KR101290015B1 - Anthracene derivative and organic electroluminescence device using the same - Google Patents

Anthracene derivative and organic electroluminescence device using the same Download PDF

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KR101290015B1
KR101290015B1 KR1020110127284A KR20110127284A KR101290015B1 KR 101290015 B1 KR101290015 B1 KR 101290015B1 KR 1020110127284 A KR1020110127284 A KR 1020110127284A KR 20110127284 A KR20110127284 A KR 20110127284A KR 101290015 B1 KR101290015 B1 KR 101290015B1
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compound
synthesis
replaced
preparation
amine
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KR1020110127284A
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Korean (ko)
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KR20130060953A (en
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백영미
박호철
이은정
김태형
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주식회사 두산
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Priority to KR1020110127284A priority Critical patent/KR101290015B1/en
Priority to PCT/KR2012/010302 priority patent/WO2013081410A1/en
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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Abstract

본 발명은 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자에 관한 것으로, 구체적으로는 2, 6번 위치에 아민기가 비대칭으로 치환된 안트라센 유도체의 합성과 합성된 안트라센 유도체를 유기 전계 발광 소자에 적용하는 것이다. 이와 같은 본 발명은 효율, 수명 및 안정성 등이 향상된 유기 전계 발광 소자를 제공할 수 있다.The present invention relates to an anthracene derivative and an organic electroluminescent device using the same, and specifically, to synthesize an anthracene derivative in which an amine group is asymmetrically substituted at positions 2 and 6 and apply an anthracene derivative to an organic electroluminescent device. The present invention can provide an organic electroluminescent device with improved efficiency, lifetime, and stability.

Description

안트라센 유도체 및 이를 이용한 유기 전계 발광 소자{ANTHRACENE DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME}Anthracene derivative and organic electroluminescent device using the same {ANTHRACENE DERIVATIVE AND ORGANIC ELECTROLUMINESCENCE DEVICE USING THE SAME}

본 발명은 유기 전계 발광 소자의 효율, 수명 및 안정성 등을 향상시킬 수 있는 신규한 안트라센 유도체에 관한 것이다.The present invention relates to a novel anthracene derivative capable of improving the efficiency, lifespan and stability of the organic electroluminescent device.

유기 발광 현상이란 유기 물질을 이용하여 전기 에너지를 빛 에너지로 전환시켜 주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 전계 발광 소자는 통상 양극, 음극 및 이들 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 전계 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어질 수 있다. 예컨대 정공 주입층, 정공 수송층(HTL), 발광층(EML), 전자 수송층(ETL), 전자 주입층 등을 포함할 수 있다.The organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic EL device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer may be formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic EL device. For example, it may include a hole injection layer, a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer.

이러한 유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주게 되면 양극에서 정공이, 음극에서 전자가 유기물층으로 주입되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)을 형성하며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료, 전하 수송 재료, 정공 주입 재료, 정공 수송 재료, 전자 수송 재료, 전자 주입 재료 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected from the anode, electrons are injected into the organic material layer from the cathode, and excitons are formed when the injected holes and electrons meet. When it falls to, it will shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a charge transport material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와, 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 재료로서 호스트/도판트 계를 사용할 수 있다. 그 원리는 발광층을 주로 구성하는 호스트보다 에너지 대역 간극이 작고 발광 효율이 우수한 도판트를 발광층에 소량 혼합하면, 호스트에서 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. The light emitting material may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize a better natural color according to the light emitting color. Further, in order to increase the color purity and increase the luminous efficiency through energy transfer, a host / dopant system can be used as a light emitting material. The principle is that when a small amount of dopant having a smaller energy band gap and a higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with the light emitting layer in a small amount, the excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, the desired wavelength light can be obtained depending on the type of the dopant used.

현재 널리 알려진 발광(형광) 재료로는 쿠마린 유도체, 퀴나크리돈 유도체, DPT 등의 화합물이 있다. 쿠마린 유도체 중 현재 가장 널리 쓰이는 물질은 C545T이다. 이들 재료는 Alq를 호스트로서 수 내지 수십 % 정도의 농도로 도핑되어 유기 전계 발광 소자의 발광 재료로 사용된다. 한편 일본공개특허공보 2001-131541호에는 발광 재료로 안트라센의 2번과 6번 위치 각각에 디아릴아미노기가 치환된 비스(2,6-디아릴아미노)-9,10-디페닐안트라센 유도체가 개시되어 있다.Currently widely known luminescent (fluorescent) materials include compounds such as coumarin derivatives, quinacridone derivatives and DPT. The most widely used coumarin derivative at present is C545T. These materials are doped with Alq as a host at a concentration of several to several ten percent, and used as a light emitting material of the organic electroluminescent device. Japanese Unexamined Patent Publication No. 2001-131541 discloses a bis (2,6-diarylamino) -9,10-diphenylanthracene derivative in which a diarylamino group is substituted at positions 2 and 6 of anthracene as a light emitting material, respectively. It is.

그런데, 이러한 종래의 발광 재료들은 우수한 발광 특성을 나타내기 위해 개발되었으나, 대형 패널의 제조에 많은 문제점을 가지고 있으며 유기 전계 발광 소자의 효율 및 안정성을 높이는 것에도 한계가 있다.By the way, these conventional light emitting materials have been developed to exhibit excellent light emission characteristics, but there are many problems in the manufacture of large panels, and there is a limit to increasing the efficiency and stability of the organic EL device.

본 발명은 상기한 문제점을 해결하기 위해, 유기 전계 발광 소자의 효율, 수명 및 안정성 등을 향상시킬 수 있는 신규 화합물(안트라센 유도체) 및 상기 화합물을 이용한 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In order to solve the above problems, an object of the present invention is to provide a novel compound (anthracene derivative) and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.

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

[화학식 1] [Formula 1]

Figure 112011095402950-pat00001
Figure 112011095402950-pat00001

상기 화학식 1에서, Ar1 내지 Ar4 중 하나 이상은 수소 또는 중수소를 제외한 치환기이고; Ar1과 Ar4가 서로 같을 경우 Ar2와 Ar3는 서로 다른 치환기이고, Ar1와 Ar3가 서로 같을 경우 Ar2와 Ar4는 서로 다른 치환기이며;In Formula 1, at least one of Ar 1 to Ar 4 is a substituent except hydrogen or deuterium; When Ar 1 and Ar 4 are the same as each other, Ar 2 and Ar 3 are different substituents, and when Ar 1 and Ar 3 are the same as each other, Ar 2 and Ar 4 are different substituents;

Ar1 내지 Ar4 는 서로 같거나 다르고, 수소, 중수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, C5~C40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아미노기, C6~C40의 디아릴아미노기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기 및 C3~C40의 헤테로시클로알킬기로 이루어진 군에서 선택되며;Ar 1 to Ar 4 are the same as or different from each other, hydrogen, deuterium, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamino group, C 6 ~ C 40 diarylamino group, C 6 to C 40 arylalkyl group, C 3 to C 40 cycloalkyl group and C 3 to C 40 heterocycloalkyl group;

R1 및 R2는 서로 같거나 다르고, 수소, 중수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, C5~C40의 헤테로아릴기, C6~C40의 아릴아미노기, C6~C40의 디아릴아미노기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기 및 C3~C40의 헤테로시클로알킬기로 이루어진 군에서 선택된다.R 1 and R 2 are the same or different from each other, hydrogen, deuterium, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 of the aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 arylamino group, C 6 ~ C 40 diarylamino group, C 6 ~ C 40 arylalkyl group, C 3 ~ C 40 cycloalkyl group and C 3 ~ C 40 heterocycloalkyl group.

또한, 본 발명은, 양극; 음극; 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층인 것이 특징인 유기 전계 발광 소자를 제공한다.In addition, the present invention, the anode; cathode; And one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is an organic material layer including the compound represented by Chemical Formula 1. An electroluminescent device is provided.

여기서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층일 수 있다.Here, the organic material layer including the compound represented by Formula 1 may be a light emitting layer.

본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광 재료로 사용할 경우, 종래의 발광 재료에 비해 유기 전계 발광 소자의 효율(발광 효율 및 전령 효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 따라서, 본 발명은 풀 칼라 유기 EL 패널의 성능 및 수명을 향상시킬 수 있다.When the compound represented by Chemical Formula 1 of the present invention is used as a light emitting material of an organic electroluminescent device, the efficiency (luminescence efficiency and messenger efficiency), lifetime, luminance, driving voltage, etc. of the organic electroluminescent device are improved compared to conventional light emitting materials. You can. Therefore, the present invention can improve the performance and lifetime of the full color organic EL panel.

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

1. 신규 화합물(안트라센 유도체)1. Novel Compounds (Anthracene Derivatives)

본 발명에 따른 신규 화합물은 안트라센의 2, 6번 위치에 아민기가 비대칭으로 치환된 안트라센 유도체로 하기 화학식 1로 표시된다. 이러한 본 발명의 화학식 1로 표시되는 화합물은 녹색 발광 능력을 가진 물질이며, 유기 전계 발광 소자의 유기물층의 재료, 바람직하게는 발광층의 재료, 보다 바람직하게는 발광층의 도펀트 재료로 사용될 수 있다.The novel compound according to the present invention is an anthracene derivative in which an amine group is asymmetrically substituted at positions 2 and 6 of anthracene, and is represented by the following Chemical Formula 1. The compound represented by Chemical Formula 1 of the present invention is a material having a green light emitting ability, and may be used as a material of an organic material layer of an organic electroluminescent device, preferably a material of a light emitting layer, and more preferably a dopant material of a light emitting layer.

[화학식 1][Formula 1]

Figure 112011095402950-pat00002
Figure 112011095402950-pat00002

상기 화학식 1에서,In Formula 1,

Ar1 내지 Ar4 중 하나 이상은 수소 또는 중수소를 제외한 치환기이고;At least one of Ar 1 to Ar 4 is a substituent except hydrogen or deuterium;

Ar1과 Ar4가 서로 같을 경우 Ar2와 Ar3는 서로 다른 치환기이고, Ar1와 Ar3가 서로 같을 경우 Ar2와 Ar4는 서로 다른 치환기이며;When Ar 1 and Ar 4 are the same as each other, Ar 2 and Ar 3 are different substituents, and when Ar 1 and Ar 3 are the same as each other, Ar 2 and Ar 4 are different substituents;

Ar1 내지 Ar4 는 서로 같거나 다르고, 수소, 중수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, C5~C40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아미노기, C6~C40의 디아릴아미노기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기 및 C3~C40의 헤테로시클로알킬기로 이루어진 군에서 선택되며;Ar 1 to Ar 4 are the same as or different from each other, hydrogen, deuterium, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamino group, C 6 ~ C 40 diarylamino group, C 6 to C 40 arylalkyl group, C 3 to C 40 cycloalkyl group and C 3 to C 40 heterocycloalkyl group;

R1 및 R2는 서로 같거나 다르고, 수소, 중수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, C5~C40의 헤테로아릴기, C6~C40의 아릴아미노기, C6~C40의 디아릴아미노기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기 및 C3~C40의 헤테로시클로알킬기로 이루어진 군에서 선택된다.R 1 and R 2 are the same or different from each other, hydrogen, deuterium, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 of the aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 arylamino group, C 6 ~ C 40 diarylamino group, C 6 ~ C 40 arylalkyl group, C 3 ~ C 40 cycloalkyl group and C 3 ~ C 40 heterocycloalkyl group.

여기서, 상기 Ar1내지 Ar4와 R1 및 R2는 각각 중수소, 할로겐, 니트릴기, 니트로기, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C1~C40의 알콕시기, C1~C40의 아미노기, C3~C40의 시클로알킬기, C3~C40의 헤테로시클로알킬기, C6~C40의 아릴기 및 C5~C40의 헤테로아릴기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환되거나 비치환될 수 있으며, 인접하는 기와 축합(fused) 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리 또는 축합 헤테로방향족 고리를 형성할 수 있다.Here, Ar 1 to Ar 4 and R 1 and R 2 are each deuterium, halogen, nitrile group, nitro group, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 1 ~ C 40 alkoxy groups, C 1 to C 40 amino groups, C 3 to C 40 cycloalkyl groups, C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 5 to C 40 heteroaryl groups It may be substituted or unsubstituted with one or more substituents selected from the group consisting of, and may form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group.

한편, 유기 전계 발광 소자의 효율, 수명 및 안정성이 더욱 높아질 수 있도록 상기 R1 및 R2는 수소, C1~C40의 알킬기, C6~C40의 아릴기 및 C5~C40의 헤테로아릴기로 이루어진 군에서 선택되는 것이 바람직하다.On the other hand, organic light efficiency of the light emitting device, so that the life and reliability can be further increase the R 1 and R 2 are hydrogen, C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group and a C 5 ~ heteroaryl of C 40 It is preferably selected from the group consisting of aryl groups.

구체적으로, R1 및 R2는 상기 치환기로 치환되거나 비치환된(치환되지 않은) 메틸, i-프로필, t-부틸, 페닐, 바이페닐, 나프틸, 페난트렌, 9,9-디메틸-9H-플루오렌, 9,9-디페닐-9H-플루오렌 및 플루오란센으로 이루어진 군에서 선택되는 것이 바람직하다.Specifically, R 1 and R 2 are methyl, i-propyl, t-butyl, phenyl, biphenyl, naphthyl, phenanthrene, 9,9-dimethyl-9H substituted or unsubstituted (unsubstituted) with the above substituents. It is preferably selected from the group consisting of -fluorene, 9,9-diphenyl-9H-fluorene and fluoranthene.

또한, 본 발명의 화합물은 상기 R1 및 R2이 수소, C1~C40의 알킬기, C6~C40의 아릴기 및 C5~C40의 헤테로아릴기로 이루어진 군에서 선택될 때, 상기 Ar1 과 Ar4는 서로 같은 치환기이고, 상기 Ar2와 Ar3는 서로 다른 치환기인 것이 바람직하다. 구체적으로 상기 Ar1 내지 Ar4는 C1~C40의 알킬기, C6~C40의 아릴기 및 C5~C40의 헤테로아릴기로 이루어진 군에서 선택되는 것이 더욱 바람직하다.In addition, the compound of the present invention, when R 1 and R 2 is selected from the group consisting of hydrogen, C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group and C 5 ~ C 40 heteroaryl group, Ar 1 and Ar 4 are the same substituent, and Ar 2 and Ar 3 are preferably different substituents. Specifically, Ar 1 to Ar 4 is more preferably selected from the group consisting of C 1 ~ C 40 alkyl group, C 6 ~ C 40 aryl group and C 5 ~ C 40 heteroaryl group.

상기 R1 및 R2가 결합된 본 발명의 화합물의 예로 하기 화합물들(C-1 내지 C-54)을 들 수 있지만, 본 발명의 화합물이 하기 화합물들로 한정되는 것은 아니다.Examples of the compound of the present invention in which R 1 and R 2 are bonded include the following compounds (C-1 to C-54), but the compound of the present invention is not limited to the following compounds.

Figure 112011095402950-pat00003
Figure 112011095402950-pat00003

Figure 112011095402950-pat00004
Figure 112011095402950-pat00004

Figure 112011095402950-pat00005
Figure 112011095402950-pat00005

Figure 112011095402950-pat00006
Figure 112011095402950-pat00006

Figure 112011095402950-pat00007
Figure 112011095402950-pat00007

또한, 상기 화학식 1로 표시되는 본 발명의 화합물에서, 상기 Ar1 내지 Ar4에 해당되는 치환기의 예로 하기와 같은 예를 들 수 있지만, 이에 한정되는 것은 아니다.In addition, in the compound of the present invention represented by Formula 1, examples of the substituents corresponding to Ar 1 to Ar 4 include the following examples, but are not limited thereto.

Figure 112011095402950-pat00008
Figure 112011095402950-pat00008

이상에서 설명한 본 발명의 화합물(상기 화학식 1로 표시되는 화합물)의 구체적인 예로, 하기 화합물들(1 내지 309)을 들 수 있지만, 본 발명의 화합물이 하기 화합물들로 한정되는 것은 아니다.Specific examples of the compound of the present invention (compound represented by Formula 1) described above include the following compounds (1 to 309), but the compound of the present invention is not limited to the following compounds.

Figure 112011095402950-pat00009
Figure 112011095402950-pat00009

Figure 112011095402950-pat00010
Figure 112011095402950-pat00010

Figure 112011095402950-pat00011
Figure 112011095402950-pat00011

Figure 112011095402950-pat00012
Figure 112011095402950-pat00012

Figure 112011095402950-pat00013
Figure 112011095402950-pat00013

Figure 112011095402950-pat00014
Figure 112011095402950-pat00014

Figure 112011095402950-pat00015
Figure 112011095402950-pat00015

Figure 112011095402950-pat00016
Figure 112011095402950-pat00016

Figure 112011095402950-pat00017
Figure 112011095402950-pat00017

Figure 112011095402950-pat00018
Figure 112011095402950-pat00018

Figure 112011095402950-pat00019
Figure 112011095402950-pat00019

Figure 112011095402950-pat00020
Figure 112011095402950-pat00020

Figure 112011095402950-pat00021
Figure 112011095402950-pat00021

Figure 112011095402950-pat00022
Figure 112011095402950-pat00022

Figure 112011095402950-pat00023
Figure 112011095402950-pat00023

Figure 112011095402950-pat00024
Figure 112011095402950-pat00024

Figure 112011095402950-pat00025
Figure 112011095402950-pat00025

Figure 112011095402950-pat00026
Figure 112011095402950-pat00026

Figure 112011095402950-pat00027
Figure 112011095402950-pat00027

Figure 112011095402950-pat00028
Figure 112011095402950-pat00028

Figure 112011095402950-pat00029
Figure 112011095402950-pat00029

Figure 112011095402950-pat00030
Figure 112011095402950-pat00030

Figure 112011095402950-pat00031
Figure 112011095402950-pat00031

Figure 112011095402950-pat00032
Figure 112011095402950-pat00032

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

본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자를 제공하는데, 이때, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층인 것을 특징으로 한다.The present invention provides an organic electroluminescent device comprising an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 above. It is characterized in that the organic material layer containing a compound to be.

본 발명의 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상일 수 있다. 여기서, 본 발명의 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다.The organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer. Herein, the organic material layer including the compound represented by Chemical Formula 1 of the present invention is preferably a light emitting layer.

본 발명에 따른 유기 전계 발광 소자의 발광층은 도판트 재료를 함유할 수 있는데, 이때, 도판트 재료로 상기 화학식 1로 표시되는 화합물을 사용할 수 있는 것이다. 이와 같이 발광층이 상기 화학식 1로 표시되는 화합물을 함유할 경우 전자 수송 능력이 증가되어 발광층에서 정공과 전자의 결합력이 높아지기 때문에 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 우수한 유기 전계 발광 소자를 제공할 수 있다.The light emitting layer of the organic electroluminescent device according to the present invention may contain a dopant material, wherein the compound represented by the formula (1) can be used as the dopant material. As such, when the light emitting layer contains the compound represented by Chemical Formula 1, the electron transport ability is increased to increase the bonding force between the holes and the electrons in the light emitting layer, so that the organic light emitting layer has excellent efficiency (emission efficiency and power efficiency), lifetime, luminance, driving voltage, and the like. An electroluminescent device can be provided.

상기 화학식 1로 표시되는 화합물을 함유하는 발광층을 포함하는 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조로 이루어질 수 있다. 여기서, 전자 수송층 위에는 전자 주입층이 추가로 적층될 수도 있다. 또한, 본 발명에 따른 유기 전계 발광 소자는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조로 이루어질 수 있다.The structure of the organic electroluminescent device of the present invention including the light emitting layer containing the compound represented by Chemical Formula 1 is not particularly limited, but is not limited thereto, for example, a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode. It may be made of a sequentially stacked structure. Here, an electron injection layer may be further stacked on the electron transport layer. The organic electroluminescent device according to the present invention may have a structure in which an anode, one or more organic layers and an anode are sequentially stacked, and an insulating layer or an adhesive layer is interposed between the electrodes and the organic layer.

한편, 본 발명에 따른 유기 전계 발광 소자에 포함되는 양극으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 사용할 수 있다.On the other hand, the material that can be used as the anode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black.

본 발명에 따른 유기 전계 발광 소자에 포함되는 음극으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 사용할 수 있다.The material usable as the negative electrode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, Or metals such as lead or alloys thereof; And a multilayer structure material such as LiF / Al or LiO 2 / Al.

한편, 본 발명에 따른 유기 전계 발광 소자에 포함되는 유기물층은 상기 화학식 1로 표시되는 화합물을 함유하는 발광층을 사용하는 것을 제외하고는 당업계에 공지된 물질로 이루어질 수 있다. 즉, 정공 주입층, 정공 수송층 및 전자 수송층 등은 당업계에 알려진 통상의 물질로 이루어질 수 있다.On the other hand, the organic material layer included in the organic electroluminescent device according to the present invention may be made of a material known in the art except for using a light emitting layer containing the compound represented by the formula (1). That is, the hole injection layer, the hole transport layer and the electron transport layer may be made of a conventional material known in the art.

또한, 본 발명에 따른 유기 전계 발광 소자에 포함되는 기판으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다. In addition, the material usable as the substrate included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples may be used a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet.

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

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

1. 본 발명의 화합물 제조1. Preparation of Compounds of the Invention

본 발명에 따른 화합물은 하기 반응식에 의해 제조될 수 있다. 이때, n-A, n-B, n-C는 제조하고자 하는 화합물에 따라 변동되는 화합물로, 하기 반응식을 이용하여 본 발명의 화합물로 예시된 상기 1 내지 12, 16 내지 18, 37 내지 249 및 298 내지 309에 해당되는 화합물의 제조과정(합성과정)을 설명하면 하기와 같다.Compounds according to the invention can be prepared by the following schemes. In this case, nA, nB, nC is a compound that varies depending on the compound to be prepared, corresponding to the above 1 to 12, 16 to 18, 37 to 249 and 298 to 309 exemplified as a compound of the present invention using the following scheme The preparation process (synthesis process) of the compound is as follows.

[반응식][Reaction Scheme]

Figure 112011095402950-pat00033
Figure 112011095402950-pat00033

[[ 합성예Synthetic example 1] 화합물 7의 제조 1] Preparation of Compound 7

Figure 112011095402950-pat00034
Figure 112011095402950-pat00034

[합성예 1-1] 합성예 1의 화합물 7-1의 제조 Synthesis Example 1-1 Preparation of Compound 7-1 of Synthesis Example 1

플라스크에 2-브로모안트라퀴논(2,6-Dibromoanthraquinone) (50g, 175.37mmol), 화합물 7-A (9,9-디메틸-N-페닐-9H-플루오렌-2-아민(9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)) (99.88g, 350mmol), 트리스디벤질리덴아세톤디팔라듐(0)(tris(dibenzylideneacetone)dipalladium(0)) (12.4mg, 13.6mmol), 2-디-티-부틸포스피노비페닐(2-(Di-tbutylphospino)biphenyl) (7.0mg, 27.2mmol), 소듐 터트-부톡사이드(Sodium tert-butoxide) (28.7g, 298.7mmol), 및 톨루엔 250mL를 넣고 질소 하에서 120℃에서 8시간 동안 환류시켜 반응을 진행시켰다. 상온에서 반응 생성물을 유기층으로 추출, 재결정하여 화합물 7-1 (69.16g, 140.29mmol) (수율 80%)을 얻었다.In a flask 2-bromoanthraquinone (2,6-Dibromoanthraquinone) (50 g, 175.37 mmol), compound 7-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (9,9- dimethyl-N-phenyl-9H-fluoren-2-amine)) (99.88g, 350mmol), trisdibenzylideneacetonedipalladium (0) (tris (dibenzylideneacetone) dipalladium (0)) (12.4mg, 13.6mmol), 2- (Di-tbutylphospino) biphenyl (7.0 mg, 27.2 mmol), Sodium tert-butoxide (28.7 g, 298.7 mmol), and toluene 250 mL was added and refluxed at 120 ° C. for 8 hours under nitrogen to proceed with the reaction. The reaction product was extracted with an organic layer at room temperature and recrystallized to obtain compound 7-1 (69.16 g, 140.29 mmol) (yield 80%).

[합성예 1-2] 합성예 1의 화합물 7-2의 제조 Synthesis Example 1-2 Preparation of Compound 7-2 of Synthesis Example 1

플라스크에서 화합물 7-1 (69.16g, 140.29mmol), 화합물 7-B (2-브로모-2-메틸프로판 (2-bromo-2-methylpropane)) (47.96g, 350mmol), 징크더스트(zinc dust) (123.60g, 1588.3mmol), 및 커퍼썰페이트 (copper(II) sulfate) 0.5g을 30% 수산화나트륨 500 mL, 암모니아수(NH3) 20 mL 및 에탄올(Ethanol) 200mL의 혼합 용액에 녹이고 58시간 동안 환류하면서 반응을 진행시켰다. 반응이 종료된 후, 반응생성물을 상온에서 유기층으로 추출하여 분리하였다. 분리된 유기층을 이소프로필 알콜(isopropyl alcohol) 300mL와 20 mL의 염산 용액에 녹여 끓인 후 뜨거운 상태에서 여과 후 재결정하여 화합물 7-2 (45.01g, 78.56mmol)(수율 56%)를 얻었다.Compound 7-1 (69.16g, 140.29mmol), Compound 7-B (2-bromo-2-methylpropane) (47.96g, 350mmol), zinc dust in flask ) (123.60 g, 1588.3 mmol), and 0.5 g of copper (II) sulfate are dissolved in a mixed solution of 500 mL of 30% sodium hydroxide, 20 mL of ammonia water (NH3) and 200 mL of ethanol (Ethanol) for 58 hours. The reaction proceeded while refluxing. After the reaction was completed, the reaction product was separated by extraction into an organic layer at room temperature. The separated organic layer was dissolved in 300 mL of isopropyl alcohol and 20 mL of hydrochloric acid, boiled, filtered and recrystallized in a hot state to obtain compound 7-2 (45.01 g, 78.56 mmol) (yield 56%).

[합성예 1-3] 합성예 1의 화합물 7-3의 제조 Synthesis Example 1-3 Preparation of Compound 7-3 of Synthesis Example 1

디클로로메탄 500mL가 들어있는 플라스크에 화합물 7-2 (45.01g, 78.56mmol), 및 엔-브로모석시마이드(Nbromosuccinmide) (17.0g, 95.78mmol)을 녹인 후 실온에서 24시간 동안 교반하여 반응을 진행시킨 후, 물로 반응을 종결시켰다. 반응이 종결된 후 반응 생성물을 유기층으로 추출한 후 재결정하여 화합물 7-3 (40.97g, 62.85mmol) (수율 80%)을 얻었다.Compound 7-2 (45.01 g, 78.56 mmol) and Nbromosuccinmide (17.0 g, 95.78 mmol) were dissolved in a flask containing 500 mL of dichloromethane, followed by stirring at room temperature for 24 hours. After the reaction, the reaction was terminated with water. After the reaction was completed, the reaction product was extracted with an organic layer and recrystallized to obtain compound 7-3 (40.97g, 62.85mmol) (yield 80%).

[합성예 1-4] 합성예 1의 화합물 7의 제조 Synthesis Example 1-4 Preparation of Compound 7 of Synthesis Example 1

플라스크에서 화합물 7-3 (40.97g, 62.85mmol), 화합물 7-C (N-페닐-5,6디하이드로나프탈렌-2-아민(N-phenyl-5,6-dihydronaphthalen-2-amine)) (14.30g, 65.00mmol)과 테트라키스팔라듐(Tetrakis(triphenylphosphine) palladium(0)) (0.726g, 0.63mmol)을 톨루엔(toluene) 400mL과 에탄올(Ethanol) 200mL의 혼합용액에 녹인 후, 2M 탄산나트륨 수용액 200mL를 첨가하여 6시간 동안 환류시켜 반응을 진행하였다. 반응이 종료된 후 상온에서 증류수 적가 후 반응생성물을 유기층으로 추출 및 분리하였다. 분리된 유기층을 재결정 및 건조하여 화합물 7 (33.31g, 42.11mmol)(수율 67%)을 얻었다.Compound 7-3 (40.97g, 62.85mmol), Compound 7-C (N-phenyl-5,6-dihydronaphthalen-2-amine) in the flask ( 14.30g, 65.00mmol) and Tetrakis (triphenylphosphine) palladium (0)) (0.726g, 0.63mmol) were dissolved in a mixed solution of 400mL toluene and 200mL ethanol, 200mL 2M sodium carbonate solution The reaction was carried out by adding to reflux for 6 hours. After completion of the reaction, distilled water was added dropwise at room temperature, and the reaction product was extracted and separated into an organic layer. The separated organic layer was recrystallized and dried to give compound 7 (33.31 g, 42.11 mmol) (yield 67%).

Elemental Analysis: C, 89.58; H, 6.88; N, 3.54 [M+] : 790
Elemental Analysis: C, 89.58; H, 6.88; N, 3.54 [M +]: 790

[[ 합성예Synthetic example 2] 화합물 8의 제조 2] Preparation of Compound 8

[합성예 2-1] 화합물 8-1의 제조 Synthesis Example 2-1 Preparation of Compound 8-1

합성예 1-1의 화합물 7-A를 화합물 8-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Synthesis of Compound 7-1 by replacing Compound 7-A of Synthesis Example 1-1 with Compound 8-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine) It could be synthesized using the same method as.

[합성예 2-2] 화합물 8-2의 제조 Synthesis Example 2-2 Preparation of Compound 8-2

합성예 1-2의 화합물 7-1을 화합물 8-1로 대체하고 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 could be replaced with Compound 8-1, and synthesized using the same method as the synthesis of Compound 7-2.

[합성예 2-3] 화합물 8-3의 제조 Synthesis Example 2-3 Preparation of Compound 8-3

합성예 1-3의 화합물 7-2를 화합물 8-2로 대체하고 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 8-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 2-4] 화합물 8의 제조Synthesis Example 2-4 Preparation of Compound 8

합성예 1-4의 화합물 7-3을 화합물 8-3으로, 화합물 7-C를 8-C (diphenylamine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 8-3, Compound 7-C was substituted with 8-C (diphenylamine) and synthesized using the same method as the synthesis of Compound 7 (Synthesis Example 1-4). Could.

Elemental Analysis: C, 89.66; H, 6.91; N, 3.43 [M+] : 816
Elemental Analysis: C, 89.66; H, 6.91; N, 3.43 [M < + >]: 816

[[ 합성예Synthetic example 3] 화합물 9의 제조 3] Preparation of Compound 9

[합성예 3-1] 화합물 9-1의 제조 Synthesis Example 3-1 Preparation of Compound 9-1

합성예 1-1의 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. It synthesize | combined using the method similar to the synthesis | combination of the compound 7-1 of the synthesis example 1-1.

[합성예 3-2] 화합물 9-2의 제조 Synthesis Example 3-2 Preparation of Compound 9-2

합성예 1-2의 화합물7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. It synthesize | combined using the method similar to the synthesis | combination of the compound 7-2 of the synthesis example 1-2.

[합성예 3-3] 화합물 9-3의 제조 Synthesis Example 3-3 Preparation of Compound 9-3

합성예 1-3의 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. It synthesize | combined using the method similar to the synthesis | combination of the compound 7-3 of the synthesis example 1-3.

[합성예 3-4] 화합물 9의 제조 Synthesis Example 3-4 Preparation of Compound 9

합성예 1-4의 화합물 7-C를 화합물 9-C (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-C of Synthesis Example 1-4 was replaced with Compound 9-C (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and Compound 7 (Synthesis Example 1 Synthesis was carried out using the same method as the synthesis of -4).

Elemental Analysis: C, 90.02; H, 6.89; N, 3.09 [M+] : 906
Elemental Analysis: C, 90.02; H, 6.89; N, 3.09 [M < + >]: 906

[[ 합성예Synthetic example 4] 화합물 1의 제조 4] Preparation of Compound 1

[합성예 4-1] 화합물 1-1의 제조 Synthesis Example 4-1 Preparation of Compound 1-1

합성예 1-1의 화합물 7-A를 화합물 1-A (diphenylamine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 1-A (diphenylamine), and could be synthesized using the same method as the synthesis of Compound 7-1.

[합성예 4-2] 화합물 1-2의 제조 Synthesis Example 4-2 Preparation of Compound 1-2

합성예 1-2의 화합물 7-1을 화합물 1-1로 대체하고, 화합물 7-B를 제외한 후 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 1-1, and Compound 7-B was excluded and then synthesized using the same method as for synthesis of Compound 7-2.

[합성예 4-3] 화합물 1-3의 제조 Synthesis Example 4-3 Preparation of Compound 1-3

합성예 1-3의 화합물 7-2을 화합물 1-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 1-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 4-4] 화합물 1의 제조 Synthesis Example 4-4 Preparation of Compound 1

합성예 1-4의 화합물 7-3을 화합물 1-3으로, 화합물 7-C를 화합물 1-C (4-methyl-N-phenylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 1-3, Compound 7-C with Compound 1-C (4-methyl-N-phenylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 88.94; H, 5.74; N, 5.32 [M+]: 525
Elemental Analysis: C, 88.94; H, 5.74; N, 5.32 [M < + >]: 525

[[ 합성예Synthetic example 5] 화합물 2의 제조 5] Preparation of Compound 2

[합성예 5-1] 화합물 2-1의 제조 Synthesis Example 5-1 Preparation of Compound 2-1

합성예 1-1의 화합물 7-A를 화합물 2-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 2-A (N-phenylnaphthalen-2-amine), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 5-2] 화합물 2-2의 제조 Synthesis Example 5-2 Preparation of Compound 2-2

합성예 1-2의 화합물 7-1을 화합물 2-1로 대체하고, 화합물 7-B를 제외한 후 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 2-1, and Compound 7-B was excluded and then synthesized using the same method as for synthesis of Compound 7-2.

[합성예 5-3] 화합물 2-3의 제조 Synthesis Example 5-3 Preparation of Compound 2-3

합성예 1-3의 화합물 7-2을 화합물 2-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 2-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 5-4] 화합물 2의 제조 Synthesis Example 5-4 Preparation of Compound 2

합성예 1-4의 화합물 7-3을 화합물 2-3으로, 화합물 7-C를 화합물 2-C (N-(4-isopropylphenyl)naphthalen-2-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 2-3, Compound 7-C was replaced with Compound 2-C (N- (4-isopropylphenyl) naphthalen-2-amine), and Compound 7 (Synthesis Example 1 Synthesis was carried out using the same method as the synthesis of -4).

Elemental Analysis: C, 89.51; H, 6.31; N, 4.18 [M+]:669
Elemental Analysis: C, 89.51; H, 6.31; N, 4.18 [M < + >]: 669

[[ 합성예Synthetic example 6] 화합물 3의 제조 6] Preparation of Compound 3

[[ 합성예Synthetic example 6-1] 화합물 3-1의 제조 6-1] Preparation of Compound 3-1

합성예 1-1의 화합물 7-A를 화합물 3-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 3-A (N-phenylnaphthalen-2-amine), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 6-2] 화합물 3-2의 제조Synthesis Example 6-2 Preparation of Compound 3-2

합성예 1-2의 화합물 7-1을 화합물 3-1로 대체하고, 화합물 7-B를 제외한 후 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 3-1, and Compound 7-B was excluded, and then synthesized using the same method as for synthesis of Compound 7-2.

[합성예 6-3] 화합물 3-3의 제조Synthesis Example 6-3 Preparation of Compound 3-3

합성예 1-3의 화합물 7-2을 화합물 3-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 3-2, and was synthesized using the same method as the synthesis of Compound 7-3.

[합성예 6-4] 화합물 3의 제조Synthesis Example 6-4 Preparation of Compound 3

합성예 1-4의 화합물 7-3을 화합물 3-3으로, 화합물 7-C를 3-C (N-(4-fluorophenyl)naphthalen-2-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 3-3, Compound 7-C was replaced with 3-C (N- (4-fluorophenyl) naphthalen-2-amine), and Compound 7 (Synthesis Example 1- It could synthesize | combine using the same method as the synthesis of 4).

Elemental Analysis: C, 87.59; H, 4.95; F, 3.01; N, 4.44 [M+]:629
Elemental Analysis: C, 87.59; H, 4.95; F, 3.01; N, 4.44 [M < + >]: 629

[[ 합성예Synthetic example 7] 화합물 4의 제조 7] Preparation of Compound 4

[합성예 7-1] 화합물 4-1의 제조 Synthesis Example 7-1 Preparation of Compound 4-1

합성예 1-1의 화합물 7-A를 화합물 4-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 4-A (N-phenylnaphthalen-2-amine), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 7-2] 화합물 4-2의 제조 Synthesis Example 7-2 Preparation of Compound 4-2

합성예 1-2의 화합물 7-1을 화합물 4-1로, 화합물 7-B를 4-B (bromomethane)로 각각 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 4-1, and Compound 7-B was replaced with 4-B (bromomethane), respectively, and it could be synthesized by the same method as the synthesis of Compound 7-2.

[합성예 7-3] 화합물 4-3의 제조 Synthesis Example 7-3 Preparation of Compound 4-3

합성예 1-3의 화합물 7-2를 화합물 4-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 4-2, and was synthesized using the same method as the synthesis of Compound 7-3.

[합성예 7-4] 화합물 4의 제조 Synthesis Example 7-4 Preparation of Compound 4

합성예 1-4의 화합물 7-3을 화합물 4-3으로, 화합물 7-C를 4-C (4-(phenylamino)benzonitrile)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 4-3, and Compound 7-C was replaced with 4-C (4- (phenylamino) benzonitrile), and the same as the synthesis of Compound 7 (Synthesis Example 1-4). It could be synthesized using the method.

Elemental Analysis: C, 87.77; H, 5.40; N, 6.82 [M+]:614
Elemental Analysis: C, 87.77; H, 5.40; N, 6.82 [M < + >]: 614

[[ 합성예Synthetic example 8] 화합물 5의 제조 8] Preparation of Compound 5

[합성예 8-1] 화합물 5-1의 제조 Synthesis Example 8-1 Preparation of Compound 5-1

합성예 1-1의 화합물 7-A를 화합물 5-A (diphenylamine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 5-A (diphenylamine), and could be synthesized using the same method as the synthesis of Compound 7-1.

[합성예 8-2] 화합물 5-2의 제조 Synthesis Example 8-2 Preparation of Compound 5-2

합성예 1-2의 화합물 7-1을 화합물 5-1로, 화합물 7-B를 화합물 5-B (bromomethane)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 5-1, Compound 7-B with Compound 5-B (bromomethane), and the synthesis was carried out using the same method as the synthesis of Compound 7-2.

[합성예 8-3] 화합물 5-3의 제조 Synthesis Example 8-3 Preparation of Compound 5-3

합성예 1-3의 화합물 7-2를 화합물 5-2로 대체하고, 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 5-2, and was synthesized using the same method as the synthesis of Compound 7-3.

[합성예 8-4] 화합물 5의 제조 Synthesis Example 8-4 Preparation of Compound 5

합성예 1-4의 화합물 7-3을 화합물 5-3으로, 화합물 7-C를 화합물 5-C (4-methoxy-N-phenylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 5-3, Compound 7-C with Compound 5-C (4-methoxy-N-phenylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 86.28; H, 6.00; N, 4.91; O, 2.80 [M+]: 569
Elemental Analysis: C, 86.28; H, 6.00; N, 4.91; O, 2.80 [M < + >]: 569

[[ 합성예Synthetic example 9] 화합물 6의 제조 9] Preparation of Compound 6

[합성예 9-1] 화합물 6-1의 제조 Synthesis Example 9-1 Preparation of Compound 6-1

합성예 1-1의 화합물 7-A를 화합물 6-A (diphenylamine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 6-A (diphenylamine), and could be synthesized using the same method as the synthesis of Compound 7-1.

[합성예 9-2] 화합물 6-2의 제조 Synthesis Example 9-2 Preparation of Compound 6-2

합성예 1-2의 화합물 7-1을 화합물 6-1로, 화합물 7-B를 화합물 6-B (bromomethane)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 could be replaced with Compound 6-1, Compound 7-B with Compound 6-B (bromomethane), and synthesized using the same method as the synthesis of Compound 7-2.

[합성예 9-3] 화합물 6-3의 제조 Synthesis Example 9-3 Preparation of Compound 6-3

합성예 1-3의 화합물 7-2를 화합물 6-2로 대체하고, 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 6-2, and was synthesized using the same method as the synthesis of Compound 7-3.

[합성예 9-4] 화합물 6의 제조 Synthesis Example 9-4 Preparation of Compound 6

합성예 1-4의 화합물 7-3을 화합물 6-3으로, 화합물 7-C를 화합물 6-C (4-nitro-N-phenylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 6-3, Compound 7-C with Compound 6-C (4-nitro-N-phenylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 82.03; H, 5.33; N, 7.17; O, 5.46 [M+]:584
Elemental Analysis: C, 82.03; H, 5. 33; N, 7.17; O, 5.46 [M < + >]: 584

[[ 합성예Synthetic example 10] 화합물 10의 제조 10] Preparation of Compound 10

[합성예 10-1] 화합물 10-1의 제조 Synthesis Example 10-1 Preparation of Compound 10-1

합성예 1-1의 화합물 7-A를 화합물 10-A (N-phenylpyridin-4-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 10-A (N-phenylpyridin-4-amine), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 10-2] 화합물 10-2의 제조 Synthesis Example 10-2 Preparation of Compound 10-2

합성예 1-2의 화합물 7-1을 화합물 10-1로, 화합물 7-B를 화합물 10-B(bromoethene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 10-1, and Compound 7-B was replaced with Compound 10-B (bromoethene), and the synthesis was carried out using the same method as the synthesis of Compound 7-2.

[합성예 10-3] 화합물 10-3의 제조 Synthesis Example 10-3 Preparation of Compound 10-3

합성예 1-3의 화합물7-2를 화합물 10-2로 대체하고, 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 10-2, and was synthesized using the same method as the synthesis of Compound 7-3.

[합성예 10-4] 화합물 10의 제조 Synthesis Example 10-4 Preparation of Compound 10

합성예 1-4의 화합물 7-3을 화합물 10-3으로, 화합물 7-C를 화합물 10-C (N-phenylpyridin-2-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 10-3, Compound 7-C with Compound 10-C (N-phenylpyridin-2-amine) It could be synthesized using the same method as.

Elemental Analysis: C, 84.78; H, 5.34; N, 9.89 [M+]:565
Elemental Analysis: C, 84.78; H, 5.34; N, 9.89 [M < + >]: 565

[[ 합성예Synthetic example 11] 화합물 11의 제조 11] Preparation of Compound 11

[합성예 11-1] 화합물 11-1의 제조 Synthesis Example 11-1 Preparation of Compound 11-1

합성예 1-1의 화합물 7-A를 화합물 11-A (4-isopropyl-N-phenylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 11-A (4-isopropyl-N-phenylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 11-2] 화합물 11-2의 제조 Synthesis Example 11-2 Preparation of Compound 11-2

합성예 1-2의 화합물 7-1을 화합물 11-1로, 화합물 7-B를 화합물 11-B(bromoethene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 11-1, and Compound 7-B was replaced with Compound 11-B (bromoethene), and the synthesis was carried out using the same method as the synthesis of Compound 7-2.

[합성예 11-3] 화합물 11-3의 제조 Synthesis Example 11-3 Preparation of Compound 11-3

합성예 1-3의 화합물 7-2를 화합물 11-2로 대체하고, 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 11-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 11-4] 화합물 11의 제조 Synthesis Example 11-4 Preparation of Compound 11

합성예 1-4의 화합물 7-3을 화합물 11-2로, 화합물 7-C를 화합물 11-C (3-methyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 11-2, Compound 7-C with Compound 11-C (3-methyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 88.92; H, 6.67; N, 4.41 [M+]:633
Elemental Analysis: C, 88.92; H, 6.67; N, 4.41 [M < + >]: 633

[[ 합성예Synthetic example 12] 화합물 12의 제조 12] Preparation of Compound 12

[합성예 12-1] 화합물 12-1의 제조 Synthesis Example 12-1 Preparation of Compound 12-1

합성예 1-1의 화합물 7-A를 화합물 12-A (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-A of Synthesis Example 1-1 was replaced with compound 12-A (4-isopropyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 12-2] 화합물 12-2의 제조 Synthesis Example 12-2 Preparation of Compound 12-2

합성예 1-2의 화합물 7-1을 화합물 12-1로, 화합물 7-B를 화합물 12-B(bromoethene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 12-1, and Compound 7-B was replaced with Compound 12-B (bromoethene), and the synthesis was carried out using the same method as the synthesis of Compound 7-2.

[합성예 12-3] 화합물 12-3의 제조 Synthesis Example 12-3 Preparation of Compound 12-3

합성예 1-3의 화합물 7-2를 화합물 12-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 12-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 12-4] 화합물 12의 제조 Synthesis Example 12-4 Preparation of Compound 12

합성예 1-4의 화합물 7-3을 화합물 12-3으로, 화합물 7-C를 화합물 12-C (4-methyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 12-3, Compound 7-C was replaced with Compound 12-C (4-methyl-N- (4- (trimethylsilyl) phenyl) aniline), and Compound 7 ( It synthesize | combined using the method similar to the synthesis | combination of synthesis example 1-4).

Elemental Analysis: C, 84.94; H, 7.13; N, 3.96; Si, 3.97 [M+]:706
Elemental Analysis: C, 84.94; H, 7.13; N, 3.96; Si, 3.97 [M < + >]: 706

[[ 합성예Synthetic example 13] 화합물 16의 제조 13] Preparation of Compound 16

[합성예 13-1] 화합물 16-1의 제조 Synthesis Example 13-1 Preparation of Compound 16-1

합성예 1-1의 화합물 7-A를 화합물 16-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with Compound 16-A (N-phenylnaphthalen-2-amine), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 13-2] 화합물 16-2의 제조 Synthesis Example 13-2 Preparation of Compound 16-2

합성예 1-2의 화합물 7-1을 화합물 16-1로, 화합물 7-B를 화합물 16-B(bromophenyl)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 16-1, Compound 7-B with Compound 16-B (bromophenyl), and the synthesis was carried out using the same method as the synthesis of Compound 7-2.

[합성예 13-3] 화합물 16-3의 제조 Synthesis Example 13-3 Preparation of Compound 16-3

합성예 1-3의 화합물 7-2를 화합물 16-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 16-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 13-4] 화합물 16의 제조 Synthesis Example 13-4 Preparation of Compound 16

합성예 1-4의 화합물 7-3을 화합물 16-3으로, 화합물 7-C를 화합물 16-C (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 16-3, Compound 7-C was replaced with Compound 16-C (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 7 (Synthesis) It synthesize | combined using the method similar to the synthesis of Example 1-4).

Elemental Analysis: C, 90.11; H, 6.45; N, 3.45 [M+]:812
Elemental Analysis: C, 90.11; H, 6.45; N, 3.45 [M < + >]: 812

[[ 합성예Synthetic example 14] 화합물 17의 제조 14] Preparation of Compound 17

[합성예 14-1] 화합물 17-1의 제조 Synthesis Example 14-1 Preparation of Compound 17-1

합성예 1-1의 화합물 7-A를 화합물 17-A (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Synthesis of Compound 7-1 by replacing Compound 7-A of Synthesis Example 1-1 with Compound 17-A (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) It could be synthesized using the same method as.

[합성예 14-2] 화합물 17-2의 제조 Synthesis Example 14-2 Preparation of Compound 17-2

합성예 1-2의 화합물 7-1을 화합물 17-1로, 화합물 7-B를 화합물 17-B (bromophenyl)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 17-1, and Compound 7-B was replaced with Compound 17-B (bromophenyl), and the synthesis was carried out using the same method as the synthesis of Compound 7-2.

[합성예 14-3] 화합물 17-3의 제조 Synthesis Example 14-3 Preparation of Compound 17-3

합성예 1-3의 화합물 7-2를 화합물 17-2로 대체하고, 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 17-2, and was synthesized using the same method as the synthesis of Compound 7-3.

[합성예 14-4] 화합물 17의 제조 Synthesis Example 14-4 Preparation of Compound 17

합성예 1-4의 화합물 7-3을 화합물 17-3으로, 화합물 7-C를 화합물 17-C (11,11-dimethyl-N-phenyl-11H-benzo[b]fluoren-2-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 to Compound 17-3, Compound 7-C to Compound 17-C (11,11-dimethyl-N-phenyl-11H-benzo [b] fluoren-2-amine) Instead, it could be synthesized using the same method as the synthesis of Compound 7 (Synthesis Example 1-4).

Elemental Analysis: C, 90.98; H, 6.23; N, 2.79 [M+]:1002
Elemental Analysis: C, 90.98; H, 6.23; N, 2.79 [M < + >]: 1002

[[ 합성예Synthetic example 15] 화합물 18의 제조 15] Preparation of Compound 18

[합성예 15-1] 화합물 18-1의 제조 Synthesis Example 15-1 Preparation of Compound 18-1

합성예 1-1의 화합물 7-A를 화합물 18-A (diphenylamine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 18-A (diphenylamine), and could be synthesized using the same method as the synthesis of Compound 7-1.

[합성예 15-2] 화합물 18-2의 제조 Synthesis Example 15-2 Preparation of Compound 18-2.

합성예 1-2의 화합물 7-1을 화합물 18-1로, 화합물 7-B를 화합물 18-B (bromophynyl)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 18-1, and Compound 7-B was replaced with Compound 18-B (bromophynyl), and the synthesis was carried out using the same method as the synthesis of Compound 7-2.

[합성예 15-3] 화합물 18-3의 제조 Synthesis Example 15-3 Preparation of Compound 18-3

합성예 1-3의 화합물 7-2를 화합물 18-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 18-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 15-4] 화합물 18의 제조 Synthesis Example 15-4 Preparation of Compound 18

합성예 1-4의 화합물 7-3을 화합물 18-3으로, 화합물 7-C를 화합물 18-C (47,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 to Compound 18-3, Compound 7-C to Compound 18-C (47,7-dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine) Instead, it could be synthesized using the same method as the synthesis of Compound 7 (Synthesis Example 1-4).

Elemental Analysis: C, 91.05; H, 5.58; N, 3.37 [M+]: 830
Elemental Analysis: C, 91.05; H, 5.58; N, 3.37 [M < + >]: 830

[[ 합성예Synthetic example 16] 화합물 37의 제조 16] Preparation of Compound 37

[합성예 16-1] 화합물 37-1의 제조 Synthesis Example 16-1 Preparation of Compound 37-1

합성예 1-1의 화합물 7-A를 화합물 37-A (diphenylamine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 37-A (diphenylamine), and could be synthesized using the same method as the synthesis of Compound 7-1.

[합성예 16-2] 화합물 37-2의 제조 Synthesis Example 16-2 Preparation of Compound 37-2

합성예 1-2의 화합물 7-1를 화합물 37-1로, 화합물 7-B를 화합물 37-B (4-bromobiphenyl)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 37-1, and Compound 7-B was replaced with Compound 37-B (4-bromobiphenyl), and it could be synthesized using the same method as the synthesis of Compound 7-2. there was.

[합성예 16-3] 화합물 37-3의 제조 Synthesis Example 16-3 Preparation of Compound 37-3

합성예 1-3의 화합물 7-2를 화합물 37-2로 대체하고, 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 37-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 16-4] 화합물 37의 제조 Synthesis Example 16-4 Preparation of Compound 37

합성예 1-4의 화합물 7-3을 화합물 37-3으로, 화합물 7-C를 화합물 37-C (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 37-3, Compound 7-C was replaced with Compound 37-C (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 7 (Synthesis) It synthesize | combined using the method similar to the synthesis of Example 1-4).

Elemental Analysis: C, 90.55; H, 6.39; N, 3.06 [M+]:914
Elemental Analysis: C, 90.55; H, 6.39; N, 3.06 [M < + >]: 914

[[ 합성예Synthetic example 17] 화합물 38의 제조 17] Preparation of Compound 38

[합성예 17-1] 화합물 38-1의 제조 Synthesis Example 17-1 Preparation of Compound 38-1

합성예 1-1의 화합물 7-A를 화합물 38-A (N-phenylphenanthren-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with Compound 38-A (N-phenylphenanthren-2-amine), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 17-2] 화합물 38-2의 제조 Synthesis Example 17-2 Preparation of Compound 38-2.

합성예 1-2의 화합물 7-1을 화합물 38-1로, 화합물 7-B를 화합물 38-B (4-bromobiphenyl)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 38-1, and Compound 7-B was replaced with Compound 38-B (4-bromobiphenyl), and it was synthesized using the same method as the synthesis of Compound 7-2. there was.

[합성예 17-3] 화합물 38-3의 제조 Synthesis Example 17-3 Preparation of Compound 38-3

합성예 1-3의 화합물 7-2를 화합물 38-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 38-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 17-4] 화합물 38의 제조 Synthesis Example 17-4 Preparation of Compound 38

합성예 1-4의 화합물 7-3을 화합물 38-3으로, 화합물 7-C를 화합물 38-C (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replacing compound 7-3 of Synthesis Example 1-4 with compound 38-3, compound 7-C with compound 38-C (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), compound It synthesize | combined using the method similar to the synthesis of 7 (synthesis example 1-4).

Elemental Analysis: C, 91.83; H, 5.46; N, 2.71 [M+]:1032
Elemental Analysis: C, 91.83; H, 5.46; N, 2.71 [M < + >]: 1032

[[ 합성예Synthetic example 18] 화합물 39의 제조 18] Preparation of Compound 39

[합성예 18-1] 화합물 39-1의 제조 Synthesis Example 18-1 Preparation of Compound 39-1

합성예 1-1의 화합물 7-A를 화합물 39-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-3-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Synthesis of Compound 7-1 by replacing Compound 7-A of Synthesis Example 1-1 with Compound 39-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-3-amine) It could be synthesized using the same method as.

[합성예 18-2] 화합물 39-2의 제조 Synthesis Example 18-2 Preparation of Compound 39-2

합성예 1-2의 화합물 7-1을 화합물 39-1로, 화합물 7-B를 39-B (4-bromobiphenyl)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 39-1, and Compound 7-B was replaced with 39-B (4-bromobiphenyl), and it was synthesized using the same method as the synthesis of Compound 7-2. .

[합성예 18-3] 화합물 39-3의 제조 Synthesis Example 18-3 Preparation of Compound 39-3

합성예 1-3의 화합물 7-2를 화합물 39-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 39-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 18-4] 화합물 39의 제조 Synthesis Example 18-4 Preparation of Compound 39

합성예 1-4의 화합물 7-3을 화합물 39-3으로, 화합물 7-C를 화합물 39-C (N,9,9-triphenyl-9H-fluoren-3-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-3 of Synthesis Example 1-4 was replaced with Compound 39-3, Compound 7-C was replaced with Compound 39-C (N, 9,9-triphenyl-9H-fluoren-3-amine), and Compound 7 ( It synthesize | combined using the method similar to the synthesis | combination of synthesis example 1-4).

Elemental Analysis: C, 92.27; H, 5.44; N, 2.29 [M+]:1222
Elemental Analysis: C, 92.27; H, 5.44; N, 2.29 [M < + >]: 1222

[[ 합성예Synthetic example 19] 화합물 40의 제조 19] Preparation of Compound 40

[합성예 19-1] 화합물 40-1의 제조 Synthesis Example 19-1 Preparation of Compound 40-1

합성예 1-1의 화합물 7-A를 화합물 40-A (4-methyl-N-phenylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 40-A (4-methyl-N-phenylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 19-2] 화합물 40-2의 제조 Synthesis Example 19-2 Preparation of Compound 40-2

합성예 1-2의 화합물 7-1을 화합물 40-1로, 화합물 7-B를 화합물 40-B (2-bromonaphthalene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 could be replaced with Compound 40-1, Compound 7-B with Compound 40-B (2-bromonaphthalene), and synthesized using the same method as the synthesis of Compound 7-2. there was.

[합성예 19-3] 화합물 40-3의 제조 Synthesis Example 19-3 Preparation of Compound 40-3

합성예 1-3의 화합물 7-2를 화합물 40-2로 대체하고, 화합물7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 40-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 19-4] 화합물 40의 제조 Synthesis Example 19-4 Preparation of Compound 40

합성예 1-4의 화합물 7-3을 화합물 40-3으로, 화합물 7-C를 화합물 40-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 40-3, Compound 7-C with Compound 40-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 90.61; H, 6.03; N, 3.35 [M+]:834
Elemental Analysis: C, 90.61; H, 6.03; N, 3.35 [M < + >]: 834

[[ 합성예Synthetic example 20] 화합물 41의 제조 20] Preparation of Compound 41

합성예 19에서 화합물 40-A를 화합물 41-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 40-C를 화합물 41-C (diphenylamine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Elemental Analysis: C, 90.45; H, 6.31; N, 3.25 [M+]:862
In Synthesis Example 19, Compound 40-A was replaced by Compound 41-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 40-C was replaced by Compound 41-C (diphenylamine) Synthesis was carried out using the same method as the synthesis of 40. Elemental Analysis: C, 90.45; H, 6.31; N, 3.25 [M < + >]: 862

[[ 합성예Synthetic example 21] 화합물 42의 제조 21] Preparation of Compound 42

합성예 19에서 화합물 19-A를 화합물 42-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 19-C를 화합물 42-C (4-tert-butyl-N-phenylaniline)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced with Compound 42-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 19-C was replaced with Compound 42-C (4-tert-butyl-N -phenylaniline), using the same method as the synthesis of Compound 40.

Elemental Analysis: C, 90.15; H, 6.80; N, 3.05 [M+]:918
Elemental Analysis: C, 90.15; H, 6.80; N, 3.05 [M < + >]: 918

[[ 합성예Synthetic example 22] 화합물 43의 제조 22] Preparation of Compound 43

합성예 19에서 화합물 19-A를 화합물 43-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 19-C를 화합물 43-C (diphenylamine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced by Compound 43-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), and Compound 19-C was replaced by Compound 43-C (diphenylamine) Thus, it could be synthesized using the same method as in the synthesis of compound 40.

Elemental Analysis: C, 91.33; H, 5.49; N, 3.18 [M+]:880
Elemental Analysis: C, 91.33; H, 5.49; N, 3.18 [M < + >]: 880

[[ 합성예Synthetic example 23] 화합물 44의 제조 23] Preparation of Compound 44

합성예 19에서 화합물 19-A를 화합물 44-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 19-C를 화합물 44-C (dip-tolylamine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced by Compound 44-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), and 19-C was replaced by Compound 44-C (dip-tolylamine) Alternatively, it could synthesize using the same method as the synthesis of compound 40.

Elemental Analysis: C, 91.33; H, 5.49; N, 3.18 [M+]:880
Elemental Analysis: C, 91.33; H, 5.49; N, 3.18 [M < + >]: 880

[[ 합성예Synthetic example 24] 화합물 45의 제조. 24] Preparation of Compound 45.

합성예 19에서 화합물 19-A를 화합물 45-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 19-C를 화합물 45-C (diphenylamine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced with Compound 45-A (N- (4-tert-butylphenyl) -3-methylaniline), and 19-C was replaced with Compound 45-C (diphenylamine) to obtain Compound 40. Synthesis was carried out using the same method as synthesis.

Elemental Analysis: C, 90.61; H, 6.03; N, 3.35 [M+]:834
Elemental Analysis: C, 90.61; H, 6.03; N, 3.35 [M < + >]: 834

[[ 합성예Synthetic example 25] 화합물 46의 제조 25] Preparation of Compound 46

합성예 19에서 화합물 19-A를 화합물 46-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 19-C를 화합물 46-C (diphenylamine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced by Compound 46-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and Compound 19-C was replaced by Compound 46-C (diphenylamine) Thus, it could be synthesized using the same method as in the synthesis of compound 40.

Elemental Analysis: C, 87.40; H, 6.32; N, 3.14; Si, 3.14 [M+]:892
Elemental Analysis: C, 87.40; H, 6.32; N, 3.14; Si, 3.14 [M < + >]: 892

[[ 합성예Synthetic example 26] 화합물 47의 제조 26] Preparation of Compound 47

합성예 19에서 화합물 19-A를 화합물 47-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 19-C를 화합물 47-C (diphenylamine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced with Compound 47-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and Compound 19-C was replaced with Compound 47- Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 40.

Elemental Analysis: C, 91.60; H, 5.48; N, 2.93 [M+]:956
Elemental Analysis: C, 91.60; H, 5.48; N, 2.93 [M < + >]: 956

[[ 합성예Synthetic example 27] 화합물 48의 제조 27] Preparation of Compound 48

합성예 19에서 화합물 19-A를 화합물 48-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 19-C를 화합물 48-C (diphenylamine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced by Compound 48-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and Compound 19-C was replaced by Compound 48- Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 40.

Elemental Analysis: C, 91.58; H, 5.41; N, 3.01 [M+]:930
Elemental Analysis: C, 91.58; H, 5.41; N, 3.01 [M < + >]: 930

[[ 합성예Synthetic example 28] 화합물 49의 제조 28] Preparation of Compound 49

합성예 19에서 화합물 19-A를 화합물 49-A (N-(4-isopropylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 19-C를 화합물 49-C (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced by Compound 49-A (N- (4-isopropylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), and Compound 19-C was replaced by Compound 49-C ( 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 40.

Elemental Analysis: C, 91.29; H, 6.01; N, 2.70 [M+]:1038
Elemental Analysis: C, 91.29; H, 6.01; N, 2.70 [M +]: 1038

[[ 합성예Synthetic example 29] 화합물 50의 제조 29] Preparation of Compound 50

합성예 19에서 화합물 19-A를 화합물 50-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 19-C를 화합물 50-C (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced by Compound 50-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 19-C was replaced by Compound 50-C (9,9- Substituted with dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of compound 40.

Elemental Analysis: C, 91.74; H, 5.58; N, 2.67 [M+]:1046
Elemental Analysis: C, 91.74; H, 5.58; N, 2.67 [M < + >]: 1046

[[ 합성예Synthetic example 30] 화합물 51의 제조 30] Preparation of Compound 51

합성예 19에서 화합물 19-A를 화합물 51-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 19-C를 화합물 51-C (N-phenylnaphthalen-2-amine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced with Compound 51-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 19-C was replaced with Compound 51-C (N-phenylnaphthalen- 2-amine) could be synthesized using the same method as the synthesis of compound 40.

Elemental Analysis: C, 91.58; H, 5.41; N, 3.01 [M+]:930
Elemental Analysis: C, 91.58; H, 5.41; N, 3.01 [M < + >]: 930

[[ 합성예Synthetic example 31] 화합물 52의 제조 31] Preparation of Compound 52

합성예 19에서 화합물 19-A를 화합물 52-A (N-(4-tert-butylphenyl)-11,11-dimethyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 19-C를 화합물 52-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced with Compound 52-A (N- (4-tert-butylphenyl) -11,11-dimethyl-11H-benzo [a] fluoren-9-amine) and Compound 19-C Was replaced with compound 52-C (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of compound 40.

Elemental Analysis: C, 91.40; H, 6.21; N, 2.40 [M+]:1068
Elemental Analysis: C, 91.40; H, 6.21; N, 2.40 [M < + >]: 1068

[[ 합성예Synthetic example 32] 화합물 53의 제조 32] Preparation of Compound 53

합성예 19에서 화합물 19-A를 화합물 53-A (11,11-dimethyl-N-phenyl-11H-benzo[b]fluoren-2-amine)로 대체하고, 화합물 19-C를 화합물 53-C (N-(4-isopropylphenyl)-11,11-dimethyl-11H-benzo[b]fluoren-2-amine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced with Compound 53-A (11,11-dimethyl-N-phenyl-11H-benzo [b] fluoren-2-amine), and Compound 19-C was replaced with Compound 53-C ( Substituted with N- (4-isopropylphenyl) -11,11-dimethyl-11H-benzo [b] fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 40.

Elemental Analysis: C, 91.86; H, 5.62; N, 2.52 [M+]:1109
Elemental Analysis: C, 91.86; H, 5.62; N, 2.52 [M < + >]: 1109

[[ 합성예Synthetic example 33] 화합물 54의 제조 33] Preparation of Compound 54

합성예 19에서 화합물 19-A를 화합물 54-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 19-C를 화합물 54-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 40의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 19, Compound 19-A was replaced with Compound 54-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and 19-C was replaced with Compound 54-C (11,11-dimethyl -N-phenyl-11H-benzo [a] fluoren-9-amine) could be synthesized using the same method as the synthesis of Compound 40.

Elemental Analysis: C, 91.74; H, 5.58; N, 2.67 [M+]:1046
Elemental Analysis: C, 91.74; H, 5.58; N, 2.67 [M < + >]: 1046

[[ 합성예Synthetic example 34] 화합물 55의 제조 34] Preparation of Compound 55

[합성예 34-1] 화합물 55-1의 제조 Synthesis Example 34-1 Preparation of Compound 55-1

합성예 1-1의 화합물 7-A를 화합물 55-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with Compound 55-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 34-2] 화합물 55-2의 제조 Synthesis Example 34-2 Preparation of Compound 55-2.

합성예 1-2의 화합물 7-1을 화합물 55-1로, 화합물 7-B를 화합물 55-B (9-bromophenanthrene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced with Compound 55-1, and Compound 7-B was replaced with Compound 55-B (9-bromophenanthrene), and it was synthesized using the same method as the synthesis of Compound 7-2. there was.

[합성예 34-3] 화합물 55-3의 제조 Synthesis Example 34-3 Preparation of Compound 55-3

합성예 1-3의 화합물 7-2를 화합물 55-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 55-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 34-4] 화합물 55의 제조 Synthesis Example 34-4 Preparation of Compound 55

합성예 1-4의 화합물 7-3을 화합물 55-3으로, 화합물 7-C를 화합물 55-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 55-3, Compound 7-C with Compound 55-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 91.49; H, 5.55; N, 2.96 [M+]:944
Elemental Analysis: C, 91.49; H, 5.55; N, 2.96 [M < + >]: 944

[[ 합성예Synthetic example 35] 화합물 56의 제조 35] Preparation of Compound 56

합성예 34에서 화합물 55-A를 화합물 56-A (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하고, 화합물 55-C를 화합물 56-C (4-tert-butyl-N-phenylaniline)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 56-A (7,7-dimethyl-N-phenyl-7H-benzo [de] anthracen-9-amine), and Compound 55-C was replaced with Compound 56-C ( 4-tert-butyl-N-phenylaniline) could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 90.98; H, 6.23; N, 2.79 [M+]:1002
Elemental Analysis: C, 90.98; H, 6.23; N, 2.79 [M < + >]: 1002

[[ 합성예Synthetic example 36] 화합물 57의 제조 36] Preparation of Compound 57

합성예 34에서 화합물 55-A를 화합물 57-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 57-C (N-p-tolylnaphthalen-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, compound 55-A was replaced with compound 57-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 55-C was replaced with compound 57-C (Np-tolylnaphthalen-2- amine) could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.10; H, 5.28; N, 2.62 [M+]:1068
Elemental Analysis: C, 92.10; H, 5. 28; N, 2.62 [M < + >]: 1068

[[ 합성예Synthetic example 37] 화합물 58의 제조 37] Preparation of Compound 58

합성예 34에서 화합물 55-A를 화합물 58-A (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 55-C를 화합물 58-C (4-tert-butyl-N-p-tolylaniline)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 58-A (4-isopropyl-Np-tolylaniline), and Compound 55-C was replaced with Compound 58-C (4-tert-butyl-Np-tolylaniline), Synthesis was carried out using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 90.87; H, 6.30; N, 2.83 [M+]:990
Elemental Analysis: C, 90.87; H, 6. 30; N, 2.83 [M < + >]: 990

[[ 합성예Synthetic example 38] 화합물 59의 제조 38] Preparation of Compound 59

합성예 34에서 화합물 55-A를 화합물 59-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 55-C를 화합물 59-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, compound 55-A was replaced with compound 59-A (N-phenylnaphthalen-2-amine), and compound 55-C was replaced with compound 59-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 91.73; H, 5.53; N, 2.74 [M+] :1020
Elemental Analysis: C, 91.73; H, 5.53; N, 2.74 [M +]: 1020

[[ 합성예Synthetic example 39] 화합물 60의 제조 39] Preparation of Compound 60

합성예 34에서 화합물 55-A를 화합물 60-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 55-C를 화합물 60-C (N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다. In Synthesis Example 34, compound 55-A was replaced with compound 60-A (N-phenylnaphthalen-1-amine), and compound 55-C was replaced with compound 60-C (N- (4- (trimethylsilyl) phenyl) naphthalen-1- amine), using the same method as for the synthesis of compound 55 .

Elemental Analysis: C, 89.15; H, 5.44; N, 2.70; Si, 2.71 [M+] : 1036
Elemental Analysis: C, 89.15; H, 5.44; N, 2.70; Si, 2.71 [M < + >]: 1036

[[ 합성예Synthetic example 40] 화합물 61의 제조 40] Preparation of Compound 61

합성예 34에서 화합물 55-A를 화합물 61-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 55-C를 화합물 (61-C diphenylamine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 61-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 55-C was replaced with Compound (61-C diphenylamine) Synthesis was carried out using the same method as the synthesis of 55.

Elemental Analysis: C, 91.02; H, 6.07; N, 2.91 [M+]:962
Elemental Analysis: C, 91.02; H, 6.07; N, 2.91 [M < + >]: 962

[[ 합성예Synthetic example 41] 화합물 62의 제조 41] Preparation of Compound 62

합성예 34에서 화합물 55-A를 화합물 62-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 62-C (diphenylamine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 62-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine) and Compound 55-C was replaced with Compound 62-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 91.80; H, 5.34; N, 2.85 [M+]:980
Elemental Analysis: C, 91.80; H, 5.34; N, 2.85 [M < + >]: 980

[[ 합성예Synthetic example 42] 화합물 63의 제조 42] Preparation of Compound 63

합성예 34에서 화합물 55-A를 화합물 63-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 55-C를 화합물 63-C (diphenylamine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced by Compound 63-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), and Compound 55-C was replaced by Compound 63-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 91.80; H, 5.34; N, 2.85 [M+]:980
Elemental Analysis: C, 91.80; H, 5.34; N, 2.85 [M < + >]: 980

[[ 합성예Synthetic example 43] 화합물 64의 제조 43] Preparation of Compound 64

합성예 34에서 화합물 55-A를 화합물 64-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 55-C를 화합물 64-C (diphenylamine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 64-A (N- (4-tert-butylphenyl) -3-methylaniline), and Compound 55-C was replaced with Compound 64-C (diphenylamine), Compound 55 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 91.18; H, 5.82; N, 3.00 [M+] : 934Elemental Analysis: C, 91.18; H, 5. 82; N, 3.00 [M < + >]: 934

[[ 합성예Synthetic example 44] 화합물 65의 제조 44] Preparation of Compound 65

합성예 34에서 화합물 55-A를 화합물 65-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 55-C를 화합물 65-C (diphenylamine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 65-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and Compound 55-C was replaced with Compound 65-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 88.26; H, 6.09; N, 2.82; Si, 2.83 [M+]:992
Elemental Analysis: C, 88.26; H, 6.09; N, 2.82; Si, 2.83 [M < + >]: 992

[[ 합성예Synthetic example 45] 화합물 66의 제조 45] Preparation of Compound 66

합성예 34에서 화합물 55-A를 화합물 66-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 55-C를 화합물 66-C (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, compound 55-A was replaced with compound 66-A (N-phenylbiphenyl-4-amine), and compound 55-C was replaced with compound 66-C (9,9-dimethyl-N-phenyl-9H-fluoren- 2-amine) could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.01; H, 5.34; N, 2.65 [M+]:1056
Elemental Analysis: C, 92.01; H, 5.34; N, 2.65 [M +]: 1056

[[ 합성예Synthetic example 46] 화합물 67의 제조 46] Preparation of Compound 67

합성예 34에서 화합물 55-A를 화합물 67-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 67-C (diphenylamine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 67-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and Compound 55-C was replaced with Compound 67- Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.01; H, 5.34; N, 2.65 [M+]:1056
Elemental Analysis: C, 92.01; H, 5.34; N, 2.65 [M +]: 1056

[[ 합성예Synthetic example 47] 화합물 68의 제조 47] Preparation of Compound 68

합성예 34에서 화합물 55-A를 화합물 68-A (4-tert-butyl-N-phenylaniline)로 대체하고, 화합물 55-C를 화합물 68-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, compound 55-A was replaced with compound 68-A (4-tert-butyl-N-phenylaniline), and compound 55-C was replaced with compound 68-C (11,11-dimethyl-N-phenyl-11H- Substituted with benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 91.68; H, 5.75; N, 2.58 [M+]:1086
Elemental Analysis: C, 91.68; H, 5.75; N, 2.58 [M < + >]: 1086

[[ 합성예Synthetic example 48] 화합물 69의 제조 48] Preparation of Compound 69

합성예 34에서 화합물 55-A를 화합물 69-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 55-C를 화합물 69-C (N-phenylbenzo[d]thiazol-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 55-A with compound 69-A (N-phenylnaphthalen-2-amine) in Synthesis Example 34 and replaced compound 55-C with compound 69-C (N-phenylbenzo [d] thiazol-2-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 87.71; H, 4.67; N, 4.32; S, 3.30 [M+]:971
Elemental Analysis: C, 87.71; H, 4.67; N, 4. 32; S, 3.30 [M +]: 971

[[ 합성예Synthetic example 49] 화합물 70의 제조 49] Preparation of Compound 70

합성예 34에서 화합물 55-A를 화합물 70-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 70-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다. In Synthesis Example 34, compound 55-A was replaced with compound 70-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 55-C was replaced with compound 70-C (11,11- Substituted with dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 55 .

Elemental Analysis: C, 92.11; H, 5.45; N, 2.44 [M+]:1046
Elemental Analysis: C, 92.11; H, 5.45; N, 2.44 [M < + >]: 1046

[[ 합성예Synthetic example 50] 화합물 71의 제조 50] Preparation of Compound 71

합성예 34에서 화합물 55-A를 화합물 71-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 71-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 71-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and Compound 55-C was replaced with Compound 71-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 91.56; H, 6.04; N, 2.40 [M+]:1166
Elemental Analysis: C, 91.56; H, 6.04; N, 2.40 [M < + >]: 1166

[[ 합성예Synthetic example 51] 화합물 72의 제조 51] Preparation of Compound 72

합성예 34에서 화합물 55-A를 화합물 72-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 72-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, compound 55-A was replaced with compound 72-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 55-C was replaced with compound 72-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine) could be substituted using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.11; H, 5.45; N, 2.44 [M+]:1046
Elemental Analysis: C, 92.11; H, 5.45; N, 2.44 [M < + >]: 1046

[[ 합성예Synthetic example 52] 화합물 73의 제조 52] Preparation of Compound 73

합성예 34에서 화합물 55-A를 화합물 73-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 55-C를 화합물 73-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 73-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and Compound 55-C was replaced with Compound 73-C ( Substituted with 11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.42; H, 5.33; N, 2.25 [M+]:1246
Elemental Analysis: C, 92.42; H, 5. 33; N, 2.25 [M < + >]: 1246

[[ 합성예Synthetic example 53] 화합물 74의 제조 53] Preparation of Compound 74

합성예 34에서 화합물 55-A를 화합물 74-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 74-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 74-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and Compound 55-C was replaced with Compound 74- Substituted with C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 91.81; H, 5.86; N, 2.33 [M+]:1202
Elemental Analysis: C, 91.81; H, 5. 86; N, 2.33 [M < + >]: 1202

[[ 합성예Synthetic example 54] 화합물 75의 제조 54] Preparation of Compound 75

합성예 34에서 화합물 55-A를 화합물 75-A (7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 55-C를 화합물 75-C (N-(4-tert-butylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 75-A (7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine), and Compound 55-C was replaced with Compound 75-C ( Substituted with N- (4-tert-butylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 91.91; H, 5.88; N, 2.21 [M+]:1266
Elemental Analysis: C, 91.91; H, 5.88; N, 2.21 [M < + >]: 1266

[[ 합성예Synthetic example 55] 화합물 76의 제조 55] Preparation of Compound 76

합성예 34에서 화합물 55-A를 화합물 76-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 55-C를 화합물 76-C (N-phenylbiphenyl-4-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 76-A (N-phenylnaphthalen-2-amine), and Compound 55-C was replaced with Compound 76-C (N-phenylbiphenyl-4-amine) to give Compound 55 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 92.28; H, 5.10; N, 2.62 [M+]:1066
Elemental Analysis: C, 92.28; H, 5. 10; N, 2.62 [M +]: 1066

[[ 합성예Synthetic example 56] 화합물 77의 제조 56] Preparation of Compound 77

합성예 34에서 화합물 55-A를 화합물 77-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 77-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 77-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 55-C was replaced with Compound 77-C (N, 9, 9-triphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.43; H, 5.28; N, 2.29 [M+]:1220
Elemental Analysis: C, 92.43; H, 5. 28; N, 2.29 [M < + >]: 1220

[[ 합성예Synthetic example 57] 화합물 78의 제조 57] Preparation of Compound 78

합성예 34에서 화합물 55-A를 화합물 78-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 78-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, compound 55-A was replaced with compound 78-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 55-C was replaced with compound 78-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.54; H, 5.46; N, 2.00 [M+]:1400
Elemental Analysis: C, 92.54; H, 5.46; N, 2.00 [M +]: 1400

[[ 합성예Synthetic example 58] 화합물 79의 제조 58] Preparation of Compound 79

합성예 34에서 화합물 55-A를 화합물 79-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 55-C를 화합물 79-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 79-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 55-C was replaced with Compound 79-C (4- (naphthalen -1-yl) -N-phenylaniline) could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.19; H, 5.28; N, 2.53 [M+]:1106
Elemental Analysis: C, 92.19; H, 5. 28; N, 2.53 [M < + >]: 1106

[[ 합성예Synthetic example 59] 화합물 80의 제조 59] Preparation of Compound 80

합성예 34에서 화합물 55-A를 화합물 80-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 55-C를 화합물 80-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 80-A (N-phenylfluoranthen-3-amine), and Compound 55-C was replaced with Compound 80-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.52; H, 5.06; N, 2.42 [M+]:1154
Elemental Analysis: C, 92.52; H, 5.06; N, 2.42 [M < + >]: 1154

[[ 합성예Synthetic example 60] 화합물 81의 제조 60] Preparation of Compound 81

합성예 34에서 화합물 55-A를 화합물 81-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 55-C를 화합물 81-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하여, 화합물 55의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 34, Compound 55-A was replaced with Compound 81-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and Compound 55-C was replaced with Compound 81-C ( N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) could be synthesized using the same method as the synthesis of Compound 55.

Elemental Analysis: C, 92.34; H, 5.52; N, 2.13 [M+]:1312
Elemental Analysis: C, 92.34; H, 5.52; N, 2.13 [M < + >]: 1312

[[ 합성예Synthetic example 61] 화합물 82의 제조 61] Preparation of Compound 82

[합성예 61-1] 화합물 82-1의 제조 Synthesis Example 61-1 Preparation of Compound 82-1

합성예 1-1의 화합물 7-A를 화합물 82-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 82-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 61-2] 화합물 82-2의 제조 Synthesis Example 61-2 Preparation of Compound 82-2.

합성예 1-2의 화합물 7-1을 화합물 82-1로, 화합물 7-B를 화합물 82-B (2-bromo-9,9-dimethyl-9H-fluorene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced by Compound 82-1, Compound 7-B by Compound 82-B (2-bromo-9,9-dimethyl-9H-fluorene), Synthesis was carried out using the same method as synthesis.

[합성예 61-3] 화합물 82-3의 제조 Synthesis Example 61-3 Preparation of Compound 82-3

합성예 1-3의 화합물 7-2를 화합물 82-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with compound 82-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 61-4] 화합물 82의 제조 Synthesis Example 61-4 Preparation of Compound 82

합성예 1-4의 화합물 7-3을 화합물 82-3으로, 화합물 7-C를 화합물 82-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 82-3, Compound 7-C with Compound 82-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 90.37; H, 6.89; N, 2.74 [M+]:1022
Elemental Analysis: C, 90.37; H, 6.89; N, 2.74 [M +]: 1022

[[ 합성예Synthetic example 62] 화합물 83의 제조 62] Preparation of Compound 83

합성예 61에서 화합물 82-A를 화합물 83-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 82-C를 화합물 83-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 83-A (N-phenylnaphthalen-2-amine), and compound 82-C was replaced with compound 83-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.22; H, 6.12; N, 2.66 [M+]:1052
Elemental Analysis: C, 91.22; H, 6. 12; N, 2.66 [M +]: 1052

[[ 합성예Synthetic example 63] 화합물 84의 제조 63] Preparation of Compound 84

합성예 61에서 화합물 82-A를 화합물 84-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 82-C를 화합물 84-C (N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 84-A (N-phenylnaphthalen-1-amine), and compound 82-C was replaced with compound 84-C (N- (4- (trimethylsilyl) phenyl) naphthalen-1- amine), using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 88.72; H, 6.03; N, 2.62; Si, 2.63 [M+]:1068
Elemental Analysis: C, 88.72; H, 6.03; N, 2.62; Si, 2.63 [M < + >]: 1068

[[ 합성예Synthetic example 64] 화합물 85의 제조 64] Preparation of Compound 85

합성예 61에서 화합물 82-A를 화합물 85-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 82-C를 화합물 85-C (diphenylamine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, Compound 82-A was replaced with Compound 85-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 82-C was replaced with Compound 85-C (diphenylamine) It could synthesize | combine using the same method as the synthesis | combination of 82.

Elemental Analysis: C, 90.50; H, 6.68; N, 2.81 [M+]:994
Elemental Analysis: C, 90.50; H, 6.68; N, 2.81 [M < + >]: 994

[[ 합성예Synthetic example 65] 화합물 86의 제조 65] Preparation of Compound 86

합성예 61에서 화합물 82-A를 화합물 86-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 86-C (diphenylamine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, Compound 82-A was replaced by Compound 86-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 82-C was replaced by Compound 86-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.27; H, 5.97; N, 2.76 [M+]:1012
Elemental Analysis: C, 91.27; H, 5.97; N, 2.76 [M < + >]: 1012

[[ 합성예Synthetic example 66] 화합물 87의 제조 66] Preparation of Compound 87

합성예 61에서 화합물 82-A를 화합물 87-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 82-C를 화합물 87-C (diphenylamine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 87-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), and compound 82-C was replaced with compound 87-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.27; H, 5.97; N, 2.76 [M+]:1012
Elemental Analysis: C, 91.27; H, 5.97; N, 2.76 [M < + >]: 1012

[[ 합성예Synthetic example 67] 화합물 88의 제조 67] Preparation of Compound 88

합성예 61에서 화합물 82-A를 화합물 88-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 82-C를 화합물 88-C (diphenylamine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, Compound 82-A was replaced with Compound 88-A (N- (4-tert-butylphenyl) -3-methylaniline), and Compound 82-C was replaced with Compound 88-C (diphenylamine), Compound 82 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 90.64; H, 6.46; N, 2.90 [M+]:966
Elemental Analysis: C, 90.64; H, 6. 46; N, 2.90 [M < + >]: 966

[[ 합성예Synthetic example 68] 화합물 89의 제조 68] Preparation of Compound 89

합성예 61에서 화합물 82-A를 화합물 89-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 82-C를 화합물 89-C (diphenylamine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 89-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and compound 82-C was replaced with compound 89-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 87.85; H, 6.68; N, 2.73; Si, 2.74 [M+]:1024
Elemental Analysis: C, 87.85; H, 6.68; N, 2.73; Si, 2.74 [M < + >]: 1024

[[ 합성예Synthetic example 69] 화합물 90의 제조 69] Preparation of Compound 90

합성예 61에서 화합물 82-A를 화합물 90-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 82-C를 화합물 90-C (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 90-A (N-phenylbiphenyl-4-amine), and compound 82-C was replaced with compound 90-C (9,9-dimethyl-N-phenyl-9H-fluoren- 2-amine) could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.51; H, 5.92; N, 2.57 [M+]:1088
Elemental Analysis: C, 91.51; H, 5.92; N, 2.57 [M < + >]: 1088

[[ 합성예Synthetic example 70] 화합물 91의 제조 70] Preparation of Compound 91

합성예 61에서 화합물 82-A를 화합물 91-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 91-C (diphenylamine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 91-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and compound 82-C was replaced by Compound 91- Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.51; H, 5.92; N, 2.57 [M+]:1088
Elemental Analysis: C, 91.51; H, 5.92; N, 2.57 [M < + >]: 1088

[[ 합성예Synthetic example 71] 화합물 92의 제조 71] Preparation of Compound 92

합성예 61에서 화합물 82-A를 화합물 92-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 82-C를 화합물 92-C (4-tert-butyl-N-phenylaniline)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, Compound 82-A was replaced with Compound 92-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and Compound 82-C was replaced with Compound 92-C ( 4-tert-butyl-N-phenylaniline) could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.20; H, 6.30; N, 2.50 [M+]:1118
Elemental Analysis: C, 91.20; H, 6. 30; N, 2.50 [M < + >]: 1118

[[ 합성예Synthetic example 72] 화합물 93의 제조 72] Preparation of Compound 93

합성예 61에서 화합물 82-A를 화합물 93-A (N-phenylbenzo[d]thiazol-2-amine)로 대체하고, 화합물 82-C를 화합물 93-C (N-phenylnaphthalen-2-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, Compound 82-A was replaced with Compound 93-A (N-phenylbenzo [d] thiazol-2-amine), and Compound 82-C was replaced with Compound 93-C (N-phenylnaphthalen-2-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 87.30; H, 5.32; N, 4.18; S, 3.19 [M+]:1003
Elemental Analysis: C, 87.30; H, 5.32; N, 4.18; S, 3.19 [M +]: 1003

[[ 합성예Synthetic example 73] 화합물 94의 제조 73] Preparation of Compound 94

합성예 61에서 화합물 82-A를 화합물 94-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 94-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 94-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 82-C was replaced with compound 94-C (11,11- Substituted with dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M+]:1178
Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M < + >]: 1178

[[ 합성예Synthetic example 74] 화합물 95의 제조 74] Preparation of Compound 95

합성예 61에서 화합물 82-A를 화합물 95-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 95-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 95-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and compound 82-C was replaced with compound 95-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.11; H, 6.55; N, 2.34 [M+]:1198
Elemental Analysis: C, 91.11; H, 6.55; N, 2.34 [M < + >]: 1198

[[ 합성예Synthetic example 75] 화합물 96의 제조 75] Preparation of Compound 96

합성예 61에서 화합물 82-A를 화합물 96-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 96-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 96-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 82-C was replaced with compound 96-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M+]:1178
Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M < + >]: 1178

[[ 합성예Synthetic example 76] 화합물 97의 제조 76] Preparation of Compound 97

합성예 61에서 화합물 82-A를 화합물 97-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 82-C를 화합물 97-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, Compound 82-A was replaced with Compound 97-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and Compound 82-C was replaced with Compound 97-C ( Substituted with 11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 77] 화합물 98의 제조 77] Preparation of Compound 98

합성예 61에서 화합물 82-A를 화합물 98-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 98-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 98-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and compound 82-C was replaced with compound 98-A. Substituted with C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.37; H, 6.36; N, 2.27 [M+]:1234
Elemental Analysis: C, 91.37; H, 6. 36; N, 2.27 [M < + >]: 1234

[[ 합성예Synthetic example 78] 화합물 99의 제조 78] Preparation of Compound 99

합성예 61에서 화합물 82-A를 화합물 99-A (7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 82-C를 화합물 99-C (N-(4-tert-butylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, Compound 82-A was replaced with Compound 99-A (7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine), and Compound 82-C was replaced with Compound 99-C ( Substituted with N- (4-tert-butylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.49; H, 6.36; N, 2.16 [M+]:1298
Elemental Analysis: C, 91.49; H, 6. 36; N, 2.16 [M < + >]: 1298

[[ 합성예Synthetic example 79] 화합물 100의 제조 79] Preparation of Compound 100

합성예 61에서 화합물 82-A를 화합물 100-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 82-C를 화합물 100-C (5-phenyl-N-phenylbiphenyl-3-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 82-A with compound 100-A (N-phenylnaphthalen-2-amine) in Synthesis Example 61 and replaced compound 82-C with compound 100-C (5-phenyl-N-phenylbiphenyl-3-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.77; H, 5.68; N, 2.55 [M+]:1098
Elemental Analysis: C, 91.77; H, 5.68; N, 2.55 [M < + >]: 1098

[[ 합성예Synthetic example 80] 화합물 101의 제조 80] Preparation of Compound 101

합성예 61에서 화합물 82-A를 화합물 101-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 101-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 101-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 82-C was replaced with compound 101-C (N, 9, 9-triphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.98; H, 5.79; N, 2.23 [M+]:1252
Elemental Analysis: C, 91.98; H, 5.79; N, 2.23 [M < + >]: 1252

[[ 합성예Synthetic example 81] 화합물 102의 제조 81] Preparation of Compound 102

합성예 61에서 화합물 82-A를 화합물 102-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 102-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 102-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 82-C was replaced with compound 102-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 92.14; H, 5.90; N, 1.95 [M+]:1432
Elemental Analysis: C, 92.14; H, 5. 90; N, 1.95 [M < + >]: 1432

[[ 합성예Synthetic example 82] 화합물 103의 제조 82] Preparation of Compound 103

합성예 61에서 화합물 82-A를 화합물 103-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 82-C를 화합물 103-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 103-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 82-C was replaced with compound 103-C (4- (naphthalen -1-yl) -N-phenylaniline) could be synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.70; H, 5.84; N, 2.46 [M+]:1138
Elemental Analysis: C, 91.70; H, 5.84; N, 2.46 [M < + >]: 1138

[[ 합성예Synthetic example 83] 화합물 104의 제조 83] Preparation of Compound 104

합성예 61에서 화합물 82-A를 화합물 104-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 82-C를 화합물 104-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 104-A (N-phenylfluoranthen-3-amine), and compound 82-C was replaced with compound 104-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 92.04; H, 5.60; N, 2.36 [M+]:1186Elemental Analysis: C, 92.04; H, 5.60; N, 2.36 [M < + >]: 1186

[[ 합성예Synthetic example 84] 화합물 105의 제조 84] Preparation of Compound 105

합성예 61에서 화합물 82-A를 화합물 105-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 82-C를 화합물 105-C (4-isopropyl-N-p-tolylaniline)로 대체하여, 화합물 82의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 61, compound 82-A was replaced with compound 105-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and compound 82-C was replaced with compound 105-C ( 4-isopropyl-Np-tolylaniline) was synthesized using the same method as the synthesis of Compound 82.

Elemental Analysis: C, 91.93; H, 5.99; N, 2.08 [M+]:1344
Elemental Analysis: C, 91.93; H, 5.99; N, 2.08 [M +]: 1344

[[ 합성예Synthetic example 85] 화합물 106의 제조 85] Preparation of Compound 106

[합성예 85-1] 화합물 106-1의 제조 Synthesis Example 85-1 Preparation of Compound 106-1.

합성예 1-1의 화합물 7-A를 화합물 106-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 106-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 85-2] 화합물 106-2의 제조 Synthesis Example 85-2 Preparation of Compound 106-2.

합성예 1-2의 화합물 7-1을 화합물 106-1로, 화합물 7-B를 화합물 106-B (9-bromo-11,11-dimethyl-11H-benzo[a]fluorene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Replacing compound 7-1 of Synthesis Example 1-2 with compound 106-1, compound 7-B with compound 106-B (9-bromo-11,11-dimethyl-11H-benzo [a] fluorene), and Synthesis was carried out using the same method as in the synthesis of 7-2.

[합성예 85-3] 화합물 106-3의 제조 Synthesis Example 85-3 Preparation of Compound 106-3

합성예 1-3의 화합물 7-2를 화합물 106-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 106-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 85-4] 화합물 106의 제조 Synthesis Example 85-4 Preparation of Compound 106

합성예 1-4의 화합물 7-3을 화합물 106-3으로, 화합물 7-C를 화합물 106-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 106-3, Compound 7-C with Compound 106-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 90.87; H, 6.64; N, 2.49 [M+]:1122
Elemental Analysis: C, 90.87; H, 6.64; N, 2.49 [M < + >]: 1122

[[ 합성예Synthetic example 86] 화합물 107의 제조 86] Preparation of Compound 107

합성예 85에서 화합물 106-A를 화합물 107-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 106-C를 화합물 107-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 107-A (N-phenylnaphthalen-2-amine), and compound 106-C was replaced with compound 107-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M+]:1152
Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M < + >]: 1152

[[ 합성예Synthetic example 87] 화합물 108의 제조 87] Preparation of Compound 108

합성예 85에서 화합물 106-A를 화합물 108-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 106-C를 화합물 108-C (N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 108-A (N-phenylnaphthalen-1-amine), and compound 106-C was replaced with compound 108-C (N- (4- (trimethylsilyl) phenyl) naphthalen-1- amine), it could be synthesized using the same method as the synthesis of compound 106.

Elemental Analysis: C, 89.34; H, 5.86; N, 2.40; Si, 2.40 [M+]:1168
Elemental Analysis: C, 89.34; H, 5. 86; N, 2.40; Si, 2.40 [M < + >]: 1168

[[ 합성예Synthetic example 88] 화합물 109의 제조 88] Preparation of Compound 109

합성예 85에서 화합물 106-A를 화합물 109-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 106-C를 화합물 109-C (diphenylamine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 109-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 106-C was replaced with Compound 109-C (diphenylamine) Synthesis was carried out using the same method as the synthesis of 106.

Elemental Analysis: C, 91.00; H, 6.44; N, 2.56 [M+]:1094
Elemental Analysis: C, 91.00; H, 6.44; N, 2.56 [M +]: 1094

[[ 합성예Synthetic example 89] 화합물 110의 제조 89] Preparation of Compound 110

합성예 85에서 화합물 106-A를 화합물 110-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 110-C (diphenylamine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced by Compound 110-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine) and Compound 106-C was replaced by Compound 110-C (diphenylamine) Thus, it could be synthesized using the same method as in the synthesis of compound 106.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 90] 화합물 111의 제조 90] Preparation of Compound 111

합성예 85에서 화합물 106-A를 화합물 111-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 106-C를 화합물 111-C (diphenylamine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced by Compound 111-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine) and Compound 106-C was replaced by Compound 111-C (diphenylamine) Thus, it could be synthesized using the same method as in the synthesis of compound 106.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 91] 화합물 112의 제조 91] Preparation of Compound 112

합성예 85에서 화합물 106-A를 화합물 112-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 106-C를 화합물 112-C (diphenylamine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 112-A (N- (4-tert-butylphenyl) -3-methylaniline), and Compound 106-C was replaced with Compound 112-C (diphenylamine), Compound 106 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M+]:1066
Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M +]: 1066

[[ 합성예Synthetic example 92] 화합물 113의 제조 92] Preparation of Compound 113

합성예 85에서 화합물 106-A를 화합물 113-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 106-C를 화합물 113-C (diphenylamine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced by Compound 113-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and Compound 106-C was replaced by Compound 113-C (diphenylamine) Thus, it could be synthesized using the same method as in the synthesis of compound 106.

Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M+]:1124
Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M < + >]: 1124

[[ 합성예Synthetic example 93] 화합물 114의 제조 93] Preparation of Compound 114

합성예 85에서 화합물 106-A를 화합물 114-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 106-C를 화합물 114-C (N-(4-isopropylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 114-A (N-phenylbiphenyl-4-amine), and compound 106-C was replaced with compound 114-C (N- (4-isopropylphenyl) -9,9-dimethyl- 9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.67; H, 6.06; N, 2.27 [M+]:1230
Elemental Analysis: C, 91.67; H, 6.06; N, 2.27 [M < + >]: 1230

[[ 합성예Synthetic example 94] 화합물 115의 제조 94] Preparation of Compound 115

합성예 85에서 화합물 106-A를 화합물 115-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 115-C (diphenylamine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced by Compound 115-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and Compound 106-C was replaced by Compound 115-. Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 106.

Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M+]:1188
Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M < + >]: 1188

[[ 합성예Synthetic example 95] 화합물 116의 제조 95] Preparation of Compound 116

합성예 85에서 화합물 106-A를 화합물 116-A (4-tert-butyl-N-phenylaniline)로 대체하고, 화합물 106-C를 화합물 116-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 116-A (4-tert-butyl-N-phenylaniline), and compound 106-C was replaced with compound 116-C (11,11-dimethyl-N-phenyl-11H- Substituted with benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.59; H, 6.12; N, 2.30 [M+]:1218
Elemental Analysis: C, 91.59; H, 6. 12; N, 2.30 [M < + >]: 1218

[[ 합성예Synthetic example 96] 화합물 117의 제조 96] Preparation of Compound 117

합성예 85에서 화합물 106-A를 화합물 117-A (N-phenylbenzo[d]thiazol-2-amine)로 대체하고, 화합물 106-C를 화합물 117-C (N-phenylnaphthalen-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 117-A (N-phenylbenzo [d] thiazol-2-amine), and Compound 106-C was replaced with Compound 117-C (N-phenylnaphthalen-2-amine) Thus, it could be synthesized using the same method as in the synthesis of compound 106.

Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M+]:1103
Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M +]: 1103

[[ 합성예Synthetic example 97] 화합물 118의 제조 97] Preparation of Compound 118

합성예 85에서 화합물 106-A를 화합물 118-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 118-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 118-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 106-C was replaced with compound 118-C (11,11- dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine) could be substituted using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 98] 화합물 119의 제조 98] Preparation of Compound 119

합성예 85에서 화합물 106-A를 화합물 119-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 119-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 119-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and compound 106-C was replaced with compound 119-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.49; H, 6.36; N, 2.16 [M+]:1298
Elemental Analysis: C, 91.49; H, 6. 36; N, 2.16 [M < + >]: 1298

[[ 합성예Synthetic example 99] 화합물 120의 제조 99] Preparation of Compound 120

합성예 85에서 화합물 106-A를 화합물 120-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 120-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 120-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 106-C was replaced with compound 120-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 100] 화합물 121의 제조 100] Preparation of Compound 121

합성예 85에서 화합물 106-A를 화합물 121-A (11,11-dimethyl-N-(phenyl-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 106-C를 화합물 121-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 121-A (11,11-dimethyl-N- (phenyl-2-yl) -11H-benzo [a] fluoren-9-amine) and Compound 106-C Was replaced with compound 121-C (11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine) to synthesize the same compound as in the synthesis of compound 106. Could.

Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M+]:1378
Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M < + >]: 1378

[[ 합성예Synthetic example 101] 화합물 122의 제조 101] Preparation of Compound 122

합성예 85에서 화합물 106-A를 화합물 122-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 122-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 122-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and Compound 106-C was replaced with Compound 122-A. Substituted with C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.32; H, 6.63; N, 2.05 [M+]:1366
Elemental Analysis: C, 91.32; H, 6.63; N, 2.05 [M < + >]: 1366

[[ 합성예Synthetic example 102] 화합물 123의 제조 102] Preparation of Compound 123

합성예 85에서 화합물 106-A를 화합물 123-A (7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 106-C를 화합물 123-C (N-(4-tert-butylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 123-A (7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine), and Compound 106-C was replaced with Compound 123-C ( Substituted with N- (4-tert-butylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M+]:1398
Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M < + >]: 1398

[[ 합성예Synthetic example 103] 화합물 124의 제조 103] Preparation of Compound 124

합성예 85에서 화합물 106-A를 화합물 124-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 106-C를 화합물 (124-C 5-phenyl-N-phenylbiphenyl-3-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced by Compound 124-A (N-phenylnaphthalen-2-amine), and Compound 106-C was replaced by Compound (124-C 5-phenyl-N-phenylbiphenyl-3-amine) Thus, it could be synthesized using the same method as in the synthesis of compound 106.

Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M+]:1198
Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M < + >]: 1198

[[ 합성예Synthetic example 104] 화합물 125의 제조 104] Preparation of Compound 125

합성예 85에서 화합물 106-A를 화합물 125-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 125-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 125-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 106-C was replaced with compound 125-C (N, 9, 9-triphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M+]:1352
Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M < + >]: 1352

[[ 합성예Synthetic example 105] 화합물 126의 제조 105] Preparation of Compound 126

합성예 85에서 화합물 106-A를 화합물 126-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 126-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 126-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 106-C was replaced with compound 126-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M+]:1532
Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M < + >]: 1532

[[ 합성예Synthetic example 106] 화합물 127의 제조 106] Preparation of Compound 127

합성예 85에서 화합물 106-A를 화합물 127-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 106-C를 화합물 127-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, compound 106-A was replaced with compound 127-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 106-C was replaced with compound 127-C (4- (naphthalen -1-yl) -N-phenylaniline) can be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 92.05; H, 5.69; N, 2.26 [M+]:1238
Elemental Analysis: C, 92.05; H, 5.69; N, 2.26 [M < + >]: 1238

[[ 합성예Synthetic example 107] 화합물 128의 제조 107] Preparation of Compound 128

합성예 85에서 화합물 106-A를 화합물 128-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 106-C를 화합물 128-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 128-A (N-phenylfluoranthen-3-amine), and Compound 106-C was replaced with Compound 128-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 92.34; H, 5.48; N, 2.18 [M+]:1286
Elemental Analysis: C, 92.34; H, 5.48; N, 2.18 [M < + >]: 1286

[[ 합성예Synthetic example 108] 화합물 129의 제조 108] Preparation of Compound 129

합성예 85에서 화합물 106-A를 화합물 129-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 106-C를 화합물 129-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하여, 화합물 106의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 85, Compound 106-A was replaced with Compound 129-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and Compound 106-C was replaced with Compound 129-C ( N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) could be synthesized using the same method as the synthesis of Compound 106.

Elemental Analysis: C, 92.21; H, 5.86; N, 1.94 [M+]:1444
Elemental Analysis: C, 92.21; H, 5. 86; N, 1.94 [M < + >]: 1444

[[ 합성예Synthetic example 109] 화합물 130의 제조 109] Preparation of Compound 130

[합성예 109-1] 화합물 130-1의 제조 Synthesis Example 109-1 Preparation of the compound 130-1.

합성예 1-1의 화합물 7-A를 화합물 130-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-A of Synthesis Example 1-1 was replaced with Compound 130-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 109-2] 화합물 130-2의 제조 Synthesis Example 109-2 Preparation of the compound 130-2.

합성예 1-2의 화합물 7-1을 화합물 130-1로, 화합물 7-B를 화합물 130-B (9-bromo-7,7-dimethyl-7H-benzo[c]fluorene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Replacing compound 7-1 of Synthesis Example 1-2 with compound 130-1, compound 7-B with compound 130-B (9-bromo-7,7-dimethyl-7H-benzo [c] fluorene), and Synthesis was carried out using the same method as in the synthesis of 7-2.

[합성예 109-3] 화합물 130-3의 제조 Synthesis Example 109-3 Preparation of the compound 130-3.

합성예 1-3의 화합물 7-2를 화합물 130-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with Compound 130-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 109-4] 화합물 130의 제조 Synthesis Example 109-4 Preparation of the Compound 130

합성예 1-4의 화합물 7-3을 화합물 130-3으로, 화합물 7-C를 화합물 130-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 130-3, Compound 7-C with Compound 130-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 91.07; H, 6.34; N, 2.59 [M+]:1080
Elemental Analysis: C, 91.07; H, 6.34; N, 2.59 [M +]: 1080

[[ 합성예Synthetic example 110] 화합물 131의 제조 110] Preparation of Compound 131

합성예 109에서 화합물 130-A를 화합물 131-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 130-C를 화합물 131-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 131-A (N-phenylnaphthalen-2-amine), and compound 130-C was replaced with compound 131-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M+]:1152
Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M < + >]: 1152

[[ 합성예Synthetic example 111] 화합물 132의 제조 111] Preparation of Compound 132

합성예 109에서 화합물 130-A를 화합물 132-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 130-C를 화합물 132-C (N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 132-A (N-phenylnaphthalen-1-amine), and compound 130-C was replaced with compound 132-C (N- (4- (trimethylsilyl) phenyl) naphthalen-1- amine), using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 89.34; H, 5.86; N, 2.40; Si, 2.40 [M+]:1168
Elemental Analysis: C, 89.34; H, 5. 86; N, 2.40; Si, 2.40 [M < + >]: 1168

[[ 합성예Synthetic example 112] 화합물 133의 제조 112] Preparation of Compound 133

합성예 109에서 화합물 130-A를 화합물 133-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 130-C를 화합물 133-C (diphenylamine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 130-A is replaced with compound 133-A (4-tert-butyl-N- (4-isopropylphenyl) aniline) in Synthesis Example 109, and compound 130-C is replaced with compound 133-C (diphenylamine) Synthesis was carried out using the same method as the synthesis of 130.

Elemental Analysis: C, 91.00; H, 6.44; N, 2.56 [M+]:1094
Elemental Analysis: C, 91.00; H, 6.44; N, 2.56 [M +]: 1094

[[ 합성예Synthetic example 113] 화합물 134의 제조 113] Preparation of Compound 134

합성예 109에서 화합물 130-A를 화합물 134-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 134-C (diphenylamine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 134-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 130-C was replaced with compound 134-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 114] 화합물 135의 제조 114] Preparation of Compound 135

합성예 109에서 화합물 130-A를 화합물 135-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 130-C를 화합물 135-C (diphenylamine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 130-A was replaced with Compound 135-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine) in Synthesis Example 109, and compound 130-C was replaced with Compound 135-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 115] 화합물 136의 제조 115] Preparation of Compound 136

합성예 109에서 화합물 130-A를 화합물 136-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 130-C를 화합물 136-C (diphenylamine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 136-A (N- (4-tert-butylphenyl) -3-methylaniline), and Compound 130-C was replaced with Compound 136-C (diphenylamine), Compound 130 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M+]:1066
Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M +]: 1066

[[ 합성예Synthetic example 116] 화합물 137의 제조 116] Preparation of Compound 137

합성예 109에서 화합물 130-A를 화합물 137-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 130-C를 화합물 137-C (diphenylamine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced by Compound 137-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and Compound 130-C was replaced by Compound 137-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M+]:1124
Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M < + >]: 1124

[[ 합성예Synthetic example 117] 화합물 138의 제조 117] Preparation of Compound 138

합성예 109에서 화합물 130-A를 화합물 138-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 130-C를 화합물 138-C (N-(4-isopropylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 138-A (N-phenylbiphenyl-4-amine), and Compound 130-C was replaced with Compound 138-C (N- (4-isopropylphenyl) -9,9-dimethyl- 9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.67; H, 6.06; N, 2.27 [M+]:1230
Elemental Analysis: C, 91.67; H, 6.06; N, 2.27 [M < + >]: 1230

[[ 합성예Synthetic example 118] 화합물 139의 제조 118] Preparation of Compound 139

합성예 109에서 화합물 130-A를 화합물 139-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 139-C (diphenylamine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 139-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and Compound 130-C was replaced with Compound 139- Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 130.

Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M+]:1188
Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M < + >]: 1188

[[ 합성예Synthetic example 119] 화합물 140의 제조 119] Preparation of Compound 140

합성예 109에서 화합물 130-A를 화합물 140-A (4-tert-butyl-N-phenylaniline)로 대체하고, 화합물 130-C를 화합물 140-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 140-A (4-tert-butyl-N-phenylaniline), and Compound 130-C was replaced with Compound 140-C (11,11-dimethyl-N-phenyl-11H- Substituted with benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.59; H, 6.12; N, 2.30 [M+]:1218
Elemental Analysis: C, 91.59; H, 6. 12; N, 2.30 [M < + >]: 1218

[[ 합성예Synthetic example 120] 화합물 141의 제조 120] Preparation of Compound 141

합성예 109에서 화합물 130-A를 화합물 141-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 130-C를 화합물 141-C (N-phenylbenzo[d]thiazol-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 130-A with compound 141-A (N-phenylnaphthalen-2-amine) in Synthesis Example 109 and replaced compound 130-C with compound 141-C (N-phenylbenzo [d] thiazol-2-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M+]:1103
Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M +]: 1103

[[ 합성예Synthetic example 121] 화합물 142의 제조 121] Preparation of Compound 142

합성예 109에서 화합물 130-A를 화합물 142-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 142-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 142-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 130-C was replaced with compound 142-C (11,11- Substituted with dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 122] 화합물 143의 제조 122] Preparation of Compound 143

합성예 109에서 화합물 130-A를 화합물 143-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 143-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 143-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and compound 130-C was replaced with compound 143-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.49; H, 6.36; N, 2.16 [M+]:1298
Elemental Analysis: C, 91.49; H, 6. 36; N, 2.16 [M < + >]: 1298

[[ 합성예Synthetic example 123] 화합물 144의 제조 123] Preparation of Compound 144

합성예 109에서 화합물 130-A를 화합물 144-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 144-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 144-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 130-C was replaced with compound 144-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine) could be substituted using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 124] 화합물 145의 제조 124] Preparation of Compound 145

합성예 109에서 화합물 130-A를 화합물 145-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 130-C를 화합물 145-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 145-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and Compound 130-C was replaced with Compound 145-C ( Substituted with 11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M+]:1378
Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M < + >]: 1378

[[ 합성예Synthetic example 125] 화합물 146의 제조 125] Preparation of Compound 146

합성예 109에서 화합물 130-A를 화합물 146-A (7,7-dimethyl-N-(naphthalen-2-yl)-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 130-C를 화합물 146-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 146-A (7,7-dimethyl-N- (naphthalen-2-yl) -7H-benzo [c] fluoren-9-amine) and Compound 130-C Was replaced with compound 146-C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), and it could be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 91.72; H, 6.19; N, 2.10 [M+]:1334
Elemental Analysis: C, 91.72; H, 6.19; N, 2.10 [M < + >]: 1334

[[ 합성예Synthetic example 126] 화합물 147의 제조 126] Preparation of Compound 147

합성예 109에서 화합물 130-A를 화합물 147-A N-(4-tert-butylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine 로 대체하고, 화합물 130-C를 화합물 147-C 7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine 로 대체하여, 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 147-A N- (4-tert-butylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine, and compound 130-C was 147-C 7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine was substituted and synthesized using the same method.

Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M+]:1398
Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M < + >]: 1398

[[ 합성예Synthetic example 127] 화합물 148의 제조 127] Preparation of Compound 148

합성예 109에서 화합물 130-A를 화합물 148-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 130-C를 화합물 148-C (5-phenyl-N-phenylbiphenyl-3-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 148-A (N-phenylnaphthalen-2-amine), and Compound 130-C was replaced with Compound 148-C (5-phenyl-N-phenylbiphenyl-3-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M+]:1198
Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M < + >]: 1198

[[ 합성예Synthetic example 128] 화합물 149의 제조 128] Preparation of Compound 149

합성예 109에서 화합물 130-A를 화합물 149-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 149-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 149-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 130-C was replaced with Compound 149-C (N, 9, 9-triphenyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M+]:1352
Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M < + >]: 1352

[[ 합성예Synthetic example 129] 화합물 150의 제조 129] Preparation of Compound 150

합성예 109에서 화합물 130-A를 화합물 150-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 150-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 150-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 130-C was replaced with compound 150-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M+]:1532
Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M < + >]: 1532

[[ 합성예Synthetic example 130] 화합물 151의 제조 130] Preparation of Compound 151

합성예 109에서 화합물 130-A를 화합물 151-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 130-C를 화합물 151-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 151-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 130-C was replaced with Compound 151-C (4- (naphthalen -1-yl) -N-phenylaniline) was synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 92.05; H, 5.69; N, 2.26 [M+]:1238
Elemental Analysis: C, 92.05; H, 5.69; N, 2.26 [M < + >]: 1238

[[ 합성예Synthetic example 131] 화합물 152의 제조 131] Preparation of Compound 152

합성예 109에서 화합물 130-A를 화합물 152-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 130-C를 화합물 152-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, compound 130-A was replaced with compound 152-A (N-phenylfluoranthen-3-amine), and compound 130-C was replaced with compound 152-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 92.34; H, 5.48; N, 2.18 [M+]:1286
Elemental Analysis: C, 92.34; H, 5.48; N, 2.18 [M < + >]: 1286

[[ 합성예Synthetic example 132] 화합물 153의 제조 132] Preparation of Compound 153

합성예 109에서 화합물 130-A를 화합물 153-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 130-C를 화합물 153-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하여, 화합물 130의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 109, Compound 130-A was replaced with Compound 153-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and Compound 130-C was replaced with Compound 153-C ( N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) could be synthesized using the same method as the synthesis of Compound 130.

Elemental Analysis: C, 92.21; H, 5.86; N, 1.94 [M+]:1444
Elemental Analysis: C, 92.21; H, 5. 86; N, 1.94 [M < + >]: 1444

[[ 합성예Synthetic example 133] 화합물 154의 제조 133] Preparation of Compound 154

[합성예 133-1] 화합물 154-1의 제조 Synthesis Example 133-1 Preparation of the compound 154-1.

합성예 1-1의 화합물 7-A를 화합물 154-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 154-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 133-2] 화합물 154-2의 제조 Synthesis Example 133-2 Preparation of the compound 154-2.

합성예 1-2의 화합물 7-1을 화합물 154-1로, 화합물 7-B를 화합물 154-B (2-bromo-11,11-dimethyl-11H-benzo[b]fluorene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Replacing compound 7-1 of Synthesis Example 1-2 with compound 154-1, compound 7-B with compound 154-B (2-bromo-11,11-dimethyl-11H-benzo [b] fluorene), and Synthesis was carried out using the same method as in the synthesis of 7-2.

[합성예 133-3] 화합물 154-3의 제조 Synthesis Example 133-3 Preparation of the Compound 154-3.

합성예 1-3의 화합물 7-2를 화합물 154-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with compound 154-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 133-4] 화합물 154의 제조 Synthesis Example 133-4 Preparation of the Compound 154

합성예 1-4의 화합물 7-3을 화합물 154-3으로, 화합물 7-C를 화합물 154-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 154-3, Compound 7-C with Compound 154-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 90.87; H, 6.64; N, 2.49 [M+]:1122
Elemental Analysis: C, 90.87; H, 6.64; N, 2.49 [M < + >]: 1122

[[ 합성예Synthetic example 134] 화합물 155의 제조 134] Preparation of Compound 155

합성예 133에서 화합물 154-A를 화합물 155-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 154-C를 화합물 155-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 155-A (N-phenylnaphthalen-2-amine), and compound 154-C was replaced with compound 155-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M+]:1152
Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M < + >]: 1152

[[ 합성예Synthetic example 135] 화합물 156의 제조 135] Preparation of Compound 156

합성예 133에서 화합물 154-A를 화합물 156-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 154-C를 화합물 156-C (N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 156-A (N-phenylnaphthalen-1-amine), and compound 154-C was replaced with compound 156-C (N- (4- (trimethylsilyl) phenyl) naphthalen-1- amine), using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 89.34; H, 5.86; N, 2.40; Si, 2.40 [M+]:1168
Elemental Analysis: C, 89.34; H, 5. 86; N, 2.40; Si, 2.40 [M < + >]: 1168

[[ 합성예Synthetic example 136] 화합물 157의 제조 136] Preparation of Compound 157

합성예 133에서 화합물 154-A를 화합물 157-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 154-C를 화합물 157-C (diphenylamine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 157-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and Compound 154-C was replaced with Compound 157-C (diphenylamine) Synthesis was carried out using the same method as the synthesis of 154.

Elemental Analysis: C, 91.00; H, 6.44; N, 2.56 [M+]:1094Elemental Analysis: C, 91.00; H, 6. 44; N, 2.56 [M +]: 1094

[[ 합성예Synthetic example 137] 화합물 158의 제조 137] Preparation of Compound 158

합성예 133에서 화합물 154-A를 화합물 158-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 158-C (diphenylamine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 158-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 154-C was replaced with compound 158-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 138] 화합물 159의 제조 138] Preparation of Compound 159

합성예 133에서 화합물 154-A를 화합물 159-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 154-C를 화합물 159-C (diphenylamine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 159-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), and compound 154-C was replaced with compound 159-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 139] 화합물 160의 제조 139] Preparation of Compound 160

합성예 133에서 화합물 154-A를 화합물 160-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 154-C를 화합물 160-C (diphenylamine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 160-A (N- (4-tert-butylphenyl) -3-methylaniline), and Compound 154-C was replaced with Compound 160-C (diphenylamine), Compound 154 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M+]:1066
Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M +]: 1066

[[ 합성예Synthetic example 140] 화합물 161의 제조 140] Preparation of Compound 161

합성예 133에서 화합물 154-A를 화합물 161-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 154-C를 화합물 161-C (diphenylamine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 161-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and Compound 154-C was replaced with Compound 161-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M+]:1124
Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M < + >]: 1124

[[ 합성예Synthetic example 141] 화합물 162의 제조 141] Preparation of Compound 162

합성예 133에서 화합물 154-A를 화합물 162-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 154-C를 화합물 162-C (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 162-A (N-phenylbiphenyl-4-amine), and compound 154-C was replaced with compound 162-C (9,9-dimethyl-N-phenyl-9H-fluoren- 2-amine), using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M+]:1188
Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M < + >]: 1188

[[ 합성예Synthetic example 142] 화합물 163의 제조 142] Preparation of Compound 163

합성예 133에서 화합물 154-A를 화합물 163-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 163-C (diphenylamine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 163-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and Compound 154-C was replaced with Compound 163-. Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 154.

Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M+]:1188
Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M < + >]: 1188

[[ 합성예Synthetic example 143] 화합물 164의 제조 143] Preparation of Compound 164

합성예 133에서 화합물 154-A를 화합물 164-A (4-tert-butyl-N-phenylaniline)로 대체하고, 화합물 154-C를 화합물 164-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 164-A (4-tert-butyl-N-phenylaniline), and Compound 154-C was replaced with Compound 164-C (11,11-dimethyl-N-phenyl-11H- Substituted with benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.59; H, 6.12; N, 2.30 [M+]:1218
Elemental Analysis: C, 91.59; H, 6. 12; N, 2.30 [M < + >]: 1218

[[ 합성예Synthetic example 144] 화합물 165의 제조 144] Preparation of Compound 165

합성예 133에서 화합물 154-A를 화합물 165-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 154-C를 화합물 165-C (N-phenylbenzo[d]thiazol-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 154-A is replaced with Compound 165-A (N-phenylnaphthalen-2-amine) in Synthesis Example 133, and compound 154-C is replaced with compound 165-C (N-phenylbenzo [d] thiazol-2-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M+]:1103
Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M +]: 1103

[[ 합성예Synthetic example 145] 화합물 166의 제조 145] Preparation of Compound 166

합성예 133에서 화합물 154-A를 화합물 166-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 166-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 166-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 154-C was replaced with compound 166-C (11,11- dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 146] 화합물 167의 제조 146] Preparation of Compound 167

합성예 133에서 화합물 154-A를 화합물 167-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 167-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 167-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and Compound 154-C was replaced with Compound 167-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.49; H, 6.36; N, 2.16 [M+]:1298
Elemental Analysis: C, 91.49; H, 6. 36; N, 2.16 [M < + >]: 1298

[[ 합성예Synthetic example 147] 화합물 168의 제조 147] Preparation of Compound 168

합성예 133에서 화합물 154-A를 화합물 168-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 168-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 168-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and Compound 154-C was replaced with Compound 168-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 148] 화합물 169의 제조 148] Preparation of Compound 169

합성예 133에서 화합물 154-A를 화합물 169-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 154-C를 화합물 169-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 169-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and Compound 154-C was replaced with Compound 169-C ( Substituted with 11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M+]:1378
Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M < + >]: 1378

[[ 합성예Synthetic example 149] 화합물 170의 제조 149] Preparation of Compound 170

합성예 133에서 화합물 154-A를 화합물 170-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 170-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 170-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and Compound 154-C was replaced with Compound 170- Substituted with C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.72; H, 6.19; N, 2.10 [M+]:1334
Elemental Analysis: C, 91.72; H, 6.19; N, 2.10 [M < + >]: 1334

[[ 합성예Synthetic example 150] 화합물 171의 제조 150] Preparation of Compound 171

합성예 133에서 화합물 154-A를 화합물 171-A (7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 154-C를 화합물 171-C (N-(4-tert-butylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 171-A (7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine), and Compound 154-C was replaced with Compound 171-C ( Substituted by N- (4-tert-butylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M+]:1398
Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M < + >]: 1398

[[ 합성예Synthetic example 151] 화합물 172의 제조 151] Preparation of Compound 172

합성예 133에서 화합물 154-A를 화합물 172-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 154-C를 화합물 172-C (5-phenyl-N-phenylbiphenyl-3-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 154-A is replaced with Compound 172-A (N-phenylnaphthalen-2-amine) in Synthesis Example 133, and compound 154-C is replaced with compound 172-C (5-phenyl-N-phenylbiphenyl-3-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M+]:1198
Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M < + >]: 1198

[[ 합성예Synthetic example 152] 화합물 173의 제조 152] Preparation of Compound 173

합성예 133에서 화합물 154-A를 화합물 173-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 173-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 173-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 154-C was replaced with compound 173-C (N, 9, 9-triphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M+]:1353
Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M < + >]: 1353

[[ 합성예Synthetic example 153] 화합물 174의 제조 153] Preparation of Compound 174

합성예 133에서 화합물 154-A를 화합물 174-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 174-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 174-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 154-C was replaced with compound 174-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M+]:1532
Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M < + >]: 1532

[[ 합성예Synthetic example 154] 화합물 175의 제조 154] Preparation of Compound 175

합성예 133에서 화합물 154-A를 화합물 175-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 154-C를 화합물 175-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, compound 154-A was replaced with compound 175-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 154-C was replaced with compound 175-C (4- (naphthalen -1-yl) -N-phenylaniline) can be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M+]:1188
Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M < + >]: 1188

[[ 합성예Synthetic example 155] 화합물 176의 제조 155] Preparation of Compound 176

합성예 133에서 화합물 154-A를 화합물 176-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 154-C를 화합물 176-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 176-A (N-phenylfluoranthen-3-amine), and Compound 154-C was replaced with Compound 176-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 92.20; H, 5.54; N, 2.26 [M+]:1236
Elemental Analysis: C, 92.20; H, 5.54; N, 2.26 [M < + >]: 1236

[[ 합성예Synthetic example 156] 화합물 177의 제조 156] Preparation of Compound 177

합성예 133에서 화합물 154-A를 화합물 177-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 154-C를 화합물 177-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하여, 화합물 154의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 133, Compound 154-A was replaced with Compound 177-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and Compound 154-C was replaced with Compound 177-C ( N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) could be synthesized using the same method as the synthesis of Compound 154.

Elemental Analysis: C, 92.07; H, 5.92; N, 2.01 [M+]:1394
Elemental Analysis: C, 92.07; H, 5.92; N, 2.01 [M < + >]: 1394

[[ 합성예Synthetic example 157] 화합물 178의 제조 157] Preparation of Compound 178

[합성예 157-1] 화합물 178-1의 제조 Synthesis Example 157-1 Preparation of Compound 178-1

합성예 1-1의 화합물 7-A를 화합물 178-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 7-A of Synthesis Example 1-1 was replaced with compound 178-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 157-2] 화합물 178-2의 제조 Synthesis Example 157-2 Preparation of Compound 178-2

합성예 1-2의 화합물 7-1을 화합물 178-1로, 화합물 7-B를 화합물 178-B (2-bromo-9,9-diphenyl-9H-fluorene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 was replaced by Compound 178-1, and Compound 7-B was replaced by Compound 178-B (2-bromo-9,9-diphenyl-9H-fluorene). Synthesis was carried out using the same method as synthesis.

[합성예 157-3] 화합물 178-3의 제조 Synthesis Example 157-3 Preparation of Compound 178-3

합성예 1-3의 화합물 7-2를 화합물 178-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with compound 178-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 157-4] 화합물 178의 제조 Synthesis Example 157-4 Preparation of Compound 178

합성예 1-4의 화합물 7-3을 화합물 178-3으로, 화합물 7-C를 화합물 178-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 178-3, Compound 7-C with Compound 178-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 91.61; H, 6.18; N, 2.20 [M+]:1270
Elemental Analysis: C, 91.61; H, 6. 18; N, 2.20 [M +]: 1270

[[ 합성예Synthetic example 158] 화합물 179의 제조 158] Preparation of Compound 179

합성예 157에서 화합물 178-A를 화합물 179-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 178-C를 화합물 179-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 179-A (N-phenylnaphthalen-2-amine), and compound 178-C was replaced with compound 179-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.27; H, 5.58; N, 2.15 [M+]:1300
Elemental Analysis: C, 92.27; H, 5.58; N, 2.15 [M +]: 1300

[[ 합성예Synthetic example 159] 화합물 180의 제조 159] Preparation of Compound 180

합성예 157에서 화합물 178-A를 화합물 180-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 178-C를 화합물 180-C (N-(4-tert-butylphenyl)naphthalen-1-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 180-A (N-phenylnaphthalen-1-amine), and compound 178-C was replaced with compound 180-C (N- (4-tert-butylphenyl) naphthalen-1-amine ), It could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 90.24; H, 5.51; N, 2.13; Si, 2.13 [M+]:1316
Elemental Analysis: C, 90.24; H, 5.51; N, 2.13; Si, 2.13 [M < + >]: 1316

[[ 합성예Synthetic example 160] 화합물 181의 제조 160] Preparation of Compound 181

합성예 157에서 화합물 178-A를 화합물 181-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 178-C를 화합물 181-C (diphenylamine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 178-A is replaced with compound 181-A (4-tert-butyl-N- (4-isopropylphenyl) aniline) in Synthesis Example 157, and compound 178-C is replaced with compound 181-C (diphenylamine), Synthesis was carried out using the same method as the synthesis of 178.

Elemental Analysis: C, 91.75; H, 6.00; N, 2.25 [M+]:1242
Elemental Analysis: C, 91.75; H, 6.00; N, 2.25 [M < + >]: 1242

[[ 합성예Synthetic example 161] 화합물 182의 제조 161] Preparation of Compound 182

합성예 157에서 화합물 178-A를 화합물 182-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 182-C (diphenylamine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 182-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 182-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.35; H, 5.43; N, 2.22 [M+]:1260
Elemental Analysis: C, 92.35; H, 5. 43; N, 2.22 [M < + >]: 1260

[[ 합성예Synthetic example 162] 화합물 183의 제조 162] Preparation of Compound 183

합성예 157에서 화합물 178-A를 화합물 183-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 178-C를 화합물 183-C (diphenylamine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 183-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), and compound 178-C was replaced with compound 183-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 91.87; H, 5.67; N, 2.46 [M+]:1136
Elemental Analysis: C, 91.87; H, 5.67; N, 2.46 [M < + >]: 1136

[[ 합성예Synthetic example 163] 화합물 184의 제조 163] Preparation of Compound 184

합성예 157에서 화합물 178-A를 화합물 184-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 178-C를 화합물 184-C (diphenylamine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A is replaced with compound 184-A (N- (4-tert-butylphenyl) -3-methylaniline), and compound 178-C is replaced with compound 184-C (diphenylamine), compound 178 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 91.89; H, 5.80; N, 2.30 [M+]:1214
Elemental Analysis: C, 91.89; H, 5.80; N, 2.30 [M +]: 1214

[[ 합성예Synthetic example 164] 화합물 185의 제조 164] Preparation of Compound 185

합성예 157에서 화합물 178-A를 화합물 185-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 178-C를 화합물 185-C (diphenylamine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A is replaced with compound 185-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and compound 178-C is replaced with compound 185-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 89.58; H, 6.01; N, 2.20; Si, 2.20 [M+]:1272
Elemental Analysis: C, 89.58; H, 6.01; N, 2.20; Si, 2.20 [M < + >]: 1272

[[ 합성예Synthetic example 165] 화합물 186의 제조 165] Preparation of Compound 186

합성예 157에서 화합물 178-A를 화합물 186-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 178-C를 화합물 186-C (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 186-A (N-phenylbiphenyl-4-amine), and compound 178-C was replaced with compound 186-C (9,9-dimethyl-N-phenyl-9H-fluoren- 2-amine) could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.48; H, 5.43; N, 2.09 [M+]:1336
Elemental Analysis: C, 92.48; H, 5. 43; N, 2.09 [M +]: 1336

[[ 합성예Synthetic example 166] 화합물 187의 제조 166] Preparation of Compound 187

합성예 157에서 화합물 178-A를 화합물 187-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 187-C (diphenylamine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 187-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 187-A. Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 178.

Elemental Analysis: C, 92.48; H, 5.43; N, 2.09 [M+]:1336
Elemental Analysis: C, 92.48; H, 5. 43; N, 2.09 [M +]: 1336

[[ 합성예Synthetic example 167] 화합물 188의 제조 167] Preparation of Compound 188

합성예 157에서 화합물 178-A를 화합물 188-A (4-tert-butyl-N-phenylaniline)로 대체하고, 화합물 178-C를 화합물 188-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 188-A (4-tert-butyl-N-phenylaniline), and compound 178-C was replaced with compound 188-C (11,11-dimethyl-N-phenyl-11H- Substituted with benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.20; H, 5.75; N, 2.05 [M+]:1366
Elemental Analysis: C, 92.20; H, 5.75; N, 2.05 [M < + >]: 1366

[[ 합성예Synthetic example 168] 화합물 189의 제조 168] Preparation of Compound 189

합성예 157에서 화합물 178-A를 화합물 189-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 178-C를 화합물 189-C (N-phenylbenzo[d]thiazol-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 178-A with compound 189-A (N-phenylnaphthalen-2-amine) in Synthesis Example 157 and replaced compound 178-C with compound 189-C (N-phenylbenzo [d] thiazol-2-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 89.18; H, 4.91; N, 3.35; S, 2.56 [M+]:1251
Elemental Analysis: C, 89.18; H, 4.91; N, 3.35; S, 2.56 [M +]: 1251

[[ 합성예Synthetic example 169] 화합물 190의 제조 169] Preparation of Compound 190

합성예 157에서 화합물 178-A를 화합물 190-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 190-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 190-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 190-C (11,11- dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M+]:1178
Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M < + >]: 1178

[[ 합성예Synthetic example 170] 화합물 191의 제조 170] Preparation of Compound 191

합성예 157에서 화합물 178-A를 화합물 191-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 191-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 191-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 191-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 91.11; H, 6.55; N, 2.34 [M+]:1198
Elemental Analysis: C, 91.11; H, 6.55; N, 2.34 [M < + >]: 1198

[[ 합성예Synthetic example 171] 화합물 192의 제조 171] Preparation of Compound 192

합성예 157에서 화합물 178-A를 화합물 192-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 192-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 192-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 192-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M+]:1178
Elemental Analysis: C, 91.64; H, 5.98; N, 2.37 [M < + >]: 1178

[[ 합성예Synthetic example 172] 화합물 193의 제조 172] Preparation of Compound 193

합성예 157에서 화합물 178-A를 화합물 193-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 178-C를 화합물 193-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 193-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and compound 178-C was replaced with compound 193-C ( Substituted with 11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.76; H, 5.41; N, 1.83 [M+]:1526
Elemental Analysis: C, 92.76; H, 5.41; N, 1.83 [M < + >]: 1526

[[ 합성예Synthetic example 173] 화합물 194의 제조 173] Preparation of Compound 194

합성예 157에서 화합물 178-A를 화합물 194-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 194-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 194-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and compound 178-C was replaced with compound 194-. Substituted by C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.27; H, 5.84; N, 1.89 [M+]:1482
Elemental Analysis: C, 92.27; H, 5.84; N, 1.89 [M < + >]: 1482

[[ 합성예Synthetic example 174] 화합물 195의 제조 174] Preparation of Compound 195

합성예 157에서 화합물 178-A를 화합물 195-A (7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 178-C를 화합물 195-C (N-(4-tert-butylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 195-A (7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine), and compound 178-C was replaced with compound 195-C ( Substituted with N- (4-tert-butylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.33; H, 5.86; N, 1.81 [M+]:1546
Elemental Analysis: C, 92.33; H, 5. 86; N, 1.81 [M < + >]: 1546

[[ 합성예Synthetic example 175] 화합물 196의 제조 175] Preparation of Compound 196

합성예 157에서 화합물 178-A를 화합물 196-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 178-C를 화합물 196-C (5-phenyl-N-phenylbiphenyl-3-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 178-A is replaced with Compound 196-A (N-phenylnaphthalen-2-amine) in Synthesis Example 157, and compound 178-C is replaced with compound 196-C (5-phenyl-N-phenylbiphenyl-3-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.69; H, 5.24; N, 2.08 [M+]:1346
Elemental Analysis: C, 92.69; H, 5. 24; N, 2.08 [M +]: 1346

[[ 합성예Synthetic example 176] 화합물 197의 제조 176] Preparation of Compound 197

합성예 157에서 화합물 178-A를 화합물 197-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 197-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 197-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 197-C (N, 9, 9-triphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.77; H, 5.37; N, 1.87 [M+]:1500
Elemental Analysis: C, 92.77; H, 5. 37; N, 1.87 [M < + >]: 1500

[[ 합성예Synthetic example 177] 화합물 198의 제조 177] Preparation of Compound 198

합성예 157에서 화합물 178-A를 화합물 198-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 198-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 198-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 198-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.82; H, 5.51; N, 1.67 [M+]:1680
Elemental Analysis: C, 92.82; H, 5.51; N, 1.67 [M < + >]: 1680

[[ 합성예Synthetic example 178] 화합물 199의 제조 178] Preparation of Compound 199

합성예 157에서 화합물 178-A를 화합물 199-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 178-C를 화합물 199-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 199-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 178-C was replaced with compound 199-C (4- (naphthalen) -1-yl) -N-phenylaniline) can be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.61; H, 5.37; N, 2.02 [M+]:1386
Elemental Analysis: C, 92.61; H, 5. 37; N, 2.02 [M +]: 1386

[[ 합성예Synthetic example 179] 화합물 200의 제조 179] Preparation of Compound 200

합성예 157에서 화합물 178-A를 화합물 200-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 178-C를 화합물 200-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 200-A (N-phenylfluoranthen-3-amine), and compound 178-C was replaced with compound 200-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.85; H, 5.19; N, 1.95 [M+]:1434
Elemental Analysis: C, 92.85; H, 5.19; N, 1.95 [M < + >]: 1434

[[ 합성예Synthetic example 180] 화합물 201의 제조 180] Preparation of Compound 201

합성예 157에서 화합물 178-A를 화합물 201-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 178-C를 화합물 201-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하여, 화합물 178의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 157, compound 178-A was replaced with compound 201-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and compound 178-C was replaced with compound 201-C ( N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) could be synthesized using the same method as the synthesis of Compound 178.

Elemental Analysis: C, 92.68; H, 5.56; N, 1.76 [M+]: 1592
Elemental Analysis: C, 92.68; H, 5.56; N, 1.76 [M < + >]: 1592

[[ 합성예Synthetic example 181] 화합물 202의 제조 181] Preparation of Compound 202

[합성예 181-1] 화합물 202-1의 제조 Synthesis Example 181-1 Preparation of Compound 202-1

합성예 1-1의 화합물 7-A를 화합물 202-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with Compound 202-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 181-2] 화합물 202-2의 제조 Synthesis Example 181-2 Preparation of the compound 202-2.

합성예 1-2의 화합물 7-1을 화합물 202-1로, 화합물 7-B를 화합물 202-B (9-bromo-7,7-dimethyl-7H-benzo[de]anthracene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Replacing compound 7-1 of Synthesis Example 1-2 with compound 202-1, compound 7-B with compound 202-B (9-bromo-7,7-dimethyl-7H-benzo [de] anthracene), and Synthesis was carried out using the same method as in the synthesis of 7-2.

[합성예 181-3] 화합물 202-3의 제조 Synthesis Example 181-3 Preparation of the compound 202-3.

합성예 1-3의 화합물 7-2를 화합물 202-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with compound 202-2, and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 181-4] 화합물 202의 제조 Synthesis Example 181-4 Preparation of the Compound 202

합성예 1-4의 화합물 7-3을 화합물 202-3으로, 화합물 7-C를 화합물 202-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 202-3, Compound 7-C with Compound 202-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 90.87; H, 6.64; N, 2.49 [M+]:1122
Elemental Analysis: C, 90.87; H, 6.64; N, 2.49 [M < + >]: 1122

[[ 합성예Synthetic example 182] 화합물 203의 제조 182] Preparation of Compound 203

합성예 181에서 화합물 202-A를 화합물 203-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 202-C를 화합물 203-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 203-A (N-phenylnaphthalen-2-amine), and compound 202-C was replaced with compound 203-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M+]:1152
Elemental Analysis: C, 91.63; H, 5.94; N, 2.43 [M < + >]: 1152

[[ 합성예Synthetic example 183] 화합물 204의 제조 183] Preparation of Compound 204

합성예 181에서 화합물 202-A를 화합물 204-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 202-C를 화합물 204-C (N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 204-A (N-phenylnaphthalen-1-amine), and compound 202-C was replaced with compound 204-C (N- (4- (trimethylsilyl) phenyl) naphthalen-1- amine), using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 89.34; H, 5.86; N, 2.40; Si, 2.40 [M+]: 1168
Elemental Analysis: C, 89.34; H, 5. 86; N, 2.40; Si, 2.40 [M < + >]: 1168

[[ 합성예Synthetic example 184] 화합물 205의 제조 184] Preparation of Compound 205

합성예 181에서 화합물 202-A를 화합물 205-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 202-C를 화합물 205-C (diphenylamine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, the compound 202-A was replaced with the compound 205-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and the compound 202-C was replaced with the compound 205-C (diphenylamine). Synthesis was carried out using the same method as the synthesis of 202.

Elemental Analysis: C, 91.00; H, 6.44; N, 2.56 [M+]: 1094
Elemental Analysis: C, 91.00; H, 6.44; N, 2.56 [M < + >]: 1094

[[ 합성예Synthetic example 185] 화합물 206의 제조 185] Preparation of Compound 206

합성예 181에서 화합물 202-A를 화합물 206-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 206-C (diphenylamine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 206-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 202-C was replaced with compound 206-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 186] 화합물 207의 제조 186] Preparation of Compound 207

합성예 181에서 화합물 202-A를 화합물 207-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 202-C를 화합물 207-C (diphenylamine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 207-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine), and compound 202-C was replaced with compound 207-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M+]:1112
Elemental Analysis: C, 91.69; H, 5.79; N, 2.52 [M < + >]: 1112

[[ 합성예Synthetic example 187] 화합물 208의 제조 187] Preparation of Compound 208

합성예 181에서 화합물 202-A를 화합물 208-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 202-C를 화합물 208-C (diphenylamine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 208-A (N- (4-tert-butylphenyl) -3-methylaniline), and compound 202-C was replaced with compound 208-C (diphenylamine), compound 202 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M+]:1166
Elemental Analysis: C, 91.14; H, 6.23; N, 2.62 [M < + >]: 1166

[[ 합성예Synthetic example 188] 화합물 209의 제조 188] Preparation of Compound 209

합성예 181에서 화합물 202-A를 화합물 209-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 202-C를 화합물 209-C (diphenylamine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, Compound 202-A was replaced with Compound 209-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline), and Compound 202-C was replaced with Compound 209-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M+]: 1124
Elemental Analysis: C, 88.57; H, 6.45; N, 2.49; Si, 2.50 [M < + >]: 1124

[[ 합성예Synthetic example 189] 화합물 210의 제조 189] Preparation of Compound 210

합성예 181에서 화합물 202-A를 화합물 210-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 202-C를 화합물 210-C (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 210-A (N-phenylbiphenyl-4-amine), and compound 202-C was replaced with compound 210-C (9,9-dimethyl-N-phenyl-9H-fluoren- 2-amine) could be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M+]: 1188
Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M < + >]: 1188

[[ 합성예Synthetic example 190] 화합물 211의 제조 190] Preparation of Compound 211

합성예 181에서 화합물 202-A를 화합물 211-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 211-C (diphenylamine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, Compound 202-A was replaced with Compound 211-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and Compound 202-C was replaced with Compound 211-. Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 202.

Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M+]: 1188
Elemental Analysis: C, 91.88; H, 5.76; N, 2.36 [M < + >]: 1188

[[ 합성예Synthetic example 191] 화합물 212의 제조 191] Preparation of Compound 212

합성예 181에서 화합물 202-A를 화합물 212-A (4-tert-butyl-N-phenylaniline)로 대체하고, 화합물 202-C를 화합물 212-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 212-A (4-tert-butyl-N-phenylaniline), and compound 202-C was replaced with compound 212-C (11,11-dimethyl-N-phenyl-11H- Substituted with benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.59; H, 6.12; N, 2.30 [M+]: 1218
Elemental Analysis: C, 91.59; H, 6. 12; N, 2.30 [M +]: 1218

[[ 합성예Synthetic example 192] 화합물 213의 제조 192] Preparation of Compound 213

합성예 181에서 화합물 202-A를 화합물 213-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 202-C를 화합물 213-C (N-phenylbenzo[d]thiazol-2-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 202-A is replaced with Compound 213-A (N-phenylnaphthalen-2-amine) in Synthesis Example 181, and compound 202-C is replaced with compound 213-C (N-phenylbenzo [d] thiazol-2-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M+]: 1103
Elemental Analysis: C, 88.09; H, 5.20; N, 3.80; S, 2.90 [M +]: 1103

[[ 합성예Synthetic example 193] 화합물 214의 제조 193] Preparation of Compound 214

합성예 181에서 화합물 202-A를 화합물 214-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 214-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 214-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 202-C was replaced with compound 214-C (11,11- Substituted with dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 194] 화합물 215의 제조 194] Preparation of Compound 215

합성예 181에서 화합물 202-A를 화합물 215-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 215-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 215-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and compound 202-C was replaced with compound 215-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.49; H, 6.36; N, 2.16 [M+]:1298
Elemental Analysis: C, 91.49; H, 6. 36; N, 2.16 [M < + >]: 1298

[[ 합성예Synthetic example 195] 화합물 216의 제조 195] Preparation of Compound 216

합성예 181에서 화합물 202-A를 화합물 216-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 216-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 216-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 202-C was replaced with compound 216-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M+]:1278
Elemental Analysis: C, 91.98; H, 5.83; N, 2.19 [M < + >]: 1278

[[ 합성예Synthetic example 196] 화합물 217의 제조 196] Preparation of Compound 217

합성예 181에서 화합물 202-A를 화합물 217-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 202-C를 화합물 217-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 217-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and compound 202-C was replaced with compound 217-C ( 11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine) could be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M+]:1378
Elemental Analysis: C, 92.27; H, 5.70; N, 2.03 [M < + >]: 1378

[[ 합성예Synthetic example 197] 화합물 218의 제조 197] Preparation of Compound 218

합성예 181에서 화합물 202-A를 화합물 218-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 218-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, Compound 202-A was replaced with Compound 218-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and Compound 202-C was replaced with Compound 218- Substituted with C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.72; H, 6.19; N, 2.10 [M+]:1334
Elemental Analysis: C, 91.72; H, 6.19; N, 2.10 [M < + >]: 1334

[[ 합성예Synthetic example 198] 화합물 219의 제조 198] Preparation of Compound 219

합성예 181에서 화합물 202-A를 화합물 219-A (7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 202-C를 화합물 219-C (N-(4-tert-butylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, Compound 202-A was replaced with Compound 219-A (7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine), and Compound 202-C was replaced with Compound 219-C ( Substituted by N- (4-tert-butylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M+]:1398
Elemental Analysis: C, 91.81; H, 6.19; N, 2.00 [M < + >]: 1398

[[ 합성예Synthetic example 199] 화합물 220의 제조 199] Preparation of Compound 220

합성예 181에서 화합물 202-A를 화합물 220-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 202-C를 화합물 220-C (5-phenyl-N-phenylbiphenyl-3-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 202-A is replaced with Compound 220-A (N-phenylnaphthalen-2-amine) in Synthesis Example 181, and compound 202-C is replaced with compound 220-C (5-phenyl-N-phenylbiphenyl-3-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M+]:1198
Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M < + >]: 1198

[[ 합성예Synthetic example 200] 화합물 221의 제조 200] Preparation of Compound 221

합성예 181에서 화합물 202-A를 화합물 221-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 221-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 221-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 202-C was replaced with compound 221-C (N, 9, 9-triphenyl-9H-fluoren-2-amine) could be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M+]:1352
Elemental Analysis: C, 92.27; H, 5.66; N, 2.07 [M < + >]: 1352

[[ 합성예Synthetic example 201] 화합물 222의 제조 201] Preparation of Compound 222

합성예 181에서 화합물 202-A를 화합물 222-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 222-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 222-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 202-C was replaced with compound 222-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) was synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M+]:1532
Elemental Analysis: C, 92.39; H, 5.78; N, 1.83 [M < + >]: 1532

[[ 합성예Synthetic example 202] 화합물 223의 제조 202] Preparation of Compound 223

합성예 181에서 화합물 202-A를 화합물 223-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 202-C를 화합물 223-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 223-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 202-C was replaced with compound 223-C (4- (naphthalen -1-yl) -N-phenylaniline) can be synthesized using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 92.05; H, 5.69; N, 2.26 [M+]: 1238
Elemental Analysis: C, 92.05; H, 5.69; N, 2.26 [M < + >]: 1238

[[ 합성예Synthetic example 203] 화합물 224의 제조 203] Preparation of Compound 224

합성예 181에서 화합물 202-A를 화합물 224-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 202-C를 화합물 224-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 202의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 224-A (N-phenylfluoranthen-3-amine), and compound 202-C was replaced with compound 224-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 202.

Elemental Analysis: C, 92.34; H, 5.48; N, 2.18 [M+]: 1286
Elemental Analysis: C, 92.34; H, 5.48; N, 2.18 [M < + >]: 1286

[[ 합성예Synthetic example 204] 화합물 225의 제조 204] Preparation of Compound 225

합성예 181에서 화합물 202-A를 화합물 225-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 202-C를 화합물 225-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하여, 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 181, compound 202-A was replaced with compound 225-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and compound 202-C was replaced with compound 225-C ( N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) could be synthesized using the same method.

Elemental Analysis: C, 92.21; H, 5.86; N, 1.94 [M+]:1444
Elemental Analysis: C, 92.21; H, 5. 86; N, 1.94 [M < + >]: 1444

[[ 합성예Synthetic example 205] 화합물 226의 제조 205] Preparation of Compound 226

[합성예 205-1] 화합물 226-1의 제조 Synthesis Example 205-1 Preparation of Compound 226-1

합성예 1-1의 화합물 7-A를 화합물 226-A (4-tert-butyl-N-p-tolylaniline)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with compound 226-A (4-tert-butyl-N-p-tolylaniline), and was synthesized using the same method as the synthesis of Compound 7-1.

[합성예 205-2] 화합물 226-2의 제조 Synthesis Example 205-2 Preparation of Compound 226-2.

합성예 1-2의 화합물 7-1을 화합물 226-1로, 화합물 7-B를 화합물 226-B (9-bromo-7,7-dimethyl-7H-benzo[de]anthracene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Replacing compound 7-1 of Synthesis Example 1-2 with compound 226-1, compound 7-B with compound 226-B (9-bromo-7,7-dimethyl-7H-benzo [de] anthracene), and Synthesis was carried out using the same method as in the synthesis of 7-2.

[합성예 205-3] 화합물 226-3의 제조 Synthesis Example 205-3 Preparation of Compound 226-3.

합성예 1-3의 화합물 7-2를 화합물 226-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with compound 226-2 and could be synthesized using the same method as the synthesis of Compound 7-3.

[합성예 205-4] 화합물 226의 제조 Synthesis Example 205-4 Preparation of Compound 226

합성예 1-4의 화합물 7-3을 화합물 226-3으로, 화합물 7-C를 화합물 226-C (4-isopropyl-N-p-tolylaniline)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Synthesis of Compound 7 (Synthesis Example 1-4) by replacing Compound 7-3 of Synthesis Example 1-4 with Compound 226-3, Compound 7-C with Compound 226-C (4-isopropyl-Np-tolylaniline) It could be synthesized using the same method as.

Elemental Analysis: C, 91.29; H, 6.01; N, 2.70 [M+]:1038
Elemental Analysis: C, 91.29; H, 6.01; N, 2.70 [M +]: 1038

[[ 합성예Synthetic example 206] 화합물 227의 제조 206] Preparation of Compound 227

합성예 205에서 화합물 226-A를 화합물 227-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 226-C를 화합물 227-C (N-(4-tert-butylphenyl)naphthalen-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 227-A (N-phenylnaphthalen-2-amine), and compound 226-C was replaced with compound 227-C (N- (4-tert-butylphenyl) naphthalen-2-amine ), It could be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.10; H, 5.28; N, 2.62 [M+]:1068
Elemental Analysis: C, 92.10; H, 5. 28; N, 2.62 [M < + >]: 1068

[[ 합성예Synthetic example 207] 화합물 228의 제조 207] Preparation of Compound 228

합성예 205에서 화합물 226-A를 화합물 228-A (N-phenylnaphthalen-1-amine)로 대체하고, 화합물 226-C를 화합물 228-C (N-(4-(trimethylsilyl)phenyl)naphthalen-1-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 228-A (N-phenylnaphthalen-1-amine), and compound 226-C was replaced with compound 228-C (N- (4- (trimethylsilyl) phenyl) naphthalen-1- amine), using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 89.63; H, 5.20; N, 2.58; Si, 2.59 [M+]:1084
Elemental Analysis: C, 89.63; H, 5.20; N, 2.58; Si, 2.59 [M < + >]: 1084

[[ 합성예Synthetic example 208] 화합물 229의 제조 208] Preparation of Compound 229

합성예 205에서 화합물 226-A를 화합물 229-A (4-tert-butyl-N-(4-isopropylphenyl)aniline)로 대체하고, 화합물 226-C를 화합물 229-C (diphenylamine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A is replaced with compound 229-A (4-tert-butyl-N- (4-isopropylphenyl) aniline), and compound 226-C is replaced with compound 229-C (diphenylamine) Synthesis was carried out using the same method as that of 226.

Elemental Analysis: C, 91.45; H, 5.78; N, 2.77 [M+]:1010
Elemental Analysis: C, 91.45; H, 5.78; N, 2.77 [M < + >]: 1010

[[ 합성예Synthetic example 209] 화합물 230의 제조 209] Preparation of Compound 230

합성예 205에서 화합물 226-A를 화합물 230-A(9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 230-C (diphenylamine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 230-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 230-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.19; H, 5.09; N, 2.72 [M+]:1028
Elemental Analysis: C, 92.19; H, 5.09; N, 2.72 [M < + >]: 1028

[[ 합성예Synthetic example 210] 화합물 231의 제조 210] Preparation of Compound 231

합성예 205에서 화합물 226-A를 화합물 231-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine)로 대체하고, 화합물 226-C를 화합물 231-C (diphenylamine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 226-A with compound 231-A (9,9-dimethyl-N-phenyl-9H-fluoren-3-amine) in Synthesis Example 205, and replaced compound 226-C with compound 231-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.19; H, 5.09; N, 2.72 [M+]:1028
Elemental Analysis: C, 92.19; H, 5.09; N, 2.72 [M < + >]: 1028

[[ 합성예Synthetic example 211] 화합물 232의 제조 211] Preparation of Compound 232

합성예 205에서 화합물 226-A를 화합물 232-A (N-(4-tert-butylphenyl)-3-methylaniline)로 대체하고, 화합물 226-C를 화합물 232-C (diphenylamine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A is replaced with compound 232-A (N- (4-tert-butylphenyl) -3-methylaniline), and compound 226-C is replaced with compound 232-C (diphenylamine), and compound 226 Synthesis was carried out using the same method as that of.

Elemental Analysis: C, 91.62; H, 5.54; N, 2.85 [M+]:982
Elemental Analysis: C, 91.62; H, 5.54; N, 2.85 [M < + >]: 982

[[ 합성예Synthetic example 212] 화합물 233의 제조 212] Preparation of Compound 233

합성예 205에서 화합물 226-A를 화합물 233-A (4-tert-butyl-N-(4-(trimethylsilyl)phenyl)aniline)로 대체하고, 화합물 226-C를 화합물 233-C (diphenylamine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 226-A with compound 233-A (4-tert-butyl-N- (4- (trimethylsilyl) phenyl) aniline) in Synthesis Example 205 and replaced compound 226-C with compound 233-C (diphenylamine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 88.81; H, 5.81; N, 2.69; Si, 2.70 [M+]:1040
Elemental Analysis: C, 88.81; H, 5.81; N, 2.69; Si, 2.70 [M < + >]: 1040

[[ 합성예Synthetic example 213] 화합물 234의 제조 213] Preparation of Compound 234

합성예 205에서 화합물 226-A를 화합물 234-A (N-phenylbiphenyl-4-amine)로 대체하고, 화합물 226-C를 화합물 234-C (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 234-A (N-phenylbiphenyl-4-amine), and compound 226-C was replaced with compound 234-C (9,9-dimethyl-N-phenyl-9H-fluoren- 2-amine), using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.36; H, 5.11; N, 2.53 [M+]:1104
Elemental Analysis: C, 92.36; H, 5.11; N, 2.53 [M < + >]: 1104

[[ 합성예Synthetic example 214] 화합물 235의 제조 214] Preparation of Compound 235

합성예 205에서 화합물 226-A를 화합물 235-A (N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 235-C (diphenylamine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 235-A (N- (biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 235- Substituted with C (diphenylamine), it could be synthesized using the same method as the synthesis of compound 226.

Elemental Analysis: C, 92.36; H, 5.11; N, 2.53 [M+]:1104
Elemental Analysis: C, 92.36; H, 5.11; N, 2.53 [M < + >]: 1104

[[ 합성예Synthetic example 215] 화합물 236의 제조 215] Preparation of Compound 236

합성예 205에서 화합물 226-A를 화합물 236-A (4-tert-butyl-N-phenylaniline)로 대체하고, 화합물 226-C를 화합물 236-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 236-A (4-tert-butyl-N-phenylaniline), and compound 226-C was replaced with compound 236-C (11,11-dimethyl-N-phenyl-11H- Substituted with benzo [a] fluoren-9-amine), it could be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.03; H, 5.50; N, 2.47 [M+]:1134
Elemental Analysis: C, 92.03; H, 5.50; N, 2.47 [M < + >]: 1134

[[ 합성예Synthetic example 216] 화합물 237의 제조 216] Preparation of Compound 237

합성예 205에서 화합물 226-A를 화합물 237-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 226-C를 화합물 237-C (N-phenylbenzo[d]thiazol-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 226-A is replaced with Compound 237-A (N-phenylnaphthalen-2-amine) in Synthesis Example 205, and compound 226-C is replaced with compound 237-C (N-phenylbenzo [d] thiazol-2-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 88.29; H, 4.45; N, 4.12; S, 3.14 [M+]:1019
Elemental Analysis: C, 88.29; H, 4.45; N, 4.12; S, 3.14 [M +]: 1019

[[ 합성예Synthetic example 217] 화합물 238의 제조 217] Preparation of Compound 238

합성예 205에서 화합물 226-A를 화합물 238-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 238-C (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 238-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 238-C (11,11- Substituted with dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.43; H, 5.23; N, 2.34 [M+]:1194
Elemental Analysis: C, 92.43; H, 5.23; N, 2.34 [M < + >]: 1194

[[ 합성예Synthetic example 218] 화합물 239의 제조 218] Preparation of Compound 239

합성예 205에서 화합물 226-A를 화합물 239-A (9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 239-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 239-A (9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 239-C (N- (4 -tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 91.89; H, 5.80; N, 2.30 [M+]:1214
Elemental Analysis: C, 91.89; H, 5.80; N, 2.30 [M +]: 1214

[[ 합성예Synthetic example 219] 화합물 240의 제조 219] Preparation of Compound 240

합성예 205에서 화합물 226-A를 화합물 240-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 240-C (7,7-dimethyl-N-phenyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 240-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 240-C (7,7- dimethyl-N-phenyl-7H-benzo [c] fluoren-9-amine), which was synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.43; H, 5.23; N, 2.34 [M+]:1194
Elemental Analysis: C, 92.43; H, 5.23; N, 2.34 [M < + >]: 1194

[[ 합성예Synthetic example 220] 화합물 241의 제조 220] Preparation of Compound 241

합성예 205에서 화합물 226-A를 화합물 241-A (11,11-dimethyl-N-phenyl-11H-benzo[a]fluoren-9-amine)로 대체하고, 화합물 226-C를 화합물 241-C (11,11-dimethyl-N-(naphthalen-2-yl)-11H-benzo[a]fluoren-9-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 241-A (11,11-dimethyl-N-phenyl-11H-benzo [a] fluoren-9-amine), and compound 226-C was replaced with compound 241-C ( 11,11-dimethyl-N- (naphthalen-2-yl) -11H-benzo [a] fluoren-9-amine) could be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.70; H, 5.13; N, 2.16 [M+]:1294
Elemental Analysis: C, 92.70; H, 5.13; N, 2.16 [M < + >]: 1294

[[ 합성예Synthetic example 221] 화합물 242의 제조 221] Preparation of Compound 242

합성예 205에서 화합물 226-A를 화합물 242-A (9,9-dimethyl-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 242-C (N-(4-tert-butylphenyl)-9,9-dimethyl-9H-fluoren-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 242-A (9,9-dimethyl-N- (naphthalen-2-yl) -9H-fluoren-2-amine), and compound 226-C was replaced with compound 242-. Substituted with C (N- (4-tert-butylphenyl) -9,9-dimethyl-9H-fluoren-2-amine), it could be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.12; H, 5.64; N, 2.24 [M+]:1250
Elemental Analysis: C, 92.12; H, 5.64; N, 2.24 [M +]: 1 250

[[ 합성예Synthetic example 222] 화합물 243의 제조 222] Preparation of Compound 243

합성예 205에서 화합물 226-A를 화합물 243-A (7,7-dimethyl-N-p-tolyl-7H-benzo[c]fluoren-9-amine)로 대체하고, 화합물 226-C를 화합물 243-C (N-(4-isopropylphenyl)-7,7-dimethyl-7H-benzo[c]fluoren-9-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 243-A (7,7-dimethyl-Np-tolyl-7H-benzo [c] fluoren-9-amine), and compound 226-C was replaced with compound 243-C ( Substituted by N- (4-isopropylphenyl) -7,7-dimethyl-7H-benzo [c] fluoren-9-amine), the synthesis was carried out using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.20; H, 5.67; N, 2.13 [M+]:1314
Elemental Analysis: C, 92.20; H, 5.67; N, 2.13 [M < + >]: 1314

[[ 합성예Synthetic example 223] 화합물 244의 제조 223] Preparation of Compound 244

합성예 205에서 화합물 226-A를 화합물 244-A (N-phenylnaphthalen-2-amine)로 대체하고, 화합물 226-C를 화합물 244-C (5-phenyl-N-phenylbiphenyl-3-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 226-A with compound 244-A (N-phenylnaphthalen-2-amine) in Synthesis Example 205 and replaced compound 226-C with compound 244-C (5-phenyl-N-phenylbiphenyl-3-amine) Thus, the synthesis was carried out using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.61; H, 4.88; N, 2.51 [M+]: 1114
Elemental Analysis: C, 92.61; H, 4.88; N, 2.51 [M < + >]: 1114

[[ 합성예Synthetic example 224] 화합물 245의 제조 224] Preparation of Compound 245

합성예 205에서 화합물 226-A를 화합물 245-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 245-C (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 245-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 245-C (N, 9, 9-triphenyl-9H-fluoren-2-amine), using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.71; H, 5.08; N, 2.21 [M+]:1268
Elemental Analysis: C, 92.71; H, 5.08; N, 2.21 [M < + >]: 1268

[[ 합성예Synthetic example 225] 화합물 246의 제조 225] Preparation of Compound 246

합성예 205에서 화합물 226-A를 화합물 246-A (N,9,9-triphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 246-C (N-(4-tert-butylphenyl)-9,9-diphenyl-9H-fluoren-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 246-A (N, 9,9-triphenyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 246-C (N- (4-tert -butylphenyl) -9,9-diphenyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.78; H, 5.28; N, 1.93 [M+]:1148
Elemental Analysis: C, 92.78; H, 5. 28; N, 1.93 [M < + >]: 1148

[[ 합성예Synthetic example 226] 화합물 247의 제조 226] Preparation of Compound 247

합성예 205에서 화합물 226-A를 화합물 247-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 226-C를 화합물 247-C (4-(naphthalen-1-yl)-N-phenylaniline)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 247-A (9,9-dimethyl-N-phenyl-9H-fluoren-2-amine), and compound 226-C was replaced with compound 247-C (4- (naphthalen) -1-yl) -N-phenylaniline) can be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.52; H, 5.06; N, 2.42 [M+]:1154
Elemental Analysis: C, 92.52; H, 5.06; N, 2.42 [M < + >]: 1154

[[ 합성예Synthetic example 227] 화합물 248의 제조 227] Preparation of Compound 248

합성예 205에서 화합물 226-A를 화합물 248-A (N-phenylfluoranthen-3-amine)로 대체하고, 화합물 226-C를 화합물 248-C (7,7-dimethyl-N-phenyl-7H-benzo[de]anthracen-9-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 248-A (N-phenylfluoranthen-3-amine), and compound 226-C was replaced with compound 248-C (7,7-dimethyl-N-phenyl-7H-benzo [ de] anthracen-9-amine), using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.81; H, 4.86; N, 2.33 [M+]: 1202
Elemental Analysis: C, 92.81; H, 4.86; N, 2.33 [M < + >]: 1202

[[ 합성예Synthetic example 228] 화합물 249의 제조 228] Preparation of Compound 249

합성예 205에서 화합물 226-A를 화합물 249-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylaniline)로 대체하고, 화합물 226-C를 화합물 249-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하여, 화합물 226의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 205, compound 226-A was replaced with compound 249-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylaniline), and compound 226-C was replaced with compound 249-C ( N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) could be synthesized using the same method as the synthesis of Compound 226.

Elemental Analysis: C, 92.61; H, 5.33; N, 2.06 [M+]:1360
Elemental Analysis: C, 92.61; H, 5. 33; N, 2.06 [M +]: 1360

[[ 합성예Synthetic example 229] 화합물 298의 제조 229] Preparation of Compound 298

[합성예 229-1] 화합물 298-1의 제조 Synthesis Example 229-1 Preparation of Compound 298-1

합성예 1-1의 화합물 7-A를 화합물 298-A (9,9-dimethyl-N,7-diphenyl-9H-fluoren-2-amine)로 대체하고, 화합물 7-1의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-A of Synthesis Example 1-1 was replaced with Compound 298-A (9,9-dimethyl-N, 7-diphenyl-9H-fluoren-2-amine), and the same method as for the synthesis of Compound 7-1 was performed. It could synthesize | combine using.

[합성예 229-2] 화합물 298-2의 제조 Synthesis Example 229-2 Preparation of the Compound 298-2.

합성예 1-2의 화합물 7-1을 화합물 298-1로, 화합물 7-B를 화합물 298-B (2-bromonaphthalene)로 대체하고, 화합물 7-2의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-1 of Synthesis Example 1-2 could be replaced with Compound 298-1, Compound 7-B with Compound 298-B (2-bromonaphthalene), and synthesized using the same method as the synthesis of Compound 7-2. there was.

[합성예 229-3] 화합물 298-3의 제조 Synthesis Example 229-3 Preparation of the Compound 298-3.

합성예 1-3의 화합물 7-2를 화합물 298-2로 대체하고, 화합물 7-3의 합성과 동일한 방법을 이용하여 합성할 수 있었다. Compound 7-2 of Synthesis Example 1-3 was replaced with compound 298-2, and was synthesized using the same method as the synthesis of Compound 7-3.

[합성예 229-4] 화합물 298의 제조 Synthesis Example 229-4 Preparation of Compound 298

합성예 1-4의 화합물 7-3을 화합물 298-3으로 대체하고, 화합물 7-C를 화합물 298-C (N-(4-tert-butylphenyl)-9,9-dimethyl-7-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 7(합성예 1-4)의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replace compound 7-3 of Synthesis Example 1-4 with compound 298-3, and replace compound 7-C with compound 298-C (N- (4-tert-butylphenyl) -9,9-dimethyl-7-phenyl-9H -fluoren-2-amine) and synthesized using the same method as the synthesis of Compound 7 (Synthesis Example 1-4).

Elemental Analysis: C, 91.66; H, 6.02; N, 2.32 [M+]:1204Elemental Analysis: C, 91.66; H, 6.02; N, 2.32 [M < + >]: 1204

[[ 합성예Synthetic example 230] 화합물 299의 제조 230] Preparation of Compound 299

합성예 229에서 화합물 298-A를 화합물 299-A (N-(4-tert-butylphenyl)-9,9-dimethyl-7-phenyl-9H-fluoren-2-amine)로 대체하고, 화합물 298-C를 화합물 299-C (9,9-dimethyl-N-(naphthalen-1-yl)-7-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Compound 298-A was replaced with compound 299-A (N- (4-tert-butylphenyl) -9,9-dimethyl-7-phenyl-9H-fluoren-2-amine) in Synthesis Example 229, and Compound 298-C To 299-C (9,9-dimethyl-N- (naphthalen-1-yl) -7-phenyl-9H-fluoren-2-amine) to be synthesized using the same method as for the synthesis of compound 298. Could.

Elemental Analysis: C, 91.83; H, 5.94; N, 2.23 [M+]:1254
Elemental Analysis: C, 91.83; H, 5.94; N, 2.23 [M < + >]: 1254

[[ 합성예Synthetic example 231] 화합물 300의 제조 231] Preparation of Compound 300

합성예 229에서 화합물 298-A를 화합물 300-A (9,9-dimethyl-N,7-di(naphthalen-1-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 298-C를 화합물 300-C (9,9-dimethyl-N-(naphthalen-1-yl)-7-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 229, Compound 298-A was replaced with Compound 300-A (9,9-dimethyl-N, 7-di (naphthalen-1-yl) -9H-fluoren-2-amine), and Compound 298-C was replaced with Compound 300-C (9,9-dimethyl-N- (naphthalen-1-yl) -7-phenyl-9H-fluoren-2-amine) can be synthesized using the same method as the synthesis of Compound 298. there was.

Elemental Analysis: C, 92.42; H, 5.43; N, 2.16 [M+]:1298
Elemental Analysis: C, 92.42; H, 5. 43; N, 2.16 [M < + >]: 1298

[[ 합성예Synthetic example 232] 화합물 301의 제조 232] Preparation of Compound 301

합성예 229에서 화합물 298-A를 화합물 301-A (N-(4-tert-butylphenyl)-9,9-dimethyl-7-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 298-C를 화합물 301-C (9,9-dimethyl-7-(naphthalen-2-yl)-N-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 298-A with compound 301-A (N- (4-tert-butylphenyl) -9,9-dimethyl-7- (naphthalen-2-yl) -9H-fluoren-2-amine) in Synthesis Example 229 And replacing compound 298-C with compound 301-C (9,9-dimethyl-7- (naphthalen-2-yl) -N-phenyl-9H-fluoren-2-amine), the same as the synthesis of compound 298 It could be synthesized using the method.

Elemental Analysis: C, 91.99; H, 5.87; N, 2.15 [M+]:1304
Elemental Analysis: C, 91.99; H, 5.87; N, 2.15 [M < + >]: 1304

[[ 합성예Synthetic example 233] 화합물 302의 제조 233] Preparation of Compound 302

합성예 229에서 화합물 298-A를 화합물 302-A (N-(4-tert-butylphenyl)-9,9-dimethyl-7-(naphthalen-1-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 298-C를 화합물 302-C (9,9-dimethyl-7-(naphthalen-1-yl)-N-(naphthalen-2-yl)-9H-fluoren-2-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 298-A with compound 302-A (N- (4-tert-butylphenyl) -9,9-dimethyl-7- (naphthalen-1-yl) -9H-fluoren-2-amine) in Synthesis Example 229 Compound 298-C with compound 302-C (9,9-dimethyl-7- (naphthalen-1-yl) -N- (naphthalen-2-yl) -9H-fluoren-2-amine), Synthesis was carried out using the same method as the synthesis of Compound 298.

Elemental Analysis: C, 92.13; H, 5.80; N, 2.07 [M+]:1354
Elemental Analysis: C, 92.13; H, 5.80; N, 2.07 [M < + >]: 1354

[[ 합성예Synthetic example 234] 화합물 303의 제조 234] Preparation of Compound 303

합성예 229에서 화합물 298-A를 화합물 303-A (N-(4-tert-butylphenyl)-9,9-dimethyl-7-(naphthalen-1-yl)-9H-fluoren-2-amine)로 대체하고, 화합물 298-C를 화합물 303-C (N-(4-isopropylphenyl)-9,9-dimethyl-7-phenyl-9H-fluoren-2-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.Replaced compound 298-A with compound 303-A (N- (4-tert-butylphenyl) -9,9-dimethyl-7- (naphthalen-1-yl) -9H-fluoren-2-amine) in Synthesis Example 229 Compound 298-C was replaced with compound 303-C (N- (4-isopropylphenyl) -9,9-dimethyl-7-phenyl-9H-fluoren-2-amine) to obtain the same method as for the synthesis of compound 298. It could synthesize | combine using.

Elemental Analysis: C, 91.63; H, 6.21; N, 2.16 [M+]: 1296
Elemental Analysis: C, 91.63; H, 6.21; N, 2.16 [M +]: 1296

[[ 합성예Synthetic example 235] 화합물 304의 제조 235] Preparation of Compound 304

합성예 229에서 화합물 298-A를 화합물 304-A (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-2,3,5,6-tetramethylaniline)로 대체하고, 화합물 298-C를 화합물 304-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-3,5-dimethylaniline)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 229, Compound 298-A was replaced with Compound 304-A (N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) -2,3,5,6-tetramethylaniline) , Compound 298-C was replaced with Compound 304-C (N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) -3,5-dimethylaniline), the same as the synthesis of Compound 298 It could be synthesized using the method.

Elemental Analysis: C, 91.52; H, 6.21; N, 2.27 [M+]:1232
Elemental Analysis: C, 91.52; H, 6.21; N, 2.27 [M +]: 1 232

[[ 합성예Synthetic example 236] 화합물 305의 제조 236] Preparation of Compound 305

합성예 229에서 화합물 298-A를 화합물 305-A (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)naphthalen-2-amine)로 대체하고, 화합물 298-C를 화합물 305-C (N-(4-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-3,5-dimethylaniline)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 229, compound 298-A was replaced with compound 305-A (N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) naphthalen-2-amine) and compound 298-C Was synthesized using the same method as the synthesis of Compound 298, by replacing with Compound 305-C (N- (4- (9,9-dimethyl-9H-fluoren-2-yl) phenyl) -3,5-dimethylaniline) Could.

Elemental Analysis: C, 91.97; H, 5.75; N, 2.28 [M+]:1226
Elemental Analysis: C, 91.97; H, 5.75; N, 2.28 [M < + >]: 1226

[[ 합성예Synthetic example 237] 화합물 306의 제조 237] Preparation of Compound 306

합성예 229에서 화합물 298-A를 화합물 306-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylaniline)로 대체하고, 화합물 298-C를 화합물 306-C (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylnaphthalen-1-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 229, compound 298-A was replaced with compound 306-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -N-phenylaniline), and compound 298-C was replaced with compound 306-C ( 4- (9,9-dimethyl-9H-fluoren-2-yl) -N-phenylnaphthalen-1-amine) could be synthesized using the same method as the synthesis of Compound 298.

Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M+]: 1198
Elemental Analysis: C, 92.12; H, 5.55; N, 2.34 [M < + >]: 1198

[[ 합성예Synthetic example 238] 화합물 307의 제조 238] Preparation of Compound 307

합성예 229에서 화합물 298-A를 화합물 307-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylnaphthalen-1-amine 로 대체하고, 화합물 298-C를 화합물 307-C (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-(3,5-dimethylphenyl)naphthalen-1-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 229, compound 298-A was replaced with compound 307-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -N-phenylnaphthalen-1-amine, and compound 298-C was replaced with compound 307 -C (4- (9,9-dimethyl-9H-fluoren-2-yl) -N- (3,5-dimethylphenyl) naphthalen-1-amine), using the same method as for the synthesis of compound 298 Could be synthesized.

Elemental Analysis: C, 92.13; H, 5.68; N, 2.19 [M+]: 1276
Elemental Analysis: C, 92.13; H, 5.68; N, 2.19 [M < + >]: 1276

[[ 합성예Synthetic example 239] 화합물 308의 제조 239] Preparation of Compound 308

합성예 229에서 화합물 298-A를 화합물 308-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-(4-isopropylphenyl)naphthalen-1-amine)로 대체하고, 화합물 298-C를 화합물 308-C (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-p-tolylnaphthalen-1-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 229, the compound 298-A was replaced with the compound 308-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -N- (4-isopropylphenyl) naphthalen-1-amine), and the compound Synthesis using the same method as for the synthesis of Compound 298, replacing 298-C with Compound 308-C (4- (9,9-dimethyl-9H-fluoren-2-yl) -Np-tolylnaphthalen-1-amine) Could.

Elemental Analysis: C, 91.99; H, 5.87; N, 2.15 [M+]:1304
Elemental Analysis: C, 91.99; H, 5.87; N, 2.15 [M < + >]: 1304

[[ 합성예Synthetic example 240] 화합물 309의 제조 240] Preparation of Compound 309

합성예 229에서 화합물 298-A를 화합물 309-A (4-(9,9-dimethyl-9H-fluoren-2-yl)-N-phenylnaphthalen-1-amine)로 대체하고, 화합물 298-C를 화합물 309-C (N-(4-tert-butylphenyl)-4-(9,9-dimethyl-9H-fluoren-2-yl)naphthalen-1-amine)로 대체하여, 화합물 298의 합성과 동일한 방법을 이용하여 합성할 수 있었다.In Synthesis Example 229, compound 298-A was replaced with compound 309-A (4- (9,9-dimethyl-9H-fluoren-2-yl) -N-phenylnaphthalen-1-amine), and compound 298-C was replaced with 309-C (N- (4-tert-butylphenyl) -4- (9,9-dimethyl-9H-fluoren-2-yl) naphthalen-1-amine), using the same method as the synthesis of Compound 298 Could be synthesized.

Elemental Analysis: C, 91.99; H, 5.87; N, 2.15 [M+]: 1304
Elemental Analysis: C, 91.99; H, 5.87; N, 2.15 [M < + >]: 1304

2. 유기 2. Organic 전계Field 발광 소자 제조 Light emitting device manufacturing

[[ 실시예Example 1]  One]

하기와 같은 방법으로 유기 전계 발광 소자를 제조하였다.An organic electroluminescent device was fabricated in the following manner.

ITO(Indium tin oxide)가 1500Å의 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 5분간 세정 한 후 진공 층착기로 기판을 이송하였다. 이후, 하기 구조의 유기 전계 발광 소자를 제작하였다. The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor. Thereafter, an organic EL device having the following structure was manufactured.

구체적으로, 상기 준비된 ITO(양극) 위에 DNTPD(N,N -bis-[4-(di-mtolylamino)phenyl]-N,N -diphenylbiphenyl-4,4 -diamine)를 800 Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였고, 상기 정공 주입층 위에 정공 수송 물질인 α-NPB(N, N-di(naphthalene-1-yl)-N, N-diphenylbenzidine)을 300 Å의 두께로 진공 증착하여 정공 수송층을 형성하였다.Specifically, thermal vacuum deposition of DNTPD (N, N -bis- [4- (di-mtolylamino) phenyl] -N, N -diphenylbiphenyl-4,4-diamine) on the prepared ITO (anode) to a thickness of 800 kPa A hole injection layer was formed, and a hole-transporting material α-NPB ( N , N- di (naphthalene-1-yl) -N , N- diphenylbenzidine) was vacuum deposited to a thickness of 300 두께 on the hole injection layer. A transport layer was formed.

그 위에 호스트 물질로서 하기 H1으로 표시되는 화합물을 사용하고 도펀트로서 상기 합성예 1에서 제조된 화합물 7을 5% 도핑하여 250Å의 두께로 진공 증착하여 발광층을 형성하였고, 상기 발광층 위에 전자 수송 물질인 Alq3을 400 Å의 두께로 진공 증착하여 전자 수송층을 형성하였다. 그 후, 전자 주입 물질인 LiF를 10 Å의 두께로 증착하여 전자 주입층을 형성하였고, 그 위에 알루미늄을 1000 Å의 두께로 진공 증착하여 음극을 형성하였다.A compound represented by the following H1 is used thereon as a host material and 5% of the compound 7 prepared in Synthesis Example 1 as a dopant is vacuum deposited to a thickness of 250 kV to form a light emitting layer, and Alq3, which is an electron transporting material, is formed on the light emitting layer. Was vacuum deposited to a thickness of 400 kPa to form an electron transporting layer. Thereafter, LiF, an electron injection material, was deposited to a thickness of 10 kW to form an electron injection layer, and aluminum was vacuum deposited to a thickness of 1000 kW to form a cathode.

제조한 소자를 당업계에 공지된 방법으로 발광 파장을 측정한 결과 최대 발광 파장은 523nm 이었다.The maximum emission wavelength was 523 nm as a result of measuring the emission wavelength of the manufactured device by a method known in the art.

Figure 112011095402950-pat00035
Figure 112011095402950-pat00035

[[ 실시예Example 2~240]  2 ~ 240]

발광층 형성시 상기 합성예 1에서 제조된 화합물 7 대신 상기 합성예 2 내지 240에서 제조된 화합물(화합물 2 내지 12, 16 내지 18, 37 내지 249 및 298 내지 309)을 각각 사용한 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다. 제조한 소자를 당업계에 공지된 방법으로 발광 파장을 측정한 결과 최대 발광 파장은 510nm 내지 528nm이었다.
Except for using the compounds prepared in Synthesis Examples 2 to 240 (Compounds 2 to 12, 16 to 18, 37 to 249 and 298 to 309) instead of Compound 7 prepared in Synthesis Example 1 when forming the emission layer, An organic electroluminescent device was manufactured in the same manner as in Example 1. As a result of measuring the emission wavelength of the manufactured device by a method known in the art, the maximum emission wavelength was 510 nm to 528 nm.

[[ 비교예Comparative example 1]  One]

발광층 형성시 상기 합성예 1에서 제조된 화합물 7 대신 하기 X로 표시되는 화합물을 사용한 것을 제외하고는, 실시예 1과 동일한 방법으로 유기 전계 발광 소자를 제작하였다. 제조한 소자를 당업계에 공지된 방법으로 발광 파장을 측정한 결과 최대 발광 파장은 521nm 이었다.An organic electroluminescent device was manufactured in the same manner as in Example 1, except that the compound represented by the following X was used instead of the compound 7 prepared in Synthesis Example 1 when forming the emission layer. The maximum emission wavelength was 521 nm as a result of measuring the emission wavelength of the manufactured device by a method known in the art.

Figure 112011095402950-pat00036
Figure 112011095402950-pat00036

[[ 실험예Experimental Example ]]

실시예 1 내지 240 및 비교예 1에서 제작된 유기 전계 발광 소자에 대하여 전류밀도 50mA/㎠에서의 구동전압 및 발광 효율을 측정하였고, 그 결과를 하기 표 1에 나타내었다. The driving voltage and the luminous efficiency at the current density of 50 mA / cm 2 were measured for the organic electroluminescent devices manufactured in Examples 1 to 240 and Comparative Example 1, and the results are shown in Table 1 below.

화합물compound Voltage(V)Voltage (V) Efficiency(cd/A)Efficiency (cd / A) 화합물compound Voltage(V)Voltage (V) Efficiency(cd/A)Efficiency (cd / A) 1One 6.56.5 20.820.8 142142 5.85.8 19.519.5 22 6.46.4 20.020.0 143143 5.75.7 19.419.4 33 6.46.4 19.919.9 144144 5.75.7 20.820.8 44 6.36.3 19.419.4 145145 5.95.9 20.220.2 55 6.46.4 19.219.2 146146 5.75.7 20.320.3 66 6.36.3 20.820.8 147147 5.85.8 19.519.5 77 6.26.2 19.419.4 148148 5.85.8 19.519.5 88 6.46.4 19.519.5 149149 6.06.0 20.020.0 99 6.46.4 20.020.0 150150 5.75.7 20.420.4 1010 6.46.4 20.820.8 151151 5.85.8 20.320.3 1111 6.26.2 19.719.7 152152 5.85.8 20.520.5 1212 6.46.4 19.719.7 153153 5.75.7 20.720.7 1616 6.06.0 19.419.4 154154 6.06.0 20.620.6 1717 6.16.1 19.019.0 155155 5.75.7 20.820.8 1818 6.46.4 18.918.9 156156 5.75.7 20.820.8 3737 6.46.4 18.918.9 157157 6.16.1 20.320.3 3838 6.56.5 19.019.0 158158 6.16.1 20.420.4 3939 6.46.4 19.119.1 159159 6.06.0 20.020.0 4040 5.75.7 19.519.5 160160 6.16.1 20.420.4 4141 5.75.7 20.820.8 161161 6.06.0 20.420.4 4242 5.85.8 20.020.0 162162 6.16.1 20.320.3 4343 5.65.6 20.420.4 163163 6.26.2 20.320.3 4444 5.75.7 20.320.3 164164 6.16.1 19.519.5 4545 5.95.9 20.320.3 165165 5.95.9 20.420.4 4646 5.75.7 20.820.8 166166 6.06.0 20.320.3 4747 5.75.7 20.920.9 167167 6.16.1 20.420.4 4848 6.06.0 20.220.2 168168 5.85.8 20.220.2 4949 6.16.1 20.020.0 169169 5.85.8 20.220.2 5050 5.75.7 20.220.2 170170 6.06.0 20.820.8 5151 5.75.7 20.820.8 171171 6.06.0 20.620.6 5252 5.85.8 20.720.7 172172 5.85.8 20.220.2 5353 5.55.5 20.120.1 173173 5.95.9 20.820.8 5454 5.75.7 20.220.2 174174 5.85.8 20.220.2 5555 5.95.9 20.120.1 175175 6.06.0 20.420.4 5656 5.75.7 20.220.2 176176 6.16.1 20.220.2 5757 5.75.7 20.820.8 177177 6.26.2 20.220.2 5858 6.26.2 20.120.1 178178 5.75.7 19.519.5 5959 6.16.1 20.220.2 179179 5.75.7 20.820.8 6060 6.36.3 20.820.8 180180 6.16.1 20.020.0 6161 6.26.2 20.820.8 181181 6.06.0 20.120.1 6262 6.16.1 20.520.5 182182 5.95.9 20.020.0 6363 6.26.2 20.520.5 183183 6.06.0 20.320.3 6464 6.26.2 20.320.3 184184 6.16.1 20.420.4 6565 6.36.3 20.820.8 185185 6.26.2 20.020.0 6666 5.95.9 20.420.4 186186 5.95.9 19.519.5 6767 6.26.2 20.420.4 187187 5.95.9 20.020.0 6868 6.26.2 20.820.8 188188 6.26.2 20.720.7 6969 6.56.5 20.520.5 189189 5.95.9 20.520.5 7070 5.75.7 20.320.3 190190 5.75.7 20.820.8 7171 5.85.8 20.320.3 191191 5.65.6 19.519.5 7272 6.06.0 20.320.3 192192 5.75.7 20.820.8 7373 6.06.0 20.420.4 193193 5.85.8 20.820.8 7474 5.95.9 20.820.8 194194 5.95.9 20.820.8 7575 6.06.0 20.820.8 195195 5.95.9 20.220.2 7676 6.06.0 20.820.8 196196 5.85.8 20.420.4 7777 6.06.0 20.020.0 197197 6.16.1 20.020.0 7878 5.95.9 20.120.1 198198 6.26.2 19.919.9 7979 6.06.0 19.519.5 199199 6.36.3 20.020.0 8080 6.16.1 20.020.0 200200 6.36.3 19.519.5 8181 6.06.0 19.519.5 201201 6.26.2 20.020.0 8282 5.65.6 20.220.2 202202 5.95.9 20.020.0 8383 5.95.9 19.519.5 203203 5.95.9 20.120.1 8484 6.26.2 20.020.0 204204 5.85.8 20.220.2 8585 5.95.9 20.020.0 205205 5.85.8 20.820.8 8686 5.95.9 20.820.8 206206 5.95.9 20.820.8 8787 6.26.2 20.420.4 207207 6.06.0 20.420.4 8888 5.95.9 19.519.5 208208 5.95.9 20.220.2 8989 5.85.8 20.820.8 209209 6.16.1 20.820.8 9090 5.95.9 20.320.3 210210 6.16.1 20.320.3 9191 6.16.1 20.420.4 211211 6.06.0 20.320.3 9292 6.36.3 20.820.8 212212 6.16.1 20.020.0 9393 6.46.4 20.820.8 213213 6.06.0 20.520.5 9494 5.75.7 20.020.0 214214 5.85.8 20.420.4 9595 6.16.1 20.120.1 215215 5.85.8 20.420.4 9696 5.95.9 20.820.8 216216 5.95.9 19.519.5 9797 6.16.1 20.820.8 217217 5.85.8 20.820.8 9898 5.95.9 20.020.0 218218 5.85.8 20.820.8 9999 6.26.2 20.520.5 219219 6.06.0 20.720.7 100100 5.95.9 19.519.5 220220 6.06.0 20.720.7 101101 5.95.9 20.020.0 221221 6.16.1 20.520.5 102102 5.85.8 20.220.2 222222 6.26.2 20.020.0 103103 6.06.0 20.820.8 223223 6.06.0 19.519.5 104104 5.95.9 20.120.1 224224 5.95.9 19.919.9 105105 5.95.9 20.220.2 225225 5.95.9 20.020.0 106106 6.16.1 20.420.4 226226 6.26.2 20.120.1 107107 5.95.9 20.420.4 227227 5.95.9 20.820.8 108108 6.26.2 20.120.1 228228 6.06.0 20.120.1 109109 6.06.0 20.020.0 229229 6.06.0 20.020.0 110110 5.95.9 20.520.5 230230 6.06.0 20.420.4 111111 5.75.7 19.519.5 231231 5.95.9 20.820.8 112112 5.95.9 19.519.5 232232 5.95.9 20.520.5 113113 5.75.7 20.220.2 233233 6.16.1 20.020.0 114114 5.95.9 20.220.2 234234 5.95.9 19.519.5 115115 5.95.9 20.420.4 235235 6.26.2 20.020.0 116116 6.06.0 20.320.3 236236 6.06.0 20.020.0 117117 6.46.4 20.420.4 237237 5.95.9 20.220.2 118118 5.75.7 20.820.8 238238 5.85.8 20.420.4 119119 5.75.7 20.820.8 239239 5.95.9 20.520.5 120120 5.95.9 20.020.0 240240 6.06.0 20.820.8 121121 5.85.8 20.520.5 241241 5.95.9 20.820.8 122122 5.65.6 20.320.3 242242 6.16.1 20.720.7 123123 5.95.9 20.420.4 243243 6.16.1 19.519.5 124124 5.85.8 20.820.8 244244 6.06.0 20.020.0 125125 6.06.0 20.620.6 245245 6.06.0 20.320.3 126126 6.26.2 20.820.8 246246 5.95.9 20.420.4 127127 5.95.9 19.919.9 247247 6.06.0 20.520.5 128128 6.16.1 20.820.8 248248 6.06.0 20.920.9 129129 5.95.9 20.020.0 249249 5.95.9 20.720.7 130130 5.95.9 19.919.9 298298 5.65.6 21.821.8 131131 5.75.7 20.020.0 299299 5.75.7 21.921.9 132132 5.65.6 20.820.8 300300 5.75.7 22.222.2 133133 5.95.9 19.319.3 301301 5.85.8 21.021.0 134134 5.85.8 19.319.3 302302 5.65.6 21.821.8 135135 6.06.0 19.519.5 303303 5.75.7 21.821.8 136136 5.95.9 20.820.8 304304 5.65.6 21.921.9 137137 6.06.0 19.319.3 305305 5.85.8 21.921.9 138138 5.95.9 20.820.8 306306 5.85.8 21.521.5 139139 5.95.9 19.719.7 307307 5.85.8 21.921.9 140140 5.85.8 20.820.8 308308 5.95.9 21.821.8 141141 5.85.8 20.820.8 309309 5.85.8 22.122.1 비교예 1Comparative Example 1 6.86.8 17.217.2

상기 표 1를 참조하면, 본 발명의 화합물을 호스트로 사용한 실시예 1 내지 240은 비교예 1과 유사한 색 순도(최대 발광 파장이 유사하게 나타남)를 보이면서 구동전압과 효율면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.Referring to Table 1, Examples 1 to 240 using the compound of the present invention as a host shows excellent performance in terms of driving voltage and efficiency while showing similar color purity (maximum emission wavelength is shown) similar to Comparative Example 1 I could confirm it.

Claims (7)

하기 화학식 1로 표시되는 화합물:
[화학식 1]
Figure 112011095402950-pat00037

상기 화학식 1에서,
Ar1 내지 Ar4 중 하나 이상은 수소 또는 중수소를 제외한 치환기이고;
Ar1과 Ar4가 서로 같을 경우 Ar2와 Ar3는 서로 다른 치환기이고, Ar1와 Ar3가 서로 같을 경우 Ar2와 Ar4는 서로 다른 치환기이며;
Ar1 내지 Ar4 는 서로 같거나 다르고, 수소, 중수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, C5~C40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아미노기, C6~C40의 디아릴아미노기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기 및 C3~C40의 헤테로시클로알킬기로 이루어진 군에서 선택되며;
R1 및 R2는 서로 같거나 다르고, 수소, 중수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, C5~C40의 헤테로아릴기, C6~C40의 아릴아미노기, C6~C40의 디아릴아미노기, C6~C40의 아릴알킬기, C3~C40의 시클로알킬기 및 C3~C40의 헤테로시클로알킬기로 이루어진 군에서 선택된다.A compound represented by the following formula (1):
[Formula 1]
Figure 112011095402950-pat00037

In Chemical Formula 1,
At least one of Ar 1 to Ar 4 is a substituent except hydrogen or deuterium;
When Ar 1 and Ar 4 are the same as each other, Ar 2 and Ar 3 are different substituents, and when Ar 1 and Ar 3 are the same as each other, Ar 2 and Ar 4 are different substituents;
Ar 1 to Ar 4 are the same as or different from each other, hydrogen, deuterium, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamino group, C 6 ~ C 40 diarylamino group, C 6 to C 40 arylalkyl group, C 3 to C 40 cycloalkyl group and C 3 to C 40 heterocycloalkyl group;
R 1 and R 2 are the same or different from each other, hydrogen, deuterium, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 of the aryl group, C 5 ~ C 40 heteroaryl group, C 6 ~ C 40 arylamino group, C 6 ~ C 40 diarylamino group, C 6 ~ C 40 arylalkyl group, C 3 ~ C 40 cycloalkyl group and C 3 ~ C 40 heterocycloalkyl group. 제1항에 있어서,
상기 R1 및 R2는 수소, C1~C40의 알킬기, C6~C40의 아릴기 및 C5~C40의 헤테로아릴기로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물.The method of claim 1,
R 1 and R 2 is hydrogen, C 1 ~ C 40 Alkyl group, C 6 ~ C 40 It is selected from the group consisting of aryl group and C 5 ~ C 40 heteroaryl group. 제2항에 있어서,
상기 Ar1 과 Ar4는 서로 같은 치환기이고, 상기 Ar2와 Ar3는 서로 다른 치환기인 것을 특징으로 하는 화합물.The method of claim 2,
Wherein Ar 1 and Ar 4 are the same substituents, and Ar 2 and Ar 3 are different substituents. 제2항에 있어서,
상기 Ar1 내지Ar4는 C1~C40의 알킬기, C6~C40의 아릴기 및 C5~C40의 헤테로아릴기로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물.The method of claim 2,
Ar 1 to Ar 4 is a compound, characterized in that selected from the group consisting of C 1 ~ C 40 Alkyl group, C 6 ~ C 40 aryl group and C 5 ~ C 40 heteroaryl group. 제1항에 있어서,
상기 R1 및 R2는 치환 또는 비치환된 메틸, i-프로필, t-부틸, 페닐, 바이페닐, 나프틸, 페난트렌, 9,9-디메틸-9H-플루오렌, 9,9-디페닐-9H-플루오렌 및 플루오란센으로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물.The method of claim 1,
R 1 and R 2 are substituted or unsubstituted methyl, i-propyl, t-butyl, phenyl, biphenyl, naphthyl, phenanthrene, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl -9H-fluorene and fluoranthene. 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서,
상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제5항 중 어느 한 항에 따른 화학식 1로 표시되는 화합물을 포함하는 유기물층인 것을 특징으로 하는 유기 전계 발광 소자.1. An organic electroluminescent device comprising an anode, a cathode, and at least one organic material layer interposed between the anode and the cathode,
At least one of the at least one organic material layer is an organic electroluminescent device, characterized in that the organic material layer containing a compound represented by the formula (1) according to any one of claims 1 to 5. 제6항에 있어서,
상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층인 것을 특징으로 하는 유기 전계 발광 소자.The method according to claim 6,
The organic material layer containing the compound represented by Formula 1 is an organic light emitting device, characterized in that the light emitting layer.
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