KR20060044424A - 새로운 정공 주입 또는 수송용 물질 및 이를 이용한 유기발광 소자 - Google Patents
새로운 정공 주입 또는 수송용 물질 및 이를 이용한 유기발광 소자 Download PDFInfo
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- KR20060044424A KR20060044424A KR1020050022762A KR20050022762A KR20060044424A KR 20060044424 A KR20060044424 A KR 20060044424A KR 1020050022762 A KR1020050022762 A KR 1020050022762A KR 20050022762 A KR20050022762 A KR 20050022762A KR 20060044424 A KR20060044424 A KR 20060044424A
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- 239000000463 material Substances 0.000 title description 65
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- 150000001875 compounds Chemical class 0.000 claims abstract description 159
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- 239000007924 injection Substances 0.000 claims abstract description 42
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- 239000000126 substance Substances 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 29
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- -1 heteroaromatic hydrocarbons Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract description 8
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 12
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 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 9
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- QPTWWBLGJZWRAV-UHFFFAOYSA-N 2,7-dibromo-9h-carbazole Chemical compound BrC1=CC=C2C3=CC=C(Br)C=C3NC2=C1 QPTWWBLGJZWRAV-UHFFFAOYSA-N 0.000 description 3
- TWPMMLHBHPYSMT-UHFFFAOYSA-N 3-methyl-n-phenylaniline Chemical compound CC1=CC=CC(NC=2C=CC=CC=2)=C1 TWPMMLHBHPYSMT-UHFFFAOYSA-N 0.000 description 3
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
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- FIHILUSWISKVSR-UHFFFAOYSA-N 3,6-dibromo-9h-carbazole Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3NC2=C1 FIHILUSWISKVSR-UHFFFAOYSA-N 0.000 description 2
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- 238000000576 coating method Methods 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
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- RQIAICDOHSGNLG-UHFFFAOYSA-N n-(3-methylphenyl)naphthalen-2-amine Chemical compound CC1=CC=CC(NC=2C=C3C=CC=CC3=CC=2)=C1 RQIAICDOHSGNLG-UHFFFAOYSA-N 0.000 description 2
- ABMCIJZTMPDEGW-UHFFFAOYSA-N n-(4-bromophenyl)-n-phenylnaphthalen-1-amine Chemical compound C1=CC(Br)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ABMCIJZTMPDEGW-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
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- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
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- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 1
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ITHJVESPIWLLBQ-UHFFFAOYSA-N C1(=CC=CC=C1)C(=CC1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=C(C=CC=C1)C=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(=CC1=C(C=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC=12)C1=C(C=CC=C1)C=C(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 ITHJVESPIWLLBQ-UHFFFAOYSA-N 0.000 description 1
- 0 CN(*)c(cc1)ccc1-[n]1c(ccc([Al]N(*)*)c2)c2c2c1ccc([Al]N(*)*)c2 Chemical compound CN(*)c(cc1)ccc1-[n]1c(ccc([Al]N(*)*)c2)c2c2c1ccc([Al]N(*)*)c2 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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Abstract
Description
Claims (11)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 식 중, R1 내지 R10는 서로 동일하거나 상이하며 각각, 수소원자; 탄소수 1-20의 지방족 탄화수소; 방향족 탄화 수소, 또는 니트로, 니트릴기, 할로겐, 알킬기, 알콕시기 또는 아미노기로 치환된 방향족 탄화수소; 방향족 치환체를 갖는 실리콘기; 헤테로고리 방향족 탄화수소, 또는 니트로, 니트릴기, 할로겐, 알킬기, 알콕시기 또는 아미노기로 치환된 헤테로고리 방향족 탄화수소; 탄소수 1-20의 탄화수소 또는 탄소수 6-24의 방향족 탄화수소로 치환된 티오펜기; 또는 방향족 탄화수소로 치환된 붕소기;로 이루어진 군에서 선택된 1종 이상을 1회 또는 2회 이상 반복하여 포함하며,상기 Ar은 방향족 탄화수소 또는 니트로, 니트릴기, 할로겐, 알킬기, 알콕시기 또는 아미노기로 치환된 방향족 탄화수소이며,상기 식 중에서 l, m, n 각각 1 이상의 정수이고, o는 0 이상의 정수이며,여기서, R1, R2, R3, R4, R5 및 R6가 동시에 수소 원자이면서 D도 H인 경우는 제외된다.
- 제 1항에 있어서, 상기 상기 방향족 탄화수소는 페닐, 비페닐, 터페닐, 나프틸, 안트라세닐, 페난트렌, 파이레닐 및 페릴레닐을 포함하는 것을 특징으로 하는 화합물.
- 제 1항에 있어서, 상기 헤테로 방향족탄화수소는 티오펜, 퓨란, 피롤, 이미다졸, 티아졸, 옥사졸, 옥사디아졸, 티아디아졸, 트리아졸, 피리딜, 피리다질, 피라진, 퀴놀린 및 이소퀴놀린을 포함하는 것을 특징으로 하는 화합물.
- 제 1 전극, 제 2 전극 및 상기 두 전극 사이에 위치하는 하나 이상의 유기화합물층을 구비하는 유기 발광 소자에 있어서,상기 유기화합물 층 중 적어도 하나의 유기화합물층에는 제 1항 내지 제 6항 중 어느 한 항에 의한 화합물이 1 종 이상 함유되어 있는 것을 특징으로 하는 유기 발광 소자.
- 제 7항에 있어서, 상기 제 1항 내지 제 6항 중 어느 한 항에 의한 화합물이 1 종 이상 함유되어 있는 유기화합물층은 정공 주입 및 수송 기능을 가지는 정공 주입 및 수송 층인 것을 특징으로 하는 유기 발광 소자.
- 제 7항에 있어서, 제 1항 내지 제 6항 중 어느 한 항에 의한 화합물이 1 종 이상 함유되어 있는 유기화합물층은 정공 주입, 정공 수송 및 발광 기능을 가지는 정공 주입, 수송 및 발광 층인 것을 특징으로 하는 유기 발광 소자.
- 제 7항에 있어서, 제 1항 내지 제 6항 중 어느 한 항에 의한 화합물이 1 종 이상 함유되어 있는 유기화합물층은 정공 주입 기능을 가지는 정공 주입층인 것을 특징으로 하는 유기 발광 소자.
- 제 7항에 있어서, 상기 유기 발광 소자가 아래로부터 기판, 양극, 정공주입층, 정공수송층, 유기발광층, 전자수송층, 및 음극을 포함하며, 제 1항 내지 제 6항 중 어느 한 항에 의한 화합물이 1 종 이상 함유되어 있는 유기화합물층은 상기 정공 주입층, 정공 수송층 및 발광층 중에서 선택된 적어도 한 층인 것을 특징으로 하는 유기 발광 소자.
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JP2003075955A (ja) * | 2001-09-03 | 2003-03-12 | Konica Corp | 銀色調を改良した光熱写真画像形成材料 |
DE10203328A1 (de) * | 2002-01-28 | 2003-08-07 | Syntec Ges Fuer Chemie Und Tec | Neue Triarylamin-Derivate mit raumfüllenden Flügelgruppen und ihre Einsatz in elektro-fotografischen und organischen elektrolumineszenten Vorrichtungen |
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US20030205696A1 (en) | 2002-04-25 | 2003-11-06 | Canon Kabushiki Kaisha | Carbazole-based materials for guest-host electroluminescent systems |
US20040001969A1 (en) * | 2002-06-27 | 2004-01-01 | Eastman Kodak Company | Device containing green organic light-emitting diode |
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CN102153502B (zh) * | 2004-10-19 | 2012-12-26 | 株式会社半导体能源研究所 | 咔唑衍生物和使用该咔唑衍生物的发光元件以及发光器件 |
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2005
- 2005-03-18 EP EP05733437.7A patent/EP1725632B1/en active Active
- 2005-03-18 KR KR1020050022762A patent/KR100664390B1/ko active IP Right Grant
- 2005-03-18 WO PCT/KR2005/000794 patent/WO2005090512A1/en not_active Application Discontinuation
- 2005-03-18 US US11/083,360 patent/US8198801B2/en active Active
- 2005-03-18 JP JP2006546860A patent/JP5242917B2/ja active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2014021569A1 (en) * | 2012-08-01 | 2014-02-06 | Sk Chemicals Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device including the same |
KR20170035344A (ko) | 2015-09-22 | 2017-03-30 | 주식회사 엘지화학 | 신규 화합물 및 이를 포함하는 유기 발광 소자 |
Also Published As
Publication number | Publication date |
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JP2007520470A (ja) | 2007-07-26 |
EP1725632B1 (en) | 2014-04-30 |
US8198801B2 (en) | 2012-06-12 |
KR100664390B1 (ko) | 2007-01-02 |
EP1725632A1 (en) | 2006-11-29 |
EP1725632A4 (en) | 2009-05-06 |
US20050225235A1 (en) | 2005-10-13 |
JP5242917B2 (ja) | 2013-07-24 |
WO2005090512A1 (en) | 2005-09-29 |
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