1 or more selected from the group consisting of C 60 arylamines. 제1항에 있어서,
상기 화학식 1로 표시되는 화합물이 하기 화학식 3 내지 6으로 표시되는 화합물로 이루어진 군에서 선택되는 화합물:
[화학식 3]
Figure pat00091

[화학식 4]
Figure pat00092

[화학식 5]
Figure pat00093

[화학식 6]
Figure pat00094

상기 화학식 3 내지 6에서,
X1, R1, R3 내지 R10 및 Ar1은 제1항에서 정의한 바와 같다.The method according to claim 1,
Wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (3) to (6):
(3)
Figure pat00091

[Chemical Formula 4]
Figure pat00092

[Chemical Formula 5]
Figure pat00093

[Chemical Formula 6]
Figure pat00094

In the above formulas 3 to 6,
X 1 , R 1 , R 3 to R 10 and Ar 1 are as defined in claim 1 . 제1항에 있어서,
X1이 NAr4, O 또는 S인 화합물.The method according to claim 1,
The compound X 1 is NAr 4, O or S. 제 1항에 있어서,
상기 Ar1 내지 Ar6이 각각 독립적으로 C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C6~C40의 아릴아민기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되는 화합물.The method according to claim 1,
Each of Ar 1 to Ar 6 is independently a C 6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C 6 to C 40 arylamine group, and a C 6 to C 40 arylsilyl group &Lt; / RTI &gt; 제1항에 있어서,
상기 R1 내지 R10이 각각 독립적으로 수소, 할로겐, 시아노기. 니트로기, C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 이루어진 군에서 선택되는 화합물.The method according to claim 1,
Each of R 1 to R 10 is independently hydrogen, halogen, cyano group. A nitro group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms. (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제5항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.1. An organic electroluminescent device comprising: (i) an anode, (ii) a cathode, and (iii) one or more organic layers sandwiched 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 5. 제6항에 있어서,
상기 화합물을 포함하는 유기물층이 정공 주입층, 정공 수송층, 전자 수송층 및 발광층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.The method according to claim 6,
Wherein the organic compound layer containing the compound is selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron transporting layer, and a light emitting layer. 제7항에 있어서,
상기 화합물을 포함하는 유기물층은 발광층이고,
상기 화합물은 상기 발광층의 인광 호스트인 유기 전계 발광 소자.8. The method of claim 7,
The organic compound layer containing the compound is a light emitting layer,
Wherein the compound is a phosphorescent host of the light emitting layer.
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