KR20130125182A - Novel compounds and organic electro luminescence device using the same - Google Patents

Novel compounds and organic electro luminescence device using the same Download PDF

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KR20130125182A
KR20130125182A KR1020120048726A KR20120048726A KR20130125182A KR 20130125182 A KR20130125182 A KR 20130125182A KR 1020120048726 A KR1020120048726 A KR 1020120048726A KR 20120048726 A KR20120048726 A KR 20120048726A KR 20130125182 A KR20130125182 A KR 20130125182A
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김태형
배형찬
손효석
백영미
박호철
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주식회사 두산
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Abstract

The present invention relates to a compound in which the benzothienopyridine or benzofuropyridine end is fused with a heterocyclic moiety, especially an indole derivative moiety and an organic electroluminescent device containing the same. When the compound of the present invention is used in an organic layer, an organic electroluminescent device with improved light emitting efficiency and lifetime and low driving voltage is provided.

Description

신규 화합물 및 이를 포함하는 유기 전계 발광 소자{NOVEL COMPOUNDS AND ORGANIC ELECTRO LUMINESCENCE DEVICE USING THE SAME}TECHNICAL FIELD [0001] The present invention relates to a novel compound, and an organic electroluminescent device including the same. BACKGROUND OF THE INVENTION [0002]

본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로, 보다 구체적으로는 유기 전계 발광 소자의 유기물층에 사용되는 화합물에 관한 것이다.The present invention relates to a novel compound and an organic electroluminescent device comprising the same, and more particularly to a compound used in the organic material layer of the organic electroluminescent device.

1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구는 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층 구조의 유기 전계 발광 소자가 제시되었다. 이후 유기 전계 발광 소자는 소자의 효율 및 수명을 향상시키기 위하여 소자 내 특징적인 유기물 층을 도입하는 형태로 발전해왔다.Based on Bernanose's observation of organic thin-film emission in the 1950s, the study of organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965 was carried out by Tang in 1987. An organic electroluminescent device having a laminated structure divided into functional layers has been proposed. Since the organic electroluminescent device has been developed in the form of introducing a characteristic organic layer in the device in order to improve the efficiency and life of the device.

유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서 정공이, 음극에서 전자가 유기물층으로 주입되어, 주입된 정공과 전자가 만나 엑시톤(exciton)이 형성되며, 형성된 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 유기물층으로 사용되는 물질은 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 the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic layer, and the injected holes and electrons meet to form an exciton. When the exciton formed drops to a ground state The light comes out. The material used as the organic material layer may be classified into a light emitting material, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

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

도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 인광 도판트의 개발은 이론적으로 형광 도판트에 비해 4배까지 발광 효율을 향상 시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트에 대해서도 연구되고 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. The development of phosphorescent dopants is theoretically able to improve luminous efficiency up to 4 times compared to fluorescent dopants, so research is being conducted not only on phosphorescent dopants but also on phosphorescent hosts.

현재까지 정공 수송층. 정공 주입층, 전자 수송층 등으로 사용되는 물질로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광 물질로는 안트라센 유도체들이 사용되고 있다. 특히 발광 물질 중 효율 향상 측면에서 큰 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물은 blue, green, red 인광 도판트 재료로, CBP는 인광 호스트 재료로 사용되고 있다. 이외에도 대한민국 공개특허공보 제2010-0108924호에는 아자카르바졸 유도체를 호스트 재료로 사용하는 기술이 개시되어 있다.Up to now, the hole transport layer. NPB, BCP, Alq 3 and the like are widely known as materials used for the hole injection layer and the electron transport layer, and anthracene derivatives are used as the light emitting material. In particular, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have great advantages in terms of efficiency improvement, are blue, green, and red phosphorescent dopant materials. CBP is used as a phosphorescent host material. In addition, Korean Unexamined Patent Publication No. 2010-0108924 discloses a technique of using an azacarbazole derivative as a host material.

그러나 종래의 발광 물질들은 발광 특성이 양호하나, 유기 전계 발광 소자의 수명측면에서 만족할만한 수준이 되지 못하기 때문에 우수한 성능을 가지는 발광 물질의 개발이 요구되고 있다.However, although the conventional light emitting materials have good light emission characteristics, they are not satisfactory in terms of lifespan of the organic EL device, and thus, development of a light emitting material having excellent performance is required.

본 발명은 상기한 문제점을 해결하기 위해, 유기 전계 발광 소자의 효율, 수명 및 안정성 등을 향상시킬 수 있는 신규 화합물 및 상기 화합물을 이용한 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.The present invention has been made to solve the above problems and it is an object of the present invention to provide a novel compound capable of improving the efficiency, lifetime and stability of the organic electroluminescent device and an organic electroluminescent device using the compound.

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

[화학식 1][Formula 1]

Figure pat00001
Figure pat00001

상기 화학식 1에서, A는 O(산소) 또는 S(황)이고, X1 내지 X4는, 각각 독립적으로, CR1 또는 N(질소)이고, Y1과 Y2, Y2와 Y3, Y3와 Y4 중 하나는 하기 화학식 2로 표시되는 화합물과 축합 고리를 형성하고, Y1 내지 Y4 중 축합 고리를 형성하지 않는 것은 CR2 또는 N(질소)이고, 이때, N(질소)를 반드시 하나 이상 포함하며,In Formula 1, A is O (oxygen) or S (sulfur), X 1 to X 4 are each independently CR 1 or N (nitrogen), Y 1 and Y 2 , Y 2 and Y 3 , One of Y 3 and Y 4 forms a condensed ring with a compound represented by the following formula (2), and Y 1 to Y 4 It is CR 2 or N (nitrogen) that does not form a heavy condensed ring, wherein at least one of N (nitrogen) must be included,

[화학식 2] (2)

Figure pat00002
Figure pat00002

상기 화학식 2에서, Z1 내지 Z4는, 각각 독립적으로, CR3 또는 N(질소)이고,In Chemical Formula 2, Z 1 to Z 4 are each independently CR 3 or N (nitrogen),

상기 R1 내지 R3는, 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, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 인접하는 기와 서로 결합하여 축합(fused) 고리를 형성할 수 있으며, R 1 to R 3 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- C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, (C 6 - of C 40 aryl) C of 1 - C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 of Selected from the group consisting of arylsilyl groups and bonded to adjacent groups to form a fused ring Can be formed,

상기 Ar1은 수소, 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, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된다.Ar 1 is hydrogen, 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 5 to 40 heteroaryl C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, (C 6 -C 40 aryl) C 1 -C 40 alkyl group, C 3 ~ C 40 of is selected from cycloalkyl groups, 3 to 40 nuclear atoms heterocycloalkyl group, the group consisting of C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 aryl group in the silyl.

여기서, 상기 R1 내지 R3는 인접하는 기와 결합하여 축합(fused) 고리(축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합)를 형성할 수 있다.Here, R 1 to R 3 may combine with an adjacent group to form a fused ring (fused aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring, condensed heteroaromatic ring, or a combination thereof).

또한, 상기 R1 내지 R3 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 아릴알킬기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기 및 아릴실릴기는, 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, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있으며, 복수개의 치환기를 가질 경우, 각각의 치환기는 동일하거나 상이할 수 있다.In addition, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkyl of R 1 to R 3 and Ar 1 The silyl group and the arylsilyl group are 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 aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, (C 6 to C 40 aryl) C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group and a C 6 ~ C 40 aryl silyl group selected from the group consisting of It may be substituted or unsubstituted with one or more substituents, and in the case of having a plurality of substituents, each substituent may be the same or different.

본 발명에서의 “알킬”은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알킬의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있지만, 이에 한정되는 것은 아니다."Alkyl" in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

본 발명에서의 "알케닐"은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알케닐의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있지만, 이에 한정되는 것은 아니다."Alkenyl" in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

본 발명에서의 "알키닐"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알키닐의 예로는 에타인일(ethynyl), 2-프로파인일(2-propynyl) 등을 들 수 있지만, 이에 한정되는 것은 아니다."Alkynyl" in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples of such alkynyl include, but are not limited to, ethynyl, 2-propynyl, and the like.

본 발명에서의 “아릴”은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된(fused) 형태도 포함할 수 있다. 이러한 아릴의 예로, 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있지만, 이에 한정되는 것은 아니다."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, and two or more rings are simply attached or fused to each other. ) May also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

본 발명에서의 “헤테로아릴”은 핵원자수(탄소를 포함하는 원자의 수) 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 헤테로아릴은 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된(fused) 형태로 부착될 수 있고, 아릴기와의 축합된 형태도 포함하는 것으로 해석할 수 있다. 이러한 헤테로아릴의 예로, 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있지만, 이에 한정되는 것은 아니다."Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 40 nuclear atoms (number of atoms including carbon), and at least one of the rings Carbon, preferably 1 to 3 carbons, is substituted with heteroatoms such as N, O, S or Se. Heteroaryl can be interpreted that two or more rings may be attached in a simple or fused form with each other, and also include a condensed form with an aryl group. Examples of such heteroaryl include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and the like. ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

본 발명에서의 "아릴옥시"는 RO-로 표시되는 1가의 치환기로서, 상기 R은 탄소수 6 내지 60의 아릴이다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있지만, 이에 한정되는 것은 아니다."Aryloxy" in the present invention is a monovalent substituent represented by RO-, wherein R is 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 "알킬옥시"는 R´O-로 표시되는 1가의 치환기로서, 상기 R´는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있지만, 이에 한정되는 것은 아니다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means alkyl having 1 to 40 carbon atoms, and is linear, branched or cyclic. It can be interpreted as including a structure. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

본 발명에서의 "아릴아민"은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

본 발명에서의 "시클로알킬"은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있지만, 이에 한정되는 것은 아니다. "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 cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

본 발명에서의 “헤테로시클로알킬”은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O 또는 S와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있지만, 이에 한정되는 것은 아니다.“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 in the ring, preferably 1 to 3 carbons is N, O or Substituted with a hetero atom such as S. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

본 발명에서의 "알킬실릴"은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 6 내지 40의 아릴로 치환된 실릴을 의미한다."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.

한편, 본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것이 특징인 유기 전계 발광 소자를 제공한다.On the other hand, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device characterized in that it comprises a.

여기서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다. 이때, 화학식 1로 표시되는 화합물이 발광층에 사용될 경우, 상기 화학식 1로 표시되는 화합물은 청색, 녹색 또는 적색의 인광 호스트 재료로 사용될 수 있다.Here, the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer. In this case, when the compound represented by Formula 1 is used in the light emitting layer, the compound represented by Formula 1 may be used as a phosphorescent host material of blue, green or red.

본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 유기물층(바람직하게는, 발광층의 발광 물질로)에 사용할 경우, 유기 전계 발광 소자의 효율(발광 효율 및 전령 효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 따라서, 본 발명은 성능 및 수명이 향상된 풀 칼라 유기 전계 발광 패널을 제공할 수 있다.When the compound represented by the general formula (1) of the present invention is used for an organic material layer (preferably, a light emitting material of a light emitting layer) of an organic electroluminescent device, efficiency (luminous efficiency and messaging efficiency), lifetime, Voltage and the like can be improved. Accordingly, the present invention can provide a full-color organic electroluminescence panel with improved performance and lifetime.

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

본 발명은 종래의 유기 전계 발광 소자용 재료(예를 들어, 4,4-dicarbazolybiphenyl(이하, ´CBP´라 함))보다 분자량이 클 뿐만 아니라, 넓은 에너지 밴드갭을 가지면서, 정공과 전자의 결합력을 높일 수 있는 상기 화학식 1로 표시되는 화합물을 제공하는 것이 특징이다.The present invention not only has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), but also has a wide energy band gap, It is a feature to provide a compound represented by the formula (1) that can increase the binding force.

구체적으로, 본 발명의 화학식 1로 표시되는 화합물은, 벤조싸이아노피리딘(benzothienopyridine) 또는 벤조퓨로피리딘(benzofuropyridine)의 말단에 헤테로환 모이어티, 바람직하게는 인돌 유도체 모이어티(moiety)가 결합(융합)되어 있다. 벤조싸이아노피리딘(benzothienopyridine) 또는 벤조퓨로피리딘(benzofuropyridine) 골격은 높은 triplet 에너지 레벨을 가지고 있기 때문에, 본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자에 사용할 경우, 소자의 인광특성을 개선함과 동시에 정공 주입 능력, 정공 수송 능력, 발광효율, 구동전압 및 수명 특성 등을 향상시킬 수 있다.Specifically, the compound represented by the formula (1) of the present invention, a heterocyclic moiety, preferably an indole derivative moiety (moiety) is bonded to the terminal of benzothienopyridine or benzofuropyridine Fused). Since the benzothienopyridine or benzofuropyridine skeleton has a high triplet energy level, when the compound represented by Formula 1 of the present invention is used in an organic electroluminescent device, the phosphorescence characteristics of the device are improved. At the same time, the hole injection ability, hole transport ability, luminous efficiency, driving voltage, and lifetime characteristics can be improved.

특히, 본 발명의 화학식 1로 표시되는 화합물은 벤조싸이아노피리딘 또는 벤조퓨로피리딘 골격의 말단에 결합된 인돌 유도체 모이어티로 인해 넓은 밴드갭(sky blue ~ red)을 가지면서, 정공과 전자의 결합력을 높일 수 있기 때문에 종래의 CBP에 비해 발광층의 호스트 재료, 구체적으로는 청색, 녹색 및/또는 적색의 인광 호스트 재료로서 우수한 특성을 나타낼 수 있다.In particular, the compound represented by Formula 1 of the present invention has a wide bandgap (sky blue to red) due to the indole derivative moiety bound to the terminal of the benzocyanopyridine or benzofuropyridine skeleton, Since the bonding force can be increased, it can exhibit excellent properties as a host material of the light emitting layer, specifically, a blue, green and / or red phosphorescent host material, compared to the conventional CBP.

또한, 본 발명의 화학식 1로 표시되는 화합물은 다양한 치환기(R1 내지 R3 및 Ar1)가 결합되어 화합물의 분자량이 유의적으로 증대되기 때문에 높은 유리전이온도를 나타내며, 이로 인해 종래 CBP 보다 높은 열적 안정성을 가질 수 있다.In addition, the compound represented by the formula (1) of the present invention exhibits a high glass transition temperature because a variety of substituents (R 1 to R 3 and Ar 1 ) is bonded to significantly increase the molecular weight of the compound, which is higher than the conventional CBP May have thermal stability.

본 발명의 화학식 1로 표시되는 화합물에 있어서, Y1 내지 Y4 중 축합 고리를 형성하지 않는 부분은 N을 하나 이상 포함하는 것이 바람직하다. 또한, X1 내지 X4는 모두 CR1이거나 N을 하나 이상 포함하는 것이 바람직하며, Z1 내지 Z4 도 모두 CR3이거나 N을 하나 이상 포함한 것이 바람직하다.In the compound represented by Formula 1 of the present invention, Y 1 to Y 4 It is preferable that the part which does not form a polycondensed ring contains one or more N. In addition, it is preferable that all of X 1 to X 4 are CR 1 or include one or more N, and all of Z 1 to Z 4 are preferably CR 3 or one or more N.

한편, 본 발명의 화학식 1로 표시되는 화합물에서, 인돌 유도체 모이어티에 치환되는 Ar1은 C6~C40의 아릴기 또는 핵원자수 5 내지 40의 헤테로아릴기인 것이 바람직하다.On the other hand, in the compound represented by the formula (1) of the present invention, Ar 1 substituted in the indole derivative moiety is preferably a C 6 ~ C 40 aryl group or a heteroaryl group of 5 to 40 nuclear atoms.

여기서, 상기 Ar1의 아릴기, 헤테로아릴기, 아릴아민기 및 아릴실릴기는 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, C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 복수개의 치환기를 가질 경우, 각각의 치환기는 동일하거나 상이할 수 있다.Herein, the aryl group, heteroaryl group, arylamine group and arylsilyl group of Ar 1 may be 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 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 Alkyloxy group, C 6 ~ C 40 aryl An amine group, a C 1 to C 40 alkyl group, a C 3 to C 40 cycloalkyl group, a nuclear atom having 3 to 40 heterocycloalkyl groups, a C 1 to C 40 alkylsilyl group and a C 6 to C 40 arylsilyl group It may be substituted with one or more substituents selected from the group consisting of, when having a plurality of substituents, each substituent may be the same or different.

이러한 본 발명의 화학식 1로 표시되는 화합물의 치환체(작용기)인 R1 내지 R3 및 Ar1의 예로 하기와 같은 예(S1~S138)를 들 수 있지만, 이에 한정되는 것은 아니다.Examples of R 1 to R 3 and Ar 1 which are substituents (functional groups) of the compound represented by Formula 1 of the present invention include the following examples (S1 to S138), but are not limited thereto.

Figure pat00003
Figure pat00003

Figure pat00004
Figure pat00004

Figure pat00005
Figure pat00005

이때, 본 발명의 화학식 1로 표시되는 화합물의 치환체 중 Ar1은, 하기 S-1 내지 S-39로 표시되는 구조로 이루어진 군에서 선택되는 것이 바람직하다.At this time, Ar 1 of the substituents of the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of the structures represented by S-1 to S-39.

Figure pat00006
Figure pat00006

상기한 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 8로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하나, 이에 한정되는 것은 아니다.The compound represented by Chemical Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Chemical Formulas 3 to 8, but is not limited thereto.

[화학식 3](3)

Figure pat00007
Figure pat00007

[화학식 4][Formula 4]

Figure pat00008
Figure pat00008

[화학식 5][Chemical Formula 5]

Figure pat00009
Figure pat00009

[화학식 6][Chemical Formula 6]

Figure pat00010
Figure pat00010

[화학식 7][Formula 7]

Figure pat00011
Figure pat00011

[화학식 8][Formula 8]

Figure pat00012
Figure pat00012

상기 화학식 3 내지 8에서, A, X1 내지 X4, Y1 내지 Y4 , Z1 내지 Z4 , 및 Ar1는 상기 화학식 1에서 정의한 바와 동일하다.In Formulas 3 to 8, A, X 1 to X 4 , Y 1 to Y 4 , Z 1 to Z 4 , and Ar 1 are the same as defined in Formula 1 above.

이러한 본 발명의 화학식 1로 표시되는 화합물은 보다 구체적으로, 하기 화학식 C1 내지 C18로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하나, 이에 한정되는 것은 아니다.More specifically, the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Formulas C1 to C18, but is not limited thereto.

Figure pat00013
Figure pat00013

상기 화학식 C1 내지 C18에서, A, X1 내지 X4 , Z1 내지 Z4 및 Ar1은 상기 화학식 1에서 정의한 바와 동일하다. 상기 화학식 C1 내지 C18로 표시되는 화합물에서 A는 S인 것이 더욱 바람직하다.In Formulas C1 to C18, A, X 1 to X 4 , Z 1 to Z 4 And Ar 1 are the same as defined in formula (I). In the compounds represented by Formulas C1 to C18, A is more preferably S.

이러한 본 발명의 화학식 1로 표시되는 화합물의 구체적인 예로 하기 화합물들(C-1 내지 C-578)을 들 수 있지만, 이에 한정되는 것은 아니다.Specific examples of the compound represented by Formula 1 of the present invention include the following compounds (C-1 to C-578), but is not limited thereto.

Figure pat00014
Figure pat00014

Figure pat00015
Figure pat00015

Figure pat00016
Figure pat00016

Figure pat00017
Figure pat00017

Figure pat00018
Figure pat00018

Figure pat00019
Figure pat00019

Figure pat00020
Figure pat00020

Figure pat00021
Figure pat00021

Figure pat00022
Figure pat00022

Figure pat00023
Figure pat00023

Figure pat00024
Figure pat00024

Figure pat00025
Figure pat00025

Figure pat00026
Figure pat00026

Figure pat00027
Figure pat00027

Figure pat00028
Figure pat00028

Figure pat00029
Figure pat00029

Figure pat00030
Figure pat00030

Figure pat00031
Figure pat00031

Figure pat00032
Figure pat00032

Figure pat00033
Figure pat00033

Figure pat00034
Figure pat00034

이와 같은 본 발명의 화학식 1로 표시되는 화합물은 하기 실시예의 합성과정을 참고하여 다양하게 합성할 수 있다.
Such a compound represented by Formula 1 of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.

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

본 발명은 상기 화학식 1로 표시되는 화합물, 바람직하게는 화학식 3 내지 8로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising a compound represented by Chemical Formula 1, preferably a compound represented by Chemical Formulas 3 to 8.

구체적으로, 본 발명은 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물, 바람직하게는 화학식 3 내지 8로 표시되는 화합물을 포함한다. 이때, 상기 화학식 3 내지 8로 표시되는 화합물은 단독으로 또는 2 이상이 혼합되어 사용될 수 있다.Specifically, the present invention is an organic electroluminescent device comprising an anode (anode), a cathode (cathode) and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic material layer is It includes a compound represented by the formula (1), preferably a compound represented by the formula (3 to 8). In this case, the compounds represented by Formulas 3 to 8 may be used alone or in combination of two or more.

상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 바람직하게는 정공 주입층, 정공수송층, 발광층 또는 전자수송층일 수 있고, 보다 바람직하게는 발광층일 수 있다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, preferably a hole injection layer, a hole transport layer, a light emitting layer or an electron transport layer, more preferably It may be a light emitting layer.

본 발명에 따른 유기 전계 발광 소자는 발광층에 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1로 표시되는 화합물을 사용할 수 있다. 이와 같이, 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층, 바람직하게는 발광층의 청색, 녹색, 적색의 인광 호스트 재료로 사용할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다.The organic electroluminescent device according to the present invention may include a host material in the light emitting layer. In this case, the compound represented by Chemical Formula 1 may be used as the host material. As such, when the compound represented by Chemical Formula 1 is used as a light emitting layer of the organic electroluminescent device, preferably a blue, green, or red phosphorescent host material of the light emitting layer, the binding force between the holes and the electrons in the light emitting layer is increased. The efficiency (light emitting efficiency and power efficiency), lifetime, luminance and driving voltage of the device may be improved.

이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공주입층, 정공수송층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조로 이루어질 수 있다. 여기서, 전자수송층 위에는 전자주입층이 추가로 적층될 수도 있다. 또한, 본 발명에 따른 유기 전계 발광 소자는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조로 이루어질 수도 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be formed of a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked. Here, the electron injection layer may be further stacked on the electron transporting layer. In addition, the organic electroluminescent device according to the present invention may have a structure in which an anode, one or more organic layers and an anode are sequentially stacked, and an insulating layer or an adhesive layer is interposed between the electrodes and the organic layer.

한편, 본 발명에 따른 유기 전계 발광 소자에 포함되는 양극으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 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 등을 사용할 수 있다.On the other hand, the material that can be used as the anode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, 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.

또한, 본 발명에 따른 유기 전계 발광 소자에 포함되는 음극으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 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 등을 사용할 수 있다.In addition, the material that can be used as the cathode included in the organic EL device according to the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, Tin or metals such as lead or alloys thereof; And a multilayer structure material such as LiF / Al or LiO 2 / Al.

또, 본 발명에 따른 유기 전계 발광 소자에 포함되는 유기물층은 상기 화학식 1로 표시되는 화합물을 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나에 사용하는 것을 제외하고는 당업계에 공지된 물질로 이루어질 수 있다.In addition, the organic material layer included in the organic electroluminescent device according to the present invention except for using the compound represented by the formula (1) in any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer It may be made of a material known to the.

본 발명에 따른 유기 전계 발광 소자에 포함되는 기판으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다. Materials that can be used as the substrate included in the organic electroluminescent device according to the present invention are not particularly limited, but examples thereof include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

이와 같은 본 발명의 유기 전계 발광 소자는 당업계에 공지된 방법으로 제조될 수 있으며, 이때, 유기물층에 포함되는 발광층은 진공 증착법이나 용액 도포법으로 제조될 수 있다. 여기서, 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지 않는다.
Such an organic electroluminescent device of the present invention may be manufactured by a method known in the art, wherein the light emitting layer included in the organic material layer may be manufactured by a vacuum deposition method or a solution coating method. Here, examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

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

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

<단계 1> <Step 1> CORE1CORE1 -A의 합성Synthesis of -A

Figure pat00035
Figure pat00035

질소 기류 하에서 10.6g (40.13mmol)의 CORE1-A-1, 8.0g (48.15mmol)의 2-nitrophenylboronic acid, 4.8g (120.4mmol)의 NaOH과 200ml/50ml의 THF/H2O를 넣고 교반하였다. 40℃에서 1.39g (1.2mmol)의 Pd(PPh3)4를 넣고 80℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 CORE1-A 6.4 g (yield: 52%)을 획득하였다. 10.6 g (40.13 mmol) of CORE1-A-1, 8.0 g (48.15 mmol) of 2-nitrophenylboronic acid, 4.8 g (120.4 mmol) of NaOH and 200 ml / 50 ml of THF / H 2 O were added and stirred under a nitrogen stream. . 1.39 g (1.2 mmol) of Pd (PPh 3 ) 4 was added at 40 ° C., and the mixture was stirred under reflux at 80 ° C. for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and then column chromatography was used to obtain 6.4 g (yield: 52%) of CORE1-A.

1H-NMR : δ 7.59 (m, 3H), 8.00 (m, 5H), 8.21 (d, 1H), 8.50 (d, 1H), 1 H-NMR: δ 7.59 (m, 3H), 8.00 (m, 5H), 8.21 (d, 1H), 8.50 (d, 1H),

<단계 2> <Step 2> CORECORE -1의 합성Synthesis of -1

Figure pat00036
Figure pat00036

질소 기류 하에서 CORE1-A 6.4g (20.89mmol)과 triphenylphosphine 13.7g (52.22mmol), 1,2-dichlorobenzene 100ml를 넣은 후 12시간 교반하였다. 반응 종료 후 디스틸레이션을 통해 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층은 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류 한 뒤 컬럼크로마토그래피를 이용하여 CORE-1 3.3g (yield : 57%)을 획득 하였다.Under nitrogen stream, 6.4 g (20.89 mmol) of CORE1-A, 13.7 g (52.22 mmol) of triphenylphosphine, and 100 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed through distillation and extracted with dichloromethane. The extracted organic layer was dried with MgSO 4 and filtered under reduced pressure. After distilling under reduced pressure on the filtered organic layer, 3.3g (yield: 57%) of CORE-1 was obtained by using column chromatography.

1H-NMR : δ 7.31 (t, 1H), 7.55 (m, 4H), 8.05 (m, 3H), 8.82 (s, 1H), 10.51 (s, 1H)
 1 H-NMR: δ 7.31 (t, 1H), 7.55 (m, 4H), 8.05 (m, 3H), 8.82 (s, 1H), 10.51 (s, 1H)

[[ 준비예Preparation Example 2]  2] CORECORE -- 2 의2 of 합성  synthesis

<단계 1> 2,5-<Step 1> 2,5- dichlorodichloro -3-(2--3- (2- chlorophenylchlorophenyl )) pyrazinepyrazine 의 합성Synthesis of

Figure pat00037
Figure pat00037

질소 기류 하에서 28g (152.65mmol)의 2,3,5-trichloropyrazine, 23.8g (152.65mmol)의 2-chlorophenylboronic acid, 63.3g (457.9mmol)의 K2CO3와 800ml/200ml의 THF/H2O를 넣고 교반하였다. 40℃에서 5.3g (4.58mmol)의 Pd(PPh3)4를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 목적 화합물인 2,5-dichloro-3-(2-chlorophenyl)pyrazine 12g (yield: 30%)을 획득하였다. 28 g (152.65 mmol) of 2,3,5-trichloropyrazine, 23.8 g (152.65 mmol) of 2-chlorophenylboronic acid, 63.3 g (457.9 mmol) of K 2 CO 3 and 800 ml / 200 ml of THF / H 2 O under nitrogen stream Was added and stirred. At 40 ℃ into the Pd (PPh 3) 4 of 5.3g (4.58mmol) was stirred at 80 ℃ for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 12 g (yield: 30%) of 2,5-dichloro-3- (2-chlorophenyl) pyrazine was obtained by column chromatography.

1H-NMR : δ 7.37(m, 2H), 7.58(d, 1H), 7.75(d, 1H), 8.69(s, 1H) 1 H-NMR: δ 7.37 (m, 2H), 7.58 (d, 1H), 7.75 (d, 1H), 8.69 (s, 1H)

<단계 2> <Step 2> ethylethyl 3-(2-(3,6- 3- (2- (3,6- dichloropyrazindichloropyrazin -2--2- ylyl )) phenylthio메틸THIO )) propanoatepropanoate 의 합성Synthesis of

Figure pat00038
Figure pat00038

질소 기류 하에서 12g (46.2mmol)의 2,5-dichloro-3-(2-chlorophenyl)pyrazine, 12.4g (92.47mmol)의 ethyl 3-mercaptopropanoate, 2.96g (3.23mmol)의 Pd2dba3, 0.1g (0.7mmol)의 dpephos, 16g (115.6mmol)의 K2CO3를 250ml의 Toluene에 넣고 110℃에서 15시간 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 ethyl 3-(2-(3,6-dichloropyrazin-2-yl)phenylthio)propanoate 14.7g (yield: 89%)을 획득하였다.12 g (46.2 mmol) of 2,5-dichloro-3- (2-chlorophenyl) pyrazine under nitrogen stream, 12.4 g (92.47 mmol) of ethyl 3-mercaptopropanoate, 2.96 g (3.23 mmol) of Pd 2 dba 3 , 0.1 g (0.7 mmol) of dpephos and 16 g (115.6 mmol) of K 2 CO 3 were added to 250 ml of toluene and stirred at 110 ° C. for 15 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and 14.7 g (yield: 89%) of ethyl 3- (2- (3,6-dichloropyrazin-2-yl) phenylthio) propanoate was obtained by column chromatography.

1H-NMR : δ 1.27 (m, 3H), 2.52 (m, 2H), 3.03 (m, 2H), 4.09 (m, 2H), 7.30 (m, 2H), 7.71 (d, 1H), 7.87 (d, 1H), 8.69 (s, 1H) 1 H-NMR: δ 1.27 (m, 3H), 2.52 (m, 2H), 3.03 (m, 2H), 4.09 (m, 2H), 7.30 (m, 2H), 7.71 (d, 1H), 7.87 ( d, 1 H), 8.69 (s, 1 H)

<단계 3> <Step 3> CORE2CORE2 -- A 의Of A 합성 synthesis

Figure pat00039
Figure pat00039

질소 기류 하에서 14.7g (41.1mmol)의 ethyl 3-(2-(3,6-dichloropyrazin-2-yl)phenylthio)propanoate, 6.92g (61.7mmol)의 potassium tert-butoxide를 200ml의 THF에 넣고 50℃에서 8시간 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과 하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 목적 화합물인 CORE2-A 6.6g (yield: 80%)을 획득하였다. Under nitrogen stream, 14.7 g (41.1 mmol) of ethyl 3- (2- (3,6-dichloropyrazin-2-yl) phenylthio) propanoate and 6.92 g (61.7 mmol) of potassium tert-butoxide were added to 200 ml of THF. Stirred for 8 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO 4 and filtered under reduced pressure. After distilling the filtered organic layer under reduced pressure, 6.6 g (yield: 80%) of the target compound was obtained by column chromatography.

1H-NMR : δ 7.51(m, 2H), 8.02(m, 2H), 8.87(s, 1H) 1 H-NMR: δ 7.51 (m, 2H), 8.02 (m, 2H), 8.87 (s, 1H)

<단계 4> <Step 4> CORE2CORE2 -B의 합성Synthesis of -B

Figure pat00040
Figure pat00040

CORE1-A-1 대신 CORE2-A 을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 CORE2-B 6g (yield: 67%)을 획득하였다.A CORE2-B 6g (yield: 67%) was obtained in the same manner as in <Step 1> of Preparation Example 1, except that CORE2-A was used instead of CORE1-A-1.

1H-NMR : δ 7.61(m, 3H), 8.02(m, 4H), 8.18(d, 1H) 1 H-NMR: δ 7.61 (m, 3H), 8.02 (m, 4H), 8.18 (d, 1H)

<단계 5> <Step 5> CORECORE -- 2 의2 of 합성 synthesis

Figure pat00041
Figure pat00041

CORE1-A 대신 CORE2-B를 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 CORE-2 3.2g(yield: 54%)을 얻었다.Except for using CORE2-B instead of CORE1-A was carried out the same procedure as in <Step 2> of Preparation Example 1 to obtain 3.2g (yield: 54%) of CORE-2.

1H-NMR : δ 7.27(t, 1H), 7.59(m, 4H), 8.07(m, 3H) 10.50(s, 1H)
 1 H-NMR: δ 7.27 (t, 1H), 7.59 (m, 4H), 8.07 (m, 3H) 10.50 (s, 1H)

[[ 준비예Preparation Example 3]  3] CORECORE -- 3 의3 of 합성  synthesis

<단계 1> 2,5-<Step 1> 2,5- dichlorodichloro -3-(2--3- (2- chlorophenylchlorophenyl )) pyridine피리딘 의 합성Synthesis of

Figure pat00042
Figure pat00042

2,3,5-trichloropyrazine 대신 2,3,5-trichloropyridine을 사용하는 것을 제외하고는 준비예 2의 <단계 1>과 동일한 과정을 수행하여 2,5-dichloro-3-(2-chlorophenyl)pyridine 13g (yield: 46%)을 획득하였다.2,5-dichloro-3- (2-chlorophenyl) pyridine by following the same procedure as in <Step 1> of Preparation Example 2, except that 2,3,5-trichloropyridine was used instead of 2,3,5-trichloropyrazine. 13g (yield: 46%) was obtained.

1H-NMR : δ 7.38 (m, 2H), 7.75 (m, 2H), 8.81 (s, 1H) 1 H-NMR: δ 7.38 (m, 2H), 7.75 (m, 2H), 8.81 (s, 1H)

<< 단계2Step 2 > > ethylethyl 3-(2-(2,5- 3- (2- (2,5- dichloropyridindichloropyridin -3--3- ylyl )) phenylthio메틸THIO )) propanoatepropanoate 의 합성Synthesis of

Figure pat00043
Figure pat00043

2,5-dichloro-3-(2-chlorophenyl)pyrazine 대신 2,5-dichloro-3-(2-chlorophenyl)pyridine을 사용하는 것을 제외하고는 준비예 2의 <단계 2>와 동일한 과정을 수행하여 ethyl 3-(2-(2,5-dichloropyridin-3-yl)phenylthio)propanoate 15.3g (yield: 85%)을 획득하였다.Except for using 2,5-dichloro-3- (2-chlorophenyl) pyridine instead of 2,5-dichloro-3- (2-chlorophenyl) pyrazine, the same procedure as in <Step 2> of Preparation Example 2 was performed. 15.3 g (yield: 85%) of ethyl 3- (2- (2,5-dichloropyridin-3-yl) phenylthio) propanoate was obtained.

1H-NMR : δ 1.28 (m, 3H), 2.56 (m, 2H), 3.32 (m, 2H), 4.19 (m, 2H), 7.39 (m, 2H), 7.64 (m, 2H), 8.44 (s, 1H), 8.67 (s, 1H) 1 H-NMR: δ 1.28 (m, 3H), 2.56 (m, 2H), 3.32 (m, 2H), 4.19 (m, 2H), 7.39 (m, 2H), 7.64 (m, 2H), 8.44 ( s, 1 H), 8.67 (s, 1 H)

<< 단계3Step 3 > > CORE3CORE3 -A의 합성Synthesis of -A

Figure pat00044
Figure pat00044

ethyl 3-(2-(3,6-dichloropyrazin-2-yl)phenylthio)propanoate 대신 ethyl 3-(2-(2,5-dichloropyridin-3-yl)phenylthio)propanoate을 사용하는 것을 제외하고는 준비예 2의 <단계 3>과 동일한 과정을 수행하여 CORE3-A 7.4g (yield: 78%)을 획득하였다.Preparation example except for using ethyl 3- (2- (2,5-dichloropyridin-3-yl) phenylthio) propanoate instead of ethyl 3- (2- (3,6-dichloropyrazin-2-yl) phenylthio) propanoate CORE3-A 7.4 g (yield: 78%) was obtained by performing the same procedure as in <Step 3> of 2.

1H-NMR : δ 7.48 (m, 2H), 7.96 (m, 2H), 8.49 (d, 1H), 8.81 (s, 1H) 1 H-NMR: δ 7.48 (m, 2H), 7.96 (m, 2H), 8.49 (d, 1H), 8.81 (s, 1H)

<< 단계4Step 4 > > CORE3CORE3 -B의 합성Synthesis of -B

Figure pat00045
Figure pat00045

CORE1-A-1 대신 CORE3-A를 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 CORE3-B 6.2g (yield: 60%)을 획득하였다.6.2g (yield: 60%) of CORE3-B was obtained by performing the same process as <Step 1> of Preparation Example 1, except that CORE3-A was used instead of CORE1-A-1.

1H-NMR : δ 7.49 (m, 2H), 7.66 (t, 1H), 8.01 (m, 4H), 8.19 (d, 1H), 8.43 (d, 1H), 9.36(s, 1H) 1 H-NMR: δ 7.49 (m, 2H), 7.66 (t, 1H), 8.01 (m, 4H), 8.19 (d, 1H), 8.43 (d, 1H), 9.36 (s, 1H)

<< 단계5Step 5 > > CORECORE -3A 및 3B의 합성Synthesis of -3A and 3B

Figure pat00046
Figure pat00046

CORE1-A 대신 CORE3-B 을 사용하는 것을 제외하고는 준비예 1의 <단계 2>과 동일한 과정을 수행하여 CORE-3A 1.8g(yield: 32%) CORE-3B 2.0g(yield: 36%)을 얻었다.CORE-3A 1.8g (yield: 32%) CORE-3B 2.0g (yield: 36%) by following the same procedure as in <Step 2> of Preparation Example 1, except that CORE3-B was used instead of CORE1-A. Got.

CORE-3A 1H-NMR : δ 7.32 (t, 1H), 7.49 (m, 3H), 7.81 (s, 1H), 8.05 (m, 2H), 8.49 (d, 1H), 10.35 (s, 1H)CORE-3A 1 H-NMR: δ 7.32 (t, 1H), 7.49 (m, 3H), 7.81 (s, 1H), 8.05 (m, 2H), 8.49 (d, 1H), 10.35 (s, 1H)

CORE-3B 1H-NMR : δ 7.31 (t, 1H), 7.51 (m, 3H), 7.83 (d, 1H), 8.02 (d, 1H), 8.15 (d, 1H), 8.47 (d, 1H), 9.55(s, 1H) CORE-3B 1 H-NMR: δ 7.31 (t, 1H), 7.51 (m, 3H), 7.83 (d, 1H), 8.02 (d, 1H), 8.15 (d, 1H), 8.47 (d, 1H) , 9.55 (s, 1 H)

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

<단계 1> 3-(2-<Step 1> 3- (2- nitrophenylnitrophenyl )) benzofurobenzofuro [2,3-b][2,3-b] pyridine피리딘 의 합성Synthesis of

Figure pat00047
Figure pat00047

CORE1-A-1 대신 3-chlorobenzofuro[2,3-b]pyridine을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 3-(2-nitrophenyl)benzofuro[2,3-b]pyridine 9.7g (yield: 56%)을 획득하였다.Except for using 3-chlorobenzofuro [2,3-b] pyridine instead of CORE1-A-1, the same procedure as in <Step 1> of Preparation Example 1 was carried out to give 3- (2-nitrophenyl) benzofuro [2,3 -b] pyridine 9.7g (yield: 56%) was obtained.

1H-NMR : δ 7.34 (m, 2H), 7.66 (m, 2H), 7.95 (m, 4H), 8.18 (d, 1H), 9.50 (s, 1H) 1 H-NMR: δ 7.34 (m, 2H), 7.66 (m, 2H), 7.95 (m, 4H), 8.18 (d, 1H), 9.50 (s, 1H)

<단계 2> <Step 2> CORECORE -4A 및 4B의 합성Synthesis of -4A and 4B

Figure pat00048
Figure pat00048

CORE1-A 대신 3-(2-nitrophenyl)benzofuro[2,3-b]pyridine을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 CORE-4A 2.8g(yield: 32%), CORE-4B 3.0g (yield: 35%)을 얻었다.Except for using 3- (2-nitrophenyl) benzofuro [2,3-b] pyridine instead of CORE1-A, the same procedure as in <Step 2> of Preparation Example 1 was performed to obtain 2.8 g of CORE-4A (yield: 32). %), CORE-4B 3.0g (yield: 35%) was obtained.

CORE-4A 1H-NMR : δ 7.34 (m, 3H), 7.50 (t, 1H), 7.65 (m, 2H), 7.80 (s, 1H), 7.92 (d, 1H), 8.15(d, 1H), 10.45(s, 1H)CORE-4A 1 H-NMR: δ 7.34 (m, 3H), 7.50 (t, 1H), 7.65 (m, 2H), 7.80 (s, 1H), 7.92 (d, 1H), 8.15 (d, 1H) , 10.45 (s, 1H)

CORE-4B 1H-NMR : δ 7.32 (m, 3H), 7.49 (t, 1H), 7.64 (m, 2H), 7.89 (d, 1H), 8.13 (d, 1H), 9.53(s, 1H), 10.42(s, 1H)
CORE-4B 1 H-NMR: δ 7.32 (m, 3H), 7.49 (t, 1H), 7.64 (m, 2H), 7.89 (d, 1H), 8.13 (d, 1H), 9.53 (s, 1H) , 10.42 (s, 1H)

[[ 합성예Synthetic example 1]  One] MatMat -1의 합성Synthesis of -1

Figure pat00049
Figure pat00049

질소 기류 하에서 준비예 1에서 제조한 화합물인 CORE-1 (3.28g, 12.00mmol), 1-bromo-3,5-diphenylbenzene (7.39g, 24.00mmol), Cu powder(0.09g, 1.30mmol), K2CO3(3.58g, 26.00mmol), Na2SO4(3.70g, 26.00mmol) 및 nitrobenzene(100ml)를 혼합하고 190℃에서 12시간 동안 교반하였다. CORE-1 (3.28g, 12.00mmol), 1-bromo-3,5-diphenylbenzene (7.39g, 24.00mmol), Cu powder (0.09g, 1.30mmol), K which is a compound prepared in Preparation Example 1 under nitrogen stream 2 CO 3 (3.58 g, 26.00 mmol), Na 2 SO 4 (3.70 g, 26.00 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours.

반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 Mat-1 (4.22g, 수율 70%)을 얻었다.After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound Mat-1 (4.22g, 70% yield).

Exact Mass: 502.15g/molExact Mass: 502.15 g / mol

Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38
Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38

[[ 합성예Synthetic example 2]  2] MatMat -2의 합성Synthesis of -2

Figure pat00050
Figure pat00050

1-bromo-3,5-diphenylbenzene 대신 2-bromo-4,6-diphenylpyridine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-2 (4.04g, 수율 67%)을 얻었다.Except for using 2-bromo-4,6-diphenylpyridine instead of 1-bromo-3,5-diphenylbenzene, the same procedure as in Synthesis Example 1 was carried out to obtain Mat-2 (4.04 g, yield 67%) as a target compound. Got it.

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37
Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37

[[ 합성예Synthetic example 3]  3] MatMat -3의 합성Synthesis of -3

Figure pat00051
Figure pat00051

질소 기류 하에서 준비예 1에서 제조한 화합물인 CORE-1 (3.28g, 12.00mmol), 2-chloro-4,6-diphenylpyrimidine (6.38g, 24.00mmol), NaH (3.45g, 14.40mmol) 및 DMF(80ml)를 혼합하고 상온에서 3시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 Mat-3 (4.89g, 수율 81%)를 얻었다.CORE-1 (3.28g, 12.00mmol), 2-chloro-4,6-diphenylpyrimidine (6.38g, 24.00mmol), NaH (3.45g, 14.40mmol) and DMF (Compounds prepared in Preparation Example 1) under nitrogen stream 80 ml) was mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Mat-3 (4.89 g, yield 81%) as a target compound.

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35
Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[[ 합성예Synthetic example 4]  4] MatMat -4의 합성Synthesis of -4

Figure pat00052
Figure pat00052

2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-4 4.84g, 수율 80%)을 얻었다.Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenylpyrimidine, the same procedure as in Synthesis Example 3 was carried out, thereby the target compound Mat-4 4.84 g, yield 80%) was obtained.

Exact Mass: 505g/molExact Mass: 505g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34
Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[[ 합성예Synthetic example 5]  5] MatMat -5의 합성Synthesis of -5

Figure pat00053
Figure pat00053

2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-5 (5.99g, 수율 76%)을 얻었다.Except for using 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of 2-chloro-4,6-diphenylpyrimidine Mat-5 (5.99g, yield 76%) was obtained as the target compound.

Exact Mass: 657.20g/molExact Mass: 657.20 g / mol

Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87
Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87

[[ 합성예Synthetic example 6]  6] MatMat -6의 합성Synthesis of -6

Figure pat00054
Figure pat00054

1-bromo-3,5-diphenylbenzene 대신 3-bromo-9-phenyl-9H-carbazole을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-6 (4.38g, 수율 71%)을 얻었다.Except for using 3-bromo-9-phenyl-9H-carbazole instead of 1-bromo-3,5-diphenylbenzene, the same procedure as in Synthesis Example 1 was performed, thereby obtaining Mat-6 (4.38g, 71% yield). )

Exact Mass: 515.15g/molExact Mass: 515.15 g / mol

Elemental Analysis: C, 81.53; H, 4.11; N, 8.15; S, 6.22
Elemental Analysis: C, 81.53; H, 4.11; N, 8. 15; S, 6.22

[[ 합성예Synthetic example 7]  7] MatMat -7의 합성Synthesis of -7

Figure pat00055
Figure pat00055

1-bromo-3,5-diphenylbenzene 대신 2-bromo-5-phenylpyridine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-7 (3.48g, 수율 68%)을 얻었다.Except for using 2-bromo-5-phenylpyridine instead of 1-bromo-3,5-diphenylbenzene was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-7 (3.48g, 68% yield).

Exact Mass: 427.11g/molExact Mass: 427.11 g / mol

Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50
Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50

[[ 합성예Synthetic example 8]  8] MatMat -8의 합성Synthesis of -8

Figure pat00056
Figure pat00056

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-8 (4.22g, 수율 70%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-8 (4.22g, yield 70%).

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37
Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37

[[ 합성예Synthetic example 9]  9] MatMat -9의 합성Synthesis of -9

Figure pat00057
Figure pat00057

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Mat-9 (3.93g, 수율 65%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound Mat-9 (3.93g, yield 65%).

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35
Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[[ 합성예Synthetic example 10]  10] MatMat -10의 합성Synthesis of -10

Figure pat00058
Figure pat00058

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-10 (4.48g, 수율 74%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Mat-10 (4.48g, 74% yield).

Exact Mass: 505.14g/molExact Mass: 505.14 g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34
Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[[ 합성예Synthetic example 11]  11] MatMat -11의 합성Synthesis of -11

Figure pat00059
Figure pat00059

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-11 (4.31g, 수율 71%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-11 (4.31g, 71% yield).

Exact Mass: 506.13g/molExact Mass: 506.13 g / mol

Elemental Analysis: C, 73.50; H, 3.58; N, 16.59; S, 6.33
Elemental Analysis: C, 73.50; H, 3.58; N, 16.59; S, 6.33

[[ 합성예Synthetic example 12]  12] MatMat -12의 합성Synthesis of -12

Figure pat00060
Figure pat00060

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-12 (5.92g, 수율 75%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-12 (5.92g, yield 75%).

Exact Mass: 658.19g/molExact Mass: 658.19 g / mol

Elemental Analysis: C, 78.40; H, 3.98; N, 12.76; S, 4.87
Elemental Analysis: C, 78.40; H, 3.98; N, 12.76; S, 4.87

[[ 합성예Synthetic example 13]  13] MatMat -13의 합성Synthesis of -13

Figure pat00061
Figure pat00061

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-13 (4.08g, 수율 66%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-13 (4.08g, 66% yield).

Exact Mass: 516.14g/molExact Mass: 516.14 g / mol

Elemental Analysis: C, 79.05; H, 3.90; N, 10.84; S, 6.21
Elemental Analysis: C, 79.05; H, 3.90; N, 10.84; S, 6.21

[[ 합성예Synthetic example 14]  14] MatMat -14의 합성Synthesis of -14

Figure pat00062
Figure pat00062

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 7과 동일한 과정을 수행하여 목적 화합물인 Mat-14 (3.23g, 수율 63%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound Mat-14 (3.23g, 63% yield).

Exact Mass: 428.11g/molExact Mass: 428.11 g / mol

Elemental Analysis: C, 75.68; H, 3.76; N, 13.07; S, 7.48
Elemental Analysis: C, 75.68; H, 3.76; N, 13.07; S, 7.48

[[ 합성예Synthetic example 15]  15] MatMat -15의 합성Synthesis of -15

Figure pat00063
Figure pat00063

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-15 (4.21g, 수율 70%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-15 (4.21g, 70% yield).

Exact Mass: 502.15g/molExact Mass: 502.15 g / mol

Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38
Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38

[[ 합성예Synthetic example 16]  16] MatMat -16의 합성Synthesis of -16

Figure pat00064
Figure pat00064

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Mat-16 (3.62g, 수율 60%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound Mat-16 (3.62g, yield 60%).

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37
Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37

[[ 합성예Synthetic example 17]  17] MatMat -17의 합성Synthesis of -17

Figure pat00065
Figure pat00065

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-17 (4.53g, 수율 75%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Mat-17 (4.53g, yield 75%).

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35
Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[[ 합성예Synthetic example 18]  18] MatMat -18의 합성Synthesis of -18

Figure pat00066
Figure pat00066

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-18 (4.36g, 수율 72%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-18 (4.36g, 72% yield).

Exact Mass: 505.14g/molExact Mass: 505.14 g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34
Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[[ 합성예Synthetic example 19]  19] MatMat -19의 합성-19 Synthesis

Figure pat00067
Figure pat00067

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-19 (5.51g, 수율 70%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-19 (5.51g, yield 70%).

Exact Mass: 657.20 g/molExact Mass: 657.20 g / mol

Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87
Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87

[[ 합성예Synthetic example 20]  20] MatMat -20의 합성Synthesis of -20

Figure pat00068
Figure pat00068

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-20 (3.98g, 수율 63%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-20 (3.98g, 63% yield).

Exact Mass: 515.15g/molExact Mass: 515.15 g / mol

Elemental Analysis: C, 81.53; H, 4.11; N, 8.15; S, 6.22
Elemental Analysis: C, 81.53; H, 4.11; N, 8. 15; S, 6.22

[[ 합성예Synthetic example 21]  21] MatMat -21의 합성Synthesis of -21

Figure pat00069
Figure pat00069

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 7과 동일한 과정을 수행하여 목적 화합물인 Mat-21 (3.33g, 수율 65%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound Mat-21 (3.33g, 65% yield).

Exact Mass: 427.11g/molExact Mass: 427.11 g / mol

Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50
Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50

[[ 합성예Synthetic example 22]  22] MatMat -22의 합성Synthesis of -22

Figure pat00070
Figure pat00070

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-22 (4.33g, 수율 72%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-22 (4.33g, 72% yield).

Exact Mass: 502.15g/molExact Mass: 502.15 g / mol

Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38
Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38

[[ 합성예Synthetic example 23]  23] MatMat -23의 합성Synthesis of -23

Figure pat00071
Figure pat00071

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Mat-23 (3.92g, 수율 65%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound Mat-23 (3.92g, 65% yield).

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37
Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37

[[ 합성예Synthetic example 24]  24] MatMat -24의 합성Synthesis of -24

Figure pat00072
Figure pat00072

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-24 (4.23g, 수율 70%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Mat-24 (4.23g, 70% yield).

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35
Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[[ 합성예Synthetic example 25]  25] MatMat -25의 합성Synthesis of -25

Figure pat00073
Figure pat00073

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-25 (4.24g, 수율 70%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-25 (4.24g, 70% yield).

Exact Mass: 505.14g/molExact Mass: 505.14 g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34
Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[[ 합성예Synthetic example 26]  26] MatMat -26의 합성Synthesis of -26

Figure pat00074
Figure pat00074

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-26 (5.36g, 수율 68%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-26 (5.36g, yield 68%).

Exact Mass: 657.20g/molExact Mass: 657.20 g / mol

Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87
Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87

[[ 합성예Synthetic example 27]  27] MatMat -27의 합성-27

Figure pat00075
Figure pat00075

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-27 (4.02g, 수율 65%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-27 (4.02g, 65% yield).

Exact Mass: 515.15g/molExact Mass: 515.15 g / mol

Elemental Analysis: C, 81.53; H, 4.11; N, 8.15; S, 6.22
Elemental Analysis: C, 81.53; H, 4.11; N, 8. 15; S, 6.22

[[ 합성예Synthetic example 28]  28] MatMat -28의 합성-28 Synthesis

Figure pat00076
Figure pat00076

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 7과 동일한 과정을 수행하여 목적 화합물인 Mat-28 (3.12g, 수율 61%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound Mat-28 (3.12g, 61% yield).

Exact Mass: 427.11g/molExact Mass: 427.11 g / mol

Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50
Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50

[[ 합성예Synthetic example 29]  29] MatMat -29의 합성Synthesis of -29

Figure pat00077
Figure pat00077

CORE-1 대신 CORE-4A를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-29 (4.24g, 수율 70%)을 얻었다.Except for using CORE-4A instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-29 (4.24g, 70% yield).

Exact Mass: 489.16g/molExact Mass: 489.16 g / mol

Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27
Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27

[[ 합성예Synthetic example 30]  30] MatMat -30의 합성Synthesis of -30

Figure pat00078
Figure pat00078

CORE-1 대신 CORE-4A를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-30 (5.00g, 수율 65%)을 얻었다.Except for using CORE-4A instead of CORE-1 was carried out the same procedure as in Synthesis Example 5 to obtain the target compound Mat-30 (5.00g, yield 65%).

Exact Mass: 641.22g/molExact Mass: 641.22 g / mol

Elemental Analysis: C, 82.35; H, 4.24; N, 10.91; O, 2.49
Elemental Analysis: C, 82.35; H, 4.24; N, 10.91; O, 2.49

[[ 합성예Synthetic example 31]  31] MatMat -31의 합성Synthesis of -31

Figure pat00079
Figure pat00079

CORE-1 대신 CORE-4A를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-31 (3.77g, 수율 63%)을 얻었다.Except for using CORE-4A instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-31 (3.77g, 63% yield).

Exact Mass: 499.17g/molExact Mass: 499.17 g / mol

Elemental Analysis: C, 84.15; H, 4.24; N, 8.41; O, 3.20
Elemental Analysis: C, 84.15; H, 4.24; N, 8.41; , 3.20

[[ 합성예Synthetic example 32]  32] MatMat -32의 합성Synthesis of -32

Figure pat00080
Figure pat00080

CORE-1 대신 CORE-4B를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-32 (4.34g, 수율 74%)을 얻었다.Except for using CORE-4B instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-32 (4.34g, 74% yield).

Exact Mass: 489.16g/molExact Mass: 489.16 g / mol

Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27
Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27

[[ 합성예Synthetic example 33]  33] MatMat -33의 합성Synthesis of -33

Figure pat00081
Figure pat00081

CORE-1 대신 CORE-4B를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-33 (5.38g, 수율 70%)을 얻었다.Except for using CORE-4B instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-33 (5.38g, yield 70%).

Exact Mass: 641.22g/molExact Mass: 641.22 g / mol

Elemental Analysis: C, 82.35; H, 4.24; N, 10.91; O, 2.49
Elemental Analysis: C, 82.35; H, 4.24; N, 10.91; O, 2.49

[[ 합성예Synthetic example 34]  34] MatMat -34의 합성Synthesis of -34

Figure pat00082
Figure pat00082

CORE-1 대신 CORE-4B를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-34 (4.07g, 수율 68%)을 얻었다.Except for using CORE-4B instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-34 (4.07g, yield 68%).

Exact Mass: 499.17g/molExact Mass: 499.17 g / mol

Elemental Analysis: C, 84.15; H, 4.24; N, 8.41; O, 3.20
Elemental Analysis: C, 84.15; H, 4.24; N, 8.41; , 3.20

[[ 실시예Example 1] 녹색 유기  1] Green Organic 전계Field 발광 소자의 제작 Fabrication of light emitting device

합성예 1에서 합성된 화합물 Mat-1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 녹색 유기 전계 발광 소자를 제조하였다.The compound Mat-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured as follows.

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

상기와 같이 준비된 ITO 투명 전극 위에, 합성예 1의 화합물 Mat-1를 호스트로 이용하여, m-MTDATA(60 nm) / TCTA(80 nm) / 화합물 Mat-1 + 10 % Ir(ppy)3(300nm) / BCP(10 nm) / Alq3(30 nm) / LiF(1 nm) / Al(200 nm) 순으로 적층하여 녹색 유기 전계 발광 소자를 제작하였다.On the prepared ITO transparent electrode, using the compound Mat-1 of Synthesis Example 1 as a host, m-MTDATA (60 nm) / TCTA (80 nm) / compound Mat-1 + 10% Ir (ppy) 3 ( 300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in order to produce a green organic electroluminescent device.

사용된 m-MTDATA, TCTA, Ir(ppy)3 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP used are as follows.

Figure pat00083
Figure pat00083

Figure pat00084

Figure pat00084

[[ 실시예Example 2 ~ 34] 2 to 34]

실시예 1에서 발광층 형성시 발광 호스트 물질로서 사용된 화합물 Mat-1 대신 합성예 2 내지 34에서 각각 합성된 화합물 Mat-2 내지 Mat-34를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.
The same procedure as in Example 1 was repeated except that Compounds Mat-2 to Mat-34 synthesized in Synthesis Examples 2 to 34 were used instead of Compound Mat-1 used as a light emitting host material in Example 1 to form a light emitting layer. To produce a green organic electroluminescent device.

[[ 비교예Comparative Example 1] One]

실시예 1에서 발광층 형성시 발광 호스트 물질로서 사용된 화합물 Mat-1 대신 CBP를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제작하였다. 사용된 CBP의 구조는 하기와 같다.A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat-1 used as the light emitting host material in forming the light emitting layer in Example 1. The structure of CBP used is as follows.

Figure pat00085
Figure pat00085

[[ 실험예Experimental Example ]]

실시예 1 내지 34 및 비교예 1에서 각각 제조된 녹색 유기 전계 발광 소자에 대하여, 전류밀도 10mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For green organic electroluminescent devices prepared in Examples 1 to 34 and Comparative Example 1, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

샘플Sample 호스트Host 구동 전압
(V)Driving voltage
(V) 발광 피크
(nm)Emission peak
(nm) 전류효율
(cd/A)Current efficiency
(cd / A) 실시예 1Example 1 Mat-1Mat-1 6.506.50 520520 41.041.0 실시예 2Example 2 Mat-2Mat-2 6.616.61 523523 41.241.2 실시예 3Example 3 Mat-3Mat-3 6.606.60 523523 40.840.8 실시예 4Example 4 Mat-4Mat-4 6.586.58 523523 41.141.1 실시예 5Example 5 Mat-5Mat-5 6.706.70 522522 41.841.8 실시예 6Example 6 Mat-6Mat-6 6.706.70 520520 41.341.3 실시예 7Example 7 Mat-7Mat-7 6.516.51 521521 41.441.4 실시예 8Example 8 Mat-8Mat-8 6.666.66 520520 40.940.9 실시예 9Example 9 Mat-9Mat-9 6.506.50 520520 41.041.0 실시예 10Example 10 Mat-10Mat-10 6.456.45 519519 41.541.5 실시예 11Example 11 Mat-11Mat-11 6.606.60 521521 41.341.3 실시예 12Example 12 Mat-12Mat-12 6.556.55 518518 41.141.1 실시예 13Example 13 Mat-13Mat-13 6.706.70 520520 41.241.2 실시예 14Example 14 Mat-14Mat-14 6.506.50 523523 41.341.3 실시예 15Example 15 Mat-15Mat-15 6.646.64 520520 41.141.1 실시예 16Example 16 Mat-16Mat-16 6.606.60 522522 41.541.5 실시예 17Example 17 Mat-17Mat-17 6.626.62 522522 40.940.9 실시예 18Example 18 Mat-18Mat-18 6.706.70 520520 41.441.4 실시예 19Example 19 Mat-19Mat-19 6.646.64 520520 41.041.0 실시예 20Example 20 Mat-20Mat-20 6.506.50 521521 41.641.6 실시예 21Example 21 Mat-21Mat-21 6.706.70 520520 41.541.5 실시예 22Example 22 Mat-22Mat-22 6.636.63 521521 41.041.0 실시예 23Example 23 Mat-23Mat-23 6.706.70 522522 40.940.9 실시예 24Example 24 Mat-24Mat-24 6.556.55 520520 41.841.8 실시예 25Example 25 Mat-25Mat-25 6.656.65 519519 40.940.9 실시예 26Example 26 Mat-26Mat-26 6.606.60 521521 41.141.1 실시예 27Example 27 Mat-27Mat-27 6.656.65 520520 41.541.5 실시예 28Example 28 Mat-28Mat-28 6.526.52 521521 41.441.4 실시예 29Example 29 Mat-29Mat-29 6.796.79 520520 39.839.8 실시예 30Example 30 Mat-30Mat-30 6.756.75 519519 39.539.5 실시예 31Example 31 Mat-31Mat-31 6.706.70 520520 39.039.0 실시예 32Example 32 Mat-32Mat-32 6.816.81 521521 39.239.2 실시예 33Example 33 Mat-33Mat-33 6.756.75 521521 39.539.5 실시예 34Example 34 Mat-34Mat-34 6.806.80 520520 39.739.7 비교예 1Comparative Example 1 CBPCBP 6.936.93 516516 38.238.2

상기 표 1을 살펴보면 본 발명의 화학식 1로 표시되는 화합물(화합물 Mat-1 내지 Mat-34)을 발광층의 호스트 물질로 사용하는 실시예 1 내지 34에서 각각 제조된 녹색 유기 전계 발광 소자는 종래 CBP를 사용하는 비교예 1의 녹색 유기 전계 발광 소자보다 전류효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.Referring to Table 1, the green organic electroluminescent devices manufactured in Examples 1 to 34, which use the compounds represented by Chemical Formula 1 of the present invention (Compounds Mat-1 to Mat-34) as host materials of the light emitting layer, respectively, have conventional CBP. It was confirmed that the green organic electroluminescent device of Comparative Example 1 used exhibited superior performance in terms of current efficiency and driving voltage.

Claims (8)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure pat00086

상기 화학식 1에서,
A는 O 또는 S이고,
X1 내지 X4는, 각각 독립적으로, CR1 또는 N이고,
Y1과 Y2, Y2와 Y3, Y3와 Y4 중 하나는 하기 화학식 2로 표시되는 화합물과 축합 고리를 형성하고, Y1 내지 Y4 중 축합 고리를 형성하지 않는 것은 CR2 또는 N이고, 이때, N을 반드시 포함하며,
[화학식 2]
Figure pat00087

상기 화학식 2에서,
Z1 내지 Z4는, 각각 독립적으로, CR3 또는 N이고,
상기 R1 내지 R3는, 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, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 인접하는 기와 결합하여 축합(fused) 고리를 형성할 수 있으며,
상기 Ar1은 수소, 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, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,
상기 R1 내지 R3 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 아릴알킬기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 및 아릴실릴기는 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, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있으며, 치환될 때 각각의 치환기는 동일하거나 상이하다.A compound represented by the following formula (1):
[Formula 1]
Figure pat00086

In Chemical Formula 1,
A is O or S,
X 1 to X 4 are each independently CR 1 or N,
One of Y 1 and Y 2 , Y 2 and Y 3 , Y 3 and Y 4 forms a condensed ring with the compound represented by the following formula (2), and Y 1 to Y 4 It is CR 2 or N that does not form a heavy condensed ring, in which case it must include N,
(2)
Figure pat00087

In Formula 2,
Z 1 to Z 4 are each independently CR 3 or N,
R 1 to R 3 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- C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, (C 6 - of C 40 aryl) C of 1 - C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 of Selected from the group consisting of arylsilyl groups, and bonded to adjacent groups to form a fused ring. Can be formed,
Ar 1 is hydrogen, 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 5 to 40 heteroaryl C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, (C 6 -C 40 aryl) C 1 -C 40 alkyl group, C of 3 ~ C 40 cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, an aryl group is selected from the group consisting of silyl C 1 ~ C 40 alkylsilyl group and a C 6 ~ C 40,
The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R 1 to R 3 and Ar 1 , And arylsilyl groups are 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 aryl group, nuclear atom number 5 to 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, (C 6 to C 40 aryl) C 1 ~ one member selected from the group consisting of C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, and a C 6 ~ with an aryl silyl group of C 40 of It may be substituted or unsubstituted with the above substituents, and each substituent is the same or different when substituted. 제1항에 있어서,
상기 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 8로 표시되는 화합물로 이루어진 군에서 선택된 것이 특징인 화합물:
[화학식 3]
Figure pat00088

[화학식 4]
Figure pat00089

[화학식 5]
Figure pat00090

[화학식 6]
Figure pat00091

[화학식 7]
Figure pat00092

[화학식 8]
Figure pat00093

상기 화학식 3 내지 8에서,
A, X1 내지 X4, Y1 내지 Y4 , Z1 내지 Z4 및 Ar1은 제1항에서 정의된 바와 동일하다.The method of claim 1,
Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of compounds represented by the following formulas 3 to 8:
(3)
Figure pat00088

[Chemical Formula 4]
Figure pat00089

[Chemical Formula 5]
Figure pat00090

[Chemical Formula 6]
Figure pat00091

(7)
Figure pat00092

[Chemical Formula 8]
Figure pat00093

In the above Formulas 3 to 8,
A, X 1 to X 4 , Y 1 to Y 4 , Z 1 to Z 4 And Ar &lt; 1 &gt; are as defined in claim 1 . 제1항에 있어서,
상기 화학식 1로 표시되는 화합물은 하기 화학식 C1 내지 C18로 표시되는 화합물로 이루어진 군에서 선택된 것이 특징인 화합물:
Figure pat00094

상기 화학식 C1 내지 C18에서,
A, X1 내지 X4 , Z1 내지 Z4 및 Ar1은 제1항에서 정의된 바와 동일하다.The method of claim 1,
Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of compounds represented by the formula C1 to C18:
Figure pat00094

In Chemical Formulas C1 to C18,
A, X 1 to X 4 , Z 1 to Z 4 And Ar &lt; 1 &gt; are as defined in claim 1 . 제3항에 있어서,
상기 A는 S인 것이 특징인 화합물.The method of claim 3,
A is a compound characterized in that S. 제1항에 있어서,
상기 Ar1은, 치환 혹은 비치환의 C6~C40의 아릴기 또는 치환 혹은 비치환의 핵원자수 5 내지 40의 헤테로아릴기인 것이 특징인 화합물. The method of claim 1,
Ar 1 is a substituted or unsubstituted C 6 -C 40 aryl group or a substituted or unsubstituted heteroaryl group having 5 to 40 nuclear atoms. 제1항에 있어서,
상기 Ar1은, 하기 S-1 내지 S-39로 표시되는 구조로 이루어진 군에서 선택되는 것이 특징인 화합물:
Figure pat00095
The method of claim 1,
Ar 1 is a compound, characterized in that selected from the group consisting of the structures represented by S-1 to S-39:
Figure pat00095
 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자에 있어서,
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 것이 특징인 유기 전계 발광 소자.1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
Wherein at least one of the one or more organic layers includes a compound according to any one of claims 1 to 6. 제7항에 있어서,
상기 제1항 내지 제6항 중 어느 한 항에 따른 화합물을 포함하는 유기물층은 발광층인 것이 특징인 유기 전계 발광 소자.The method of claim 7, wherein
The organic electroluminescent device characterized in that the organic material layer containing the compound according to any one of claims 1 to 6 is a light emitting layer.
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