KR20060042243A - 유기 금속 착체, 발광성 고체, 유기 전기발광 소자 및 유기전기발광 디스플레이 - Google Patents
유기 금속 착체, 발광성 고체, 유기 전기발광 소자 및 유기전기발광 디스플레이 Download PDFInfo
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- KR20060042243A KR20060042243A KR1020050015863A KR20050015863A KR20060042243A KR 20060042243 A KR20060042243 A KR 20060042243A KR 1020050015863 A KR1020050015863 A KR 1020050015863A KR 20050015863 A KR20050015863 A KR 20050015863A KR 20060042243 A KR20060042243 A KR 20060042243A
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- 239000002184 metal Substances 0.000 claims abstract description 77
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 36
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- 125000003118 aryl group Chemical group 0.000 claims description 22
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- 125000004104 aryloxy group Chemical group 0.000 claims description 6
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
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- 239000000178 monomer Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N nickel(II) oxide Inorganic materials [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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- 239000013034 phenoxy resin Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical group 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- NVMNEWNGLGACBB-UHFFFAOYSA-N sodium;1,2-diaza-4-azanidacyclopenta-2,5-diene Chemical compound [Na+].C=1N=C[N-]N=1 NVMNEWNGLGACBB-UHFFFAOYSA-N 0.000 description 1
- QAJGUMORHHJFNJ-UHFFFAOYSA-M sodium;phenoxide;trihydrate Chemical compound O.O.O.[Na+].[O-]C1=CC=CC=C1 QAJGUMORHHJFNJ-UHFFFAOYSA-M 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- HGWXMLVVADNJMQ-UHFFFAOYSA-N tributyl(1h-isoquinolin-2-yl)stannane Chemical compound C1=CC=C2C=CN([Sn](CCCC)(CCCC)CCCC)CC2=C1 HGWXMLVVADNJMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
배위자 | dpt | dpb | diqt | tp | dpzb |
o2Fph | 합성예 1 | 합성예 7 | 합성예 13 | 합성예 19 | 합성예 25 |
odmp | 합성예 2 | 합성예 8 | 합성예 14 | 합성예 20 | 합성예 26 |
o2pph | 합성예 3 | 합성예 9 | 합성예 15 | 합성예 21 | 합성예 27 |
o26dpph | 합성예 4 | 합성예 10 | 합성예 16 | 합성예 22 | 합성예 28 |
dmpr | 합성예 5 | 합성예 11 | 합성예 17 | 합성예 23 | 합성예 29 |
mbtaz | 합성예 6 | 합성예 12 | 합성예 18 | 합성예 24 | 합성예 30 |
Claims (11)
- 금속 원자,상기 금속 원자에 대해, 질소 원자 2개 및 탄소 원자 1개를 개재하여 삼좌로 결합되고, 상기 질소 원자 2개 사이에 상기 탄소 원자가 위치하는 삼좌 배위자, 및상기 금속 원자에 대해, N 원자, O 원자 및 S 원자로부터 선택되는 하나의 원자를 개재하여 일좌로 결합되고, 상기 금속 원자에 대해 결합된 위치로부터 가장 떨어진 위치를 제외한 위치에 치환기를 갖는 환구조를 포함하는 일좌 배위자를 갖는 것을 특징으로 하는 유기 금속 착체.
- 제1항에 있어서, 치환기가 알킬기 및 아릴기로부터 선택되는 것인 유기 금속 착체.
- 금속 원자,상기 금속 원자에 대해, 질소 원자 2개 및 탄소 원자 1개를 개재하여 삼좌로 결합되고, 상기 질소 원자 2개 사이에 상기 탄소 원자가 위치하는 삼좌 배위자, 및상기 금속 원자에 대해, N 원자, O 원자 및 S 원자로부터 선택되는 하나의 원자를 개재하여 일좌로 결합되고, 할로겐 원자가 치환된 환구조를 포함하는 일좌 배위자를 갖는 것을 특징으로 하는 유기 금속 착체.
- 제3항에 있어서, 할로겐 원자가 플루오르 원자인 유기 금속 착체.
- 제1항에 있어서, 하기 화학식 1로 표시되는 유기 금속 착체.<화학식 1>식 중,M은 금속 원자를 나타내고,Ar1, Ar2 및 Ar3는 환구조를 나타내고, 모두 상기 M에 결합되며, 상기 Ar1과 상기 Ar2가 결합되고, 상기 Ar2와 상기 Ar3가 결합되어, 전체적으로 상기 M에 삼좌로 결합된 삼좌 배위자를 형성하며,Ar1에 있어서 N은 상기 Ar1으로 표시되는 환구조를 구성하는 질소 원자를 나타내고, Ar2에 있어서 C는 상기 Ar2로 표시되는 환구조를 구성하는 탄소 원자를 나타내며, Ar3에 있어서 N은 상기 Ar3로 표시되는 환구조를 구성하는 질소 원자를 나타내며,R1, R2 및 R3는 서로 동일하거나 상이할 수 있으며, 각각 수소 원자 또는 치환기를 나타내고, 복수일 수 있고, 서로 인접하는 것이 결합하여 환구조를 형성할 수 있고,L은 N 원자, O 원자 및 S 원자로부터 선택되는 하나의 원자를 개재하여 상기 M에 대해 일좌로 결합되고, 환구조를 포함하는 일좌 배위자를 나타내며,R4는 상기 L에 있어서 상기 M에 대해 결합되는 위치로부터 가장 떨어진 위치를 제외한 위치에 치환된 치환기를 나타낸다.
- 제3항에 있어서, 하기 화학식 2로 표시되는 유기 금속 착체.<화학식 2>식 중,M은 금속 원자를 나타내고,Ar1, Ar2 및 Ar3는 환구조를 나타내고, 모두 상기 M에 결합되며, 상기 Ar1과 상기 Ar2가 결합되고, 상기 Ar2와 상기 Ar3가 결합되어, 전체적으로 상기 M에 삼좌로 결합된 삼좌 배위자를 형성하며,Ar1에 있어서 N은 상기 Ar1으로 표시되는 환구조를 구성하는 질소 원자를 나타내고, Ar2에 있어서 C는 상기 Ar2로 표시되는 환구조를 구성하는 탄소 원자를 나 타내며, Ar3에 있어서 N은 상기 Ar3로 표시되는 환구조를 구성하는 질소 원자를 나타내며,R1, R2 및 R3는 서로 동일하거나 상이할 수 있으며, 각각 수소 원자 또는 치환기를 나타내고, 복수일 수 있고, 서로 인접하는 것이 결합하여 환구조를 형성할 수 있으며,L은 N 원자, O 원자 및 S 원자로부터 선택되는 하나의 원자를 개재하여 상기 M에 대해 일좌로 결합되고, 환구조를 포함하는 일좌 배위자를 나타내며,X는 할로겐 원자를 나타낸다.
- 제1항 내지 제6항 중 어느 한 항에 기재된 유기 금속 착체를 함유하는 것을 특징으로 하는 발광성 고체.
- 정극 및 부극 사이에 유기 박막층을 가지며, 상기 유기 박막층이 제1항 내지 제6항 중 어느 한 항에 기재된 유기 금속 착체를 함유하는 것을 특징으로 하는 유기 전기발광(EL) 소자.
- 제8항에 있어서, 발광층이 하기 화학식 4로 표시되는 카르바졸 유도체를 함유하는 유기 EL 소자.<화학식 4>식 중,Ar은 방향족환을 포함하는 2가 또는 3가의 기, 또는 복소환식 방향족환을 포함하는 2가 또는 3가의 기를 나타내고,R9 및 R10은 각각 독립적으로 수소 원자, 할로겐 원자, 알킬기, 아르알킬기, 알케닐기, 아릴기, 시아노기, 아미노기, 아실기, 알콕시카르보닐기, 카르복실기, 알콕시기, 알킬술포닐기, 수산기, 아미드기, 아릴옥시기, 방향족 탄화수소환기 또는 방향족 복소환기를 나타내고, 이들은 치환기로 더 치환될 수 있으며,n은 2 또는 3의 정수를 나타낸다.
- 제8항에 기재된 유기 EL 소자를 사용한 것을 특징으로 하는 유기 EL 디스플레이.
- 제9항에 기재된 유기 EL 소자를 사용한 것을 특징으로 하는 유기 EL 디스플레이.
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JP2006182921A (ja) * | 2004-12-28 | 2006-07-13 | Konica Minolta Holdings Inc | 有機el素子用材料、有機el素子、表示装置及び照明装置 |
JP4786917B2 (ja) * | 2005-03-17 | 2011-10-05 | 富士フイルム株式会社 | 有機金属錯体、発光性固体、有機el素子及び有機elディスプレイ |
JPWO2006100888A1 (ja) * | 2005-03-22 | 2008-08-28 | コニカミノルタホールディングス株式会社 | 有機el素子用材料、有機el素子、表示装置及び照明装置 |
KR20080037006A (ko) * | 2005-08-05 | 2008-04-29 | 이데미쓰 고산 가부시키가이샤 | 전이금속 착체화합물 및 그것을 이용한 유기 전기발광 소자 |
ITBO20050722A1 (it) * | 2005-11-28 | 2007-05-29 | Consiglio Nazionale Ricerche | Dispositivo elettroluminescente organico |
US8106199B2 (en) * | 2007-02-13 | 2012-01-31 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Organometallic materials for optical emission, optical absorption, and devices including organometallic materials |
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JP5691826B2 (ja) * | 2011-05-17 | 2015-04-01 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、照明装置および表示装置 |
US20140203270A1 (en) | 2011-09-12 | 2014-07-24 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element material having silicon-containing four membered ring structure, and organic electroluminescent element |
WO2013038843A1 (ja) | 2011-09-12 | 2013-03-21 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
US9466802B2 (en) | 2011-09-12 | 2016-10-11 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
JP6006732B2 (ja) | 2011-12-12 | 2016-10-12 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及びそれを用いた有機電界発光素子 |
US9985219B2 (en) | 2012-03-12 | 2018-05-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
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US9502671B2 (en) | 2014-07-28 | 2016-11-22 | Arizona Board Of Regents On Behalf Of Arizona State University | Tridentate cyclometalated metal complexes with six-membered coordination rings |
US9818959B2 (en) | 2014-07-29 | 2017-11-14 | Arizona Board of Regents on behlaf of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
US9865825B2 (en) | 2014-11-10 | 2018-01-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
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