KR101713530B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents
An electroluminescent compound and an electroluminescent device comprising the same Download PDFInfo
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- KR101713530B1 KR101713530B1 KR1020140058786A KR20140058786A KR101713530B1 KR 101713530 B1 KR101713530 B1 KR 101713530B1 KR 1020140058786 A KR1020140058786 A KR 1020140058786A KR 20140058786 A KR20140058786 A KR 20140058786A KR 101713530 B1 KR101713530 B1 KR 101713530B1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 91
- 239000000126 substance Substances 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 29
- 239000011368 organic material Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000005751 substituted indanyl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 147
- 238000003786 synthesis reaction Methods 0.000 description 147
- 238000004519 manufacturing process Methods 0.000 description 105
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- 239000000463 material Substances 0.000 description 37
- 238000005160 1H NMR spectroscopy Methods 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 16
- 230000005525 hole transport Effects 0.000 description 14
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 12
- YMNJJMJHTXGFOR-UHFFFAOYSA-N n-(4-bromophenyl)-4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=C(C)C=C1 YMNJJMJHTXGFOR-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 238000002347 injection Methods 0.000 description 10
- 239000007924 injection Substances 0.000 description 10
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
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- 125000000753 cycloalkyl group Chemical group 0.000 description 7
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- 229940125904 compound 1 Drugs 0.000 description 6
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- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
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- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 4
- 229940126639 Compound 33 Drugs 0.000 description 4
- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 4
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- 125000005264 aryl amine group Chemical group 0.000 description 4
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- 230000000052 comparative effect Effects 0.000 description 4
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
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- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 3
- DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 3
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 3
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
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- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 3
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- 125000004104 aryloxy group Chemical group 0.000 description 3
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- 229940125900 compound 59 Drugs 0.000 description 3
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- 125000005549 heteroarylene group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- RPCBIEHUQSGPNA-UHFFFAOYSA-N (3,5-ditert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC(B(O)O)=CC(C(C)(C)C)=C1 RPCBIEHUQSGPNA-UHFFFAOYSA-N 0.000 description 2
- HVBHEPYJVAMWCY-UHFFFAOYSA-N 1,1-dimethylindene Chemical compound C1=CC=C2C(C)(C)C=CC2=C1 HVBHEPYJVAMWCY-UHFFFAOYSA-N 0.000 description 2
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- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 2
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- 239000010936 titanium Substances 0.000 description 1
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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- 150000003852 triazoles Chemical group 0.000 description 1
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- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
본 발명은 유기전계발광소자에 채용되는 유기발광 화합물에 관한 것으로서, 하기 [화학식 1]로 표시되는 것을 특징으로 하고, 이를 정공수송 가능층 또는 발광층 내의 인광 호스트 화합물로 채용하는 경우 구동전압, 휘도 및 장수명 등의 발광특성이 우수한 유기전계발광소자를 구현할 수 있다.
[화학식 1]
[화학식 2]
[Chemical Formula 1]
(2)
Description
본 발명은 유기발광 화합물에 관한 것으로서, 보다 구체적으로는 유기전계발광소자의 정공주입층 또는 정공수송층의 정공수송 재료로 채용되는 유기발광 화합물 및 이를 채용하여 장수명 및 발광 효율이 현저히 향상된 유기전계발광소자에 관한 것이다.BACKGROUND OF THE
유기전계발광소자는 투명 기판 위에도 소자를 형성할 수 있을 뿐 아니라, 플라즈마 디스플레이 패널(Plasma Display Panel)이나 무기 전계 발광(EL) 디스플레이에 비해 10 V 이하의 저전압 구동이 가능하고, 전력 소모가 비교적 적으며, 색감이 뛰어나다는 장점이 있고, 녹색, 청색, 적색의 3가지 색을 나타낼 수가 있어 최근에 차세대 디스플레이 소자로 많은 관심의 대상이 되고 있다.The organic electroluminescent device can not only form an element on a transparent substrate but also can operate at a low voltage of 10 V or less as compared with a plasma display panel (Plasma Display Panel) or an inorganic electroluminescence (EL) display, It has the advantage of excellent color and has three colors of green, blue, and red. It has recently become a subject of interest as a next generation display device.
다만, 이러한 유기전계발광소자가 상기와 같은 특징으로 발휘하기 위해서는 소자 내 유기층을 이루는 물질인 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하나, 아직까지는 안정하고 효율적인 유기 전계발광 소자자용 유기물층 재료의 개발이 충분히 이루어지지 않은 상태이다. 따라서, 저전압 구동, 고효율 및 장수명을 갖는 새로운 재료의 개발이 계속 요구되고 있는 실정이다.However, in order for such an organic electroluminescent device to exhibit such characteristics, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material, which are materials forming an organic layer in a device, However, until now, stable and efficient development of an organic layer material for an organic electroluminescence element has not been sufficiently developed yet. Therefore, there is a continuing demand for development of new materials having low-voltage driving, high efficiency and long life.
특히, 종래 정공수송 재료로 구리프탈로시아닌(CuPc), MTDATA, 4,4'-비스[N-(1-나프틸)-N-페닐아미노]바이페닐(NPB), N,N'-다이페닐-N,N'-비스(3-메틸페닐)-(1,1'-바이페닐)-4,4'-다이아민(TPD) 등이 알려져 있으나, 이를 소자에 채용시 효율 및 수명이 저하되는 문제가 있고, 이를 개량하기 위하여 다양한 치환기를 갖는 아릴아민계 화합물에 대해서 개발되고 있으나, 여전히 효율과 장수명을 동시에 충족시키기에는 충분하지 않은 문제점을 갖고 있다.In particular, conventional hole transport materials include copper phthalocyanine (CuPc), MTDATA, 4,4'-bis [N- (1-naphthyl) -N- phenylamino] biphenyl (NPB), N, N, N'-bis (3-methylphenyl) - (1,1'-biphenyl) -4,4'-diamine (TPD) has been known. However, Based compound having various substituents in order to improve it, but it still has a problem that it is not enough to satisfy efficiency and long life at the same time.
따라서, 본 발명은 종래의 정공수송 재료 대비 발광 효율 및 수명 특성이 현저히 향상된 유기발광 화합물 및 이를 채용하여 발광 효율과 수명 특성이 우수한 유기전계발광소자를 제공하고자 한다.Accordingly, it is an object of the present invention to provide an organic light emitting compound having remarkably improved light emission efficiency and lifetime characteristics compared to conventional hole transport materials, and an organic electroluminescent device having excellent light emitting efficiency and lifetime characteristics by employing the same.
본 발명은 상기 과제를 해결하기 위하여, 하기 [화학식 1] 내지 [화학식 2]로 표시되는 유기발광 화합물 및 이를 포함하는 유기전계발광소자를 제공한다.The present invention provides an organic light emitting compound represented by the following
[화학식 1][Chemical Formula 1]
[화학식 2](2)
상기 [화학식 1] 내지 [화학식 2]의 치환기에 대한 구체적인 설명은 후술하기로 한다.Specific examples of the substituents of the above formulas (1) to (2) will be described later.
본 발명에 따른 유기발광 화합물은 종래 정공수송 화합물에 비하여 보다 향상된 발광 효율과 장수명 특성의 구현이 가능하여 이를 채용한 유기전계발광소자는 다양한 디스플레이 소자에 유용하게 사용될 수 있다.The organic electroluminescent device according to the present invention can realize more improved luminous efficiency and long life characteristics than the conventional hole transporting compound, and thus the organic electroluminescent device employing the organic electroluminescent device can be used for various display devices.
도 1 내지 5는 본 발명의 일 실시예에 따른 유기전계발광소자의 구조를 예시한 단면도이다.1 to 5 are cross-sectional views illustrating the structure of an organic electroluminescent device according to an embodiment of the present invention.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명의 하기 [화학식 1] 내지 [화학식 2]로 표시되는 유기발광 화합물에 관한 것이다.The present invention relates to an organic light-emitting compound represented by the following formulas (1) to (2).
[화학식 1][Chemical Formula 1]
[화학식 2](2)
상기 [화학식 1] 내지 [화학식 2]에서,In the above
L1 내지 L3는 서로 동일하거나 상이하고, 각각 독립적으로 단일결합이거나, 치환 또는 비치환된 탄소수 1 내지 30의 알킬렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알케닐렌기, 치환 또는 비치환된 탄소수 2 내지 30의 알키닐렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬렌기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기, N, O, P 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 5 내지 50의 아릴렌기 및 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합되고, N, O, P 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴렌기 중에서 선택된다.L 1 to L 3 are the same or different and each independently represents a single bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted group having 2 to 30 carbon atoms A substituted or unsubstituted C2-C30 alkynylene group, a substituted or unsubstituted C3-C30 A substituted or unsubstituted arylene group having 5 to 50 carbon atoms, a substituted or unsubstituted C2 to C50 heteroarylene group containing at least one of N, O, P and S atoms, a substituted or unsubstituted C6- Substituted or unsubstituted C 5 -C 50 arylene group and substituted or unsubstituted C 3 -C 30 cycloalkyl wherein at least one of the substituted or unsubstituted C 3 -C 30 cycloalkyl is fused with at least one of N, And a substituted or unsubstituted heteroarylene group having 2 to 50 carbon atoms containing at least one of S atoms.
m, n 및 o는 각각 독립적으로 0 내지 4의 정수이고, 상기 m, n 및 o가 2 이상인 경우 복수의 L1 내지 L3는 서로 및 각각 동일하거나 상이할 수 있다.m, n and o are each independently an integer of 0 to 4, and when m, n and o are two or more, plural L 1 to L 3 may be the same or different from each other.
Y1 내지 Y4는 각각 독립적으로 CH 또는 N이고, 상기 Y1 내지 Y4 중 하나 이상은 *-(L1)n-[A]p로 치환되어 결합되어 있다.Y 1 to Y 4 are each independently CH or N, and at least one of Y 1 to Y 4 is substituted with * - (L 1 ) n - [A] p .
a 및 b는 각각 독립적으로 0 내지 4의 정수이고, 상기 a 및 b가 각각 2 이상인 경우 복수의 *-[ ]은 서로 동일하거나 상이할 수 있다.a and b are each independently an integer of 0 to 4, and when a and b are each 2 or more, a plurality of * - [] may be the same or different from each other.
X는 N 또는 CR1R2이고, 상기 R1 및 R2는 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 아릴기 또는 N, O, P 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 헤테로아릴기일 수 있다.
X is N or CR 1 R 2 and wherein R 1 And R 2 are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group containing at least one of N, O, P and S atoms .
[A], [B] 및 [C]는 각각 하기 [구조식 1]로 표시되고, p, q 및 r은 각각 독립적으로 0 내지 3의 정수이고, 상기 p, q 및 r이 2 이상인 경우 복수의 [A], [B] 및 [C]는 서로 및 각각 동일하거나 상이할 수 있다.[A], [B] and [C] are each represented by the following
[구조식 1][Structural formula 1]
상기 [구조식 1]에서,In the
Ar1 및 Ar2는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬기, 치환 또는 비치환된 탄소수 5 내지 50의 아릴기, N, O, P 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기, 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합된 치환 또는 비치환된 탄소수 5 내지 50의 아릴기 및 치환 또는 비치환된 탄소수 3 내지 30의 시클로알킬이 하나 이상 융합되고, N, O, P 및 S 원자 중 1개 이상을 포함하는 치환 또는 비치환된 탄소수 2 내지 50의 헤테로아릴기 중에서 선택된다.Ar 1 and Ar 2 are the same or different and each independently represents a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted group having 5 to 50 carbon atoms A substituted or unsubstituted C2 to C50 heteroaryl group containing at least one of N, O, P and S atoms, a substituted or unsubstituted C3 to C30 cycloalkyl, Or a substituted or unsubstituted aryl group having 5 to 50 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms and having at least one of N, O, P and S atoms, And a heteroaryl group having 2 to 50 carbon atoms.
또한, 상기 L1 내지 L3, Ar1 내지 Ar2, R1 및 R2가 치환기로 더 치환되는 경우, 상기 치환기는 중수소, 시아노기, 할로겐기, 니트로기, 탄소수 1 내지 20의 알킬기, 탄소수 6 내지 30의 아릴기, 탄소수 5 내지 30의 헤테로아릴기, 탄소수 1 내지 20의 알킬아미노기, 탄소수 6 내지 30의 아릴아미노기, 탄소수 1 내지 20의 알콕시기, 탄소수 6 내지 30의 아릴옥시기. 탄소수 3 내지 20의 시클로알킬기 및 탄소수 6 내지 30의 아릴싸이오기, 탄소수 1 내지 20의 알케닐기, 탄소수 1 내지 20의 알킬실릴기 및 탄소수 6 내지 30의 아릴실릴기 중에서 선택되는 1종 이상이고, 상기 치환기는 인접한 치환기와 결합하여 포화 또는 불포화 고리를 형성할 수 있다.
The above-mentioned L 1 to L 3 , Ar 1 To Ar 2, R 1 and R 2 is the case is further substituted with a substituent, the substituent is heavy hydrogen, a cyano group, a halogen group, an aryl group, a nitro group, an alkyl group having 1 to 20 carbon atoms, having 6 to 30 carbon atoms, having 5 to 30 carbon atoms An alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 30 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms. At least one selected from the group consisting of a cycloalkyl group having 3 to 20 carbon atoms and an arylthio group having 6 to 30 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, and an arylsilyl group having 6 to 30 carbon atoms, The substituent may be bonded to an adjacent substituent to form a saturated or unsaturated ring.
본 발명에 있어서, 상기 치환기들의 예시들에 대해서 아래에서 구체적으로 설명하나, 이에 한정되는 것은 아니다.In the present invention, examples of the substituents will be specifically described below, but the present invention is not limited thereto.
본 발명에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥틸메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 2-메틸펜틸기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이들에 한정되지 않는다.In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, Ethyl, propyl, isopropyl, n-butyl, isobutyl, isobutyl, isobutyl, A tert-butyl group, a tert-butyl group, a 2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, Ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , Isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group and the like, but are not limited thereto.
본 발명에 있어서, 알콕시기는 직쇄 또는 분지쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 입체적 방해를 주지 않는 범위인 1 내지 30개인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, i-프로필옥시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be linear or branched. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably in the range of 1 to 30, which does not cause steric hindrance. Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an i-propyloxy group, a n-butoxy group, an isobutoxy group, a tert- , Neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n- , A benzyloxy group, a p-methylbenzyloxy group, and the like, but are not limited thereto.
본 발명에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 구체적인 예로는 비닐기, 1-프로페닐기, 이소프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 3-메틸-1-부테닐기, 1,3-부타디에닐기, 알릴기, 1-페닐비닐-1-일기, 2-페닐비닐-1-일기, 2,2-디페닐비닐-1-일기, 2-페닐-2-(나프틸-1-일)비닐-1-일기, 2,2-비스(디페닐-1-일)비닐-1-일기, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present invention, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-yl group, But are not limited to, - (naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like.
본 발명에 있어서, 아릴기는 단환식 또는 다환식일 수 있고, 탄소수는 특별히 한정되지 않으나 6 내지 60인 것이 바람직하다. 단환식 아릴기의 예로는 페닐기, 비페닐기, 터페닐기, 스틸벤기 등이 있고, 다환식 아릴기의 예로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 테트라세닐기, 크라이세닐기, 플루오레닐기, 아세나프타센닐기, 트리페닐렌기, 플루오안트렌(fluoranthrene)기 등이 있으나, 본 발명의 범위가 이들 예로만 한정되는 것은 아니다.In the present invention, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group and a stilbene group. Examples of the polycyclic aryl group include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, , A chlorenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluororanthrene group, but the scope of the present invention is not limited to these examples.
본 발명에 있어서, 헤테로아릴기는 이종원자로 O, N 또는 S를 포함하는 헤테로고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤조옥사졸기, 벤조이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난트롤린기, 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, the heteroaryl group is a hetero ring group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a dibenzofurancyl group, a phenanthroline group, An isothiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group and the like, but is not limited thereto.
본 발명에 있어서, 아릴옥시기, 아릴티옥시기, 아릴술폭시기 및 아랄킬아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 구체적으로 아릴옥시기로는 페녹시기, p-토릴옥시기, m-토릴옥시기, 3,5-디메틸-페녹시기, 2,4,6-트리메틸페녹시기, ptert-부틸페녹시기, 3-비페닐옥시기, 4-비페닐옥시기, 1-나프틸옥시기, 2-나프틸옥시기, 4-메틸-1-나프틸옥시기, 5-메틸-2-나프틸옥시기, 1-안트릴옥시기, 2-안트릴옥시기, 9-안트릴옥시기, 1-페난트릴옥시기, 3-페난트릴옥시기, 9-페난트릴옥시기 등이 있고, 아릴티옥시기로는 페닐티옥시기기, 2－메틸페닐티옥시기, 4－tert－부틸페닐티옥시기 등이 있으며, 아릴술폭시기로는 벤젠술폭시기, p－톨루엔술폭시기 등이 있으나, 이에 한정되지 않는다.In the present invention, the aryl group in the aryloxy group, arylthioxy group, arylsulfoxy group and aralkylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a ptert- Anthryloxy group, 2-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, Anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group and the like. Examples of the arylthioxy group include phenylthioxy group, 2- A 4-tert-butylphenyloxy group, and the like. Examples of the arylsulfoxy group include benzene sulfoxy group and p-toluenesulfoxy group. However, the present invention is not limited thereto.
본 발명에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 구체적으로 시클로프로필기 시클로부틸기 시클로펜틸기 3-메틸시클로펜틸기 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다.In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, Methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclo An octyl group, and the like, but are not limited thereto.
본 발명에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present invention, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 발명에 있어서, 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 치환 또는 비치환된 디아릴아민기, 또는 치환 또는 비치환된 트리아릴아민기가 있다. 상기 아릴아민기 중의 아릴기는 단환식 아릴기일 수 있고, 다환식 아릴기일 수 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식아릴기와 다환식 아릴기를 동시에 포함할 수 있다.In the present invention, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
상기 아릴아민기의 구체적인 예로는 페닐아민기, 나프틸아민기, 비페닐아민기, 안트라세닐아민기, 3-메틸-페닐아민기, 4-메틸-나프틸아민기, 2-메틸-비페닐아민기, 9-메틸-안트라세닐아민기, 디페닐 아민기, 페닐 나프틸 아민기, 디톨릴 아민기, 페닐 톨릴 아민기, 카바졸기 및 트리페닐 아민기 등이 있으나, 이에 한정되는 것은 아니다.Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, But are not limited to, an amine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a carbazole group and a triphenylamine group.
본 발명에 있어서, 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다.In the present invention, the silyl group is specifically exemplified by trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, But are not limited thereto.
본 발명에 있어서, 헤테로아릴아민기 중의 헤테로 아릴기는 전술한 헤테로고리기의 예시 중에서 선택될 수 있다.In the present invention, the heteroaryl group in the heteroarylamine group can be selected from the examples of the above-mentioned heterocyclic group.
본 발명에 있어서, 알킬티옥시기, 알킬술폭시기 중의 알킬기는 전술한 알킬기의 예시와 같다. 구체적으로 알킬티옥시기로는 메틸티옥시기, 에틸티옥시기, tert－부틸티옥시기, 헥실티옥시기, 옥틸티옥시기 등이 있고, 알킬술폭시기로는 메실, 에틸술폭시기, 프로필술폭시기, 부틸술폭시기 등이 있으나, 이에 한정되지 않는다.In the present invention, the alkyloxy group in the alkylthio group and the alkyl group in the alkylsulfoxy group are the same as the aforementioned alkyl groups. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, But are not limited thereto.
본 발명에 있어서, 치환된 아릴렌기라 함은, 페닐기, 비페닐기, 나프탈렌기, 플루오레닐기, 파이레닐기, 페난트레닐기, 페릴렌기, 테트라세닐기. 안트라센닐기 등이 다른 치환기로 치환된 것을 의미한다.In the present invention, the substituted arylene group means a phenyl group, a biphenyl group, a naphthalene group, a fluorenyl group, a pyrenyl group, a phenanthrenyl group, a perylene group, a tetracenyl group. Anthracenyl group and the like are substituted with other substituents.
본 발명에 있어서, 치환된 헤테로아릴렌기라 함은, 피리딜기, 티오페닐기, 트리아진기, 퀴놀린기, 페난트롤린기, 이미다졸기, 티아졸기, 옥사졸기, 카바졸기 및 이들의 축합헤테로고리기, 예컨대 벤즈퀴놀린기, 벤즈이미다졸기, 벤즈옥사졸기, 벤즈티아졸기, 벤즈카바졸기, 디벤조티오페닐기, 디벤조퓨란기 등이 다른 치환기로 치환된 것을 의미한다.
In the present invention, the substituted heteroarylene group includes a pyridyl group, a thiophenyl group, a triazine group, a quinoline group, a phenanthroline group, an imidazole group, a thiazole group, an oxazole group, a carbazole group and condensed heterocyclic groups, Such as a benzoquinoline group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzzcarbazole group, a dibenzothiophenyl group, a dibenzofurane group and the like are substituted with other substituents.
상기 [화학식 1] 내지 [화학식 2]로 표시되는 본 발명에 따른 유기발광 화합물은 그 구조적 특이성으로 인하여 유기전계발광소자의 유기물층으로 사용될 수 있고, 보다 구체적으로 유기물층 내 정공수송 재료로 사용될 수 있다.The organic luminescent compound according to the present invention represented by the above
본 발명에 따른 [화학식 1]로 표시되는 화합물의 바람직한 구체예로는 하기 화합물들이 있으나, 이들에만 한정되는 것은 아니다.Preferred examples of the compound represented by the formula (1) according to the present invention include, but are not limited to, the following compounds.
상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 도입된 치환기의 고유 특성을 갖는 유기발광 화합물을 합성할 수 있다. 예컨대, 유기전계발광소자의 제조시 사용되는 정공 주입층 물질, 정공 수송층 물질, 발광층 물질 및 전자 수송층 물질에 사용되는 치환기를 상기 구조에 도입함으로써 각 유기물층에서 요구하는 조건들을 충족시키는 물질을 제조할 수 있으며, 특히 본 발명에 따른 [화학식 1] 내지 [화학식 2]의 화합물은 정공 주입층 또는 정공 수송층 물질로 적용할 경우 소자의 발광효율 및 수명 특성을 더욱 향상시킬 수 있다.
An organic luminescent compound having the intrinsic characteristics of the substituent introduced by introducing various substituents into the core structure having the above structure can be synthesized. For example, by introducing a substituent used in a hole injection layer material, a hole transport layer material, a light emitting layer material, and an electron transport layer material used in the production of an organic electroluminescent device into the structure, a material meeting the requirements of each organic layer can be manufactured In particular, the compounds of the formulas (1) to (2) according to the present invention can improve the luminous efficiency and lifetime characteristics of the device when applied as a hole injection layer or a hole transport layer material.
본 발명의 화합물은 유기전계발광소자의 통상의 제조방법에 따라 소자에 적용할 수 있다.The compound of the present invention can be applied to a device according to a conventional method of manufacturing an organic electroluminescent device.
본 발명의 하나의 실시예에 따른 유기전계발광소자는 제1 전극과 제2 전극 및 이 사이에 배치된 유기물층을 포함하는 구조로 이루어질 수 있으며, 본 발명에 따른 유기발광 화합물을 소자의 유기물층에 사용한다는 것을 제외하고는 통상의 소자의 제조 방법 및 재료를 사용하여 제조될 수 있다.
The organic electroluminescent device according to one embodiment of the present invention may have a structure including a first electrode, a second electrode and an organic material layer disposed therebetween, and the organic electroluminescent compound according to the present invention may be used for an organic material layer And can be manufactured using conventional device manufacturing methods and materials.
본 발명에 따른 유기전계발광소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등을 포함하는 구조를 가질 수 있다. 그러나, 이에 한정되지 않고 더 적은 수의 유기물층을 포함할 수도 있다.The organic material layer of the organic electroluminescent device according to the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. However, it is not limited to this and may include a smaller number of organic layers.
따라서, 본 발명에 따른 유기전계발광소자에서, 상기 유기물층은 정공 주입층, 정공 수송층, 및 정공 주입 및 정공 수송을 동시에 하는 층 중 1층 이상을 포함할 수 있고, 상기 층들 중 1층 이상이 상기 [화학식 1] 또는 [화학식 2]로 표시되는 화합물을 포함할 수 있다.
Therefore, in the organic electroluminescent device according to the present invention, the organic material layer may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, May include a compound represented by formula (1) or (2).
예컨대, 본 발명에 따른 유기 전자 소자의 구조는 도 1 내지 5에 예시되어 있다.For example, the structure of an organic electronic device according to the present invention is illustrated in Figs.
도 1에는 기판(1) 위에 양극(2), 정공 주입층(3), 정공 수송층(4), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1] 또는 [화학식 2]로 표시되는 화합물은 상기 정공 주입층(3), 정공 수송층(4), 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.1 shows an
도 2에는 기판(1) 위에 양극(2), 정공 주입층(3), 정공 수송층(4), 발광층(5) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1] 또는 [화학식 2]로 표시되는 화합물은 상기 정공 주입층(3), 정공 수송층(4) 또는 전자 수송층(6)에 포함될 수 있다.2 shows a structure of an organic electroluminescent device in which an
도 3에는 기판(1) 위에 양극(2), 정공 수송층(4), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1] 또는 [화학식 2]로 표시되는 화합물은 상기 정공 수송층(4), 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.3 illustrates the structure of an organic electroluminescent device in which an
도 4에는 기판(1) 위에 양극(2), 발광층(5), 전자 수송층(6) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1] 또는 [화학식 2]로 표시되는 화합물은 상기 발광층(5) 또는 전자 수송층(6)에 포함될 수 있다.4 shows the structure of an organic electroluminescent device in which an
도 5에는 기판(1) 위에 양극(2), 발광층(5) 및 음극(7)이 순차적으로 적층된 유기전계발광소자의 구조가 예시되어 있다. 이와 같은 구조에 있어서, 상기 [화학식 1] 또는 [화학식 2]로 표시되는 화합물은 상기 발광층(5)에 포함될 수 있다.5 illustrates the structure of an organic electroluminescent device in which an
본 발명의 바람직한 구현예에 의하면, 상기 [화학식 1] 또는 [화학식 2]로 표시되는 화합물은 상기 정공 주입층(3) 또는 정공 수송층(4)에 포함될 수 있다.
According to a preferred embodiment of the present invention, the compound represented by
예컨대, 본 발명에 따른 유기전계발광소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층, 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다.For example, the organic electroluminescent device according to the present invention can be manufactured by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal oxide or a conductive metal oxide on the substrate, An anode is formed by depositing an alloy on the anode, and an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and then a substance usable as a cathode is deposited thereon.
이와 같은 방법 외에도, 기판 상에 음극 물질부터 유기물층, 양극 물질을 차례로 증착시켜 유기전계발광소자를 만들 수도 있다. 상기 유기물층은 정공 주입층, 정공 수송층, 발광층 및 전자 수송층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 솔벤트 프로세스(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.In addition to such a method, an organic electroluminescent device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate. The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the organic material layer may be formed using a variety of polymer materials by a solvent process such as a spin coating process, a dip coating process, a doctor blading process, a screen printing process, an inkjet printing process or a thermal transfer process, Layer.
상기 양극 물질로는 통상 유기물층으로 정공주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금, 아연 산화물, 인듐 산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물, ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) metal oxides, ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT) , Conductive polymers such as polypyrrole and polyaniline, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금, LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or an alloy thereof; a multilayer such as LiF / Al or LiO 2 / Structural materials, and the like, but are not limited thereto.
정공 주입 물질로는 낮은 전압에서 양극으로부터 정공을 잘 주입받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴 헥사아자트리페닐렌, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene, quinacridone-based organic materials, perylene-based organic materials, Anthraquinone, polyaniline and a polythiophene-based conductive polymer, but are not limited thereto.
정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송 받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다.As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility to holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3), 카르바졸 계열 화합물, 이량체화 스티릴(dimerized styryl) 화합물, BAlq, 10-히드록시벤조 퀴놀린-금속 화합물, 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물, 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자, 스피로(spiro) 화합물, 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ), carbazol-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzthiazole and A benzimidazole-based compound, a poly (p-phenylene vinylene) (PPV) -based polymer, a spiro compound, polyfluorene, rubrene, and the like.
전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다.As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is highly mobile, is suitable. Specific examples thereof include, but are not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
본 발명에 따른 유기전계발광소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
또한, 본 발명에 따른 유기발광 화합물은 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기전계발광소자에 적용되는 것과 유사한 원리로 작용할 수 있다.
In addition, the organic electroluminescent compound according to the present invention can act on a principle similar to that applied to an organic electroluminescent device in an organic electronic device including an organic solar cell, an organophotoreceptor, an organic transistor and the like.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시한다. 그러나, 하기의 실시예는 본 발명을 예시하기 위한 것이며, 이에 의하여 본 발명의 범위가 한정되는 것은 아니다.
Hereinafter, preferred embodiments of the present invention will be described in order to facilitate understanding of the present invention. However, the following examples are intended to illustrate the invention and are not intended to limit the scope of the invention.
실시예Example
1 : 화합물 1의 합성 1: Synthesis of
(1) (One) 제조예Manufacturing example 1 : 중간체 1-1의 합성 1: Synthesis of intermediate 1-1
3-bromo-1H-indole(5.0 g, 0.026 mol)에 9H-carbazol-3-ylboronic acid(6.5 g, 0.030 mol), Pd(pph3)4(1.5 g, 0.0013 mol), potassium carbonate(7.2 g, 0.052 mol)에 THF 200 mL를 넣고 65 ℃에서 18시간 교반하여 반응시켰다. 반응종료 후 냉각하여 H20 : MC에 층분리 후 컬럼정제(n-Hexane :MC)하여 중간체 1-1을 5.2 g(71%)수득하였다.(m/z=282)
3-ylboronic acid (6.5 g, 0.030 mol), Pd (PPh 3 ) 4 (1.5 g, 0.0013 mol) and potassium carbonate (7.2 g, 0.026 mol) were added to 3-bromo- , 0.052 mol) was added 200 mL of THF, and the mixture was reacted at 65 DEG C for 18 hours with stirring. After completion of the reaction, the reaction mixture was cooled, separated into H 2 O: MC and subjected to column purification (n-hexane: MC) to obtain 5.2 g (71%) of Intermediate 1-1 (m / z = 282)
(2) (2)
제조예Manufacturing example
2 : 화합물 1의 합성 2: Synthesis of
중간체 1-1(5.0 g, 0.018 mol), 4-bromo-N,N-dip-tolylaniline(12.5 g, 0.036 mol), Pd(dba)2(0.8 g, 0.0009 mol), sodium-tert-butoxide(3.5 g, 0.052 mol)에 TOL 200 mL를 넣고 95 ℃에서 4시간 교반하여 반응시켰다. 반응종료 후H20 :MC에 층분리 후 컬럼정제 (n-HEXANE : MC)하여 화합물 1을 11.2 g (75%)수득하였다.To a solution of intermediate 1-1 (5.0 g, 0.018 mol), 4-bromo-N, N-dip-tolylaniline (12.5 g, 0.036 mol), Pd (dba) 2 (0.8 g, 0.0009 mol) 3.5 g, 0.052 mol) was added 200 mL of TOL, and the mixture was reacted at 95 DEG C for 4 hours with stirring. After completion of the reaction, the reaction mixture was separated into H 2 O: MC and column-purified (n-HEXANE: MC) to obtain 11.2 g (75%) of
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.55/d, 8.17/d, 7.94/d, 7.87/d, 7.77/s, 7.71/d, 7.69/d, 7.36/s, 7.33/m, 7.25/m) 2H(7.42/m) 4H(7.37/d, 6.63/d, 2.34/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.55 / d, 8.17 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.71 / d, 7.69 / d, 7.36 / s, 7.33 / m , 7.25 / m) 2H (7.42 / m) 4H (7.37 / d, 6.63 / d, 2.34 /
LC/MS: m/z= 826[(M+1)+]
LC / MS: m / z = 826 [(M + 1) < + &
실시예Example
2 : 화합물 2의 합성 2: Synthesis of
(1) (One) 제조예Manufacturing example 1 : 중간체 2-1의 합성 1: Synthesis of intermediate 2-1
3-bromo-1H-indole(5.0 g, 0.026 mol)에 1H-indol-3-ylboronic acid(4.8 g, 0.030 mol)를 넣고 실시예 1-제조예(1)에서 사용된 동일한 방법으로 합성하여 <중간체 2-1> 4.6g (수율 77%)을 얻었다.(m/z=232)
3-ylboronic acid (4.8 g, 0.030 mol) was added to 3-bromo-1H-indole (5.0 g, 0.026 mol) To obtain 4.6 g (yield 77%) of Intermediate 2-1 (m / z = 232)
(2) (2)
제조예Manufacturing example
2 : 화합물 2의 합성 2: Synthesis of
중간체 2-1(5.0 g, 0.022 mol)에 4-bromo-N,N-dip-tolylaniline(15.2 g, 0.044 mol)를 넣고 실시예 1-제조예(2)에서 사용된 동일한 방법으로 합성하여 <화합물 2> 12.4 g (수율 73%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (2) except that 4-bromo-N, N-dip-tolylaniline (15.2 g, 0.044 mol) was added to Intermediate 2-1 (5.0 g, 0.022 mol)
H-NMR (200MHz, CDCl3):δ ppm, 2H(8.55/d, 7.94/d, 7.60/s, 7.33/m, 7.25/m) 4H(7.37/d, 6.63/d, 2.34/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 2H (8.55 / d, 7.94 / d, 7.60 / s, 7.33 / m, 7.25 / m) 4H (7.37 / d, 6.63 / d, 2.34 / s) 8H (6.98 / d, 6.51 / d)
LC/MS: m/z=775 [(M+1)+]
LC / MS: m / z = 775 [(M + 1) < + &
실시예Example
3 : 화합물 3의 합성 3: Synthesis of
(1) (One) 제조예Manufacturing example 1 : 중간체 3-1의 합성 1: Synthesis of intermediate 3-1
5-bromo-1H-indole(5.0 g, 0.026 mol)에 1H-indol-5-ylboronic acid(4.8 g, 0.030 mol)를 넣고 실시예 1-제조예(1)에서 사용된 동일한 방법으로 합성하여 <중간체 3-1> 4.2 g (수율 70%)을 얻었다.(m/z=232)
5-ylboronic acid (4.8 g, 0.030 mol) was added to 5-bromo-1H-indole (5.0 g, 0.026 mol) 4.2 g (yield 70%) of intermediate 3-1 (m / z = 232)
(2) (2)
제조예Manufacturing example
2 : 화합물 3의 합성 2: Synthesis of
중간체 3-1(5.0 g, 0.022 mol)에 4-bromo-N,N-dip-tolylaniline(15.2 g, 0.044 mol)를 넣고 실시예 1-제조예(2)에서 사용된 동일한 방법으로 합성하여 <중간체 3-2> 12.4 g (수율 73%)을 얻었다.Was synthesized in the same manner as in Example 1 (2) except that 4-bromo-N, N-dip-tolylaniline (15.2 g, 0.044 mol) was added to Intermediate 3-1 (5.0 g, 0.022 mol) Intermediate 3-2> 12.4 g (yield: 73%) was obtained.
H-NMR (200MHz, CDCl3):δ ppm, 2H(8.18/d, 8.00/d, 7.77/s, 7.60/d, 6.52/d) 4H(7.37/d, 6.63/d, 2.34/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 2H (8.18 / d, 8.00 / d, 7.77 / s, 7.60 / d, 6.52 / d) 4H (7.37 / d, 6.63 / d, 2.34 / s) 8H (6.98 / d, 6.51 / d)
LC/MS: m/z=775 [(M+1)+]
LC / MS: m / z = 775 [(M + 1) < + &
실시예Example 4 : 화합물 11의 합성 4: Synthesis of Compound 11
(1) (One) 제조예Manufacturing example 1 : 중간체 4-1의 합성 1: Synthesis of Intermediate 4-1
1H-indol-3-ylboronic acid(2.0 g, 0.012 mol)에 1-bromo-4-iodobenzene(2.8 g, 0.010 mol)를 넣고 실시예 1-제조예(1)에서 사용된 동일한 방법으로 합성하여 <중간체 4-1> 1.9 g (수율 71%)을 얻었다.(m/z=272)
4-iodobenzene (2.8 g, 0.010 mol) was added to 1H-indol-3-ylboronic acid (2.0 g, 0.012 mol) Intermediate 4-1> 1.9 g (yield: 71%) was obtained. (M / z = 272)
(2) (2) 제조예Manufacturing example 2 : 중간체 4-2의 합성 2: Synthesis of intermediate 4-2
중간체 4-1(5.0 g, 0.018 mol)에 1,4-dibromobenzene(4.2 g, 0.018 mol)를 넣고 실시예 1-제조예(2)에서 사용된 동일한 방법으로 합성하여 <중간체 4-2> 5.7 g (수율 74%)을 얻었다.(m/z=427)
Intermediate 4-2 was synthesized by the same method as in Preparation Example (2) of Example 1, except that 1,4-dibromobenzene (4.2 g, 0.018 mol) was added to Intermediate 4-1 (5.0 g, 0.018 mol) g (yield: 74%). (m / z = 427)
(3) (3) 제조예Manufacturing example 3 : 중간체 4-3의 합성 3: Synthesis of intermediate 4-3
1,1-dimethyl-1H-indene(3.0 g, 0.020 mol)에 N-bromosuccinimide(3.6 g, 0.020 mol)에 DMF 100 mL를 넣고 20 ℃에서 8시간 교반하여 반응시켰다. 반응 종료 후 H20 : 아세트산에틸로 층분리 후 컬럼정제(n-Hexane : MC)하여 중간체 4-3을2.1 g(48%)수득하였다.(m/z=223)
100 mL of DMF was added to N-bromosuccinimide (3.6 g, 0.020 mol) in 1,1-dimethyl-1H-indene (3.0 g, 0.020 mol) and the mixture was reacted at 20 ° C for 8 hours with stirring. After completion of the reaction H 2 0: column purification after separating layer with ethyl acetate: the intermediate 4-3 (n-Hexane MC) to afford 2.1 g (48%) (m / z = 223).
(4) (4) 제조예Manufacturing example 4 : 중간체 4-4의 합성 4: Synthesis of intermediate 4-4
p-toluidine(2.0 g, 0.019 mol)에 중간체 4-3(4.2 g, 0.019 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 4-4> 3.5 g (수율 74%)을 얻었다.(m/z=249)
Synthesis was conducted in the same manner as in Example 1 (2), except that Intermediate 4-3 (4.2 g, 0.019 mol) was added to p-toluidine (2.0 g, 0.019 mol) Yield: 74%). (M / z = 249)
(5) (5) 제조예Manufacturing example 5 : 화합물 11의 합성 5: Synthesis of Compound 11
중간체 4-2(5.0 g, 0.012 mol)에 중간체 4-4(6.0 g, 0.024 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 11> 6.6 g (수율 72%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (2) to obtain Intermediate 4-4 (6.0 g, 0.024 mol) and Intermediate 4-2 (5.0 g, 0.012 mol) 72%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.17/d, 7.71/d, 7.36/s) 2H(7.54/d, 7.42/m, 7.37/d, 7.30/d, 7.22/m, 6.69/d, 6.63/d, 6.05/d, 2.34/s) 4H(7.25/m, 6.98/d, 6.51/d, 1.69/s) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.17 / d, 7.71 / d, 7.36 / s) 2H (7.54 / d, 7.42 / m, 7.37 / d, 7.30 / d, 7.22 / m, 6.69 d, 6.63 d, 6.05 d, 2.34 s) 4H (7.25 m, 6.98 d, 6.51 d, 1.69 s)
LC/MS: m/z= 765[(M+1)+]
LC / MS: m / z = 765 [(M + 1) < + &
실시예Example
5 : 화합물 5의 합성 5: Synthesis of
(1) (One) 제조예Manufacturing example 1 : 중간체 5-1의 합성 1: Synthesis of intermediate 5-1
3-bromo-1H-indole(5.0 g, 0.026 mol)에 4-bromo-N,N-dip-tolylaniline(9.2 g, 0.026 mol)를 넣고 실시예 1-제조예(2)에서 사용된 동일한 방법으로 합성하여 <중간체 5-1> 8.6 g (수율 71%)을 얻었다.(m/z=467)
The same procedure as in Example 1-Preparation Example (2) was repeated except that 4-bromo-N, N-dip-tolylaniline (9.2 g, 0.026 mol) was added to 3-bromo-1H- indole (5.0 g, To obtain 8.6 g (yield 71%) of Intermediate 5-1 (m / z = 467)
(2) (2) 제조예Manufacturing example 2 : 중간체 5-2의 합성 2: Synthesis of Intermediate 5-2
1,4-dibromobenzene(3.0 g, 0.013 mol)에 N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(4.7 g, 0.013 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 5-2> 4.7 g(수율 70%)을 얻었다.(m/z=516)
(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (4.7 g, 0.013 mol) was added to 1,4-dibromobenzene (3.0 g, 0.013 mol) (M / z = 516) (Intermediate 5-2) (4.7 g, yield 70%) was obtained by the same method as in Example (2)
(3) (3) 제조예Manufacturing example 3 : 중간체 5-2'의 합성 3: Synthesis of intermediate 5-2 '
중간체 5-2(5.0 g, 0.010 mol), bis(pinacolato)dibron(3.0 g, 0.012 mol), PdCl2(dppf)(0.4 g, 0.005 mol), potassium-acetate(2.8 g, 0.020 mol)에 1,4-dioxane 100 mL를 넣고 95 ℃에서 24시간 교반하여 반응시켰다.반응 종료 후 냉각하여 H20 : MC에 층분리 후 컬럼정제(n-Hexane : MC)하여 중간체 5-2' 3.4 g(71%) 수득하였다. (m/z=481)
To a solution of Intermediate 5-2 (5.0 g, 0.010 mol), bis (pinacolato) dibron (3.0 g, 0.012 mol), PdCl 2 (dppf) (0.4 g, 0.005 mol) and potassium acetate (2.8 g, 0.020 mol) , 4-dioxane (100 mL), and the mixture was reacted for 24 hours at 95 ° C. After completion of the reaction, the reaction mixture was cooled, and the product was separated into H 2 O: MC and purified by column chromatography (n-hexane: MC) 71%). (m / z = 481)
(4) (4)
제조예Manufacturing example
4 : 화합물 5의 합성 4: Synthesis of
중간체 5-1(5.0 g, 0.011 mol)에 중간체 5-2'(6.2 g, 0.013 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 5> 6.4 g (수율 70%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1), except that Intermediate 5-2 '(6.2 g, 0.013 mol) was added to Intermediate 5-1 (5.0 g, 0.011 mol) Yield: 70%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.17/d, 7.87/d, 7.71/d, 7.62/d, 7.55/d, 7.41/m, 7.36/s, 7.34/m, 7.28/m, 6.75/d, 6.58/d) 2H(7.52/d, 7.51/m, 7.42/m, 7.37/d, 6.63/d, 2.34/s, 1.72/s) 4H(7.54/d, 6.98/d, 6.69/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.17 / d, 7.87 / d, 7.71 / d, 7.62 / d, 7.55 / d, 7.41 / m, 7.36 / s, 7.34 / m, 7.28 / m , 6.75 / d, 6.58 / d) 2H (7.52 / d, 7.51 / m, 7.42 / m, 7.37 / d, 6.63 / d, 2.34 / s, 1.72 / s) / d, 6.51 / d)
LC/MS: m/z=826[(M+1)+]
LC / MS: m / z = 826 [(M + 1) < + &
실시예Example 6 : 화합물 20의 합성 6: Synthesis of Compound 20
(1) (One) 제조예Manufacturing example 1 : 중간체 6-1의 합성 1: Synthesis of intermediate 6-1
3-bromo-1H-pyrrolo[3,2-b]pyridine(5.0 g, 0.026 mol), bis(pinacolato) dibron(7.6 g, 0.030 mol)를 넣고 실시예 5-제조예(3)에서 사용된 동일한 방법으로 <중간체 6-1> 4.5 g(수율 71%) 수득하였다. (m/z=244)
(5.0 g, 0.026 mol) and bis (pinacolato) dibron (7.6 g, 0.030 mol) were added to a solution of the compound 4.5 g (71% yield) of Intermediate 6-1 was obtained. (m / z = 244)
(2) (2) 제조예Manufacturing example 2 : 중간체 6-2의 합성 2: Synthesis of intermediate 6-2
중간체 6-1(5.0 g, 0.020 mol)에 3-bromo-1H-pyrrolo[3,2-b]pyridine(3.3 g, 0.017 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 6-2> 2.8 g (수율 70%)을 얻었다.(m/z=234)
(3-bromo-1H-pyrrolo [3,2-b] pyridine (3.3 g, 0.017 mol) was added to Intermediate 6-1 (5.0 g, 0.020 mol) To obtain 2.8 g (yield 70%) of Intermediate 6-2 (m / z = 234).
(3) (3) 제조예Manufacturing example 3 : 화합물 20의 합성 3: Synthesis of Compound 20
중간체 6-2(5.0 g, 0.021 mol)에 4-bromo-N,N-dip-tolylaniline(14.8 g, 0.042 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 20> 11.9g (수율 73%)을 얻었다.Was synthesized in the same manner as in Example 1 (2), except that 4-bromo-N, N-dip-tolylaniline (14.8 g, 0.042 mol) was added to Intermediate 6-2 (5.0 g, 0.021 mol) To obtain 11.9 g (yield: 73%) of Compound 20.
H-NMR (200MHz, CDCl3):δ ppm, 2H(8.43/d ,7.97/d ,7.22/m ,7.0/s ) 4H(7.37/d ,6.63/d ,2.34/s ) 8H(6.98/d ,6.51/d ) H-NMR (200MHz, CDCl 3 ): δ ppm, 2H (8.43 / d, 7.97 / d, 7.22 / m, 7.0 / s) 4H (7.37 / d, 6.63 / d, 2.34 / s) 8H (6.98 / d , 6.51 / d)
LC/MS: m/z=777[(M+1)+]
LC / MS: m / z = 777 [(M + 1) < + &
실시예Example 7 : 화합물 67의 합성 7: Synthesis of Compound 67
(1) (One) 제조예Manufacturing example 1 : 중간체 7-1의 합성 1: Synthesis of Intermediate 7-1
3-bromo-1H-indole(5.0 g, 0.026 mol)에 bromobenzene(4.1 g, 0.026 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 7-1> 5.3 g (수율 75%)을 얻었다.(m/z=272)
(Intermediate 7-1) was synthesized in the same manner as in Example 1 (2), except that bromobenzene (4.1 g, 0.026 mol) was added to 3-bromo-1H-indole (5.0 g, 0.026 mol) (Yield: 75%). (M / z = 272)
(2) (2) 제조예Manufacturing example 2 : 중간체 7-1'의 합성 2: Synthesis of intermediate 7-1 '
중간체 7-1(5.0 g, 0.018 mol)에 bis(pinacolato)dibron(5.5 g, 0.022 mol) 를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 7-1'> 4.1 g (수율 71%)을 얻었다.(m/z=319)
Intermediate 7-1 'was synthesized in the same manner as in Example 5 (3) except that bis (pinacolato) dibron (5.5 g, 0.022 mol) was added to Intermediate 7-1 (5.0 g, 0.018 mol) 4.1 g (71% yield) of (m / z = 319)
(3) (3) 제조예Manufacturing example 3 : 중간체 7-2의 합성 3: Synthesis of intermediate 7-2
중간체 7-1'(5.0 g, 0.009 mol)에 1,3-dibromo-5-iodobenzene(2.8 g, 0.008 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 7-2> 2.7 g (수율 71%)을 얻었다.(m/z=427)
Intermediate 7-1 '(5.0 g, 0.009 mol) was added 1,3-dibromo-5-iodobenzene (2.8 g, 0.008 mol), and the title compound was synthesized in the same manner as in Example 1- 7-2> 2.7 g (yield: 71%). (M / z = 427)
(4) (4) 제조예Manufacturing example 4 : 중간체 7-3의 합성 4: Synthesis of intermediate 7-3
중간체 7-2(5.0 g, 0.012 mol)에 dip-tolylamine(2.4 g, 0.012 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 7-3> 4.9 g (수율 75%)을 얻었다.(m/z=543)
Intermediate 7-3 was synthesized in the same manner as in Example 1 (2), except that dip-tolylamine (2.4 g, 0.012 mol) was added to Intermediate 7-2 (5.0 g, 0.012 mol) Yield: 75%). (M / z = 543)
(5) (5) 제조예Manufacturing example 5 : 화합물 67의 합성 5: Synthesis of Compound 67
중간체 7-3(5.0 g, 0.009 mol)에 N-(biphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(3.2 g, 0.009 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 67> 5.3 g(수율 72%)을 얻었다.(Biphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (3.2 g, 0.009 mol) was added to Intermediate 7-3 (5.0 g, 0.009 mol) (2) to obtain 5.3 g (yield 72%) of < Compound 67 >.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.17/d, 7.87/d, 7.71/d, 7.62/d, 7.55/d, 7.45/m, 7.41/m, 7.38/m, 7.36/s, 7.28/m, 6.75/s, 6.58/s, 5.73/s) 2H(7.58/m, 7.54/d, 7.52/d, 7.51/m, 7.50/d, 7.42/m, 6.69/d, 6.25/s, 2.34/s, 1.72/s) 4H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.17 / d, 7.87 / d, 7.71 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.41 / m, 7.38 / m, 7.36 / s 7.50 / d, 7.52 / d, 7.52 / d, 7.42 / m, 6.69 / d, 6.25 / s , 2.34 / s, 1.72 / s) 4H (6.98 / d, 6.51 / d)
LC/MS: m/z=825 [(M+1)+]
LC / MS: m / z = 825 [(M + 1) < + &
실시예Example 8 : 화합물 110의 합성 8: Synthesis of compound 110
(1) (One) 제조예Manufacturing example 1 : 중간체 8-1의 합성 1: Synthesis of Intermediate 8-1
3-bromo-6-chloro-1H-indole(5.0 g, 0.022 mol)에 bromobenzene(3.5 g, 0.022 mol)를 넣고 실시예 1-제조예 (6)에서 사용된 동일한 방법으로 합성하여 <화합물 8> 5.2 g (수율 77%)을 얻었다.(m/z=306)
Compound 8 was synthesized by the same method as in Example 1 (6), except that bromobenzene (3.5 g, 0.022 mol) was added to 3-bromo-6-chloro-1H- indole (5.0 g, 0.022 mol) 5.2 g (yield 77%) was obtained. (M / z = 306)
(2) (2) 제조예Manufacturing example 2 : 중간체 8-2의 합성 2: Synthesis of Intermediate 8-2
중간체 8-1(5.0 g, 0.016 mol)에 phenylboronic-acid(2.3 g, 0.019 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 8-2> 3.7 g (수율 77%)을 얻었다.(m/z=303)
Intermediate 8-2 was prepared in the same manner as in Example 1 (1) except that phenylboronic-acid (2.3 g, 0.019 mol) was added to Intermediate 8-1 (5.0 g, 0.016 mol) Yield: 77%). (M / z = 303)
(3) (3) 제조예Manufacturing example 3 : 중간체 8-3의 합성 3: Synthesis of Intermediate 8-3
1-bromo-4-methylbenzene(3.0 g, 0.018 mol)에 5-bromobenzene-1,3-diamine(1.7 g, 0.009 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 8-3> 3.8 g (수율 77%)을 얻었다.(m/z=543)
Was synthesized in the same manner as in Example 1 (2) except that 5-bromobenzene-1,3-diamine (1.7 g, 0.009 mol) was added to 1-bromo-4-methylbenzene (3.0 g, 0.018 mol) 3.8 g (yield: 77%) of Intermediate 8-3 (m / z = 543)
(4) (4) 제조예Manufacturing example 4 : 중간체 8-3'의 합성 4: Synthesis of intermediate 8-3 '
1,4-dibromobenzene(3.0 g, 0.013 mol)에 bis(pinacolato)dibron(8.0 g, 0.032 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 8-3'> 3.0 g (수율 71%)을 얻었다.(m/z=330)
Intermediate 8-3 was synthesized by the same method as in Example 5 (3), except that bis (pinacolato) dibron (8.0 g, 0.032 mol) was added to 1,4-dibromobenzene (3.0 g, 0.013 mol) > 3.0 g (yield 71%). (M / z = 330)
(5) (5) 제조예Manufacturing example 5 : 중간체 8-4의 합성 5: Synthesis of Intermediate 8-4
중간체 8-3(5.0 g, 0.009 mol)에 중간체 8-3' (3.6 g, 0.011 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 8-4> 4.3 g(수율 71%)을 얻었다.(m/z=670)
<Intermediate 8-4> 4.3 g (0.09 mol) of Intermediate 8-3 (5.0 g, 0.009 mol) was added to Intermediate 8-3 (3.6 g, 0.011 mol) g (yield: 71%). (m / z = 670)
(6) (6) 제조예Manufacturing example 6 : 화합물 110의 합성 6: Synthesis of compound 110
중간체 8-2(5.0 g, 0.017 mol)에 중간체 8-4(13.4 g, 0.020 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 110> 10.1 g (수율 73%)을 얻었다.(Compound 10) (10.1 g, yield) was obtained by synthesizing Intermediate 8-4 (13.4 g, 0.020 mol) and Intermediate 8-2 (5.0 g, 0.017 mol) in the same manner as in Example 1- 73%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.27/d, 8.11/d, 7.45/m, 7.41/m, 7.39/s, 7.36/s, 5.73/s) 2H(7.58/m, 7.52/d, 7.51/m, 7.50/d, 6.25/s) 4H(7.25/d, 2.34/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.27 / d, 8.11 / d, 7.45 / m, 7.41 / m, 7.39 / s, 7.36 / s, 5.73 / s) 2H (7.58 / m, 7.52 d, 7.51 / d, 7.50 / d, 6.25 / s) 4H (7.25 / d, 2.34 / s)
LC/MS: m/z=813[(M+1)+]
LC / MS: m / z = 813 [(M + 1) < + &
실시예Example 9 : 화합물 118의 합성 9: Synthesis of Compound 118
(1) (One) 제조예Manufacturing example 1 : 중간체 9-1의 합성 1: Synthesis of intermediate 9-1
2-chloro-1H-indole(3.0 g, 0.020 mol)에 bromobenzene(3.1 g, 0.020 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 9-1> 3.3 g (수율 73%)을 얻었다.(m/z=227)
(3.2 g, 0.020 mol) was added to bromobenzene (3.1 g, 0.020 mol) in the same manner as in Example 1 (2) to give 3.3 g of Intermediate 9-1 (Yield: 73%). (M / z = 227)
(2) (2) 제조예Manufacturing example 2 : 중간체 9-2의 합성 2: Synthesis of intermediate 9-2
1,3,5-tribromobenzene(5.7 g, 0.018 mol)에 9,9-dimethyl-N-(4'-methylbiphenyl-4-yl)-9H-fluoren-2-amine(6.8 g, 0.018 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 9-2> 7.7 g (수율 70%)을 얻었다.(m/z=609)
9,9-dimethyl-N- (4'-methylbiphenyl-4-yl) -9H-fluoren-2-amine (6.8 g, 0.018 mol) was added to 1,3,5-tribromobenzene (M / z = 609) (Intermediate 9-2) (7.7 g, yield 70%) was synthesized in the same manner as in Example 1 (2)
(3) (3) 제조예Manufacturing example 3 : 중간체 9-3의 합성 3: Synthesis of intermediate 9-3
중간체 9-2(5.5 g, 0.009 mol)에 dip-tolylamine(1.8 g, 0.009 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 9-3> 4.6g (수율 71%)을 얻었다.(m/z=725)
Synthesis was conducted in the same manner as in Example 1 (2), except that dip-tolylamine (1.8 g, 0.009 mol) was added to Intermediate 9-2 (5.5 g, 0.009 mol) Yield: 71%). (M / z = 725)
(4) (4) 제조예Manufacturing example 4 : 중간체 9-4의 합성 4: Synthesis of intermediate 9-4
중간체 9-3(5.0 g, 0.007 mol)에 중간체 8-3'(2.6 g, 0.008 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 9-4> 4.0g (수율 67%)을 얻었다.(m/z=848)
Synthesis was conducted in the same manner as in Example 1 (1) except that Intermediate 8-3 '(2.6 g, 0.008 mol) was added to Intermediate 9-3 (5.0 g, 0.007 mol) g (yield: 67%). (m / z = 848)
(5) (5) 제조예Manufacturing example 5 : 화합물 118의 합성 5: Synthesis of Compound 118
중간체 9-1(5.0 g, 0.022 mol)에 중간체 9-4(19.9 g, 0.026 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 118> 13.6 g (수율 67%)을 얻었다.Intermediate 9-4 (19.9 g, 0.026 mol) was added to Intermediate 9-1 (5.0 g, 0.022 mol) and the compound was obtained in the same manner as in Example 1- (1) 67%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.94/d, 7.93/d, 7.87/d, 7.62/d, 7.55/d, 7.45/m, 7.38/m, 7.33/m, 7.28/m, 6.87/m, 6.75/s, 6.60/s, 6.58/d, 5.73/s) 2H(8.30/d, 7.85/d, 7.58/m, 7.54/d, 7.50/d, 7.33/d, 7.29/d, 6.69/d, 6.25/s, 1.72/s) 3H(2.34/s) 4H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.94 / d, 7.93 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.38 / m, 7.33 / m, 7.28 / m D, 7.58 / d, 7.50 / d, 7.33 / d, 7.29 / d, 6.87 / , 6.69 / d, 6.25 / s, 1.72 / s) 3H (2.34 / s)
LC/MS: m/z=915[(M+1)+]
LC / MS: m / z = 915 [(M + 1) < + &
실시예Example 10 : 화합물 120의 합성 10: Synthesis of Compound 120
(1) (One) 제조예Manufacturing example 1 : 화합물 120의 합성 1: Synthesis of Compound 120
중간체 7-1(5.0 g, 0.018 mol)에 중간체 9-4(16.0 g, 0.021 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 10> 11.2 g <수율 68%)을 얻었다.Compound 11 was synthesized in the same manner as in Example 1 (1) except that Intermediate 9-4 (16.0 g, 0.021 mol) was added to Intermediate 7-1 (5.0 g, 0.018 mol) 68%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.17/d, 7.87/d, 7.71/d, 7.62/d, 7.55/d, 7.45/m, 7.38/m, 7.36/s, 7.28/m, 6.75/s, 6.58/d, 5.73/s) 2H(7.58/m, 7.54/d, 7.50/d, 7.42/m, 7.33/d, 7.29/d, 6.69/d, 6.25/s, 1.72/s) 4H(7.25/d, 6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.17 / d, 7.87 / d, 7.71 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.38 / m, 7.36 / s, 7.28 / m , 6.75 / s, 6.58 / d, 5.73 / s) 2H (7.58 m, 7.54 d, 7.50 d, 7.42 m, 7.33 d, 7.29 d, 6.69 d, 6.25 s, ) 4H (7.25 / d, 6.98 / d, 6.51 / d)
LC/MS: m/z=915 [(M+1)+]
LC / MS: m / z = 915 [(M + 1) < + &
실시예Example 11 : 화합물 124의 합성 11: Synthesis of Compound 124
(1) (One) 제조예Manufacturing example 1 : 중간체 11-1의 합성 1: Synthesis of intermediate 11-1
1,3,5-tribromobenzene(3.1 g, 0.010 mol)에 N-(4'-tert-butylbiphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(4.2 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 11-1> 5.1 g (수율 79%)을 얻었다.(m/z=651)
Tert-butylbiphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (4.2 g, 0.010 mol) was added to 1,3,5-tribromobenzene (3.1 g, 0.010 mol) (M / z = 651) (Intermediate 11-1) (5.1 g, Yield: 79%) was obtained by the same method as in Example 1- (2)
(2) (2) 제조예Manufacturing example 2 : 화합물 124의 합성 2: Synthesis of Compound 124
중간체 7-1'(7.7 g, 0.024 mol)에 중간체 11-1(6.5 g, 0.010 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 11> 6.3 g (수율 72%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) except that Intermediate 11-1 (6.5 g, 0.010 mol) was added to Intermediate 7-1 '(7.7 g, 0.024 mol) Yield: 72%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.62/d, 7.55/d, 7.38/m, 7.28/m, 7.06/s, 6.75/s, 6.58/d) 2H(8.17/d, 7.71/d, 7.54/d, 7.45/m, 7.38/d, 7.37/d, 7.36/s, 6.85/s, 6.69/d, 1.72/s) 3H(1.35/s) 4H(7.58/m, 7.50/d, 7.42/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 7.06 / s, 6.75 / s, 6.58 / d) 2H (8.17 7.58 / m, 7.37 / d, 7.36 / s, 6.85 / s, 6.69 / d, 1.72 / s) , 7.50 / d, 7.42 / m)
LC/MS: m/z=877 [(M+1)+]
LC / MS: m / z = 877 [(M + 1) < + &
실시예Example 12 : 화합물 125의 합성 12: Synthesis of Compound 125
(1) (One) 제조예Manufacturing example 1 : 중간체 12-1의 합성 1: Synthesis of Intermediate 12-1
1H-indole(2.3 g, 0.020 mol)에 1,3,5-tribromobenzene(3.1 g, 0.010 mol) 를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 12-1> 2.6 g (수율 68%)을 얻었다.(m/z=387)
Intermediate 12-1 was synthesized by the same method as in Example 1 (2) except that 1,3,5-tribromobenzene (3.1 g, 0.010 mol) was added to 1H-indole (2.3 g, 0.020 mol) 2.6 g (yield 68%) was obtained. (M / z = 387)
(2) (2) 제조예Manufacturing example 2 : 화합물 125의 합성 2: Synthesis of Compound 125
중간체 12-1(5.0 g, 0.013 mol)에 N-(4'-tert-butylbiphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(5.4 g, 0.013 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 125> 6.4 g (수율 68%)을 얻었다.Tert-butylbiphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.4 g, 0.013 mol) was added to Intermediate 12-1 (5.0 g, 0.013 mol) Example 1 - Synthesis was conducted in the same manner as in Production Example (2) to obtain 6.4 g (yield: 68%) of <Compound 125>.
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.62/d, 7.55/d, 7.38/m, 7.28/m, 6.75/s, 6.60/s, 6.58/d) 2H(7.94/d, 7.93/d, 7.60/d, 7.54/d, 7.38/d, 7.37/d, 7.33/m, 6.87/d, 6.69/d, 6.52/d, 6.50/s, 1.72/s) 3H(1.35/s) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 6.75 / s, 6.60 / s, 6.58 / d) 2H (7.94 d, 7.70 / d, 7.60 d, 7.54 d, 7.38 d, 7.37 d, 7.33 m, 6.87 d, 6.69 d, 6.52 d, 6.50 s, 1.72 s) / s)
LC/MS: m/z=724[(M+1)+]
LC / MS: m / z = 724 [(M + 1) < + &
실시예Example 13 : 화합물 30의 합성 13: Synthesis of compound 30
(1) (One) 제조예Manufacturing example 1 : 중간체 13-1의 합성 1: Synthesis of intermediate 13-1
3-bromo-6-chloro-1H-indole(3.0 g, 0.013 mol)에 4-bromoaniline(2.2 g, 0.013 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 13-1> 3.0 g <수율 73%)을 얻었다.(m/z=321)
Was synthesized in the same manner as in Example 1 (2) except that 4-bromoaniline (2.2 g, 0.013 mol) was added to 3-bromo-6-chloro-1H- indole (3.0 g, 0.013 mol) 13-1> 3.0 g <yield: 73%). (M / z = 321)
(2) (2) 제조예Manufacturing example 2 : 중간체 13-2의 합성 2: Synthesis of intermediate 13-2
중간체 13-1(3.2 g, 0.010 mol)에 1-bromo-4-methylbenzene(3.4 g, 0.020 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 13-2> 3.5 g (수율 75%)을 얻었다.(m/z=467)
Synthesis was conducted in the same manner as in Example 1 (2) except that 1-bromo-4-methylbenzene (3.4 g, 0.020 mol) was added to Intermediate 13-1 (3.2 g, 0.010 mol) > 3.5 g (yield 75%). (M / z = 467)
(3) (3) 제조예Manufacturing example 3 : 중간체 13-3의 합성 3: Synthesis of intermediate 13-3
중간체 13-2(5.0 g, 0.011 mol)에 9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine(3.2 g, 0.011 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 13-3> 5.7 g (수율 72%)을 얻었다.(m/z=720)
To the intermediate 13-2 (5.0 g, 0.011 mol) was added 9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine (3.2 g, 0.011 mol) (M / z = 720) (yield: 72%) of Intermediate 13-3
(4) (4) 제조예Manufacturing example 4 : 화합물 30의 합성 4: Synthesis of compound 30
중간체 13-2(7.2 g, 0.010 mol)에 3,5-di-tert-butylphenylboronic acid(2.8 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 30> 5.3 g (수율 60%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) except that 3,5-di-tert-butylphenylboronic acid (2.8 g, 0.012 mol) was added to Intermediate 13-2 (7.2 g, 0.010 mol) 30> (yield: 60%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.49/d, 8.10/d, 7.87/d, 7.62/d, 755/d, 7.41/s, 7.38/m, 7.28/m, 6.75/d, 6.58/d) 2H(7.82/s, 7.60/s, 7.37/d, 6.63/d, 1.72/s) 3H(2.34/s) 6H(6.98/d, 6.51/d, 1.35/s) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.49 / d, 8.10 / d, 7.87 / d, 7.62 / d, 755 / d, 7.41 / s, 7.38 / m, 7.28 / m, 6.75 / d , 6.58 / d) 2H (7.82 / s, 7.60 / s, 7.37 / d, 6.63 / d, 1.72 / s)
LC/MS: m/z=875[(M+1)+]
LC / MS: m / z = 875 [(M + 1) < + &
실시예Example 14 : 화합물 59의 합성 14: Synthesis of Compound 59
(1) (One) 제조예Manufacturing example 1 : 중간체 14-1의 합성 1: Synthesis of intermediate 14-1
dip-tolylamine(5.0 g, 0.015 mol)에 1,4-dibromobenzene(3.5 g, 0.015 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체14-1> 4.0 g (수율 75%)을 얻었다.(m/z=352)
Synthesis was conducted in the same manner as in Example 1 (2), except that 1.4-dibromobenzene (3.5 g, 0.015 mol) was added to dip-tolylamine (5.0 g, 0.015 mol) (Yield: 75%). (M / z = 352)
(2) (2) 제조예Manufacturing example 2 : 중간체 14-1'의 합성 2: Synthesis of intermediate 14-1 '
중간체 1-5(3.0 g, 0.010 mol), bis(pinacolato)dibron(3.0 g, 0.012 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 14-1'> 2.5 g (수율 71%)을 얻었다.(m/z=353)
Intermediate 14-1 'was synthesized in the same manner as in Example 5 (3), except that Intermediate 1-5 (3.0 g, 0.010 mol) and bis (pinacolato) dibron (3.0 g, 0.012 mol) 2.5 g (yield 71%) of the title compound was obtained (m / z = 353)
(3) (3) 제조예Manufacturing example 3 : 중간체 14-2의 합성 3: Synthesis of intermediate 14-2
중간체 14-1(3.0 g, 0.009 mol), 중간체 14-1'(3.5 g, 0.010 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 14-2> 3.2 g (수율 71%)을 얻었다.(m/z=499)
Intermediate 14-2 > 3.2 (3 g, 0.010 mol) was synthesized in the same manner as in Example 1 (1) except that Intermediate 14-1 (3.0 g, 0.009 mol) and Intermediate 14-1 ' g (yield: 71%). (m / z = 499)
(4) (4) 제조예Manufacturing example 4 : 중간체 14-3의 합성 4: Synthesis of intermediate 14-3
N-(4'-tert-butylbiphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (5.0 g, 0.012 mol)에 1,4-dibromobenzene(2.8 g, 0.012 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 14-3> 4.6 g (수율 71%)을 얻었다.(m/z=572)
1,4-dibromobenzene (2.8 g, 0.012 mol) was added to N- (4'-tert-butylbiphenyl-4-yl) -9,9-dimethyl-9H- fluoren- Synthesis was conducted in the same manner as in Example 1 (2) to obtain 4.6 g (yield: 71%) of Intermediate 14-3 (m / z = 572)
(5) (5) 제조예Manufacturing example 5 : 중간체 14-4의 합성 5: Synthesis of intermediate 14-4
중간체 14-3(5.7 g, 0.010 mol)에 bis(pinacolato)dibron(3.0 g, 0.012 mol) 를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체14-4> 4.6 g (수율 75%)을 얻었다.(m/z=619)
Intermediate 14-4 was synthesized by the same method as in Example 5 (3), except that bis (pinacolato) dibron (3.0 g, 0.012 mol) was added to Intermediate 14-3 (5.7 g, 0.010 mol) g (yield 75%). (m / z = 619)
(6) (6) 제조예Manufacturing example 6 : 화합물 59의 합성 6: Synthesis of Compound 59
중간체 14-2(5.0 g, 0.010 mol)에 중간체 14-4(7.4 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 59> 7.2 g (수율 75%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) except that Intermediate 14-4 (7.4 g, 0.012 mol) was added to Intermediate 14-2 (5.0 g, 0.010 mol) 75%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.27/d, 8.11/d, 7.87/d, 7.62/d, 7.55/d, 7.45/m, 7.39/s, 7.38/m, 7.36/s, 7.28/m, 6.75/s, 6.58/d) 2H(7.58/m, 7.50/d, 7.38/d, 7.37/d, 2.34/s, 1.72/s) 3H(1.35/s) 4H(6.98/d, 6.51/d) 6H(7.54/d, 6.69/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.27 / d, 8.11 / d, 7.87 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.39 / s, 7.38 / m, 7.36 / s 1.58 / d) 2H (7.58 / m, 7.50 / d, 7.38 / d, 7.37 / d, 2.34 / s, 1.72 / s) , 6.51 / d) 6H (7.54 / d, 6.69 / d)
LC/MS: m/z= 957[(M+1)+]
LC / MS: m / z = 957 [(M + 1) < + &
실시예Example 15 : 화합물 70의 합성 15: Synthesis of Compound 70
(1) (One) 제조예Manufacturing example 1 : 중간체 15-1의 합성 1: Synthesis of intermediate 15-1
3-bromo-5-chloro-1H-indole(5.0 g, 0.013 mol)에 bromobenzene(2.0 g, 0.013 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 15-1> 3.0 g (수율 75%)을 얻었다.(m/z=306)
Was synthesized by the same method as in Example 1 (2), except that bromobenzene (2.0 g, 0.013 mol) was added to 3-bromo-5-chloro-1H- indole (5.0 g, 0.013 mol) 1> 3.0 g (yield 75%). (M / z = 306)
(2) (2) 제조예Manufacturing example 2 : 중간체 15-2의 합성 2: Synthesis of intermediate 15-2
중간체 15-1(3.0 g, 0.010 mol)에 phenylboronic acid(1.9 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 15-2> 2.2 g (수율 72%)을 얻었다.(m/z=303)
Intermediate 15-2 (2.2 g, yield) was synthesized in the same manner as in Example 1 (1) except that phenylboronic acid (1.9 g, 0.012 mol) was added to Intermediate 15-1 (3.0 g, 0.010 mol) 72%). (M / z = 303)
(3) (3) 제조예Manufacturing example 3 : 중간체 15-3의 합성 3: Synthesis of intermediate 15-3
중간체 14-1(3.0 g, 0.010 mol)에 bis(pinacolato)dibron(3.0 g, 0.012 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 15-3> 2.8 g (수율 72%)을 얻었다.(m/z=395)
Intermediate 15-3> 2.8 (3.0 g, 0.012 mol) was added to the intermediate 14-1 (3.0 g, 0.010 mol) and bis (pinacolato) dibron g (yield: 72%). (m / z = 395)
(4) (4) 제조예Manufacturing example 4 : 화합물 70의 합성 4: Synthesis of Compound 70
중간체 15-3(4.0 g, 0.010 mol)에 중간체 9-3(5.8 g, 0.008 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 70> 5.2g (수율 72%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) except that Intermediate 9-3 (5.8 g, 0.008 mol) was added to Intermediate 15-3 (4.0 g, 0.010 mol) 72%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.27/d, 7.87/d, 7.77/d, 7.62/d, 7.55/d, 7.45/m, 7.39/s, 7.38/m, 7.36/s, 7.28/m, 6.75/s, 6.58/d, 5.73/s) 2H(7.58/m, 7.54/d, 7.50/d, 7.41/m, 6.69/d, 6.25/d, 2.34/s, 1.72/s) 4H(7.52/d, 7.51/m, 6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.27 / d, 7.87 / d, 7.77 / d, 7.62 / d, 7.55 / d, 7.45 / m, 7.39 / s, 7.38 / m, 7.36 / s 7.58 / d, 7.50 / d, 7.41 / m, 6.69 / d, 6.25 / d, 2.34 / s, 1.72 / s ) 4H (7.52 / d, 7.51 / m, 6.98 / d, 6.51 / d)
LC/MS: m/z=901[(M+1)+]
LC / MS: m / z = 901 [(M + 1) < + &
실시예Example 16 : 화합물 33의 합성 16: Synthesis of Compound 33
(1) (One) 제조예Manufacturing example 1 : 중간체 16-1의 합성 1: Synthesis of intermediate 16-1
1,1-dimethyl-1H-indene(3.0 g, 0.020 mol)에 N-bromosuccinimide(7.2 g, 0.040 mol)를 넣고 실시예 4-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 16-1> 2.2 g (수율 37%)을 얻었다.(m/z=302)
Was synthesized by the same method as in Example 4 (3) except that N-bromosuccinimide (7.2 g, 0.040 mol) was added to 1,1-dimethyl-1H-indene (3.0 g, 0.020 mol) 1> 2.2 g (yield: 37%). (M / z = 302)
(2) (2) 제조예Manufacturing example 2 : 중간체 16-2의 합성 2: Synthesis of intermediate 16-2
중간체 16-1(3.0 g, 0.010 mol)에 bis(pinacolato)dibron(2.5 g, 0.010 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 16-2> 2.5 g (수율 72%)을 얻었다.(m/z=349)
Intermediate 16-2 was synthesized by the same method as in Example 5 (3) except that bis (pinacolato) dibron (2.5 g, 0.010 mol) was added to Intermediate 16-1 (3.0 g, 0.010 mol) g (yield: 72%). (m / z = 349)
(3) (3) 제조예Manufacturing example 3 : 중간체 16-3의 합성 3: Synthesis of intermediate 16-3
중간체 16-1(3.0 g, 0.010 mol)에 1-bromothianthrene(4.2 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 16-3> 3.3 g (수율 75%)을 얻었다.(m/z=444)
3.3 g of Intermediate 16-3 was synthesized in the same manner as in Example 1 (1) except that 1-bromothianthrene (4.2 g, 0.012 mol) was added to Intermediate 16-1 (3.0 g, 0.010 mol) Yield: 75%). (M / z = 444)
(4) (4) 제조예Manufacturing example 4 : 중간체 16-4의 합성 4: Synthesis of intermediate 16-4
중간체 16-3(5.0 g, 0.011 mol)에 bis(pinacolato)dibron(6.3 g, 0.025 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 16-4> 3.8 g (수율 64%)을 얻었다.(m/z=538)
(Intermediate 16-4)> 3.8 (0.025 mol) was added to Intermediate 16-3 (5.0 g, 0.011 mol), and bis (pinacolato) dibron g (yield: 64%). (m / z = 538)
(5) (5) 제조예Manufacturing example 5 : 화합물 33의 합성 5: Synthesis of Compound 33
중간체 16-4(5.0 g, 0.009 mol)에 4-bromo-N,N-dip-tolylaniline(6.3 g, 0.018 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 33> 5.5 g (수율 74%)을 얻었다.Synthesis was carried out in the same manner as in Example 1 (1) except that 4-bromo-N, N-dip-tolylaniline (6.3 g, 0.018 mol) was added to Intermediate 16-4 (5.0 g, 0.009 mol) 5.5 g (yield: 74%) of Compound 33 was obtained.
H-NMR (200MHz, CDCl3):δ ppm, 2H(7.81/s, 7.41/d, 7.36/d, 6.60/s) 4H(7.54/d, 6.69/d, 2.34/s, 1.72/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 2H (7.81 / s, 7.41 / d, 7.36 / d, 6.60 / s) 4H (7.54 / d, 6.69 / d, 2.34 / s, 1.72 / s) 8H (6.98 / d, 6.51 / d)
LC/MS: m/z=830[(M+1)+]
LC / MS: m / z = 830 [(M + 1) < + &
실시예Example 17 : 화합물 35의 합성 17: Synthesis of Compound 35
(1) (One) 제조예Manufacturing example 1 : 중간체 17-1의 합성 1: Synthesis of intermediate 17-1
중간체 16-1(3.0 g, 0.010 mol)에 bis(pinacolato)dibron(2.5 g, 0.020 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 17-1> 2.8 g (수율 70%)을 얻었다.(m/z=396)
(2.5 g, 0.020 mol) was added to Intermediate 16-1 (3.0 g, 0.010 mol) and bis (pinacolato) dibron (2.5 g, 0.020 mol) (M / z = 396) of the title compound (17-1) (yield: 70%).
(2) (2) 제조예Manufacturing example 2 : 화합물 35의 합성 2: Synthesis of Compound 35
중간체 17-1(5.0 g, 0.013 mol)에 4-bromo-N,N-dip-tolylaniline(9.2 g, 0.026 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 35> 6.3 g (수율 70%)을 얻었다.Was synthesized in the same manner as in Example 1 (1) except that 4-bromo-N, N-dip-tolylaniline (9.2 g, 0.026 mol) was added to Intermediate 17-1 (5.0 g, 0.013 mol) To obtain 6.3 g (yield 70%) of Compound 35.
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.86/s, 7.48/d, 7.46/d, 6.94/s) 2H(7.54/d, 7.25/d, 6.69/d, 6.63/d, 1.69/s) 4H(2.34/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.86 / s, 7.48 / d, 7.46 / d, 6.94 / s) 2H (7.54 / d, 7.25 / d, 6.69 / d, 6.63 / d, 1.69 / s) 4H (2.34 / s) 8H (6.98 / d, 6.51 / d)
LC/MS: m/z=687[(M+1)+]
LC / MS: m / z = 687 [(M + 1) < + &
실시예Example 18 : 화합물 87의 합성 18: Synthesis of Compound 87
(1) (One) 제조예Manufacturing example 1 : 중간체 18-1의 합성 1: Synthesis of intermediate 18-1
중간체 16-2(5.0 g, 0.014 mol)에 N-(4'-tert-butylbiphenyl-4-yl)-9,9-dimethyl-9H-fluoren-2-amine(5.0 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 18-1> 5.8 g (수율 70%)을 얻었다.(m/z=685)
Tert-butylbiphenyl-4-yl) -9,9-dimethyl-9H-fluoren-2-amine (5.0 g, 0.012 mol) was added to Intermediate 16-2 Synthesis was conducted in the same manner as in Example 1 (1) to obtain 5.8 g (yield: 70%) of Intermediate 18-1 (m / z = 685)
(2) (2) 제조예Manufacturing example 2 : 화합물 87의 합성 2: Synthesis of Compound 87
중간체 18-1(5.0 g, 0.007 mol)에 4-bromo-N,N-dip-tolylaniline(2.1 g, 0.006 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 87> 3.6 g (수율 72%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) except that 4-bromo-N, N-dip-tolylaniline (2.1 g, 0.006 mol) was added to Intermediate 18-1 (5.0 g, 0.007 mol) 3.6 g (yield: 72%) of Compound 87 was obtained.
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.62/d, 7.55/d, 7.38/m, 7.28/m, 7.17/d, 6.94/s, 6.75/s, 6.62/s, 6.58/d, 6.45/d) 2H(7.54/d, 7.38/d, 7.37/d, 7.25/d, 6.69/d, 6.63/d) 3H(1.35/s) 4H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 7.17 / d, 6.94 / s, 6.75 / s, 6.62 / s , 6.58 / d, 6.45 / d) 2H (7.54 / d, 7.38 / d, 7.37 / d, 7.25 / d, 6.69 / d, 6.63 / )
LC/MS: m/z=832[(M+1)+]
LC / MS: m / z = 832 [(M + 1) < + &
실시예Example 19 : 화합물 137의 합성 19: Synthesis of Compound 137
(1) (One) 제조예Manufacturing example 1 : 중간체 19-1의 합성 1: Synthesis of intermediate 19-1
중간체 4-3(3.0 g, 0.010 mol)에 bis(pinacolato)dibron(2.5 g, 0.010 mol) 를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 19-1> 2.5 g (수율 72%)을 얻었다.(m/z=349)
Intermediate 19-1> 2.5 (0.010 mol) was added to the intermediate 4-3 (3.0 g, 0.010 mol) and bis (pinacolato) dibron g (yield: 72%). (m / z = 349)
(2) (2) 제조예Manufacturing example 2 : 화합물 137의 합성 2: Synthesis of Compound 137
중간체 19-3(2.2 g, 0.010 mol)에 중간체 9-3(5.5 g, 0.008 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 137> 6.1 g (수율 73%)을 얻었다.Intermediate 9-3 (5.5 g, 0.008 mol) was added to Intermediate 19-3 (2.2 g, 0.010 mol) and the compound was used in the same manner as in Example 1- (1) 73%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.62/d, 7.55/d, 7.42/d, 7.38/m, 7.30/d, 7.28/m, 7.27/m, 7.22/m, 6.94/s, 6.75/s, 6.58/d, 5.62/s) 2H(7.54/d, 7.38/d, 7.37/d, 6.69/d, 5.92/s, 2.34/s, 1.72/s, 1.69/s) 3H(1.35/s) 4H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.42 / d, 7.38 / m, 7.30 / d, 7.28 / m, 7.27 / m, 7.22 / m D, 7.37 / d, 6.69 / d, 5.92 / s, 2.34 / s, 1.72 / s, 1.69 / s ) 3H (1.35 / s) 4H (6.98 / d, 6.51 / d)
LC/MS: m/z=832[(M+1)+]
LC / MS: m / z = 832 [(M + 1) < + &
실시예Example 20 : 화합물 143의 합성 20: Synthesis of compound 143
(1) (One) 제조예Manufacturing example 1 : 중간체 20-1의 합성 1: Synthesis of intermediate 20-1
중간체 19-1(5.0 g, 0.013 mol)에 3,5-dibromophenylboronic acid(4.2 g, 0.015 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 20-1> 3.4 g (수율 70%)을 얻었다.(m/z=378)
Intermediate 20-1 was synthesized in the same manner as in Example 1 (1) except that 3,5-dibromophenylboronic acid (4.2 g, 0.015 mol) was added to Intermediate 19-1 (5.0 g, 0.013 mol) 3.4 g (yield 70%) was obtained. (M / z = 378)
(2) (2) 제조예Manufacturing example 2 : 중간체 20-2의 합성 2: Synthesis of intermediate 20-2
중간체 20-1(5.0 g, 0.013 mol)에 dip-tolylamine(2.6 g, 0.013 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 20-2> 4.9 g (수율 76%)을 얻었다.(m/z=494)
Intermediate 20-2 was synthesized in the same manner as in Example 1- (2), except that dip-tolylamine (2.6 g, 0.013 mol) was added to Intermediate 20-1 (5.0 g, 0.013 mol) Yield: 76%). (M / z = 494)
(3) (3) 제조예Manufacturing example 3 : 중간체 20-3의 합성 3: Synthesis of intermediate 20-3
중간체 20-2(5.0 g, 0.010 mol)에 9,9-dimethyl-9H-fluoren-2-amine(2.1 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 20-3> 4.6 g (수율 74%)을 얻었다.(m/z=622)
Synthesis was carried out in the same manner as in Example 1 (2) except that 9,9-dimethyl-9H-fluoren-2-amine (2.1 g, 0.010 mol) was added to Intermediate 20-2 (5.0 g, 0.010 mol) To obtain 4.6 g (yield: 74%) of Intermediate 20-3. (M / z = 622)
(4) (4) 제조예Manufacturing example 4 : 화합물 143의 합성 4: Synthesis of compound 143
중간체 20-3(5.0 g, 0.008 mol)에 diphenyl-bromo-tert-butylbenzene(2.9 g, 0.008 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 143> 5.2 g (수율 71%)을 얻었다.(m/z=578)The compound 143 (5.2 g, 0.008 mol) was synthesized in the same manner as in Example 1 (2) except that diphenyl-bromo-tert-butylbenzene (2.9 g, 0.008 mol) g (yield: 71%). (m / z = 578)
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.70/s, 7.62/d, 7.57/m, 7.55/d, 7.44/m, 7.42/d, 7.38/m, 7.30/d, 7.28/m, 7.27/m, 7.22/m, 6.94/s, 6.89/d, 6.88/d, 6.75/s, 6.59/d, 6.58/d, 5.92/s, 5.62/s) 2H(7.48/d, 7.38/d, 7.37/d, 2.34/s, 1.72/s, 1.69/s) 3H(1.35/s) 4H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.70 / s, 7.62 / d, 7.57 / m, 7.55 / d, 7.44 / m, 7.42 / d, 7.38 / m, 7.30 / d , 7.28 / m, 7.27 / m, 7.22 / m, 6.94 / s, 6.89 / d, 6.88 / d, 6.75 / s, 6.59 / d, 6.58 / d, 5.92 / s, 5.62 / , 7.38 / d, 7.37 / d, 2.34 / s, 1.72 / s, 1.69 / s)
LC/MS: m/z=908[(M+1)+]
LC / MS: m / z = 908 [(M + 1) < + &
실시예Example 21 : 화합물 184의 합성 21: Synthesis of compound 184
(1) (One) 제조예Manufacturing example 1 : 중간체 21-1의 합성 1: Synthesis of intermediate 21-1
중간체 19-1(10.0 g, 0.026 mol)에 5-bromo-1,3-phenylenediboronic acid(3.7 g, 0.015 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 21-1> 4.1 g (수율 71%)을 얻었다.(m/z=441)
Intermediate 19-1 (10.0 g, 0.026 mol) was synthesized in the same manner as in Example 1 (1) except that 5-bromo-1,3-phenylenediboronic acid (3.7 g, 0.015 mol) 21-1> 4.1 g (yield: 71%). (M / z = 441)
(2) (2) 제조예Manufacturing example 2 : 중간체 21-2의 합성 2: Synthesis of intermediate 21-2
중간체 21-1(5.0 g, 0.011 mol)에 9,9-dimethyl-9H-fluoren-2-amine(2.3 g, 0.011 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 21-2> 4.7g (수율 75%)을 얻었다.(m/z=569)
(2.3 g, 0.011 mol) was added to Intermediate 21-1 (5.0 g, 0.011 mol) and 9,9-dimethyl-9H-fluoren- To obtain 4.7 g (yield 75%) of Intermediate 21-2. (M / z = 569)
(3) (3) 제조예Manufacturing example 3 : 화합물 184의 합성 3: Synthesis of Compound 184
중간체 21-2(5.0 g, 0.009 mol)에 4-bromo-4'-tert-butylbiphenyl(2.6 g, 0.009 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 184> 5.3 g (수율 75%)을 얻었다.(2.6 g, 0.009 mol) was added to Intermediate 21-2 (5.0 g, 0.009 mol) and 4-bromo-4'-tert-butylbiphenyl 184> 5.3 g (yield 75%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.62/d, 7.55/d, 7.38/m, 7.28/m, 6.75/s, 6.58/d, 6.28/s) 2H(7.54/d, 7.42/d, 7.38/d, 7.37/d, 7.30/d, 7.27/m, 7.22/m, 6.94/s, 6.69/d, 6.41/s) 3H(1.35/s) 4H(1.69/s) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 6.75 / s, 6.58 / d, 6.28 / s) 2H (7.54 d), 7.37 / d, 7.30 / d, 7.27 / m, 7.22 / m, 6.94 / s, 6.69 / d, 6.41 / s) )
LC/MS: m/z= 779[(M+1)+]
LC / MS: m / z = 779 [(M + 1) < + &
실시예Example 22 : 화합물 140의 합성 22: Synthesis of Compound 140
(1) (One) 제조예Manufacturing example 1 : 화합물 140의 합성 1: Synthesis of Compound 140
중간체 4-3(5.0 g, 0.013 mol), 중간체 9-4(11.6 g, 0.015 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 140> 6.8 g (수율 61%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1), except that Intermediate 4-3 (5.0 g, 0.013 mol) and Intermediate 9-4 (11.6 g, 0.015 mol) 61%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.62/d, 7.55/d, 7.42/d, 7.38/m, 7.30/d, 7.28/m, 7.27/m, 7.22/m, 6.94/s, 6.75/s, 6.58/d, 5.73/s) 2H(7.64/d, 7.56/d, 7.54/d, 7.33/d, 7.29/d, 6.69/d, 6.25/s, 1.72/s, 1.69/s) 3H(2.34/s) 4H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.42 / d, 7.38 / m, 7.30 / d, 7.28 / m, 7.27 / m, 7.22 / m , 6.94 / s, 6.75 / s, 6.58 / d, 5.73 / s) 2H (7.64 d, 7.56 d, 7.54 d, 7.33 d, 7.29 d, 6.69 d, 6.25 s, , 1.69 / s) 3H (2.34 / s) 4H (6.98 / d, 6.51 / d)
LC/MS: m/z=866[(M+1)+]
LC / MS: m / z = 866 [(M + 1) < + &
실시예Example 23 : 화합물 147의 합성 23: Synthesis of Compound 147
(1) (One) 제조예Manufacturing example 1 : 화합물 147의 합성 1: Synthesis of Compound 147
중간체 21-2(5.0 g, 0.009 mol)에 4-bromo-4'-methylbiphenyl(2.3 g, 0.009 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물23> 5.0g (수율 75%)을 얻었다.Compound 23 was synthesized by the same method as in Example 1 (2) except that 4-bromo-4'-methylbiphenyl (2.3 g, 0.009 mol) was added to Intermediate 21-2 (5.0 g, 0.009 mol) (Yield: 75%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d ,7.62/d ,7.55/d ,7.38/m ,7.28/m ,6.75/s ,6.58/d ,6.28/s ,2.34/s ) 2H(7.54/d ,7.42/d ,7.33/m ,7.30/d ,7.29/d ,7.27/m ,7.22/m ,6.94/s ,6.69/d ,6.41/s ,1.72/s ) 4H(1.69/s ) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 6.75 / s, 6.58 / d, 6.28 / s, 2.34 / s ) 2H (7.54 / d, 7.42 / d, 7.33 / m, 7.30 / d, 7.29 / d, 7.27 / m, 7.22 / m, 6.94 / s, 6.69 / / s)
LC/MS: m/z=736[(M+1)+]
LC / MS: m / z = 736 [(M + 1) < + &
실시예Example 24 : 화합물 146의 합성 24: Synthesis of Compound 146
(1) (One) 제조예Manufacturing example 1 : 중간체 24-1의 합성 1: Synthesis of intermediate 24-1
중간체 4-3(2.2 g, 0.010 mol)에 bromobenzene(3.1 g, 0.020 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 24-1> 1.9 g (수율 54%)을 얻었다.(m/z=347)
(3.1 g, 0.020 mol) was added to Intermediate 4-3 (2.2 g, 0.010 mol) in the same manner as in Example 1-Preparation Example (2) to obtain 1.9 g of Intermediate 24-1 %). (M / z = 347)
(2) (2) 제조예Manufacturing example 2 : 화합물 146의 합성 2: Synthesis of Compound 146
중간체 24-1(2.0 g, 0.014 mol)에 중간체 9-4(13.0 g, 0.017 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 146> 8.5 g (수율 61%)을 얻었다.(m/z=281)Synthesis was carried out in the same manner as in Example 1 (1) except that Intermediate 9-4 (13.0 g, 0.017 mol) was added to Intermediate 24-1 (2.0 g, 0.014 mol) 61%). (M / z = 281)
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.62/d, 7.55/d, 7.38/m, 7.28/m, 6.75/s, 6.58/d, 5.73/s) 2H(7.64/d, 7.56/d, 7.54/d, 7.38/d, 7.29/d, 6.69/d, 6.25/s, 1.72/s) 3H(7.26/m, 2.34/s) 4H(6.98/d, 6.51/d) 6H(7.33/m, 7.23/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 6.75 / s, 6.58 / d, 5.73 / s) 2H (7.64 d, 7.56 / d, 7.54 / d, 7.38 / d, 7.29 / d, 6.69 / d, 6.25 / s, 1.72 / s) ) 6H (7.33 / m, 7.23 / d)
LC/MS: m/z=990[(M+1)+]
LC / MS: m / z = 990 [(M + 1) < + &
실시예Example 25 : 화합물 160의 합성 25: Synthesis of Compound 160
(1) (One) 제조예Manufacturing example 1 : 중간체 25-1의 합성 1: Synthesis of intermediate 25-1
3-chloro-1H-indole(2.0 g, 0.013 mol)에 N-bromosuccinimide(2.3 g, 0.013 mol)를 넣고 실시예 4-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 25-1> 1.2 g (수율 41%)을 얻었다.(m/z=230)
Intermediate 25-1 was synthesized by the same method as in Example 4 (3), except that N-bromosuccinimide (2.3 g, 0.013 mol) was added to 3-chloro-1H- indole (2.0 g, 0.013 mol) 1.2 g (yield 41%) was obtained. (M / z = 230)
(2) (2) 제조예Manufacturing example 2 : 중간체 25-2의 합성 2: Synthesis of intermediate 25-2
중간체 25-1(2.3 g, 0.010 mol)에 phenyl boronic acid(1.4 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 25-2> 1.6 g (수율 71%)을 얻었다.(m/z=227)
1.6 g (intermediate 25-2) was synthesized by the same procedure as in Example 1 (1) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to intermediate 25-1 (2.3 g, 0.010 mol) Yield: 71%). (M / z = 227)
(3) (3) 제조예Manufacturing example 3 : 중간체 25-3의 합성 3: Synthesis of intermediate 25-3
중간체 25-2(2.3 g, 0.010 mol)에 9H-carbazol-3-ylboronic acid(2.5 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 25-3> 2.5 g (수율 70%)을 얻었다.(m/z=358)
Intermediate 25-2 (2.3 g, 0.010 mol) was synthesized in the same manner as in Example 1 (1) except that 9H-carbazol-3-ylboronic acid (2.5 g, 0.012 mol) 3> 2.5 g (yield 70%). (M / z = 358)
(4) (4) 제조예Manufacturing example 4 : 화합물 160의 합성 4: Synthesis of Compound 160
중간체 25-3(3.6 g, 0.010 mol)에 4-bromo-N,N-dip-tolylaniline(7.0 g, 0.020 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 160> 6.8 g (수율 75%)을 얻었다.Synthesis was carried out in the same manner as in Example 1 (2) except that 4-bromo-N, N-dip-tolylaniline (7.0 g, 0.020 mol) was added to Intermediate 25-3 (3.6 g, 0.010 mol) 6.8 g (yield 75%) of Compound 160 was obtained.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.55/d, 8.17/d, 7.94/d, 7.87/d, 7.77/s, 7.71/d, 7.69/d, 7.41/m, 7.33/m, 7.25/m) 2H(7.79/d, 7.51/m, 7.42/m) 4H(7.37/d, 6.63/d, 2.34/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.55 / d, 8.17 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.71 / d, 7.69 / d, 7.41 / m, 7.33 / m , 7.25 / m) 2H (7.79 / d, 7.51 / m, 7.42 / m) 4H (7.37 / d, 6.63 / d, 2.34 /
LC/MS: m/z=901[(M+1)+]
LC / MS: m / z = 901 [(M + 1) < + &
실시예Example 26 : 화합물 151의 합성 26: Synthesis of Compound 151
(1) (One) 제조예Manufacturing example 1 : 중간체 26-1의 합성 1: Synthesis of intermediate 26-1
중간체 25-2(2.3 g, 0.010 mol)에 4-bromo-N,N-dip-tolylaniline(3.5 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 26-1> 3.6 g (수율 73%)을 얻었다.(m/z=499)
Was synthesized in the same manner as in Example 1 (2) except that 4-bromo-N, N-dip-tolylaniline (3.5 g, 0.010 mol) was added to Intermediate 25-2 (2.3 g, 0.010 mol) To obtain 3.6 g (yield: 73%) of intermediate 26-1 (m / z = 499)
(2) (2) 제조예Manufacturing example 2 : 화합물 151의 합성 2: Synthesis of Compound 151
중간체 26-1(5.0 g, 0.010 mol)에 중간체 5-2'(6.8 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 151> 4.9 g (수율 54%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (1) except that Intermediate 5-2 '(6.8 g, 0.012 mol) was added to Intermediate 26-1 (5.0 g, 0.010 mol) Yield: 54%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.17/d, 7.87/d, 7.71/d, 7.62/d, 7.55/d, 7.38/m, 7.28/m, 6.75/s, 6.58/d) 2H(7.79/d, 7.52/d, 7.42/m, 7.41/m, 7.37/d, 6.63/d, 2.34/s, 1.72/s) 4H(7.54/d, 7.51/m, 6.98/d, 6.69/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.17 / d, 7.87 / d, 7.71 / d, 7.62 / d, 7.55 / d, 7.38 / m, 7.28 / m, 6.75 / s, 6.58 / d M, 6.98 / d, 6.69 / d, 7.52 / d, 7.42 / d, 7.41 / m, 7.37 / d, 6.63 / d, / d, 6.51 / d)
LC/MS: m/z=900[(M+1)+]
LC / MS: m / z = 900 [(M + 1) < + &
실시예Example 27 : 화합물 165의 합성 27: Synthesis of Compound 165
(1) (One) 제조예Manufacturing example 1 : 중간체 27-1의 합성 1: Synthesis of intermediate 27-1
6-chloro-3-iodo-1H-indole(3.6 g, 0.013 mol)에 N-bromosuccinimide(2.3 g, 0.013 mol)를 넣고 실시예 4-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 27-1> 1.9 g (수율 42%)을 얻었다.(m/z=357)
N-bromosuccinimide (2.3 g, 0.013 mol) was added to 6-chloro-3-iodo-1H-indole (3.6 g, 0.013 mol) 27-1> 1.9 g (yield: 42%). (M / z = 357)
(2) (2) 제조예Manufacturing example 2 : 중간체 27-2의 합성 2: Synthesis of intermediate 27-2
중간체 27-1(3.6 g, 0.010 mol)에 9,9-dimethyl-N-p-tolyl-9H-fluoren-2-amine(3.0 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 27-2> 3.2 g (수율 61%)을 얻었다.(m/z=527)
To the intermediate 27-1 (3.6 g, 0.010 mol) was added 9,9-dimethyl-Np-tolyl-9H-fluoren-2-amine (3.0 g, 0.010 mol) 3.2 g (yield: 61%) of Intermediate 27-2 (m / z = 527) was obtained in the same manner as Intermediate 27-2.
(3) (3) 제조예Manufacturing example 3 : 중간체 27-3의 합성 3: Synthesis of intermediate 27-3
중간체 27-2(5.3 g, 0.010 mol)에 phenyl boronic acid(1.4 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 27-3> 3.7 g (수율 71%)을 얻었다.(m/z=525)
Intermediate 27-3 was prepared in the same manner as in Example 1 (1), except that phenyl boronic acid (1.4 g, 0.012 mol) was added to Intermediate 27-2 (5.3 g, 0.010 mol) Yield: 71%). (M / z = 525)
(4) (4) 제조예Manufacturing example 4 : 중간체 27-4의 합성 4: Synthesis of intermediate 27-4
중간체 27-3(5.3 g, 0.010 mol)에 3,5-di-tert-butylphenylboronic acid(2.8 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 27-4> 4.7 g (수율 70%)을 얻었다.(m/z=678)
Intermediate 27-3 (5.3 g, 0.010 mol) was synthesized in the same manner as in Example 1 (1) except that 3,5-di-tert-butylphenylboronic acid (2.8 g, 0.012 mol) 27-4> (m / z = 678) (yield: 70%).
(5) (5) 제조예Manufacturing example 5 : 화합물 165의 합성 5: Synthesis of Compound 165
중간체 27-4(6.8 g, 0.010 mol)에 4-bromo-N,N-dip-tolylaniline(3.5 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 165> 1.9 g (수율 54%)을 얻었다.Was synthesized in the same manner as in Example 1 (2) except that 4-bromo-N, N-dip-tolylaniline (3.5 g, 0.010 mol) was added to Intermediate 27-4 (6.8 g, 0.010 mol) Compound 165> 1.9 g (yield: 54%) was obtained.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.49/d, 8.10/d, 7.87/d, 7.62/d, 7.60/s, 7.55/d, 7.38/m, 7.28/m, 6.75/s, 6.58/d) 2H(7.82/d, 7.79/d, 7.51/m, 7.41/m, 7.37/d, 6.63/d, 1.72/s) 3H(2.34/s) 6H(6.98/d, 6.51/d, 1.35/s) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.49 / d, 8.10 / d, 7.87 / d, 7.62 / d, 7.60 / s, 7.55 / d, 7.38 / m, 7.28 / m, 6.75 / s , 6.58 / d) 2H (7.82 / d, 7.79 / d, 7.51 / m, 7.41 / m, 7.37 / d, 6.63 / d, 1.72 / s) , 1.35 / s)
LC/MS: m/z=950[(M+1)+]
LC / MS: m / z = 950 [(M + 1) < + &
실시예Example 28 : 화합물 166의 합성 28: Synthesis of compound 166
(1) (One) 제조예Manufacturing example 1 : 중간체 28-1의 합성 1: Synthesis of intermediate 28-1
3-bromo-2-methyl-1H-indole(2.1 g, 0.010 mol)에 9H-carbazol-3-ylboronic acid(2.5 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 28-1> 2.1 g (수율 70%)을 얻었다.(m/z=296)
3-ylboronic acid (2.5 g, 0.012 mol) was added to 3-bromo-2-methyl-1H-indole (2.1 g, 0.010 mol) To obtain 2.1 g (yield 70%) of Intermediate 28-1 (m / z = 296)
(2) (2) 제조예Manufacturing example 2 : 화합물 166의 합성 2: Synthesis of Compound 166
중간체 28-1(3.0 g, 0.010 mol)에 4-bromo-N,N-dip-tolylaniline(3.5 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 153> 5.1g (수율 61%)을 얻었다.Synthesis was conducted in the same manner as in Example 1 (2) except that 4-bromo-N, N-dip-tolylaniline (3.5 g, 0.010 mol) was added to Intermediate 28-1 (3.0 g, 0.010 mol) 5.1 g (yield: 61%) of Compound 153 was obtained.
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.55/d, 7.94/d, 7.87/d, 7.77/s, 7.70/d, 7.69/d, 7.50/m, 7.42/m, 7.39/d, 7.33/m, 7.25/m, 2.28/s) 4H(7.37/d, 6.63/d, 2.34/s) 8H(6.98/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.55 / d, 7.94 / d, 7.87 / d, 7.77 / s, 7.70 / d, 7.69 / d, 7.50 / m, 7.42 / m, 7.39 / d , 7.33 / m, 7.25 / m, 2.28 / s) 4H (7.37 / d, 6.63 / d, 2.34 / s)
LC/MS: m/z=839[(M+1)+]
LC / MS: m / z = 839 [(M + 1) < + &
실시예Example 29 : 화합물 171의 합성 29: Synthesis of Compound 171
(1) (One) 제조예Manufacturing example 1 : 중간체 29-1의 합성 1: Synthesis of intermediate 29-1
3-bromo-5-chloro-1H-indole(2.3 g, 0.010 mol)에 dip-tolylamine(2.0 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 29-1> 2.6 g (수율 75%)을 얻었다.(m/z=346)
Was synthesized in the same manner as in Example 1 (2) except that dip-tolylamine (2.0 g, 0.010 mol) was added to 3-bromo-5-chloro-1H- indole (2.3 g, 0.010 mol) 29-1> 2.6 g (yield 75%). (M / z = 346)
(2) (2) 제조예Manufacturing example 2 : 중간체 29-2의 합성 2: Synthesis of intermediate 29-2
중간체 29-1(3.5 g, 0.010 mol)에 N-bromosuccinimide(1.8 g, 0.010 mol)를 넣고 실시예 4-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 29-2> 2.6 g (수율 61%)을 얻었다.(m/z=425)
2.6 g (Intermediate 29-2) was synthesized in the same manner as in Example 4 (3) except that N-bromosuccinimide (1.8 g, 0.010 mol) was added to Intermediate 29-1 (3.5 g, 0.010 mol) Yield: 61%). (M / z = 425)
(3) (3) 제조예Manufacturing example 3 : 중간체 29-3의 합성 3: Synthesis of intermediate 29-3
중간체 29-2(4.3 g, 0.010 mol)에 phenyl boronic acid(1.4 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 29-3> 3.0 g (수율 71%)을 얻었다.(m/z=423)
Intermediate 29-3 was synthesized in the same manner as in Example 1 (1) except that phenyl boronic acid (1.4 g, 0.012 mol) was added to Intermediate 29-2 (4.3 g, 0.010 mol) Yield: 71%). (M / z = 423)
(4) (4) 제조예Manufacturing example 4 : 중간체 29-4의 합성 4: Synthesis of intermediate 29-4
중간체 29-3(4.2 g, 0.010 mol)에 bromobenzene(1.6 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 29-4> 3.1 g (수율 61%)을 얻었다.(m/z=500)
3.1 g (yield: 61%) of Intermediate 29-4 (4.2 g, 0.010 mol) was synthesized in the same manner as in Example 1 (2) except that bromobenzene (1.6 g, 0.010 mol) %). (M / z = 500)
(5) (5) 제조예Manufacturing example 5 : 중간체 29-5의 합성 5: Synthesis of intermediate 29-5
9,9-dimethyl-N-(4'-methylbiphenyl-4-yl)-9H-fluoren-2-amine(3.8 g,0.010 mol)에 1,4-dibromobenzene(2.3 g, 0.010 mol)를 넣고 실시예 1-제조예(2)에서 사용된 동일한 방법으로 합성하여 <중간체 29-5> 3.8 g (수율 71%)을 얻었다.(m/z=530)
1,4-dibromobenzene (2.3 g, 0.010 mol) was added to 9,9-dimethyl-N- (4'-methylbiphenyl-4-yl) -9H- fluoren- 1- (m / z = 530) 3.8 g (yield: 71%) of Intermediate 29-5 was obtained by the same method as in the Production Example (2)
(6) (6) 제조예Manufacturing example 6 : 중간체 29-6의 합성 6: Synthesis of intermediate 29-6
중간체 29-5(5.3 g, 0.010 mol)에 bis(pinacolato)dibron(3.0 g, 0.012 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체24-1> 3.9 g (수율 67%)을 얻었다.(m/z=577)
<Intermediate 24-1> 3.9 g (0.09 mol) was added to the intermediate 29-5 (5.3 g, 0.010 mol) and bis (pinacolato) dibron g (yield 67%). (m / z = 577)
(7) (7) 제조예Manufacturing example 7 : 화합물 171의 합성 7: Synthesis of Compound 171
중간체 29-4(5.0 g, 0.010 mol)에 중간체 29-6(6.9 g, 0.012 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <화합물 171> 6.3 g (수율 69%)을 얻었다.The compound 291 (6.9 g, 0.012 mol) was added to Intermediate 29-4 (5.0 g, 0.010 mol) and the compound was used in the same manner as in Example 1 (1) 69%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(8.18/d, 8.00/d, 7.87/d, 7.80/s, 7.62/d, 7.55/d, 7.45/m, 7.41/m, 7.38/m, 7.28/m, 6.75/s, 6.58/d) 2H(7.79/d, 7.58/m, 7.51/m, 7.50/d, 7.33/d, 7.29/d, 1.72/s) 3H(2.34/s) 4H(7.54/d, 6.98/d, 6.69/d, 6.51/d) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (8.18 / d, 8.00 / d, 7.87 / d, 7.80 / s, 7.62 / d, 7.55 / d, 7.45 / m, 7.41 / m, 7.38 / m 7.58 / d), 2H (7.79 / d, 7.58 / m, 7.51 / m, 7.50 / d, 7.33 / d, 7.29 / d, 1.72 / s) (7.54 / d, 6.98 / d, 6.69 / d, 6.51 / d)
LC/MS: m/z=914[(M+1)+]
LC / MS: m / z = 914 [(M + 1) < + &
실시예Example 30 : 화합물 181의 합성 30: Synthesis of Compound 181
(1) (One) 제조예Manufacturing example 1 : 중간체 30-1의 합성 1: Synthesis of intermediate 30-1
중간체 25-2(2.3 g, 0.010 mol)에 bromobenzene(1.6 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <중간체 30-1> 2.1 g (수율 70%)을 얻었다.(m/z=303)
Intermediate 30-1> 2.1 g (Yield: 70%) was synthesized by the same method as in Example 1 (2) except that bromobenzene (1.6 g, 0.010 mol) was added to Intermediate 25-2 %). (M / z = 303)
(2) (2) 제조예Manufacturing example 2 : 중간체 30-2의 합성 2: Synthesis of intermediate 30-2
중간체 30-1(3.0 g, 0.010 mol)에 bis(pinacolato)dibron(3.0 g, 0.012 mol)를 넣고 실시예 5-제조예 (3)에서 사용된 동일한 방법으로 합성하여 <중간체 30-2> 2.4 g (수율 61%)을 얻었다.(m/z=395)
Intermediate 30-2 (2.4 g, 0.012 mol) was synthesized in the same manner as in Example 5 (3), except that bis (pinacolato) dibron (3.0 g, 0.012 mol) g (yield: 61%). (m / z = 395)
(3) (3) 제조예Manufacturing example 3 : 중간체 30-3의 합성 3: Synthesis of intermediate 30-3
중간체 30-2(4.0 g, 0.010 mol)에 1,3-dibromo-5-chlorobenzene(2.2 g, 0.008 mol)를 넣고 실시예 1-제조예 (1)에서 사용된 동일한 방법으로 합성하여 <중간체 30-3> 3.8 g (수율 74%)을 얻었다.(m/z=647)
Synthesis was conducted in the same manner as in Example 1 (1) except that 1,3-dibromo-5-chlorobenzene (2.2 g, 0.008 mol) was added to Intermediate 30-2 (4.0 g, 0.010 mol) -3> 3.8 g (yield: 74%). (M / z = 647)
(4) (4) 제조예Manufacturing example 4 : 화합물 181의 합성 4: Synthesis of Compound 181
중간체 30-3(6.5 g, 0.010 mol)에 9,9-dimethyl-N-(4'-methylbiphenyl-4-yl)-9H-fluoren-2-amine(3.8 g, 0.010 mol)를 넣고 실시예 1-제조예 (2)에서 사용된 동일한 방법으로 합성하여 <화합물 181> 6.3 g (수율 61%)을 얻었다.9-dimethyl-N- (4'-methylbiphenyl-4-yl) -9H-fluoren-2-amine (3.8 g, 0.010 mol) was added to Intermediate 30-3 (6.5 g, 0.010 mol) - The title compound (181) was synthesized according to the same method as that of Production Example (2) to give 6.3 g (Yield 61%).
H-NMR (200MHz, CDCl3):δ ppm, 1H(7.87/d, 7.55/d, 7.38/m, 7.28/m, 7.05/s, 6.75/s, 6.58/d) 2H(8.17/d, 7.71/d, 7.54/d, 7.45/m, 7.38/d, 7.37/d, 6.85/d, 6.69/d, 1.72/s) 3H(1.35/s) 4H(7.79/d, 7.58/d, 7.51/m, 7.50/d, 7.42/m, 7.41/m) H-NMR (200MHz, CDCl 3 ): δ ppm, 1H (7.87 / d, 7.55 / d, 7.38 / m, 7.28 / m, 7.05 / s, 6.75 / s, 6.58 / d) 2H (8.17 / d, 7.71 7.58 / d, 7.37 / d, 6.85 / d, 6.69 / d, 1.72 / s) , 7.50 / d, 7.42 / m, 7.41 / m)
LC/MS: m/z=1028[(M+1)+]
LC / MS: m / z = 1028 [(M + 1) < + &
소자 device
실시예Example
1 : 화합물 1을 1:
ITO로 코팅된 유리기판 위에 <화합물 1>을 증착하여 120 nm의 정공수송층을 형성하였으며, 이어서 Ir(ppy)3을 도펀트로 하여 CBP를 호스트로 하여 증착속도를 0.1nm/sec, Ir(ppy)3 증착속도를 0.009nm/sec로 증착하고, 증착속도 비율이 9%가 되도록 Ir(ppy)3을 도핑하여 정공수송층 상에 발광층을 30 nm 두께로 형성하였다.Compound (1) was deposited on a glass substrate coated with ITO to form a hole transport layer having a thickness of 120 nm. Ir (ppy) 3 was used as a dopant, CBP was used as a host and the deposition rate was set to 0.1 nm / 3 was deposited at a deposition rate of 0.009 nm / sec, and Ir (ppy) 3 was doped so as to have a deposition rate ratio of 9% to form a light emitting layer with a thickness of 30 nm on the hole transport layer.
그 위에 Balq를 10 nm 두께로 증착하여 정공이 발광층을 지나 전자수송층으로 이동하는 것을 방지하는 정공차단층을 형성하고, 그 위에 Alq3를 증착하여 40 nm의 전자수송층을 형성하였으며, 그 위에 불화리튬을 증착하여 1 nm의 전자주입층을 형성하였다. 전자주입층 상에 알루미늄을 증착하여 120 nm의 음극을 형성하여 유기전계발광소자를 제조하였다.Balq was deposited thereon to a thickness of 10 nm to form a hole blocking layer for preventing holes from moving to the electron transporting layer through the light emitting layer, and Alq 3 was deposited thereon to form an electron transporting layer of 40 nm. Lithium fluoride To form a 1 nm electron injection layer. Aluminum was deposited on the electron injection layer to form a 120 nm negative electrode, thereby fabricating an organic electroluminescent device.
이때, 각 물질의 증착속도는 유기물질인, 화합물 1, CBP, Alq3, Balq는 0.1 nm/sec, 불화리튬은 0.01 nm/sec, 알루미늄은 0.5 nm/sec로 하였다.
At this time, the deposition rate of each material was set to 0.1 nm / sec for
소자 device 실시예Example 2 내지 30 2 to 30
상기 화합물 1 대신 하기 [표 1]에 기재된 화합물을 사용한 것을 제외하고는 소자 실시예 1과 동일한 방법으로 소자 실시예 2 내지 30의 유기전계발광소자를 제조하였다.
An organic electroluminescent device of each of the
소자 device 비교예Comparative Example 1 One
비교예를 위한 유기발광다이오드 소자는 상기 실시예의 소자구조에서 발명에 의해 제조된 화합물 대신 일반적으로 정공수송물질로 많이 사용되고 있는 NPB를 사용한 점을 제외하고 동일하게 제작하였으며 상기 Ir(ppy)3 ,CBP,NPB의 구조는 아래와 같다.The organic light emitting diode device for the comparative example was fabricated in the same manner except that NPB, which is generally used as a hole transporting material, was used instead of the compound manufactured by the invention in the device structure of the embodiment, and Ir (ppy) 3 , CBP , The structure of NPB is as follows.
(1000 cd/㎡)The driving voltage (V)
(1000 cd / m 2)
(cd/A)Luminous efficiency
(cd / A)
구동전압 및 발광효율 측정Measurement of driving voltage and luminous efficiency
상기 유기발광소자(기판크기 : 25 × 25 ㎟ / 증착면적 : 2 × 2 ㎟)를 IVL 측정셋트(CS-2000+지그+IVL프로그램)에 고정한 후 전류를 1 mA/㎡씩 상승시키며 증착면의 발광 휘도(cd/㎡), 구동전압(V), 발광효율(cd/A)을 측정하여 휘도가 1000 cd/㎡일 때 구동전압과 발광효율을 상기 [표 1]에 나타내었다.After fixing the organic light emitting device (substrate size: 25 × 25
상기 실시예와 비교예 및 [표 1]의 결과로부터, 본 발명에 따른 [화학식 1]로 표시되는 화합물은 정공수송물질로 사용되는 NPB에 비해 구동전압 및 발광효율 등이 우수한 특성을 보이므로, 표시소자, 디스플레이 소자 및 조명 등에 유용하게 사용될 수 있음을 알 수 있다.From the results of the above Examples, Comparative Examples and Table 1, it can be seen that the compound represented by
Claims (6)
[화학식 1]
상기 [화학식 1]에서,
Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 인덴일기 및 치환 또는 비치환된 플루오렌일기 중에서 선택되는 어느 하나이고,
상기 Ar1 내지 Ar4가 치환된 페닐기, 치환된 인덴일기 및 치환된 플루오렌일기 중에서 선택되는 경우 각각 탄소수 1 내지 3의 알킬기로 치환된 것이며,
L은 연결기로서, 단결합 또는 페닐렌기이고,
X 및 Y는 각각 단결합 또는 하기 [구조식 1] 중에서 선택되는 어느 하나이며(상기 X 및 Y가 모두 단결합인 경우는 제외함),
[구조식 1]
상기 [구조식 1]에서,
'*'은 상기 X 및 Y의 2가 연결기 결합하는 위치이고, R은 수소, 페닐기, 탄소수 1 내지 3의 알킬기 및 탄소수 1 내지 3의 알킬기로 치환된 페닐기 중에서 선택되는 어느 하나이다.An organic light-emitting compound represented by the following Formula 1:
[Chemical Formula 1]
In the above formula (1)
Ar 1 to Ar 4 are the same or different from each other and each independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted indenyl group and a substituted or unsubstituted fluorenyl group,
When Ar 1 to Ar 4 are selected from the group consisting of a substituted phenyl group, a substituted indanyl group and a substituted fluorenyl group, they are each substituted with an alkyl group having 1 to 3 carbon atoms,
L is a linking group, a single bond or a phenylene group,
X and Y are each a single bond or any one selected from the following [formula 1] (except when X and Y are both a single bond),
[Structural formula 1]
In the above formula 1,
'*' Is a position at which a divalent linking group of X and Y is bonded, and R is any one selected from hydrogen, a phenyl group, an alkyl group having 1 to 3 carbon atoms, and a phenyl group substituted with an alkyl group having 1 to 3 carbon atoms.
상기 유기물층 중 1 층 이상은 청구항 1항에 따른 [화학식 1]로 구현되는 유기발광 화합물을 하나 이상 포함하는 것을 특징으로 하는 유기전계발광소자.1. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode,
Wherein at least one of the organic material layers comprises at least one organic light emitting compound represented by Formula 1 according to Claim 1.
상기 유기물층은 정공 주입층, 정공 수송층, 및 정공 주입 및 정공 수송을 동시에 하는 층 중 1층 이상을 포함하고, 상기 층들 중 1층 이상이 상기 [화학식 1]로 표시되는 유기발광 화합물을 포함하는 것을 특징으로 하는 유기전계발광소자.The method of claim 3,
Wherein the organic material layer includes at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, wherein at least one of the layers includes an organic light emitting compound represented by Formula 1 Wherein the organic electroluminescent device comprises:
상기 [화학식 1]로 표시되는 유기발광 화합물은 상기 정공 주입층 또는 정공 수송층에 포함되는 것을 특징으로 하는 유기전계발광소자.5. The method of claim 4,
Wherein the organic light emitting compound represented by Formula 1 is contained in the hole injecting layer or the hole transporting layer.
상기 유기물층에 적색, 녹색 또는 청색 발광을 하는 유기 발광층을 하나 이상을 더 포함하여 백색 발광을 하는 것을 특징으로 하는 유기전계발광소자.The method of claim 3,
Wherein at least one of the organic light emitting layers emitting red, green or blue light is further included in the organic material layer to emit white light.
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