KR20160041675A - Organic compound and organic electroluminescent device using the same - Google Patents

Organic compound and organic electroluminescent device using the same Download PDF

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KR20160041675A
KR20160041675A KR1020140136100A KR20140136100A KR20160041675A KR 20160041675 A KR20160041675 A KR 20160041675A KR 1020140136100 A KR1020140136100 A KR 1020140136100A KR 20140136100 A KR20140136100 A KR 20140136100A KR 20160041675 A KR20160041675 A KR 20160041675A
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김충한
이주형
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주식회사 두산
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    • C07—ORGANIC CHEMISTRY
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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Abstract

The present invention relates to an organic compound and an organic electroluminescent device comprising the same. The compound according to the present invention can be used to an organic layer of an organic electroluminescent device, preferably, an electron transport layer, a luminous layer, or a hole injection layer, and thus can enhance luminous efficiency, driving voltage, lifespan, etc., of the organic electroluminescent device. The organic compound of the present invention is represented by chemical formula 1.

Description

유기 화합물 및 이를 이용한 유기 전계 발광 소자{ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME}TECHNICAL FIELD [0001] The present invention relates to an organic compound and an organic electroluminescent device using the organic compound.

본 발명은 신규한 유기 발광 화합물 및 상기 화합물을 포함하는 유기 전계 발광 소자에 관한 것으로, 보다 상세하게는 발광 효율이 좋고 재료의 수명특성이 우수한 신규 벤조트리이미다졸계 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 구동전압이 낮고, 발광효율, 열적 안정성 및 수명이 향상된 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the compound. More particularly, the present invention relates to a novel benzotriimidazole-based compound having good luminescence efficiency and excellent lifetime characteristics of a material, To an organic electroluminescent device having a low driving voltage and improved luminous efficiency, thermal stability and lifetime.

일반적으로 유기 발광 현상이란 유기 물질에 전기에너지를 가했을 때 빛이 나타나는 현상을 말한다. 즉, 양극(anode)과 음극(cathode) 사이에 유기물층을 위치시켰을 때 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되고, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다.Generally, an organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material. That is, when a voltage is applied between the two electrodes when the organic layer is positioned between the anode and the cathode, holes are injected into the organic layer and holes are injected into the organic layer. When the injected holes and electrons meet, an exciton is formed. When the exciton falls back to the ground state, light is emitted.

유기 전계 발광 소자를 효율적으로 만들기 위한 한 방법으로서 소자 내의 유기물층을 단층 대신 다층 구조로 제조하는 연구가 진행되어 왔다. 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었으며, 현재 사용되는 대부분의 유기 전계 발광 소자는 기판, 양극, 양극으로 정공을 받아들이는 정공 주입층, 정공을 전달하는 정공 전달층, 정공과 전자가 재결합하여 빛을 내는 발광층, 전자를 전달하는 전자 전달층, 음극으로부터 전자를 받아들이는 전자 주입층 및 음극으로 이루어져 있다. 이렇게 유기 전계 발광 소자를 다층으로 제작하는 이유는 정공과 전자의 이동속도가 상이하며, 따라서 적절한 정공 주입층 및 전달층, 전자 전달층 및 전자 주입층을 만들어 주면 정공과 전자가 효과적으로 전달될 수 있으며, 소자 내 정공과 전자의 균형이 이루어져 발광 효율을 높일 수 있기 때문이다. As a method for efficiently making an organic electroluminescent device, research has been conducted to manufacture an organic material layer in a device in a multilayer structure instead of a single layer. In 1987, an organic electroluminescent device having a multilayer structure divided into a hole layer and a functional layer of a light emitting layer by Tang has been proposed. Most organic electroluminescent devices currently used include a hole injecting hole Layer, a hole transporting layer for transporting holes, a light emitting layer for recombining holes and electrons to emit light, an electron transporting layer for transporting electrons, an electron injecting layer for receiving electrons from the cathode, and a cathode. The reason why the organic electroluminescent devices are formed in a multi-layer structure is that the moving speeds of holes and electrons are different from each other. Therefore, when an appropriate hole injecting layer, a transfer layer, an electron transporting layer and an electron injecting layer are formed, holes and electrons can be effectively transferred , And a balance between the holes and electrons in the device can be made to improve the luminous efficiency.

전자 수송의 재료에 관한 최초의 보고는 옥사디아졸 유도체(PBD)를 들 수 있다. 이후 트리아졸 유도체(TAZ) 및 페난스로린 유도체(BCP)가 전자 수송성을 나타낸다고 보고 되었다. 전자 수송층은 유기 단분자 물질로는 전자에 대한 안정도와 전자 이동 속도가 상대적으로 우수한 유기 금속착제들이 좋은 후보들이며, 안정성이 우수하고 전자 친화도가 큰 Alq3가 가장 우수한 것으로 보고 되었으며, 현재에도 가장 기본적으로 사용되고 있다. The first reports on the materials of electron transport include oxadiazole derivatives (PBD). It has been reported that the triazole derivative (TAZ) and the phenanthroline derivative (BCP) exhibit electron transportability. Organic metal complexes, which have relatively high stability and electron transfer rate, are good candidates for the electron transport layer. Alq 3, which has excellent stability and high electron affinity, It is basically used.

또한, 종래의 전자 주입 및 수송층용 물질로는 이미다졸기, 옥사졸기, 티아졸기를 가진 유기 단분자 물질들이 많이 보고되었다. 그러나 이러한 물질들이 전자수송용 물질로 보고되기 이전에 모토롤라(Motorola)사의 EU0700917 A2에 이러한 물질들의 금속착체 화합물들이 유기 발광 소자의 청색 발광층 또는 청록색 발광층에 적용된 것이 이미 보고되었다.In addition, organic single molecule materials having an imidazole group, an oxazole group and a thiazole group have been reported as materials for the conventional electron injection and transport layer. However, it has been reported that metal complex compounds of these materials are applied to a blue light emitting layer or a cyan light emitting layer of an organic light emitting device in Motorola's EU0700917 A2 before these materials are reported as materials for electron transporting.

1996년도에 코닥사에서 발표하고 미국 특허 제5,645,948호에 기재된 TPBI는 이미다졸기를 가진 대표적인 전자 수송층용 물질로 알려져 있으며, 그 구조는 벤젠의 1,3,5 치환 위치에 세 개의 N-페닐 벤즈이미다졸기를 함유하고 기능적으로는 전자를 전달하는 능력뿐 아니라 발광층에서 넘어오는 정공을 차단하는 기능도 있으나, 실제 소자에 적용하기에는 열적 안정성이 낮은 문제점을 가지고 있다.TPBI disclosed in Kodak Company in 1996 and disclosed in U.S. Patent No. 5,645,948 is known as a typical electron transport layer material having an imidazole group and its structure is composed of three N-phenylbenzene It has an ability to block an electron passing through the light emitting layer as well as an ability to transfer electrons functionally containing an imidazole group, but has a low thermal stability to be applied to an actual device.

따라서, 상기와 같은 종래 기술의 문제점을 극복하고 유기 전계 발광 소자의 특성을 더욱 향상시키기 위하여, 유기 전계 발광 소자에서 전자 주입 및 수송용 물질로 사용될 수 있는 보다 안정적이고 효율적인 재료에 대한 개발이 계속 요구된다.Therefore, in order to overcome the problems of the prior art and further improve the characteristics of the organic electroluminescent device, there is a continuing need to develop a more stable and efficient material that can be used as an electron injecting and transporting material in the organic electroluminescent device do.

상기 문제점을 해결하고자, 본 발명은 유기 전계 발광 소자에 적용할 수 있는 신규 화합물을 제공하고자 한다. 또한 본 발명은 상기 신규 화합물을 포함하여 구동전압이 낮고, 발광효율, 열적 안정성 및 수명이 향상되는 유기 전계 발광 소자를 제공하고자 한다.In order to solve the above problems, the present invention provides a novel compound applicable to an organic electroluminescent device. Another object of the present invention is to provide an organic electroluminescent device including the novel compound, which has a low driving voltage and improved luminous efficiency, thermal stability and lifetime.

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

[화학식 1][Chemical Formula 1]

Figure pat00001
Figure pat00001

상기 화학식 1에서,In Formula 1,

X1 은 N 또는 C(R4)이고, X 1 is N or C (R 4 )

Y1 내지 Y3은 각각 독립적으로 O, S, N(Ar1) 및 C(Ar2)(Ar3)로 이루어진 군으로부터 선택되고, (단, X1 이 C(R4)이고, Y1 내지 Y3 이 모두 C(Ar2)(Ar3)인 경우 제외)Y 1 to Y 3 are each independently O, S, N (Ar 1) and C (Ar 2) is selected from the group consisting of (Ar 3), (single, and the X 1 C (R 4), Y 1 To Y 3 are both C (Ar 2 ) (Ar 3 )

R1 내지 R4는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 알킬포스핀기, C1~C60의 알킬포스피닐기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스피닐기 및 C1~C60의 아민기로 이루어진 군으로부터 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있고,R 1 to R 4 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkyl silyl group, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, an aryl boronic of C 6 ~ C 60, C 1 ~ alkylphosphonate of C 60 pingi, C 1 ~ C 60 from the alkylphosphonate blood group, C 6 ~ C 60 aryl phosphine pingi, aryl phosphine blood group and the group consisting of C 1 ~ C 60 amine groups of C 6 ~ C 60 of Selected or may combine with adjacent groups to form a condensed ring,

Ar1 내지 Ar3는 서로 동일하거나 상이하며, 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되고,Ar 1 to Ar 3 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group , A C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group is selected from aryl phosphonic blood group and C 6 ~ C 60 aryl group consisting of an amine group of a C 6 ~ C 60,

상기 Ar1 내지 Ar3 및 R1 내지 R4의 알킬기, 알케닐기, 알키닐기. 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 알킬포스핀기, 아릴포스핀기, 알킬포스피닐기, 아릴포스피닐기 및 아민기는 각각 독립적으로, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 알킬포스핀기, C1~C60의 알킬포스피닐기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스피닐기 및 C1~C60의 아민기로 이루어진 군으로부터 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있다. Ar1 내지 Ar3및 R1 내지 R4가 복수개의 치환기로 치환될 경우, 복수개의 치환기는 서로 동일하거나 상이할 수 있다.An alkyl group, an alkenyl group or an alkynyl group of the above Ar 1 to Ar 3 and R 1 to R 4 . An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, , The arylphosphinyl group and the amine group are each independently selected from the group consisting of halogen, cyano group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cyclo An alkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryl An aryloxy group of C 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkylboron group of C 1 to C 40 , an arylboron group of C 6 to C 60 , a C 1 to C 60 alkyl phosphine group, at least one member selected from the C 1 ~ C 60 alkyl phosphonic blood group, C 6 ~ C 60 aryl phosphine group, an aryl Phosphinicosuccinic group and a C 1 ~ the group consisting of C 60 amines of C 6 ~ C 60 of substitution As may be unsubstituted or substituted. When Ar 1 to Ar 3 and R 1 to R 4 are substituted with a plurality of substituents, a plurality of substituents may be the same as or different from each other.

본 발명의 바람직한 구체예에서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-A 내지 화학식 1-G로 나타내어지는 화합물들로 이루어진 군으로부터 선택되는 화합물일 수 있다:In a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound selected from the group consisting of compounds represented by the following Formulas 1-A to 1-G:

Figure pat00002
Figure pat00002

본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention relates to an organic electroluminescent device comprising a cathode, a cathode, and at least one organic layer sandwiched between the anode and the cathode, wherein at least one of the one or more organic layers includes a compound represented by the general formula An organic electroluminescent device is provided.

본 발명에서 알킬은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, alkyl means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl.

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

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

본 발명에서 아릴은 단독 고리 또는 2 이상의 고리가 조합된 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, aryl means a monovalent substituent derived from a C6-C60 aromatic hydrocarbon having a single ring or a combination of two or more rings. Also, a form in which two or more rings are pendant or condensed with each other may be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

본 발명에서 헤테로아릴은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된 형태도 포함될 수 있고, 나아가 아릴기와의 축합된 형태도 포함될 수 있다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리, 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heteroaryl means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. Wherein at least one of the carbons, preferably one to three carbons, is replaced by a heteroatom such as N, O, S or Se. 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, triazinyl, phenoxathienyl, indolizinyl, indolyl indolyl), purinyl, quinolyl, benzothiazole, carbazolyl, and heterocyclic rings such as 2-furanyl, N-imidazolyl, 2- , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

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

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

본 발명에서 아민은 R1R2N-로 표시되는 1가의 치환기로, 상기 R1 및 R2는 각각 독립적으로 탄소수 1 내지 60개의 알킬, 탄소수 6 내지 60개의 아릴 또는 핵 원자수 5 내지 60개의 헤테로아릴을 의미한다.In the present invention, the amine is a monovalent substituent represented by R 1 R 2 N-, wherein R 1 and R 2 are each independently an alkyl having 1 to 60 carbon atoms, an aryl having 6 to 60 carbon atoms, Heteroaryl " means < / RTI >

본 발명에서 시클로알킬은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 노르보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, cycloalkyl means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

본 발명에서 헤테로시클로알킬은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있으나, 이에 한정되지는 않는다.In the present invention, heterocycloalkyl means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons having from 3 to 40 nuclear atoms, wherein at least one carbon atom, preferably 1 to 3 carbon atoms, of the ring is N, O, S or Se Lt; / RTI > Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

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

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

본 발명에 따른 화학식 1로 표시되는 화합물은 전자 수송 및 주입 능력이 향상되어 전자 수송층에 사용할 경우 종래 Alq3을 사용하는 경우보다 구동 전압 및 효율 면에서 향상된 성능을 나타낸다. 인광 발광층에 사용할 경우 발광 효율 및 수명 측면에서 향상된 성능을 나타낸다. 또한 정공 주입층에 사용할 경우 구동전압 및 효율 측면에서 향상된 성능을 나타낸다. The compound represented by Formula 1 according to the present invention exhibits improved driving voltage and efficiency in the case of using the Alq3 in the electron transport layer because of its improved electron transporting and injecting ability. When used in a phosphorescent light-emitting layer, exhibits improved performance in terms of luminous efficiency and lifetime. In addition, when used in the hole injection layer, it exhibits improved performance in terms of driving voltage and efficiency.

따라서, 본 발명에 따른 화학식 1로 표시되는 화합물은 유기 발광 소자의 성능 개선 및 수명 향상에 크게 기여할 수 있으며, 특히 이러한 전자 수송 성능 향상은 풀 칼라 유기 발광 패널에서의 성능 극대화에도 큰 효과가 있다.Therefore, the compound represented by the general formula (1) according to the present invention can greatly contribute to the improvement of the performance and the lifetime of the organic light emitting device, and in particular, the improvement of the electron transport performance has a great effect in maximizing the performance in the full color organic light emitting panel.

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

1. 신규 유기 화합물1. New organic compounds

본 발명은 종래 유기 EL 소자용 재료 [예: 4,4-디카바졸일비페닐 (이하 CBP로 표시함)] 보다 높은 분자량을 가지면서, 우수한 구동 전압 특성과 효율을 갖는 신규한 축합이미다졸계 화합물을 제공한다.The present invention relates to a novel condensed imidazole-based compound having a higher molecular weight than a conventional organic EL device material (for example, 4,4-dicarbazolylbiphenyl (hereinafter referred to as CBP) .

본 발명의 화합물은 벤젠을 중심으로 3개의 5원 헤테로환(이미다졸, 옥사졸, 싸이아졸, 피롤, 싸이오펜, 퓨란)이 축합을 형성하고 있는 것을 기본 구조로 하여 삼중항에너지가 높고 좋은 인광 발광 효율 특성을 가질 수 있다. 또한 기존 호스트 재료[예: CBP] 에 비해 높은 분자량을 가져 상대적으로 열안정성이 강하다. 이로 인해 재료의 수명특성이 뛰어나 소자의 구동 수명이 매우 우수할 뿐 아니라 전력 효율의 상승을 유도하여 소비전력이 개선된 OLED 소자를 제조할 수 있다.The compound of the present invention has a structure in which three 5-membered heterocyclic rings (imidazole, oxazole, thiazole, pyrrole, thiophene, furan) form a condensation around benzene as a basic structure, And can have a luminous efficiency characteristic. It also has a higher molecular weight than conventional host materials (eg CBP) and is relatively thermally stable. This makes it possible to manufacture an OLED device having improved lifetime characteristics of the material, an excellent driving lifetime of the device, and an improved power efficiency by improving the power consumption.

또한 본 발명의 화합물은 도입되는 작용기에 따라 다양한 에너지 밴드갭 및 화학적 특성을 가질 수 있다. The compounds of the present invention may have various energy bandgaps and chemical characteristics depending on the functional groups to be introduced.

특히 R1, R2, R3, R4 위치에 방향족 고리 및 헤테로 방향족 고리가 각각 독립적으로 치환되었을 때는 평면구조를 개선하여 열적 안정도를 높일 뿐만 아니라 전자 이동성을 좋게하여 전자 수송층재료로 적합하다. 함질소 헤테로환(피리딘, 피리미딘, 피라진, 트리아진, 이미다졸, 피롤, 퀴놀린, 퀴나졸린 등), 포스피닐기 등의 우수한 전자 수송성을 갖는 작용기가 도입될 경우 본 발명의 화합물은 전체적으로 우수한 전자 수송성을 가지므로 전자수송층, 정공장벽층 등으로 사용될 수 있다.Particularly when the aromatic ring and the heteroaromatic ring are independently substituted at the R 1 , R 2 , R 3 and R 4 positions, the planar structure is improved to improve the thermal stability as well as to improve the electron mobility and to be suitable as the electron transport layer material. When a functional group having an excellent electron transporting property such as a nitrogen-containing heterocycle (pyridine, pyrimidine, pyrazine, triazine, imidazole, pyrrole, quinoline, quinazoline etc.) or a phosphinyl group is introduced, It can be used as an electron transport layer, a hole barrier layer, and the like.

한편 본 발명의 상기 화학식 1에 시아노작용기 또는 할로겐이 치환된 방향족 고리가 각각 독립적으로 치환되었을때는 LUMO 에너지가 매우 낮아져 정공주입 및 이동을 매우 좋게하므로 정공 주입층재료로 적합하다.Meanwhile, when the cyano-working vessel or the halogen-substituted aromatic ring is independently substituted with the formula 1 of the present invention, the LUMO energy is very low and the hole injection and migration are very good, which is suitable as the material of the hole injection layer.

또한 본 발명의 상기 화학식 1에 각각 독립적으로 직쇄 또는 측쇄를 가지는 지방족 탄화수소를 치환하였을때는 화합물의 용해도가 높아져서 용액 공정이 가능하다. 이 경우 재료의 용매화로 인한 잉크제조에 유리한 장점이 있다.When the aliphatic hydrocarbon having the straight chain or the branched chain is independently substituted with the above-mentioned formula (1), the solubility of the compound increases and the solution process is possible. In this case, there is an advantage in producing ink due to solubilization of the material.

본 발명의 바람직한 구체예에서, 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-A 내지 화학식 1-G로 나타내어지는 화합물들로 이루어진 군으로부터 선택되는 화합물일 수 있다:In a preferred embodiment of the present invention, the compound represented by Formula 1 may be a compound selected from the group consisting of compounds represented by the following Formulas 1-A to 1-G:

Figure pat00003
Figure pat00003

또한, 본 발명의 바람직한 한 구체예에 따르면, 상기 화학식 1로 표시되는 화합물에서 R1 내지 R4는 각각 독립적으로 할로겐, 시아노기, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C60의 알킬포스핀기, C1~C60의 알킬포스피닐기, C6~C60의 아릴포스핀기, 및 C6~C60의 아릴포스피닐기로 이루어진 군으로부터 선택될 수 있다. According to a preferred embodiment of the present invention, R 1 to R 4 in the compound represented by Formula 1 are each independently selected from the group consisting of halogen, cyano, C 1 to C 40 alkyl, C 6 to C 60 aryl , the nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 60 alkyl phosphine group, C 1 ~ C 60 alkyl phosphonic blood group, C 6 ~ C 60 aryl phosphine group, and a C 6 ~ C 60 An arylsulfonyl group, an arylsulfonyl group, and an arylphosphinyl group.

또한, 본 발명의 바람직한 한 구체예에 따르면, 상기 화학식 1로 표시되는 화합물에서 Ar1 내지 Ar3는 각각 독립적으로 할로겐, 시아노기, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기, C1~C60의 알킬포스핀기, C1~C60의 알킬포스피닐기, C6~C60의 아릴포스핀기, 및 C6~C60의 아릴포스피닐기로 이루어진 군으로부터 선택될 수 있다.According to a preferred embodiment of the present invention, in the compound represented by Formula 1, Ar 1 to Ar 3 each independently represent a halogen, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group , the nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ C 60 alkyl phosphine group, C 1 ~ C 60 alkyl phosphonic blood group, C 6 ~ C 60 aryl phosphine group, and a C 6 ~ C 60 An arylsulfonyl group, an arylsulfonyl group, and an arylphosphinyl group.

또한, 본 발명의 바람직한 한 구체예에 따르면, 상기 화학식 1로 표시되는 화합물에서 Ar1 내지 Ar3가 각각 독립적으로 C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기인 경우, 상기 아릴기 및 헤테로아릴기는 각각 독립적으로 할로겐, 시아노기 및 C6~C60의 아릴포스핀기로 이루어진 군으로부터 선택된 하나 이상의 치환기로 추가로 치환될 수 있다.According to a preferred embodiment of the present invention, when Ar 1 to Ar 3 in the compound represented by the general formula (1) are each independently a C 6 to C 60 aryl group and a heteroaryl group having 5 to 60 nuclear atoms, The aryl group and the heteroaryl group may each be independently substituted with at least one substituent selected from the group consisting of a halogen, a cyano group, and an arylphosphine group of C 6 to C 60 .

이러한 본 발명의 화학식 1로 표시되는 화합물은 하기 예시된 화학식들로 보다 구체화될 수 있다. 그러나 본 발명의 화학식 1로 표시되는 화합물이 하기 예시된 화합물들로 한정되는 것은 아니다.The compound represented by the formula (1) of the present invention can be further specified by the following formulas. However, the compound represented by formula (1) of the present invention is not limited to the following exemplified compounds.

Figure pat00004
Figure pat00005
Figure pat00004
Figure pat00005

Figure pat00006
Figure pat00006

Figure pat00007
Figure pat00007

Figure pat00008
Figure pat00008

Figure pat00009
Figure pat00009

Figure pat00010
Figure pat00010

Figure pat00011

Figure pat00011

2. 유기 전계 발광 소자2. Organic electroluminescent device

본 발명은 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 1종 이상 포함하는 유기 전계 발광 소자를 제공한다.The present invention relates to 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 at least one compound represented by Formula 1 to provide.

상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있다. 바람직하게는 상기 화학식 1 로 표시되는 화합물은 전자 수송층 또는 정공 주입층 물질로서 유기 전계 발광 소자에 포함될 수 있다. 이 경우 유기 전계 발광 소자는 발광효율, 전력효율, 열적 안정성 및 소자 수명이 향상될 수 있다.The organic material layer containing the compound represented by Formula 1 may be at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. Preferably, the compound represented by Formula 1 may be included in an organic electroluminescent device as an electron transport layer or a hole injection layer material. In this case, the light emitting efficiency, power efficiency, thermal stability and lifetime of the organic electroluminescent device can be improved.

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

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

본 발명의 유기 전계 발광 소자에서 상기 화학식 1 로 표시되는 화합물을 포함하는 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 한정되지는 않는다.In the organic electroluminescent device of the present invention, the organic material layer containing the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, and thermal transfer.

본 발명의 유기 전계 발광 소자는 유기물층 중 1층 이상을 상기 화학식 1 로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다.The organic electroluminescent device of the present invention is manufactured by forming an organic layer and an electrode using materials and methods known in the art, except that one or more layers of the organic layers are formed so as to include the compound represented by Formula 1 .

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

양극 물질로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에 한정되는 것은 아니다.Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but are not limited thereto.

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

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

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

[준비예 1][Preparation Example 1]

a-1의 합성Synthesis of a-1

2,4,6-트리나이트로-N1,N3,N5-트리페닐벤젠-1,3,5-트리아민의 합성Synthesis of 2,4,6-trinitro-N1, N3, N5-triphenylbenzene-1,3,5-triamine

Figure pat00012
Figure pat00012

질소 기류 하에서 1,3,5-트리클로로-2,4,6-트리나이트로벤젠 (10.0 g, 31.6 mmol)을 200 ml의 ACN에 녹인 후 아닐린 (8.63ml, 94.8mmol)을 천천히 적가하였다. 상온에서 4시간 동안 교반 후 반응이 종결되면 생성된 고체 혼합물을 여과하고 ACN으로 세척하였다. 얻어진 고체화합물을 45℃ 훈풍건조하에서 24시간 건조하여 목적 화합물을 13.8g(90%)얻었다.1,3,5-trichloro-2,4,6-trinitrobenzene (10.0 g, 31.6 mmol) was dissolved in 200 ml of ACN under a nitrogen stream, and then aniline (8.63 ml, 94.8 mmol) was slowly added dropwise. After the reaction was completed at room temperature for 4 hours, the resulting solid mixture was filtered and washed with ACN. The obtained solid compound was dried under a warm air drying condition at 45 ° C for 24 hours to obtain 13.8 g (90%) of the target compound.

GC-Mass (이론치: 486.13 g/mol, 측정치: 486 g/mol)GC-Mass (calculated: 486.13 g / mol, measured: 486 g / mol)

1H-NMR: 10.1 (s, 3H), 7.69 (s, 6H), 7.66(s, 3H), 7.57(s,6H)
 1 H-NMR: 10.1 (s , 3H), 7.69 (s, 6H), 7.66 (s, 3H), 7.57 (s, 6H)

[준비예 2][Preparation Example 2]

a-2의 합성Synthesis of a-2

N1,N3,N5-트리페닐벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-triphenylbenzene-1,2,3,4,5,6-hexaamine

Figure pat00013

Figure pat00013

반응 용기에 Fe 파우더 (1.58g, 140mmol), EtOH 200ml, 및 H2O 50ml을 넣고 교반하였다. HCl (35%, 2ml, 2.8mmol)을 천천히 적가하고 2시간 동안 가열하여 환류시켰다. 2시간이 지난 후 준비예 1에서 합성한 a1 (13.8g 28mmol)을 넣고 2시간 동안 가열하여 환류시켰다. 반응 종결 후 메틸렌클로라이드로 추출하고 감압조건에서 용매를 농축하였다. 생성된 혼합물을 MeOH으로 결정화하여 여과하고 MeOH으로 세척하였다. 얻어진 고체화합물을 45℃ 훈풍건조하에서 24시간 건조하여 목적 화합물을 6.88g(62%)얻었다.To the reaction vessel, Fe powder (1.58 g, 140 mmol), 200 ml of EtOH, and 50 ml of H 2 O were added and stirred. HCl (35%, 2ml, 2.8mmol) was slowly added dropwise and refluxed by heating for 2 hours. After 2 hours, a1 (13.8 g, 28 mmol) synthesized in Preparation Example 1 was added and heated for 2 hours to reflux. After completion of the reaction, the reaction mixture was extracted with methylene chloride, and the solvent was concentrated under reduced pressure. The resulting mixture was crystallized with MeOH, filtered and washed with MeOH. The obtained solid compound was dried under a warm air drying condition at 45 ° C for 24 hours to obtain 6.88 g (62%) of the target compound.

GC-Mass (이론치: 396.21 g/mol, 측정치: 396 g/mol)GC-Mass (calculated: 396.21 g / mol, measured: 396 g / mol)

1H-NMR: δ 7.18 (m, 6H), 6.76 (m, 3H), 7.61 (m, 6H), 4.79 (s, 3H)
 1 H-NMR: δ 7.18 ( m, 6H), 6.76 (m, 3H), 7.61 (m, 6H), 4.79 (s, 3H)

[준비예 3][Preparation Example 3]

a-3의 합성Synthesis of a-3

2,4,6-트리나이트로-N1,N3,N5-트리(피리딘-3-일)벤젠-1,3,5-트리아민의 합성Synthesis of 2,4,6-trinitro-N1, N3, N5-tri (pyridin-3-yl) benzene-1,3,5-triamine

Figure pat00014
Figure pat00014

반응물로 피리딘-3-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 11.4g (수율 72%)을 얻었다: GC-Mass (이론치: 489.40 g/mol, 측정치: 489 g/mol)
(Yield: 72%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that pyridine-3-amine was used as the reactant. GC-Mass (theoretical value: 489.40 g / mol, measurement value: 489 g / mol)

[준비예 4][Preparation Example 4]

a-4의 합성Synthesis of a-4

N1,N3,N5-트리(피리딘-3-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tri (pyridin-3-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00015
Figure pat00015

반응물로 2,4,6-트리나이트로-N1,N3,N5-트리(피리딘-3-일)벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 6.4g(수율 70%)을 얻었다: GC-Mass (이론치: 399.45 g/mol, 측정치: 399 g/mol)
The same procedure as in [Preparation Example 2] was carried out except that 2,4,6-trinitro-N1, N3, N5-tri (pyridin-3-yl) benzene-1,3,5- (Yield: 70%): GC-Mass (399.45 g / mol, measured: 399 g / mol)

[준비예 5][Preparation Example 5]

a-5의 합성Synthesis of a-5

N1,N3,N5-트리([1,1'-비페닐]-4-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-trie ([1,1'-biphenyl] -4-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00016
Figure pat00016

반응물로 [1,1'-비페닐]-4-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 18g (수율 80%)을 얻었다: GC-Mass (이론치: 714.22 g/mol, 측정치: 714 g/mol)
18 g (yield 80%) of the title compound was obtained by carrying out the same procedure as in [Preparation Example 1], except that [l, l'-biphenyl] -4- amine was used as the reactant: GC-Mass (theoretical value: 714.22 g / mol, measured: 714 g / mol)

[준비예 6][Preparation Example 6]

a-6의 합성Synthesis of a-6

N1,N3,N5-트리([1,1'-비페닐]-4-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-trie ([1,1'-biphenyl] -4-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00017
Figure pat00017

반응물로 N1,N3,N5-트리([1,1'-비페닐]-4-일)벤젠-1,2,3,4,5,6-헥사아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 10.6g(수율 68%)을 얻었다: GC-Mass (이론치: 624.30 g/mol, 측정치: 624 g/mol)
Except that N1, N3, N5-trie ([1,1'-biphenyl] -4-yl) benzene-1,2,3,4,5,6-hexaamine was used as a reactant in Preparation Example 2 (GC-Mass: 624.30 g / mol, measured: 624 g / mol) was obtained in the same manner as in Example 1,

[준비예 7][Preparation Example 7]

a-7의 합성Synthesis of a-7

N1,N3,N5-트리(나프탈렌-2-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-tri (naphthalen-2-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00018
Figure pat00018

반응물로 나프탈렌-2-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 18.5g (수율 92%)을 얻었다: GC-Mass (이론치: 636.61 g/mol, 측정치: 637 g/mol)
(Yield: 92%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that naphthalene-2-amine was used as the reactant. GC-Mass (theoretical value: 636.61 g / mol, g / mol)

[준비예 8][Preparation Example 8]

a-8의 합성Synthesis of a-8

N1,N3,N5-트리(나프탈렌-2-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tri (naphthalen-2-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00019
Figure pat00019

반응물로 N1,N3,N5-트리(나프탈렌-2-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 8.7g(수율 55%)을 얻었다: GC-Mass (이론치: 546.25 g/mol, 측정치: 546 g/mol)
Except that N1, N3, N5-tri (naphthalene-2-yl) -2,4,6-trinitrobenzene-1,3,5-triamine was used as a reactant in the same manner as in [Preparation Example 2] (Yield: 55%): GC-Mass (calculated: 546.25 g / mol, measured: 546 g / mol)

[준비예 9][Preparation Example 9]

a-9의 합성Synthesis of a-9

2,4,6-트리나이트로-N1,N3,N5-트리스(9-페닐-9H-카바졸-3-일)벤젠-1,3,5-트리아민의 합성Synthesis of 2,4,6-trinitro-N1, N3, N5-tris (9-phenyl-9H-carbazol-3-yl) benzene-1,3,5-triamine

Figure pat00020
Figure pat00020

반응물로 9-페닐-9H-카바졸-3-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 29.48g (수율 95%)을 얻었다: GC-Mass (이론치: 982.30 g/mol, 측정치: 982 g/mol)
(Yield: 95%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that 9-phenyl-9H-carbazol-3-amine was used as the reactant. GC- g / mol, measured: 982 g / mol)

[준비예 10][Preparation Example 10]

a-10의 합성Synthesis of a-10

N1,N3,N5-트리스(9-페닐-9H-카바졸-3-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (9-phenyl-9H-carbazol-3-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00021
Figure pat00021

반응물로 2,4,6-트리나이트로-N1,N3,N5-트리스(9-페닐-9H-카바졸-3-일)벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 12.8g(수율 48%)을 얻었다: GC-Mass (이론치: 891.38 g/mol, 측정치: 891 g/mol)
Except that 2,4,6-trinitro-N1, N3 and N5-tris (9-phenyl-9H-carbazol-3-yl) benzene-1,3,5-triamine were used as reactants. Mass (891.38 g / mol, measured: 891 g / mol) was obtained in the same manner as in Preparation Example 2,

[준비예 11][Preparation Example 11]

a-11의 합성Synthesis of a-11

N1,N3,N5-트리스(디벤조[b,d]티오펜-2-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-tris (dibenzo [b, d] thiophen-2-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00022
Figure pat00022

반응물로 디벤조[b,d]티오펜-2-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 22.3g (수율 88%)을 얻었다: GC-Mass (이론치: 804.09 g/mol, 측정치: 804 g/mol)
(Yield: 88%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that dibenzo [b, d] thiophen- 804.09 g / mol, measurement: 804 g / mol)

[준비예 12][Preparation Example 12]

a-12의 합성Synthesis of a-12

N1,N3,N5-트리스(디벤조[b,d]티오펜-2-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (dibenzo [b, d] thiophen-2-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00023
Figure pat00023

반응물로 2N1,N3,N5-트리스(디벤조[b,d]티오펜-2-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 9.9g(수율 50%)을 얻었다: GC-Mass (이론치: 714.17 g/mol, 측정치: 714 g/mol)
Except that 2N1, N3, N5-tris (dibenzo [b, d] thiophen-2-yl) -2,4,6-trinitrobenzene-1,3,5-triamine was used as a reactant (Theoretical value: 714.17 g / mol, measured value: 714 g / mol) was obtained by carrying out the same procedure as in [Preparation Example 2]

[준비예 13][Preparation Example 13]

a-13의 합성Synthesis of a-13

2,4,6-트리나이트로-N1,N3,N5-트리스(3-(피리딘-3-일)페닐)벤젠-1,3,5-트리아민의 합성Synthesis of 2,4,6-trinitro-N1, N3, N5-tris (3- (pyridin-3-yl) phenyl) benzene-1,3,5-triamine

Figure pat00024
Figure pat00024

반응물로 3-(피리딘-3-일)아닐린을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 20.1g (수율 89%)을 얻었다: GC-Mass (이론치: 717.21 g/mol, 측정치: 717 g/mol)
(Yield: 89%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that 3- (pyridin-3-yl) aniline was used as the reactant. GC-Mass (717.21 g / mol, measured: 717 g / mol)

[준비예 14][Preparation Example 14]

a-14의 합성Synthesis of a-14

N1,N3,N5-트리([1,1'-비페닐]-3-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-trie ([1,1'-biphenyl] -3-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00025
Figure pat00025

반응물로 2,4,6-트리나이트로-N1,N3,N5-트리스(3-(피리딘-3-일)페닐)벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 10.4g(수율 60%)을 얻었다: GC-Mass (이론치: 624.78 g/mol, 측정치: 625 g/mol)
Except that 2,4,6-trinitro-N1, N3 and N5-tris (3- (pyridin-3-yl) phenyl) benzene-1,3,5-triamine were used as reactants (Theoretical value: 624.78 g / mol, measured value: 625 g / mol) was obtained in the same manner as in [

[준비예 15][Preparation Example 15]

a-15 합성a-15 synthesis

N1,N3,N5-트리([1,1'-비페닐]-3-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-trie ([1,1'-biphenyl] -3-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00026
Figure pat00026

반응물로 [1,1'-비페닐]-3-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 20.5 (수율 91%)을 얻었다: GC-Mass (이론치: 714.72g/mol, 측정치: 715g/mol)
(Yield: 91%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that [l, r-biphenyl] g / mol, measured: 715 g / mol)

[준비예 16][Preparation Example 16]

a-16 합성a-16 synthesis

N1,N3,N5-트리([1,1'-비페닐]-3-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-trie ([1,1'-biphenyl] -3-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00027
Figure pat00027

반응물로 2N1,N3,N5-트리([1,1'-비페닐]-3-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 11.1g(수율 62%)을 얻었다: GC-Mass (이론치: 624.78 g/mol, 측정치: 625 g/mol)
Except that 2N1, N3, N5-trie ([1,1'-biphenyl] -3-yl) -2,4,6-trinitrobenzene-1,3,5-triamine was used as a reactant (Theoretical value: 624.78 g / mol, measured value: 625 g / mol) was obtained in the same manner as in [Preparation Example 2]

[준비예 15][Preparation Example 15]

a-15 합성a-15 synthesis

N1,N3,N5-트리([1,1'-비페닐]-3-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-trie ([1,1'-biphenyl] -3-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00028
Figure pat00028

반응물로 [1,1'-비페닐]-3-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 20.5 (수율 91%)을 얻었다: GC-Mass (이론치: 714.72g/mol, 측정치: 715g/mol)
(Yield: 91%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that [l, r-biphenyl] g / mol, measured: 715 g / mol)

[준비예 16][Preparation Example 16]

a-16 합성a-16 synthesis

N1,N3,N5-트리([1,1'-비페닐]-3-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-trie ([1,1'-biphenyl] -3-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00029
Figure pat00029

반응물로 2N1,N3,N5-트리([1,1'-비페닐]-3-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 11.1g(수율 62%)을 얻었다: GC-Mass (이론치: 624.78 g/mol, 측정치: 625 g/mol)
Except that 2N1, N3, N5-trie ([1,1'-biphenyl] -3-yl) -2,4,6-trinitrobenzene-1,3,5-triamine was used as a reactant (Theoretical value: 624.78 g / mol, measured value: 625 g / mol) was obtained in the same manner as in [Preparation Example 2]

[준비예 17][Preparation Example 17]

a-17 합성a-17 synthesis

2,4,6-트리나이트로-N1,N3,N5-트리스(트리페닐렌-2-일)벤젠-1,3,5-트리아민의 합성Synthesis of 2,4,6-trinitro-N1, N3, N5-tris (triphenylene-2-yl) benzene-1,3,5-triamine

Figure pat00030
Figure pat00030

반응물로 트리페닐렌-2-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 26g (수율 88%)을 얻었다: GC-Mass (이론치: 936.27g/mol, 측정치: 936g/mol)
(Yield: 88%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that triphenylene-2-amine was used as the reactant. GC-Mass (theoretical value: 936.27 g / mol, 936 g / mol)

[준비예 18][Preparation Example 18]

a-18 합성a-18 synthesis

N1,N3,N5-트리스(트리페닐렌-2-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (triphenylene-2-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00031
Figure pat00031

반응물로 2,4,6-트리나이트로-N1,N3,N5-트리스(트리페닐렌-2-일)벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 14.1g(수율 60%)을 얻었다: GC-Mass (이론치: 846.358 g/mol, 측정치: 846 g/mol)
Preparation Example 2] was repeated except that 2,4,6-trinitro-N1, N3, N5-tris (triphenylene-2-yl) benzene-1,3,5-triamine was used as a reactant. (Theoretical value: 846.358 g / mol, measured value: 846 g / mol) was obtained in the same manner as in Example 1,

[준비예 19][Preparation Example 19]

a-19 합성a-19 synthesis

N1,N3,N5-트리스(디벤조[b,d]티오펜-4-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-tris (dibenzo [b, d] thiophen-4-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00032
Figure pat00032

반응물로 디벤조[b,d]티오펜-4-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 19.8g (수율 78%)을 얻었다: GC-Mass (이론치: 804.87g/mol, 측정치: 805g/mol)
(Yield: 78%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that dibenzo [b, d] thiophen- 804.87 g / mol, measured: 805 g / mol)

[준비예 20][Preparation Example 20]

a-20 합성a-20 synthesis

N1,N3,N5-트리스(디벤조[b,d]티오펜-4-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (dibenzo [b, d] thiophen-4-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00033
Figure pat00033

반응물로 N1,N3,N5-트리스(디벤조[b,d]티오펜-4-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 7.9g(수율 45%)을 얻었다: GC-Mass (이론치: 714.92 g/mol, 측정치: 715 g/mol)
Except that N1, N3, N5-tris (dibenzo [b, d] thiophen-4-yl) -2,4,6-trinitrobenzene-1,3,5-triamine was used as the reactant (Theoretical value: 714.92 g / mol, measured value: 715 g / mol) was obtained by carrying out the same procedures as in [Preparation Example 2]

[준비예 21][Preparation Example 21]

a-21 합성a-21 synthesis

N1,N3,N5-트리스(9-메틸-1,10-펜안트롤린2-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-tris (9-methyl-1,10-phenanthroline 2-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00034
Figure pat00034

반응물로 9-메틸-1,10-펜안트롤린2-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 19.7g (수율 75%)을 얻었다: GC-Mass (이론치: 834.24g/mol, 측정치: 834g/mol)
The procedure of Preparation Example 1 was repeated except that 9-methyl-1,10-phenanthroline 2-amine was used as the reactant, to obtain 19.7 g (yield 75%) of the target compound: GC-Mass : 834.24 g / mol, measured: 834 g / mol)

[준비예 22][Preparation Example 22]

a-22 합성a-22 synthesis

N1,N3,N5-트리스(9-메틸-1,10-펜안트롤린2-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (9-methyl-1,10-phenanthroline 2-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00035
Figure pat00035

반응물로 N1,N3,N5-트리스(9-메틸-1,10-펜안트롤린2-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 5.6g(수율 32%)을 얻었다: GC-Mass (이론치: 744.32 g/mol, 측정치: 744 g/mol)
Except that N1, N3, N5-tris (9-methyl-1,10-phenanthroline 2-yl) -2,4,6-trinitrobenzene-1,3,5-triamine was used as a reactant (Theoretical value: 744.32 g / mol, measured value: 744 g / mol) was obtained by carrying out the same procedure as in [Preparation Example 2] to obtain 5.6 g (yield 32%

[준비예 23][Preparation Example 23]

a-23 합성a-23 synthesis

(((2,4,6-트리나이트로벤젠-1,3,5-트리일)트리스(아자네디일))트리스(벤젠-4,1-디일))트리스(페닐포스피나이트)의 합성(Synthesis of ((2,4,6-trinitrobenzene-1,3,5-triyl) tris (azanediyl)) tris (benzene-4,1-diyl)) tris (phenylphosphinite)

Figure pat00036
Figure pat00036

반응물로 (4-아미노페닐)(페닐)포스피나이트를 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 17.8g (수율 66%)을 얻었다: GC-Mass (이론치: 855.13g/mol, 측정치: 855g/mol)
(Yield: 66%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that (4-aminophenyl) (phenyl) phosphinite was used as the reaction product. GC-Mass (theoretical value: 855.13 g / mol, measured: 855 g / mol)

[준비예 24][Preparation Example 24]

a-24 합성a-24 synthesis

(((2,4,6-트리아미노벤젠-1,3,5-트리일)트리스(아자네디일))트리스(벤젠-4,1-디일))트리스(페닐포스피나이트)의 합성Synthesis of tris (benzene-4,1-diyl)) tris (phenylphosphinite) (((2,4,6-triaminobenzene-1,3,5-triyl) tris

Figure pat00037
Figure pat00037

반응물로 N1(((2,4,6-트리나이트로벤젠-1,3,5-트리일)트리스(아자네디일))트리스(벤젠-4,1-디일))트리스(페닐포스피나이트)을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 6.4g(수율 40%)을 얻었다: GC-Mass (이론치: 765.70 g/mol, 측정치: 766 g/mol)
Tris (benzene-4,1-diyl)) tris ((2,4,6-trinitrobenzene-1,3,5-triyl) tris (azanediyl)) tris (phenylphosphonite (Theoretical value: 765.70 g / mol, measured value: 766 g / mol) was obtained in the same manner as in [Preparation Example 2]

[준비예 25][Preparation Example 25]

a-25 합성a-25 synthesis

2,4,6-트리나이트로-N1,N3,N5-트리스(4-(피리딘-3-일)페닐)벤젠-1,3,5-트리아민의 합성Synthesis of 2,4,6-trinitro-N1, N3, N5-tris (4- (pyridin-3-yl) phenyl) benzene-1,3,5-triamine

Figure pat00038
Figure pat00038

반응물로 4-(피리딘-3-일)아닐린을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 21.8g (수율 85%)을 얻었다: GC-Mass (이론치: 804.87g/mol, 측정치: 805g/mol)
(Yield: 85%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that 4- (pyridin-3-yl) aniline was used as the reactant. GC-Mass (theoretical value: 804.87 g / mol, measured: 805 g / mol)

[준비예 26][Preparation Example 26]

a-26 합성a-26 synthesis

N1,N3,N5-트리스(4-(피리딘-3-일)페닐)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (4- (pyridin-3-yl) phenyl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00039
Figure pat00039

반응물로 2,4,6-트리나이트로-N1,N3,N5-트리스(4-(피리딘-3-일)페닐)벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 6.97g(수율 41%)을 얻었다: GC-Mass (이론치: 627.29 g/mol, 측정치: 627 g/mol)
Except that 2,4,6-trinitro-N1, N3, N5-tris (4- (pyridin-3-yl) phenyl) benzene-1,3,5-triamine was used as the reactant (Theoretical value: 627.29 g / mol, measured value: 627 g / mol) was obtained in the same manner as in [

[준비예 27][Preparation Example 27]

a-27 합성a-27 synthesis

N,N',N''-(2,4,6-트리나이트로벤젠-1,3,5-트리일)트리시안아마이드의 합성Synthesis of N, N ', N "- (2,4,6-trinitrobenzene-1,3,5-triyl) tricyanamide

Figure pat00040
Figure pat00040

반응물로 시안아마이드를 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 8.4g (수율 80%)을 얻었다: GC-Mass (이론치: 333.02g/mol, 측정치: 333g/mol)
(Theoretical value: 333.02 g / mol, measured value: 333 g / mol) was obtained by carrying out the same procedure as in [Preparation Example 1], except that cyanamide was used as the reactant.

[준비예 28][Preparation Example 28]

a-28 합성a-28 synthesis

N,N',N''-(2,4,6-트리아미노벤젠-1,3,5-트리일)트리시안아마이드의 합성Synthesis of N, N ', N "- (2,4,6-triaminobenzene-1,3,5-triyl) tricyanamide

Figure pat00041
Figure pat00041

반응물로 N,N',N''-(2,4,6-트리나이트로벤젠-1,3,5-트리일)트리시안아마이드를 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 2.5g(수율 40%)을 얻었다: GC-Mass (이론치: 243.10 g/mol, 측정치: 243 g/mol)
The same procedure as in [Preparation Example 2] was carried out except that N, N ', N "- (2,4,6-trinitrobenzene-1,3,5-triyl) tricyanamide was used as a reactant (Yield: 40%): GC-Mass (calculated: 243.10 g / mol, measured: 243 g / mol)

[준비예 29][Preparation Example 29]

a-29 합성a-29 synthesis

N1,N3,N5-트리스(4-플루오로페닐)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-tris (4-fluorophenyl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00042
Figure pat00042

반응물로 4-플루오로아닐린을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 15.35g (수율 90%)을 얻었다: GC-Mass (이론치: 540.10g/mol, 측정치: 540g/mol)
15.35 g (yield 90%) of the title compound was obtained by carrying out the same procedure as in [Preparation Example 1] except that 4-fluoroaniline was used as the reactant. GC-Mass (theoretical value: 540.10 g / mol, / mol)

[준비예 30][Preparation Example 30]

a-30 합성a-30 synthesis

N1,N3,N5-트리스(4-플루오로페닐)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (4-fluorophenyl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00043
Figure pat00043

반응물로 N1,N3,N5-트리스(4-플루오로페닐)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 5.7g(수율 45%)을 얻었다: GC-Mass (이론치: 450.18 g/mol, 측정치: 450 g/mol)
The same procedure as in [Preparation Example 2] was performed except that N1, N3, N5-tris (4-fluorophenyl) -2,4,6-trinitrobenzene-1,3,5- (Yield: 45%): GC-Mass (450.18 g / mol, measured: 450 g / mol)

[준비예 31][Preparation Example 31]

a-31 합성a-31 synthesis

4,4',4''-((2,4,6-트리나이트로벤젠-1,3,5-트리일)트리스(아자네디일))트리프탈로니트릴의 합성Synthesis of 4,4 ', 4 "- ((2,4,6-trinitrobenzene-1,3,5-triyl) tris (azanediyl)) tripthalonitrile

Figure pat00044
Figure pat00044

반응물로 4-아미노프탈로니트릴을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 16.4g (수율 82%)을 얻었다: GC-Mass (이론치: 636.10g/mol, 측정치: 636g/mol)
(Yield: 82%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that 4-aminophthalonitrile was used as the reactant. GC-Mass (theoretical value: 636.10 g / mol, 636 g / mol)

[준비예 32][Preparation Example 32]

a-32 합성a-32 synthesis

4,4',4''-((2,4,6-트리아미노벤젠-1,3,5-트리일)트리스(아자네디일))트리프탈로니트릴의 합성Synthesis of 4,4 ', 4 "- ((2,4,6-triaminobenzene-1,3,5-triyl) tris (azanediyl)) tripalonitrile

Figure pat00045
Figure pat00045

반응물로 4,4',4''-((2,4,6-트리나이트로벤젠-1,3,5-트리일)트리스(아자네디일))트리프탈로니트릴을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 7g(수율 50%)을 얻었다: GC-Mass (이론치: 546.18 g/mol, 측정치: 546 g/mol)
Except that 4,4 ', 4 "- ((2,4,6-trinitrobenzene-1,3,5-triyl) tris (azanediyl)) triphthalonitrile was used as the reactant (Theoretical value: 546.18 g / mol, measured value: 546 g / mol) was obtained in the same manner as in [Preparation Example 2]

[준비예 33][Preparation Example 33]

a-33 합성a-33 synthesis

2,4,6-트리나이트로-N1,N3,N5-트리프로필벤젠-1,3,5-트리아민의 합성Synthesis of 2,4,6-trinitro-N1, N3, N5-tripropylbenzene-1,3,5-triamine

Figure pat00046
Figure pat00046

반응물로 프로판-1-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 9.79g (수율 80%)을 얻었다: GC-Mass (이론치: 384.18g/mol, 측정치: 384g/mol)
(Yield: 80%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that propane-1-amine was used as the reactant. GC-Mass (calculated value: 384.18 g / mol, measured value: 384 g / mol)

[준비예 34][Preparation Example 34]

a-34 합성a-34 synthesis

N1,N3,N5-트리프로필벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tripropylbenzene-1,2,3,4,5,6-hexaamine

Figure pat00047
Figure pat00047

반응물로 2,4,6-트리나이트로-N1,N3,N5-트리프로필벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 3.7g(수율 40%)을 얻었다: GC-Mass (이론치: 294.25 g/mol, 측정치: 294 g/mol)
The procedure of Preparation Example 2 was repeated except that 2,4,6-trinitro-N1, N3, N5-tripropylbenzene-1,3,5-triamine was used as a reactant to obtain the desired compound 3.7 (yield: 40%): GC-Mass (294.25 g / mol, measured: 294 g / mol)

[준비예 35][Preparation Example 35]

a-35 합성a-35 synthesis

N1,N3,N5-트리이소부틸-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-triisobutyl-2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00048
Figure pat00048

반응물로 2-메틸프로판-1-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 11.6g (수율 86%)을 얻었다: GC-Mass (이론치: 426.22g/mol, 측정치: 426g/mol)
(Yield: 86%) was obtained by carrying out the same procedure as in [Preparation Example 1], except that 2-methylpropane-1-amine was used as the reactant. GC-Mass (theoretical value: 426.22 g / mol, Measured: 426 g / mol)

[준비예 36][Preparation Example 36]

a-36 합성a-36 synthesis

N1,N3,N5-트리이소부틸벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-triisobutylbenzene-1,2,3,4,5,6-hexaamine

Figure pat00049
Figure pat00049

반응물로 N1,N3,N5-트리이소부틸-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 4.7g(수율 51%)을 얻었다: GC-Mass (이론치: 336.30 g/mol, 측정치: 336 g/mol)
The procedure of Preparation Example 2 was repeated except that N1, N3, N5-triisobutyl-2,4,6-trinitrobenzene-1,3,5-triamine was used as a reactant, (Yield: 51%): GC-Mass (336.30 g / mol, measured: 336 g / mol)

[준비예 37][Preparation Example 37]

a-37 합성a-37 synthesis

N1,N3,N5-트리스(9,9-디메틸-9H-플루오렌-3-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-tris (9,9-dimethyl-9H-fluoren-3-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00050
Figure pat00050

반응물로 9,9-디메틸-9H-플루오렌-3-아민을 사용한 것을 제외하고는 [준비예 1]과 동일한 과정을 수행하여 목적 화합물 22.8g (수율 86%)을 얻었다: GC-Mass (이론치: 834.32 g/mol, 측정치: 834g/mol)
(Yield: 86%) was obtained by carrying out the same procedure as in [Preparation Example 1] except that 9,9-dimethyl-9H-fluorene-3-amine was used as the reactant: GC-Mass : 834.32 g / mol, measured: 834 g / mol)

[준비예 38][Preparation Example 38]

a-38 합성a-38 synthesis

N1,N3,N5-트리스(9,9-디메틸-9H-플루오렌-3-일)벤젠-1,2,3,4,5,6-헥사아민의 합성Synthesis of N1, N3, N5-tris (9,9-dimethyl-9H-fluoren-3-yl) benzene-1,2,3,4,5,6-hexaamine

Figure pat00051
Figure pat00051

반응물로 N1,N3,N5-트리스(9,9-디메틸-9H-플루오렌-3-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민을 사용한 것을 제외하고는 [준비예 2]와 동일한 과정을 수행하여 목적 화합물 11.2g(수율 55%)을 얻었다: GC-Mass (이론치: 744.39 g/mol, 측정치: 744 g/mol)
Except that N1, N3, N5-tris (9,9-dimethyl-9H-fluoren-3-yl) -2,4,6-trinitrobenzene-1,3,5-triamine was used as a reactant (Theoretical value: 744.39 g / mol, measured value: 744 g / mol) was obtained in the same manner as in [Preparation Example 2]

[준비예 39][Preparation Example 39]

a-39의 합성Synthesis of a-39

((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리벤젠의 합성((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-2,1-diyl)) tribenzene Synthesis of

Figure pat00052
Figure pat00052

질소 기류 하에서 1,3,5-트리플루오로-2,4,6-트리아이오도벤젠 (10.0 g, 19.6 mmol), 에티닐벤젠(6g, 58.8mmol), 디이소프로필아민(1.98g, 58.8mmol), CuI(2.2g, 11.76mmol), PdCl2(PPh3)2(1.37g, 1.96mmol)을 200 ml의 톨루엔에 녹인 후 20시간 동안 환류 교반시켰다. 반응 종결 후 메틸렌클로라이드로 추출하고 감압조건에서 농축한 후 컬럼크로마토그래피를 이용하여 목적 화합물을 7g(83%) 얻었다.(10.0 g, 19.6 mmol), ethynylbenzene (6 g, 58.8 mmol) and diisopropylamine (1.98 g, 58.8 mmol) in a nitrogen stream. mmol), CuI (2.2 g, 11.76 mmol) and PdCl 2 (PPh 3) 2 (1.37 g, 1.96 mmol) were dissolved in 200 ml of toluene and refluxed with stirring for 20 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and then subjected to column chromatography to obtain 7 g (83%) of the target compound.

GC-Mass (이론치: 432.11 g/mol, 측정치: 432 g/mol)GC-Mass (calculated: 432.11 g / mol, measured: 432 g / mol)

1H-NMR: 7.62 (m, 6H), 7.69 (m, 9H)
 1 H-NMR: 7.62 (m , 6H), 7.69 (m, 9H)

[준비예 40][Preparation Example 40]

a-40 합성a-40 synthesis

N1,N3,N5-트리스(9,9-디메틸-9H-플루오렌-3-일)-2,4,6-트리나이트로벤젠-1,3,5-트리아민의 합성Synthesis of N1, N3, N5-tris (9,9-dimethyl-9H-fluoren-3-yl) -2,4,6-trinitrobenzene-1,3,5-triamine

Figure pat00053
Figure pat00053

반응물로 4-에티닐-1,1'-비페닐을 사용한 것을 제외하고는 [준비예 39]과 동일한 과정을 수행하여 목적 화합물 22.8g (수율 86%)을 얻었다: GC-Mass (이론치: 600.21 g/mol, 측정치: 600g/mol)
(Yield: 86%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 4-ethynyl-1,1'-biphenyl was used as the reactant. GC- g / mol, measurement: 600 g / mol)

[준비예 41][Preparation Example 41]

a-41 합성a-41 synthesis

3,3'',3''''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리-1,1'-비페닐의 합성3, 3 '', 3 '' '- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne- '- Synthesis of biphenyls

Figure pat00054
Figure pat00054

반응물로 3-에티닐-1,1'-비페닐을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 11.0g(수율 94%)을 얻었다: GC-Mass (이론치: 600.21 g/mol, 측정치: 600 g/mol)
(Yield: 94%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 3-ethynyl-1,1'-biphenyl was used as the reactant. GC- g / mol, measurement: 600 g / mol)

[준비예 42][Preparation Example 42]

a-42 합성a-42 synthesis

2,2',2''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리나프탈렌의 합성Synthesis of 2,2 ', 2 "- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-1,1-diyl)) trinaphthalene

Figure pat00055
Figure pat00055

반응물로 2-에티닐나프탈렌을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 10.0g(수율 88%)을 얻었다: GC-Mass (이론치: 582.16 g/mol, 측정치: 582 g/mol)
(Yield: 88%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 2-ethynylnaphthalene was used as the reactant. GC-Mass (theoretical value: 582.16 g / mol, measurement value: 582 g / mol)

[준비예 43][Preparation Example 43]

a-43 합성a-43 synthesis

6,6',6''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리퀴놀린의 합성Synthesis of 6,6 ', 6' '- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-1,1-diyl)) triquinoline

Figure pat00056
Figure pat00056

반응물로 7-에티닐퀴놀린을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 8.8g(수율 77%)을 얻었다: GC-Mass (이론치: 585.15 g/mol, 측정치: 585 g/mol)
(Yield: 77%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 7-ethynylquinoline was used as the reactant. GC-Mass (calculated value: 585.15 g / mol, measured: 585 g / mol)

[준비예 44][Preparation Example 44]

a-44 합성a-44 synthesis

9,9',9''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리펜안트렌의 합성Synthesis of 9,9 ', 9' '- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-1,1-diyl)) triphenanthrene

Figure pat00057
Figure pat00057

반응물로 9-에티닐펜안트렌을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 11.9g(수율 83%)을 얻었다: GC-Mass (이론치: 732.21 g/mol, 측정치: 732 g/mol)
(Yield: 83%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 9-ethynylphenanthrene was used as the reactant. GC-Mass (theoretical value: 732.21 g / mol, 732 g / mol)

[준비예 45][Preparation Example 45]

a-45 합성a-45 synthesis

1,1',1''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리나프탈렌의 합성Synthesis of 1,1 ', 1 "- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-1,1-diyl)) trinaphthalene

Figure pat00058
Figure pat00058

반응물로 1-에티닐나프탈렌을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 9.35g(수율 82%)을 얻었다: GC-Mass (이론치: 582.16 g/mol, 측정치: 582 g/mol)
9.35 g (yield 82%) of the desired compound was obtained by carrying out the same procedure as in [Preparation Example 39], except that 1-ethynylnaphthalene was used as the reactant. GC-Mass (calc .: 582.16 g / mol, measured: 582 g / mol)

[준비예 46][Preparation Example 46]

a-46 합성a-46 synthesis

2,2',2''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리페닐렌의 합성Synthesis of 2,2 ', 2 "- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-2,1-diyl)) triphenylene

Figure pat00059
Figure pat00059

반응물로 2-에티닐트리페닐렌을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 14.6g(수율 85%)을 얻었다: GC-Mass (이론치: 882.25 g/mol, 측정치: 882 g/mol)
(Yield: 85%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 2-ethynyltriphenylene was used as the reactant. GC-Mass (theoretical value: 882.25 g / mol, : 882 g / mol)

[준비예 47][Preparation Example 47]

a-47 합성a-47 synthesis

3,3',3''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리스(9-페닐-9H-카바졸)의 합성3, 3 ', 3' '- ((2,4,6-Trifluorobenzene-1,3,5-triyl) tris (ethyne- Carbazole)

Figure pat00060
Figure pat00060

반응물로 3-에티닐-9-페닐-9H-카바졸을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 13.9g(수율 77%)을 얻었다: GC-Mass (이론치: 927.29 g/mol, 측정치: 927 g/mol)
(Yield: 77%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 3-ethynyl-9-phenyl-9H-carbazole was used as the reactant. GC- 927.29 g / mol, measured: 927 g / mol)

[준비예 48][Preparation Example 48]

a-48 합성a-48 synthesis

2,2',2''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리디벤조[b,d]티오펜의 합성(2,2 ', 2' '- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne- Synthesis of Thiophene

Figure pat00061
Figure pat00061

반응물로 2-에티닐디벤조[b,d]티오펜을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 11.7g(수율 80%)을 얻었다: GC-Mass (이론치: 750.08 g/mol, 측정치: 750 g/mol)
(Yield: 80%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 2-ethynyldibenzo [b, d] thiophene was used as the reactant. GC- g / mol, measurement: 750 g / mol)

[준비예 49][Preparation Example 49]

a-49 합성a-49 synthesis

3,3',3''-(((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리스(벤젠-4,1-디일))트리피리딘의 합성3, 3 ', 3 "- (((2,4,6-Trifluorobenzene-1,3,5-triyl) tris (ethyne-2,1-diyl)) tris -Diyl)) < / RTI > Synthesis of tripyridine

Figure pat00062
Figure pat00062

반응물로 3-(4-에티닐페닐)피리딘을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 11.2g(수율 86%)을 얻었다: GC-Mass (이론치: 663.19 g/mol, 측정치: 663 g/mol)
(Yield: 86%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 3- (4-ethynylphenyl) pyridine was used as the reactant. GC-Mass (theoretical value: 663.19 g / mol, measured: 663 g / mol)

[준비예 50][Preparation Example 50]

a-50 합성a-50 synthesis

3,3',3''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리피리딘의 합성Synthesis of 3,3 ', 3' '- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-1,1-diyl)) tripyridine

Figure pat00063
Figure pat00063

반응물로 3-에티닐피리딘을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 7.6g(수율 90%)을 얻었다: GC-Mass (이론치: 435.10 g/mol, 측정치: 435 g/mol)
(Yield: 90%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 3-ethynylpyridine was used as the reactant. GC-Mass (theoretical value: 435.10 g / mol, measurement: 435 g / mol)

[준비예 51][Preparation Example 51]

a-51 합성a-51 synthesis

4,4',4''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리스(플루오로벤젠)의 합성Synthesis of 4,4 ', 4 "- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-1,1-diyl)) tris (fluorobenzene)

Figure pat00064
Figure pat00064

반응물로 1-에티닐-4-플루오로벤젠을 사용한 것을 제외하고는 [준비예 39]와 동일한 과정을 수행하여 목적 화합물 7.62g(수율 80%)을 얻었다: GC-Mass (이론치: 486.08 g/mol, 측정치: 486 g/mol)
(Yield: 80%) was obtained by carrying out the same procedure as in [Preparation Example 39], except that 1-ethynyl-4-fluorobenzene was used as the reactant. GC-Mass (theoretical value: 486.08 g / mol, measurement: 486 g / mol)

[합성예 1] 화합물 1의 합성[Synthesis Example 1] Synthesis of Compound 1

1,2,4,5,7,8-헥사페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성1,2,4,5,7,8-hexaphenyl-4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole Synthesis of

Figure pat00065
Figure pat00065

질소 기류 하에서 준비예 2에서 제조된 화합물인 a-2 (5g, 12.61mmol), 벤즈알데히드 (4.4g, 41.6 mmol), FeCl3(0.67g, 4.16mmol)를 DMF 100 ml에 혼합하고 80℃에서 24시간 동안 교반하였다. 반응 종결 후 상온으로 온도를 낮추고 H2O 50ml를 천천히 적가하여 결정화시켰다. 생성된 고체 화합물을 여과하고 MeOH로 세척하였다. 얻어진 고체를 40℃ 훈풍건조하에 24시간동안 건조하여 목적화합물 5.6(69%)을 얻었다.The compound a-2 (5 g, 12.61 mmol), benzaldehyde (4.4 g, 41.6 mmol) and FeCl 3 (0.67 g, 4.16 mmol) prepared in Preparation Example 2 were mixed in DMF (100 ml) Lt; / RTI > After completion of the reaction, the temperature was lowered to room temperature, and 50 ml of H 2 O was slowly added dropwise to effect crystallization. The resulting solid compound was filtered and washed with MeOH. The obtained solid was dried under a warm air of 40 ° C for 24 hours to obtain the target compound 5.6 (69%).

GC-Mass (이론치: 654.25 g/mol, 측정치: 654g/mol)GC-Mass (calculated: 654.25 g / mol, measured: 654 g / mol)

1H-NMR: 8.12 (s, 6H), 7.58 (m, 24H)
 1 H-NMR: 8.12 (s , 6H), 7.58 (m, 24H)

[합성예 2] 화합물 2의 합성[Synthesis Example 2] Synthesis of Compound 2

2,5,8-트리([1,1'-비페닐]-4-일)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-trie ([1,1'-biphenyl] -4-yl) -1,4,7-triphenyl-4,7-dihydro-1H- benzo [1,2- d: 3 , 4-d ': 5,6-d "] triimidazole

Figure pat00066
Figure pat00066

반응물로 [1,1'-비페닐]-4-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.89g(수율 62%)을 얻었다: GC-Mass (이론치: 486.08 g/mol, 측정치: 486 g/mol); GC-Mass (이론치: 882.25 g/mol, 측정치: 882g/mol)
The procedure of Synthesis Example 1 was repeated except that [1,1'-biphenyl] -4-carbaldehyde was used as the reactant to obtain 6.89 g (yield 62%) of the target compound: GC-Mass : 486.08 g / mol, measured: 486 g / mol); GC-Mass (calculated: 882.25 g / mol, measured: 882 g / mol)

[합성예 3] 화합물 3의 합성[Synthesis Example 3] Synthesis of Compound 3

2,5,8-트리([1,1'-비페닐]-3-일)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-trie ([1,1'-biphenyl] -3-yl) -1,4,7-triphenyl-4,7-dihydro-1H- benzo [1,2- d: 3 , 4-d ': 5,6-d "] triimidazole

Figure pat00067
Figure pat00067

반응물로 [1,1'-비페닐]-3-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.7g(수율 70%)을 얻었다: GC-Mass (이론치: 882.35 g/mol, 측정치: 882 g/mol)
The procedure of Synthesis Example 1 was repeated except that [1,1'-biphenyl] -3-carbaldehyde was used as a reactant to obtain 7.7 g (yield 70%) of the desired compound: GC-Mass : 882.35 g / mol, measured: 882 g / mol)

[합성예 4] 화합물 4의 합성[Synthesis Example 4] Synthesis of Compound 4

2,5,8-트리(나프탈렌-2-일)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸)의 합성Synthesis of 2,5,8-tri (naphthalen-2-yl) -1,4,7-triphenyl-4,7-dihydro-1H- benzo [1,2- 6-d "] triimidazole)

Figure pat00068
Figure pat00068

반응물로 2-나프타알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.8g(수율 68%)을 얻었다: GC-Mass (이론치: 804.30 g/mol, 측정치: 804 g/mol)
(Yield: 68%) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that 2-naphthaldehyde was used as the reactant. GC-Mass (theoretical value: 804.30 g / mol, measurement value: 804 g / mol)

[합성예 5] 화합물 5의 합성[Synthesis Example 5] Synthesis of Compound 5

1,4,7-트리페닐-2,5,8-트리(퀴놀린-6-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-triphenyl-2,5,8-tri (quinolin-6-yl) -4,7-dihydro-1H- benzo [1,2- Synthesis of 6-d "] triimidazole

Figure pat00069
Figure pat00069

반응물로 퀴놀린-7-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.8g(수율 77%)을 얻었다: GC-Mass (이론치: 807.29 g/mol, 측정치: 807 g/mol)
(Yield: 77%) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that quinoline-7-carbaldehyde was used as the reactant. GC-Mass (theoretical value: 807.29 g / mol, 807 g / mol)

[합성예 6] 화합물 6의 합성[Synthesis Example 6] Synthesis of Compound 6

2,5,8-트리(펜안트렌-9-일)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tri (phenanthrene-9-yl) -1,4,7-triphenyl-4,7-dihydro-1H- benzo [1,2- , 6-d "] triimidazole

Figure pat00070
Figure pat00070

반응물로 펜안트렌-9-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 8.54g(수율 71%)을 얻었다: GC-Mass (이론치: 954.35 g/mol, 측정치: 954g/mol)
(Yield: 71%) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that phenanthrene-9-carbaldehyde was used as the reactant. GC-Mass (calculated value: 954.35 g / mol, : 954 g / mol)

[합성예 7] 화합물 7의 합성[Synthesis Example 7] Synthesis of Compound 7

2,5,8-트리(나프탈렌-1-일)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tri (naphthalen-1-yl) -1,4,7-triphenyl-4,7-dihydro-1H- benzo [1,2- Synthesis of 6-d "] triimidazole

Figure pat00071
Figure pat00071

반응물로 1-나프타알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.2g(수율 72%)을 얻었다: GC-Mass (이론치: 804.30 g/mol, 측정치: 804 g/mol)
(Yield: 72%) was obtained by carrying out the same procedure as in [Synthesis Example 1], except that 1-naphthaldehyde was used as the reactant. GC-Mass (theoretical value: 804.30 g / mol, measurement value: 804 g / mol)

[합성예 8] 화합물 8의 합성[Synthesis Example 8] Synthesis of Compound 8

4,4',4''-((2,4,6-트리플루오로벤젠-1,3,5-트리일)트리스(에틴-2,1-디일))트리스(플루오로벤젠)의 합성Synthesis of 4,4 ', 4 "- ((2,4,6-trifluorobenzene-1,3,5-triyl) tris (ethyne-1,1-diyl)) tris (fluorobenzene)

Figure pat00072
Figure pat00072

반응물로 트리페닐렌-2-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.6g(수율 55%)을 얻었다: GC-Mass (이론치: 1104.29 g/mol, 측정치: 1104 g/mol)
(Yield: 55%) was obtained by carrying out the same procedure as in [Synthesis Example 1], except that triphenylene-2-carbaldehyde was used as the reactant. GC-Mass (theoretical value: 1104.29 g / mol, Measured: 1104 g / mol)

[합성예 9] 화합물 9의 합성[Synthesis Example 9] Synthesis of Compound 9

2,5,8-트리스(3-(9H-카바졸-9-일)페닐)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tris (3- (9H-carbazol-9-yl) phenyl) -1,4,7-triphenyl-4,7-dihydro-1H- benzo [ , 4-d ': 5,6-d "] triimidazole

Figure pat00073
Figure pat00073

반응물로 3-(9H-카바졸-9-일)벤즈알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 8.4g(수율 58%)을 얻었다: GC-Mass (이론치: 1149.43 g/mol, 측정치: 1149g/mol)
(Yield: 58%) was obtained in the same manner as in [Synthesis Example 1], except that 3- (9H-carbazol-9-yl) benzaldehyde was used as the reactant. GC- 1149.43 g / mol, measured: 1149 g / mol)

[합성예 10] 화합물 10의 합성[Synthesis Example 10] Synthesis of Compound 10

1,4,7-트리페닐-2,5,8-트리스(9-페닐-9H-카바졸-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-triphenyl-2,5,8-tris (9-phenyl-9H-carbazol-3-yl) -4,7-dihydro-1H- benzo [ Synthesis of 4-d ': 5,6-d "] triimidazole

Figure pat00074
Figure pat00074

반응물로 9-페닐-9H-카바졸-3-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 8.1g(수율 56%)을 얻었다: GC-Mass (이론치: 1149.43 g/mol, 측정치: 1149 g/mol)
(Yield: 56%) was obtained in the same manner as in [Synthesis Example 1] except that 9-phenyl-9H-carbazole-3-carbaldehyde was used as a reaction product. GC- 1149.43 g / mol, measurement: 1149 g / mol)

[합성예 11] 화합물 11의 합성[Synthesis Example 11] Synthesis of Compound 11

2,5,8-트리스(디벤조[b,d]티오펜-2-일)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tris (dibenzo [b, d] thiophen-2-yl) -1,4,7-triphenyl-4,7-dihydro- , 4-d ': 5,6-d "] triimidazole

Figure pat00075
Figure pat00075

반응물로 디벤조[b,d]티오펜-2-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.5g(수율 62%)을 얻었다: GC-Mass (이론치: 972.22 g/mol, 측정치: 972 g/mol)
The procedure of Synthesis Example 1 was repeated except that dibenzo [b, d] thiophene-2-carbaldehyde was used as a reactant to obtain 7.5 g (yield 62% : 972.22 g / mol, measured: 972 g / mol)

[합성예 12] 화합물 12의 합성[Synthesis Example 12] Synthesis of Compound 12

1,4,7-트리페닐-2,5,8-트리스(3-(피리딘-3-일)페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-triphenyl-2,5,8-tris (3- (pyridin-3-yl) phenyl) -4,7-dihydro-1H- benzo [1,2- d ': 5,6-d "] triimidazole

Figure pat00076
Figure pat00076

반응물로 3-(피리딘-3-일)벤즈알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.00g(수율 63%)을 얻었다: GC-Mass (이론치: 885.34 g/mol, 측정치: 885g/mol)
(Yield: 63%) was obtained by following the same procedure as in [Synthesis Example 1], except that 3- (pyridin-3-yl) benzaldehyde was used as the reactant. GC-Mass (theoretical value: 885.34 g / mol, measurement: 885 g / mol)

[합성예 13] 화합물 13의 합성[Synthesis Example 13] Synthesis of Compound 13

2,5,8-트리(1,9-펜안트롤린2-일)-1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tri (1,9-phenanthroline 2-yl) -1,4,7-triphenyl-4,7-dihydro-1H- benzo [1,2- d ': 5,6-d "] triimidazole

Figure pat00077
Figure pat00077

반응물로 1,9-펜안트롤린-2-카바알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.5g(수율 62%)을 얻었다: GC-Mass (이론치: 960.32 g/mol, 측정치: 960 g/mol)
(Yield: 62%) was obtained by following the same procedure as in [Synthesis Example 1], except that 1,9-phenanthroline-2-carbaldehyde was used as the reactant. GC-Mass (theoretical value: 960.32 g / mol, measured: 960 g / mol)

[합성예 14] 화합물 14의 합성[Synthesis Example 14] Synthesis of Compound 14

((1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리일)트리스(벤젠-4,1-디일))트리스(페닐포스핀 옥사이드)의 합성((1,4,7-Triphenyl-4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole- , 8-triyl) tris (benzene-4,1-diyl)) tris (phenylphosphine oxide)

Figure pat00078
Figure pat00078

반응물로 4-(페닐하이드로포스포릴)벤즈알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.2g(수율 48%)을 얻었다: GC-Mass (이론치: 1026.28 g/mol, 측정치: 1026 g/mol)
(Yield: 48%) was obtained by carrying out the same procedure as in [Synthesis Example 1], except that 4- (phenylhydrophosphoryl) benzaldehyde was used as the reactant. GC-Mass (theoretical value: 1026.28 g / mol , Measurement: 1026 g / mol)

[합성예 15] 화합물 15의 합성[Synthesis Example 15] Synthesis of Compound 15

2,5,8-트리페닐-1,4,7-트리(피리딘-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-triphenyl-1,4,7-tri (pyridin-3-yl) -4,7-dihydro-1H- benzo [1,2- Synthesis of 6-d "] triimidazole

Figure pat00079
Figure pat00079

반응물로 a-4를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.6g(수율 56%)을 얻었다: GC-Mass (이론치: 657.24 g/mol, 측정치: 657g/mol)
(Theoretical value: 657.24 g / mol, measured value: 657 g / mol, yield: 56%) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that a- )

[합성예 16] 화합물 16의 합성[Synthesis Example 16] Synthesis of Compound 16

2,5,8-트리(나프탈렌-2-일)-1,4,7-트리(피리딘-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tri (naphthalen-2-yl) -1,4,7-tri (pyridin-3-yl) -4,7-dihydro-1H- benzo [1,2- -d ': 5,6-d' '] triimidazole

Figure pat00080
Figure pat00080

반응물로 a-4를 사용한 것을 제외하고는 [합성예 4]와 동일한 과정을 수행하여 목적 화합물 7.7g(수율 60%)을 얻었다: GC-Mass (이론치: 1026.28 g/mol, 측정치: 1026 g/mol)
(Theoretical value: 1026.28 g / mol, measured value: 1026 g / mol) was obtained in the same manner as in [Synthesis Example 4] except that a-4 was used as a reactant. mol)

[합성예 17] 화합물 17의 합성[Synthesis Example 17] Synthesis of Compound 17

1,4,7-트리(피리딘-3-일)-2,5,8-트리스(3-(피리딘-3-일)페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성(3-pyridin-3-yl) phenyl) -4,7-dihydro-1H-benzo [1,2- d: 3,4-d ': 5,6-d "] triimidazole

Figure pat00081
Figure pat00081

반응물로 a-4를 사용한 것을 제외하고는 [합성예 12]와 동일한 과정을 수행하여 목적 화합물 7.7g(수율 70%)을 얻었다: GC-Mass (이론치: 888.32 g/mol, 측정치: 888 g/mol)
(Theoretical value: 888.32 g / mol, measured value: 888 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 12] except that a-4 was used as a reactant. mol)

[합성예 18] 화합물 18의 합성[Synthesis Example 18] Synthesis of Compound 18

1,4,7-트리([1,1'-비페닐]-4-일)-2,5,8-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성4,7-dihydro-1H-benzo [1,2-d: 3 , 4-d ': 5,6-d "] triimidazole

Figure pat00082
Figure pat00082

반응물로 a-6을 사용한 것을 제외하고는 [합성예 1]와 동일한 과정을 수행하여 목적 화합물 5.5g(수율 78%)을 얻었다: GC-Mass (이론치: 882.35 g/mol, 측정치: 882 g/mol)
(Theoretical value: 882.35 g / mol, measured value: 882 g / mol) was obtained in the same manner as in [Synthesis Example 1] except that a- mol)

[합성예 19] 화합물 19의 합성[Synthesis Example 19] Synthesis of Compound 19

1,4,7-트리(나프탈렌-2-일)-2,5,8-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tri (naphthalen-2-yl) -2,5,8-triphenyl-4,7-dihydro-1H- benzo [1,2- Synthesis of 6-d "] triimidazole

Figure pat00083
Figure pat00083

반응물로 a-8을 사용한 것을 제외하고는 [합성예 1]와 동일한 과정을 수행하여 목적 화합물 5.8g(수율 80%)을 얻었다: GC-Mass (이론치: 804.30 g/mol, 측정치: 804 g/mol)
(Yield: 80%) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that a-8 was used as the reactant. GC-Mass (theoretical value: 804.30 g / mol, measurement value: 804 g / mol)

[합성예 20] 화합물 20의 합성[Synthesis Example 20] Synthesis of Compound 20

2,5,8-트리페닐-1,4,7-트리스(9-페닐-9H-카바졸-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-triphenyl-1,4,7-tris (9-phenyl-9H-carbazol-3-yl) -4,7-dihydro- Synthesis of 4-d ': 5,6-d "] triimidazole

Figure pat00084
Figure pat00084

반응물로 a-10을 사용한 것을 제외하고는 [합성예 1]와 동일한 과정을 수행하여 목적 화합물 4.8g(수율 75%)을 얻었다: GC-Mass (이론치: 1149.43 g/mol, 측정치: 1149 g/mol)
(Theoretical value: 1149.43 g / mol, measured value: 1149 g / mol) was obtained in the same manner as in [Synthesis Example 1] except that a- mol)

[합성예 21] 화합물 21의 합성[Synthesis Example 21] Synthesis of Compound 21

1,4,7-트리스(디벤조[b,d]티오펜-2-일)-2,5,8-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tris (dibenzo [b, d] thiophen-2-yl) -2,5,8-triphenyl-4,7-dihydro- , 4-d ': 5,6-d "] triimidazole

Figure pat00085
Figure pat00085

반응물로 a-12을 사용한 것을 제외하고는 [합성예 1]와 동일한 과정을 수행하여 목적 화합물 4.69g(수율 69%)을 얻었다: GC-Mass (이론치: 972.22 g/mol, 측정치: 972 g/mol)
(Theoretical value: 972.22 g / mol, measured value: 972 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that a-12 was used as a reactant. mol)

[합성예 22] 화합물 22의 합성[Synthesis Example 22] Synthesis of Compound 22

2,5,8-트리페닐-1,4,7-트리스(3-(피리딘-3-일)페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-triphenyl-1,4,7-tris (3- (pyridin-3-yl) phenyl) -4,7-dihydro-1H- benzo [1,2- d ': 5,6-d "] triimidazole

Figure pat00086
Figure pat00086

반응물로 a-14를 사용한 것을 제외하고는 [합성예 1]와 동일한 과정을 수행하여 목적 화합물 3.68g(수율 52%)을 얻었다: GC-Mass (이론치: 885.33 g/mol, 측정치: 885 g/mol)
(Theoretical value: 885.33 g / mol, measured value: 885 g / mol) was obtained in the same manner as in [Synthesis Example 1] except that a- mol)

[합성예 23] 화합물 23의 합성[Synthesis Example 23] Synthesis of Compound 23

2,5,8-트리([1,1'-비페닐]-4-일)-1,4,7-트리(나프탈렌-2-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-trie ([1,1'-biphenyl] -4-yl) -1,4,7-tri (naphthalen-2-yl) -4,7-dihydro- , 2-d: 3,4-d ': 5,6-d "] triimidazole

Figure pat00087
Figure pat00087

반응물로 a-8을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 7.7g(수율 82%)을 얻었다: GC-Mass (이론치: 1032.30 g/mol, 측정치: 1032 g/mol)
(Theoretical value: 1032.30 g / mol, measured value: 1032 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 3] except that a-8 was used as a reactant. mol)

[합성예 24] 화합물 24의 합성[Synthesis Example 24] Synthesis of Compound 24

1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-triphenyl-4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole

Figure pat00088
Figure pat00088

반응물로 포름알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 4.2g(수율 80%)을 얻었다: GC-Mass (이론치: 426.16 g/mol, 측정치: 426 g/mol)
(Yield: 80%) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that formaldehyde was used as the reactant. GC-Mass (calculated value: 426.16 g / mol, measured value: 426 g / mol )

[합성예 25] 화합물 25의 합성[Synthesis Example 25] Synthesis of Compound 25

1,4,7-트리(피리딘-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tri (pyridin-3-yl) -4,7-dihydro-1H-benzo [1,2-d: 3,4- Synthesis of

Figure pat00089
Figure pat00089

반응물로 a-4를 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 4g(수율 76%)을 얻었다: GC-Mass (이론치: 429.15 g/mol, 측정치: 429 g/mol)
(Theoretical value: 429.15 g / mol, measured value: 429 g / mol, yield: 76%) was obtained by carrying out the same procedure as in [Synthesis Example 24] except that a- )

[합성예 26] 화합물 26의 합성[Synthesis Example 26] Synthesis of Compound 26

1,4,7-트리스(3-(피리딘-3-일)페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6-d' '] Synthesis of triimidazole

Figure pat00090
Figure pat00090

반응물로 a-16을 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 3.9g(수율 75%)을 얻었다: GC-Mass (이론치: 657.24 g/mol, 측정치: 657 g/mol)
(Theoretical value: 657.24 g / mol, measured value: 657 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 24] except that a-16 was used as the reactant. mol)

[합성예 27] 화합물 27의 합성[Synthesis Example 27] Synthesis of Compound 27

1,4,7-트리(나프탈렌-2-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tri (naphthalen-2-yl) -4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6- Synthesis of

Figure pat00091
Figure pat00091

반응물로 a-8을 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 3.9g(수율 74%)을 얻었다: GC-Mass (이론치: 576.21 g/mol, 측정치: 576 g/mol)
(Theoretical value: 576.21 g / mol, measured value: 576 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 24] except that a-8 was used as the reactant. mol)

[합성예 28] 화합물 28의 합성[Synthesis Example 28] Synthesis of Compound 28

1,4,7-트리스(트리페닐렌-2-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tris (triphenylene-2-yl) -4,7-dihydro-1H-benzo [1,2-d: 3,4- Synthesis of imidazole

Figure pat00092
Figure pat00092

반응물로 a-18을 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 3.52g(수율 68%)을 얻었다: GC-Mass (이론치: 876.30 g/mol, 측정치: 876 g/mol)
(Theoretical value: 876.30 g / mol, measured value: 876 g / mol) was obtained in the same manner as in [Synthesis Example 24] except that a-18 was used as the reactant. mol)

[합성예 29] 화합물 29의 합성[Synthesis Example 29] Synthesis of Compound 29

1,4,7-트리스(9-페닐-9H-카바졸-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tris (9-phenyl-9H-carbazol-3-yl) -4,7-dihydro-1H- benzo [1,2- d "] triimidazole

Figure pat00093
Figure pat00093

반응물로 a-10을 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 3.3g(수율 63%)을 얻었다: GC-Mass (이론치: 921.33 g/mol, 측정치: 921 g/mol)
(Theoretical value: 921.33 g / mol, measured value: 921 g / mol) was obtained in the same manner as in [Synthesis Example 24] except that a- mol)

[합성예 30] 화합물 30의 합성[Synthesis Example 30] Synthesis of Compound 30

1,4,7-트리스(디벤조[b,d]티오펜-2-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성1,4,7-Tris (dibenzo [b, d] thiophen-2-yl) -4,7-dihydro-1H- benzo [1,2- -d "] triimidazole

Figure pat00094
Figure pat00094

반응물로 a-20을 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 3g(수율 58%)을 얻었다: GC-Mass (이론치: 744.12 g/mol, 측정치: 744 g/mol)
3 g (yield 58%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 24] except that a-20 was used as the reactant. GC-Mass (744.12 g / mol, measured: 744 g / mol )

[합성예 31] 화합물 31의 합성[Synthesis Example 31] Synthesis of Compound 31

1,4,7-트리스(9-메틸-1,10-펜안트롤린2-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tris (9-methyl-1,10-phenanthroline 2-yl) -4,7-dihydro-1H- benzo [1,2- Synthesis of 6-d "] triimidazole

Figure pat00095
Figure pat00095

반응물로 a-22를 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 2.3g(수율 45%)을 얻었다: GC-Mass (이론치: 774.27 g/mol, 측정치: 774 g/mol)
(Theoretical value: 774.27 g / mol, measured value: 774 g / mol) was obtained in the same manner as in [Synthesis Example 24] except that a-22 was used as the reactant. mol)

[합성예 32] 화합물 32의 합성[Synthesis Example 32] Synthesis of Compound 32

((1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리일)트리스(벤젠-4,1-디일))트리스(페닐포스핀 옥사이드)의 합성((1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole-1,4,7-triyl) tris (benzene- ) Synthesis of tris (phenylphosphine oxide)

Figure pat00096
Figure pat00096

반응물로 a-24를 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 1.95g(수율 42%)을 얻었다: GC-Mass (이론치: 798.18 g/mol, 측정치: 798 g/mol)
(Theoretical value: 798.18 g / mol, measured value: 798 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 24] except that a-24 was used as the reactant. mol)

[합성예 33] 화합물 33의 합성[Synthesis Example 33] Synthesis of Compound 33

1,4,7-트리스(4-(피리딘-3-일)페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tris (4- (pyridin-3-yl) phenyl) -4,7-dihydro-1H- benzo [1,2- '] Synthesis of triimidazole

Figure pat00097
Figure pat00097

반응물로 a-26을 사용한 것을 제외하고는 [합성예 24]과 동일한 과정을 수행하여 목적 화합물 2.4g(수율 65%)을 얻었다: GC-Mass (이론치: 657.24 g/mol, 측정치: 657 g/mol)
(Theoretical value: 657.24 g / mol, measured value: 657 g / mol) was obtained in the same manner as in [Synthesis Example 24] except that a-26 was used as the reactant. mol)

[합성예 34] 화합물 34의 합성[Synthesis Example 34] Synthesis of Compound 34

1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,2,4,5,7,8-헥사카보니트릴의 합성Synthesis of 1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole-1,2,4,5,7,8-hexacarbonitrile

Figure pat00098
Figure pat00098

반응물로 a-28을 사용한 것을 제외하고는 [합성예 35]과 동일한 과정을 수행하여 목적 화합물 5.8g(수율 82%)을 얻었다: GC-Mass (이론치: 348.04 g/mol, 측정치: 348 g/mol)
(Theoretical value: 348.04 g / mol, measured value: 348 g / mol) was obtained in the same manner as in [Synthesis Example 35] except that a-28 was used as a reactant. mol)

[합성예 35] 화합물 35의 합성[Synthesis Example 35] Synthesis of Compound 35

1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리카보니트릴의 합성1,4,7-Triphenyl-4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole-2,5,8 - Synthesis of tricarbonitrile

Figure pat00099
Figure pat00099

반응물로 포밀 시아나이드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 5.5g(수율 88%)을 얻었다: GC-Mass (이론치: 501.15 g/mol, 측정치: 501 g/mol)
(Theoretical value: 501.15 g / mol, measured value: 501 g / mol) was obtained in the same manner as in [Synthesis Example 1] except that formalin cyanide was used as a reactant. mol)

[합성예 36] 화합물 36의 합성[Synthesis Example 36] Synthesis of Compound 36

1,4,7-트리(피리딘-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리카보니트릴의 합성Synthesis of 1,4,7-tri (pyridin-3-yl) -4,7-dihydro-1H-benzo [1,2-d: 3,4- Synthesis of 2,5,5-tricarbonitrile

Figure pat00100
Figure pat00100

반응물로 a-4를 사용한 것을 제외하고는 [합성예 35]과 동일한 과정을 수행하여 목적 화합물 4.9g(수율 79%)을 얻었다: GC-Mass (이론치: 504.13 g/mol, 측정치: 504 g/mol)
(Theoretical value: 504.13 g / mol, measured value: 504 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 35] except that a-4 was used as a reactant. mol)

[합성예 37] 화합물 37의 합성[Synthesis Example 37] Synthesis of Compound 37

1,4,7-트리([1,1'-비페닐]-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리카보니트릴의 합성Benzo [1,2-d: 3,4-d ': 5,6-dihydro-lH- -d "] triimidazole-2,5,8-tricarbonitrile

Figure pat00101
Figure pat00101

반응물로 a-16을 사용한 것을 제외하고는 [합성예 35]과 동일한 과정을 수행하여 목적 화합물 4.3g(수율 74%)을 얻었다: GC-Mass (이론치: 729.24 g/mol, 측정치: 729 g/mol)
(Theoretical value: 729.24 g / mol, measured value: 729 g / mol) was obtained in the same manner as in [Synthesis Example 35] except that a-16 was used as the reactant. mol)

[합성예 38] 화합물 38의 합성[Synthesis Example 38] Synthesis of Compound 38

1,4,7-트리스(4-플루오로페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리카보니트릴의 합성Synthesis of 1,4,7-tris (4-fluorophenyl) -4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6- Synthesis of 2,5,5-tricarbonitrile

Figure pat00102
Figure pat00102

반응물로 a-30을 사용한 것을 제외하고는 [합성예 35]과 동일한 과정을 수행하여 목적 화합물 4.3g(수율 71%)을 얻었다: GC-Mass (이론치: 555.12 g/mol, 측정치: 555 g/mol)
(Theoretical value: 555.12 g / mol, measured value: 555 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 35] except that a-30 was used as a reactant. mol)

[합성예 39] 화합물 39의 합성[Synthesis Example 39] Synthesis of Compound 39

1,4,7-트리스(3,4-디시아노페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리카보니트릴의 합성1,4,7-Tris (3,4-dicyanophenyl) -4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6- Synthesis of imidazole-2,5,8-tricarbonitrile

Figure pat00103
Figure pat00103

반응물로 a-32을 사용한 것을 제외하고는 [합성예 35]과 동일한 과정을 수행하여 목적 화합물 4.2g(수율 71%)을 얻었다: GC-Mass (이론치: 651.12 g/mol, 측정치: 651 g/mol)
Mass (651.12 g / mol, measured: 651 g / mol) was obtained in the same manner as in [Synthesis Example 35] except that a-32 was used as the reactant. mol)

[합성예 40] 화합물 40의 합성[Synthesis Example 40] Synthesis of Compound 40

2,5,8-트리페닐-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리카보니트릴의 합성Synthesis of 2,5,8-triphenyl-1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole-1,4,7-tricarbonitrile

Figure pat00104
Figure pat00104

반응물로 a-28을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 8.1g(수율 79%)을 얻었다: GC-Mass (이론치: 501.15 g/mol, 측정치: 501 g/mol)
(Theoretical value: 501.15 g / mol, measured value: 501 g / mol) was obtained in the same manner as in [Synthesis Example 1] except that a- mol)

[합성예 41] 화합물 41의 합성[Synthesis Example 41] Synthesis of Compound 41

2,5,8-트리(피리딘-3-일)-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리카보니트릴의 합성Benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole-1,4,7- Synthesis of tricarbonitrile

Figure pat00105
Figure pat00105

반응물로 벤즈알데히드를 사용한 것을 제외하고는 [합성예 34]과 동일한 과정을 수행하여 목적 화합물 7.1g(수율 69%)을 얻었다: GC-Mass (이론치: 504.13 g/mol, 측정치: 504 g/mol)
(Theoretical value: 504.13 g / mol, measured value: 504 g / mol) was obtained in the same manner as in [Synthesis Example 34], except that benzaldehyde was used as the reactant.

[합성예 42] 화합물 42의 합성[Synthesis Example 42] Synthesis of Compound 42

2,5,8-트리([1,1'-비페닐]-3-일)-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리카보니트릴의 합성Benzo [1,2-d: 3,4-d ': 5,6-d "] thiophene Synthesis of Dissol-1,4,7-Tricarbonitrile

Figure pat00106
Figure pat00106

반응물로 a-28을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 10.6g(수율 71%)을 얻었다: GC-Mass (이론치: 729.79 g/mol, 측정치: 729 g/mol)
(Theoretical value: 729.79 g / mol, measured value: 729 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 3] except that a-28 was used as a reactant. mol)

[합성예 43] 화합물 43의 합성[Synthesis Example 43] Synthesis of Compound 43

2,5,8-트리스(4-플루오로페닐)-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리카보니트릴의 합성Synthesis of 2,5,8-tris (4-fluorophenyl) -1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole- Synthesis of tricarbonitrile

Figure pat00107
Figure pat00107

반응물로 4-플루오로벤즈알데히드를 사용한 것을 제외하고는 [합성예 34]과 동일한 과정을 수행하여 목적 화합물 8.6g(수율 86%)을 얻었다: GC-Mass (이론치: 555.12 g/mol, 측정치: 555 g/mol)
(Yield: 86%) was obtained by carrying out the same procedure as in [Synthesis Example 34], except that 4-fluorobenzaldehyde was used as the reactant. GC-Mass (theoretical value: 555.12 g / mol, g / mol)

[합성예 44] 화합물 44의 합성[Synthesis Example 44] Synthesis of Compound 44

2,5,8-트리스(3,4-dicyano페닐)-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리카보니트릴의 합성Synthesis of 2,5,8-tris (3,4-dicyano phenyl) -1H-benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole- - Synthesis of tricarbonitrile

Figure pat00108
Figure pat00108

반응물로 4-포밀프탈로니트릴을 사용한 것을 제외하고는 [합성예 34]과 동일한 과정을 수행하여 목적 화합물 10.8g(수율 81%)을 얻었다: GC-Mass (이론치: 651.56 g/mol, 측정치: 651 g/mol)
(Yield: 81%) was obtained by carrying out the same procedure as in [Synthesis Example 34], except that 4-formylphthalonitrile was used as the reactant. GC-Mass (theoretical value: 651.56 g / mol, 651 g / mol)

[합성예 45] 화합물 45의 합성[Synthesis Example 45] Synthesis of Compound 45

4,4',4''-(1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리일)트리프탈로니트릴의 합성4,4 ', 4' '- (1H-benzo [1,2-d: 3,4-d': 5,6-d "] triimidazole- Synthesis of Talonitrile

Figure pat00109
Figure pat00109

반응물로 포름알데히드를 사용한 것을 제외하고는 [합성예 39]과 동일한 과정을 수행하여 목적 화합물 4.2g(수율 80%)을 얻었다: GC-Mass (이론치: 576.13 g/mol, 측정치: 576 g/mol)
(Theoretical value: 576.13 g / mol, measured value: 576 g / mol, yield: 80%) was obtained in the same manner as in [Synthesis Example 39], except that formaldehyde was used as the reactant. )

[합성예 46] 화합물 46의 합성[Synthesis Example 46] Synthesis of Compound 46

4,4',4''-(2,5,8-트리페닐-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리일)트리프탈로니트릴의 합성4,4 ', 4' '- (2,5,8-Triphenyl-1H-benzo [1,2-d: 3,4-d': 5,6- Synthesis of 4,7-triyl) tripalonitrile

Figure pat00110
Figure pat00110

반응물로 벤즈알데히드를 사용한 것을 제외하고는 [합성예 39]과 동일한 과정을 수행하여 목적 화합물 5.7g(수율 78%)을 얻었다: GC-Mass (이론치: 804.82 g/mol, 측정치: 804 g/mol)
(Theoretical value: 804.82 g / mol, measurement value: 804 g / mol) was obtained in the same manner as in [Synthesis Example 39], except that benzaldehyde was used as the reactant.

[합성예 47] 화합물 47의 합성[Synthesis Example 47] Synthesis of Compound 47

4,4',4''-(1,4,7-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리일)트리프탈로니트릴의 합성Synthesis of 4,4 ', 4 "- (1,4,7-triphenyl-4,7-dihydro-1H-benzo [1,2- ] Triimidazole-2,5, 8-triyl) tripthalonitrile

Figure pat00111
Figure pat00111

반응물로 a-2을 사용한 것을 제외하고는 [합성예 44]와 동일한 과정을 수행하여 목적 화합물 8.11g(수율 80%)을 얻었다: GC-Mass (이론치: 804.82 g/mol, 측정치: 804 g/mol)
(Theoretical value: 804.82 g / mol, measured value: 804 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 44] except that a-2 was used as the reactant. mol)

[합성예 48] 화합물 48의 합성[Synthesis Example 48] Synthesis of Compound 48

4,4',4''-(1,4,7-트리스(3-(피리딘-3-일)페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리일)트리프탈로니트릴의 합성4,4 ', 4 "- (1,4,7-tris (3- (pyridin-3-yl) phenyl) -4,7-dihydro-1H- benzo [1,2- -d ': 5,6-d "'] triimidazole-2,5,8-triyl) tripthalonitrile

Figure pat00112
Figure pat00112

반응물로 a-14을 사용한 것을 제외하고는 [합성예 44]와 동일한 과정을 수행하여 목적 화합물 5.1g(수율 62%)을 얻었다: GC-Mass (이론치: 1036.07 g/mol, 측정치: 1036 g/mol)
(Theoretical value: 1036.07 g / mol, measured value: 1036 g / mol) was obtained in the same manner as in [Synthesis Example 44], except that a- mol)

[합성예 49] 화합물 49의 합성[Synthesis Example 49] Synthesis of Compound 49

4,4',4''-(1,4,7-트리스(4-플루오로페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리일)트리프탈로니트릴의 합성Synthesis of 4,4 ', 4 "- (1,4,7-tris (4-fluorophenyl) -4,7-dihydro-1H- benzo [1,2- , 6-d "] triimidazole-2,5, 8-triyl) tripthalonitrile

Figure pat00113
Figure pat00113

반응물로 a-30을 사용한 것을 제외하고는 [합성예 44]와 동일한 과정을 수행하여 목적 화합물 6.6g(수율 70%)을 얻었다: GC-Mass (이론치: 858.20 g/mol, 측정치: 858 g/mol)
(Theoretical value: 858.20 g / mol, measured value: 858 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 44] except that a-30 was used as a reactant. mol)

[합성예 50] 화합물 50의 합성[Synthesis Example 50] Synthesis of Compound 50

4,4',4''-(2,5,8-트리스(4-플루오로페닐)-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리일)트리프탈로니트릴의 합성Benzo [1,2-d: 3,4-d ': 5,6-d' '] thiophene- Triimidazole-1, 4,7-triyl) tripthalonitrile

Figure pat00114
Figure pat00114

반응물로 4-플루오로벤즈알데히드를 사용한 것을 제외하고는 [합성예 39]과 동일한 과정을 수행하여 목적 화합물 6.12g(수율 78%)을 얻었다: GC-Mass (이론치: 858.20 g/mol, 측정치: 858 g/mol)
(Yield: 78%) was obtained by carrying out the same procedure as in [Synthesis Example 39], except that 4-fluorobenzaldehyde was used as the reactant. GC-Mass (theoretical value: 858.20 g / mol, measured value: 858 g / mol)

[합성예 51] 화합물 51 합성[Synthesis Example 51] Synthesis of Compound 51

4,4',4''-(2,5,8-트리스(4-플루오로페닐)-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리일)트리프탈로니트릴의 합성Benzo [1,2-d: 3,4-d ': 5,6-d' '] thiophene- Triimidazole-1, 4,7-triyl) tripthalonitrile

Figure pat00115
Figure pat00115

반응물로 a-32를 사용한 것을 제외하고는 [합성예 44]과 동일한 과정을 수행하여 목적 화합물 6.5g(수율 76%)을 얻었다: GC-Mass (이론치: 947.19 g/mol, 측정치: 947 g/mol)
(Theoretical value: 947.19 g / mol, measured value: 947 g / mol) was obtained in the same manner as in [Synthesis Example 44] except that a-32 was used as the reactant. mol)

[합성예 52] 화합물 52 합성[Synthesis Example 52] Synthesis of Compound 52

2,5,8-트리페닐-1,4,7-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Benzo [1,2-d: 3,4-d ': 5,6-d' '] thiophene- Synthesis of triimidazole

Figure pat00116
Figure pat00116

반응물로 a-34를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 8g(수율 86%)을 얻었다: GC-Mass (이론치: 552.30 g/mol, 측정치: 552 g/mol)
(Theoretical value: 552.30 g / mol, measured value: 552 g / mol, yield: 86%) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that a- )

[합성예 53] 화합물 53 합성[Synthesis Example 53] Synthesis of Compound 53

1,4,7-트리프로필-2,5,8-트리(피리딘-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,5- Synthesis of 6-d "] triimidazole

Figure pat00117
Figure pat00117

반응물로 a-34를 사용한 것을 제외하고는 [합성예 41]과 동일한 과정을 수행하여 목적 화합물 8.25g(수율 88%)을 얻었다: GC-Mass (이론치: 555.29 g/mol, 측정치: 552 g/mol)
(Theoretical value: 555.29 g / mol, measured value: 552 g / mol) was obtained in the same manner as in [Synthesis Example 41], except that a- mol)

[합성예 54] 화합물 54 합성[Synthesis Example 54] Synthesis of Compound 54

1,4,7-트리이소부틸-2,5,8-트리페닐-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-triisobutyl-2,5,8-triphenyl-4,7-dihydro-1H-benzo [1,2-d: 3,4- ] Synthesis of triimidazole

Figure pat00118
Figure pat00118

반응물로 a-36을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 7.00g(수율 80%)을 얻었다: GC-Mass (이론치: 594.35 g/mol, 측정치: 594 g/mol)
(Theoretical value: 594.35 g / mol, measured value: 594 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 1] except that a-36 was used as a reactant. mol)

[합성예 55] 화합물 55 합성[Synthesis Example 55] Synthesis of Compound 55

2,5,8-트리스(9,9-디메틸-9H-플루오렌-3-일)-1,4,7-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tris (9,9-dimethyl-9H-fluoren-3-yl) -1,4,7-tripropyl- Synthesis of 3,4-d ': 5,6-d "] triimidazole

Figure pat00119
Figure pat00119

반응물로 9,9-디메틸-9H-플루오렌-3-카바알데히드를 사용한 것을 제외하고는 [합성예 52]과 동일한 과정을 수행하여 목적 화합물 13.6g(수율 89%)을 얻었다: GC-Mass (이론치: 900.49 g/mol, 측정치: 900 g/mol)
(Yield 89%) was obtained by carrying out the same procedure as in [Synthesis Example 52], except that 9,9-dimethyl-9H-fluorene-3-carbaldehyde was used as the reactant: GC-Mass Theoretical value: 900.49 g / mol, a measurement value: 900 g / mol)

[합성예 56] 화합물 56 합성[Synthesis Example 56] Synthesis of Compound 56

2,5,8-트리([1,1'-비페닐]-3-일)-1,4,7-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-trie ([1,1'-biphenyl] -3-yl) -1,4,7-tripropyl-4,7-dihydro-1H- benzo [1,2- d: 3 , 4-d ': 5,6-d "] triimidazole

Figure pat00120
Figure pat00120

반응물로 a-34를 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 11.2g(수율 85%)을 얻었다: GC-Mass (이론치: 780.39 g/mol, 측정치: 780 g/mol)
(Theoretical value: 780.39 g / mol, measured value: 780 g / mol) was obtained in the same manner as in [Synthesis Example 3] except that a-34 was used as the reactant. mol)

[합성예 57] 화합물 57 합성[Synthesis Example 57] Synthesis of Compound 57

1,4,7-트리프로필-2,5,8-트리스(3-(피리딘-3-일)페닐)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tripropyl-2,5,8-tris (3- (pyridin-3-yl) phenyl) -4,7-dihydro-1H- benzo [1,2- d ': 5,6-d "] triimidazole

Figure pat00121
Figure pat00121

반응물로 a-34를 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 11.1g(수율 84%)을 얻었다: GC-Mass (이론치: 783.38 g/mol, 측정치: 783 g/mol)
(Theoretical value: 783.38 g / mol, measured value: 783 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 12] except that a-34 was used as the reactant. mol)

[합성예 58] 화합물 58 합성[Synthesis Example 58] Synthesis of Compound 58

4,4',4''-(1,4,7-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리일)트리프탈로니트릴의 합성4,4 ', 4' '- (1,4,7-tripropyl-4,7-dihydro-1H-benzo [1,2- ] Triimidazole-2,5, 8-triyl) tripthalonitrile

Figure pat00122
Figure pat00122

반응물로 a-34를 사용한 것을 제외하고는 [합성예 47]과 동일한 과정을 수행하여 목적 화합물 9.78g(수율 82%)을 얻었다: GC-Mass (이론치: 702.27 g/mol, 측정치: 702 g/mol)
(Theoretical value: 702.27 g / mol, measured value: 702 g / mol) was obtained in the same manner as in [Synthesis Example 47], except that a-34 was used as a reactant. mol)

[합성예 59] 화합물 59 합성[Synthesis Example 59] Synthesis of Compound 59

2,5,8-트리스(9-메틸-1,10-펜안트롤린2-일)-1,4,7-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 2,5,8-tris (9-methyl-1,10-phenanthroline 2-yl) -1,4,7-tripropyl-4,7-dihydro- Synthesis of 3,4-d ': 5,6-d "] triimidazole

Figure pat00123
Figure pat00123

반응물로 a-34를 사용한 것을 제외하고는 [합성예 13]과 동일한 과정을 수행하여 목적 화합물 13g(수율 85%)을 얻었다: GC-Mass (이론치: 900.41 g/mol, 측정치: 900 g/mol)
(Yield: 85%) was obtained by carrying out the same procedure as in [Synthesis Example 13], except that a-34 was used as the reactant. GC-Mass (calcd .: 900.41 g / mol, measurement: 900 g / mol )

[합성예 60] 화합물 60 합성[Synthesis Example 60] Synthesis of Compound 60

((1,4,7-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-2,5,8-트리일)트리스(벤젠-3,1-디일))트리스(페닐포스핀 옥사이드)의 합성((1,4,7-tripropyl-4,7-dihydro-1H-benzo [1,2-d: 3,4-d ': 5,6-d " , 8-triyl) tris (benzene-3,1-diyl)) tris (phenylphosphine oxide)

Figure pat00124
Figure pat00124

반응물로 a-34를을 사용한 것을 제외하고는 [합성예 14]과 동일한 과정을 수행하여 목적 화합물 13.8g(수율 88%)을 얻었다: GC-Mass (이론치: 924.32 g/mol, 측정치: 924 g/mol)
(Yield: 88%) was obtained by carrying out the same procedure as in [Synthesis Example 14] except that a-34 was used as the reactant. GC-Mass (theoretical value: 924.32 g / mol, measurement value: 924 g / mol)

[합성예 61] 화합물 61 합성[Synthesis Example 61] Synthesis of Compound 61

1,4,7-트리페닐-2,5,8-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Benzo [1,2-d: 3,4-d ': 5,6-d' '] thiophene- Synthesis of triimidazole

Figure pat00125
Figure pat00125

반응물로 부티르알데히드를 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.2g(수율 90%)을 얻었다: GC-Mass (이론치: 552.30 g/mol, 측정치: 552 g/mol)
(Theoretical value: 552.30 g / mol, measured value: 552 g / mol) was obtained in the same manner as in [Synthesis Example 1] except that butyraldehyde was used as the reactant. mol)

[합성예 62] 화합물 62 합성[Synthesis Example 62] Synthesis of Compound 62

2,5,8-트리프로필-1,4,7-트리(피리딘-3-일)-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Dihydro-1H-benzo [1,2-d: 3,4-d ': 5,5- Synthesis of 6-d "] triimidazole

Figure pat00126
Figure pat00126

반응물로 a-4를 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 5.1g(수율 74%)을 얻었다: GC-Mass (이론치: 552.29 g/mol, 측정치: 552 g/mol)
(Theoretical value: 552.29 g / mol, measured value: 552 g / mol) was obtained in the same manner as in [Synthesis Example 61], except that a-4 was used as a reactant. mol)

[합성예 63] 화합물 63 합성[Synthesis Example 63] Synthesis of Compound 63

1,4,7-트리페닐-2,5,8-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Benzo [1,2-d: 3,4-d ': 5,6-d' '] thiophene- Synthesis of triimidazole

Figure pat00127
Figure pat00127

반응물로 3-메틸부탄알을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 6.1g(수율 82%)을 얻었다: GC-Mass (이론치: 594.79 g/mol, 측정치: 594 g/mol)
(Yield: 82%) was obtained by following the same procedure as in [Synthesis Example 1], except that 3-methyl butanal was used as the reactant. GC-Mass (theoretical value: 594.79 g / mol, measurement value: 594 g / mol)

[합성예 64] 화합물 64 합성[Synthesis Example 64] Synthesis of Compound 64

1,4,7-트리스(9,9-디메틸-9H-플루오렌-3-일)-2,5,8-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성1,7-dihydro-1H-benzo [1,2-d: 4,7-dihydro- Synthesis of 3,4-d ': 5,6-d "] triimidazole

Figure pat00128
Figure pat00128

반응물로 a-38을 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 4.3g(수율 72%)을 얻었다: GC-Mass (이론치: 900.49 g/mol, 측정치: 900 g/mol)
(Yield: 72%) was obtained by carrying out the same procedure as in [Synthesis Example 61] except that a-38 was used as the reactant. GC-Mass (theoretical value: 900.49 g / mol, measurement value: 900 g / mol)

[합성예 65] 화합물 65 합성[Synthesis Example 65] Synthesis of Compound 65

1,4,7-트리스(9-페닐-9H-카바졸-3-일)-2,5,8-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tris (9-phenyl-9H-carbazol-3-yl) -2,5,8-tripropyl-4,7-dihydro- Synthesis of 4-d ': 5,6-d "] triimidazole

반응물로 a-10을 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 3.5g(수율 58%)을 얻었다: GC-Mass (이론치: 1047.47 g/mol, 측정치: 1047 g/mol)
(Theoretical value: 1047.47 g / mol, measured value: 1047 g / mol) was obtained in the same manner as in [Synthesis Example 61], except that a- mol)

[합성예 66] 화합물 66 합성[Synthesis Example 66] Synthesis of Compound 66

1,4,7-트리(나프탈렌-2-일)-2,5,8-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tri (naphthalen-2-yl) -2,5,8-tripropyl-4,7-dihydro-1H- benzo [1,2- Synthesis of 6-d "] triimidazole

Figure pat00130
Figure pat00130

반응물로 a-8을 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 4.6g(수율 73%)을 얻었다: GC-Mass (이론치: 702.25 g/mol, 측정치: 702 g/mol)
(Theoretical value: 702.25 g / mol, measured value: 702 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 61] except that a-8 was used as a reactant. mol)

[합성예 67] 화합물 67 합성[Synthesis Example 67] Synthesis of Compound 67

1,4,7-트리([1,1'-비페닐]-4-일)-2,5,8-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tri [(1,1'-biphenyl] -4-yl) -2,5,8-tripropyl-4,7-dihydro-1H- benzo [1,2- d: 3 , 4-d ': 5,6-d "] triimidazole

Figure pat00131
Figure pat00131

반응물로 a-6을 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 4.8g(수율 77%)을 얻었다: GC-Mass (이론치: 781.39 g/mol, 측정치: 781 g/mol)
(Yield: 77%) was obtained in the same manner as in [Synthesis Example 61], except that a-6 was used as the reactant. GC-Mass (theoretical value: 781.39 g / mol, measurement value: 781 g / mol)

[합성예 68] 화합물 68 합성[Synthesis Example 68] Synthesis of Compound 68

1,4,7-트리스(4-플루오로페닐)-2,5,8-트리프로필-4,7-디하이드로-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸의 합성Synthesis of 1,4,7-tris (4-fluorophenyl) -2,5,8-tripropyl-4,7-dihydro-1H- benzo [1,2- Synthesis of 6-d "] triimidazole

Figure pat00132
Figure pat00132

반응물로 a-30을 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 5.3g(수율 79%)을 얻었다: GC-Mass (이론치: 606.27 g/mol, 측정치: 606 g/mol)
(Theoretical value: 606.27 g / mol, measured value: 606 g / mol) was obtained in the same manner as in [Synthesis Example 61] except that a-30 was used as the reactant. mol)

[합성예 69] 화합물 69 합성[Synthesis Example 69] Synthesis of Compound 69

4,4',4''-(2,5,8-트리프로필-1H-벤조[1,2-d:3,4-d':5,6-d'']트리이미다졸-1,4,7-트리일)트리프탈로니트릴의 합성Benzo [1,2-d: 3,4-d ': 5,6-d "] triimidazole-1, Synthesis of 4,7-triyl) tripalonitrile

Figure pat00133
Figure pat00133

반응물로 a-32을 사용한 것을 제외하고는 [합성예 61]과 동일한 과정을 수행하여 목적 화합물 5.5g(수율 86%)을 얻었다: GC-Mass (이론치: 702.27 g/mol, 측정치: 702 g/mol)
(Theoretical value: 702.27 g / mol, measured value: 702 g / mol) was obtained in the same manner as in [Synthesis Example 61] except that a-32 was used as a reactant. mol)

[합성예 70] 화합물 70 합성[Synthesis Example 70] Synthesis of Compound 70

2,5,8-트리페닐벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-triphenylbenzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole)

Figure pat00134
Figure pat00134

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 1]과 동일한 과정을 수행하여 목적 화합물 11.2g(수율 90%)을 얻었다: GC-Mass (이론치: 429.11 g/mol, 측정치: 429 g/mol)
The procedure of Synthesis Example 1 was repeated except that 2,4,6-triaminobenzene-1,3,5-triol was used as a reactant to obtain 11.2 g (yield 90%) of the target compound: GC -Mass (theory: 429.11 g / mol, measurement: 429 g / mol)

[합성예 71] 화합물 71 합성[Synthesis Example 71] Synthesis of Compound 71

2,5,8-트리([1,1'-비페닐]-4-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Dibenzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole) Synthesis of

Figure pat00135
Figure pat00135

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 2]과 동일한 과정을 수행하여 목적 화합물 17.62g(수율 92%)을 얻었다: GC-Mass (이론치: 657.21 g/mol, 측정치: 657 g/mol)
17.62 g (yield 92%) of the desired compound was obtained by carrying out the same processes as in [Synthesis Example 2], except that 2,4,6-triaminobenzene-1,3,5-triol was used as a reactant: GC -Mass (theory: 657.21 g / mol, measurement: 657 g / mol)

[합성예 72] 화합물 72 합성[Synthesis Example 72] Synthesis of Compound 72

2,5,8-트리([1,1'-비페닐]-3-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성3,4-d ': 5,6-d' '] tris (oxazole) was used in place of 2,5,8-tri ([1,1'- Synthesis of

Figure pat00136
Figure pat00136

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 3]과 동일한 과정을 수행하여 목적 화합물 17.00g(수율 91%)을 얻었다: GC-Mass (이론치: 657.21 g/mol, 측정치: 657 g/mol)
(Yield: 91%) was obtained by carrying out the same processes as in [Synthesis Example 3], except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (theory: 657.21 g / mol, measurement: 657 g / mol)

[합성예 73] 화합물 73 합성[Synthesis Example 73] Synthesis of Compound 73

2,5,8-트리(나프탈렌-2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tri (naphthalen-2-yl) benzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole)

Figure pat00137
Figure pat00137

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 4]과 동일한 과정을 수행하여 목적 화합물 15.8g(수율 94%)을 얻었다: GC-Mass (이론치: 579.16 g/mol, 측정치: 579 g/mol)
The procedure of Synthetic Example 4 was repeated except that 2,4,6-triaminobenzene-1,3,5-triol was used as a reactant, to obtain 15.8 g (yield 94%) of the title compound: GC -Mass (theory: 579.16 g / mol, measurement: 579 g / mol)

[합성예 74] 화합물 74 합성[Synthesis Example 74] Synthesis of Compound 74

2,5,8-트리(퀴놀린-7-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tri (quinolin-7-yl) benzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole)

Figure pat00138
Figure pat00138

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 5]과 동일한 과정을 수행하여 목적 화합물 15.6g(수율 92%)을 얻었다: GC-Mass (이론치: 582.14 g/mol, 측정치: 582 g/mol)
The procedure of Synthesis Example 5 was repeated except that 2,4,6-triaminobenzene-1,3,5-triol was used as a reactant to obtain 15.6 g (yield 92%) of the target compound: GC -Mass (theory: 582.14 g / mol, measured: 582 g / mol)

[합성예 75] 화합물 75 합성[Synthesis Example 75] Synthesis of Compound 75

2,5,8-트리(펜안트렌-9-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tri (phenanthren-9-yl) benzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole)

Figure pat00139
Figure pat00139

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 6]과 동일한 과정을 수행하여 목적 화합물 18.9g(수율 89%)을 얻었다: GC-Mass (이론치: 729.21 g/mol, 측정치: 729 g/mol)
18.9 g (yield 89%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 6] except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (theory: 729.21 g / mol, measurement: 729 g / mol)

[합성예 76] 화합물 76 합성[Synthesis Example 76] Synthesis of Compound 76

2,5,8-트리(나프탈렌-1-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tri (naphthalen-1-yl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00140
Figure pat00140

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 7]과 동일한 과정을 수행하여 목적 화합물 15.7g(수율 93%)을 얻었다: GC-Mass (이론치: 579.16 g/mol, 측정치: 579 g/mol)
The procedure of Synthesis Example 7 was repeated except that 2,4,6-triaminobenzene-1,3,5-triol was used as a reactant, to obtain 15.7 g (yield 93%) of the desired compound: GC -Mass (theory: 579.16 g / mol, measurement: 579 g / mol)

[합성예 77] 화합물 77 합성[Synthesis Example 77] Synthesis of Compound 77

2,5,8-트리스(트리페닐렌-2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tris (triphenylene-2-yl) benzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole)

Figure pat00141
Figure pat00141

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 8]과 동일한 과정을 수행하여 목적 화합물 23.3g(수율 91%)을 얻었다: GC-Mass (이론치: 879.25 g/mol, 측정치: 879 g/mol)
23.3 g (yield 91%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 8] except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (theory: 879.25 g / mol, measurement: 879 g / mol)

[합성예 78] 화합물 78 합성[Synthesis Example 78] Synthesis of Compound 78

2,5,8-트리스(3-(9H-카바졸-9-일)페닐)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tris (3- (9H-carbazol-9-yl) phenyl) benzo [1,2- Synthesis of

Figure pat00142
Figure pat00142

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 9]과 동일한 과정을 수행하여 목적 화합물 24.2g(수율 90%)을 얻었다: GC-Mass (이론치: 924.28 g/mol, 측정치: 924 g/mol)
The same procedure as in [Synthesis Example 9] was conducted except that 2,4,6-triaminobenzene-1,3,5-triol was used as a reactant, to obtain 24.2 g (yield 90%) of the desired compound: GC -Mass (calculated: 924.28 g / mol, measured: 924 g / mol)

[합성예 79] 화합물 79 합성[Synthesis Example 79] Synthesis of Compound 79

2,5,8-트리스(9-페닐-9H-카바졸-3-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tris (9-phenyl-9H-carbazol-3-yl) benzo [1,2-d: 3,4-d ': 5,6- synthesis

Figure pat00143
Figure pat00143

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 10]과 동일한 과정을 수행하여 목적 화합물 23.7g(수율 88%)을 얻었다: GC-Mass (이론치: 924.28 g/mol, 측정치: 924 g/mol)
The procedure of Synthesis Example 10 was repeated except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant, to obtain 23.7 g (yield 88%) of the target compound: GC -Mass (calculated: 924.28 g / mol, measured: 924 g / mol)

[합성예 80] 화합물 80 합성[Synthesis Example 80] Synthesis of Compound 80

2,5,8-트리스(디벤조[b,d]티오펜-2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성2,5,5-tris (dibenzo [b, d] thiophen-2-yl) benzo [1,2- Synthesis of

Figure pat00144
Figure pat00144

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 11]과 동일한 과정을 수행하여 목적 화합물 18.9g(수율 87%)을 얻었다: GC-Mass (이론치: 747.07 g/mol, 측정치: 747 g/mol)
(Yield: 87%) was obtained by carrying out the same processes as in [Synthesis Example 11] except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (calculated: 747.07 g / mol, measured: 747 g / mol)

[합성예 81] 화합물 81 합성[Synthesis Example 81] Synthesis of Compound 81

2,5,8-트리(피리딘-3-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tri (pyridin-3-yl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00145
Figure pat00145

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 12]과 동일한 과정을 수행하여 목적 화합물 10.7g(수율 85%)을 얻었다: GC-Mass (이론치: 432.10 g/mol, 측정치: 432 g/mol)
The procedure of Synthesis Example 12 was repeated except that 2,4,6-triaminobenzene-1,3,5-triol was used as a reactant, to obtain 10.7 g (yield: 85%) of the desired compound: GC -Mass (theory: 432.10 g / mol, measured: 432 g / mol)

[합성예 82] 화합물 82 합성[Synthesis Example 82] Synthesis of Compound 82

2,5,8-트리스(9-메틸-1,10-펜안트롤린2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tris (9-methyl-1,10-phenanthroline 2-yl) benzo [1,2-d: 3,4-d ': 5,6- ) Synthesis of

Figure pat00146
Figure pat00146

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 13]과 동일한 과정을 수행하여 목적 화합물 16.1g(수율 71%)을 얻었다: GC-Mass (이론치: 777.22 g/mol, 측정치: 777 g/mol)
The procedure of Synthetic Example 13 was repeated except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant, to obtain 16.1 g (yield 71%) of the desired compound: GC -Mass (theory: 777.22 g / mol, measurement: 777 g / mol)

[합성예 83] 화합물 83 합성[Synthesis Example 83] Synthesis of Compound 83

(벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)-2,5,8-트리일트리스(벤젠-3,1-디일))트리스(페닐포스핀 옥사이드)의 합성(Benzo [1,2-d: 3,4-d ': 5,6-d' '] tris (oxazole) (Phenylphosphine oxide) Synthesis of

Figure pat00147
Figure pat00147

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 14]과 동일한 과정을 수행하여 목적 화합물 18.7g(수율 80%)을 얻었다: GC-Mass (이론치: 801.13 g/mol, 측정치: 801 g/mol)
18.7 g (yield 80%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 14] except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (theory: 801.13 g / mol, measurement: 801 g / mol)

[합성예 84] 화합물 84 합성[Synthesis Example 84] Synthesis of Compound 84

2,5,8-트리스(디벤조[b,d]티오펜-4-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성(Dibenzo [b, d] thiophen-4-yl) benzo [1,2-d: 3,4- Synthesis of

Figure pat00148
Figure pat00148

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 70]과 동일한 과정을 수행하여 목적 화합물 19.4g(수율 89%)을 얻었다: GC-Mass (이론치: 747.07 g/mol, 측정치: 747 g/mol)
19.4 g (yield 89%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 70] except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (calculated: 747.07 g / mol, measured: 747 g / mol)

[합성예 85] 화합물 85 합성[Synthesis Example 85] Synthesis of Compound 85

2,5,8-트리스(4-플루오로페닐)벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)의 합성Synthesis of 2,5,8-tris (4-fluorophenyl) benzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole)

Figure pat00149
Figure pat00149

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 43]과 동일한 과정을 수행하여 목적 화합물 11g(수율 78%)을 얻었다: GC-Mass (이론치: 483.08 g/mol, 측정치: 483 g/mol)
11 g (yield 78%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 43], except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC- Mass (theory: 483.08 g / mol, measurement: 483 g / mol)

[합성예 86] 화합물 86 합성[Synthesis Example 86] Synthesis of Compound 86

벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)-2,5,8-트리카보니트릴의 합성Synthesis of benzo [1,2-d: 3,4-d ': 5,6-d "] tris (oxazole) -2,5,8-tricarbonitrile

Figure pat00150
Figure pat00150

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 34]과 동일한 과정을 수행하여 목적 화합물 7.7g(수율 96%)을 얻었다: GC-Mass (이론치: 276.00 g/mol, 측정치: 276 g/mol)
(Yield: 96%) was obtained by carrying out the same procedure as in [Synthesis Example 34] except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (calculated: 276.00 g / mol, measured: 276 g / mol)

[합성예 87] 화합물 87 합성[Synthesis Example 87] Synthesis of Compound 87

4,4',4''-(벤조[1,2-d:3,4-d':5,6-d'']트리스(옥사졸)-2,5,8-트리일)트리프탈로니트릴의 합성4,4 ', 4' '- (benzo [1,2-d: 3,4-d': 5,6-d ''] tris (oxazole) Synthesis of Talonitrile

Figure pat00151
Figure pat00151

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리올을 사용한 것을 제외하고는 [합성예 44]과 동일한 과정을 수행하여 목적 화합물 15.5g(수율 92%)을 얻었다: GC-Mass (이론치: 579.18 g/mol, 측정치: 579 g/mol)
15.5 g (yield 92%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 44] except that 2,4,6-triaminobenzene-1,3,5-triol was used as the reactant: GC -Mass (theory: 579.18 g / mol, measurement: 579 g / mol)

[합성예 88] 화합물 88 합성[Synthesis Example 88] Synthesis of Compound 88

2,5,8-트리페닐벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-triphenylbenzo [1,2-d: 3,4-d ': 5,6-d "] tris (thiazole)

Figure pat00152
Figure pat00152

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 70]과 동일한 과정을 수행하여 목적 화합물 10.1g(수율 93%)을 얻었다: GC-Mass (이론치: 477.04 g/mol, 측정치: 477 g/mol)
The procedure of Synthetic Example 70 was repeated, except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant, to obtain 10.1 g (yield 93%) of the title compound: GC -Mass (theory: 477.04 g / mol, measurement: 477 g / mol)

[합성예 89] 화합물 89 합성[Synthesis Example 89] Synthesis of Compound 89

2,5,8-트리([1,1'-비페닐]-4-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Dibenzo [1,2-d: 3,4-d ': 5,6-d "] tris (thiazole) Synthesis of

Figure pat00153
Figure pat00153

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 71]과 동일한 과정을 수행하여 목적 화합물 14.4g(수율 90%)을 얻었다: GC-Mass (이론치: 705.14 g/mol, 측정치: 705 g/mol)
14.4 g (yield 90%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 71] except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theory: 705.14 g / mol, measurement: 705 g / mol)

[합성예 90] 화합물 90 합성[Synthesis Example 90] Synthesis of Compound 90

2,5,8-트리([1,1'-비페닐]-3-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Dibenzo [1,2-d: 3,4-d ': 5,6-d "] tris (thiazole) Synthesis of

Figure pat00154
Figure pat00154

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 72]과 동일한 과정을 수행하여 목적 화합물 14.1g(수율 88%)을 얻었다: GC-Mass (이론치: 705.14 g/mol, 측정치: 705 g/mol)
The same procedure as in [Synthesis Example 72] was conducted except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as a reaction product to obtain 14.1 g (yield 88%) of the desired compound: GC -Mass (theory: 705.14 g / mol, measurement: 705 g / mol)

[합성예 91] 화합물 91 합성[Synthesis Example 91] Synthesis of Compound 91

2,5,8-트리(나프탈렌-2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tri (naphthalen-2-yl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00155
Figure pat00155

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 73]과 동일한 과정을 수행하여 목적 화합물 12.7g(수율 89%)을 얻었다: GC-Mass (이론치: 627.09 g/mol, 측정치: 627 g/mol)
12.7 g (yield 89%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 73], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theory: 627.09 g / mol, measurement: 627 g / mol)

[합성예 92] 화합물 92 합성[Synthesis Example 92] Synthesis of Compound 92

2,5,8-트리(퀴놀린-7-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tri (quinolin-7-yl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00156
Figure pat00156

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 74]과 동일한 과정을 수행하여 목적 화합물 13.2g(수율 92%)을 얻었다: GC-Mass (이론치: 630.08 g/mol, 측정치: 630 g/mol)
13.2 g (yield 92%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 74], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theory: 630.08 g / mol, measurement: 630 g / mol)

[합성예 93] 화합물 93 합성[Synthesis Example 93] Synthesis of Compound 93

2,5,8-트리(펜안트렌-9-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tri (phenanthren-9-yl) benzo [1,2-d: 3,4-d ': 5,6-d "] tris

Figure pat00157
Figure pat00157

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 75]과 동일한 과정을 수행하여 목적 화합물 16.1g(수율 91%)을 얻었다: GC-Mass (이론치: 777.14 g/mol, 측정치: 777 g/mol)
(Yield: 91%) was obtained by carrying out the same procedure as in [Synthesis Example 75], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (calculated: 777.14 g / mol, measured: 777 g / mol)

[합성예 94] 화합물 94 합성[Synthesis Example 94] Synthesis of Compound 94

2,5,8-트리(나프탈렌-1-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tri (naphthalen-1-yl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00158
Figure pat00158

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 76]과 동일한 과정을 수행하여 목적 화합물 12.8g(수율 90%)을 얻었다: GC-Mass (이론치: 627.09 g/mol, 측정치: 627 g/mol)
12.8 g (yield 90%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 76], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theory: 627.09 g / mol, measurement: 627 g / mol)

[합성예 95] 화합물 95 합성[Synthesis Example 95] Synthesis of Compound 95

2,5,8-트리스(트리페닐렌-2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tris (triphenylene-2-yl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00159
Figure pat00159

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 77]과 동일한 과정을 수행하여 목적 화합물 18.3g(수율 87%)을 얻었다: GC-Mass (이론치: 927.18 g/mol, 측정치: 927 g/mol)
(Yield: 87%) was obtained by carrying out the same procedure as in [Synthesis Example 77], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (calculated: 927.18 g / mol, measured: 927 g / mol)

[합성예 96] 화합물 96 합성[Synthesis Example 96] Synthesis of Compound 96

2,5,8-트리스(3-(9H-카바졸-9-일)페닐)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tris (3- (9H-carbazol-9-yl) phenyl) benzo [1,2- Synthesis of

Figure pat00160
Figure pat00160

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 78]과 동일한 과정을 수행하여 목적 화합물 20.3g(수율 90%)을 얻었다: GC-Mass (이론치: 972.22 g/mol, 측정치: 972 g/mol)
(Yield: 90%) was obtained by carrying out the same procedure as in [Synthesis Example 78], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theoretical value: 972.22 g / mol, measurement: 972 g / mol)

[합성예 97] 화합물 97 합성[Synthesis Example 97] Synthesis of Compound 97

2,5,8-트리스(9-페닐-9H-카바졸-3-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tris (9-phenyl-9H-carbazol-3-yl) benzo [1,2-d: 3,4-d ': 5,6- synthesis

Figure pat00161
Figure pat00161

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 79]과 동일한 과정을 수행하여 목적 화합물 19.5g(수율 88%)을 얻었다: GC-Mass (이론치: 972.22 g/mol, 측정치: 972 g/mol)
19.5 g (yield 88%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 79], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theoretical value: 972.22 g / mol, measurement: 972 g / mol)

[합성예 98] 화합물 98 합성[Synthesis Example 98] Synthesis of Compound 98

2,5,8-트리스(디벤조[b,d]티오펜-2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성(Dibenzo [b, d] thiophen-2-yl) benzo [1,2-d: 3,4-d ': 5,6- Synthesis of

Figure pat00162
Figure pat00162

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 80]과 동일한 과정을 수행하여 목적 화합물 16.5g(수율 92%)을 얻었다: GC-Mass (이론치: 795.01 g/mol, 측정치: 795 g/mol)
16.5 g (yield 92%) of the title compound was obtained by carrying out the same processes as in [Synthesis Example 80], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as a reactant: GC -Mass (calculated: 795.01 g / mol, measured: 795 g / mol)

[합성예 99] 화합물 99 합성[Synthesis Example 99] Synthesis of Compound 99

2,5,8-트리(피리딘-3-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tri (pyridin-3-yl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00163
Figure pat00163

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 81]과 동일한 과정을 수행하여 목적 화합물 9.3g(수율 85%)을 얻었다: GC-Mass (이론치: 480.03 g/mol, 측정치: 480 g/mol)
9.3 g (yield 85%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 81], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theory: 480.03 g / mol, measurement: 480 g / mol)

[합성예 100] 화합물 100 합성[Synthesis Example 100] Synthesis of Compound 100

2,5,8-트리스(9-메틸-1,10-펜안트롤린2-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tris (9-methyl-1,10-phenanthroline 2-yl) benzo [1,2-d: 3,4- ) Synthesis of

Figure pat00164
Figure pat00164

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 82]과 동일한 과정을 수행하여 목적 화합물 14.6g(수율 78%)을 얻었다: GC-Mass (이론치: 825.16 g/mol, 측정치: 825 g/mol)
14.6 g (yield 78%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 82] except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theoretical value: 825.16 g / mol, measured: 825 g / mol)

[합성예 101] 화합물 101 합성[Synthesis Example 101] Synthesis of Compound 101

(벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)-2,5,8-트리일트리스(벤젠-3,1-디일))트리스(페닐포스핀 옥사이드)의 합성Tris (benzene-3,1-diyl) tris (thiazole) -2,5,8-tri tris (Phenylphosphine oxide) Synthesis of

Figure pat00165
Figure pat00165

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 83]과 동일한 과정을 수행하여 목적 화합물 15.4g(수율 80%)을 얻었다: GC-Mass (이론치: 847.05 g/mol, 측정치: 847 g/mol)
(Yield: 80%) was obtained by carrying out the same procedure as in [Synthesis Example 83], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theory: 847.05 g / mol, measured: 847 g / mol)

[합성예 102] 화합물 102 합성[Synthesis Example 102] Synthesis of Compound 102

2,5,8-트리스(디벤조[b,d]티오펜-4-일)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tris (dibenzo [b, d] thiophen-4-yl) benzo [1,2- Synthesis of

Figure pat00166
Figure pat00166

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 84]과 동일한 과정을 수행하여 목적 화합물 16.3g(수율 90%)을 얻었다: GC-Mass (이론치: 795.01 g/mol, 측정치: 795 g/mol)
16.3 g (yield 90%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 84], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (calculated: 795.01 g / mol, measured: 795 g / mol)

[합성예 103] 화합물 103 합성[Synthesis Example 103] Synthesis of Compound 103

2,5,8-트리스(4-플루오로페닐)벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)의 합성Synthesis of 2,5,8-tris (4-fluorophenyl) benzo [1,2-d: 3,4-d ': 5,6-d "

Figure pat00167
Figure pat00167

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 85]과 동일한 과정을 수행하여 목적 화합물 10.8g(수율 90%)을 얻었다: GC-Mass (이론치: 531.01 g/mol, 측정치: 531 g/mol)
10.8 g (yield 90%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 85], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theoretical value: 531.01 g / mol, measured: 531 g / mol)

[합성예 104] 화합물 104 합성[Synthesis Example 104] Synthesis of Compound 104

벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)-2,5,8-트리카보니트릴의 합성Synthesis of benzo [1,2-d: 3,4-d ': 5,6-d "] tris (thiazole) -2,5,8-tricarbonitrile

Figure pat00168
Figure pat00168

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 86]과 동일한 과정을 수행하여 목적 화합물 7g(수율 96%)을 얻었다: GC-Mass (이론치: 323.95 g/mol, 측정치: 324 g/mol)
7 g (yield: 96%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 86] except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as a reaction product. GC- Mass (theory: 323.95 g / mol, measured: 324 g / mol)

[합성예 105] 화합물 105 합성[Synthesis Example 105] Synthesis of Compound 105

4,4',4''-(벤조[1,2-d:3,4-d':5,6-d'']트리스(티아졸)-2,5,8-트리일)트리프탈로니트릴의 합성4,4 ', 4 "- (benzo [1,2-d: 3,4-d': 5,6-d ''] tris (thiazole) Synthesis of Talonitrile

Figure pat00169
Figure pat00169

반응물로 2,4,6-트리아미노벤젠-1,3,5-트리티올을 사용한 것을 제외하고는 [합성예 87]과 동일한 과정을 수행하여 목적 화합물 13.1g(수율 92%)을 얻었다: GC-Mass (이론치: 627.01 g/mol, 측정치: 627 g/mol)
13.1 g (yield 92%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 87], except that 2,4,6-triaminobenzene-1,3,5-trithiol was used as the reactant: GC -Mass (theoretical value: 627.01 g / mol, measurement: 627 g / mol)

[합성예 106] 화합물 106 합성[Synthesis Example 106] Synthesis of Compound 106

1,2,4,5,7,8-헥사페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성Synthesis of 1,2,4,5,7,8-hexaphenyl-4,7-dihydro-1H-dipyrrolo [2,3-e: 2 ', 3'-g] indole

Figure pat00170
Figure pat00170

질소 기류 하에서 아닐린(4.97g, 53.3mmol)을 DMSO 100ml에 녹인 후 온도를 0℃로 낮춘다. 0℃에서 NaH(1.53g, 64mmol)를 천천히 적가하였다. 0℃에서 30분 동안 교반 후 a-39 (7g, 16.18 mmol)를 천천히 적가하였다. 온도를 100℃로 천천히 올린 후 10시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 감압조건에서 농축한 후 컬럼크로마토그래피를 이용하여 목적 화합물을 8.2g(78%) 얻었다.Aniline (4.97 g, 53.3 mmol) is dissolved in 100 ml of DMSO under nitrogen flow, and the temperature is lowered to 0 ° C. At 0 < 0 > C, NaH (1.53 g, 64 mmol) was slowly added dropwise. After stirring at 0 C for 30 min a-39 (7 g, 16.18 mmol) was slowly added dropwise. The temperature was slowly raised to 100 < 0 > C and then stirred for 10 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and then 8.2 g (78%) of the target compound was obtained by column chromatography.

GC-Mass (이론치: 651.27 g/mol, 측정치: 651 g/mol)GC-Mass (calculated: 651.27 g / mol, measured: 651 g / mol)

1H-NMR: 7.78 (m, 6H), 7.51 (m, 24H)
 1 H-NMR: 7.78 (m , 6H), 7.51 (m, 24H)

[합성예 107] 화합물 107 합성[Synthesis Example 107] Synthesis of Compound 107

2,5,8-트리([1,1'-비페닐]-4-일)-1,4,7-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성1,7-dihydro-1H-dipyrrolo [2,3-e: 2 ', 3'-g] indole

Figure pat00171
Figure pat00171

반응물로 a-40을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 8.97g(수율 88%)을 얻었다: GC-Mass (이론치: 879.36 g/mol, 측정치: 879 g/mol)
(Yield: 88%) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-40 was used as the reactant. GC-Mass (theoretical value: 879.36 g / mol, measurement value: 879 g / mol)

[합성예 108] 화합물 108 합성[Synthesis Example 108] Synthesis of Compound 108

2,5,8-트리([1,1'-비페닐]-3-일)-1,4,7-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성Triphenyl-4,7-dihydro-1H-dipyrrolo [2,3-e: 2 ', 3'-g] indole

Figure pat00172
Figure pat00172

반응물로 a-41을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 8.82g(수율 86%)을 얻었다: GC-Mass (이론치: 879.36g/mol, 측정치: 879 g/mol)
(Theoretical value: 879.36 g / mol, measured value: 879 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-41 was used as a reactant. mol)

[합성예 109] 화합물 109 합성[Synthesis Example 109] Synthesis of Compound 109

2,5,8-트리(나프탈렌-2-일)-1,4,7-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성2,3-e: 2 ', 3 ' -g ' -biphenyl- Synthesis of indole

Figure pat00173
Figure pat00173

반응물로 a-42을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 8.6g(수율 90%)을 얻었다: GC-Mass (이론치: 801.31 g/mol, 측정치: 801 g/mol)
(Theoretical value: 801.31 g / mol, measured value: 801 g / mol) was obtained in the same manner as in [Synthesis Example 106] except that a-42 was used as a reactant. mol)

[합성예 110] 화합물 110 합성[Synthesis Example 110] Synthesis of Compound 110

2,5-di(나프탈렌-2-일)-1,4,7-트리페닐-8-(퀴놀린-6-일)-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성Dihydro-1H-dipyrrolo [2,3-e: 2, 4-dihydro- 2 ', 3'-g] indole

Figure pat00174
Figure pat00174

반응물로 a-43을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 8.3g(수율 87%)을 얻었다: GC-Mass (이론치: 802.31 g/mol, 측정치: 802 g/mol)
(Theoretical value: 802.31 g / mol, measured value: 802 g / mol) was obtained in the same manner as in [Synthesis Example 106] except that a-43 was used as a reactant. mol)

[합성예 111] 화합물 111 합성[Synthesis Example 111] Synthesis of Compound 111

2,5,8-트리(펜안트렌-9-일)-1,4,7-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성Dihydro-1H-dipyrrolo [2,3-e: 2 ', 3 ' -g ] Synthesis of indole

Figure pat00175
Figure pat00175

반응물로 a-44을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 8.6g(수율 90%)을 얻었다: GC-Mass (이론치: 951.36 g/mol, 측정치: 951 g/mol)
(Theoretical value: 951.36 g / mol, measured value: 951 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-44 was used as a reactant. mol)

[합성예 112] 화합물 112 합성[Synthesis Example 112] Synthesis of Compound 112

2,5,8-트리(나프탈렌-1-일)-1,4,7-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성2,3-e: 2 ', 3'-g] thiophen-2-yl) Synthesis of indole

Figure pat00176
Figure pat00176

반응물로 a-45을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 8.7g(수율 91%)을 얻었다: GC-Mass (이론치: 801.31 g/mol, 측정치: 801 g/mol)
(Theoretical value: 801.31 g / mol, measured value: 801 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-45 was used as a reactant. mol)

[합성예 113] 화합물 113 합성[Synthesis Example 113] Synthesis of Compound 113

1,4,7-트리페닐-2,5,8-트리스(트리페닐렌-2-일)-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성Dihydro-1H-dipyrrolo [2,3-e: 2 ', 3 ' - g] < / RTI >

Figure pat00177
Figure pat00177

반응물로 a-46을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 7.65g(수율 88%)을 얻었다: GC-Mass (이론치: 1101.41 g/mol, 측정치: 1101 g/mol)
(Theoretical value: 1101.41 g / mol, measured value: 1101 g / mol) was obtained in the same manner as in [Synthesis Example 106], except that a-46 was used as a reactant. mol)

[합성예 114] 화합물 114 합성[Synthesis Example 114] Synthesis of Compound 114

1,4,7-트리페닐-2,5,8-트리스(9-페닐-9H-카바졸-3-일)-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성(9-phenyl-9H-carbazol-3-yl) -4,7-dihydro-1H-dipyrrolo [2,3- e: 2 ', 3'-g] indole

Figure pat00178
Figure pat00178

반응물로 a-47을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 7.8g(수율 91%)을 얻었다: GC-Mass (이론치: 1146.44 g/mol, 측정치: 1146 g/mol)
(Theoretical value: 1146.44 g / mol, measured value: 1146 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-47 was used as a reactant. mol)

[합성예 115] 화합물 115 합성[Synthesis Example 115] Synthesis of Compound 115

2,5,8-트리스(디벤조[b,d]푸란-2-일)-1,4,7-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성(Dibenzo [b, d] furan-2-yl) -1,4,7-triphenyl-4,7-dihydro-1H-dipyrrolo [2,3- ', 3'-g] indole

Figure pat00179
Figure pat00179

반응물로 a-48을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 7.88g(수율 92%)을 얻었다: GC-Mass (이론치: 921.30 g/mol, 측정치: 921 g/mol)
(Yield: 92%) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-48 was used as the reactant. GC-Mass (theoretical value: 921.30 g / mol, mol)

[합성예 116] 화합물 116 합성[Synthesis Example 116] Synthesis of Compound 116

1,4,7-트리페닐-2,5,8-트리스(4-(피리딘-3-일)페닐)-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성Dihydro-1H-dipyrrolo [2,3-e: 2 ', 4'-dihydro- 3'-g] indole

Figure pat00180
Figure pat00180

반응물로 a-49를 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 7.96g(수율 86%)을 얻었다: GC-Mass (이론치: 882.35 g/mol, 측정치: 882 g/mol)
(Theoretical value: 882.35 g / mol, measured value: 882 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-49 was used as a reactant. mol)

[합성예 117] 화합물 117 합성[Synthesis Example 117] Synthesis of Compound 117

1,4,7-트리페닐-2,5,8-트리(피리딘-3-일)-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성2,3-e: 2 ', 3 ' -g ' Synthesis of indole

Figure pat00181
Figure pat00181

반응물로 a-50을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 9.4g(수율 90%)을 얻었다: GC-Mass (이론치: 654.25 g/mol, 측정치: 654 g/mol)
(Yield: 90%) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-50 was used as the reactant. GC-Mass (calculated value: 654.25 g / mol, measured value: 654 g / mol)

[합성예 118] 화합물 118 합성[Synthesis Example 118] Synthesis of Compound 118

2,5,8-트리스(4-플루오로페닐)-1,4,7-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성2,3,5-tris (4-fluorophenyl) -1,4,7-triphenyl-4,7-dihydro-1H-dipyrrolo [2,3- Synthesis of indole

Figure pat00182
Figure pat00182

반응물로 a-51을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 9.33g(수율 92%)을 얻었다: GC-Mass (이론치: 705.24 g/mol, 측정치: 705 g/mol)
(Theoretical value: 705.24 g / mol, measured value: 705 g / mol) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that a-51 was used as a reactant. mol)

[합성예 119] 화합물 119 합성[Synthesis Example 119] Synthesis of Compound 119

1,4,7-트리([1,1'-비페닐]-4-일)-2,5,8-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성(1,1'-biphenyl-4-yl) -2,5,8-triphenyl-4,7-dihydro-1H-dipyrrolo [2,3- 2 ', 3'-g] indole

Figure pat00183
Figure pat00183

반응물로 [1,1'-비페닐]-4-아민을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 13.3g(수율 94%)을 얻었다: GC-Mass (이론치: 879.36 g/mol, 측정치: 879 g/mol)
(Yield: 94%) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that [l, r-biphenyl] -4- 879.36 g / mol, measured: 879 g / mol)

[합성예 120] 화합물 120 합성[Synthesis Example 120] Synthesis of Compound 120

1,4,7-트리([1,1'-비페닐]-3-일)-2,5,8-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성(1,1'-biphenyl] -3-yl) -2,5,8-triphenyl-4,7-dihydro-1H-dipyrrolo [2,3- 2 ', 3'-g] indole

Figure pat00184
Figure pat00184

반응물로 [1,1'-비페닐]-3-아민을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 13g(수율 92%)을 얻었다: GC-Mass (이론치: 879.36 g/mol, 측정치: 879 g/mol)
13 g (yield 92%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 106] except that [l, r-biphenyl] -3-amine was used as the reactant: GC-Mass (theoretical value: 879.36 g / mol, measurement: 879 g / mol)

[합성예 121] 화합물 121 합성[Synthesis Example 121] Synthesis of Compound 121

1,4,7-트리(나프탈렌-2-일)-2,5,8-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성2,3-e: 2 ', 3 ' -g ' -trihydro- Synthesis of indole

Figure pat00185
Figure pat00185

반응물로 나프탈렌-2-아민을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 11.6g(수율 90%)을 얻었다: GC-Mass (이론치: 801.31 g/mol, 측정치: 801 g/mol)
(Yield: 90%) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that naphthalene-2-amine was used as the reactant. GC-Mass (theoretical value: 801.31 g / mol, measurement value: 801 g / mol)

[합성예 122] 화합물 122 합성[Synthesis Example 122] Synthesis of Compound 122

1,4-di(iso퀴놀린-6-일)-7-(iso퀴놀린-7-일)-2,5,8-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성1,4-di (isoquinolin-6-yl) -7- (isoquinolin-7-yl) -2,5,8-triphenyl-4,7-dihydro- e: Synthesis of 2 ', 3'-g] indole

Figure pat00186
Figure pat00186

반응물로 iso퀴놀린-7-아민을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 10.9g(수율 84%)을 얻었다: GC-Mass (이론치: 804.30 g/mol, 측정치: 804 g/mol)
(Yield: 84%) was obtained by carrying out the same procedure as in [Synthesis Example 106], except that isoquinolin-7-amine was used as the reactant. GC-Mass (theoretical value: 804.30 g / mol, 804 g / mol)

[합성예 123] 화합물 123 합성[Synthesis Example 123] Synthesis of Compound 123

2,5,8-트리페닐-1,4,7-트리스(9-페닐-9H-카바졸-3-일)-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성(9-phenyl-9H-carbazol-3-yl) -4,7-dihydro-1H-dipyrrolo [2,3- e: 2 ', 3'-g] indole

Figure pat00187
Figure pat00187

반응물로 9-페닐-9H-카바졸-3-아민을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 15.2g(수율82%)을 얻었다: GC-Mass (이론치: 1146.44 g/mol, 측정치: 147 g/mol)
(Yield: 82%) was obtained by following the same procedure as in Synthesis Example 106 except that 9-phenyl-9H-carbazol-3-amine was used as the reactant. GC-Mass (calcd .: 1146.44 g / mol, measurement: 147 g / mol)

[합성예 124] 화합물 124 합성[Synthesis Example 124] Synthesis of Compound 124

1,4,7-트리스(9,9-di메틸-9H-플루오렌-3-일)-2,5,8-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성1,4,7-tris (9,9-di methyl-9H-fluoren-3-yl) -2,5,8-triphenyl-4,7- dihydro- lH- dipyrrolo [2,3- e: Synthesis of 2 ', 3'-g] indole

Figure pat00188
Figure pat00188

반응물로 9,9-di메틸-9H-플루오렌-3-아민을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 13.26g(수율 82%)을 얻었다: GC-Mass (이론치: 1000.28 g/mol, 측정치: 1000 g/mol)
13.26 g (yield 82%) of the desired compound was obtained by carrying out the same procedure as in [Synthesis Example 106] except that 9,9-di methyl-9H-fluorene- Theoretical value: 1000.28 g / mol, measured: 1000 g / mol)

[합성예 125] 화합물 125 합성[Synthesis Example 125] Synthesis of Compound 125

1,4,7-트리스(4-플루오로페닐)-2,5,8-트리페닐-4,7-디하이드로-1H-디피롤로[2,3-e:2',3'-g]인돌의 합성2,3-e: 2 ', 3'-g] thiophene-1, Synthesis of indole

Figure pat00189
Figure pat00189

반응물로 4-플루오로아닐린을 사용한 것을 제외하고는 [합성예 106]과 동일한 과정을 수행하여 목적 화합물 10.67g(수율 88%)을 얻었다: GC-Mass (이론치: 750.24 g/mol, 측정치: 750 g/mol)
(Yield: 88%) was obtained by carrying out the same procedure as in [Synthesis Example 106] except that 4-fluoroaniline was used as the reactant. GC-Mass (calcd. 750.24 g / mol, measurement: 750 g / mol)

[실시예 1] 청색 유기 전계 발광 소자의 제조[Example 1] Production of blue organic electroluminescent device

합성예에서 합성된 화합물을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 청색 유기 전계 발광 소자를 제조하였다.The compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a blue organic electroluminescent device was produced as follows.

ITO (Indium tin oxide)가 1500 Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 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.Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. 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 the substrate was transferred to a vacuum evaporator.

상기와 같이 준비된 ITO 투명 전극 위에, DS-205 (80 nm)/NPB (15 nm)/ADN + 5 % DS-405 (30nm)/합성예 1의 화합물(30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제조하였다.(30 nm) / LiF (1 nm) / LiF (15 nm) / ADN + 5% DS-405 (30 nm) / Synthesis Example 1 on the ITO transparent electrode prepared as above. Al (200 nm) were stacked in this order to fabricate an organic electroluminescent device.

이때 사용된 NPB, ADN 및 Alq3의 구조는 다음과 같다.The structures of NPB, ADN and Alq 3 used in this case are as follows.

Figure pat00190

Figure pat00190

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

수명 개선층을 포함하지 않고, 전자 수송층 물질인 Alq3을 30nm로 증착하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 청색 유기 전계 발광 소자를 제작하였다.
A blue organic electroluminescent device was fabricated in the same manner as in Example 1, except that the lifetime improving layer was not included and the electron transport layer material Alq 3 was deposited at 30 nm.

[평가예 1][Evaluation Example 1]

실시예 1 내지 62 및 비교예 1에서 각각 제조된 유기 전계 발광 소자에 대하여, 전류밀도 10 mA/㎠에서의 구동전압, 전류효율, 발광파장을 측정하였고, 그 결과를 하기 표 1에 나타내었다.
The driving voltage, current efficiency and emission wavelength at the current density of 10 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 1 to 62 and Comparative Example 1, respectively, and the results are shown in Table 1 below.

샘플Sample 전자수송층Electron transport layer 구동전압
(V)Driving voltage
(V) 전류효율
(cd/A)Current efficiency
(cd / A) 발광피크
(nm)Emission peak
(nm) 실시예1Example 1 1One 4.04.0 5.95.9 458458 실시예2Example 2 22 4.24.2 5.85.8 458458 실시예3Example 3 33 4.34.3 5.95.9 459459 실시예4Example 4 44 4.14.1 5.85.8 458458 실시예5Example 5 55 4.54.5 5.95.9 458458 실시예6Example 6 66 4.04.0 6.06.0 458458 실시예7Example 7 77 4.14.1 6.06.0 458458 실시예8Example 8 88 4.14.1 6.16.1 459459 실시예9Example 9 99 4.24.2 5.85.8 457457 실시예10Example 10 1010 4.64.6 5.85.8 458458 실시예11Example 11 1111 4.54.5 5.95.9 458458 실시예12Example 12 1212 4.44.4 5.95.9 458458 실시예13Example 13 1313 4.14.1 5.75.7 458458 실시예14Example 14 1414 4.14.1 5.95.9 459459 실시예15Example 15 1515 4.04.0 5.95.9 458458 실시예16Example 16 1616 4.24.2 6.06.0 458458 실시예17Example 17 1717 4.34.3 6.06.0 458458 실시예18Example 18 1818 4.14.1 6.16.1 458458 실시예19Example 19 1919 4.54.5 5.85.8 459459 실시예20Example 20 2020 4.04.0 5.85.8 458458 실시예21Example 21 2121 4.24.2 5.95.9 458458 실시예22Example 22 2222 4.34.3 5.95.9 459459 실시예23Example 23 2323 4.14.1 5.95.9 458458 실시예24Example 24 2424 4.54.5 5.85.8 458458 실시예25Example 25 2525 4.04.0 5.95.9 458458 실시예26Example 26 2626 4.34.3 6.06.0 458458 실시예27Example 27 2727 4.54.5 6.06.0 459459 실시예28Example 28 2828 4.44.4 6.16.1 457457 실시예29Example 29 2929 4.14.1 5.85.8 458458 실시예30Example 30 3030 4.14.1 5.85.8 458458 실시예31Example 31 3131 4.04.0 5.95.9 458458 실시예32Example 32 3232 4.14.1 5.95.9 458458 실시예33Example 33 3333 4.34.3 5.75.7 458458 실시예34Example 34 5252 4.34.3 5.95.9 458458 실시예35Example 35 5454 4.24.2 5.85.8 458458 실시예36Example 36 5555 4.04.0 5.95.9 459459 실시예37Example 37 5656 4.24.2 6.06.0 458458 실시예38Example 38 5959 4.34.3 5.95.9 458458 실시예39Example 39 6060 4.14.1 6.06.0 458458 실시예40Example 40 6161 4.54.5 6.06.0 458458 실시예41Example 41 6363 4.04.0 6.16.1 458458 실시예42Example 42 6464 4.04.0 5.85.8 459459 실시예43Example 43 6565 4.24.2 5.85.8 458458 실시예44Example 44 6666 4.34.3 5.95.9 458458 실시예45Example 45 6767 4.14.1 5.95.9 458458 실시예46Example 46 7070 4.54.5 5.75.7 458458 실시예47Example 47 7171 4.04.0 5.95.9 459459 실시예48Example 48 7272 4.14.1 5.85.8 457457 실시예49Example 49 7373 4.14.1 5.95.9 458458 실시예50Example 50 7575 4.24.2 6.06.0 458458 실시예51Example 51 7676 4.14.1 6.16.1 458458 실시예52Example 52 7777 4.14.1 5.85.8 459459 실시예53Example 53 7878 4.04.0 5.85.8 457457 실시예54Example 54 7979 4.14.1 5.95.9 458458 실시예55Example 55 8080 4.24.2 5.95.9 458458 실시예56Example 56 8282 4.44.4 5.75.7 458458 실시예57Example 57 8383 4.44.4 5.95.9 458458 실시예58Example 58 8484 4.54.5 5.85.8 459459 실시예59Example 59 8888 4.24.2 5.95.9 458458 실시예60Example 60 9090 4.14.1 5.95.9 458458 실시예61Example 61 100100 4.54.5 5.95.9 457457 실시예62Example 62 101101 4.24.2 5.75.7 458458 비교예 1Comparative Example 1 AlqAlq 4.7 4.7 5.6 5.6 458 458

[실시예 63 ~102] 유기 EL 소자의 제조[Examples 63 to 102] Preparation of organic EL device

ITO (Indium tin oxide)가 1500 두께로 박막 코팅된 유리 기판을 증류수 초음파로 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 5 분간 세정한 후 진공 층착기로 기판을 이송하였다. Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 was washed with distilled water ultrasonic wave. After the distilled water was washed, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, and dried. Then, the substrate was transferred to a UV OZONE cleaner (Power Sonic 405, Hoshin Tech) The substrate was transferred to a vacuum deposition machine.

상기와 같이 준비된 ITO 투명 전극 위에 정공 주입층 재료로써, 합성예의 화합물(60nm)/NPB (80nm)/DS-H522 + 5% DS-501(30nm)/BCP(10nm)/Alq3(30 nm)/LiF(1nm)/Al(200nm) 순서로 유기 EL 소자를 제조하였다. (60 nm) / NPB (80 nm) / DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 (30 nm) / An organic EL device was fabricated in the order of LiF (1 nm) / Al (200 nm).

소자 제작에 사용된 DS-H522 와 DS-501 은 ㈜ 두산 전자 BG 제품이며, m-MTDATA, TCTA, CBP, Ir(ppy)3, 및 BCP의 구조는 아래와 같다.
The structures of m-MTDATA, TCTA, CBP, Ir (ppy) 3 and BCP are as follows. DS-H522 and DS-

Figure pat00191
Figure pat00191

Figure pat00192
Figure pat00192

[비교예 2] 유기 EL 소자의 제작[Comparative Example 2] Fabrication of organic EL device

정공 주입층 형성시 합성예에서 제조된 화합물 대신 상기 m-MTDATA(60nm)를 정공 주입층 물질로 사용한 것을 제외하고는, 상기 실시예 1과 동일한 방법으로 유기 EL 소자를 제조하였다.An organic EL device was prepared in the same manner as in Example 1, except that m-MTDATA (60 nm) was used as the hole injection layer material in place of the compound prepared in Synthesis Example in forming the hole injection layer.

[실험예][Experimental Example]

실시예 63-102 및 비교예 1에서 제작한 각각의 유기 EL 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율를 측정하고 그 결과를 하기 표 2에 나타내었다.The driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured for each of the organic EL devices manufactured in Examples 63-102 and Comparative Example 1, and the results are shown in Table 2 below.

샘플Sample 정공주입층Hole injection layer 구동 전압Driving voltage 전류효율Current efficiency (V)(V) (cd/A)(cd / A) 실시예63Example 63 1212 4.94.9 19.519.5 실시예64Example 64 1515 4.84.8 19.719.7 실시예65Example 65 1717 4.94.9 20.020.0 실시예66Example 66 3333 4.94.9 19.019.0 실시예67Example 67 3434 4.94.9 19.019.0 실시예68Example 68 3535 4.94.9 19.819.8 실시예69Example 69 3636 4.94.9 20.420.4 실시예70Example 70 3737 4.84.8 20.520.5 실시예71Example 71 3838 4.94.9 19.719.7 실시예72Example 72 3939 5.05.0 20.020.0 실시예73Example 73 4040 4.94.9 19.019.0 실시예74Example 74 4141 4.84.8 19.019.0 실시예75Example 75 4242 4.94.9 19.819.8 실시예76Example 76 4343 4.84.8 20.420.4 실시예77Example 77 4444 4.94.9 20.520.5 실시예78Example 78 4545 4.94.9 19.719.7 실시예79Example 79 4646 4.94.9 20.020.0 실시예80Example 80 4747 4.94.9 19.019.0 실시예81Example 81 4848 4.94.9 19.019.0 실시예82Example 82 4949 4.84.8 19.819.8 실시예83Example 83 5050 4.94.9 20.420.4 실시예84Example 84 5151 5.05.0 20.520.5 실시예85Example 85 5353 4.94.9 19.719.7 실시예86Example 86 5858 4.84.8 20.020.0 실시예87Example 87 6262 4.94.9 19.019.0 실시예88Example 88 6868 4.84.8 19.019.0 실시예89Example 89 6969 4.94.9 19.819.8 실시예90Example 90 7474 4.94.9 20.420.4 실시예91Example 91 8181 4.84.8 20.520.5 실시예92Example 92 8585 4.94.9 19.719.7 실시예93Example 93 8686 4.94.9 20.020.0 실시예94Example 94 8787 4.94.9 19.019.0 실시예95Example 95 9292 4.94.9 20.420.4 실시예96Example 96 9999 4.94.9 20.520.5 실시예97Example 97 103103 4.84.8 19.719.7 실시예98Example 98 104104 4.94.9 20.020.0 실시예99Example 99 105105 5.05.0 20.420.4 실시예100Example 100 118118 4.94.9 20.520.5 실시예101Example 101 112112 4.84.8 20.220.2 실시예102Example 102 125125 4.94.9 20.120.1 비교예 2Comparative Example 2 m-MTDATAm-MTDATA 5.25.2 18.118.1

상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물(12 ~ 125)을 정공주입층으로 사용하였을 경우(실시예 63-102) 종래 m-MTDATA(60nm)를 사용한 EL 소자(비교예2)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2, when the compound (12 to 125) according to the present invention was used as the hole injecting layer (Examples 63 to 102), the EL device (Comparative Example 2) using conventional m-MTDATA In comparison, it can be seen that performance is better in terms of efficiency and driving voltage.

[실시예 103 ~ 149 ] 녹색 유기 EL 소자의 제작[Examples 103 to 149] Fabrication of green organic EL device

합성예 1-125에서 합성한 화합물 1 ~ 125을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 EL 소자를 제작하였다.Compounds 1 to 125 synthesized in Synthesis Example 1-125 were subjected to high purity sublimation purification by a conventionally known method, and a green organic EL device was fabricated according to the following procedure.

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

이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 1 ~ 125의 각각의 화합물 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 EL 소자를 제작하였다. Each compound of m-MTDATA (60 nm) / TCTA (80 nm) / 1 to 125 + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) / Alq 3 ) / LiF (1 nm) / Al (200 nm) were stacked in this order to fabricate an organic EL device.

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

Figure pat00193
Figure pat00193

Figure pat00194
Figure pat00194

[비교예 3] 녹색 유기 EL 소자의 제작[Comparative Example 3] Production of green organic EL device

발광층 형성시 발광 호스트 물질로서 화합물 1 대신 CBP를 사용하는 것을 제외하고는 실시예 103과 동일한 과정으로 녹색 유기 EL 소자를 제작하였다.
A green organic EL device was fabricated in the same manner as in Example 103, except that CBP was used instead of Compound 1 as a luminescent host material in forming the light emitting layer.

[평가예][Evaluation example]

실시예 103-149 및 비교예 3에서 제작한 각각의 녹색 유기 EL 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 3에 나타내었다.
The driving voltage, current efficiency and emission peak at the current density (10) mA / cm < 2 > were measured for each of the green organic EL devices manufactured in Examples 103-149 and Comparative Example 3, .

샘플Sample 호스트Host 구동 전압
(V)Driving voltage
(V) EL 피크
(nm)EL peak
(nm) 전류효율
(cd/A)Current efficiency
(cd / A) 실시예103Example 103 1One 6.486.48 515515 40.040.0 실시예104Example 104 33 6.866.86 518518 41.841.8 실시예105Example 105 99 6.616.61 517517 44.244.2 실시예106Example 106 1111 6.516.51 515515 41.741.7 실시예107Example 107 1818 6.776.77 518518 41.541.5 실시예108Example 108 2020 6.466.46 515515 43.943.9 실시예109Example 109 2121 6.716.71 518518 41.041.0 실시예110Example 110 2323 6.766.76 517517 43.443.4 실시예111Example 111 2424 6.576.57 515515 44.144.1 실시예112Example 112 2626 6.866.86 518518 41.441.4 실시예113Example 113 Synthesis of 2828 6.616.61 515515 42.242.2 실시예114Example 114 2929 6.816.81 518518 43.143.1 실시예115Example 115 3030 6.746.74 515515 41.141.1 실시예116Example 116 7171 6.466.46 518518 42.042.0 실시예117Example 117 7272 6.716.71 515515 42.542.5 실시예118Example 118 7575 6.796.79 518518 41.341.3 실시예119Example 119 7676 6.556.55 518518 41.941.9 실시예120Example 120 7777 6.686.68 516516 43.043.0 실시예121Example 121 7878 6.716.71 515515 40.740.7 실시예122Example 122 7979 6.636.63 518518 41.341.3 실시예123Example 123 8080 6.816.81 517517 41.541.5 실시예124Example 124 8484 6.766.76 515515 41.141.1 실시예125Example 125 8888 6.836.83 518518 42.542.5 실시예126Example 126 8989 6.816.81 517517 43.143.1 실시예127Example 127 9090 6.766.76 515515 39.239.2 실시예128Example 128 9393 6.486.48 518518 41.341.3 실시예129Example 129 9494 6.866.86 515515 42.942.9 실시예130Example 130 9595 6.796.79 518518 39.639.6 실시예131Example 131 9696 6.876.87 515515 40.940.9 실시예132Example 132 9797 6.876.87 515515 40.940.9 실시예133Example 133 9898 6.796.79 518518 41.641.6 실시예134Example 134 102102 6.796.79 518518 41.641.6 실시예135Example 135 106106 6.796.79 518518 41.641.6 실시예136Example 136 107107 6.816.81 517517 43.143.1 실시예137Example 137 108108 6.766.76 515515 39.239.2 실시예138Example 138 109109 6.486.48 518518 41.341.3 실시예139Example 139 111111 6.866.86 515515 42.942.9 실시예140Example 140 112112 6.796.79 518518 39.639.6 실시예141Example 141 113113 6.876.87 515515 40.940.9 실시예142Example 142 [ 114114 6.876.87 515515 40.940.9 실시예143Example 143 115115 6.796.79 518518 41.641.6 실시예144Example 144 116116 6.796.79 518518 41.641.6 실시예145Example 145 119119 6.796.79 518518 41.641.6 실시예146Example 146 120120 6.796.79 518518 41.641.6 실시예147Example 147 121121 6.796.79 518518 41.641.6 실시예148Example 148 123123 6.796.79 518518 41.641.6 실시예149Example 149 124124 6.796.79 518518 41.641.6 비교예 3Comparative Example 3 CBPCBP 6.936.93 516516 38.238.2

상기 표3에 나타낸 바와 같이, 본 발명에 따른 화합물(1 ~ 125)을 녹색 유기 EL 소자의 발광층으로 사용하였을 경우(실시예 103-149) 종래 CBP를 사용한 녹색 유기 EL 소자(비교예3)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 3, when the compound (1 to 125) according to the present invention was used as a light emitting layer of a green organic EL device (Examples 103 to 149), a green organic EL device (Comparative Example 3) In comparison, it can be seen that performance is better in terms of efficiency and driving voltage.

[실시예 150 ~ 174] 전하 수송성 평가 소자의 제작[Examples 150 to 174] Preparation of charge transportability evaluation element

상기에서 얻은 합성예 1-125에서 합성한 화합물 1 ~ 125을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 화합물 (10 ㎎), 톨루엔 (1000 ㎕) 을 혼합한 도포 용액을 조제하였다.Compounds 1 to 125 synthesized in Synthesis Example 1-125 thus obtained were subjected to high purity sublimation purification by a conventionally known method, and a coating solution in which a compound (10 mg) and toluene (1000 μl) were mixed was prepared.

먼저 ITO 를 1.6 ㎜ 폭으로 패터닝한 유리 기판 상에 이 도포 용액을 3000 min-1로 스핀 코트하고, 박막을 형성하여 정공 주입층 (30 ㎚) 을 형성하였다. 여기까지는, 대기 하에서 실시하였다. 얻어진 유리 기판을 진공 증착기 중으로 옮기고, 상기 정공 주입층 상에 NPB (80 ㎚)/(DS-H522+5% DS-501 (30 ㎚)/BCP (10 ㎚)/ Alq3 (30 ㎚)/LiF (막두께 1 ㎚)/Al (막두께 200 ㎚)의 순서로 증착하였다. 전극 형성 후, 대기 개방하지 않고, 건조 질소 환경 중으로 유리 기판을 이동하였다. 두께 0.7 ㎜ 의 무알칼리 유리에 깊이 0.4 ㎜ 의 스폿 페이싱을 형성한 밀봉 유리와 유리 기판을 광 경화성 에폭시 수지를 사용하여 첩합함으로써 밀봉을 실시하고, 다층 구조의 유기 EL 소자를 제조하였다. 이후의 실험은 대기 중, 실온 (25℃) 에서 실시하였다. First, this coating solution was spin-coated on a glass substrate patterned with a width of 1.6 mm of ITO at 3000 min -1 to form a thin film to form a hole injection layer (30 nm). Up to this point, it was carried out under the atmosphere. The resultant glass substrate was transferred into a vacuum evaporator and NPB (80 nm) / (DS-H522 + 5% DS-501 (30 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (Thickness: 1 nm) / Al (film thickness: 200 nm) were deposited in this order on a glass substrate having a thickness of 0.7 mm, and then the glass substrate was moved into a dry nitrogen atmosphere Sealing was performed by bonding the sealing glass having the spot facings formed thereon and the glass substrate using a photocurable epoxy resin to prepare a multilayered organic EL device. The subsequent experiments were carried out in the air at room temperature (25 DEG C) .

소자 제작에 사용된 DS-H522 와 DS-501 은 ㈜ 두산 전자 BG 제품이며 PEDOT.PSS, αNPD, Ir(ppy)3, CBP, BAlq 및Alq3 의 구조는 아래와 같다.
The structures of PEDOT.PSS, αNPD, Ir (ppy) 3 , CBP, BAlq and Alq3 are as follows. DS-H522 and DS-

Figure pat00195
Figure pat00196
Figure pat00195
Figure pat00196

PEDOT.PSSPEDOT.PSS

Figure pat00197

Figure pat00197

[비교예 4] 녹색 유기 EL 소자의 제작[Comparative Example 4] Production of green organic EL device

ITO 를 1.6 ㎜ 폭으로 패터닝한 유리 기판 상에, PEDOT：PSS분산액(스타르크ㅇ브이테크사 제조, AI4083LVW142)을 1500 min-1로 스핀 코팅 하여 정공 주입층 (40 ㎚) 을 형성하였다. 그 후, 실시예 150 과 동일한 방법으로 다층 구조의 유기 EL 소자를 제조하였다.
A hole injection layer (40 nm) was formed by spin coating a PEDOT: PSS dispersion (AI4083LVW142, manufactured by Stark Co., Ltd.) at 1500 min -1 onto a glass substrate having ITO patterned with a width of 1.6 mm. Thereafter, an organic EL device having a multilayer structure was produced in the same manner as in Example 150. [

[평가예][Evaluation example]

실시예 78-111 및 비교예 4에서 제작한 각각의 녹색 유기 EL 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 4에 나타내었다.
The driving voltage, current efficiency and emission peak at the current density (10) mA / cm 2 were measured for each of the green organic EL devices manufactured in Examples 78-111 and Comparative Example 4, and the results are shown in Table 4 .

샘플Sample 정공주입층Hole injection layer 구동 전압Driving voltage 전류효율Current efficiency (V)(V) (cd/A)(cd / A) 실시예150Example 150 3434 5.05.0 19.519.5 실시예151Example 151 3535 4.94.9 19.719.7 실시예152Example 152 3636 4.84.8 19.519.5 실시예153Example 153 3838 4.94.9 19.719.7 실시예154Example 154 3939 4.84.8 20.020.0 실시예155Example 155 4242 4.94.9 19.019.0 실시예156Example 156 4444 4.94.9 19.019.0 실시예157Example 157 4545 4.94.9 19.819.8 실시예158Example 158 4646 4.94.9 20.420.4 실시예159Example 159 4747 4.94.9 20.520.5 실시예160Example 160 4848 4.84.8 19.719.7 실시예161Example 161 4949 4.94.9 20.020.0 실시예162Example 162 5050 5.05.0 19.019.0 실시예163Example 163 5151 4.94.9 19.019.0 실시예164Example 164 5757 5.05.0 19.819.8 실시예165Example 165 5858 4.94.9 19.719.7 실시예166Example 166 6262 4.84.8 20.020.0 실시예167Example 167 6868 4.94.9 19.519.5 실시예168Example 168 6969 4.84.8 19.719.7 실시예169Example 169 8585 4.94.9 20.020.0 실시예170Example 170 8686 4.94.9 19.019.0 실시예171Example 171 8787 4.94.9 19.019.0 실시예172Example 172 103103 4.94.9 19.819.8 실시예173Example 173 104104 4.94.9 20.420.4 실시예174Example 174 105105 5.05.0 19.019.0 비교예 4Comparative Example 4 PEDOT：PSSPEDOT: PSS 5.25.2 18.118.1

이상으로 실시예를 이용하여 본 발명의 실시형태의 효과를 나타내었다. 본 발명의 실시형태인 합성예의 화합물의 도포용액은, 용이하게 조제할 수 있기 때문에, 이것을 사용함으로써 유기층을 용이하게 다층화할 수 있다. 본 발명의 실시형태인 화합물의 도포용액을 사용함으로써, 종래 PEDOT.PSS의 도포용액을 사용한 EL 소자(비교예4)와 비교해 볼 때 유기 일렉트로닉스 소자의 구동 전압을 저감시킬 수 있고, 발광 효율, 전력 효율, 또는 수명 등을 높일 수 있다.The effects of the embodiment of the present invention are shown above using the examples. Since the coating solution of the compound of the synthesis example of the embodiment of the present invention can be easily prepared, it is possible to easily make the organic layer multilayered by using it. By using the coating solution of the compound of the embodiment of the present invention, it is possible to reduce the driving voltage of the organic electronic device compared with the EL device (Comparative Example 4) using the conventional PEDOT.PSS coating solution, Efficiency, or service life of the device.

Claims (10)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure pat00198

상기 화학식 1에서,
X1 은 N 또는 C(R4)이고,
Y1 내지 Y3은 각각 독립적으로 O, S, N(Ar1) 및 C(Ar2)(Ar3)로 이루어진 군으로부터 선택되고,
R1 내지 R4는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 알킬포스핀기, C1~C60의 알킬포스피닐기 C6~C60의 아릴포스핀기, C6~C60의 아릴포스피닐기 및 C1~C60의 아민기로 이루어진 군으로부터 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있고,
Ar1 내지 Ar3는 서로 동일하거나 상이하며, 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군으로부터 선택되고,
상기 Ar1 내지 Ar3 및 R1 내지 R4의 알킬기, 알케닐기, 알키닐기. 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 알킬포스핀기, 아릴포스핀기, 알킬포스피닐기, 아릴포스피닐기 및 아민기는 각각 독립적으로, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C1~C60의 알킬포스핀기, C1~C60의 알킬포스피닐기, C6~C60의 아릴포스핀기, C6~C60의 아릴포스피닐기 및 C1~C60의 아민기로 이루어진 군으로부터 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있으며,
Ar1 내지 Ar3 및 R1 내지 R4가 복수개의 치환기로 치환될 경우, 복수개의 치환기는 서로 동일하거나 상이할 수 있고,
단, X1 이 C(R4)인 경우, Y1 내지 Y3 이 모두 C(Ar2)(Ar3)는 아니다.A compound represented by the following formula (1):
[Chemical Formula 1]
Figure pat00198

In Formula 1,
X 1 is N or C (R 4 )
Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (Ar 1 ) and C (Ar 2 ) (Ar 3 )
R 1 to R 4 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ of C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ~ alkyloxy group of C 40, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkyl silyl group, C 6 ~ C aryl silyl group of 60, C 1 ~ C 40 group of an alkyl boron, an aryl boronic of C 6 ~ C 60, C 1 ~ alkylphosphonate of C 60 pingi, C selected from 1 ~ C 60 alkyl phosphonic blood group C 6 ~ C 60 aryl phosphine pingi, aryl Phosphinicosuccinic group and a C 1 ~ the group consisting of C 60 amines of C 6 ~ C 60 of Or may combine with adjacent groups to form a condensed ring,
Ar 1 to Ar 3 are the same or different and each independently represents a C 1 to C 40 alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 3 to C 40 cycloalkyl group, A cycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryloxy group , A C 3 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, a C 1 to C 40 alkylboron group, a C 6 to C 60 arylboron group, a C 6 to C 60 arylphosphine group is selected from aryl phosphonic blood group and C 6 ~ C 60 aryl group consisting of an amine group of a C 6 ~ C 60,
An alkyl group, an alkenyl group or an alkynyl group of the above Ar 1 to Ar 3 and R 1 to R 4 . An aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an alkyl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, an aryl group, , The arylphosphinyl group and the amine group are each independently selected from the group consisting of halogen, cyano group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cyclo An alkyl group having 3 to 40 nuclear atoms, a heterocycloalkyl group having 3 to 40 nuclear atoms, an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 5 to 60 nuclear atoms, a C 1 to C 40 alkyloxy group, a C 6 to C 60 aryl An aryloxy group of C 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkylboron group of C 1 to C 40 , an arylboron group of C 6 to C 60 , a C 1 to C 60 alkyl phosphine group, at least one member selected from the C 1 ~ C 60 alkyl phosphonic blood group, C 6 ~ C 60 aryl phosphine group, an aryl Phosphinicosuccinic group and a C 1 ~ the group consisting of C 60 amines of C 6 ~ C 60 of Tooth Groups may be unsubstituted or substituted,
When Ar 1 to Ar 3 and R 1 to R 4 are substituted with a plurality of substituents, the plurality of substituents may be the same or different from each other,
However, when X 1 is C (R 4 ), all of Y 1 to Y 3 are not C (Ar 2 ) (Ar 3 ). 제1항에 있어서, 상기 화학식 1로 표시되는 화합물이 하기 화학식 1-A 내지 화학식 1-G로 나타내어지는 화합물들로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물:
Figure pat00199

상기 화학식 1-A 내지 화학식 1-G에서 Ar1 내지 Ar3 및 R1 내지 R4는 화학식 1에서 정의한 바와 같다.The compound according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of compounds represented by the following formulas (1-A) to (1-G)
Figure pat00199

Ar 1 to Ar 3 and R 1 to R 4 in the general formulas (1-A) to (1-G) are as defined in the general formula (1). 제 1항에 있어서, R1 내지 R4는 각각 독립적으로 수소, 할로겐, 시아노기, C1~C40의 알킬기, C6~C60의 아릴기, 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물.The compound according to claim 1, wherein each of R 1 to R 4 independently represents a hydrogen atom, a halogen atom, a cyano group, a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms ≪ / RTI > 제 1항에 있어서, Ar1 내지 Ar3는 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물.The compound according to Claim 1, wherein each of Ar 1 to Ar 3 is independently selected from the group consisting of a C 1 to C 40 alkyl group, a C 6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms . 제 4항에 있어서, 상기 C6~C60의 아릴기 및 핵원자수 5 내지 60개의 헤테로아릴기가 각각 독립적으로 할로겐, 시아노기 및 C6~C60의 아릴포스핀기로 이루어진 군으로부터 선택된 하나 이상의 치환기로 추가로 치환되는 것을 특징으로 하는 화합물.Of claim 4, wherein the C 6 ~ C 60 aryl group and the number of nuclear atoms of 5 to 60 heteroaryl group, each independently represent a halogen, a cyano group and a C 6 ~ at least one group selected from an aryl phosphine group consisting pin group for C 60 Lt; / RTI > is further substituted as a substituent. 제 1항에 있어서, 상기 화합물이 아래의 화합물로 이루어진 군으로부터 선택되는 것을 특징으로 하는 화합물:
Figure pat00200
Figure pat00201

Figure pat00202

Figure pat00203

Figure pat00204

Figure pat00205

Figure pat00206

Figure pat00207
2. A compound according to claim 1, wherein said compound is selected from the group consisting of:
Figure pat00200
Figure pat00201

Figure pat00202

Figure pat00203

Figure pat00204

Figure pat00205

Figure pat00206

Figure pat00207
 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 제1항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 유기 전계 발광 소자.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 the compound according to any one of claims 1 to 6. 제7항에 있어서,
상기 화합물을 포함하는 유기물층이 전자 수송층 및 전자 주입층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.8. The method of claim 7,
Wherein the organic compound layer containing the compound is selected from the group consisting of an electron transport layer and an electron injection layer. 제7항에 있어서,
상기 화합물을 포함하는 유기물층이 정공 주입층인 유기 전계 발광 소자.8. The method of claim 7,
Wherein the organic compound layer containing the compound is a hole injection layer. 제7항에 있어서,
상기 화합물을 포함하는 유기물층이 발광층인 유기 전계 발광 소자.8. The method of claim 7,
Wherein the organic compound layer containing the compound is a light emitting layer.
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