KR20120116881A - Condensed aryl compound and organic light-diode including the same - Google Patents

Condensed aryl compound and organic light-diode including the same Download PDF

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KR20120116881A
KR20120116881A KR1020120038093A KR20120038093A KR20120116881A KR 20120116881 A KR20120116881 A KR 20120116881A KR 1020120038093 A KR1020120038093 A KR 1020120038093A KR 20120038093 A KR20120038093 A KR 20120038093A KR 20120116881 A KR20120116881 A KR 20120116881A
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제종태
최성근
김남이
김희대
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에스에프씨 주식회사
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Abstract

PURPOSE: A fused aryl compound is provided to provide an organic electroluminescence device with low driving voltage and improved luminous efficiency because of stable and excellent luminous properties relative with existing materials. CONSTITUTION: A fused aryl compound is represented by chemical formula 1. In chemical formula 1, X is O, S, P, NR5, CR5R6 or SiR5R6, and each of R1-R6, A1, A2, B1 and B2 is selected from hydrogen, deuterium, substituted or unsubstituted C1-30 alkyl, substituted or unsubstituted C2-30 alkenyl, substituted or unsubstituted C3-30 cycloalkyl, substituted or unsubstituted C5-30 cycloalkenyl, substituted or unsubstituted C1-30 alkoxy, substituted or unsubstituted C6-30 arloxy, substituted or unsubstituted C1-30 alkylthioxy, substituted or unsubstitutedC5-30 arytioxy, substituted or unsubstituted C1-30 alkylamine, substituted or unsubstituted C5-30 arylamine, substituted or unsubstituted C5-50 aryl, C3-50 heteroaryl, substituted or unsubstituted silicon, substituted or unsubstituted boron, substituted or unsubstituted silane, carbonyl, phosphoryl, amino, nitrile, hydroxy, nitro, halogen, amide and ester.

Description

축합아릴 화합물 및 이를 포함하는 유기전계발광소자{Condensed aryl compound and organic light-diode including the same}Condensed aryl compound and organic light-diode including the same}

본 발명은 신규한 축합아릴 화합물 및 이를 발광물질로 포함하는 유기전계발광소자에 관한 것으로서, 보다 상세하게는 구동전압, 전류효율 등의 발광 특성이 우수하고, 보다 안정적인 신규한 축합아릴 화합물 및 이를 포함하는 유기전계발광소자에 관한 것이다.The present invention relates to a novel condensed aryl compound and an organic light emitting device comprising the same as a light emitting material, and more particularly, a new condensed aryl compound having excellent luminescent properties such as driving voltage and current efficiency, and more stable. It relates to an organic electroluminescent device.

최근 표시장치의 대형화에 따라 공간 점유가 작은 평면표시소자의 요구가 증대되고 있는데, 대표적인 평면표시소자인 액정 디스플레이는 기존의 CRT(cathode ray tube)에 비해 경량화가 가능하다는 장점은 있으나, 시야각(viewing angle)이 제한되고 배면 광(back light)이 반드시 필요하다는 등의 단점을 갖고 있다. 이에 반하여, 새로운 평면표시소자인 유기전계발광소자(organic light emitting diode, OLED)는 자기 발광 현상을 이용한 디스플레이로서, 시야각이 크고, 액정 디스플레이에 비해 경박, 단소해질 수 있으며, 빠른 응답 속도 등의 장점을 가지고 있으며, 최근에는 풀-컬러(full-color) 디스플레이 또는 조명으로의 응용이 기대되고 있다.Recently, as the size of the display device increases, the demand for a flat display device having a small space is increasing. A liquid crystal display, which is a typical flat display device, has a merit of being lighter than a conventional cathode ray tube (CRT). The disadvantage is that the angle is limited and the back light is necessary. In contrast, organic light emitting diodes (OLEDs), which are new flat panel display devices, are displays using self-luminous phenomena, and have a large viewing angle, are thinner and shorter than liquid crystal displays, and have fast response speeds. In recent years, the application to full-color display or lighting is expected.

일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다.In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

유기 발광 현상을 이용하는 유기전계발광소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전계발광소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어질 수 있다. 이러한 유기전계발광소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 이러한 유기전계발광소자는 자발광, 고휘도, 고효율, 낮은 구동전압, 넓은 시야각, 높은 콘트라스트, 고속 응답성 등의 특성을 갖는 것으로 알려져 있다.An organic light emitting display device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows. Such an organic electroluminescent device is known to have properties such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.

유기전계발광소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.The material used as the organic material layer in the organic electroluminescent device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting material may be classified into a polymer type and a low molecular type according to molecular weight, and may be classified into a fluorescent material derived from a singlet excited state of electrons and a phosphorescent material derived from a triplet excited state of electrons according to a light emitting mechanism. . In addition, the light emitting material may be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to achieve a better natural color according to the light emitting color.

한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트-도판트 시스템을 사용할 수 있다.On the other hand, when only one material is used as the light emitting material, the maximum emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect. A host-dopant system can be used as the luminescent material to increase the luminous efficiency through.

그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때, 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.When the dopant having a smaller energy band gap than the host forming the light emitting layer is mixed with a small amount of the light emitting layer, the excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.

유기전계발광소자가 전술한 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨대 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지 안정하고 효율적인 유기전계발광소자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 당 기술분야에서는 새로운 재료의 개발이 계속 요구되고 있는 실정이다.In order for the organic electroluminescent device to fully exhibit the above-mentioned excellent features, the organic layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. is supported by a stable and efficient material Although this should be preceded, the development of a stable and efficient organic material layer for an organic light emitting device has not been made yet. Therefore, the development of new materials in the art continues to be required.

본 발명이 이루고자 하는 기술적 과제는 구동전압이 낮고 발광효율이 우수한 특성을 갖는 신규한 축합아릴 화합물을 제공하는 것이다.The technical problem to be achieved by the present invention is to provide a novel condensed aryl compound having a low driving voltage and excellent luminous efficiency.

본 발명이 이루고자 하는 두 번째 기술적 과제는 상기 신규한 축합아릴 화합물을 포함하는 유기전계발광소자를 제공하는 것이다.The second technical problem to be achieved by the present invention is to provide an organic electroluminescent device comprising the novel condensed aryl compound.

따라서, 본 발명은 상기 첫 번째 기술적 과제를 달성하기 위하여,Therefore, the present invention to achieve the first technical problem,

하기 [화학식 1]로 표시되는 축합아릴 화합물을 제공한다.It provides a condensed aryl compound represented by the following [Formula 1].

[화학식 1][Formula 1]

Figure pat00001
Figure pat00001

상기 [화학식 1]에서,In the above formula (1)

상기 X는 O, S, P, NR5, CR5R6 또는 SiR5R6이고, 상기 R1 내지 R6, A1, A2, B1 및 B2는 서로 동일하거나 상이하며,X is O, S, P, NR 5 , CR 5 R 6 or SiR 5 R 6 , wherein R 1 to R 6 , A 1 , A 2 , B 1 and B 2 are the same as or different from each other,

상기 R1 내지 R6, A1, A2, B1 및 B2는 각각 독립적으로 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 히드록시기, 니트로기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군에서 선택되고,R 1 to R 6 , A 1 , A 2 , B 1 and B 2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 2 to 30 carbon atoms Alkenyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms 6 To 30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 alkylamine group, substituted Or an unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, substituted Or beach A substituted silicon group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxy group, a nitro group, a halogen group, an amide group and an ester group,

상기 L1 및 L2는 화학결합 또는 2가의 연결기로서 치환 또는 비치환된 탄소수 1 내지 30의 알킬렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬렌기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로아릴렌기로 이루어진 군에서 선택될 수 있다.The L 1 and L 2 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon atom 3 to 30 as a chemical bond or a divalent linking group. It may be selected from the group consisting of a cycloalkylene group, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms.

본 발명의 일 실시예에 의하면, 상기 R1 내지 R6, A1, A2, B1, B2, L1 및 L2는 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 니트로기, 히드록시기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군으로부터 1종 이상으로 더 치환될 수 있다.According to an embodiment of the present invention, R 1 to R 6 , A 1 , A 2 , B 1 , B 2 , L 1 and L 2 are hydrogen atoms, deuterium atoms, substituted or unsubstituted carbon atoms having 1 to 30 carbon atoms. Alkyl group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted carbon atoms 1 to 30 30 alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted A substituted C1-C30 alkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C5-C50 aryl group, a substituted or unsubstituted hetero atom, O, N or S Hetero having 3 to 50 carbon atoms Aryl group, substituted or unsubstituted silicone group, substituted or unsubstituted boron group, substituted or unsubstituted silane group, carbonyl group, phosphoryl group, amino group, nitrile group, nitro group, hydroxy group, halogen group, amide group and ester It may be further substituted with one or more from the group consisting of groups.

본 발명의 다른 일 실시예에 의하면, 상기 R1 내지 R6, A1, A2, B1, B2, L1 ,L2 및 치환기는 서로 인접한 기와 지방족, 방향족, 지방족헤테로 또는 방향족헤테로의 축합고리를 형성하거나 스피로결합을 이룰 수 있다.According to another embodiment of the present invention, the R 1 to R 6 , A 1 , A 2 , B 1 , B 2 , L 1 , L 2 and the substituents are adjacent to each other and the aliphatic, aromatic, aliphatic hetero or aromatic hetero It can form condensed rings or spiro bonds.

본 발명은 상기 두 번째 기술적 과제를 달성하기 위하여,The present invention to achieve the second technical problem,

애노드, 캐소드 및상기 애노드와 상기 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 축합아릴 화합물을 포함하는 유기전계발광소자를 제공한다.It provides an organic light emitting device comprising an anode, a cathode, and a condensed aryl compound represented by the above [Formula 1] interposed between the anode and the cathode.

본 발명에 따르면, [화학식 1]로 표시되는 축합아릴 화합물은 기존 물질에 비하여 안정적이고 우수한 발광 특성을 가지므로 이를 포함하는 유기전계발광 소자는 저전압 구동이 가능하고 발광효율을 개선시킬 수 있다.According to the present invention, the condensed aryl compound represented by [Formula 1] has a stable and excellent light emission characteristics compared to the existing material, so that the organic light emitting device including the low voltage can be driven and improve the luminous efficiency.

도 1은 본 발명의 일 구체예에 따른 유기전계발광소자의 개략도이다.1 is a schematic diagram of an organic light emitting display device according to an embodiment of the present invention.

이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.

본 발명은 유기전계소자의 발광층에 포함되는 신규한 축합아릴 화합물로서, 상기 [화학식 1]로 표시되는 화합물인 것을 특징으로 한다.The present invention is a novel condensed aryl compound included in the light emitting layer of the organic field device, characterized in that the compound represented by the above [Formula 1].

본 발명에 따른 상기 [화학식 1]의 축합아릴 화합물에 있어서, 그 치환기를 보다 구체적으로 설명하면 하기와 같다.In the condensed aryl compound of [Formula 1] according to the present invention, the substituents will be described in more detail as follows.

상기 R1 내지 R6, A1, A2, B1, B2, L1 및 L2는 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 니트로기, 히드록시기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군으로부터 1종 이상으로 더 치환될 수 있는 것을 특징으로 한다.R 1 to R 6 , A 1 , A 2 , B 1 , B 2 , L 1 and L 2 are hydrogen atom, deuterium atom, substituted or unsubstituted C1-30 alkyl group, substituted or unsubstituted C2 Alkenyl group having 3 to 30, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted Substituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine having 1 to 30 carbon atoms A heteroaryl group having 3 to 50 carbon atoms, having a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted and having O, N or S as a hetero atom. Group, substituted or unsubstituted yarn At least one further from the group consisting of a cone group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a nitro group, a hydroxyl group, a halogen group, an amide group and an ester group Characterized in that can be substituted.

또한, 상기 R1 내지 R6, A1, A2, B1, B2, L1, L2 및 치환기는 서로 인접한 기와 지방족, 방향족, 지방족헤테로 또는 방향족헤테로의 축합고리를 형성하거나 스피로결합을 이룰 수 있다.In addition, the R 1 to R 6 , A 1 , A 2 , B 1 , B 2 , L 1 , L 2 and the substituents form a condensed ring of an aliphatic, aromatic, aliphatic hetero or aromatic hetero group with adjacent groups or spiro bonds. Can be achieved.

본 발명에 있어서, "치환 또는 비치환된"이라는 용어는 아릴기, 헤테로아릴기, 알킬기, 헤테로알킬기, 사이클로알킬기, 알콕시기, 시아노기, 할로겐기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 게르마늄, 인, 보론, 중수소 및 수소로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되는 것을 의미한다.In the present invention, the term "substituted or unsubstituted" is aryl group, heteroaryl group, alkyl group, heteroalkyl group, cycloalkyl group, alkoxy group, cyano group, halogen group, aryloxy group, alkylsilyl group, arylsilyl group It means that it is unsubstituted or substituted with one or more substituents selected from the group consisting of germanium, phosphorus, boron, deuterium and hydrogen.

상술한 바와 같은 구조를 갖는 상기 [화학식 1]에 따른 신규한 축합아릴 화합물에 대한 구체적인 예에 의해서 본 발명이 제한되는 것은 아니지만, 구체적으로 하기 [화학식 2] 내지 [화학식 49]로 표시되는 화합물 중 어느 하나일 수 있다.Although the present invention is not limited by the specific examples of the novel condensed aryl compound according to [Formula 1] having the structure as described above, specifically, among the compounds represented by the following [Formula 2] to [Formula 49] It can be either.

Figure pat00002
Figure pat00002

[화학식 2] [화학식 3][Formula 2] [Formula 3]

Figure pat00003
Figure pat00003

[화학식 4] [화학식 5][Formula 4] [Formula 5]

Figure pat00004
Figure pat00004

[화학식 6] [화학식 7][Chemical Formula 6] < EMI ID =

Figure pat00005
Figure pat00005

[화학식 8] [화학식 9][Formula 8] [Formula 9]

Figure pat00006
Figure pat00006

[화학식 10] [화학식 11][Formula 10] [Formula 11]

Figure pat00007
Figure pat00007

[화학식 12] [화학식 13][Formula 12] [Formula 13]

[화학식 14] [화학식 15][Formula 14] [Formula 15]

Figure pat00009
Figure pat00009

[화학식 16] [화학식 17][Formula 16] [Formula 17]

Figure pat00010
Figure pat00010

[화학식 18] [화학식 19][Formula 18] [Formula 19]

Figure pat00011
Figure pat00011

[화학식 20] [화학식 21][Formula 20] [Formula 21]

Figure pat00012
Figure pat00012

[화학식 22] [화학식 23][Formula 22] [Formula 23]

Figure pat00013
Figure pat00013

[화학식 24] [화학식 25][Formula 24] [Formula 25]

Figure pat00014
Figure pat00014

[화학식 26] [화학식 27][Formula 26] [Formula 27]

Figure pat00015
Figure pat00015

[화학식 28] [화학식 29][Formula 28] [Formula 29]

Figure pat00016
Figure pat00016

[화학식 30] [화학식 31][Formula 30] [Formula 31]

Figure pat00017
Figure pat00017

[화학식 32] [화학식 33][Formula 32] [Formula 33]

Figure pat00018
Figure pat00018

[화학식 34] [화학식 35][Formula 34] [Formula 35]

Figure pat00019
Figure pat00019

[화학식 36] [화학식 37][Formula 36] [Formula 37]

Figure pat00020
Figure pat00020

[화학식 38] [화학식 39][Formula 38] [Formula 39]

Figure pat00021
Figure pat00021

[화학식 40] [화학식 41][Formula 40] [Formula 41]

Figure pat00022
Figure pat00022

[화학식 42] [화학식 43][Formula 42] [Formula 43]

Figure pat00023
Figure pat00023

[화학식 44] [화학식 45][Formula 44] [Formula 45]

Figure pat00024
Figure pat00024

[화학식 46] [화학식 47][Formula 46] [Formula 47]

Figure pat00025
Figure pat00025

[화학식 48] [화학식 49][Formula 48] [Formula 49]

또한, 본 발명에 따른 상기 [화학식 1]에 따른 신규한 축합아릴 화합물은 구체적으로 하기 [화학식 50] 내지 [화학식 1265]로 표시되는 화합물 중 어느 하나일 수 있다.In addition, the novel condensed aryl compound according to [Formula 1] according to the present invention may be specifically any one of the compounds represented by the following [Formula 50] to [Formula 1265].

[화학식50] [화학식51] [화학식52] [화학식53][Formula 50] [Formula 51] [Formula 52] [Formula 53]

Figure pat00026
Figure pat00026

[화학식54] [화학식55] [화학식56] [화학식57][Formula 54] [Formula 55] [Formula 56] [Formula 57]

Figure pat00027
Figure pat00027

[화학식58] [화학식59] [화학식60] [화학식61][Formula 58] [Formula 59] [Formula 60] [Formula 61]

Figure pat00028
Figure pat00028

[화학식62] [화학식63] [화학식64] [화학식65][Formula 62] [Formula 63] [Formula 64] [Formula 65]

Figure pat00029
Figure pat00029

[화학식66] [화학식67] [화학식68] [화학식69][Formula 66] [Formula 67] [Formula 68] [Formula 69]

Figure pat00030
[화학식70] [화학식71] [화학식72] [화학식73]
Figure pat00030
[Formula 70] [Formula 71] [Formula 72] [Formula 73]

Figure pat00031
[화학식74] [화학식75] [화학식76] [화학식77]
Figure pat00031
[Formula 74] [Formula 75] [Formula 76] [Formula 77]

Figure pat00032
[화학식78] [화학식79] [화학식80] [화학식81]
Figure pat00032
[Formula 78] [Formula 79] [Formula 80] [Formula 81]

Figure pat00033
[화학식82] [화학식83] [화학식84] [화학식85]
Figure pat00033
[Formula 82] [Formula 83] [Formula 84] [Formula 85]

Figure pat00034
[화학식86] [화학식87] [화학식88] [화학식89]
Figure pat00034
[Formula 86] [Formula 87] [Formula 88] [Formula 89]

Figure pat00035
[화학식90] [화학식91] [화학식92] [화학식93]
Figure pat00035
[Formula 90] [Formula 91] [Formula 92] [Formula 93]

Figure pat00036
[화학식94] [화학식95] [화학식96] [화학식97]
Figure pat00036
[Formula 94] [Formula 95] [Formula 96] [Formula 97]

Figure pat00037
[화학식98] [화학식99] [화학식100] [화학식101]
Figure pat00037
[Formula 98] [Formula 99] [Formula 100] [Formula 101]

Figure pat00038
[화학식102] [화학식103] [화학식104] [화학식105]
Figure pat00038
[Formula 102] [Formula 103] [Formula 104] [Formula 105]

Figure pat00039
[화학식106] [화학식107] [화학식108] [화학식109]
Figure pat00039
[Formula 106] [Formula 107] [Formula 108] [Formula 109]

Figure pat00040
[화학식110] [화학식111] [화학식112] [화학식113]
Figure pat00040
[Formula 110] [Formula 111] [Formula 112] [Formula 113]

Figure pat00041
[화학식114] [화학식115] [화학식116] [화학식117]
Figure pat00041
[Formula 114] [Formula 115] [Formula 116] [Formula 117]

Figure pat00042
[화학식118] [화학식119] [화학식120] [화학식121]
Figure pat00042
[Formula 118] [Formula 119] [Formula 120] [Formula 121]

Figure pat00043
[화학식122] [화학식123] [화학식124] [화학식125]
Figure pat00043
[Formula 122] [Formula 123] [Formula 124] [Formula 125]

Figure pat00044
[화학식126] [화학식127] [화학식128] [화학식129]
Figure pat00044
[Formula 126] [Formula 127] [Formula 128] [Formula 129]

Figure pat00045
[화학식130] [화학식131] [화학식132] [화학식133]
Figure pat00045
[Formula 130] [Formula 131] [Formula 132] [Formula 133]

Figure pat00046
[화학식134] [화학식135] [화학식136] [화학식137]
Figure pat00046
[Formula 134] [Formula 135] [Formula 136] [Formula 137]

Figure pat00047
[화학식138] [화학식139] [화학식140] [화학식141]
Figure pat00047
[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]

Figure pat00048
[화학식142] [화학식143] [화학식144] [화학식145]
Figure pat00048
[Formula 142] [Formula 143] [Formula 144] [Formula 145]

Figure pat00049
[화학식146] [화학식147] [화학식148] [화학식149]
Figure pat00049
[Formula 146] [Formula 147] [Formula 148] [Formula 149]

Figure pat00050
[화학식150] [화학식151] [화학식152] [화학식153]
Figure pat00050
[Formula 150] [Formula 151] [Formula 152] [Formula 153]

Figure pat00051
Figure pat00051

[화학식154] [화학식155] [화학식156] [화학식157][Formula 154] [Formula 155] [Formula 156] [Formula 157]

Figure pat00052
Figure pat00052

[화학식158] [화학식159] [화학식160] [화학식161][Formula 158] [Formula 159] [Formula 160] [Formula 161]

Figure pat00053
Figure pat00053

[화학식162] [화학식163] [화학식164] [화학식165][Formula 162] [Formula 163] [Formula 164] [Formula 165]

Figure pat00054
Figure pat00054

[화학식166] [화학식167] [화학식168] [화학식169][Formula 166] [Formula 167] [Formula 168] [Formula 169]

Figure pat00055
Figure pat00055

[화학식170] [화학식171] [화학식172] [화학식173][Formula 170] [Formula 171] [Formula 172] [Formula 173]

Figure pat00056
Figure pat00056

[화학식174] [화학식175] [화학식176] [화학식177][Formula 174] [Formula 175] [Formula 176] [Formula 177]

Figure pat00057
Figure pat00057

[화학식178] [화학식179] [화학식180] [화학식181][Formula 178] [Formula 179] [Formula 180] [Formula 181]

Figure pat00058
Figure pat00058

[화학식182] [화학식183] [화학식184] [화학식185][Formula 182] [Formula 183] [Formula 184] [Formula 185]

Figure pat00059
Figure pat00059

[화학식186] [화학식187] [화학식188] [화학식189][Formula 186] [Formula 187] [Formula 188] [Formula 189]

Figure pat00060
Figure pat00060

[화학식190] [화학식191] [화학식192] [화학식193][Formula 190] [Formula 191] [Formula 192] [Formula 193]

Figure pat00061
Figure pat00061

[화학식194] [화학식195] [화학식196] [화학식197][Formula 194] [Formula 195] [Formula 196] [Formula 197]

Figure pat00062
Figure pat00062

[화학식198] [화학식199] [화학식200] [화학식201][Formula 198] [Formula 199] [Formula 200] [Formula 201]

Figure pat00063
Figure pat00063

[화학식202] [화학식203] [화학식204] [화학식205][Formula 202] [Formula 203] [Formula 204] [Formula 205]

Figure pat00064
Figure pat00064

[화학식206] [화학식207] [화학식208] [화학식209][Formula 206] [Formula 207] [Formula 208] [Formula 209]

Figure pat00065
Figure pat00065

[화학식210] [화학식211] [화학식212] [화학식213][Formula 210] [Formula 211] [Formula 212] [Formula 213]

Figure pat00066
Figure pat00066

[화학식214] [화학식215] [화학식216] [화학식217][Formula 214] [Formula 215] [Formula 216] [Formula 217]

Figure pat00067
Figure pat00067

[화학식218] [화학식219] [화학식220] [화학식221][Formula 218] [Formula 219] [Formula 220] [Formula 221]

Figure pat00068
Figure pat00068

[화학식222] [화학식223] [화학식224] [화학식225][Formula 222] [Formula 223] [Formula 224] [Formula 225]

Figure pat00069
Figure pat00069

[화학식226] [화학식227] [화학식228] [화학식229][Formula 226] [Formula 227] [Formula 228] [Formula 229]

Figure pat00070
Figure pat00070

[화학식230] [화학식231] [화학식232] [화학식233][Formula 230] [Formula 231] [Formula 232] [Formula 233]

Figure pat00071
Figure pat00071

[화학식234] [화학식235] [화학식236] [화학식237][Formula 234] [Formula 235] [Formula 236] [Formula 237]

Figure pat00072
Figure pat00072

[화학식238] [화학식239] [화학식240] [화학식241][Formula 238] [Formula 239] [Formula 240] [Formula 241]

Figure pat00073
Figure pat00073

[화학식242] [화학식243] [화학식244] [화학식245][Formula 242] [Formula 243] [Formula 244] [Formula 245]

Figure pat00074
Figure pat00074

[화학식246] [화학식247] [화학식248] [화학식249][Formula 246] [Formula 247] [Formula 248] [Formula 249]

Figure pat00075
Figure pat00075

[화학식250] [화학식251] [화학식252] [화학식253][Formula 250] [Formula 251] [Formula 252] [Formula 253]

Figure pat00076
Figure pat00076

[화학식254] [화학식255] [화학식256] [화학식257][Formula 254] [Formula 255] [Formula 256] [Formula 257]

Figure pat00077
Figure pat00077

[화학식258] [화학식259] [화학식260] [화학식261][Formula 258] [Formula 259] [Formula 260] [Formula 261]

Figure pat00078
Figure pat00078

[화학식262] [화학식263] [화학식264] [화학식265][Formula 262] [Formula 263] [Formula 264] [Formula 265]

Figure pat00079
Figure pat00079

[화학식266] [화학식267] [화학식268] [화학식269][Formula 266] [Formula 267] [Formula 268] [Formula 269]

Figure pat00080
Figure pat00080

[화학식270] [화학식271] [화학식272] [화학식273][Formula 270] [Formula 271] [Formula 272] [Formula 273]

Figure pat00081
Figure pat00081

[화학식274] [화학식275] [화학식276] [화학식277][Formula 274] [Formula 275] [Formula 276] [Formula 277]

Figure pat00082
Figure pat00082

[화학식278] [화학식279] [화학식280] [화학식281][Formula 278] [Formula 279] [Formula 280] [Formula 281]

Figure pat00083
Figure pat00083

[화학식282] [화학식283] [화학식284] [화학식285][Formula 282] [Formula 283] [Formula 284] [Formula 285]

Figure pat00084
Figure pat00084

[화학식286] [화학식287] [화학식288] [화학식289][Formula 286] [Formula 287] [Formula 288] [Formula 289]

Figure pat00085
Figure pat00085

[화학식290] [화학식291] [화학식292] [화학식293][Formula 290] [Formula 291] [Formula 292] [Formula 293]

Figure pat00086
Figure pat00086

[화학식294] [화학식295] [화학식296] [화학식297][Formula 294] [Formula 295] [Formula 296] [Formula 297]

Figure pat00087
Figure pat00087

[화학식298] [화학식299] [화학식300] [화학식301][Formula 298] [Formula 299] [Formula 300] [Formula 301]

Figure pat00088
Figure pat00088

[화학식302] [화학식303] [화학식304] [화학식305][Formula 302] [Formula 303] [Formula 304] [Formula 305]

Figure pat00089
Figure pat00089

[화학식306] [화학식307] [화학식308] [화학식309][Formula 306] [Formula 307] [Formula 308] [Formula 309]

Figure pat00090
Figure pat00090

[화학식310] [화학식311] [화학식312] [화학식313][Formula 310] [Formula 311] [Formula 312] [Formula 313]

Figure pat00091
Figure pat00091

[화학식314] [화학식315] [화학식316] [화학식317][Formula 314] [Formula 315] [Formula 316] [Formula 317]

Figure pat00092
Figure pat00092

[화학식318] [화학식319] [화학식320] [화학식321][Formula 318] [Formula 319] [Formula 320] [Formula 321]

Figure pat00093
Figure pat00093

[화학식322] [화학식323] [화학식324] [화학식325][Formula 322] [Formula 323] [Formula 324] [Formula 325]

Figure pat00094
Figure pat00094

[화학식326] [화학식327] [화학식328] [화학식329][Formula 326] [Formula 327] [Formula 328] [Formula 329]

Figure pat00095
Figure pat00095

[화학식330] [화학식331] [화학식332] [화학식333][Formula 330] [Formula 331] [Formula 332] [Formula 333]

Figure pat00096
Figure pat00096

[화학식334] [화학식335] [화학식336] [화학식337][Formula 334] [Formula 335] [Formula 336] [Formula 337]

Figure pat00097
Figure pat00097

[화학식338] [화학식339] [화학식340] [화학식341][Formula 338] [Formula 339] [Formula 340] [Formula 341]

Figure pat00098
Figure pat00098

[화학식342] [화학식343] [화학식344] [화학식345][Formula 342] [Formula 343] [Formula 344] [Formula 345]

Figure pat00099
Figure pat00099

[화학식346] [화학식347] [화학식348] [화학식349][Formula 346] [Formula 347] [Formula 348] [Formula 349]

Figure pat00100
Figure pat00100

[화학식350] [화학식351] [화학식352] [화학식353][Formula 350] [Formula 351] [Formula 352] [Formula 353]

Figure pat00101
Figure pat00101

[화학식354] [화학식355] [화학식356] [화학식357][Formula 354] [Formula 355] [Formula 356] [Formula 357]

Figure pat00102
Figure pat00102

[화학식358] [화학식359] [화학식360] [화학식361][Formula 358] [Formula 359] [Formula 360] [Formula 361]

Figure pat00103
Figure pat00103

[화학식362] [화학식363] [화학식364] [화학식365][Formula 362] [Formula 363] [Formula 364] [Formula 365]

Figure pat00104
Figure pat00104

[화학식366] [화학식367] [화학식368] [화학식369][Formula 366] [Formula 367] [Formula 368] [Formula 369]

Figure pat00105
Figure pat00105

[화학식370] [화학식371] [화학식372] [화학식373][Formula 370] [Formula 371] [Formula 372] [Formula 373]

Figure pat00106
Figure pat00106

[화학식374] [화학식375] [화학식376] [화학식377][Formula 374] [Formula 375] [Formula 376] [Formula 377]

Figure pat00107
Figure pat00107

[화학식378] [화학식379] [화학식380] [화학식381][Formula 378] [Formula 379] [Formula 380] [Formula 381]

Figure pat00108
Figure pat00108

[화학식382] [화학식383] [화학식384] [화학식385][Formula 382] [Formula 383] [Formula 384] [Formula 385]

Figure pat00109
Figure pat00109

[화학식386] [화학식387] [화학식388] [화학식389][Formula 386] [Formula 387] [Formula 388] [Formula 389]

Figure pat00110
Figure pat00110

[화학식390] [화학식391 ] [화학식392] [화학식393][Formula 390] [Formula 391] [Formula 392] [Formula 393]

Figure pat00111
Figure pat00111

[화학식394] [화학식395] [화학식396] [화학식397][Formula 394] [Formula 395] [Formula 396] [Formula 397]

Figure pat00112
Figure pat00112

[화학식398] [화학식399] [화학식400] [화학식401][Formula 398] [Formula 399] [Formula 400] [Formula 401]

Figure pat00113
Figure pat00113

[화학식402] [화학식403] [화학식404] [화학식405][Formula 402] [Formula 403] [Formula 404] [Formula 405]

Figure pat00114
Figure pat00114

[화학식406] [화학식407] [화학식408] [화학식409][Formula 406] [Formula 407] [Formula 408] [Formula 409]

Figure pat00115
Figure pat00115

[화학식410] [화학식411] [화학식412] [화학식413][Formula 410] [Formula 411] [Formula 412] [Formula 413]

Figure pat00116
Figure pat00116

[화학식414] [화학식415] [화학식416] [화학식417][Formula 414] [Formula 415] [Formula 416] [Formula 417]

Figure pat00117
Figure pat00117

[화학식418] [화학식419] [화학식420] [화학식421][Formula 418] [Formula 419] [Formula 420] [Formula 421]

Figure pat00118
Figure pat00118

[화학식422] [화학식423] [화학식424] [화학식425][Formula 422] [Formula 423] [Formula 424] [Formula 425]

Figure pat00119
Figure pat00119

[화학식426] [화학식427] [화학식428] [화학식429][Formula 426] [Formula 427] [Formula 428] [Formula 429]

Figure pat00120
Figure pat00120

[화학식430] [화학식431] [화학식432] [화학식433][Formula 430] [Formula 431] [Formula 432] [Formula 433]

Figure pat00121
Figure pat00121

[화학식434] [화학식435] [화학식436] [화학식437][Formula 434] [Formula 435] [Formula 436] [Formula 437]

Figure pat00122
Figure pat00122

[화학식438] [화학식439] [화학식440] [화학식441][Formula 438] [Formula 439] [Formula 440] [Formula 441]

Figure pat00123
Figure pat00123

[화학식442] [화학식443] [화학식444] [화학식445][Formula 442] [Formula 443] [Formula 444] [Formula 445]

Figure pat00124
Figure pat00124

[화학식446] [화학식447] [화학식448] [화학식449][Formula 446] [Formula 447] [Formula 448] [Formula 449]

Figure pat00125
Figure pat00125

[화학식450] [화학식451] [화학식452] [화학식453][Formula 450] [Formula 451] [Formula 452] [Formula 453]

Figure pat00126
Figure pat00126

[화학식454] [화학식455] [화학식456] [화학식457][Formula 454] [Formula 455] [Formula 456] [Formula 457]

Figure pat00127
Figure pat00127

[화학식458] [화학식459] [화학식460] [화학식461][Formula 458] [Formula 459] [Formula 460] [Formula 461]

Figure pat00128
Figure pat00128

[화학식462] [화학식463] [화학식464] [화학식465][Formula 462] [Formula 463] [Formula 464] [Formula 465]

Figure pat00129
Figure pat00129

[화학식466] [화학식467] [화학식468] [화학식469][Formula 466] [Formula 467] [Formula 468] [Formula 469]

Figure pat00130
Figure pat00130

[화학식470] [화학식471] [화학식472] [화학식473][Formula 470] [Formula 471] [Formula 472] [Formula 473]

Figure pat00131
Figure pat00131

[화학식474] [화학식475] [화학식476] [화학식477][Formula 474] [Formula 475] [Formula 476] [Formula 477]

Figure pat00132
Figure pat00132

[화학식478] [화학식479] [화학식480] [화학식481][Formula 478] [Formula 479] [Formula 480] [Formula 481]

Figure pat00133
Figure pat00133

[화학식482] [화학식483] [화학식484] [화학식485][Formula 482] [Formula 483] [Formula 484] [Formula 485]

Figure pat00134
Figure pat00134

[화학식486] [화학식487] [화학식488] [화학식489][Formula 486] [Formula 487] [Formula 488] [Formula 489]

Figure pat00135
Figure pat00135

[화학식490] [화학식491] [화학식492] [화학식493][Formula 490] [Formula 491] [Formula 492] [Formula 493]

Figure pat00136
Figure pat00136

[화학식494] [화학식495] [화학식496] [화학식497][Formula 494] [Formula 495] [Formula 496] [Formula 497]

Figure pat00137
Figure pat00137

[화학식498] [화학식499] [화학식500] [화학식501][Formula 498] [Formula 499] [Formula 500] [Formula 501]

Figure pat00138
Figure pat00138

[화학식502] [화학식503] [화학식504] [화학식505][Formula 502] [Formula 503] [Formula 504] [Formula 505]

Figure pat00139
Figure pat00139

[화학식506] [화학식507] [화학식508] [화학식509][Formula 506] [Formula 507] [Formula 508] [Formula 509]

Figure pat00140
Figure pat00140

[화학식510] [화학식511] [화학식512] [화학식513][Formula 510] [Formula 511] [Formula 512] [Formula 513]

Figure pat00141
Figure pat00141

[화학식514] [화학식515] [화학식516] [화학식517]Formula 514] Formula 515 Formula 516 Formula 517

Figure pat00142
Figure pat00142

[화학식518] [화학식519] [화학식520] [화학식521]Formula 518] Formula 519 Formula 520

Figure pat00143
Figure pat00143

[화학식522] [화학식523] [화학식524] [화학식525][Formula 522] [Formula 523] [Formula 524] [Formula 525]

Figure pat00144
Figure pat00144

[화학식526] [화학식527] [화학식528] [화학식529][526] [Formula 527] [Formula 528] [Formula 529]

Figure pat00145
Figure pat00145

[화학식530] [화학식531] [화학식532] [화학식533][Formula 530] [Formula 531] [Formula 532] [Formula 533]

Figure pat00146
Figure pat00146

[화학식534] [화학식535] [화학식536] [화학식537][Formula 534] [Formula 535] [Formula 536] [Formula 537]

Figure pat00147
Figure pat00147

[화학식538] [화학식539] [화학식540] [화학식541][Formula 538] [Formula 539] [Formula 540] [Formula 541]

Figure pat00148
Figure pat00148

[화학식542] [화학식543] [화학식544] [화학식545][542] [Formula 543] [Formula 544] [Formula 545]

Figure pat00149
Figure pat00149

[화학식546] [화학식547] [화학식548] [화학식549]Formula 546 Formula 547 Formula 548 Formula 549

Figure pat00150
Figure pat00150

[화학식550] [화학식551] [화학식552] [화학식553][Chemical Formula 550] [Chemical Formula 551] [Chemical Formula 552]

Figure pat00151
Figure pat00151

[화학식554] [화학식555] [화학식556] [화학식557][Formula 554] [Formula 555] [Formula 556] [Formula 557]

Figure pat00152
Figure pat00152

[화학식558] [화학식559] [화학식560] [화학식561]Formula 558 Formula 559 Formula 560 Formula 561

Figure pat00153
Figure pat00153

[화학식562] [화학식563] [화학식564] [화학식565][562] [Formula 563] [Formula 564] [Formula 565]

Figure pat00154
Figure pat00154

[화학식566] [화학식567] [화학식568] [화학식569][Formula 566] [Formula 567] [Formula 568] [Formula 569]

Figure pat00155
Figure pat00155

[화학식570] [화학식571] [화학식572] [화학식573][570] [Formula 571] [Formula 572] [Formula 573]

Figure pat00156
Figure pat00156

[화학식574] [화학식575] [화학식576] [화학식577][Formula 574] [Formula 575] [Formula 576] [Formula 577]

Figure pat00157
Figure pat00157

[화학식578] [화학식579] [화학식580] [화학식581][Formula 578] [Formula 579] [Formula 580] [Formula 581]

Figure pat00158
Figure pat00158

[화학식582] [화학식583] [화학식584] [화학식585][58] [Formula 584] [Formula 584] [Formula 585]

Figure pat00159
Figure pat00159

[화학식586] [화학식587] [화학식588] [화학식589][Formula 586] [Formula 587] [Formula 588] [Formula 589]

Figure pat00160
Figure pat00160

[화학식590] [화학식591] [화학식592] [화학식593][590] [Formula 591] [Formula 592] [Formula 593]

Figure pat00161
Figure pat00161

[화학식594] [화학식595] [화학식596] [화학식597][Formula 595] [Formula 595] [Formula 596] [Formula 597]

Figure pat00162
Figure pat00162

[화학식598] [화학식599] [화학식600] [화학식601][Formula 598] [Formula 599] [Formula 600] [Formula 601]

Figure pat00163
Figure pat00163

[화학식602] [화학식603] [화학식604] [화학식605][Formula 602] [Formula 603] [Formula 604] [Formula 605]

Figure pat00164
Figure pat00164

[화학식606] [화학식607] [화학식608] [화학식609][Formula 606] [Formula 607] [Formula 608] [Formula 609]

Figure pat00165
Figure pat00165

[화학식610] [화학식611] [화학식612] [화학식613][Formula 610] [Formula 611] [Formula 612] [Formula 613]

Figure pat00166
Figure pat00166

[화학식614] [화학식615] [화학식616] [화학식617][Formula 614] [Formula 615] [Formula 616] [Formula 617]

Figure pat00167
Figure pat00167

[화학식618] [화학식619] [화학식620] [화학식621]Formula 618] Formula 619 Formula 620

Figure pat00168
Figure pat00168

[화학식622] [화학식623] [화학식624] [화학식625][Formula 622] [Formula 623] [Formula 624] [Formula 625]

Figure pat00169
Figure pat00169

[화학식626] [화학식627] [화학식628] [화학식629][Formula 626] [Formula 627] [Formula 628] [Formula 629]

Figure pat00170
Figure pat00170

[화학식630] [화학식631] [화학식632] [화학식633][630] [Formula 631] [Formula 632] [Formula 633]

Figure pat00171
Figure pat00171

[화학식634] [화학식635] [화학식636] [화학식637][Formula 634] [Formula 635] [Formula 636] [Formula 637]

Figure pat00172
Figure pat00172

[화학식638] [화학식639] [화학식640] [화학식641][Formula 638] [Formula 639] [Formula 640] [Formula 641]

Figure pat00173
Figure pat00173

[화학식642] [화학식643] [화학식644] [화학식645][642] [Formula 643] [Formula 644] [Formula 645]

Figure pat00174
Figure pat00174

[화학식646] [화학식647] [화학식648] [화학식649][Formula 646] [Formula 647] [Formula 648] [Formula 649]

Figure pat00175
Figure pat00175

[화학식650] [화학식651] [화학식652] [화학식653][650] [Formula 651] [Formula 652] [Formula 653]

Figure pat00176
Figure pat00176

[화학식654] [화학식655] [화학식656] [화학식657][654] [Formula 655] [Formula 656] [Formula 657]

Figure pat00177
Figure pat00177

[화학식658] [화학식659] [화학식660] [화학식661][Formula 658] [Formula 659] [Formula 660] [Formula 661]

Figure pat00178
Figure pat00178

[화학식662] [화학식663] [화학식664] [화학식665][662] [Formula 663] [Formula 664] [Formula 665]

Figure pat00179
Figure pat00179

[화학식666] [화학식667] [화학식668] [화학식669][Formula 666] [Formula 667] [Formula 668] [Formula 669]

Figure pat00180
Figure pat00180

[화학식670] [화학식671] [화학식672] [화학식673][Formula 670] [Formula 671] [Formula 672] [Formula 673]

Figure pat00181
Figure pat00181

[화학식674] [화학식675] [화학식676] [화학식677][Formula 674] [Formula 675] [Formula 676] [Formula 677]

Figure pat00182
Figure pat00182

[화학식678] [화학식679] [화학식680] [화학식681][Formula 678] [Formula 679] [Formula 680] [Formula 681]

Figure pat00183
Figure pat00183

[화학식682] [화학식683] [화학식684] [화학식685][Formula 682] [Formula 683] [Formula 684] [Formula 685]

Figure pat00184
Figure pat00184

[화학식686] [화학식687] [화학식688] [화학식689][Formula 686] [Formula 687] [Formula 688] [Formula 689]

Figure pat00185
Figure pat00185

[화학식690] [화학식691] [화학식692] [화학식693][690] [Formula 691] [Formula 692] [Formula 693]

Figure pat00186
Figure pat00186

[화학식694] [화학식695] [화학식696] [화학식697][Formula 695] [Formula 695] [Formula 696] [Formula 697]

Figure pat00187
Figure pat00187

[화학식698] [화학식699] [화학식700] [화학식701][Formula 698] [Formula 699] [Formula 700] [Formula 701]

Figure pat00188
Figure pat00188

[화학식702] [화학식703] [화학식704] [화학식705][Formula 702] [Formula 703] [Formula 704] [Formula 705]

Figure pat00189
Figure pat00189

[화학식706] [화학식707] [화학식708] [화학식709][Formula 706] [Formula 707] [Formula 708] [Formula 709]

Figure pat00190
Figure pat00190

[화학식710] [화학식711] [화학식712] [화학식713][Formula 710] [Formula 711] [Formula 712] [Formula 713]

Figure pat00191
Figure pat00191

[화학식714] [화학식715] [화학식716] [화학식717][Formula 714] [Formula 715] [Formula 716] [Formula 717]

Figure pat00192
Figure pat00192

[화학식718] [화학식719] [화학식720] [화학식721][Formula 718] [Formula 719] [Formula 720] [Formula 721]

Figure pat00193
Figure pat00193

[화학식722] [화학식723] [화학식724] [화학식725][Formula 722] [Formula 723] [Formula 724] [Formula 725]

Figure pat00194
Figure pat00194

[화학식726] [화학식727] [화학식728] [화학식729][Formula 726] [Formula 727] [Formula 728] [Formula 729]

Figure pat00195
Figure pat00195

[화학식730] [화학식731] [화학식732] [화학식733][Formula 730] [Formula 731] [Formula 732] [Formula 733]

Figure pat00196
Figure pat00196

[화학식734] [화학식735] [화학식736] [화학식737]Formula 734] Formula 735 Formula 736 Formula 737

Figure pat00197
Figure pat00197

[화학식738] [화학식739] [화학식740] [화학식741][Formula 738] [Formula 739] [Formula 740] [Formula 741]

Figure pat00198
Figure pat00198

[화학식742] [화학식743] [화학식744] [화학식745][Formula 742] [Formula 743] [Formula 744] [Formula 745]

Figure pat00199
Figure pat00199

[화학식746] [화학식747] [화학식748] [화학식749][Formula 746] [Formula 747] [Formula 748] [Formula 749]

Figure pat00200
Figure pat00200

[화학식750] [화학식751] [화학식752] [화학식753]Formula 750] Formula 751] Formula 752

Figure pat00201
Figure pat00201

[화학식754] [화학식755] [화학식756] [화학식757][Formula 754] [Formula 755] [Formula 756] [Formula 757]

Figure pat00202
Figure pat00202

[화학식758] [화학식759] [화학식760] [화학식761][Formula 758] [Formula 759] [Formula 760] [Formula 761]

Figure pat00203
Figure pat00203

[화학식762] [화학식763] [화학식764] [화학식765][Formula 762] [Formula 763] [Formula 764] [Formula 765]

Figure pat00204
Figure pat00204

[화학식766] [화학식767] [화학식768] [화학식769][Formula 766] [Formula 767] [Formula 768] [Formula 769]

Figure pat00205
Figure pat00205

[화학식770] [화학식771] [화학식772] [화학식773][Formula 770] [Formula 771] [Formula 772] [Formula 773]

Figure pat00206
Figure pat00206

[화학식774] [화학식775] [화학식776] [화학식777][Formula 774] [Formula 775] [Formula 776] [Formula 777]

Figure pat00207
Figure pat00207

[화학식778] [화학식779] [화학식780] [화학식781][Formula 778] [Formula 779] [Formula 780] [Formula 781]

Figure pat00208
Figure pat00208

[화학식782] [화학식783] [화학식784] [화학식785][Formula 782] [Formula 783] [Formula 784] [Formula 785]

Figure pat00209
Figure pat00209

[화학식786] [화학식787] [화학식788] [화학식789][Formula 786] [Formula 787] [Formula 788] [Formula 789]

Figure pat00210
Figure pat00210

[화학식790] [화학식791] [화학식792] [화학식793][Formula 790] [Formula 791] [Formula 792] [Formula 793]

Figure pat00211
Figure pat00211

[화학식794] [화학식795] [화학식796] [화학식797][Formula 794] [Formula 795] [Formula 796] [Formula 797]

Figure pat00212
Figure pat00212

[화학식798] [화학식799] [화학식800] [화학식801][Formula 798] [Formula 799] [Formula 800] [Formula 801]

Figure pat00213
Figure pat00213

[화학식802] [화학식803] [화학식804] [화학식805][Formula 802] [Formula 803] [Formula 804] [Formula 805]

Figure pat00214
Figure pat00214

[화학식806] [화학식807] [화학식808] [화학식809][Formula 806] [Formula 807] [Formula 808] [Formula 809]

Figure pat00215
Figure pat00215

[화학식810] [화학식811] [화학식812] [화학식813][Formula 810] [Formula 811] [Formula 812] [Formula 813]

Figure pat00216
Figure pat00216

[화학식814] [화학식815] [화학식816] [화학식817][Formula 814] [Formula 815] [Formula 816] [Formula 817]

Figure pat00217
Figure pat00217

[화학식818] [화학식819] [화학식820] [화학식821][Formula 818] [Formula 819] [Formula 820] [Formula 821]

Figure pat00218
Figure pat00218

[화학식822] [화학식823] [화학식824] [화학식825][822] [Formula 823] [Formula 824] [Formula 825]

Figure pat00219
Figure pat00219

[화학식826] [화학식827] [화학식828] [화학식829][Formula 826] [Formula 827] [Formula 828] [Formula 829]

Figure pat00220
Figure pat00220

[화학식830] [화학식831] [화학식832] [화학식833][Formula 830] [Formula 831] [Formula 832] [Formula 833]

Figure pat00221
Figure pat00221

[화학식834] [화학식835] [화학식836] [화학식837]834 [Formula 835] [Formula 836] [Formula 837]

Figure pat00222
Figure pat00222

[화학식838] [화학식839] [화학식840] [화학식841][Formula 838] [Formula 839] [Formula 840] [Formula 841]

Figure pat00223
Figure pat00223

[화학식842] [화학식843] [화학식844] [화학식845][Formula 842] [Formula 843] [Formula 844] [Formula 845]

Figure pat00224
Figure pat00224

[화학식846] [화학식847] [화학식848] [화학식849][Formula 846] [Formula 847] [Formula 848] [Formula 849]

Figure pat00225
Figure pat00225

[화학식850] [화학식851] [화학식852] [화학식853][Formula 850] [Formula 851] [Formula 852] [Formula 853]

Figure pat00226
Figure pat00226

[화학식854] [화학식855] [화학식856] [화학식857][Formula 854] [Formula 855] [Formula 856] [Formula 857]

Figure pat00227
Figure pat00227

[화학식858] [화학식859] [화학식860] [화학식861][Formula 858] [Formula 859] [Formula 860] [Formula 861]

Figure pat00228
Figure pat00228

[화학식862] [화학식863] [화학식864] [화학식865][Formula 862] [Formula 863] [Formula 864] [Formula 865]

Figure pat00229
Figure pat00229

[화학식866] [화학식867] [화학식868] [화학식869][Formula 866] [Formula 837] [Formula 868] [Formula 869]

Figure pat00230
Figure pat00230

[화학식870] [화학식871] [화학식872] [화학식873]Formula 870 [Formula 871] [Formula 872] [Formula 873]

Figure pat00231
Figure pat00231

[화학식874] [화학식875] [화학식876] [화학식877][Formula 874] [Formula 875] [Formula 876] [Formula 877]

Figure pat00232
Figure pat00232

[화학식878] [화학식879] [화학식880] [화학식881][Formula 878] [Formula 879] [Formula 880] [Formula 881]

Figure pat00233
Figure pat00233

[화학식882] [화학식883] [화학식884] [화학식885][Formula 882] [Formula 883] [Formula 884] [Formula 885]

Figure pat00234
Figure pat00234

[화학식886] [화학식887] [화학식888] [화학식889][Formula 886] [Formula 887] [Formula 888] [Formula 889]

Figure pat00235
Figure pat00235

[화학식890] [화학식891] [화학식892] [화학식893][890] [Formula 891] [Formula 892] [Formula 833]

Figure pat00236
Figure pat00236

[화학식894] [화학식895] [화학식896] [화학식897][Formula 894] [Formula 895] [Formula 896] [Formula 897]

Figure pat00237
Figure pat00237

[화학식898] [화학식899] [화학식900] [화학식901][898] [Formula 899] [Formula 900] [Formula 901]

Figure pat00238
Figure pat00238

[화학식902] [화학식903] [화학식904] [화학식905]Formula 902 Formula 903 Formula 904 Formula 905

Figure pat00239
Figure pat00239

[화학식906] [화학식907] [화학식908] [화학식909][Formula 906] [Formula 907] [Formula 908] [Formula 909]

Figure pat00240
Figure pat00240

[화학식910] [화학식911] [화학식912] [화학식913][Formula 910] [Formula 911] [Formula 912] [Formula 913]

Figure pat00241
Figure pat00241

[화학식914] [화학식915] [화학식916] [화학식917][Formula 914] [Formula 915] [Formula 916] [Formula 917]

Figure pat00242
Figure pat00242

[화학식918] [화학식919] [화학식920] [화학식921][Formula 918] [Formula 919] [Formula 920] [Formula 921]

Figure pat00243
Figure pat00243

[화학식922] [화학식923] [화학식924] [화학식925][92] [Formula 922] [Formula 924] [Formula 925]

Figure pat00244
Figure pat00244

[화학식926] [화학식927] [화학식928] [화학식929]Formula 926] Formula 927 Formula 928 Formula 929

Figure pat00245
Figure pat00245

[화학식930] [화학식931] [화학식932] [화학식933][Formula 930] [Formula 931] [Formula 932] [Formula 933]

Figure pat00246
Figure pat00246

[화학식934] [화학식935] [화학식936] [화학식937][Formula 934] [Formula 935] [Formula 936] [Formula 937]

Figure pat00247
Figure pat00247

[화학식938] [화학식939] [화학식940] [화학식941][Formula 938] [Formula 939] [Formula 940] [Formula 941]

Figure pat00248
Figure pat00248

[화학식942] [화학식943] [화학식944] [화학식945][Formula 942] [Formula 943] [Formula 944] [Formula 945]

Figure pat00249
Figure pat00249

[화학식946] [화학식947] [화학식948] [화학식949][Formula 946] [Formula 947] [Formula 948] [Formula 949]

Figure pat00250
Figure pat00250

[화학식950] [화학식951] [화학식952] [화학식953][Formula 950] [Formula 951] [Formula 952] [Formula 953]

Figure pat00251
Figure pat00251

[화학식954] [화학식955] [화학식956] [화학식957][Formula 954] [Formula 955] [Formula 956] [Formula 957]

Figure pat00252
Figure pat00252

[화학식958] [화학식959] [화학식960] [화학식961][Formula 958] [Formula 959] [Formula 960] [Formula 961]

Figure pat00253
Figure pat00253

[화학식962] [화학식963] [화학식964] [화학식965][Formula 962] [Formula 963] [Formula 964] [Formula 965]

Figure pat00254
Figure pat00254

[화학식966] [화학식967] [화학식968] [화학식969][Formula 966] [Formula 967] [Formula 968] [Formula 969]

Figure pat00255
Figure pat00255

[화학식970] [화학식971] [화학식972] [화학식973][Formula 970] [Formula 971] [Formula 972] [Formula 973]

Figure pat00256
Figure pat00256

[화학식974] [화학식975] [화학식976] [화학식977][Formula 974] [Formula 975] [Formula 976] [Formula 797]

Figure pat00257
Figure pat00257

[화학식978] [화학식979] [화학식980] [화학식981][Formula 978] [Formula 979] [Formula 980] [Formula 981]

Figure pat00258
Figure pat00258

[화학식982] [화학식983] [화학식984] [화학식985][Formula 982] [Formula 983] [Formula 984] [Formula 985]

Figure pat00259
Figure pat00259

[화학식986] [화학식987] [화학식988] [화학식989][Formula 986] [Formula 987] [Formula 988] [Formula 989]

Figure pat00260
Figure pat00260

[화학식990] [화학식991] [화학식992] [화학식993][Formula 990] [Formula 991] [Formula 992] [Formula 993]

Figure pat00261
Figure pat00261

[화학식994] [화학식995] [화학식996] [화학식997][Formula 994] [Formula 995] [Formula 996] [Formula 997]

Figure pat00262
Figure pat00262

[화학식998] [화학식999] [화학식1000] [화학식1001][Formula 998] [Formula 999] [Formula 1000] [Formula 1001]

Figure pat00263
Figure pat00263

[화학식1002] [화학식1003] [화학식1004] [화학식1005][Formula 1002] [Formula 1003] [Formula 1004] [Formula 1005]

Figure pat00264
Figure pat00264

[화학식1006] [화학식1007] [화학식1008] [화학식1009][Formula 1006] [Formula 1007] [Formula 1008] [Formula 1009]

Figure pat00265
Figure pat00265

[화학식1010] [화학식1011] [화학식1012] [화학식1013][Formula 1010] [Formula 1011] [Formula 1012] [Formula 1013]

Figure pat00266
Figure pat00266

[화학식1014] [화학식1015] [화학식1016] [화학식1017][Formula 1014] [Formula 1015] [Formula 1016] [Formula 1017]

Figure pat00267
Figure pat00267

[화학식1018] [화학식1019] [화학식1020] [화학식1021][Formula 1018] [Formula 1019] [Formula 1020] [Formula 1021]

Figure pat00268
Figure pat00268

[화학식1022] [화학식1023] [화학식1024] [화학식1025][Formula 1022] [Formula 1023] [Formula 1024] [Formula 1025]

Figure pat00269
Figure pat00269

[화학식1026] [화학식1027] [화학식1028] [화학식1029][Formula 1026] [Formula 1027] [Formula 1028] [Formula 1029]

Figure pat00270
Figure pat00270

[화학식1030] [화학식1031] [화학식1032] [화학식1033][Formula 1030] [Formula 1031] [Formula 1032] [Formula 1033]

Figure pat00271
Figure pat00271

[화학식1034] [화학식1035] [화학식1036] [화학식1037][Formula 1034] [Formula 1035] [Formula 1036] [Formula 1037]

Figure pat00272
Figure pat00272

[화학식1038] [화학식1039] [화학식1040] [화학식1041][Formula 1038] [Formula 1039] [Formula 1040] [Formula 1041]

Figure pat00273
Figure pat00273

[화학식1042] [화학식1043] [화학식1044] [화학식1045][Formula 1042] [Formula 1043] [Formula 1044] [Formula 1045]

Figure pat00274
Figure pat00274

[화학식1046] [화학식1047] [화학식1048] [화학식1049][Formula 1046] [Formula 1047] [Formula 1048] [Formula 1049]

Figure pat00275
Figure pat00275

[화학식1050] [화학식1051] [화학식1052] [화학식1053][Formula 1050] [Formula 1051] [Formula 1052] [Formula 1053]

Figure pat00276
Figure pat00276

[화학식1054] [화학식1055] [화학식1056] [화학식1057][Formula 1054] [Formula 1055] [Formula 1056] [Formula 1057]

Figure pat00277
Figure pat00277

[화학식1058] [화학식1059] [화학식1060] [화학식1061][Formula 1058] [Formula 1059] [Formula 1060] [Formula 1061]

Figure pat00278
Figure pat00278

[화학식1062] [화학식1063] [화학식1064] [화학식1065][Formula 1062] [Formula 1063] [Formula 1064] [Formula 1065]

Figure pat00279
Figure pat00279

[화학식1066] [화학식1067] [화학식1068] [화학식1069][Formula 1066] [Formula 1067] [Formula 1068] [Formula 1069]

Figure pat00280
Figure pat00280

[화학식1070] [화학식1071] [화학식1072] [화학식1073][Formula 1070] [Formula 1071] [Formula 1072] [Formula 1073]

Figure pat00281
Figure pat00281

[화학식1074] [화학식1075] [화학식1076] [화학식1077][Formula 1074] [Formula 1075] [Formula 1076] [Formula 1077]

Figure pat00282
Figure pat00282

[화학식1078] [화학식1079] [화학식1080] [화학식1081][Formula 1078] [Formula 1079] [Formula 1080] [Formula 1081]

Figure pat00283
Figure pat00283

[화학식1082] [화학식1083] [화학식1084] [화학식1085][Formula 1082] [Formula 1083] [Formula 1084] [Formula 1085]

Figure pat00284
Figure pat00284

[화학식1086] [화학식1087] [화학식1088] [화학식1089][Formula 1086] [Formula 1087] [Formula 1088] [Formula 1089]

Figure pat00285
Figure pat00285

[화학식1090] [화학식1091] [화학식1092] [화학식1093][Formula 1090] [Formula 1091] [Formula 1092] [Formula 1093]

Figure pat00286
Figure pat00286

[화학식1094] [화학식1095] [화학식1096] [화학식1097][Formula 1094] [Formula 1095] [Formula 1096] [Formula 1097]

Figure pat00287
Figure pat00287

[화학식1098] [화학식1099] [화학식1100] [화학식1101][Formula 1098] [Formula 1099] [Formula 1100] [Formula 1101]

Figure pat00288
Figure pat00288

[화학식1102] [화학식1103] [화학식1104] [화학식1105][Formula 1102] [Formula 1103] [Formula 1104] [Formula 1105]

Figure pat00289
Figure pat00289

[화학식1106] [화학식1107] [화학식1108] [화학식1109][Formula 1106] [Formula 1107] [Formula 1108] [Formula 1109]

Figure pat00290
Figure pat00290

[화학식1110] [화학식1111] [화학식1112] [화학식1113][Formula 1110] [Formula 1111] [Formula 1112] [Formula 1113]

Figure pat00291
Figure pat00291

[화학식1114] [화학식1115] [화학식1116] [화학식1117][Formula 1114] [Formula 1115] [Formula 1116] [Formula 1117]

Figure pat00292
Figure pat00292

[화학식1118] [화학식1119] [화학식1120] [화학식1121][Formula 1118] [Formula 1119] [Formula 1120] [Formula 1121]

Figure pat00293
Figure pat00293

[화학식1122] [화학식1123] [화학식1124] [화학식1125][Formula 1122] [Formula 1123] [Formula 1124] [Formula 1125]

Figure pat00294
Figure pat00294

[화학식1126] [화학식1127] [화학식1128] [화학식1129][Formula 1126] [Formula 1127] [Formula 1128] [Formula 1129]

Figure pat00295
Figure pat00295

[화학식1130] [화학식1131] [화학식1132] [화학식1133][Formula 1130] [Formula 1131] [Formula 1132] [Formula 1333]

Figure pat00296
Figure pat00296

[화학식1134] [화학식1135] [화학식1136] [화학식1137][Formula 1134] [Formula 1135] [Formula 1136] [Formula 1137]

Figure pat00297
Figure pat00297

[화학식1138] [화학식1139] [화학식1140] [화학식1141][Formula 1138] [Formula 1139] [Formula 1140] [Formula 1141]

Figure pat00298
Figure pat00298

[화학식1142] [화학식1143] [화학식1144] [화학식1145][Formula 1142] [Formula 1143] [Formula 1144] [Formula 1145]

Figure pat00299
Figure pat00299

[화학식1146] [화학식1147] [화학식1148] [화학식1149][Formula 1146] [Formula 1147] [Formula 1148] [Formula 1149]

Figure pat00300
Figure pat00300

[화학식1150] [화학식1151] [화학식1152] [화학식1153][Formula 1150] [Formula 1151] [Formula 1152] [Formula 1153]

Figure pat00301
Figure pat00301

[화학식1154] [화학식1155] [화학식1156] [화학식1157][Formula 1154] [Formula 1155] [Formula 1156] [Formula 1157]

Figure pat00302
Figure pat00302

[화학식1158] [화학식1159] [화학식1160] [화학식1161][Formula 1158] [Formula 1159] [Formula 1160] [Formula 1161]

Figure pat00303
Figure pat00303

[화학식1162] [화학식1163] [화학식1164] [화학식1165][Formula 1162] [Formula 1163] [Formula 1164] [Formula 1165]

Figure pat00304
Figure pat00304

[화학식1166] [화학식1167] [화학식1168] [화학식1169][Formula 1166] [Formula 1167] [Formula 1168] [Formula 1169]

Figure pat00305
Figure pat00305

[화학식1170] [화학식1171] [화학식1172] [화학식1173][Formula 1170] [Formula 1171] [Formula 1172] [Formula 1173]

Figure pat00306
Figure pat00306

[화학식1174] [화학식1175] [화학식1176] [화학식1177][Formula 1174] [Formula 1175] [Formula 1176] [Formula 1177]

Figure pat00307
Figure pat00307

[화학식1178] [화학식1179] [화학식1180] [화학식1181][Formula 1178] [Formula 1179] [Formula 1180] [Formula 1181]

Figure pat00308
Figure pat00308

[화학식1182] [화학식1183] [화학식1184] [화학식1185][Formula 1182] [Formula 1183] [Formula 1184] [Formula 1185]

Figure pat00309
Figure pat00309

[화학식1186] [화학식1187] [화학식1188] [화학식1189][Formula 1186] [Formula 1187] [Formula 1188] [Formula 1189]

Figure pat00310
Figure pat00310

[화학식1190] [화학식1191] [화학식1192] [화학식1193][Formula 1190] [Formula 1191] [Formula 1192] [Formula 1193]

Figure pat00311
Figure pat00311

[화학식1194] [화학식1195] [화학식1196] [화학식1197][Formula 1194] [Formula 1195] [Formula 1196] [Formula 1197]

Figure pat00312
Figure pat00312

[화학식1198] [화학식1199] [화학식1200] [화학식1201][Formula 1198] [Formula 1199] [Formula 1200] [Formula 1201]

Figure pat00313
Figure pat00313

[화학식1202] [화학식1203] [화학식1204] [화학식1205][Formula 1202] [Formula 1203] [Formula 1204] [Formula 1205]

Figure pat00314
Figure pat00314

[화학식1206] [화학식1207] [화학식1208] [화학식1209][Formula 1206] [Formula 1207] [Formula 1208] [Formula 1209]

Figure pat00315
Figure pat00315

[화학식1210] [화학식1211] [화학식1212] [화학식1213][Formula 1210] [Formula 1211] [Formula 1212] [Formula 1213]

Figure pat00316
Figure pat00316

[화학식1214] [화학식1215] [화학식1216] [화학식1217][Formula 1214] [Formula 1215] [Formula 1216] [Formula 1217]

Figure pat00317
Figure pat00317

[화학식1218] [화학식1219] [화학식1220] [화학식1221][Formula 1218] [Formula 1219] [Formula 1220] [Formula 1221]

Figure pat00318
Figure pat00318

[화학식1222] [화학식1223] [화학식1224] [화학식1225][Formula 1222] [Formula 1223] [Formula 1224] [Formula 1225]

Figure pat00319
Figure pat00319

[화학식1226] [화학식1227] [화학식1228] [화학식1229][Formula 1226] [Formula 1227] [Formula 1228] [Formula 1229]

Figure pat00320
Figure pat00320

[화학식1230] [화학식1231] [화학식1232] [화학식1233][Formula 1230] [Formula 1231] [Formula 1232] [Formula 1233]

Figure pat00321
Figure pat00321

[화학식1234] [화학식1235] [화학식1236] [화학식1237][Formula 1234] [Formula 1235] [Formula 1236] [Formula 1237]

Figure pat00322
Figure pat00322

[화학식1238] [화학식1239] [화학식1240] [화학식1241][Formula 1238] [Formula 1239] [Formula 1240] [Formula 1241]

Figure pat00323
Figure pat00323

[화학식1242] [화학식1243] [화학식1244] [화학식1245][Formula 1242] [Formula 1243] [Formula 1244] [Formula 1245]

Figure pat00324
Figure pat00324

[화학식1246] [화학식1247] [화학식1248] [화학식1249][Formula 1246] [Formula 1247] [Formula 1248] [Formula 1249]

Figure pat00325
Figure pat00325

[화학식1250] [화학식1251] [화학식1252] [화학식1253][Formula 1250] [Formula 1251] [Formula 1252] [Formula 1253]

Figure pat00326
Figure pat00326

[화학식1254] [화학식1255] [화학식1256] [화학식1257][Formula 1254] [Formula 1255] [Formula 1256] [Formula 1257]

Figure pat00327
Figure pat00327

[화학식1258] [화학식1259] [화학식1260] [화학식1261][Formula 1258] [Formula 1259] [Formula 1260] [Formula 1261]

Figure pat00328
Figure pat00328

[화학식1262] [화학식1263] [화학식1264] [화학식1265][Formula 1262] [Formula 1263] [Formula 1264] [Formula 1265]

Figure pat00329

Figure pat00329

또한, 본 발명은 애노드; 캐소드; 및 상기 애노드 및 캐소드 사이에 개재되며, 상기 [화학식 1]로 표시되는 축합아릴 화합물을 포함하는 층을 구비한 유기전계 발광소자를 제공한다.In addition, the present invention is an anode; Cathode; And it is interposed between the anode and the cathode, and provides an organic EL device having a layer comprising a condensed aryl compound represented by the above [Formula 1].

이때, 상기 축합아릴 화합물이 함유된 층은 상기 애노드 및 캐소드 사이의 발광층인 것이 바람직하며, 애노드 및 캐소드 사이에는 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함할 수 있다.At this time, the layer containing the condensed aryl compound is preferably a light emitting layer between the anode and the cathode, and between the anode and the cathode as a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer It may further comprise one or more layers selected from the group consisting of.

구체적인 예로서, 정공수송층(HTL: Hole Transport Layer)이 추가로 적층되어 있고, 상기 캐소드와 상기 유기발광층 사이에 전자수송층(ETL: Electron Transport Layer)이 추가로 적층되어 있는 것일 수 있는데, 상기 정공수송층은 애노드로부터 정공을 주입하기 쉽게 하기 위하여 적층되는 것으로서, 상기 정공수송층의 재료로는 이온화 포텐셜이 작은 전자공여성 분자가 사용되는데, 주로 트리페닐아민을 기본 골격으로 하는 디아민, 트리아민 또는 테트라아민 유도체가 많이 사용되고 있다.As a specific example, a hole transport layer (HTL) may be further stacked, and an electron transport layer (ETL) may be further stacked between the cathode and the organic light emitting layer. The silver is stacked to facilitate the injection of holes from the anode, and the electron transport molecule having a small ionization potential is used as the material of the hole transport layer. A diamine, triamine or tetraamine derivative mainly based on triphenylamine is used. It is used a lot.

본 발명에서도 상기 정공수송층의 재료로서 당업계에 통상적으로 사용되는 것인 한 특별히 제한되지 않으며, 예를 들어, N,N'-비스(3-메틸페닐)-N,N'-디페닐-[1,1-비페닐]-4,4'-디아민(TPD) 또는 N,N'-디(나프탈렌-1-일)-N,N'-디페닐 벤지딘(a-NPD) 등을 사용할 수 있다.The present invention is not particularly limited as long as it is commonly used in the art as a material of the hole transport layer. For example, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1 , 1-biphenyl] -4,4'-diamine (TPD) or N, N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine (a-NPD) and the like can be used.

상기 정공수송층의 하부에는 정공주입층(HIL: Hole Injecting Layer)을 추가적으로 더 적층할 수 있는데, 상기 정공주입층 재료 역시 당업계에서 통상적으로 사용되는 것인 한 특별히 제한되지 않고 사용할 수 있으며, 예를 들어 CuPc(copper phthalocyanine) 또는 스타버스트(Starburst)형 아민류인 TCTA (4,4',4"-tri(N-carbazolyl) triphenyl-amine), m-MTDATA(4,4',4"-tris-(3-methylphenylphenyl amino)triphenylamine) 등을 사용할 수 있다.A hole injection layer (HIL) may be further stacked on the lower portion of the hole transport layer. The hole injection layer material may also be used without particular limitation as long as it is commonly used in the art. TCP (4,4 ', 4 "-tri (N-carbazolyl) triphenyl-amine), for example, copper phthalocyanine (CuPc) or starburst amines, m-MTDATA (4,4', 4" -tris- (3-methylphenylphenyl amino) triphenylamine) may be used.

또한, 본 발명에 따른 유기전계발광소자에 사용되는 상기 전자수송층은 캐소드로부터 공급된 전자를 유기발광층으로 원활히 수송하고 상기 유기발광층에서 결합하지 못한 정공의 이동을 억제함으로써 발광층 내에서 재결합할 수 있는 기회를 증가시키는 역할을 한다. 상기 전자수송층 재료로는 당 기술분야에서 통상적으로 사용되는 것이면 특별히 제한되지 않고 사용할 수 있음은 물론이며, 예를 들어 옥사디아졸 유도체인 PBD, BMD, BND 또는 Alq3 등을 사용할 수 있다.In addition, the electron transport layer used in the organic electroluminescent device according to the present invention has the opportunity to recombine in the light emitting layer by smoothly transporting the electrons supplied from the cathode to the organic light emitting layer and suppressing the movement of holes not bonded in the organic light emitting layer. Serves to increase. The electron transport layer material may be used without particular limitation as long as it is commonly used in the art, and for example, oxadiazole derivatives such as PBD, BMD, BND or Alq 3 may be used.

한편, 상기 전자수송층의 상부에는 캐소드로부터의 전자 주입을 용이하게 해주어 궁극적으로 파워효율을 개선 시키는 기능을 수행하는 전자주입층(EIL: Electron Injecting Layer)을 더 적층시킬 수도 있는데, 상기 전자주입층 재료 역시 당 기술분야에서 통상적으로 사용되는 것이면 특별한 제한없이 사용할 수 있으며, 예를 들어, LiF, NaCl, CsF, Li2O, BaO 등의 물질을 이용할 수 있다.Meanwhile, an electron injection layer (EIL) may be further stacked on the electron transport layer to facilitate electron injection from the cathode and ultimately improve power efficiency. Also commonly used in the art may be used without particular limitation, for example, it may be used a material such as LiF, NaCl, CsF, Li 2 O, BaO.

본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자 등에 사용될 수 있다.The organic light emitting display device according to the present invention can be used for a display device, a display device and a monochrome or white lighting device.

도 1은 본 발명의 유기전계발광소자의 구조를 나타내는 단면도이다. 본 발명에 따른 유기전계발광소자는 애노드(20), 정공수송층(40), 유기발광층(50), 전자수송층(60) 및 캐소드(80)을 포함하며, 필요에 따라 정공주입층(30)과 전자주입층(70)을 더 포함할 수 있으며, 그 이외에도 1층 또는 2층의 중간층을 더 형성하는 것도 가능하며, 정공저지층 또는 전자저지층을 더 형성시킬 수도 있다.1 is a cross-sectional view showing the structure of an organic light emitting display device according to the present invention. The organic light emitting device according to the present invention includes an anode 20, a hole transport layer 40, an organic light emitting layer 50, an electron transport layer 60 and a cathode 80, and if necessary, the hole injection layer 30 and The electron injection layer 70 may be further included. In addition, an intermediate layer of one or two layers may be further formed, and a hole blocking layer or an electron blocking layer may be further formed.

도 1을 참조하여 본 발명의 유기전계발광소자 및 그 제조방법에 대하여 살펴보면, 다음과 같다. 먼저 기판(10) 상부에 애노드 전극용 물질을 코팅하여 애노드(20)를 형성한다. 여기에서 기판(10)으로는 통상적인 유기 EL 소자에서 사용되는 기판을 사용하는데 투명성, 표면 평활성, 취급용이성 및 방수성이 우수한 유기 기판 또는 투명 플라스틱 기판이 바람직하다. 그리고, 애노드 전극용 물질로는 투명하고 전도성이 우수한 산화인듐주석(ITO), 산화인듐아연(IZO), 산화주석(SnO2), 산화아연(ZnO) 등을 사용한다.Referring to Figure 1 with respect to the organic light emitting device and a manufacturing method of the present invention, as follows. First, the anode 20 is formed by coating an anode electrode material on the substrate 10. As the substrate 10, a substrate used in a conventional organic EL device is used. An organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, ease of handling, and waterproofness is preferable. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity are used.

상기 애노드(20) 전극 상부에 정공 주입층 물질을 진공열 증착, 또는 스핀 코팅하여 정공주입층(30)을 형성한다. 그 다음으로 상기 정공주입층(30)의 상부에 정공수송층 물질을 진공 열증착 또는 스핀 코팅하여 정공수송층(40)을 형성한다. 이어서, 상기 정공수송층(40)의 상부에 유기발광층(50)을 적층하고 상기 유기발광층(50)의 상부에 선택적으로 정공저지층(미도시)을 진공 증착 방법, 또는 스핀 코팅 방법으로서 박막을 형성할 수 있다. 상기 정공저지층은 정공이 유기발광층을 통과하여 캐소드로 유입되는 경우에는 소자의 수명과 효율이 감소되기 때문에 HOMO(Highest Occupied Molecular Orbital) 레벨이 매우 낮은 물질을 사용함으로써 이러한 문제를 방지하는 역할을 한다. 이 때, 사용되는 정공 저지 물질은 특별히 제한되지는 않으나 전자수송능력을 가지면서 발광 화합물보다 높은 이온화 포텐셜을 가져야 하며 대표적으로 BAlq, BCP, TPBI 등이 사용될 수 있다.The hole injection layer 30 is formed by vacuum-heat deposition or spin coating of the hole injection layer material on the anode 20 electrode. Next, the hole transport layer 40 is formed by vacuum thermal evaporation or spin coating of the hole transport layer material on the hole injection layer 30. Subsequently, the organic light emitting layer 50 is stacked on the hole transport layer 40, and a hole blocking layer (not shown) is selectively formed on the organic light emitting layer 50 by a vacuum deposition method or a spin coating method. can do. The hole blocking layer prevents such a problem by using a material having a very low highest Occupied Molecular Orbital (HOMO) level because when the hole is introduced into the cathode through the organic light emitting layer is reduced the lifetime and efficiency of the device. . In this case, the hole blocking material to be used is not particularly limited, but should have an ionization potential higher than the light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, and the like may be used.

이러한 정공저지층 위에 전자수송층(60)을 진공 증착 방법, 또는 스핀 코팅 방법을 통해 증착한 후에 전자주입층(70)을 형성하고 상기 전자주입층(70)의 상부에 캐소드 형성용 금속을 진공 열증착하여 캐소드(80) 전극을 형성함으로써 유기 EL 소자가 완성된다. 여기에서 캐소드 형성용 금속으로는 리튬(Li), 마그네슘(Mg), 알루미늄(Al), 알루미늄-리듐(Al-Li), 칼슘(Ca), 마그네슘-인듐(Mg-In), 마그네슘-은(Mg-Ag) 등을 사용할 수 있으며, 전면 발광 소자를 얻기 위해서는 ITO, IZO를 사용한 투과형 캐소드를 사용할 수 있다.After the electron transport layer 60 is deposited on the hole blocking layer through a vacuum deposition method or a spin coating method, an electron injection layer 70 is formed and a cathode forming metal is vacuum-heated on the electron injection layer 70. The organic EL device is completed by vapor deposition to form a cathode 80 electrode. The metal for forming the cathode may be lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lidium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag), and the like, and a transmissive cathode using ITO and IZO can be used to obtain a front light emitting device.

또한, 본 발명의 다른 일 실시예에 의하면, 상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성될 수 있으며, 본 발명에 따른 유기전계발광소자는 표시소자, 디스플레이 소자 및 단색 또는 백색 조명용 소자에 사용될 수 있다.
According to another embodiment of the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is a single molecule deposition method or a solution process The organic light emitting display device according to the present invention may be used in display devices, display devices, and monochrome or white lighting devices.

이하, 바람직한 실시예를 들어 본 발명을 더욱 상세하게 설명한다. 그러나, 이들 실시예는 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 범위가 이에 의하여 제한되지 않는다는 것은 당업계의 통상의 지식을 가진 자에게 자명할 것이다.
Hereinafter, the present invention will be described in more detail with reference to preferred embodiments. It will be apparent, however, to those skilled in the art that these embodiments are for further explanation of the present invention and that the scope of the present invention is not limited thereby.

<실시예><Examples>

합성예 1. [화학식 52]의 합성Synthesis Example 1. Synthesis of [Formula 52]

1-(1) 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌의 합성Synthesis of 1- (1) 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl-9H-fluorene

Figure pat00330
Figure pat00330

1 L 둥근바닥플라스크에 2-브로모-9,9-다이페닐-9H-플루오렌-7-보론산 21.0 g (48 mmol), 2,5-다이브로모나이트로벤젠 16 g(57 mmol), 탄산칼슘 13.2 g(95 mmol), 테트라하이드로퓨란 126 mL, 다이옥산 42 mL, 물 126 mL를 넣고 교반하였다. 질소 분위기에서 반응액에 테트라키스(트리페닐포스핀)팔라듐(0) 1.1 g(1 mmol)을 넣고 환류시켰다. 반응 종료 후 상온으로 냉각시켰다. 냉각 후 EA/H2O로 추출하고 유기층을 모아 농축한뒤 컬럼 분리하였다. 분리액을 MC/MeOH로 재결정하고 결정을 감압하여 건조하였다.(9.1 g, 32%)
21.0 g (48 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene-7-boronic acid in a 1 L round bottom flask, 16 g (57 mmol) of 2,5-dibromonitetrobenzene, 13.2 g (95 mmol) of calcium carbonate, 126 mL of tetrahydrofuran, 42 mL of dioxane and 126 mL of water were added and stirred. 1.1 g (1 mmol) of tetrakis (triphenylphosphine) palladium (0) was added to the reaction solution under nitrogen atmosphere and refluxed. After the reaction was completed, the mixture was cooled to room temperature. After cooling, the mixture was extracted with EA / H 2 O, and the organic layers were collected, concentrated, and separated by column. The separation solution was recrystallized with MC / MeOH and the crystals were dried under reduced pressure (9.1 g, 32%).

1-(2) 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린의 합성Synthesis of 1- (2) 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluorene-2-yl) aniline

Figure pat00331
Figure pat00331

2 L 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌 9.1 g(15 mmol), 에탄올 182 mL, 염산 220 mL를 넣고 온도를 0 ℃ 이하로 냉각한 다음 틴 파우더 4.5 g(38 mmol)을 조금씩 넣은 후 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌이 완전히 녹을 때까지 가열하고 TLC로 반응 종료를 확인하고 40% 수산화나트륨 용액을 넣어 PH 10 이상으로 만들고 EA/H2O로 추출한 뒤 유기층을 취해 농축하고 MeOH로 재결정하고 결정을 감압 건조하였다(5.5 g, 63.6%)
9.1 g (15 mmol) of 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl-9H-fluorene in a 2 L round bottom flask, 182 mL of ethanol, 220 hydrochloric acid Add mL, cool the temperature below 0 ° C, add 4.5 g (38 mmol) of tin powder in small portions, and add 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl Heat until -9H-fluorene is completely dissolved, confirm the end of reaction by TLC, add 40% sodium hydroxide solution to PH 10 or higher, extract with EA / H2O, extract organic layer, concentrate and recrystallize with MeOH, and dry the crystals under reduced pressure. (5.5 g, 63.6%)

1-(3) 2-브로모-7-(4-브로모-2-아이오도페닐)-9,9-다이페닐-9H-플루오렌의 합성Synthesis of 1- (3) 2-bromo-7- (4-bromo-2-iodophenyl) -9,9-diphenyl-9H-fluorene

Figure pat00332
Figure pat00332

250 mL 둥근바닥플라스크에 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린 5.5 g(10 mmol), 소듐나이트라이트 1.7 g(24 mmol), 포타슘 아이오다이드 4.02 g(24.2 mmol)을 넣고 교반하면서 온도를 0 ℃ 이하로 내리고 염산을 천천히 떨어뜨린 후 반응을 종료하고 온도를 상온으로 올리고 물을 넣고 교반한 다음 다이메틸클로라이드(MC)를 넣고 교반해준 뒤 소듐 사이오설페이트를 반응액이 노란색으로 될 때까지 첨가해주고 MC/H2O로 추출하고 유기층을 농축해 컬럼 분리하고 분리액을 농축해 헥산으로 재결정하고 생성된 결정을 감압 건조하였다.(5 g, 76%)
5.5 g (10 mmol) of 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluorene-2-yl) aniline in a 250 mL round bottom flask, 1.7 g (24 mmol) of sodium nitrite mmol) and 4.02 g (24.2 mmol) of potassium iodide were added while stirring and the temperature was lowered to 0 ° C. or lower, and hydrochloric acid was slowly dropped. The reaction was terminated. The temperature was raised to room temperature, water was added, followed by stirring. After stirring), sodium thiosulphate was added until the reaction solution turned yellow, extracted with MC / H2O, the organic layer was concentrated and separated by column, the separated solution was concentrated and recrystallized with hexane, and the resulting crystal was dried under reduced pressure. (5 g, 76%)

1-(4) 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌 의 합성Synthesis of 1- (4) 2-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-fluorene

Figure pat00333
Figure pat00333

100 mL 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-아이오도페닐)-9,9-다이페닐-9H-플루오렌 5 g(7 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.2 g(0.15 mmol), 코퍼(I)아이오다이드 0.1 g(0.36 mmol), 트리에틸아민 200 mL를 넣고 상온에서 서서히 교반하면서 페닐아세틸렌 0.8 mL(7 mmol)을 천천히 떨어뜨렸다. 약 1 시간 동안 교반하고 헥산을 부어 반응을 종료하였다. 반응액을 농축해서 컬럼 분리하고 분리액을 농축한 뒤 재결정하고 결정을 감압 건조하였다.(3.8 g, 79.3%)
5 g (7 mmol) of 2-bromo-7- (4-bromo-2-iodophenyl) -9,9-diphenyl-9H-fluorene in a 100 mL round bottom flask, tetrakis (triphenylforce) Pin) palladium (0) 0.2 g (0.15 mmol), copper (I) iodide 0.1 g (0.36 mmol), 200 mL of triethylamine and slowly stirred at room temperature, slowly dropping 0.8 mL (7 mmol) of phenylacetylene. Knocked down. The reaction was stirred for about 1 hour and hexane was poured out. The reaction mixture was concentrated and separated by column, the separated solution was concentrated, recrystallized, and the crystals were dried under reduced pressure (3.8 g, 79.3%).

1-(5) 3,10-다이브로모-6,12,12-트리페닐-12H-인데노[1,2-b]페난스렌의 합성Synthesis of 1- (5) 3,10-Dibromo-6,12,12-triphenyl-12H-indeno [1,2-b] phenanthrene

Figure pat00334
Figure pat00334

500 mL 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌 3.8 g(6 mmol), 아이론(III)트라이플루오로메탄설포네이트 0.3 g(1 mmol), 1,2-다이클로로에탄 300 mL를 넣고 24 시간 동안 환류시켰다. 반응종료 후 반응액을 식히고 컬럼 분리하고 분리액을 농축해 MC/MeOH로 재결정하고, 생성된 결정을 여과해서 건조하였다.(3.4 g, 89.5%)
3.8 g (6 mmol) of 2-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-fluorene in a 500 mL round bottom flask, iron (III) 0.3 g (1 mmol) of trifluoromethanesulfonate and 300 mL of 1,2-dichloroethane were added and refluxed for 24 hours. After completion of the reaction, the reaction solution was cooled, separated by column, concentrated solution was recrystallized with MC / MeOH, and the resulting crystals were filtered and dried. (3.4 g, 89.5%)

1-(6) [화학식 52]의 합성Synthesis of 1- (6)

Figure pat00335
Figure pat00335

250 mL 둥근바닥 플라스크에 3,10-다이브로모-6,12,12-트리페닐-12H-인데노[1,2-b]페난스렌 3.4 g(5 mmol), bis(4-tert-부틸페닐)아닐린 3.5 g(13 mmol), 팔라듐(II)아세테이트 0.05 g(0.2 mmol), 소듐-t-부톡사이드 2.0 g(21 mmol), 톨루엔 50 mL를 넣고 교반하면서 가열하였다. 온도가 60 ℃가 되면 트리-t-부틸포스핀 을 넣고 온도를 더 높여 환류시켰다. 반응이 종료되면 반응액을 식히고 컬럼 분리하였다. 분리액을 농축해 재결정하고 결정을 테트라하이드로퓨란에 녹여 아세톤으로 다시 재결정하였다. 같은 방법으로 6 회 이상 재결정하였다.(2.6 g, 47.4%)
In a 250 mL round bottom flask, 3.4 g (5 mmol) of 3,10-dibromo-6,12,12-triphenyl-12H-indeno [1,2-b] phenanthrene, bis (4-tert-butylphenyl 3.5 g (13 mmol) of aniline, 0.05 g (0.2 mmol) of palladium (II) acetate, 2.0 g (21 mmol) of sodium-t-butoxide, and 50 mL of toluene were added and heated with stirring. When the temperature was 60 ℃ tri-t- butylphosphine was added and the temperature was further raised to reflux. After the reaction was completed, the reaction solution was cooled and separated by column. The separated solution was concentrated and recrystallized, and the crystals were dissolved in tetrahydrofuran and recrystallized again with acetone. Recrystallized six more times in the same manner (2.6 g, 47.4%).

합성예 2. [화학식 64]의 합성Synthesis Example 2 Synthesis of [Formula 64]

1-(7)1- (7)

Figure pat00336
Figure pat00336

상기 [화학식 52]의 합성방법과 동일한 방법으로 bis(4-tert-부틸페닐)아닐린 대신 4-tert-부틸-N-p-(페닐-D5)아닐린 2.9 g(13 mmol)을 사용해 [화학식 64] 를 합성하였다. (2.3 g, 46.4%)
2.9 g (13 mmol) of 4-tert-butyl-Np- (phenyl-D5) aniline in place of bis (4-tert-butylphenyl) aniline in the same manner as in the synthesis method of [Formula 52] was used Synthesized. (2.3 g, 46.4%)

합성예 3. [화학식 101]의 합성Synthesis Example 3 Synthesis of [Formula 101]

2-(1) 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌 의 합성Synthesis of 2- (1) 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl-9H-fluorene

Figure pat00337
Figure pat00337

1 L 둥근바닥플라스크에 2-브로모-9,9-다이페닐-9H-플루오렌-7-보론산21.0 g(48 mmol), 2,5-다이브로모나이트로벤젠 16 g(57 mmol), 탄산칼슘 13.2 g(95 mmol), 테트라하이드로퓨란 126 mL, 다이옥산 42 mL, 물 126 mL를 넣고 교반하였다. 질소 분위기에서 반응액에 테트라키스(트리페닐포스핀)팔라듐(0) 1.1 g(1 mmol)을 넣고 환류시켰다. 반응 종료 후 상온으로 냉각시켰다. 냉각 후 EA/H2O로 추출하고 유기층을 모아 농축한 뒤 컬럼 분리하였다. 분리액을 MeOH로 재결정하고 결정을 감압하여 건조하였다.(9.1 g, 32%)
21.0 g (48 mmol) of 2-bromo-9,9-diphenyl-9H-fluorene-7-boronic acid in a 1 L round bottom flask, 16 g (57 mmol) of 2,5-dibromonitetrobenzene, 13.2 g (95 mmol) of calcium carbonate, 126 mL of tetrahydrofuran, 42 mL of dioxane and 126 mL of water were added and stirred. 1.1 g (1 mmol) of tetrakis (triphenylphosphine) palladium (0) was added to the reaction solution under nitrogen atmosphere and refluxed. After the reaction was completed, the mixture was cooled to room temperature. After cooling, the mixture was extracted with EA / H 2 O, and the organic layers were collected, concentrated, and separated by column. The separated solution was recrystallized from MeOH and the crystals were dried under reduced pressure (9.1 g, 32%).

2-(2) 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린의 합성Synthesis of 2- (2) 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluorene-2-yl) aniline

Figure pat00338
Figure pat00338

2 L 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌 9.1 g(15 mmol) 에탄올 182 mL, 염산 220 mL를 넣고 온도를 0 ℃ 이하로 냉각한 다음 틴 파우더 4.5 g(38 mmol)을 조금씩 넣은 후 2-브로모-7-(4-브로모-2-나이트로페닐)-9,9-다이페닐-9H-플루오렌이 완전히 녹을 때까지 가열하고 반응이 종결되면 40% 수산화나트륨 용액을 넣어 PH 10 이상으로 만들고 EA/H2O로 추출한 뒤 유기층을 취해 농축하고 MeOH로 재결정하고 결정을 감압 건조하였다.(5.5 g, 63.6%)
2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl-9H-fluorene 9.1 g (15 mmol) ethanol 182 mL, 220 mL hydrochloric acid in a 2 L round bottom flask After cooling the temperature to 0 ° C or less, 4.5 g (38 mmol) of tin powder was added little by little, followed by 2-bromo-7- (4-bromo-2-nitrophenyl) -9,9-diphenyl- Heat until 9H-fluorene is completely dissolved, and when the reaction is complete, add 40% sodium hydroxide solution to make PH 10 or more, extract with EA / H2O, extract the organic layer, recrystallize with MeOH, and dry the crystals under reduced pressure (5.5). g, 63.6%)

2-(3) 2-브로모-7-(4-브로모-2-아이오도페닐)-9,9-다이페닐-9H-플루오렌 의 합성Synthesis of 2- (3) 2-bromo-7- (4-bromo-2-iodophenyl) -9,9-diphenyl-9H-fluorene

Figure pat00339
Figure pat00339

250 mL 둥근바닥플라스크에 5-브로모-2-(7-브로모-9,9-다이페닐-9H-플루오렌-2-yl)아닐린 5.5 g(10 mmol), 소듐나이트라이트 1.7 g(24 mmol), 포타슘 아이오다이드 4.02 g(24.2 mmol)을 넣고 교반하면서 온도를 0 ℃ 이하로 내리고 염산을 천천히 떨어뜨린 후 반응을 종료하고 온도를 상온으로 올리고 물을 넣고 교반하였다. 다이메틸클로라이드(MC)를 넣고 교반해준 뒤 소듐 사이오설페이트를 반응액이 노란색으로 될 때까지 첨가해주고 MC/H2O로 추출하고 유기층을 농축해 컬럼 분리 하고 분리액을 농축해 헥산으로 재결정하고 생성된 결정을 감압 건조하였다.(5 g, 76%)
5.5 g (10 mmol) of 5-bromo-2- (7-bromo-9,9-diphenyl-9H-fluorene-2-yl) aniline in a 250 mL round bottom flask, 1.7 g (24 mmol) of sodium nitrite mmol) and 4.02 g (24.2 mmol) of potassium iodide were added to the mixture, and the temperature was lowered to 0 ° C. or lower while hydrochloric acid was slowly dropped. The reaction was terminated, the temperature was raised to room temperature, and water was added and stirred. Add dimethyl chloride (MC) and stir, add sodium thiosulphate until the reaction solution turns yellow, extract with MC / H2O, concentrate the organic layer and separate the column, concentrate the separation solution, recrystallize with hexane, The crystals were dried under reduced pressure. (5 g, 76%)

2-(4) 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌의 합성Synthesis of 2- (4) 2-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-fluorene

Figure pat00340
Figure pat00340

100 mL 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-아이오도페닐)-9,9-다이페닐-9H-플루오렌 5 g(7 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.2 g(0.15 mmol), 코퍼(I)아이오다이드 0.1 g(0.36 mmol), 트리에틸아민 200 mL를 넣고 상온에서 서서히 교반하면서 페닐아세틸렌 0.8 mL(7 mmol)을 천천히 떨어뜨렸다. 약 1 시간 동안 교반하고 헥산을 부어 반응을 종료하였다. 반응액을 농축해서 컬럼 분리하고 분리액을 농축한 뒤 재결정하고 결정을 감압 건조하였다.(3.8 g, 79.3%)
5 g (7 mmol) of 2-bromo-7- (4-bromo-2-iodophenyl) -9,9-diphenyl-9H-fluorene in a 100 mL round bottom flask, tetrakis (triphenylforce) Pin) palladium (0) 0.2 g (0.15 mmol), copper (I) iodide 0.1 g (0.36 mmol), 200 mL of triethylamine and slowly stirred at room temperature, slowly dropping 0.8 mL (7 mmol) of phenylacetylene. Knocked down. The reaction was stirred for about 1 hour and hexane was poured out. The reaction mixture was concentrated and separated by column, the separated solution was concentrated, recrystallized, and the crystals were dried under reduced pressure (3.8 g, 79.3%).

2-(5) 7-(4-(다이페닐아미노)-2-(페닐에티닐)페닐)-N,N,9,9-테트라페닐-9H-플루오렌-2-아민의 합성Synthesis of 2- (5) 7- (4- (diphenylamino) -2- (phenylethynyl) phenyl) -N, N, 9,9-tetraphenyl-9H-fluoren-2-amine

Figure pat00341
Figure pat00341

250 mL 둥근바닥플라스크에 브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌 3.4 g(5 mmol), 다이페닐아민 2.1 g(13 mmol), 팔라듐(II)아세테이트 0.05 g(0.2 mmol), 소듐-t-부톡사이드 2.0 g(21 mmol), 톨루엔 50 mL를 넣고 가열해서 약 60 ℃가 되면 트리부틸포스핀을 넣고 환류시켰다. 반응을 종료하고 반응액을 상온으로 식히고 컬럼 분리하고 분리액을 농축해 재결정하고 결정을 건조하였다.(2.6 g, 60.2%)
In a 250 mL round bottom flask, 3.4 g (5 mmol) of bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-fluorene, 2.1 g of diphenylamine (13 mmol), 0.05 g (0.2 mmol) of palladium (II) acetate, 2.0 g (21 mmol) of sodium-t-butoxide, and 50 mL of toluene were added and heated to about 60 ° C. to tributylphosphine and refluxed. . After completion of the reaction, the reaction solution was cooled to room temperature, separated by column, the separated solution was concentrated and recrystallized, and the crystals were dried (2.6 g, 60.2%).

2-(6) 5-아이오도-N3,N3,N10,N10,6,12,12-헵타페닐-12H-인데노[1,2-b]페난스렌-3,10-다이아민의 합성Synthesis of 2- (6) 5-iodo-N3, N3, N10, N10,6,12,12-heptaphenyl-12H-indeno [1,2-b] phenanthrene-3,10-diamine

Figure pat00342
Figure pat00342

250 mL 둥근바닥플라스크에 7-(4-(다이페닐아미노)-2-(페닐에티닐)페닐)-N,N,9,9-테트라페닐-9H-플루오렌-2-아민 2.6 g(3 mmol)을 MC에 녹여 -78 ℃로 냉각하고 아이오딘모노클로라이드 4 mL를 천천히 떨어뜨렸다. 동일한 온도에서 1 시간 동안 교반하고 온도를 상온으로 올린 후 소듐바이설파이트 포화용액을 넣어 반응을 종료시키고 MC/H2O로 추출한 다음 유기층을 농축해서 결정을 석출하고 MeOH 슬러리 후 여과하고 건조하였다.(2.4 g, 92%)
2.6 g (3) of 7- (4- (diphenylamino) -2- (phenylethynyl) phenyl) -N, N, 9,9-tetraphenyl-9H-fluoren-2-amine in a 250 mL round bottom flask mmol) was dissolved in MC, cooled to -78 ° C, and 4 mL of iodine monochloride was slowly dropped. After stirring for 1 hour at the same temperature and raising the temperature to room temperature, the reaction was terminated by adding saturated sodium bisulfite solution, extracted with MC / H 2 O, and the organic layer was concentrated to precipitate crystals, filtered after MeOH slurry and dried. g, 92%)

2-(7) [화학식 101]의 합성Synthesis of 2- (7)

Figure pat00343
Figure pat00343

250 mL 둥근바닥플라스크에 5-아이오도-N3,N3,N10,N10,6,12,12-헵타페닐-12H-인데노[1,2-b]페난스렌-3,10-다이아민 2.4 g(3 mmol), 페닐보론산 0.4 g (3 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 0.1 g(0.1 mmol), 포타슘카보네이트 0.7 g(5 mmol), 테트라하이드로퓨란 14.4 mL, 다이옥산 4.8 mL, 물 14.4 mL를 넣고 온도를 올려 환류하면서 24 시간 반응시켰다. 반응이 종결된후 EA/H2O로 추출하고 유기층을 모아 농축하였다. 농축액을 컬럼 분리하고 분리액을 농축해 재결정하고 결정을 건조하였다. (1.8 g, 79.1%)
2.4 g of 5-iodo-N3, N3, N10, N10,6,12,12-heptaphenyl-12H-indeno [1,2-b] phenanthrene-3,10-diamine in 250 mL round bottom flask (3 mmol), phenylboronic acid 0.4 g (3 mmol), tetrakis (triphenylphosphine) palladium (0) 0.1 g (0.1 mmol), potassium carbonate 0.7 g (5 mmol), tetrahydrofuran 14.4 mL, dioxane 4.8 mL, 14.4 mL of water were added thereto, and the temperature was raised to reflux for 24 hours. After the reaction was completed, the mixture was extracted with EA / H 2 O, and the organic layers were collected and concentrated. The concentrated solution was separated by column, the separated solution was concentrated and recrystallized, and the crystals were dried. (1.8 g, 79.1%)

합성예 4. [화학식 105]의 합성Synthesis Example 4. Synthesis of Chemical Formula 105

2-(8)2- (8)

Figure pat00344
Figure pat00344

상기 합성예 2-(4)에서 합성한 2-브로모-7-(4-브로모-2-(페닐에티닐)페닐)-9,9-다이페닐-9H-플루오렌를 사용해 다이페닐아민 대신 4-(나프탈렌-1-yl-아미노)벤조나이트라일을 사용해 상기와 같은 방법으로 합성하였다.(1.5 g, 65.4%)
2-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) -9,9-diphenyl-9H-fluorene synthesized in Synthesis Example 2- (4) instead of diphenylamine Synthesis was carried out in the same manner as above using 4- (naphthalene-1-yl-amino) benzonitriyl (1.5 g, 65.4%).

합성예 5. [화학식 851]의 합성Synthesis Example 5. Synthesis of [Formula 851]

3-(1) 2-(7-브로모페난스렌-2-yl)-4,4,5,5-테트라메틸-1,3,2-다이옥사보로렌의 합성Synthesis of 3- (1) 2- (7-bromophenanthrene-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxabororene

Figure pat00345
Figure pat00345

1 L 둥근바닥 플라스크에 2,7-다이브로모페난스렌 22 g(65 mmol), Bis(피나콜라토)다이보론 18.8 g(74 mmol), PdCl2(dppf) 1.6 g(2 mmol), 포타슘아세테이트 20.6 g(210 mmol), 톨루엔 440 mL를 넣고 110 ℃ 정도로 가열해 환류시켰다. 반응이 종료되면 뷰흐너 깔때기에 셀라이트와 실리카겔을 깔고 뜨거운 톨루엔을 이용해 여과하였다. 여액을 농축하고 컬럼 분리한 후 분리액을 농축해 재결정하고 생성된 결정을 건조하였다.(18 g, 71.8%)
22 g (65 mmol) 2,7-dibromophenanthsene, 18.8 g (74 mmol) Bis (pinacolato) diboron, 1.6 g (2 mmol) PdCl2 (dppf), potassium acetate 20.6 in a 1 L round bottom flask g (210 mmol) and 440 mL of toluene were added thereto, and heated to reflux for 110 ° C. After the reaction was completed, Celite and silica gel was placed in a Buchner funnel and filtered using hot toluene. The filtrate was concentrated and column separated, then the separated liquid was concentrated and recrystallized, and the resulting crystals were dried (18 g, 71.8%).

3-(2) 2-브로모-7-(4-브로모-2-나이트로페닐)페난스렌의 합성Synthesis of 3- (2) 2-bromo-7- (4-bromo-2-nitrophenyl) phenanthsene

Figure pat00346
Figure pat00346

1 L 둥근바닥플라스크에2-(7-브로모페난스렌-2-yl)-4,4,5,5-테트라메틸-1,3,2-다이옥사보로렌 18 g(47 mmol), 2,5-다이브로모나이트로벤젠 14.5 g(52 mmol), PdCl2(dppf) 0.8 g(1 mmol), 소듐바이카보네이트 7.9 g(94 mmol), 테트라하이드로퓨란 360 mL, 물 180 mL를 넣고 환류하면서 반응시켰다. 반응이 종결되면 상온으로 냉각하고 EA/H2O로 추출해 유기층을 농축해서 컬럼 분리하였다. 분리액을 농축하고 재결정을 하고 생성된 결정을 여과해서 건조하였다.(14.3 g, 66.6%)
18 g (47 mmol) of 2- (7-bromophenanthren-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolene in a 1 L round bottom flask, 2, 14.5 g (52 mmol) of 5-dibromonitrobenzene, 0.8 g (1 mmol) of PdCl 2 (dppf), 7.9 g (94 mmol) of sodium bicarbonate, 360 mL of tetrahydrofuran and 180 mL of water were added and reacted under reflux. . After the reaction was completed, the mixture was cooled to room temperature, extracted with EA / H 2 O, and the organic layer was concentrated and separated by column. The separated solution was concentrated, recrystallized and the resulting crystals were filtered and dried (14.3 g, 66.6%).

3-(3) 3,10-다이브로모-12H-나프토[1,2-b]카바졸의 합성Synthesis of 3- (3) 3,10-Dibromo-12H-naphtho [1,2-b] carbazole

Figure pat00347
Figure pat00347

500 mL 둥근바닥플라스크에 2-브로모-7-(4-브로모-2-나이트로페닐)페난스렌 14.3 g(31 mmol), 트리페닐포스핀 20.5 g(78 mmol), 다이클로로벤젠 286 mL를 넣고 환류시켰다. 반응이 종결되면 뷰흐너 깔때기에 셀라이트와 실리카겔을 깔고 뜨거운 다이클로로벤젠을 이용해 여과하였다. 여액을 농축하고 재결정해서 생성된 결정을 건조하였다.(9.5 g, 71.6%)
In a 500 mL round bottom flask, 14.3 g (31 mmol) of 2-bromo-7- (4-bromo-2-nitrophenyl) phenanthrene, 20.5 g (78 mmol) of triphenylphosphine, 286 mL of dichlorobenzene Was added and refluxed. Upon completion of the reaction, the Buchner funnel was coated with celite and silica gel and filtered using hot dichlorobenzene. The filtrate was concentrated and recrystallized to dry the resulting crystals (9.5 g, 71.6%).

3-(4) 3,10-다이브로모-12-페닐-12H-나프토[1,2-b]카바졸의 합성Synthesis of 3- (4) 3,10-dibromo-12-phenyl-12H-naphtho [1,2-b] carbazole

Figure pat00348
Figure pat00348

250 mL 둥근바닥플라스크에 3,10-다이브로모-12H-나프토[1,2-b]카바졸 9.5 g(22 mmol), 아이오도벤젠 6.4 g(31 mmol), 코퍼파우더 2.14 g(33.6 mmol), 포타슘카보네이트 4.3 g(31 mmol), 18-크라운-6 1.78 g(6.7 mmol), 다이메틸설폭사이드 150 mL를 넣고 24 시간 동안 환류시켰다. 반응이 종결되면 MC/H2O로 추출하고 유기층을 모아 농축한 후 컬럼 분리하고 분리액을 농축하였다. (8.6 g, 76.6%)
9.5 g (22 mmol) of 3,10-dibromo-12H-naphtho [1,2-b] carbazole in a 250 mL round bottom flask, 6.4 g (31 mmol) of iodobenzene, 2.14 g (33.6 mmol) of copper powder ), 4.3 g (31 mmol) of potassium carbonate, 1.78 g (6.7 mmol) of 18-crown-6, and 150 mL of dimethyl sulfoxide were added and refluxed for 24 hours. After the reaction was completed, the mixture was extracted with MC / H 2 O, the organic layers were collected, concentrated, and column separated, and the separation solution was concentrated. (8.6 g, 76.6%)

3-(5) [화학식 843]의 합성Synthesis of 3- (5)

Figure pat00349
Figure pat00349

250 mL 둥근바닥플라스크에 3,10-다이브로모-12-페닐-12H-나프토[1,2-b]카바졸 8.6 g(17 mmol), N-(4-플루오로페닐)나프탈렌-2-아민 9.8 g(41 mmol), 팔라듐(II)아세테이트 0.15 g(0.7 mmol), 소듐-t-부톡사이드 6.6 g(69 mmol), 톨루엔100 mL를 넣고 가열하면서 교반하고 60 ℃가 되면 트리-t-부틸포스핀 1.1 mL(2.7 mmol)을 넣어주고 환류시켰다. 반응이 종결되면 상온으로 식히고 농축한 다음 컬럼 분리하고 분리액을 농축해 MeOH로 재결정하고 생성된 결정을 건조하였다. (6.8 g, 48.7%)
8.6 g (17 mmol) of 3,10-dibromo-12-phenyl-12H-naphtho [1,2-b] carbazole in a 250 mL round bottom flask, N- (4-fluorophenyl) naphthalene-2- Add 9.8 g (41 mmol) of amine, 0.15 g (0.7 mmol) of palladium (II) acetate, 6.6 g (69 mmol) of sodium-t-butoxide, and 100 mL of toluene and stir while heating. 1.1 mL (2.7 mmol) of butylphosphine was added and refluxed. After the reaction was completed, the mixture was cooled to room temperature, concentrated, separated by column, and the separated solution was concentrated, recrystallized with MeOH, and the resulting crystals were dried. (6.8 g, 48.7%)

3-(6) [화학식 851]의 합성Synthesis of 3- (6)

Figure pat00350
Figure pat00350

상기 합성예 3-(4)에서 합성한 3,10-다이브로모-12-페닐-12H-나프토[1,2-b]카바졸을 사용하고 N-(4-플루오로페닐)나프탈렌-2-아민 대신 다이페닐아민을 사용해 상기와 같은 방법으로 합성하였다.(5.8 g, 49.9%)
N- (4-fluorophenyl) naphthalene-2 using 3,10-dibromo-12-phenyl-12H-naphtho [1,2-b] carbazole synthesized in Synthesis Example 3- (4) above Diphenylamine was used instead of the amine, and was synthesized in the same manner as described above (5.8 g, 49.9%).

합성예 6. Synthesis Example 6.

4-(1) 7-브로모다이벤조[b,d]사이오펜-3-yl보론산의 합성Synthesis of 4- (1) 7-bromodibenzo [b, d] thiophen-3-ylboronic acid

Figure pat00351
Figure pat00351

2 L 둥근바닥 플라스크에 3,7-다이브로모벤조[b,d]사이오펜 50 g(146 mmol), 테트라하이드로퓨란 400 mL를 넣고 질소분위기에서 드라이아이스와 아세톤으로 -78 ℃로 냉각하였다. 온도를 유지하면서 1.6 M 부틸리튬 100.5 mL를 천천히 떨어뜨리고 나서 온도를 유지하면서 2 시간 동안 교반하였다. 동일한 온도에서 트리메틸보레이트 103 mL를 천천히 떨어뜨리고 나서 온도를 상온으로 올리고 24 시간 교반하였다. 반응이 종결된 후 2 N 염산을 넣고 교반하였다. 반응액에 EA를 넣어서 교반하고 EA/H2O로 추출한 후 EA층을 PH 6~7까지 중화하였다. 유기층을 농축하고 EA:Hexane=1:4 용액과 글래스필터로 불순물을 제거하고 EA:MEOH=10:1 용액으로 Main을 분리한다. 분리액을 농축하고 헥산으로 재결정하고, 생성된 결정을 건조하였다.(29.4 g, 65.5%)
50 g (146 mmol) of 3,7-dibromobenzo [b, d] thiophene and 400 mL of tetrahydrofuran were added to a 2 L round bottom flask, and the mixture was cooled to -78 ° C with dry ice and acetone in a nitrogen atmosphere. 100.5 mL of 1.6 M butyllithium was slowly dropped while maintaining the temperature, followed by stirring for 2 hours while maintaining the temperature. 103 mL of trimethyl borate was slowly dropped at the same temperature, and then the temperature was raised to room temperature and stirred for 24 hours. After the reaction was completed, 2N hydrochloric acid was added and stirred. EA was added to the reaction mixture, stirred and extracted with EA / H 2 O, and the EA layer was neutralized to PH 6-7. Concentrate the organic layer, remove impurities with EA: Hexane = 1: 4 solution and glass filter, and separate Main with EA: MEOH = 10: 1 solution. The separated solution was concentrated and recrystallized from hexane, and the resulting crystals were dried (29.4 g, 65.5%).

4-(2) 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜의 합성Synthesis of 4- (2) 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, d] thiophene

Figure pat00352
Figure pat00352

1 L 둥근바닥플라스크 에 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜 29.4 g(96 mmol), 2,5-다이브로모나이트로벤젠 32.3 g(115 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 2.2 g(1.9 mmol), 탄산칼륨 26.5 g(192 mmol), 테트라하이드로퓨란 176.4 mL, 다이옥산 58.8 mL, 물 176.4 mL를 넣고 환류시켰다. 반응을 종결하고 상온으로 식히고 EA/H2O로 추출하고 유기층을 농축한 다음 컬럼 분리하였다. 분리액을 농축하고 MeOH로 재결정하고 생성된 결정을 건조하였다.(28 g, 63.1%)
29.4 g (96 mmol) of 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, d] thiophene, 2,5-dibromonitrobenzene in a 1 L round bottom flask 32.3 g (115 mmol), tetrakis (triphenylphosphine) palladium (0) 2.2 g (1.9 mmol), potassium carbonate 26.5 g (192 mmol), 176.4 mL tetrahydrofuran, 58.8 mL dioxane, 176.4 mL water It was refluxed. The reaction was terminated, cooled to room temperature, extracted with EA / H 2 O, the organic layer was concentrated and column separated. The separation was concentrated, recrystallized from MeOH and the resulting crystals were dried (28 g, 63.1%).

4-(3) 5-브로모-2-(7-브로모다이벤조[b,d]사이오펜-3-yl)아닐린의 합성Synthesis of 4- (3) 5-bromo-2- (7-bromodibenzo [b, d] thiophen-3-yl) aniline

Figure pat00353
Figure pat00353

1 L 둥근바닥플라스크에 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜 28 g(60 mmol), 염산 170 mL, 에탄올 560 mL를 넣고 온도를 0 ℃ 이하로 내린 후 틴 파우더 17.9 g(151 mmol)를 조금씩 넣어주고 3-브로모-7-(4-브로모-2-나이트로페닐)다이벤조[b,d]사이오펜이 완전히 녹을 때까지 가열하였다. 반응이 종결되면 상온으로 식히고 40% 수산화나트륨 수용액을 넣어 PH 10 이상으로 만들었다. EA/H2O로 추출하고 유기층을 취해 농축하고 MeOH로 재결정하고 생성된 결정을 건조하였다.(23 g, 87.8%)
Into a 1 L round bottom flask, 28 g (60 mmol) of 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, d] thiophene, 170 mL of hydrochloric acid, and 560 mL of ethanol were added. After the temperature was lowered to 0 ° C., 17.9 g (151 mmol) of tin powder was added little by little, and 3-bromo-7- (4-bromo-2-nitrophenyl) dibenzo [b, d] thiophene was completely removed. Heat until dissolved. After the reaction was completed, the mixture was cooled to room temperature, and 40% sodium hydroxide solution was added to make the pH 10 or more. Extract with EA / H2O, take organic layer, concentrate, recrystallize with MeOH and dry the resulting crystals (23 g, 87.8%).

4-(4) 3-브로모-7-(4-브로모-2-아이오도페닐)다이벤조[b,d]사이오펜의 합성Synthesis of 4- (4) 3-bromo-7- (4-bromo-2-iodophenyl) dibenzo [b, d] thiophene

Figure pat00354
Figure pat00354

1 L 둥근바닥플라스크에 5-브로모-2-(7-브로모다이벤조[b,d]사이오펜-3-yl)아닐린 23 g(53 mmol), 소듐나이트라이트 9.2 g(133 mmol), 포타슘아이오다이드 22 g(132.7 mmol), 아세토나이트라일 228 mL를 넣고 교반하면서 온도를 0 ℃ 이하로 냉각하고 염산을 천천히 떨어뜨렸다. 반응이 종결되면 온도를 상온으로 올리고 물을 넣고 교반하고 추가로 MC를 넣어서 교반하였다. 소듐사이오설페이트를 반응액이 노란색이 될 때까지 넣어주었다. MC/H2O로 추출하고 MC층을 모아 농축한 후 컬럼 분리하고 분리액을 농축해 헥산으로 재결정하고 생성된 결정을 건조하였다.(25 g, 86.6%)
23 g (53 mmol) of 5-bromo-2- (7-bromodibenzo [b, d] thiophen-3-yl) aniline, 9.2 g (133 mmol) sodium potassium in a 1 L round bottom flask 22 g (132.7 mmol) of iodide and 228 mL of acetonitrile were added thereto, the temperature was cooled to 0 ° C. or lower while stirring, and hydrochloric acid was slowly dropped. After the reaction was completed, the temperature was raised to room temperature, water was added thereto, followed by stirring. Sodium thiosulfate was added until the reaction solution turned yellow. The mixture was extracted with MC / H 2 O, the MC layers were combined, concentrated, column separated, the separated solution was concentrated, recrystallized with hexane, and the resulting crystals were dried (25 g, 86.6%).

4-(5) 3-브로모-7-(4-브로모-2-(페닐에티닐)페닐)다이벤조[b,d]사이오펜의 합성Synthesis of 4- (5) 3-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) dibenzo [b, d] thiophene

Figure pat00355
Figure pat00355

500 mL 둥근바닥플라스크에 3-브로모-7-(4-브로모-2-아이오도페닐)다이벤조[b,d]사이오펜 25 g(46 mmol), 테트라키스(트리페닐포스핀)팔라듐(0) 1.1 g(1 mmol), 요오드화구리 0.4 g(2 mmol), 트리에틸아민 200 mL를 넣고 상온에서 교반g하였다. 서서히 교반하면서 페닐아세틸렌 4.7 mL(46 mmol)을 천천히 떨어뜨렸다. 1시간 동안 교반하고 헥산을 부어 반응을 종결하였다. 반응액을 농축하고 컬럼분리 하고 분리액을 농축해서 재결정하였다. 생성된 결정을 여과해서 건조하였다. (19 g, 79.7%)
25 g (46 mmol) of 3-bromo-7- (4-bromo-2-iodophenyl) dibenzo [b, d] thiophene, tetrakis (triphenylphosphine) palladium in 500 mL round bottom flask (0) 1.1 g (1 mmol), 0.4 g (2 mmol) of copper iodide, and 200 mL of triethylamine were added thereto, followed by stirring at room temperature. 4.7 mL (46 mmol) of phenylacetylene was slowly dropped with gentle stirring. Stirred for 1 hour and poured to hexanes to terminate the reaction. The reaction solution was concentrated, column separated, and the separation solution was concentrated and recrystallized. The resulting crystals were filtered off and dried. (19 g, 79.7%)

4-(6) 3,10-다이브로모-6-페닐벤조[d]페난스로[3,2-b]사이오펜의 합성Synthesis of 4- (6) 3,10-dibromo-6-phenylbenzo [d] phenanthro [3,2-b] thiophene

Figure pat00356
Figure pat00356

500 mL 둥근바닥플라스크에 3-브로모-7-(4-브로모-2-(페닐에티닐)페닐)다이벤조[b,d]사이오펜 19 g(37 mmol), 아이론(III) 트리플루오로메탄설포네이트 1.8 g(4 mmol), 1,2-다이클로로에탄 300 mL를 넣고 24 시간 동안 환류시켰다. 반응이 종결되면 상온으로 식히고 농축한 뒤 컬럼분리하고 분리액을 농축해서 MeOH로 재결정하고 생성된 결정을 건조하였다.(17 g, 89.5%)
19 g (37 mmol) of 3-bromo-7- (4-bromo-2- (phenylethynyl) phenyl) dibenzo [b, d] thiophene in a 500 mL round bottom flask, iron (III) trifluor 1.8 g (4 mmol) of romethanesulfonate and 300 mL of 1,2-dichloroethane were added thereto, and the mixture was refluxed for 24 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, concentrated, separated by column, the separated solution was concentrated, recrystallized with MeOH, and the resulting crystals were dried (17 g, 89.5%).

4-(7) [화학식 1258]의 합성4- (7) Synthesis of [Formula 1258]

Figure pat00357
Figure pat00357

500 mL 둥근바닥플라스크에 10-다이브로모-6-페닐벤조[d]페난스로[3,2-b]사이오펜 17 g(33 mmol), 다이페닐아민 13.3 g(79 mmol), 팔라듐(II)아세테이트 0.29 g(1.3 mmol), 소듐-t-부톡사이드 12.6 g(131 mmol), 톨루엔 200 mL를 넣고 교반하면서 가열하고 60 ℃가 되면 트리-t-부틸포스핀 2.12 g(5.2 mmol)을 넣고 환류시켰다. 반응이 종결되면 상온으로 식히고 반응액을 농축해 컬럼 분리하고 분리액을 농축해 재결정하고, 생성된 결정을 여과하고 건조하였다.(8.6 g, 37.7%)
In a 500 mL round bottom flask, 17 g (33 mmol) of 10-dibromo-6-phenylbenzo [d] phenanthro [3,2-b] thiophene, 13.3 g (79 mmol) diphenylamine, palladium (II) Add 0.29 g (1.3 mmol) of acetate, 12.6 g (131 mmol) of sodium-t-butoxide, 200 mL of toluene, heat with stirring, and add 2.12 g (5.2 mmol) of tri-t-butylphosphine at 60 ° C. I was. After the reaction was completed, the mixture was cooled to room temperature, the reaction solution was concentrated and separated by column separation. The separated solution was concentrated and recrystallized, and the resulting crystals were filtered and dried.

실시예Example

ITO 글래스의 발광면적이 2 mm × 2 mm 크기가 되도록 패터닝한 후 세정하였다. 상기 ITO 글래스를 진공 챔버에 장착한 후 베이스 압력이 1×10-7 torr가 되도록 한 후 상기 ITO 위에 CuPc(800Å), α-NPD(300Å) 순으로 성막한 후 본 발명에 따른 화합물(화학식 52, 64, 101, 105, 843, 851, 1258)을 성막(250Å)한 다음 Alq3 (350Å), LiF (5Å), Al (500Å)의 순서로 성막하여 유기전계발광소자를 제조하였다. 호스트물질은 [화학식 1267]화합물로 하였다.
The ITO glass was patterned to have a light emitting area of 2 mm x 2 mm and then cleaned. After mounting the ITO glass in a vacuum chamber and the base pressure is 1 × 10 -7 torr, and then deposited on the ITO in the order of CuPc (800 kPa), α-NPD (300 kPa) in order to the compound according to the invention (Formula 52) , 64, 101, 105, 843, 851, and 1258 were formed into a film (250 mW) and then formed in the order of Alq 3 (350 mW), LiF (5 mW) and Al (500 mW) to manufacture an organic light emitting display device. The host material was a compound of Formula 1267.

비교예Comparative example

상기 실시예와 동일하게 유기전계발광소자를 제조하고, 다만, 발광층의 게스트 화합물로서 하기 [화학식 1266]로 표시되는 피렌계 화합물을 사용하였다.An organic light emitting diode was manufactured in the same manner as in the above example, except that a pyrene-based compound represented by the following [Formula 1266] was used as a guest compound of the light emitting layer.

[화학시 1266] [화학식 1267][Chemical Time 1266] [Chemical Formula 1267]

Figure pat00358
Figure pat00359
Figure pat00358
Figure pat00359

본 발명에 따른 유기 발광 화합물을 포함한 유기전계발광소자와 상기 비교예에 따라 제조된 유기전계 발광소자에 대하여 전압, 전류밀도, 휘도, 색 좌표 및 수명을 측정하고 그 결과를 하기 [표 1]에 나타내었다. T97은 휘도가 초기휘도에 비해 97%로 감소되는데 소요되는 시간을 의미한다.The voltage, current density, luminance, color coordinates, and lifespan of the organic light emitting device including the organic light emitting compound according to the present invention and the organic light emitting device manufactured according to the comparative example were measured and the results are shown in the following [Table 1]. Indicated. T97 means the time taken for the luminance to decrease to 97% of the initial luminance.

전압Voltage 전류밀도(㎃/㎠)Current density (㎃ / ㎠) 휘도(Cd/㎡)Luminance (Cd / ㎡) CIExCIEx CIEyCIEy T97T97 화학식 52Formula 52 4.094.09 1010 505.4505.4 0.140.14 0.090.09 3535 화학식 64Formula 64 3.843.84 1010 770.3770.3 0.140.14 0.080.08 3131 화학식 101Formula 101 4.024.02 1010 787.7787.7 0.140.14 0.110.11 7474 화학식 105Formula 105 3.783.78 1010 840.3840.3 0.130.13 0.070.07 3333 화학식 843Formula 843 3.923.92 1010 513.8513.8 0.130.13 0.120.12 118118 화학식 851Formula 851 4.094.09 1010 740740 0.130.13 0.120.12 7070 화학식 1258Formula 1258 4.164.16 1010 810810 0.130.13 0.130.13 4848 비교예 1Comparative Example 1 5.15.1 1010 560560 0.140.14 0.170.17 2020

상기 [표1]의 결과로부터, 본 발명에 따른 유기 발광 화합물을 포함한 유기전계발광소자는 구동전압이 낮고, 발광효율이 우수한 특성을 보이므로 표시소자, 디스플레이 소자 및 조명 등에 유용하게 사용될 수 있음을 알 수 있다.From the results of Table 1, the organic light emitting device including the organic light emitting compound according to the present invention has a low driving voltage and excellent luminous efficiency, so that it can be usefully used for display devices, display devices and lighting. Able to know.

10 : 기판 20 : 애노드
30 : 정공주입층 40 : 정공수송층
50 : 유기발광층 60 : 전자수송층
70 : 전자주입층 80 : 캐소드10: substrate 20: anode
30: hole injection layer 40: hole transport layer
50: organic light emitting layer 60: electron transport layer
70: electron injection layer 80: cathode

Claims (10)

하기 [화학식 1]로 표시되는 축합아릴 화합물:
[화학식 1]
Figure pat00360

상기 [화학식 1]에서,
상기 X는 O, S, P, NR5, CR5R6 또는 SiR5R6이고, R1 내지 R6, A1, A2, B1 및 B2는 서로 동일하거나 상이하며,
상기 R1 내지 R6, A1, A2, B1 및 B2는 각각 독립적으로 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 히드록시기, 니트로기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군에서 선택되고,
상기 L1 및 L2는 화학결합 또는 2가의 연결기로서 치환 또는 비치환된 탄소수 1 내지 30의 알킬렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬렌기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기, 치환 또는 비치환된 탄소수 3 내지 50의 헤테로아릴렌기로 이루어진 군에서 선택된다.Condensed aryl compound represented by the following [Formula 1]:
[Formula 1]
Figure pat00360

In [Formula 1],
X is O, S, P, NR 5 , CR 5 R 6 or SiR 5 R 6 , R 1 to R 6 , A 1 , A 2 , B 1 and B 2 are the same as or different from each other,
R 1 to R 6 , A 1 , A 2 , B 1 and B 2 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted carbon group having 2 to 30 carbon atoms Alkenyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl groups having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted carbon atoms 6 To 30 aryloxy group, substituted or unsubstituted C1-C30 alkylthioxy group, substituted or unsubstituted C5-C30 arylthioxy group, substituted or unsubstituted C1-C30 alkylamine group, substituted Or an unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 50 carbon atoms having O, N or S as a hetero atom, substituted Or beach A substituted silicon group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a hydroxy group, a nitro group, a halogen group, an amide group and an ester group,
The L 1 and L 2 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenylene group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon atom 3 to 30 as a chemical bond or a divalent linking group. Is selected from the group consisting of a cycloalkylene group, a substituted or unsubstituted arylene group having 5 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 50 carbon atoms. 제 1 항에 있어서,
상기 [화학식 1]은 하기 [화학식 2] 내지 [화학식 49]로 표시되는 군에서 선택되는 어느 하나인 것을 특징으로 하는 축합아릴 화합물:
Figure pat00361

[화학식 2] [화학식 3]
Figure pat00362

[화학식 4] [화학식 5]
Figure pat00363

[화학식 6] [화학식 7]
Figure pat00364

[화학식 8] [화학식 9]
Figure pat00365

[화학식 10] [화학식 11]
Figure pat00366

[화학식 12] [화학식 13]
Figure pat00367

[화학식 14] [화학식 15]
Figure pat00368

[화학식 16] [화학식 17]
Figure pat00369

[화학식 18] [화학식 19]
Figure pat00370

[화학식 20] [화학식 21]
Figure pat00371

[화학식 22] [화학식 23]
Figure pat00372

[화학식 24] [화학식 25]
Figure pat00373

[화학식 26] [화학식 27]
Figure pat00374

[화학식 28] [화학식 29]
Figure pat00375

[화학식 30] [화학식 31]
Figure pat00376

[화학식 32] [화학식 33]
Figure pat00377

[화학식 34] [화학식 35]
Figure pat00378

[화학식 36] [화학식 37]
Figure pat00379

[화학식 38] [화학식 39]
Figure pat00380

[화학식 40] [화학식 41]
Figure pat00381

[화학식 42] [화학식 43]
Figure pat00382

[화학식 44] [화학식 45]
Figure pat00383

[화학식 46] [화학식 47]
Figure pat00384

[화학식 48] [화학식 49]
상기 [화학식 2] 내지 [화학식 49]에서,
상기 R1 내지 R6, A1, A2, B1, B2, L1 및 L2는 상기 [화학식 1]의 정의와 동일하다.The method of claim 1,
[Formula 1] is a condensed aryl compound, characterized in that any one selected from the group represented by the following [Formula 2] to [Formula 49]:
Figure pat00361

[Formula 2] [Formula 3]
Figure pat00362

[Formula 4] [Formula 5]
Figure pat00363

[Formula 6] [Formula 7]
Figure pat00364

[Formula 8] [Formula 9]
Figure pat00365

[Formula 10] [Formula 11]
Figure pat00366

[Formula 12] [Formula 13]
Figure pat00367

[Formula 14] [Formula 15]
Figure pat00368

[Formula 16] [Formula 17]
Figure pat00369

[Formula 18] [Formula 19]
Figure pat00370

[Formula 20] [Formula 21]
Figure pat00371

[Formula 22] [Formula 23]
Figure pat00372

[Formula 24] [Formula 25]
Figure pat00373

[Formula 26] [Formula 27]
Figure pat00374

[Formula 28] [Formula 29]
Figure pat00375

[Formula 30] [Formula 31]
Figure pat00376

[Formula 32] [Formula 33]
Figure pat00377

[Formula 34] [Formula 35]
Figure pat00378

[Formula 36] [Formula 37]
Figure pat00379

[Formula 38] [Formula 39]
Figure pat00380

[Formula 40] [Formula 41]
Figure pat00381

[Formula 42] [Formula 43]
Figure pat00382

[Formula 44] [Formula 45]
Figure pat00383

[Formula 46] [Formula 47]
Figure pat00384

[Formula 48] [Formula 49]
In [Formula 2] to [Formula 49],
The R 1 to R 6 , A 1 , A 2 , B 1 , B 2 , L 1 and L 2 are the same as the definition of [Formula 1]. 제 1 항에 있어서,
상기 R1 내지 R6, A1, A2, B1, B2, L1 및 L2는 수소 원자, 중수소 원자, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 30의 시클로알케닐기, 치환 또는 비치환된 탄소수 1 내지 30의 알콕시기, 치환 또는 비치환된 탄소수 6 내지 30의 아릴옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬티옥시기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴티옥시기, 치환 또는 비치환된 탄소수 1 내지 30의 알킬아민기, 치환 또는 비치환된 탄소수 5 내지 30의 아릴아민기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, 치환 또는 비치환되고 이종 원자로 O, N 또는 S를 갖는 탄소수 3 내지 50의 헤테로아릴기, 치환 또는 비치환된 실리콘기, 치환 또는 비치환된 붕소기, 치환 또는 비치환된 실란기, 카르보닐기, 포스포릴기, 아미노기, 니트릴기, 니트로기, 히드록시기, 할로겐기, 아미드기 및 에스테르기로 이루어진 군으로부터 1종 이상으로 치환되는 것을 특징으로 하는 축합아릴 화합물.The method of claim 1,
R 1 to R 6 , A 1 , A 2 , B 1 , B 2 , L 1 and L 2 are hydrogen atom, deuterium atom, substituted or unsubstituted C1-30 alkyl group, substituted or unsubstituted C2 Alkenyl group having 3 to 30, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted Substituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, substituted or unsubstituted alkylamine having 1 to 30 carbon atoms A heteroaryl group having 3 to 50 carbon atoms, having a substituted or unsubstituted arylamine group having 5 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 50 carbon atoms, substituted or unsubstituted and having O, N or S as a hetero atom. Group, substituted or unsubstituted yarn Substituted by one or more from the group consisting of a con group, a substituted or unsubstituted boron group, a substituted or unsubstituted silane group, a carbonyl group, a phosphoryl group, an amino group, a nitrile group, a nitro group, a hydroxyl group, a halogen group, an amide group and an ester group Condensed aryl compound, characterized in that. 제 1 항에 있어서,
상기 R1 내지 R6, A1, A2, B1, B2, L1, L2 및 치환기는 서로 인접한 기와 지방족, 방향족, 지방족헤테로 또는 방향족헤테로의 축합고리를 형성하거나 스피로결합을 형성하는 것을 특징으로 하는 축합아릴 화합물.The method of claim 1,
The R 1 to R 6 , A 1 , A 2 , B 1 , B 2 , L 1 , L 2 and substituents form a condensed ring of aliphatic, aromatic, aliphatic or aromatic hetero groups with adjacent groups to form spiro bonds. Condensed aryl compound, characterized in that. 제 1 항에 있어서,
상기 [화학식 1]은 하기 [화학식 50] 내지 [화학식 1265]로 표시되는 화합물 중에서 선택되는 어느 하나인 것을 특징으로 하는 축합아릴 화합물:
[화학식50] [화학식51] [화학식52] [화학식53]
Figure pat00385

[화학식54] [화학식55] [화학식56] [화학식57]
Figure pat00386

[화학식58] [화학식59] [화학식60] [화학식61]
Figure pat00387

[화학식62] [화학식63] [화학식64] [화학식65]
Figure pat00388

[화학식66] [화학식67] [화학식68] [화학식69]
Figure pat00389
[화학식70] [화학식71] [화학식72] [화학식73]
Figure pat00390
[화학식74] [화학식75] [화학식76] [화학식77]
Figure pat00391
[화학식78] [화학식79] [화학식80] [화학식81]
Figure pat00392
[화학식82] [화학식83] [화학식84] [화학식85]
Figure pat00393
[화학식86] [화학식87] [화학식88] [화학식89]
Figure pat00394
[화학식90] [화학식91] [화학식92] [화학식93]
Figure pat00395
[화학식94] [화학식95] [화학식96] [화학식97]
Figure pat00396
[화학식98] [화학식99] [화학식100] [화학식101]
Figure pat00397
[화학식102] [화학식103] [화학식104] [화학식105]
Figure pat00398
[화학식106] [화학식107] [화학식108] [화학식109]
Figure pat00399
[화학식110] [화학식111] [화학식112] [화학식113]
Figure pat00400
[화학식114] [화학식115] [화학식116] [화학식117]
Figure pat00401
[화학식118] [화학식119] [화학식120] [화학식121]
Figure pat00402
[화학식122] [화학식123] [화학식124] [화학식125]
Figure pat00403
[화학식126] [화학식127] [화학식128] [화학식129]
Figure pat00404
[화학식130] [화학식131] [화학식132] [화학식133]
Figure pat00405
[화학식134] [화학식135] [화학식136] [화학식137]
Figure pat00406
[화학식138] [화학식139] [화학식140] [화학식141]
Figure pat00407
[화학식142] [화학식143] [화학식144] [화학식145]
Figure pat00408
[화학식146] [화학식147] [화학식148] [화학식149]
Figure pat00409
[화학식150] [화학식151] [화학식152] [화학식153]
Figure pat00410

[화학식154] [화학식155] [화학식156] [화학식157]
Figure pat00411

[화학식158] [화학식159] [화학식160] [화학식161]
Figure pat00412

[화학식162] [화학식163] [화학식164] [화학식165]
Figure pat00413

[화학식166] [화학식167] [화학식168] [화학식169]
Figure pat00414

[화학식170] [화학식171] [화학식172] [화학식173]
Figure pat00415

[화학식174] [화학식175] [화학식176] [화학식177]
Figure pat00416

[화학식178] [화학식179] [화학식180] [화학식181]
Figure pat00417

[화학식182] [화학식183] [화학식184] [화학식185]
Figure pat00418

[화학식186] [화학식187] [화학식188] [화학식189]
Figure pat00419

[화학식190] [화학식191] [화학식192] [화학식193]
Figure pat00420

[화학식194] [화학식195] [화학식196] [화학식197]
Figure pat00421

[화학식198] [화학식199] [화학식200] [화학식201]
Figure pat00422

[화학식202] [화학식203] [화학식204] [화학식205]
Figure pat00423

[화학식206] [화학식207] [화학식208] [화학식209]
Figure pat00424

[화학식210] [화학식211] [화학식212] [화학식213]
Figure pat00425

[화학식214] [화학식215] [화학식216] [화학식217]
Figure pat00426

[화학식218] [화학식219] [화학식220] [화학식221]
Figure pat00427

[화학식222] [화학식223] [화학식224] [화학식225]
Figure pat00428

[화학식226] [화학식227] [화학식228] [화학식229]
Figure pat00429

[화학식230] [화학식231] [화학식232] [화학식233]
Figure pat00430

[화학식234] [화학식235] [화학식236] [화학식237]
Figure pat00431

[화학식238] [화학식239] [화학식240] [화학식241]
Figure pat00432

[화학식242] [화학식243] [화학식244] [화학식245]
Figure pat00433

[화학식246] [화학식247] [화학식248] [화학식249]
Figure pat00434

[화학식250] [화학식251] [화학식252] [화학식253]
Figure pat00435

[화학식254] [화학식255] [화학식256] [화학식257]
Figure pat00436

[화학식258] [화학식259] [화학식260] [화학식261]
Figure pat00437

[화학식262] [화학식263] [화학식264] [화학식265]
Figure pat00438

[화학식266] [화학식267] [화학식268] [화학식269]
Figure pat00439

[화학식270] [화학식271] [화학식272] [화학식273]
Figure pat00440

[화학식274] [화학식275] [화학식276] [화학식277]
Figure pat00441

[화학식278] [화학식279] [화학식280] [화학식281]
Figure pat00442

[화학식282] [화학식283] [화학식284] [화학식285]
Figure pat00443

[화학식286] [화학식287] [화학식288] [화학식289]
Figure pat00444

[화학식290] [화학식291] [화학식292] [화학식293]
Figure pat00445

[화학식294] [화학식295] [화학식296] [화학식297]
Figure pat00446

[화학식298] [화학식299] [화학식300] [화학식301]
Figure pat00447

[화학식302] [화학식303] [화학식304] [화학식305]
Figure pat00448

[화학식306] [화학식307] [화학식308] [화학식309]
Figure pat00449

[화학식310] [화학식311] [화학식312] [화학식313]
Figure pat00450

[화학식314] [화학식315] [화학식316] [화학식317]
Figure pat00451

[화학식318] [화학식319] [화학식320] [화학식321]
Figure pat00452

[화학식322] [화학식323] [화학식324] [화학식325]
Figure pat00453

[화학식326] [화학식327] [화학식328] [화학식329]
Figure pat00454

[화학식330] [화학식331] [화학식332] [화학식333]
Figure pat00455

[화학식334] [화학식335] [화학식336] [화학식337]
Figure pat00456

[화학식338] [화학식339] [화학식340] [화학식341]
Figure pat00457

[화학식342] [화학식343] [화학식344] [화학식345]
Figure pat00458

[화학식346] [화학식347] [화학식348] [화학식349]
Figure pat00459

[화학식350] [화학식351] [화학식352] [화학식353]
Figure pat00460

[화학식354] [화학식355] [화학식356] [화학식357]
Figure pat00461

[화학식358] [화학식359] [화학식360] [화학식361]
Figure pat00462

[화학식362] [화학식363] [화학식364] [화학식365]
Figure pat00463

[화학식366] [화학식367] [화학식368] [화학식369]
Figure pat00464

[화학식370] [화학식371] [화학식372] [화학식373]
Figure pat00465

[화학식374] [화학식375] [화학식376] [화학식377]
Figure pat00466

[화학식378] [화학식379] [화학식380] [화학식381]
Figure pat00467

[화학식382] [화학식383] [화학식384] [화학식385]
Figure pat00468

[화학식386] [화학식387] [화학식388] [화학식389]
Figure pat00469

[화학식390] [화학식391 ] [화학식392] [화학식393]
Figure pat00470

[화학식394] [화학식395] [화학식396] [화학식397]
Figure pat00471

[화학식398] [화학식399] [화학식400] [화학식401]
Figure pat00472

[화학식402] [화학식403] [화학식404] [화학식405]
Figure pat00473

[화학식406] [화학식407] [화학식408] [화학식409]
Figure pat00474

[화학식410] [화학식411] [화학식412] [화학식413]
Figure pat00475

[화학식414] [화학식415] [화학식416] [화학식417]
Figure pat00476

[화학식418] [화학식419] [화학식420] [화학식421]
Figure pat00477

[화학식422] [화학식423] [화학식424] [화학식425]
Figure pat00478

[화학식426] [화학식427] [화학식428] [화학식429]
Figure pat00479

[화학식430] [화학식431] [화학식432] [화학식433]
Figure pat00480

[화학식434] [화학식435] [화학식436] [화학식437]
Figure pat00481

[화학식438] [화학식439] [화학식440] [화학식441]
Figure pat00482

[화학식442] [화학식443] [화학식444] [화학식445]
Figure pat00483

[화학식446] [화학식447] [화학식448] [화학식449]
Figure pat00484

[화학식450] [화학식451] [화학식452] [화학식453]
Figure pat00485

[화학식454] [화학식455] [화학식456] [화학식457]
Figure pat00486

[화학식458] [화학식459] [화학식460] [화학식461]
Figure pat00487

[화학식462] [화학식463] [화학식464] [화학식465]
Figure pat00488

[화학식466] [화학식467] [화학식468] [화학식469]
Figure pat00489

[화학식470] [화학식471] [화학식472] [화학식473]
Figure pat00490

[화학식474] [화학식475] [화학식476] [화학식477]
Figure pat00491

[화학식478] [화학식479] [화학식480] [화학식481]
Figure pat00492

[화학식482] [화학식483] [화학식484] [화학식485]
Figure pat00493

[화학식486] [화학식487] [화학식488] [화학식489]
Figure pat00494

[화학식490] [화학식491] [화학식492] [화학식493]
Figure pat00495

[화학식494] [화학식495] [화학식496] [화학식497]
Figure pat00496

[화학식498] [화학식499] [화학식500] [화학식501]
Figure pat00497

[화학식502] [화학식503] [화학식504] [화학식505]
Figure pat00498

[화학식506] [화학식507] [화학식508] [화학식509]
Figure pat00499

[화학식510] [화학식511] [화학식512] [화학식513]
Figure pat00500

[화학식514] [화학식515] [화학식516] [화학식517]
Figure pat00501

[화학식518] [화학식519] [화학식520] [화학식521]
Figure pat00502

[화학식522] [화학식523] [화학식524] [화학식525]
Figure pat00503

[화학식526] [화학식527] [화학식528] [화학식529]
Figure pat00504

[화학식530] [화학식531] [화학식532] [화학식533]
Figure pat00505

[화학식534] [화학식535] [화학식536] [화학식537]
Figure pat00506

[화학식538] [화학식539] [화학식540] [화학식541]
Figure pat00507

[화학식542] [화학식543] [화학식544] [화학식545]
Figure pat00508

[화학식546] [화학식547] [화학식548] [화학식549]
Figure pat00509

[화학식550] [화학식551] [화학식552] [화학식553]
Figure pat00510

[화학식554] [화학식555] [화학식556] [화학식557]
Figure pat00511

[화학식558] [화학식559] [화학식560] [화학식561]
Figure pat00512

[화학식562] [화학식563] [화학식564] [화학식565]
Figure pat00513

[화학식566] [화학식567] [화학식568] [화학식569]
Figure pat00514

[화학식570] [화학식571] [화학식572] [화학식573]
Figure pat00515

[화학식574] [화학식575] [화학식576] [화학식577]
Figure pat00516

[화학식578] [화학식579] [화학식580] [화학식581]
Figure pat00517

[화학식582] [화학식583] [화학식584] [화학식585]
Figure pat00518

[화학식586] [화학식587] [화학식588] [화학식589]
Figure pat00519

[화학식590] [화학식591] [화학식592] [화학식593]
Figure pat00520

[화학식594] [화학식595] [화학식596] [화학식597]
Figure pat00521

[화학식598] [화학식599] [화학식600] [화학식601]
Figure pat00522

[화학식602] [화학식603] [화학식604] [화학식605]
Figure pat00523

[화학식606] [화학식607] [화학식608] [화학식609]
Figure pat00524

[화학식610] [화학식611] [화학식612] [화학식613]
Figure pat00525

[화학식614] [화학식615] [화학식616] [화학식617]
Figure pat00526

[화학식618] [화학식619] [화학식620] [화학식621]
Figure pat00527

[화학식622] [화학식623] [화학식624] [화학식625]
Figure pat00528

[화학식626] [화학식627] [화학식628] [화학식629]
Figure pat00529

[화학식630] [화학식631] [화학식632] [화학식633]
Figure pat00530

[화학식634] [화학식635] [화학식636] [화학식637]
Figure pat00531

[화학식638] [화학식639] [화학식640] [화학식641]
Figure pat00532

[화학식642] [화학식643] [화학식644] [화학식645]
Figure pat00533

[화학식646] [화학식647] [화학식648] [화학식649]
Figure pat00534

[화학식650] [화학식651] [화학식652] [화학식653]
Figure pat00535

[화학식654] [화학식655] [화학식656] [화학식657]
Figure pat00536

[화학식658] [화학식659] [화학식660] [화학식661]
Figure pat00537

[화학식662] [화학식663] [화학식664] [화학식665]
Figure pat00538

[화학식666] [화학식667] [화학식668] [화학식669]
Figure pat00539

[화학식670] [화학식671] [화학식672] [화학식673]
Figure pat00540

[화학식674] [화학식675] [화학식676] [화학식677]
Figure pat00541

[화학식678] [화학식679] [화학식680] [화학식681]
Figure pat00542

[화학식682] [화학식683] [화학식684] [화학식685]
Figure pat00543

[화학식686] [화학식687] [화학식688] [화학식689]
Figure pat00544

[화학식690] [화학식691] [화학식692] [화학식693]
Figure pat00545

[화학식694] [화학식695] [화학식696] [화학식697]
Figure pat00546

[화학식698] [화학식699] [화학식700] [화학식701]
Figure pat00547

[화학식702] [화학식703] [화학식704] [화학식705]
Figure pat00548

[화학식706] [화학식707] [화학식708] [화학식709]
Figure pat00549

[화학식710] [화학식711] [화학식712] [화학식713]
Figure pat00550

[화학식714] [화학식715] [화학식716] [화학식717]
Figure pat00551

[화학식718] [화학식719] [화학식720] [화학식721]
Figure pat00552

[화학식722] [화학식723] [화학식724] [화학식725]
Figure pat00553

[화학식726] [화학식727] [화학식728] [화학식729]
Figure pat00554

[화학식730] [화학식731] [화학식732] [화학식733]
Figure pat00555

[화학식734] [화학식735] [화학식736] [화학식737]
Figure pat00556

[화학식738] [화학식739] [화학식740] [화학식741]
Figure pat00557

[화학식742] [화학식743] [화학식744] [화학식745]
Figure pat00558

[화학식746] [화학식747] [화학식748] [화학식749]
Figure pat00559

[화학식750] [화학식751] [화학식752] [화학식753]
Figure pat00560

[화학식754] [화학식755] [화학식756] [화학식757]
Figure pat00561

[화학식758] [화학식759] [화학식760] [화학식761]
Figure pat00562

[화학식762] [화학식763] [화학식764] [화학식765]
Figure pat00563

[화학식766] [화학식767] [화학식768] [화학식769]
Figure pat00564

[화학식770] [화학식771] [화학식772] [화학식773]
Figure pat00565

[화학식774] [화학식775] [화학식776] [화학식777]
Figure pat00566

[화학식778] [화학식779] [화학식780] [화학식781]
Figure pat00567

[화학식782] [화학식783] [화학식784] [화학식785]
Figure pat00568

[화학식786] [화학식787] [화학식788] [화학식789]
Figure pat00569

[화학식790] [화학식791] [화학식792] [화학식793]
Figure pat00570

[화학식794] [화학식795] [화학식796] [화학식797]
Figure pat00571

[화학식798] [화학식799] [화학식800] [화학식801]
Figure pat00572

[화학식802] [화학식803] [화학식804] [화학식805]
Figure pat00573

[화학식806] [화학식807] [화학식808] [화학식809]
Figure pat00574

[화학식810] [화학식811] [화학식812] [화학식813]
Figure pat00575

[화학식814] [화학식815] [화학식816] [화학식817]
Figure pat00576

[화학식818] [화학식819] [화학식820] [화학식821]
Figure pat00577

[화학식822] [화학식823] [화학식824] [화학식825]
Figure pat00578

[화학식826] [화학식827] [화학식828] [화학식829]
Figure pat00579

[화학식830] [화학식831] [화학식832] [화학식833]
Figure pat00580

[화학식834] [화학식835] [화학식836] [화학식837]
Figure pat00581

[화학식838] [화학식839] [화학식840] [화학식841]
Figure pat00582

[화학식842] [화학식843] [화학식844] [화학식845]
Figure pat00583

[화학식846] [화학식847] [화학식848] [화학식849]
Figure pat00584

[화학식850] [화학식851] [화학식852] [화학식853]
Figure pat00585

[화학식854] [화학식855] [화학식856] [화학식857]
Figure pat00586

[화학식858] [화학식859] [화학식860] [화학식861]
Figure pat00587

[화학식862] [화학식863] [화학식864] [화학식865]
Figure pat00588

[화학식866] [화학식867] [화학식868] [화학식869]
Figure pat00589

[화학식870] [화학식871] [화학식872] [화학식873]
Figure pat00590

[화학식874] [화학식875] [화학식876] [화학식877]
Figure pat00591

[화학식878] [화학식879] [화학식880] [화학식881]
Figure pat00592

[화학식882] [화학식883] [화학식884] [화학식885]
Figure pat00593

[화학식886] [화학식887] [화학식888] [화학식889]
Figure pat00594

[화학식890] [화학식891] [화학식892] [화학식893]
Figure pat00595

[화학식894] [화학식895] [화학식896] [화학식897]
Figure pat00596

[화학식898] [화학식899] [화학식900] [화학식901]
Figure pat00597

[화학식902] [화학식903] [화학식904] [화학식905]
Figure pat00598

[화학식906] [화학식907] [화학식908] [화학식909]
Figure pat00599

[화학식910] [화학식911] [화학식912] [화학식913]
Figure pat00600

[화학식914] [화학식915] [화학식916] [화학식917]
Figure pat00601

[화학식918] [화학식919] [화학식920] [화학식921]
Figure pat00602

[화학식922] [화학식923] [화학식924] [화학식925]
Figure pat00603

[화학식926] [화학식927] [화학식928] [화학식929]
Figure pat00604

[화학식930] [화학식931] [화학식932] [화학식933]
Figure pat00605

[화학식934] [화학식935] [화학식936] [화학식937]
Figure pat00606

[화학식938] [화학식939] [화학식940] [화학식941]
Figure pat00607

[화학식942] [화학식943] [화학식944] [화학식945]
Figure pat00608

[화학식946] [화학식947] [화학식948] [화학식949]
Figure pat00609

[화학식950] [화학식951] [화학식952] [화학식953]
Figure pat00610

[화학식954] [화학식955] [화학식956] [화학식957]
Figure pat00611

[화학식958] [화학식959] [화학식960] [화학식961]
Figure pat00612

[화학식962] [화학식963] [화학식964] [화학식965]
Figure pat00613

[화학식966] [화학식967] [화학식968] [화학식969]
Figure pat00614

[화학식970] [화학식971] [화학식972] [화학식973]
Figure pat00615

[화학식974] [화학식975] [화학식976] [화학식977]
Figure pat00616

[화학식978] [화학식979] [화학식980] [화학식981]
Figure pat00617

[화학식982] [화학식983] [화학식984] [화학식985]
Figure pat00618

[화학식986] [화학식987] [화학식988] [화학식989]
Figure pat00619

[화학식990] [화학식991] [화학식992] [화학식993]
Figure pat00620

[화학식994] [화학식995] [화학식996] [화학식997]
Figure pat00621

[화학식998] [화학식999] [화학식1000] [화학식1001]
Figure pat00622

[화학식1002] [화학식1003] [화학식1004] [화학식1005]
Figure pat00623

[화학식1006] [화학식1007] [화학식1008] [화학식1009]
Figure pat00624

[화학식1010] [화학식1011] [화학식1012] [화학식1013]
Figure pat00625

[화학식1014] [화학식1015] [화학식1016] [화학식1017]
Figure pat00626

[화학식1018] [화학식1019] [화학식1020] [화학식1021]
Figure pat00627

[화학식1022] [화학식1023] [화학식1024] [화학식1025]
Figure pat00628

[화학식1026] [화학식1027] [화학식1028] [화학식1029]
Figure pat00629

[화학식1030] [화학식1031] [화학식1032] [화학식1033]
Figure pat00630

[화학식1034] [화학식1035] [화학식1036] [화학식1037]
Figure pat00631

[화학식1038] [화학식1039] [화학식1040] [화학식1041]
Figure pat00632

[화학식1042] [화학식1043] [화학식1044] [화학식1045]
Figure pat00633

[화학식1046] [화학식1047] [화학식1048] [화학식1049]
Figure pat00634

[화학식1050] [화학식1051] [화학식1052] [화학식1053]
Figure pat00635

[화학식1054] [화학식1055] [화학식1056] [화학식1057]
Figure pat00636

[화학식1058] [화학식1059] [화학식1060] [화학식1061]
Figure pat00637

[화학식1062] [화학식1063] [화학식1064] [화학식1065]
Figure pat00638

[화학식1066] [화학식1067] [화학식1068] [화학식1069]
Figure pat00639

[화학식1070] [화학식1071] [화학식1072] [화학식1073]
Figure pat00640

[화학식1074] [화학식1075] [화학식1076] [화학식1077]
Figure pat00641

[화학식1078] [화학식1079] [화학식1080] [화학식1081]
Figure pat00642

[화학식1082] [화학식1083] [화학식1084] [화학식1085]
Figure pat00643

[화학식1086] [화학식1087] [화학식1088] [화학식1089]
Figure pat00644

[화학식1090] [화학식1091] [화학식1092] [화학식1093]
Figure pat00645

[화학식1094] [화학식1095] [화학식1096] [화학식1097]
Figure pat00646

[화학식1098] [화학식1099] [화학식1100] [화학식1101]
Figure pat00647

[화학식1102] [화학식1103] [화학식1104] [화학식1105]
Figure pat00648

[화학식1106] [화학식1107] [화학식1108] [화학식1109]
Figure pat00649

[화학식1110] [화학식1111] [화학식1112] [화학식1113]
Figure pat00650

[화학식1114] [화학식1115] [화학식1116] [화학식1117]
Figure pat00651

[화학식1118] [화학식1119] [화학식1120] [화학식1121]
Figure pat00652

[화학식1122] [화학식1123] [화학식1124] [화학식1125]
Figure pat00653

[화학식1126] [화학식1127] [화학식1128] [화학식1129]
Figure pat00654

[화학식1130] [화학식1131] [화학식1132] [화학식1133]

[화학식1134] [화학식1135] [화학식1136] [화학식1137]
Figure pat00656

[화학식1138] [화학식1139] [화학식1140] [화학식1141]
Figure pat00657

[화학식1142] [화학식1143] [화학식1144] [화학식1145]
Figure pat00658

[화학식1146] [화학식1147] [화학식1148] [화학식1149]
Figure pat00659

[화학식1150] [화학식1151] [화학식1152] [화학식1153]
Figure pat00660

[화학식1154] [화학식1155] [화학식1156] [화학식1157]
Figure pat00661

[화학식1158] [화학식1159] [화학식1160] [화학식1161]
Figure pat00662

[화학식1162] [화학식1163] [화학식1164] [화학식1165]
Figure pat00663

[화학식1166] [화학식1167] [화학식1168] [화학식1169]
Figure pat00664

[화학식1170] [화학식1171] [화학식1172] [화학식1173]
Figure pat00665

[화학식1174] [화학식1175] [화학식1176] [화학식1177]
Figure pat00666

[화학식1178] [화학식1179] [화학식1180] [화학식1181]
Figure pat00667

[화학식1182] [화학식1183] [화학식1184] [화학식1185]
Figure pat00668

[화학식1186] [화학식1187] [화학식1188] [화학식1189]
Figure pat00669

[화학식1190] [화학식1191] [화학식1192] [화학식1193]
Figure pat00670

[화학식1194] [화학식1195] [화학식1196] [화학식1197]
Figure pat00671

[화학식1198] [화학식1199] [화학식1200] [화학식1201]
Figure pat00672

[화학식1202] [화학식1203] [화학식1204] [화학식1205]
Figure pat00673

[화학식1206] [화학식1207] [화학식1208] [화학식1209]
Figure pat00674

[화학식1210] [화학식1211] [화학식1212] [화학식1213]
Figure pat00675

[화학식1214] [화학식1215] [화학식1216] [화학식1217]
Figure pat00676

[화학식1218] [화학식1219] [화학식1220] [화학식1221]
Figure pat00677

[화학식1222] [화학식1223] [화학식1224] [화학식1225]
Figure pat00678

[화학식1226] [화학식1227] [화학식1228] [화학식1229]
Figure pat00679

[화학식1230] [화학식1231] [화학식1232] [화학식1233]
Figure pat00680

[화학식1234] [화학식1235] [화학식1236] [화학식1237]
Figure pat00681

[화학식1238] [화학식1239] [화학식1240] [화학식1241]
Figure pat00682

[화학식1242] [화학식1243] [화학식1244] [화학식1245]
Figure pat00683

[화학식1246] [화학식1247] [화학식1248] [화학식1249]
Figure pat00684

[화학식1250] [화학식1251] [화학식1252] [화학식1253]
Figure pat00685

[화학식1254] [화학식1255] [화학식1256] [화학식1257]
Figure pat00686

[화학식1258] [화학식1259] [화학식1260] [화학식1261]
Figure pat00687

[화학식1262] [화학식1263] [화학식1264] [화학식1265]
Figure pat00688
The method of claim 1,
[Formula 1] is a condensed aryl compound, characterized in that any one selected from the compounds represented by the following [Formula 50] to [Formula 1265]:
[Formula 50] [Formula 51] [Formula 52] [Formula 53]
Figure pat00385

[Formula 54] [Formula 55] [Formula 56] [Formula 57]
Figure pat00386

[Formula 58] [Formula 59] [Formula 60] [Formula 61]
Figure pat00387

[Formula 62] [Formula 63] [Formula 64] [Formula 65]
Figure pat00388

[Formula 66] [Formula 67] [Formula 68] [Formula 69]
Figure pat00389
[Formula 70] [Formula 71] [Formula 72] [Formula 73]
Figure pat00390
[Formula 74] [Formula 75] [Formula 76] [Formula 77]
Figure pat00391
[Formula 78] [Formula 79] [Formula 80] [Formula 81]
Figure pat00392
[Formula 82] [Formula 83] [Formula 84] [Formula 85]
Figure pat00393
[Formula 86] [Formula 87] [Formula 88] [Formula 89]
Figure pat00394
[Formula 90] [Formula 91] [Formula 92] [Formula 93]
Figure pat00395
[Formula 94] [Formula 95] [Formula 96] [Formula 97]
Figure pat00396
[Formula 98] [Formula 99] [Formula 100] [Formula 101]
Figure pat00397
[Formula 102] [Formula 103] [Formula 104] [Formula 105]
Figure pat00398
[Formula 106] [Formula 107] [Formula 108] [Formula 109]
Figure pat00399
[Formula 110] [Formula 111] [Formula 112] [Formula 113]
Figure pat00400
[Formula 114] [Formula 115] [Formula 116] [Formula 117]
Figure pat00401
[Formula 118] [Formula 119] [Formula 120] [Formula 121]
Figure pat00402
[Formula 122] [Formula 123] [Formula 124] [Formula 125]
Figure pat00403
[Formula 126] [Formula 127] [Formula 128] [Formula 129]
Figure pat00404
[Formula 130] [Formula 131] [Formula 132] [Formula 133]
Figure pat00405
[Formula 134] [Formula 135] [Formula 136] [Formula 137]
Figure pat00406
[Chemical Formula 140] [Chemical Formula 140] [Chemical Formula 140]
Figure pat00407
[Formula 142] [Formula 143] [Formula 144] [Formula 145]
Figure pat00408
[Formula 146] [Formula 147] [Formula 148] [Formula 149]
Figure pat00409
[Formula 150] [Formula 151] [Formula 152] [Formula 153]
Figure pat00410

[Formula 154] [Formula 155] [Formula 156] [Formula 157]
Figure pat00411

[Formula 158] [Formula 159] [Formula 160] [Formula 161]
Figure pat00412

[Formula 162] [Formula 163] [Formula 164] [Formula 165]
Figure pat00413

[Formula 166] [Formula 167] [Formula 168] [Formula 169]
Figure pat00414

[Formula 170] [Formula 171] [Formula 172] [Formula 173]
Figure pat00415

[Formula 174] [Formula 175] [Formula 176] [Formula 177]
Figure pat00416

[Formula 178] [Formula 179] [Formula 180] [Formula 181]
Figure pat00417

[Formula 182] [Formula 183] [Formula 184] [Formula 185]
Figure pat00418

[Formula 186] [Formula 187] [Formula 188] [Formula 189]
Figure pat00419

[Formula 190] [Formula 191] [Formula 192] [Formula 193]
Figure pat00420

[Formula 194] [Formula 195] [Formula 196] [Formula 197]
Figure pat00421

[Formula 198] [Formula 199] [Formula 200] [Formula 201]
Figure pat00422

[Formula 202] [Formula 203] [Formula 204] [Formula 205]
Figure pat00423

[Formula 206] [Formula 207] [Formula 208] [Formula 209]
Figure pat00424

[Formula 210] [Formula 211] [Formula 212] [Formula 213]
Figure pat00425

[Formula 214] [Formula 215] [Formula 216] [Formula 217]
Figure pat00426

[Formula 218] [Formula 219] [Formula 220] [Formula 221]
Figure pat00427

[Formula 222] [Formula 223] [Formula 224] [Formula 225]
Figure pat00428

[Formula 226] [Formula 227] [Formula 228] [Formula 229]
Figure pat00429

[Formula 230] [Formula 231] [Formula 232] [Formula 233]
Figure pat00430

[Formula 234] [Formula 235] [Formula 236] [Formula 237]
Figure pat00431

[Formula 238] [Formula 239] [Formula 240] [Formula 241]
Figure pat00432

[Formula 242] [Formula 243] [Formula 244] [Formula 245]
Figure pat00433

[Formula 246] [Formula 247] [Formula 248] [Formula 249]
Figure pat00434

[Formula 250] [Formula 251] [Formula 252] [Formula 253]
Figure pat00435

[Formula 254] [Formula 255] [Formula 256] [Formula 257]
Figure pat00436

[Formula 258] [Formula 259] [Formula 260] [Formula 261]
Figure pat00437

[Formula 262] [Formula 263] [Formula 264] [Formula 265]
Figure pat00438

[Formula 266] [Formula 267] [Formula 268] [Formula 269]
Figure pat00439

[Formula 270] [Formula 271] [Formula 272] [Formula 273]
Figure pat00440

[Formula 274] [Formula 275] [Formula 276] [Formula 277]
Figure pat00441

[Formula 278] [Formula 279] [Formula 280] [Formula 281]
Figure pat00442

[Formula 282] [Formula 283] [Formula 284] [Formula 285]
Figure pat00443

[Formula 286] [Formula 287] [Formula 288] [Formula 289]
Figure pat00444

[Formula 290] [Formula 291] [Formula 292] [Formula 293]
Figure pat00445

[Formula 294] [Formula 295] [Formula 296] [Formula 297]
Figure pat00446

[Formula 298] [Formula 299] [Formula 300] [Formula 301]
Figure pat00447

[Formula 302] [Formula 303] [Formula 304] [Formula 305]
Figure pat00448

[Formula 306] [Formula 307] [Formula 308] [Formula 309]
Figure pat00449

[Formula 310] [Formula 311] [Formula 312] [Formula 313]
Figure pat00450

[Formula 314] [Formula 315] [Formula 316] [Formula 317]
Figure pat00451

[Formula 318] [Formula 319] [Formula 320] [Formula 321]
Figure pat00452

[Formula 322] [Formula 323] [Formula 324] [Formula 325]
Figure pat00453

[Formula 326] [Formula 327] [Formula 328] [Formula 329]
Figure pat00454

[Formula 330] [Formula 331] [Formula 332] [Formula 333]
Figure pat00455

[Formula 334] [Formula 335] [Formula 336] [Formula 337]
Figure pat00456

[Formula 338] [Formula 339] [Formula 340] [Formula 341]
Figure pat00457

[Formula 342] [Formula 343] [Formula 344] [Formula 345]
Figure pat00458

[Formula 346] [Formula 347] [Formula 348] [Formula 349]
Figure pat00459

[Formula 350] [Formula 351] [Formula 352] [Formula 353]
Figure pat00460

[Formula 354] [Formula 355] [Formula 356] [Formula 357]
Figure pat00461

[Formula 358] [Formula 359] [Formula 360] [Formula 361]
Figure pat00462

[Formula 362] [Formula 363] [Formula 364] [Formula 365]
Figure pat00463

[Formula 366] [Formula 367] [Formula 368] [Formula 369]
Figure pat00464

[Formula 370] [Formula 371] [Formula 372] [Formula 373]
Figure pat00465

[Formula 374] [Formula 375] [Formula 376] [Formula 377]
Figure pat00466

[Formula 378] [Formula 379] [Formula 380] [Formula 381]
Figure pat00467

[Formula 382] [Formula 383] [Formula 384] [Formula 385]
Figure pat00468

[Formula 386] [Formula 387] [Formula 388] [Formula 389]
Figure pat00469

[Formula 390] [Formula 391] [Formula 392] [Formula 393]
Figure pat00470

[Formula 394] [Formula 395] [Formula 396] [Formula 397]
Figure pat00471

[Formula 398] [Formula 399] [Formula 400] [Formula 401]
Figure pat00472

[Formula 402] [Formula 403] [Formula 404] [Formula 405]
Figure pat00473

[Formula 406] [Formula 407] [Formula 408] [Formula 409]
Figure pat00474

[Formula 410] [Formula 411] [Formula 412] [Formula 413]
Figure pat00475

[Formula 414] [Formula 415] [Formula 416] [Formula 417]
Figure pat00476

[Formula 418] [Formula 419] [Formula 420] [Formula 421]
Figure pat00477

[Formula 422] [Formula 423] [Formula 424] [Formula 425]
Figure pat00478

[Formula 426] [Formula 427] [Formula 428] [Formula 429]
Figure pat00479

[Formula 430] [Formula 431] [Formula 432] [Formula 433]
Figure pat00480

[Formula 434] [Formula 435] [Formula 436] [Formula 437]
Figure pat00481

[Formula 438] [Formula 439] [Formula 440] [Formula 441]
Figure pat00482

[Formula 442] [Formula 443] [Formula 444] [Formula 445]
Figure pat00483

[Formula 446] [Formula 447] [Formula 448] [Formula 449]
Figure pat00484

[Formula 450] [Formula 451] [Formula 452] [Formula 453]
Figure pat00485

[Formula 454] [Formula 455] [Formula 456] [Formula 457]
Figure pat00486

[Formula 458] [Formula 459] [Formula 460] [Formula 461]
Figure pat00487

[Formula 462] [Formula 463] [Formula 464] [Formula 465]
Figure pat00488

[Formula 466] [Formula 467] [Formula 468] [Formula 469]
Figure pat00489

[Formula 470] [Formula 471] [Formula 472] [Formula 473]
Figure pat00490

[Formula 474] [Formula 475] [Formula 476] [Formula 477]
Figure pat00491

[Formula 478] [Formula 479] [Formula 480] [Formula 481]
Figure pat00492

[Formula 482] [Formula 483] [Formula 484] [Formula 485]
Figure pat00493

[Formula 486] [Formula 487] [Formula 488] [Formula 489]
Figure pat00494

[Formula 490] [Formula 491] [Formula 492] [Formula 493]
Figure pat00495

[Formula 494] [Formula 495] [Formula 496] [Formula 497]
Figure pat00496

[Formula 498] [Formula 499] [Formula 500] [Formula 501]
Figure pat00497

[Formula 502] [Formula 503] [Formula 504] [Formula 505]
Figure pat00498

[Formula 506] [Formula 507] [Formula 508] [Formula 509]
Figure pat00499

[Formula 510] [Formula 511] [Formula 512] [Formula 513]
Figure pat00500

Formula 514] Formula 515 Formula 516 Formula 517
Figure pat00501

Formula 518] Formula 519 Formula 520
Figure pat00502

[Formula 522] [Formula 523] [Formula 524] [Formula 525]
Figure pat00503

[526] [Formula 527] [Formula 528] [Formula 529]
Figure pat00504

[Formula 530] [Formula 531] [Formula 532] [Formula 533]
Figure pat00505

[Formula 534] [Formula 535] [Formula 536] [Formula 537]
Figure pat00506

[Formula 538] [Formula 539] [Formula 540] [Formula 541]
Figure pat00507

[542] [Formula 543] [Formula 544] [Formula 545]
Figure pat00508

Formula 546 Formula 547 Formula 548 Formula 549
Figure pat00509

[Chemical Formula 550] [Chemical Formula 551] [Chemical Formula 552]
Figure pat00510

[Formula 554] [Formula 555] [Formula 556] [Formula 557]
Figure pat00511

Formula 558 Formula 559 Formula 560 Formula 561
Figure pat00512

[562] [Formula 563] [Formula 564] [Formula 565]
Figure pat00513

[Formula 566] [Formula 567] [Formula 568] [Formula 569]
Figure pat00514

[570] [Formula 571] [Formula 572] [Formula 573]
Figure pat00515

[Formula 574] [Formula 575] [Formula 576] [Formula 577]
Figure pat00516

[Formula 578] [Formula 579] [Formula 580] [Formula 581]
Figure pat00517

[58] [Formula 584] [Formula 584] [Formula 585]
Figure pat00518

[Formula 586] [Formula 587] [Formula 588] [Formula 589]
Figure pat00519

[590] [Formula 591] [Formula 592] [Formula 593]
Figure pat00520

[Formula 595] [Formula 595] [Formula 596] [Formula 597]
Figure pat00521

[Formula 598] [Formula 599] [Formula 600] [Formula 601]
Figure pat00522

[Formula 602] [Formula 603] [Formula 604] [Formula 605]
Figure pat00523

[Formula 606] [Formula 607] [Formula 608] [Formula 609]
Figure pat00524

[Formula 610] [Formula 611] [Formula 612] [Formula 613]
Figure pat00525

[Formula 614] [Formula 615] [Formula 616] [Formula 617]
Figure pat00526

Formula 618] Formula 619 Formula 620
Figure pat00527

[Formula 622] [Formula 623] [Formula 624] [Formula 625]
Figure pat00528

[Formula 626] [Formula 627] [Formula 628] [Formula 629]
Figure pat00529

[630] [Formula 631] [Formula 632] [Formula 633]
Figure pat00530

[Formula 634] [Formula 635] [Formula 636] [Formula 637]
Figure pat00531

[Formula 638] [Formula 639] [Formula 640] [Formula 641]
Figure pat00532

[642] [Formula 643] [Formula 644] [Formula 645]
Figure pat00533

[Formula 646] [Formula 647] [Formula 648] [Formula 649]
Figure pat00534

[650] [Formula 651] [Formula 652] [Formula 653]
Figure pat00535

[654] [Formula 655] [Formula 656] [Formula 657]
Figure pat00536

[Formula 658] [Formula 659] [Formula 660] [Formula 661]
Figure pat00537

[662] [Formula 663] [Formula 664] [Formula 665]
Figure pat00538

[Formula 666] [Formula 667] [Formula 668] [Formula 669]
Figure pat00539

[Formula 670] [Formula 671] [Formula 672] [Formula 673]
Figure pat00540

[Formula 674] [Formula 675] [Formula 676] [Formula 677]
Figure pat00541

[Formula 678] [Formula 679] [Formula 680] [Formula 681]
Figure pat00542

[Formula 682] [Formula 683] [Formula 684] [Formula 685]
Figure pat00543

[Formula 686] [Formula 687] [Formula 688] [Formula 689]
Figure pat00544

[690] [Formula 691] [Formula 692] [Formula 693]
Figure pat00545

[Formula 695] [Formula 695] [Formula 696] [Formula 697]
Figure pat00546

[Formula 698] [Formula 699] [Formula 700] [Formula 701]
Figure pat00547

[Formula 702] [Formula 703] [Formula 704] [Formula 705]
Figure pat00548

[Formula 706] [Formula 707] [Formula 708] [Formula 709]
Figure pat00549

[Formula 710] [Formula 711] [Formula 712] [Formula 713]
Figure pat00550

[Formula 714] [Formula 715] [Formula 716] [Formula 717]
Figure pat00551

[Formula 718] [Formula 719] [Formula 720] [Formula 721]
Figure pat00552

[Formula 722] [Formula 723] [Formula 724] [Formula 725]
Figure pat00553

[Formula 726] [Formula 727] [Formula 728] [Formula 729]
Figure pat00554

[Formula 730] [Formula 731] [Formula 732] [Formula 733]
Figure pat00555

Formula 734] Formula 735 Formula 736 Formula 737
Figure pat00556

[Formula 738] [Formula 739] [Formula 740] [Formula 741]
Figure pat00557

[Formula 742] [Formula 743] [Formula 744] [Formula 745]
Figure pat00558

[Formula 746] [Formula 747] [Formula 748] [Formula 749]
Figure pat00559

Formula 750] Formula 751] Formula 752
Figure pat00560

[Formula 754] [Formula 755] [Formula 756] [Formula 757]
Figure pat00561

[Formula 758] [Formula 759] [Formula 760] [Formula 761]
Figure pat00562

[Formula 762] [Formula 763] [Formula 764] [Formula 765]
Figure pat00563

[Formula 766] [Formula 767] [Formula 768] [Formula 769]
Figure pat00564

[Formula 770] [Formula 771] [Formula 772] [Formula 773]
Figure pat00565

[Formula 774] [Formula 775] [Formula 776] [Formula 777]
Figure pat00566

[Formula 778] [Formula 779] [Formula 780] [Formula 781]
Figure pat00567

[Formula 782] [Formula 783] [Formula 784] [Formula 785]
Figure pat00568

[Formula 786] [Formula 787] [Formula 788] [Formula 789]
Figure pat00569

[Formula 790] [Formula 791] [Formula 792] [Formula 793]
Figure pat00570

[Formula 794] [Formula 795] [Formula 796] [Formula 797]
Figure pat00571

[Formula 798] [Formula 799] [Formula 800] [Formula 801]
Figure pat00572

[Formula 802] [Formula 803] [Formula 804] [Formula 805]
Figure pat00573

[Formula 806] [Formula 807] [Formula 808] [Formula 809]
Figure pat00574

[Formula 810] [Formula 811] [Formula 812] [Formula 813]
Figure pat00575

[Formula 814] [Formula 815] [Formula 816] [Formula 817]
Figure pat00576

[Formula 818] [Formula 819] [Formula 820] [Formula 821]
Figure pat00577

[822] [Formula 823] [Formula 824] [Formula 825]
Figure pat00578

[Formula 826] [Formula 827] [Formula 828] [Formula 829]
Figure pat00579

[Formula 830] [Formula 831] [Formula 832] [Formula 833]
Figure pat00580

834 [Formula 835] [Formula 836] [Formula 837]
Figure pat00581

[Formula 838] [Formula 839] [Formula 840] [Formula 841]
Figure pat00582

[Formula 842] [Formula 843] [Formula 844] [Formula 845]
Figure pat00583

[Formula 846] [Formula 847] [Formula 848] [Formula 849]
Figure pat00584

[Formula 850] [Formula 851] [Formula 852] [Formula 853]
Figure pat00585

[Formula 854] [Formula 855] [Formula 856] [Formula 857]
Figure pat00586

[Formula 858] [Formula 859] [Formula 860] [Formula 861]
Figure pat00587

[Formula 862] [Formula 863] [Formula 864] [Formula 865]
Figure pat00588

[Formula 866] [Formula 837] [Formula 868] [Formula 869]
Figure pat00589

Formula 870 [Formula 871] [Formula 872] [Formula 873]
Figure pat00590

[Formula 874] [Formula 875] [Formula 876] [Formula 877]
Figure pat00591

[Formula 878] [Formula 879] [Formula 880] [Formula 881]
Figure pat00592

[Formula 882] [Formula 883] [Formula 884] [Formula 885]
Figure pat00593

[Formula 886] [Formula 887] [Formula 888] [Formula 889]
Figure pat00594

[890] [Formula 891] [Formula 892] [Formula 833]
Figure pat00595

[Formula 894] [Formula 895] [Formula 896] [Formula 897]
Figure pat00596

[898] [Formula 899] [Formula 900] [Formula 901]
Figure pat00597

Formula 902 Formula 903 Formula 904 Formula 905
Figure pat00598

[Formula 906] [Formula 907] [Formula 908] [Formula 909]
Figure pat00599

[Formula 910] [Formula 911] [Formula 912] [Formula 913]
Figure pat00600

[Formula 914] [Formula 915] [Formula 916] [Formula 917]
Figure pat00601

[Formula 918] [Formula 919] [Formula 920] [Formula 921]
Figure pat00602

[92] [Formula 922] [Formula 924] [Formula 925]
Figure pat00603

Formula 926] Formula 927 Formula 928 Formula 929
Figure pat00604

[Formula 930] [Formula 931] [Formula 932] [Formula 933]
Figure pat00605

[Formula 934] [Formula 935] [Formula 936] [Formula 937]
Figure pat00606

[Formula 938] [Formula 939] [Formula 940] [Formula 941]
Figure pat00607

[Formula 942] [Formula 943] [Formula 944] [Formula 945]
Figure pat00608

[Formula 946] [Formula 947] [Formula 948] [Formula 949]
Figure pat00609

[Formula 950] [Formula 951] [Formula 952] [Formula 953]
Figure pat00610

[Formula 954] [Formula 955] [Formula 956] [Formula 957]
Figure pat00611

[Formula 958] [Formula 959] [Formula 960] [Formula 961]
Figure pat00612

[Formula 962] [Formula 963] [Formula 964] [Formula 965]
Figure pat00613

[Formula 966] [Formula 967] [Formula 968] [Formula 969]
Figure pat00614

[Formula 970] [Formula 971] [Formula 972] [Formula 973]
Figure pat00615

[Formula 974] [Formula 975] [Formula 976] [Formula 797]
Figure pat00616

[Formula 978] [Formula 979] [Formula 980] [Formula 981]
Figure pat00617

[Formula 982] [Formula 983] [Formula 984] [Formula 985]
Figure pat00618

[Formula 986] [Formula 987] [Formula 988] [Formula 989]
Figure pat00619

[Formula 990] [Formula 991] [Formula 992] [Formula 993]
Figure pat00620

[Formula 994] [Formula 995] [Formula 996] [Formula 997]
Figure pat00621

[Formula 998] [Formula 999] [Formula 1000] [Formula 1001]
Figure pat00622

[Formula 1002] [Formula 1003] [Formula 1004] [Formula 1005]
Figure pat00623

[Formula 1006] [Formula 1007] [Formula 1008] [Formula 1009]
Figure pat00624

[Formula 1010] [Formula 1011] [Formula 1012] [Formula 1013]
Figure pat00625

[Formula 1014] [Formula 1015] [Formula 1016] [Formula 1017]
Figure pat00626

[Formula 1018] [Formula 1019] [Formula 1020] [Formula 1021]
Figure pat00627

[Formula 1022] [Formula 1023] [Formula 1024] [Formula 1025]
Figure pat00628

[Formula 1026] [Formula 1027] [Formula 1028] [Formula 1029]
Figure pat00629

[Formula 1030] [Formula 1031] [Formula 1032] [Formula 1033]
Figure pat00630

[Formula 1034] [Formula 1035] [Formula 1036] [Formula 1037]
Figure pat00631

[Formula 1038] [Formula 1039] [Formula 1040] [Formula 1041]
Figure pat00632

[Formula 1042] [Formula 1043] [Formula 1044] [Formula 1045]
Figure pat00633

[Formula 1046] [Formula 1047] [Formula 1048] [Formula 1049]
Figure pat00634

[Formula 1050] [Formula 1051] [Formula 1052] [Formula 1053]
Figure pat00635

[Formula 1054] [Formula 1055] [Formula 1056] [Formula 1057]
Figure pat00636

[Formula 1058] [Formula 1059] [Formula 1060] [Formula 1061]
Figure pat00637

[Formula 1062] [Formula 1063] [Formula 1064] [Formula 1065]
Figure pat00638

[Formula 1066] [Formula 1067] [Formula 1068] [Formula 1069]
Figure pat00639

[Formula 1070] [Formula 1071] [Formula 1072] [Formula 1073]
Figure pat00640

[Formula 1074] [Formula 1075] [Formula 1076] [Formula 1077]
Figure pat00641

[Formula 1078] [Formula 1079] [Formula 1080] [Formula 1081]
Figure pat00642

[Formula 1082] [Formula 1083] [Formula 1084] [Formula 1085]
Figure pat00643

[Formula 1086] [Formula 1087] [Formula 1088] [Formula 1089]
Figure pat00644

[Formula 1090] [Formula 1091] [Formula 1092] [Formula 1093]
Figure pat00645

[Formula 1094] [Formula 1095] [Formula 1096] [Formula 1097]
Figure pat00646

[Formula 1098] [Formula 1099] [Formula 1100] [Formula 1101]
Figure pat00647

[Formula 1102] [Formula 1103] [Formula 1104] [Formula 1105]
Figure pat00648

[Formula 1106] [Formula 1107] [Formula 1108] [Formula 1109]
Figure pat00649

[Formula 1110] [Formula 1111] [Formula 1112] [Formula 1113]
Figure pat00650

[Formula 1114] [Formula 1115] [Formula 1116] [Formula 1117]
Figure pat00651

[Formula 1118] [Formula 1119] [Formula 1120] [Formula 1121]
Figure pat00652

[Formula 1122] [Formula 1123] [Formula 1124] [Formula 1125]
Figure pat00653

[Formula 1126] [Formula 1127] [Formula 1128] [Formula 1129]
Figure pat00654

[Formula 1130] [Formula 1131] [Formula 1132] [Formula 1333]

[Formula 1134] [Formula 1135] [Formula 1136] [Formula 1137]
Figure pat00656

[Formula 1138] [Formula 1139] [Formula 1140] [Formula 1141]
Figure pat00657

[Formula 1142] [Formula 1143] [Formula 1144] [Formula 1145]
Figure pat00658

[Formula 1146] [Formula 1147] [Formula 1148] [Formula 1149]
Figure pat00659

[Formula 1150] [Formula 1151] [Formula 1152] [Formula 1153]
Figure pat00660

[Formula 1154] [Formula 1155] [Formula 1156] [Formula 1157]
Figure pat00661

[Formula 1158] [Formula 1159] [Formula 1160] [Formula 1161]
Figure pat00662

[Formula 1162] [Formula 1163] [Formula 1164] [Formula 1165]
Figure pat00663

[Formula 1166] [Formula 1167] [Formula 1168] [Formula 1169]
Figure pat00664

[Formula 1170] [Formula 1171] [Formula 1172] [Formula 1173]
Figure pat00665

[Formula 1174] [Formula 1175] [Formula 1176] [Formula 1177]
Figure pat00666

[Formula 1178] [Formula 1179] [Formula 1180] [Formula 1181]
Figure pat00667

[Formula 1182] [Formula 1183] [Formula 1184] [Formula 1185]
Figure pat00668

[Formula 1186] [Formula 1187] [Formula 1188] [Formula 1189]
Figure pat00669

[Formula 1190] [Formula 1191] [Formula 1192] [Formula 1193]
Figure pat00670

[Formula 1194] [Formula 1195] [Formula 1196] [Formula 1197]
Figure pat00671

[Formula 1198] [Formula 1199] [Formula 1200] [Formula 1201]
Figure pat00672

[Formula 1202] [Formula 1203] [Formula 1204] [Formula 1205]
Figure pat00673

[Formula 1206] [Formula 1207] [Formula 1208] [Formula 1209]
Figure pat00674

[Formula 1210] [Formula 1211] [Formula 1212] [Formula 1213]
Figure pat00675

[Formula 1214] [Formula 1215] [Formula 1216] [Formula 1217]
Figure pat00676

[Formula 1218] [Formula 1219] [Formula 1220] [Formula 1221]
Figure pat00677

[Formula 1222] [Formula 1223] [Formula 1224] [Formula 1225]
Figure pat00678

[Formula 1226] [Formula 1227] [Formula 1228] [Formula 1229]
Figure pat00679

[Formula 1230] [Formula 1231] [Formula 1232] [Formula 1233]
Figure pat00680

[Formula 1234] [Formula 1235] [Formula 1236] [Formula 1237]
Figure pat00681

[Formula 1238] [Formula 1239] [Formula 1240] [Formula 1241]
Figure pat00682

[Formula 1242] [Formula 1243] [Formula 1244] [Formula 1245]
Figure pat00683

[Formula 1246] [Formula 1247] [Formula 1248] [Formula 1249]
Figure pat00684

[Formula 1250] [Formula 1251] [Formula 1252] [Formula 1253]
Figure pat00685

[Formula 1254] [Formula 1255] [Formula 1256] [Formula 1257]
Figure pat00686

[Formula 1258] [Formula 1259] [Formula 1260] [Formula 1261]
Figure pat00687

[Formula 1262] [Formula 1263] [Formula 1264] [Formula 1265]
Figure pat00688
 애노드;
캐소드; 및
상기 애노드와 상기 캐소드 사이에 개재되며, 제 1 항 내지 제 5 항 중 어느 한 항의 축합아릴 화합물을 포함하는 유기전계발광소자.Anode;
Cathode; And
An organic electroluminescent device interposed between the anode and the cathode and comprising the condensed aryl compound of any one of claims 1 to 5. 제 6 항에 있어서,
상기 축합아릴 화합물은 상기 애노드와 상기 캐소드 사이의 발광층 중에 포함되는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
The condensed aryl compound is an organic light emitting device, characterized in that contained in the light emitting layer between the anode and the cathode. 제 7 항에 있어서,
상기 애노드 및 캐소드 사이에 정공주입층, 정공수송층, 전자저지층, 정공저지층, 전자수송층 및 전자주입층으로 이루어진 군으로부터 선택된 하나 이상의 층을 더 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 7, wherein
An organic electroluminescent device further comprising at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer between the anode and the cathode. 제 8 항에 있어서,
상기 정공주입층, 정공수송층, 전자저지층, 발광층, 정공저지층, 전자수송층 및 전자주입층으로부터 선택된 하나 이상의 층은 단분자 증착방식 또는 용액공정에 의하여 형성되는 것을 특징으로 하는 유기전계발광소자.The method of claim 8,
At least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a single molecule deposition method or a solution process. 제 6 항에 있어서,
상기 유기전계발광소자는 표시소자, 디스플레이 소자, 또는 단색 또는 백색 조명용 소자에 사용되는 것을 특징으로 하는 유기전계발광소자.The method according to claim 6,
The organic electroluminescent device is an organic electroluminescent device, characterized in that used for a display device, a display device, or a device for monochrome or white illumination.
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JP2013232520A (en) * 2012-04-27 2013-11-14 Udc Ireland Ltd Organic electroluminescent element, compound and organic electroluminescent element material usable for the same, and light emitting device, display device and lighting device using said element
US20140117326A1 (en) * 2012-10-30 2014-05-01 Sun-young Lee Heterocyclic compound and organic light-emitting device including the same
US20140117331A1 (en) * 2012-11-01 2014-05-01 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
KR20140074857A (en) * 2012-12-10 2014-06-18 에스에프씨 주식회사 An electroluminescent compound and an electroluminescent device comprising the same
US20140209880A1 (en) * 2013-01-30 2014-07-31 Samsung Display Co., Ltd. Organic light-emitting diode
CN104513660A (en) * 2013-09-30 2015-04-15 北京鼎材科技有限公司 Organic luminescence material and applications thereof
JP2016102071A (en) * 2014-11-27 2016-06-02 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． Monoamine derivative and organic electroluminescent device
KR20160064948A (en) * 2014-11-27 2016-06-08 삼성디스플레이 주식회사 Monoamine derivative and organic electroluminescece device including the same
US20160365521A1 (en) * 2015-06-11 2016-12-15 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting device including the same
US10224487B2 (en) 2013-09-17 2019-03-05 Samsung Display Co., Ltd. Organic light-emitting device
CN109503643A (en) * 2017-09-14 2019-03-22 北京夏禾科技有限公司 Siliceous luminous organic material
WO2019194617A1 (en) * 2018-04-05 2019-10-10 주식회사 엘지화학 Amine compound and organic light emitting diode comprising same
US10446760B2 (en) 2014-05-12 2019-10-15 Samsung Sdi Co., Ltd. Organic compound, organic optoelectric diode, and display device
WO2019235725A1 (en) * 2018-06-08 2019-12-12 삼성에스디아이 주식회사 Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
CN111051294A (en) * 2017-09-08 2020-04-21 默克专利有限公司 Material for electronic devices
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