KR101618413B1 - 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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KR101618413B1
KR101618413B1 KR1020130157132A KR20130157132A KR101618413B1 KR 101618413 B1 KR101618413 B1 KR 101618413B1 KR 1020130157132 A KR1020130157132 A KR 1020130157132A KR 20130157132 A KR20130157132 A KR 20130157132A KR 101618413 B1 KR101618413 B1 KR 101618413B1
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한송이
김성무
이인혁
김은진
김영배
김태형
백영미
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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Abstract

본 발명은 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명의 유기 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층에 사용됨에 따라 유기 전계 발광 소자의 발광효율, 구동 전압, 수명 등을 향상시킬 수 있다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic compound and an organic electroluminescent device including the organic compound. Since the organic compound of the present invention is used in an organic compound layer of an organic electroluminescent device, preferably a light emitting layer, 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 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.

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.An anthracene derivative is known as a fluorescent dopant / host material used in a 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.

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

또 본 발명은 상기 유기 화합물을 포함하여 구동전압 및 발광효율이 향상된 유기 전계 발광 소자를 제공하는 것도 목적으로 한다.It is another object of the present invention to provide an organic electroluminescent device including the organic compound and having improved driving voltage and luminous efficiency.

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 112013115420214-pat00001
Figure 112013115420214-pat00001

상기 화학식 1에서,In Formula 1,

Ar1은 하기 화학식 2로 표시되는 치환기이고;Ar 1 is a substituent represented by the following formula (2);

[화학식 2](2)

Figure 112013115420214-pat00002
Figure 112013115420214-pat00002

상기 화학식 1 및 2 에서,In the above Formulas 1 and 2,

X1 내지 X5는 각각 독립적으로 N 또는 C(R11)이고, 이때, 적어도 하나 이상은 N이며;X 1 to X 5 are each independently N or C (R 11 ), wherein at least one is N;

Y1은 O 또는 S이고;Y 1 is O or S;

L1 내지 L3는 각각 독립적으로 단일결합, C6~C40의 아릴렌기 및 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되며;L 1 to L 3 are each independently selected from the group consisting of a single bond, a C 6 to C 40 arylene group and a heteroarylene group having 5 to 40 nuclear atoms;

R1 내지 R11은 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, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;R 1 to R 11 each independently represent hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 of the An 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 A 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 an aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide of the group and a C 6 ~ C 40 of is selected from the group consisting of aryl silyl group, by combining groups adjacent to form a condensed ring;

R1 내지 R9 중 하나는 L2와 결합하며, One of R 1 to R 9 is bonded to L 2 ,

m은 0 내지 4의 정수이고,m is an integer of 0 to 4,

상기 L1 내지 L3의 아릴렌기, 헤테로아릴렌기와, 상기 R1 내지 R11의 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 치환 또는 비치환될 수 있다. 이때, L1 내지 L3과, R1 내지 R11이 복수개의 치환기로 치환될 경우 복수개의 치환기는 서로 동일하거나 상이하다.Wherein L 1 to L 3 arylene group, heteroarylene group, an alkyl group of the R 1 to R 11 of the group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, an arylamine group, a cycloalkyl alkyl group, a heterocycloalkyl group, alkylsilyl group, an alkyl boron group, an aryl boron group, an aryl phosphine group, aryl phosphine oxide group and an aryl silyl group, each independently, a deuterium, a halogen, cyano group, C alkyl group of 1 ~ C 40, C 2 ~ alkenyl group of C 40, 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 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, a nuclear atom number of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ alkyl boron C 40 group, a 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 of the With at least one selected from the eojin group may be unsubstituted or substituted. When L 1 to L 3 and R 1 to R 11 are substituted by a plurality of substituents, the plurality of substituents may be the same or different from each other.

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 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising 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 to provide.

본 발명에서의 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 등이 있는데, 이에 한정되지 않는다.The alkyl in the present invention 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 발명에서의 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) 등이 있는데, 이에 한정되지 않는다.The alkenyl in the present invention 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 발명에서의 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) 등이 있는데, 이에 한정되지 않는다.The alkynyl in the present invention means a monovalent substituent derived from a straight 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 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 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; 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, a form in which two or more rings are pendant or condensed with each other may be included, 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, 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 포함할 수 있다. 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. can do. 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 40의 아릴로 치환된 아민을 의미한다.The arylamine in the present invention means an amine substituted with aryl having 6 to 40 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. 유기 화합물1. Organic compounds

본 발명의 신규 유기 화합물은 디벤조퓨란(dibenzo[b,d]furan) 또는 디벤조싸이오펜(dibenzo[b,d]thiophene)과, 6원 헤테로환과, 카바졸 모이어티(carbazole moiety)가 링커기에 의해 질소에 결합되거나, 질소에 직접 결합하여 기본 골격을 이루며, 상기 기본 골격에 다양한 치환체가 결합된 구조로서 상기 화학식 1로 표시되는 것을 특징으로 한다.The novel organic compounds of the present invention can be prepared by reacting dibenzo [b, d] furan or dibenzo [b, d] thiophene with a 6-membered heterocycle and a carbazole moiety, Or directly bonded to nitrogen to form a basic skeleton, and various substituents are bonded to the basic skeleton, and is represented by the above formula (1).

이러한 본 발명의 화학식 1로 표시되는 화합물은 높은 삼중항 에너지를 가지는 카바졸 모이어티(carbazole moiety)와, 디벤조싸이오펜(dibenzo[b,d]thiophene) 또는 디벤조퓨란(dibenzo[b,d]furan)이 아민기를 중심으로 비대칭결합되어 있어 삼중항 에너지가 크고 전기화학적으로 안정하다.The compound represented by formula (1) of the present invention can be produced by reacting a carbazole moiety having high triplet energy with dibenzo [b, d] thiophene or dibenzo [b, d ] furan) is asymmetrically bonded around the amine group, so that the triplet energy is large and electrochemically stable.

또한 본 발명의 화학식 1로 표시되는 화합물은 전자 공여성이 큰 전자주게기(electron donating group, EDG)인 아민기와 카바졸 모이어티가 결합된 구조에 전자 흡수성이 큰 전자끄는기(electron withdrawing group, EWG)인 6원 헤테로환(예를 들어, 피리딘, 피리미딘, 트리아진)이 결합되어 분자 전체가 바이폴라(bipolar) 특성을 나타내기 때문에 넓은 밴드갭을 가진다. In addition, the compound represented by Formula 1 of the present invention is an electron withdrawing group having a structure in which an amine group, which is an electron donating group (EDG), and a carbazole moiety are bonded to each other, (E. G., EWG) 6-membered heterocycle (e.g., pyridine, pyrimidine, and triazine) are bonded so that the entire molecule exhibits bipolar characteristics.

또 본 발명의 화학식 1로 표시되는 화합물은 방향족 환(aromatic ring) 또는 헤테로방향족 환(heteroaromatic ring)과 같은 치환체의 결합으로 인해 화합물의 분자량이 유의적으로 증대되어 유리전이온도가 향상됨에 따라 종래의 유기물층 재료(예를 들어, CBP)보다 높은 열적 안정성을 나타낼 수 있다. 이외에도 본 발명의 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에 효과가 있으며 유기물층에서 정공과 전자의 결합력을 높일 수 있다.In addition, since the compound represented by the formula (1) of the present invention significantly increases the molecular weight of a compound due to the substituent such as an aromatic ring or a heteroaromatic ring, the glass transition temperature is improved, Can exhibit higher thermal stability than organic layer materials (e.g., CBP). In addition, the compound represented by Chemical Formula (1) of the present invention is effective for inhibiting crystallization of the organic material layer and can enhance the bonding force between holes and electrons in 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. 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. Such lifetime enhancement of the organic electroluminescent device can maximize the performance of the full color organic light emitting panel.

본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 7로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하다.The compound represented by formula (1) of the present invention is preferably selected from the group consisting of compounds represented by the following formulas (3) to (7).

[화학식 3](3)

Figure 112013115420214-pat00003
Figure 112013115420214-pat00003

[화학식 4][Chemical Formula 4]

Figure 112013115420214-pat00004
Figure 112013115420214-pat00004

[화학식 5][Chemical Formula 5]

Figure 112013115420214-pat00005
Figure 112013115420214-pat00005

[화학식 6][Chemical Formula 6]

Figure 112013115420214-pat00006
Figure 112013115420214-pat00006

[화학식 7](7)

Figure 112013115420214-pat00007
Figure 112013115420214-pat00007

상기 화학식 3 내지 7에서, Ar1, Y1, L1, L2, R1 내지 R10 및 m은 상기 화학식 1에서의 정의한 바와 동일하다.In the above formulas 3 to 7, Ar 1 , Y 1 , L 1 , L 2 , R 1 to R 10 and m are the same as defined in the above formula (1).

여기서 유기 전계 발광 소자의 특성을 고려할 때, 본 발명의 화학식 1로 표시되는 화합물은 상기 화학식 5 또는 화학식 7로 표시되는 화합물인 것이 바람직하다.In view of the characteristics of the organic electroluminescent device, the compound represented by formula (1) of the present invention is preferably a compound represented by formula (5) or (7).

또한 본 발명의 화학식 1로 표시되는 화합물에서, Ar1은 상기 화학식 2로 표시되는 치환기인데, 구체적으로 하기 A-1 내지 A-15로 표시되는 치환기 중 어느 하나로 구체화 될 수 있다.In the compound represented by the general formula (1) of the present invention, Ar 1 is a substituent represented by the general formula (2), and may be specifically exemplified by any one of the substituents represented by the following A-1 to A-15.

Figure 112013115420214-pat00008
Figure 112013115420214-pat00008

상기 화학식 A-1 내지 A-15 에서,In the above formulas A-1 to A-15,

L3 및 R11은 상기 화학식 1에서 정의한 바와 같고, 이때, 복수개의 R11은 서로 동일하거나 상이하며,L 3 and R 11 are the same as defined in Formula 1, wherein a plurality of R 11 s are the same as or different from each other,

R21은 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 선택되며, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, R 21 represents 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, of 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, a nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine group, C 6 of ~ C 40 aryl phosphine oxide group, and a C 6 ~ is selected from the group consisting of aryl silyl group of C 40, by combining groups of adjacent, it may form a condensed ring,

n은 0 내지 4의 정수이다.n is an integer of 0 to 4;

이때, 상기 R21의 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 치환 또는 비치환될 수 있고, R21이 복수개의 치환기로 치환될 경우 복수개의 치환기는 서로 동일하거나 상이할 수 있다.In this case, the alkyl group of said R 21, 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 arylboronic A halogen atom, a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkenyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl 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, an aryl boronic of C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl group silyl groups substituted or unsubstituted with one or more selected from the consisting of And when R 21 is substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other.

한편 본 발명의 화학식 1로 표시되는 화합물에서, L1 내지 L3는 각각 독립적으로 단일결합, C6~C40의 아릴렌기 및 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되는데. 상기 아릴렌기와 헤테로아릴렌기의 예로는 페닐렌기, 비페닐렌기, 나프틸렌기, 안트라세닐렌기, 인데닐렌기, 피란트레닐렌기, 카르바졸릴렌기, 티오페닐렌기, 인돌일렌기, 푸리닐렌기, 퀴놀리닐렌기, 피롤일렌기, 이미다졸릴렌기, 옥사졸릴렌기, 티아졸릴렌기, 트리아졸릴렌기, 피리디닐렌기, 피리미디닐렌기 등을 들 수 있다. 여기서 L1 내지 L3는 각각 독립적으로 단일결합, 페닐렌기 또는 비페닐렌기인 것이 바람직하다.In the compound represented by the formula (1) of the present invention, each of L 1 to L 3 is independently selected from the group consisting of a single bond, a C 6 to C 40 arylene group, and a heteroarylene group having 5 to 40 nuclear atoms. Examples of the arylene group and the heteroarylene group include a phenylene group, a biphenylene group, a naphthylene group, an anthracenylene group, indenylene group, pyranthrenylene group, carbazolylene group, thiophenylene group, indolylene group, , A quinolinylene group, a pyrrolylene group, an imidazolylene group, an oxazolylene group, a thiazolylene group, a triazolylene group, a pyridinylene group, and a pyrimidinylene group. Here, it is preferable that each of L 1 to L 3 independently represents a single bond, a phenylene group or a biphenylene group.

이러한 본 발명의 화학식 1로 표시되는 화합물의 예로는 하기 화합물을 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, but the compound represented by the formula (1) of the present invention is not limited to the following compounds.

Figure 112013115420214-pat00009
Figure 112013115420214-pat00009

Figure 112013115420214-pat00010
Figure 112013115420214-pat00010

Figure 112013115420214-pat00011
Figure 112013115420214-pat00011

Figure 112013115420214-pat00012
Figure 112013115420214-pat00012

Figure 112013115420214-pat00013
Figure 112013115420214-pat00013

Figure 112013115420214-pat00014
Figure 112013115420214-pat00014

Figure 112013115420214-pat00015
Figure 112013115420214-pat00015

Figure 112013115420214-pat00016
Figure 112013115420214-pat00016

Figure 112013115420214-pat00017
Figure 112013115420214-pat00017

Figure 112013115420214-pat00018
Figure 112013115420214-pat00018

Figure 112013115420214-pat00019
Figure 112013115420214-pat00019

Figure 112013115420214-pat00020
Figure 112013115420214-pat00020

Figure 112013115420214-pat00021
Figure 112013115420214-pat00021

Figure 112013115420214-pat00022
Figure 112013115420214-pat00022

Figure 112013115420214-pat00023
Figure 112013115420214-pat00023

Figure 112013115420214-pat00024
Figure 112013115420214-pat00024

Figure 112013115420214-pat00025
Figure 112013115420214-pat00025

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 전계 발광 소자2. Organic electroluminescent device

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.

[준비예 1] TCA-1의 합성[Preparation Example 1] Synthesis of TCA-1

Figure 112013115420214-pat00026
Figure 112013115420214-pat00026

질소 기류 하에서 4-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 4-(4-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-1 (8.42g, 수율 71%)을 얻었다.B, d] thiophene (6.79 g, 20.0 mmol), Pd (2-benzyloxyphenyl) 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-1 (8.42 g, yield 71%) was obtained by column chromatography.

MS [M+1]+ 593MS [M + 1] < + > 593

Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41
Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41

[준비예 2] TCA-2의 합성[Preparation Example 2] Synthesis of TCA-2

Figure 112013115420214-pat00027
Figure 112013115420214-pat00027

질소 기류 하에서 4-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 4-(3-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-2 (8.66g, 수율 73%)을 얻었다.Dibenzo [b, d] thiophene (6.79g, 20.0mmol), Pd (6.79g, 20.0mmol) 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-2 (8.66 g, yield 73%) was obtained by column chromatography.

MS [M+1]+ 593MS [M + 1] < + > 593

Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41
Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41

[준비예 3] TCA-3의 합성[Preparation Example 3] Synthesis of TCA-3

Figure 112013115420214-pat00028
Figure 112013115420214-pat00028

질소 기류 하에서 4-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 4-(4-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-3 (7.24g, 수율 70%)을 얻었다.Dibenzo [b, d] thiophene (6.79 g, 20.0 mmol) and Pd 2 (dba) were added to a solution of 4- (9H- 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-3 (7.24 g, yield 70%) was obtained by column chromatography.

MS [M+1]+ 517MS [M + 1] < + > 517

Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21
Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21

[준비예 4] TCA-4의 합성[Preparation Example 4] Synthesis of TCA-4

Figure 112013115420214-pat00029
Figure 112013115420214-pat00029

질소 기류 하에서 4-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 4-(3-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-4 (7.76g, 수율 75%)을 얻었다.Dibenzo [b, d] thiophene (6.79 g, 20.0 mmol), Pd 2 (dba), 4- (9H- 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-4 (7.76 g, yield 75%) was obtained by column chromatography.

MS [M+1]+ 517MS [M + 1] < + > 517

Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21
Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21

[준비예 5] TCA-5의 합성[Preparation Example 5] Synthesis of TCA-5

Figure 112013115420214-pat00030
Figure 112013115420214-pat00030

질소 기류 하에서 3-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 4-(4-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-5 (8.06g, 수율 68%)을 얻었다.Dibenzo [b, d] thiophene (6.79g, 20.0mmol), Pd (6.79g, 20.0mmol) 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-5 (8.06 g, yield 68%) was obtained by column chromatography.

MS [M+1]+ 593MS [M + 1] < + > 593

Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41
Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41

[준비예 6] TCA-6의 합성[Preparation Example 6] Synthesis of TCA-6

Figure 112013115420214-pat00031
Figure 112013115420214-pat00031

질소 기류 하에서 3-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 4-(3-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-6 (8.66g, 수율 73%)을 얻었다.Dibenzo [b, d] thiophene (6.79 g, 20.0 mmol), Pd (2-benzyloxyphenyl) 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-6 (8.66 g, yield 73%) was obtained by column chromatography.

MS [M+1]+ 593MS [M + 1] < + > 593

Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41
Elemental Analysis: C, 85.10; H, 4.76; N, 4.73; S, 5.41

[준비예 7] TCA-7의 합성[Preparation Example 7] Synthesis of TCA-7

Figure 112013115420214-pat00032
Figure 112013115420214-pat00032

질소 기류 하에서 3-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 4-(4-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-7 (7.03g, 수율 68%)을 얻었다.Dibenzo [b, d] thiophene (6.79 g, 20.0 mmol) and Pd 2 (dba) were added to a solution of 4- (9H- 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-7 (7.03 g, yield 68%) was obtained by column chromatography.

MS [M+1]+ 517MS [M + 1] < + > 517

Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21
Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21

[준비예 8] TCA-8의 합성[Preparation Example 8] Synthesis of TCA-8

Figure 112013115420214-pat00033
Figure 112013115420214-pat00033

질소 기류 하에서 3-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 4-(3-bromophenyl)dibenzo[b,d]thiophene (6.79g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-8 (7.76g, 수율 75%)을 얻었다.(3-bromophenyl) dibenzo [b, d] thiophene (6.79 g, 20.0 mmol), Pd 2 (dba) 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-8 (7.76 g, yield 75%) was obtained by column chromatography.

MS [M+1]+ 517MS [M + 1] < + > 517

Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21
Elemental Analysis: C, 83.69; H, 4.68; N, 5.42; S, 6.21

[준비예 9] TCA-9의 합성[Preparation Example 9] Synthesis of TCA-9

Figure 112013115420214-pat00034
Figure 112013115420214-pat00034

질소 기류 하에서 4-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 2-(4-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-9 (9.00g, 수율 78%)을 얻었다.Dibenzo [b, d] furan (6.46g, 20.0mmol), Pd (6.6g, 20.0mmol) 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-9 (9.00 g, yield 78%) was obtained by column chromatography.

MS [M+1]+ 577MS [M + 1] < + > 577

Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77
Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77

[준비예 10] TCA-10의 합성[Preparation Example 10] Synthesis of TCA-10

Figure 112013115420214-pat00035
Figure 112013115420214-pat00035

질소 기류 하에서 4-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-10 (8.19g, 수율 71%)을 얻었다.Dibenzo [b, d] furan (6.46 g, 20.0 mmol), Pd (2-bromophenyl) dibenzoyl chloride 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-10 (8.19 g, yield 71%) was obtained by column chromatography.

MS [M+1]+ 577MS [M + 1] < + > 577

Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77
Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77

[준비예 11] TCA-11의 합성[Preparation Example 11] Synthesis of TCA-11

Figure 112013115420214-pat00036
Figure 112013115420214-pat00036

질소 기류 하에서 4-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 2-(4-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-11 (7.41g, 수율 74%)을 얻었다.Dibenzo [b, d] furan (6.46 g, 20.0 mmol) and Pd 2 (dba) were added to a solution of 4- (9H-carbazol-9-yl) aniline (5.17 g, 20.0 mmol) 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-11 (7.41 g, yield 74%) was obtained by column chromatography.

MS [M+1]+ 501MS [M + 1] < + > 501

Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; O, 3.20
Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; , 3.20

[준비예 12] TCA-12의 합성[Preparation Example 12] Synthesis of TCA-12

Figure 112013115420214-pat00037
Figure 112013115420214-pat00037

질소 기류 하에서 4-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-12 (6.91g, 수율 69%)을 얻었다.Dibenzo [b, d] furan (6.46 g, 20.0 mmol) and Pd 2 (dba) were added to a solution of 4- (9H-carbazol-9- yl) aniline (5.17 g, 20.0 mmol) 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-12 (6.91 g, yield 69%) was obtained by column chromatography.

MS [M+1]+ 501MS [M + 1] < + > 501

Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; O, 3.20
Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; , 3.20

[준비예 13] TCA-13의 합성[Preparation Example 13] Synthesis of TCA-13

Figure 112013115420214-pat00038
Figure 112013115420214-pat00038

질소 기류 하에서 3-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 2-(4-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-13 (9.00g, 수율 78%)을 얻었다.Dibenzo [b, d] furan (6.46 g, 20.0 mmol), Pd (2-benzyloxyphenyl) 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-13 (9.00 g, yield 78%) was obtained by column chromatography.

MS [M+1]+ 577MS [M + 1] < + > 577

Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77
Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77

[준비예 14] TCA-14의 합성[Preparation Example 14] Synthesis of TCA-14

Figure 112013115420214-pat00039
Figure 112013115420214-pat00039

질소 기류 하에서 3-(9-phenyl-9H-carbazol-3-yl)aniline (6.69g, 20.0mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-14 (7.62g, 수율 66%)을 얻었다.Dibenzo [b, d] furan (6.46 g, 20.0 mmol), Pd (2-benzyloxyphenyl) 2 (dba) 3 (0.91g, 1.00mmol), (t-Bu) 3 P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol) to put in 100ml toluene for 12 hours at 110 ℃ Lt; / RTI > After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-14 (7.62 g, yield 66%) was obtained by column chromatography.

MS [M+1]+ 577MS [M + 1] < + > 577

Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77
Elemental Analysis: C, 87.47; H, 4.89; N, 4.86; O, 2.77

[준비예 15] TCA-15의 합성[Preparation Example 15] Synthesis of TCA-15

Figure 112013115420214-pat00040
Figure 112013115420214-pat00040

질소 기류 하에서 3-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 2-(4-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-15 (7.41g, 수율 74%)을 얻었다.Dibenzo [b, d] furan (6.46 g, 20.0 mmol) and Pd 2 (dba) were added to a solution of 3- (9H- 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-15 (7.41 g, yield 74%) was obtained by column chromatography.

MS [M+1]+ 501MS [M + 1] < + > 501

Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; O, 3.20
Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; , 3.20

[준비예 16] TCA-16의 합성[Preparation Example 16] Synthesis of TCA-16

Figure 112013115420214-pat00041
Figure 112013115420214-pat00041

질소 기류 하에서 3-(9H-carbazol-9-yl)aniline (5.17g, 20.0mmol), 2-(3-bromophenyl)dibenzo[b,d]furan (6.46g, 20.0mmol), Pd2(dba)3 (0.91g, 1.00mmol), (t-Bu)3P (0.80g, 4.0mmol), sodium tert-butoxide (5.76g, 60.0mmol)를 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 TCA-16 (7.21g, 수율 72%)을 얻었다.Dibenzo [b, d] furan (6.46 g, 20.0 mmol) and Pd 2 (dba) in anhydrous N, 3 (0.91 g, 1.00 mmol), (t-Bu) 3 P (0.80 g, 4.0 mmol) and sodium tert-butoxide (5.76 g, 60.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, TCA-16 (7.21 g, yield 72%) was obtained by column chromatography.

MS [M+1]+ 501MS [M + 1] < + > 501

Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; O, 3.20
Elemental Analysis: C, 86.38; H, 4.83; N, 5.60; , 3.20

[합성예 1] C-1의 합성[Synthesis Example 1] Synthesis of C-1

Figure 112013115420214-pat00042
Figure 112013115420214-pat00042

질소 기류 하에서 TCA-1 (5.93g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-1 (7.75g, 수율 75%)를 얻었다. (5.93 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-1 (7.75 g, yield 75%) was obtained by column chromatography.

MS [M+1]+ 900
MS [M + 1] < + > 900

[합성예 2] C-2의 합성[Synthesis Example 2] Synthesis of C-2

Figure 112013115420214-pat00043
Figure 112013115420214-pat00043

질소 기류 하에서 TCA-1 (5.93g, 10.00mmol), 4-(4-chlorophenyl)-2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-2 (7.75g, 수율 75%)를 얻었다. (5.93 g, 10.00 mmol), 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (4.11 g, 12.00 mmol) and Pd 2 (dba) 3 (0.46 g, 0.5 mmol) t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound C-2 (7.75 g, yield 75%) was obtained by column chromatography.

MS [M+1]+ 899
MS [M + 1] < + > 899

[합성예 3] C-4의 합성[Synthesis Example 3] Synthesis of C-4

Figure 112013115420214-pat00044
Figure 112013115420214-pat00044

질소 기류 하에서 TCA-5 (5.93g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-4 (6.30g, 수율 70%)를 얻었다. (5.93 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-4 (6.30 g, yield 70%) was obtained by column chromatography.

MS [M+1]+ 900
MS [M + 1] < + > 900

[합성예 4] C-7의 합성[Synthesis Example 4] Synthesis of C-7

Figure 112013115420214-pat00045
Figure 112013115420214-pat00045

질소 기류 하에서 TCA-2 (5.93g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-7 (5.49g, 수율 61%)를 얻었다. (5.93 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound C-7 (5.49 g, yield 61%) was obtained by column chromatography.

MS [M+1]+ 900
MS [M + 1] < + > 900

[합성예 5] C-13의 합성[Synthesis Example 5] Synthesis of C-13

Figure 112013115420214-pat00046
Figure 112013115420214-pat00046

질소 기류 하에서 TCA-1 (5.93g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-13 (6.03g, 수율 67%)를 얻었다. (5.93 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-13 (6.03 g, yield 67%) was obtained by column chromatography.

MS [M+1]+ 900
MS [M + 1] < + > 900

[합성예 6] C-14의 합성 [Synthesis Example 6] Synthesis of C-14

Figure 112013115420214-pat00047
Figure 112013115420214-pat00047

질소 기류 하에서 TCA-1 (5.93g, 10.00mmol), 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-14 (6.20g, 수율 69%)를 얻었다. (5.93 g, 10.00 mmol), 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.11 g, 12.00 mmol) and Pd 2 (dba) 3 (0.46 g, 0.5 mmol) t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-14 (6.20 g, yield 69%) was obtained by column chromatography.

MS [M+1]+ 899
MS [M + 1] < + > 899

[합성예 7] C-19의 합성[Synthesis Example 7] Synthesis of C-19

Figure 112013115420214-pat00048
Figure 112013115420214-pat00048

질소 기류 하에서 TCA-2 (5.93g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-19 (6.48g, 수율 72%)를 얻었다. (5.93 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound C-19 (6.48 g, yield 72%) was obtained by column chromatography.

MS [M+1]+ 900
MS [M + 1] < + > 900

[합성예 8] C-22의 합성[Synthesis Example 8] Synthesis of C-22

Figure 112013115420214-pat00049
Figure 112013115420214-pat00049

질소 기류 하에서 TCA-6 (5.93g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-22 (6.30g, 수율 70%)를 얻었다. (5.93 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-22 (6.30 g, yield 70%) was obtained by column chromatography.

MS [M+1]+ 900
MS [M + 1] < + > 900

[합성예 9] C-23의 합성[Synthesis Example 9] Synthesis of C-23

Figure 112013115420214-pat00050
Figure 112013115420214-pat00050

질소 기류 하에서 TCA-6 (5.93g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-23 (6.20g, 수율 69%)를 얻었다. (5.93 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (4.11 g, 12.00 mmol) and Pd 2 (dba) 3 (0.46 g, 0.5 mmol) t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-23 (6.20 g, yield 69%) was obtained by column chromatography.

MS [M+1]+ 899
MS [M + 1] < + > 899

[합성예 10] C-57의 합성[Synthesis Example 10] Synthesis of C-57

Figure 112013115420214-pat00051
Figure 112013115420214-pat00051

질소 기류 하에서 TCA-3 (5.17g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-57 (5.93g, 수율 72%)를 얻었다. (5.17 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-57 (5.93 g, yield 72%) was obtained by column chromatography.

MS [M+1]+ 824
MS [M + 1] < + > 824

[합성예 11] C-60의 합성[Synthesis Example 11] Synthesis of C-60

Figure 112013115420214-pat00052
Figure 112013115420214-pat00052

질소 기류 하에서 TCA-7 (5.17g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-60 (6.34g, 수율 77%)를 얻었다. (5.17 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-60 (6.34 g, yield 77%) was obtained by column chromatography.

MS [M+1]+ 824
MS [M + 1] < + > 824

[합성예 12] C-63의 합성[Synthesis Example 12] Synthesis of C-63

Figure 112013115420214-pat00053
Figure 112013115420214-pat00053

질소 기류 하에서 TCA-4 (5.17g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-63 (6.51g, 수율 79%)를 얻었다. (4.17 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol) and Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-63 (6.51 g, yield 79%) was obtained by column chromatography.

MS [M+1]+ 824
MS [M + 1] < + > 824

[합성예 13] C-66의 합성[Synthesis Example 13] Synthesis of C-66

Figure 112013115420214-pat00054
Figure 112013115420214-pat00054

질소 기류 하에서 TCA-8 (5.17g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-66 (5.85g, 수율 71%)를 얻었다. (5.17 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-66 (5.85 g, yield 71%) was obtained by column chromatography.

MS [M+1]+ 824
MS [M + 1] < + > 824

[합성예 14] C-78의 합성[Synthesis Example 14] Synthesis of C-78

Figure 112013115420214-pat00055
Figure 112013115420214-pat00055

질소 기류 하에서 TCA-8 (5.17g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-78 (5.83g, 수율 71%)를 얻었다. (5.17 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-78 (5.83 g, yield 71%) was obtained by column chromatography.

MS [M+1]+ 824
MS [M + 1] < + > 824

[합성예 15] C-79의 합성[Synthesis Example 15] Synthesis of C-79

Figure 112013115420214-pat00056
Figure 112013115420214-pat00056

질소 기류 하에서 TCA-8 (5.17g, 10.00mmol), 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-79 (6.20g, 수율 69%)를 얻었다. (5.1 g, 10.00 mmol), 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.11 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol) and t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound C-79 (6.20 g, yield 69%) was obtained by column chromatography.

MS [M+1]+ 823
MS [M + 1] < + > 823

[합성예 16] C-337의 합성[Synthesis Example 16] Synthesis of C-337

Figure 112013115420214-pat00057
Figure 112013115420214-pat00057

질소 기류 하에서 TCA-9 (5.77g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-337 (6.63g, 수율 75%)를 얻었다. (5.77 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-337 (6.63 g, yield 75%) was obtained by column chromatography.

MS [M+1]+ 884
MS [M + 1] < + > 884

[합성예 17] C-338의 합성[Synthesis Example 17] Synthesis of C-338

Figure 112013115420214-pat00058
Figure 112013115420214-pat00058

질소 기류 하에서 TCA-9 (5.77g, 10.00mmol), 4-(4-chlorophenyl)-2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-338 (5.47g, 수율 62%)를 얻었다. (5.77 g, 10.00 mmol), 4- (4-chlorophenyl) -2,6-diphenylpyrimidine (4.11 g, 12.00 mmol) and Pd 2 (dba) 3 (0.46 g, 0.5 mmol) t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound C-338 (5.47 g, yield 62%) was obtained by column chromatography.

MS [M+1]+ 883
MS [M + 1] < + > 883

[합성예 18] C-340의 합성[Synthesis Example 18] Synthesis of C-340

Figure 112013115420214-pat00059
Figure 112013115420214-pat00059

질소 기류 하에서 TCA-13 (5.77g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-340 (6.19g, 수율 70%)를 얻었다. (5.77 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound C-340 (6.19 g, yield 70%) was obtained by column chromatography.

MS [M+1]+ 884
MS [M + 1] < + > 884

[합성예 19] C-343의 합성[Synthesis Example 19] Synthesis of C-343

Figure 112013115420214-pat00060
Figure 112013115420214-pat00060

질소 기류 하에서 TCA-10 (5.77g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-343 (6.17g, 수율 70%)를 얻었다. (5.77 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-343 (6.17 g, yield 70%) was obtained by column chromatography.

MS [M+1]+ 884
MS [M + 1] < + > 884

[합성예 20] C-349의 합성[Synthesis Example 20] Synthesis of C-349

Figure 112013115420214-pat00061
Figure 112013115420214-pat00061

질소 기류 하에서 TCA-9 (5.77g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-349 (5.92g, 수율 67%)를 얻었다. (5.77 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound C-349 (5.92 g, yield 67%) was obtained by column chromatography.

MS [M+1]+ 884
MS [M + 1] < + > 884

[합성예 21] C-350의 합성[Synthesis Example 21] Synthesis of C-350

Figure 112013115420214-pat00062
Figure 112013115420214-pat00062

질소 기류 하에서 TCA-9 (5.77g, 10.00mmol), 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene 에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-350 (5.65g, 수율 64%)를 얻었다. (5.77 g, 10.00 mmol), 4- (3-chlorophenyl) -2,6-diphenylpyrimidine (4.11 g, 12.00 mmol) and Pd 2 (dba) 3 (0.46 g, 0.5 mmol) t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, the target compound C-350 (5.65 g, yield 64%) was obtained by column chromatography.

MS [M+1]+ 883
MS [M + 1] < + > 883

[합성예 22] C-355의 합성[Synthesis Example 22] Synthesis of C-355

Figure 112013115420214-pat00063
Figure 112013115420214-pat00063

질소 기류 하에서 TCA-10 (5.77g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-355 (6.90g, 수율 78%)를 얻었다. (5.77 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-355 (6.90 g, yield 78%) was obtained by column chromatography.

MS [M+1]+ 884
MS [M + 1] < + > 884

[합성예 23] C-358의 합성[Synthesis Example 23] Synthesis of C-358

Figure 112013115420214-pat00064
Figure 112013115420214-pat00064

질소 기류 하에서 TCA-14 (5.77g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-358 (6.54g, 수율 74%)를 얻었다. (5.77 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-358 (6.54 g, yield 74%) was obtained by column chromatography.

MS [M+1]+ 884
MS [M + 1] < + > 884

[합성예 24] C-359의 합성[Synthesis Example 24] Synthesis of C-359

Figure 112013115420214-pat00065
Figure 112013115420214-pat00065

질소 기류 하에서 TCA-14 (5.77g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-359 (6.09g, 수율 69%)를 얻었다. (5.77 g, 10.00 mmol), 2- (3-chlorophenyl) -4,6-diphenylpyrimidine (4.11 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-359 (6.09 g, yield 69%) was obtained by column chromatography.

MS [M+1]+ 883
MS [M + 1] < + > 883

[합성예 25] C-393의 합성[Synthesis Example 25] Synthesis of C-393

Figure 112013115420214-pat00066
Figure 112013115420214-pat00066

질소 기류 하에서 TCA-11 (5.01g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-393 (6.14g, 수율 76%)를 얻었다. (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (0.13 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl- (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-393 (6.14 g, yield 76%) was obtained by column chromatography.

MS [M+1]+ 808
MS [M + 1] < + > 808

[합성예 26] C-396의 합성[Synthesis Example 26] Synthesis of C-396

Figure 112013115420214-pat00067
Figure 112013115420214-pat00067

질소 기류 하에서 TCA-15 (5.01g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-396 (5.74g, 수율 71%)를 얻었다. (5.01 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-396 (5.74 g, yield 71%) was obtained by column chromatography.

MS [M+1]+ 808
MS [M + 1] < + > 808

[합성예 27] C-399의 합성[Synthesis Example 27] Synthesis of C-399

Figure 112013115420214-pat00068
Figure 112013115420214-pat00068

질소 기류 하에서 TCA-12 (5.01g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-399 (5.66g, 수율 70%)를 얻었다. (5.01 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-399 (5.66 g, yield 70%) was obtained by column chromatography.

MS [M+1]+ 808
MS [M + 1] < + > 808

[합성예 28] C-402의 합성[Synthesis Example 28] Synthesis of C-402

Figure 112013115420214-pat00069
Figure 112013115420214-pat00069

질소 기류 하에서 TCA-16 (5.01g, 10.00mmol), 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-402 (5.90g, 수율 73%)를 얻었다. (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (0.15 g, 10.00 mmol), 2- (4-chlorophenyl) -4,6-diphenyl- (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . The solvent of the filtered organic layer was removed, and the desired compound C-402 (5.90 g, yield 73%) was obtained by column chromatography.

MS [M+1]+ 808
MS [M + 1] < + > 808

[합성예 29] C-414의 합성[Synthesis Example 29] Synthesis of C-414

Figure 112013115420214-pat00070
Figure 112013115420214-pat00070

질소 기류 하에서 TCA-16 (5.01g, 10.00mmol), 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (4.13g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-414 (5.74g, 수율 71%)를 얻었다. (4.13 g, 12.00 mmol), Pd 2 (dba) 3 (0.15 g, 10.00 mmol), TCA-16 (5.01 g, 10.00 mmol) and 2- (3- chlorophenyl) -4,6- (T-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were added to 100 ml toluene and the mixture was stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-414 (5.74 g, yield 71%) was obtained by column chromatography.

MS [M+1]+ 808
MS [M + 1] < + > 808

[합성예 30] C-415의 합성[Synthesis Example 30] Synthesis of C-415

Figure 112013115420214-pat00071
Figure 112013115420214-pat00071

질소 기류 하에서 TCA-16 (5.01g, 10.00mmol), 4-(3-chlorophenyl)-2,6-diphenylpyrimidine (4.11g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-415 (6.13g, 수율 76%)를 얻었다. (4.11 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), (4-chlorophenyl) -2,6-diphenylpyrimidine t-Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-415 (6.13 g, yield 76%) was obtained by column chromatography.

MS [M+1]+ 807
MS [M + 1] < + > 807

[합성예 31] C-452의 합성[Synthesis Example 31] Synthesis of C-452

Figure 112013115420214-pat00072
Figure 112013115420214-pat00072

질소 기류 하에서 TCA-1 (5.93g, 10.00mmol), 2-(4-chlorophenyl)-5-phenylpyrimidine (3.20g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-452 (5.10g, 수율 62%)를 얻었다. (5.93 g, 10.00 mmol), 2- (4-chlorophenyl) -5-phenylpyrimidine (3.20 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol) Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-452 (5.10 g, yield 62%) was obtained by column chromatography.

MS [M+1]+ 823
MS [M + 1] < + > 823

[합성예 32] C-456의 합성[Synthesis Example 32] Synthesis of C-456

Figure 112013115420214-pat00073
Figure 112013115420214-pat00073

질소 기류 하에서 TCA-3 (5.17g, 10.00mmol), 2-(4-chlorophenyl)-5-phenylpyrimidine (3.20g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-456 (5.00g, 수율 67%)를 얻었다. (3.20 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), (t-butoxycarbonylamino) Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-456 (5.00 g, yield 67%) was obtained by column chromatography.

MS [M+1]+ 747
MS [M + 1] < + > 747

[합성예 33] C-460의 합성[Synthesis Example 33] Synthesis of C-460

Figure 112013115420214-pat00074
Figure 112013115420214-pat00074

질소 기류 하에서 TCA-8 (5.17g, 10.00mmol), 2-(4-chlorophenyl)-5-phenylpyrimidine (3.20g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-460 (4.71g, 수율 63%)를 얻었다. (3.20 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), (t-butoxycarbonylamino) Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-460 (4.71 g, yield 63%) was obtained by column chromatography.

MS [M+1]+ 747
MS [M + 1] < + > 747

[합성예 34] C-476의 합성[Synthesis Example 34] Synthesis of C-476

Figure 112013115420214-pat00075
Figure 112013115420214-pat00075

질소 기류 하에서 TCA-16 (5.01g, 10.00mmol), 2-(4-chlorophenyl)-5-phenylpyrimidine (3.20g, 12.00mmol), Pd2(dba)3 (0.46g, 0.5mmol), (t-Bu)3P (0.40g, 2.0mmol), sodium tert-butoxide (2.88g, 30.0mmol)을 100ml toluene 에 넣고 110℃에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgSO4를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 C-476 (4.97g, 수율 68%)를 얻었다. (3.20 g, 12.00 mmol), Pd 2 (dba) 3 (0.46 g, 0.5 mmol), (t-butoxycarbonylamino) Bu) 3 P (0.40 g, 2.0 mmol) and sodium tert-butoxide (2.88 g, 30.0 mmol) were placed in 100 ml toluene and stirred at 110 ° C for 12 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the mixture was filtered with MgSO 4 . After removing the solvent of the filtered organic layer, C-476 (4.97 g, yield 68%) was obtained by column chromatography.

MS [M+1]+ 731
MS [M + 1] < + > 731

[실시예 1 내지 34] 녹색 유기 전계 발광 소자의 제조[Examples 1 to 34] Production of green organic electroluminescent device

합성예4에서 합성한 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제조하였다.The compound synthesized in Synthesis Example 4 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured according to the following procedure.

먼저, ITO (Indium tin oxide)가 1500Å두께로 박막 코팅된 유리 기판을 증류수로 초음파 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척하고 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 cleaned with a solvent such as isopropyl alcohol, acetone, and 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 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 90% 합성예 1 내지 34 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 소자를 제조하였다.(60 nm) / TCTA (80 nm) / 90% Each compound of each of Synthetic Examples 1 to 34 + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) / 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.

상기 실시예 1 내지 34 및 비교예 1에서 사영된 m-MTDATA, TCTA, Ir(ppy)3, BCP 및 CBP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , BCP and CBP projected in Examples 1 to 34 and Comparative Example 1 are as follows.

Figure 112013115420214-pat00076

Figure 112013115420214-pat00076

[평가예 1][Evaluation Example 1]

실시예 1 내지 34 및 비교예 1에서 제조한 각각의 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 each of the green organic electroluminescent devices prepared in Examples 1 to 34 and Comparative Example 1, and the results are shown in the following Table 1 .

샘플Sample 호스트Host 구동전압(V)The driving voltage (V) 발광피크(nm)Emission peak (nm) 전류효율(cd/A)Current efficiency (cd / A) 실시예 1Example 1 C-1C-1 6.666.66 518518 40.640.6 실시예 2Example 2 C-2C-2 6.686.68 516516 41.041.0 실시예 3Example 3 C-4C-4 6.766.76 518518 38.738.7 실시예 4Example 4 C-7C-7 6.726.72 517517 39.439.4 실시예 5Example 5 C-13C-13 6.876.87 518518 39.139.1 실시예 6Example 6 C-14C-14 6.666.66 518518 41.241.2 실시예 7Example 7 C-19C-19 6.716.71 517517 40.740.7 실시예 8Example 8 C-22C-22 6.666.66 516516 39.939.9 실시예 9Example 9 C-23C-23 6.586.58 518518 39.139.1 실시예 10Example 10 C-57C-57 6.766.76 517517 39.139.1 실시예 11Example 11 C-60C-60 6.726.72 517517 38.738.7 실시예 12Example 12 C-63C-63 6.876.87 518518 39.139.1 실시예 13Example 13 C-66C-66 6.666.66 517517 41.141.1 실시예 14Example 14 C-78C-78 6.716.71 518518 42.242.2 실시예 15Example 15 C-79C-79 6.746.74 517517 39.439.4 실시예 16Example 16 C-337C-337 6.716.71 516516 41.341.3 실시예 17Example 17 C-338C-338 6.676.67 518518 38.938.9 실시예 18Example 18 C-340C-340 6.586.58 518518 39.139.1 실시예 19Example 19 C-343C-343 6.766.76 517517 39.039.0 실시예 20Example 20 C-349C-349 6.726.72 518518 41.141.1 실시예 21Example 21 C-350C-350 6.716.71 517517 40.040.0 실시예 22Example 22 C-355C-355 6.746.74 517517 41.041.0 실시예 23Example 23 C-358C-358 6.716.71 518518 41.541.5 실시예 24Example 24 C-359C-359 6.706.70 517517 39.839.8 실시예 25Example 25 C-393C-393 6.696.69 518518 39.139.1 실시예 26Example 26 C-396C-396 6.696.69 517517 39.339.3 실시예 27Example 27 C-399C-399 6.686.68 517517 39.839.8 실시예 28Example 28 C-402C-402 6.756.75 518518 39.739.7 실시예 29Example 29 C-414C-414 6.866.86 517517 39.839.8 실시예 30Example 30 C-415C-415 6.556.55 516516 39.139.1 실시예 31Example 31 C-452C-452 6.496.49 518518 40.240.2 실시예 32Example 32 C-456C-456 6.786.78 518518 41.741.7 실시예 33Example 33 C-460C-460 6.806.80 517517 42.942.9 실시예 34Example 34 C-476C-476 6.756.75 517517 42.442.4 비교예 1Comparative Example 1 CBPCBP 6.936.93 516516 38.238.2

상기 표1에 나타낸 바와 같이, 녹색 유기 전계 발광 소자의 발광층에 본 발명의 화합물)을 사용한 경우(실시예 1-34)가 종래의 CBP를 사용한 경우(비교예1)보다 유기 전계 발광 소자의 효율 및 구동전압이 우수한 것을 확인할 수 있다.As shown in Table 1, in the case where the compound of the present invention was used in the light emitting layer of the green organic electroluminescent device (Example 1-34), the efficiency of the organic electroluminescent device (Comparative Example 1) And the driving voltage is excellent.

Claims (6)

하기 화학식 7로 표시되는 화합물:
[화학식 7]
Figure 112016005107880-pat00085

상기 화학식 7에서,
Ar1은 하기 화학식 2로 표시되는 치환기이고;
[화학식 2]
Figure 112016005107880-pat00086

상기 화학식 7 및 2에서,
X1 내지 X5는 각각 독립적으로 N 또는 C(R11)이고, 이때, 적어도 하나 이상은 N이며;
Y1은 O 또는 S이고;
L1 내지 L3는 각각 독립적으로 단일결합, C6~C40의 아릴렌기 및 핵원자수 5 내지 40의 헤테로아릴렌기로 이루어진 군에서 선택되며;
R1 내지 R8 및 R10은 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, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;
R11은 수소, 또는 C6~C40의 아릴기이고, 단, R11이 복수일 경우, 적어도 하나 이상은 C6~C40의 아릴기이고;
m은 0 내지 4의 정수이고;
상기 L1 내지 L3의 아릴렌기, 헤테로아릴렌기와, 상기 R1 내지 R8 및 R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스핀기, 아릴포스핀옥사이드기, 아릴실릴기와, 상기 R11의 아릴기는 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 있다.A compound represented by the following formula (7):
(7)
Figure 112016005107880-pat00085

In Formula 7,
Ar 1 is a substituent represented by the following formula (2);
(2)
Figure 112016005107880-pat00086

In the above formulas (7) and (2)
X 1 to X 5 are each independently N or C (R 11 ), wherein at least one is N;
Y 1 is O or S;
L 1 to L 3 are each independently selected from the group consisting of a single bond, a C 6 to C 40 arylene group and a heteroarylene group having 5 to 40 nuclear atoms;
R 1 to R 8 and R 10 are each independently hydrogen, deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ of for C 40 aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group of, C of 6 ~ C 40 aryl amine group, C 3 ~ for C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide of the group and a C 6 ~ C 40 of is selected from the group consisting of aryl silyl group, by combining groups adjacent to form a condensed ring;
R 11 is hydrogen or a C 6 to C 40 aryl group, provided that when R 11 is plural, at least one is a C 6 to C 40 aryl group;
m is an integer from 0 to 4;
The aryl group and heteroarylene group of L 1 to L 3 and the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group of R 1 to R 8 and R 10 An alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, and an aryl group of R 11 are each independently selected from the group consisting of deuterium, halogen, anger, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, nuclear atoms aryl of from 5 to 40 heteroaryl group, a C 6 of the ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 40 aryl boron group, C 6 ~ C 40 aryl phosphine group, C 6 ~ aryl phosphine oxide of a C 40 group, and C 6 To C 40 arylsilyl groups. 삭제delete 제1항에 있어서,
상기 Ar1이 하기 A-1 내지 A-15로 표시되는 치환기로 이루어진 군에서 선택되는 화합물.
Figure 112013115420214-pat00084

상기 A-1 내지 A-15에서,
L3 및 R11은 제1항에서 정의한 바와 같고, 이때, R11은 서로 동일하거나 상이하며;
R21은 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, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며;
상기 R21의 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 있고;
n은 0 내지 4의 정수이다.The method according to claim 1,
Wherein Ar 1 is selected from the group consisting of the substituents represented by the following A-1 to A-15.
Figure 112013115420214-pat00084

In the above A-1 to A-15,
L 3 and R 11 are as defined in claim 1, wherein, R 11 are the same or different from one another;
R 21 represents 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, of 5 to 40 heteroaryl group, C 6 ~ C 40 of the aryloxy group, C 1 ~ C 40 alkyloxy group of, C 6 ~ C 40 aryl amine group, C 3 ~ C 40 cycloalkyl group, a nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, C 1 ~ C 40 group of an alkyl boron, C 6 ~ C 40 group of the arylboronic, C 6 ~ C 40 aryl phosphine group, C 6 of ~ C 40 aryl phosphine oxide of the group and a C 6 ~ C 40 of is selected from the group consisting of aryl silyl group, by combining groups adjacent to form a condensed ring;
Alkyl group of the R 21, 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 ~ C 40 aryl phosphine group, C 6 ~ C 40 aryl phosphine oxide group, and a C 6 ~ C 40 aryl silyl group may be substituted with one or more selected from the group consisting of;
n is an integer of 0 to 4; 제1항에 있어서,
상기 L1 내지 L3가 각각 독립적으로 단일결합, 페닐렌기 또는 비페닐렌기인 화합물.The method according to claim 1,
Wherein each of L 1 to L 3 is independently a single bond, a phenylene group or a biphenylene group. 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며,
상기 1층 이상의 유기물층 중 적어도 하나는 제1항, 제3항 및 제4항 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 compound layers comprises the compound according to any one of claims 1, 3, and 4. 제5항에 있어서,
상기 화합물을 포함하는 유기물층이 발광층인 유기 전계 발광 소자.6. The method of claim 5,
Wherein the organic compound layer containing the compound is a light emitting layer.
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