KR100988004B1 - 안정성 유기 발광 장치 물질 및 안정성이 개선된 장치 - Google Patents
안정성 유기 발광 장치 물질 및 안정성이 개선된 장치 Download PDFInfo
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- KR100988004B1 KR100988004B1 KR1020077025733A KR20077025733A KR100988004B1 KR 100988004 B1 KR100988004 B1 KR 100988004B1 KR 1020077025733 A KR1020077025733 A KR 1020077025733A KR 20077025733 A KR20077025733 A KR 20077025733A KR 100988004 B1 KR100988004 B1 KR 100988004B1
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- 239000000463 material Substances 0.000 title abstract description 136
- 150000001875 compounds Chemical class 0.000 claims abstract description 293
- 239000003446 ligand Substances 0.000 claims abstract description 161
- 229910052751 metal Inorganic materials 0.000 claims abstract description 118
- 239000002184 metal Substances 0.000 claims abstract description 113
- 125000003118 aryl group Chemical group 0.000 claims abstract description 78
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 72
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
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- 150000004696 coordination complex Chemical class 0.000 claims description 35
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- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 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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- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
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- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 1
- ODWVPMLEOBRBRY-UHFFFAOYSA-K trichloroiridium hexahydrate Chemical compound O.O.O.O.O.O.[Ir](Cl)(Cl)Cl ODWVPMLEOBRBRY-UHFFFAOYSA-K 0.000 description 1
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Abstract
Description
Claims (180)
- 인광성 화합물로서,인광성 화합물은 한 자리, 두 자리, 세 자리, 네 자리, 다섯 자리 또는 여섯 자리 리간드의 중성 금속 착물이고;리간드는 금속에 직접 결합된 적어도 하나의 제1 아릴 또는 헤테로아릴 환을 포함하며;제1 환은 금속에 직접 결합되지 않고 두 오르토 위치에서 아릴 및 헤테로아릴 기로 구성된 군 중에서 독립적으로 선택된 치환체에 의해 치환된 제2 아릴 또는 헤테로아릴 환에 의해 치환되고;금속 착물은 유기 금속 착물이고;금속은 40 초과의 원자 번호를 지닌 비방사성 금속으로 구성된 군 중에서 선택되는 것인 인광성 화합물.
- 제1항에 있어서, 금속은 Re, Ru, Os, Rh, Ir, Pd, Pt 및 Au로 구성된 군 중에서 선택되는 것인 화합물.
- 제2항에 있어서, 금속은 Os, Ir 및 Pt로 구성된 군 중에서 선택되는 것인 화합물.
- 제3항에 있어서, 금속이 Ir인 화합물.
- 제1항에 있어서, 제2 환은 하나 이상의 아릴, 헤테로아릴 또는 전자 끄는 기에 의해 추가로 치환되는 것인 화합물.
- 제5항에 있어서, 제2 환은 트리페닐렌 기에 의해 치환되는 것인 화합물.
- 제5항에 있어서, 제2 환은 카바졸을 포함하는 기에 의해 치환되는 것인 화합물.
- 제1항에 있어서, 제2 환의 오르토 위치에 있는 치환체가 디아릴아미노아릴 기인 화합물.
- 제1항에 있어서, 480 nm 미만의 파장에서 인광 방출 스펙트럼에서의 최고 에너지 피크를 갖는 화합물.
- 제1항에 있어서, 동종리간드성 화합물인 화합물.
- 제1항에 있어서, 이종리간드성 화합물인 화합물.
- 제1항에 있어서, 승화성 화합물인 화합물.
- 제1항에 있어서, 제2 환은 제1 환의 질소 원자에 부착되는 것인 화합물.
- 제1항에 있어서, 제1 환이 이미다졸 환인 화합물.
- 제1항에 있어서, 제1 환이 피라졸 환인 화합물.
- 제1항에 있어서, 제1 환이 트리아졸 환인 화합물.
- 제1항에 있어서, 제1 환이 피리딘 환인 화합물.
- 제1항에 있어서, 제1 환이 벤젠 환인 화합물.
- 제1항에 있어서, 제1 환은 금속에 또한 직접 결합된 제3 아릴 또는 헤테로아릴 환에 의해 치환되는 것인 화합물.
- 제19항에 있어서, 제1 및 제3 환은 공동으로 단일음이온성 두 자리 리간드를 포함하는 것인 화합물.
- 제19항에 있어서, 제3 환은 페닐, 피리딜, 티오페닐, 푸라닐, 피롤릴, 트리아졸릴 및 피리미딜로 구성된 군 중에서 선택되는 것인 화합물.
- 제19항에 있어서, 제3 환이 하나 또는 둘의 플루오로 기에 의해 치환된 페닐 환인 화합물.
- 제19항에 있어서, 제1 및 제3 환은 단일음이온성 세 자리 리간드내에 포함되는 것인 화합물.
- 제19항에 있어서, 제1 및 제3 환은 공동으로 중성 두 자리 리간드를 포함하는 것인 화합물.
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- 제1항에 있어서, 제1 환은 하기 f5 내지 f9 중에서 선택되는 것인 화합물:상기 식에서,Arsr은 제2 환이고;R1a-c는 각각 수소, 히드로카빌, 이종원자 치환된 히드로카빌, 시아노 및 F로 구성되는 군 중에서 독립적으로 선택되고, 또한, R1a-c 중 임의의 두 개는 연결되어 환을 형성할 수 있으며;f5, f6, f8 및 f9의 경우, R2a는 제1 환 상의 치환체로서 제3 환이고, 상기 제3 환은 금속에 직접 결합된 아릴 또는 헤테로아릴 환이며;f7의 경우, R2b는 제1 환 상의 치환체로서 제3 환이고, 상기 제3 환은 금속에 직접 결합된 아릴 또는 헤테로아릴 환이며, R2a는 수소, 히드로카빌, 이종원자 치환된 히드로카빌, 시아노 및 F로 구성되는 군 중에서 독립적으로 선택된다.
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- 제1항에 있어서, 금속 착물은 두 자리 단일음이온성 N,N-도너 리간드를 포함하는 것인 화합물.
- 제1항에 있어서, 금속 착물은 카벤 도너를 포함하는 것인 화합물.
- 제32항에 있어서, 카벤 도너가 두 자리 단일음이온성 리간드의 일부인 화합물.
- 제1항에 있어서, 제2 환은 플루오라이드 이외의 기에 의해 치환되는 것인 화합물.
- 제1항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 삼중항 에너지가 2.5 eV 초과인 화합물.
- 제1항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 230 g/mol 초과인 화합물.
- 청구항 37은(는) 설정등록료 납부시 포기되었습니다.제1항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 430 g/mol 초과인 화합물.
- 청구항 38은(는) 설정등록료 납부시 포기되었습니다.제1항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 530 g/mol 초과인 화합물.
- 제1항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 750 g/mol 초과인 화합물.
- 제1항에 있어서, 산정된 단일항-삼중항 갭이 0.4 eV 미만인 화합물.
- 청구항 41은(는) 설정등록료 납부시 포기되었습니다.제1항에 있어서, 산정된 단일항-삼중항 갭이 0.3 eV 미만인 화합물.
- 제1항에 있어서, 산정된 단일항-삼중항 갭이 0.2 eV 미만인 화합물.
- 청구항 43은(는) 설정등록료 납부시 포기되었습니다.제1항에 있어서, 산정된 단일항-삼중항 갭이 0.1 eV 미만인 화합물.
- 제1항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.1 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 45은(는) 설정등록료 납부시 포기되었습니다.제1항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.2 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 제1항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.3 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 47은(는) 설정등록료 납부시 포기되었습니다.제1항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.4 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 제1항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.5 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 제1항에 있어서, 하기 수학식에 의해 산정되는 경우, 델타 E가 0.6 eV 미만인 화합물:델타 E = (삼중항 에너지) - (변형 전기화학적 갭);상기 식에서,삼중항 에너지는 상기 금속 착물의 인광 방출 스펙트럼에서 최고 에너지 피크의 에너지(eV)이며;변형 전기화학적 갭은 금속 착물의 산화 전위와 리간드에 상응하는 중성 화합물의 환원 전위 간의 차이를 나타낸다.
- 청구항 50은(는) 설정등록료 납부시 포기되었습니다.제49항에 있어서, 델타 E가 0.5 eV 미만인 화합물.
- 제49항에 있어서, 델타 E가 0.4 eV 미만인 화합물.
- 청구항 52은(는) 설정등록료 납부시 포기되었습니다.제49항에 있어서, 델타 E가 0.3 eV 미만인 화합물.
- 제49항에 있어서, 델타 E가 0.2 eV 미만인 화합물.
- 애노드; 캐소드; 및 방출층을 포함하는 유기 발광 장치로서,방출층은 애노드와 캐소드 사이에 위치하고, 방출층은 제1항에 따른 인광성 화합물을 포함하는 것인 유기 발광 장치.
- 인광성 화합물로서,인광성 화합물은 한 자리, 두 자리, 세 자리, 네 자리, 다섯 자리 또는 여섯 자리 리간드의 중성 금속 착물이고;리간드는 금속에 직접 결합된 적어도 하나의 제1 아릴 또는 헤테로아릴 환을 포함하며;제1 환은 금속에 직접 결합되지 않고 두 오르토 위치에서 H 또는 할라이드 이외의 기에 의해 치환된 제2 아릴 또는 헤테로아릴 환에 의해 치환되며;제1 환은 이미다졸, 벤젠, 나프탈렌, 퀴놀린, 이소퀴놀린, 피리딘, 피리미딘, 피리다진, 피롤, 옥사졸, 티아졸, 옥사디아졸, 티아디아졸, 푸란 또는 티오펜 환이고;금속 착물은 유기 금속 착물이며;금속은 40 초과의 원자 번호를 지닌 비방사성 금속으로 구성된 군 중에서 선택되는 것인 인광성 화합물.
- 제55항에 있어서, 제1 환이 제1 질소를 통해 금속에 배위된 이미다졸인 화합물.
- 제56항에 있어서, 제2 환은 제1 환의 제2 질소에 부착되는 것인 화합물.
- 제55항에 있어서, 금속은 Re, Ru, Os, Rh, Ir, Pd, Pt 및 Au로 구성된 군 중에서 선택되는 것인 화합물.
- 제58항에 있어서, 금속은 Os, Ir 및 Pt로 구성된 군 중에서 선택되는 것인 화합물.
- 제59항에 있어서, 금속이 Ir인 화합물.
- 제55항에 있어서, 제2 환은 하나 이상의 아릴, 헤테로아릴 또는 전자 끄는 기에 의해 치환되는 것인 화합물.
- 제55항에 있어서, 제2 환은 트리페닐렌 기에 의해 치환되는 것인 화합물.
- 제55항에 있어서, 제2 환은 카바졸을 포함하는 기에 의해 치환되는 것인 화합물.
- 제55항에 있어서, H 또는 할라이드 이외의 기가 알킬 기인 화합물.
- 제64항에 있어서, H 또는 할라이드 이외의 기가 2 이상의 탄소를 포함하는 알킬 기인 화합물.
- 제55항에 있어서, H 또는 할라이드 이외의 기가 아릴 기인 화합물.
- 제55항에 있어서, H 또는 할라이드 이외의 기가 헤테로아릴 기인 화합물.
- 제55항에 있어서, H 또는 할라이드 이외의 기가 디아릴아미노아릴 기인 화합물.
- 제55항에 있어서, 480 nm 미만의 파장에서 인광 방출 스펙트럼에서의 최고 에너지 피크를 갖는 화합물.
- 제55항에 있어서, 동종리간드성 화합물인 화합물.
- 제55항에 있어서, 이종리간드성 화합물인 화합물.
- 제55항에 있어서, 승화성 화합물인 화합물.
- 제55항에 있어서, 제1 환은 금속에 또한 직접 결합된 제3 아릴 또는 헤테로아릴 환에 의해 치환되는 것인 화합물.
- 제73항에 있어서, 제1 및 제3 환은 공동으로 단일음이온성 두 자리 리간드를 포함하는 것인 화합물.
- 제74항에 있어서, 제3 환이 벤젠, 나프탈렌, 퀴놀린, 이소퀴놀린, 피리딘, 피리미딘, 피리다진, 피롤, 옥사졸, 티아졸, 옥사디아졸, 티아디아졸, 푸란 또는 티오펜 환인 화합물.
- 제73항에 있어서, 제1 및 제3 환은 공동으로 단일음이온성 세 자리 리간드를 포함하는 것인 화합물.
- 제74항에 있어서, 제1 및 제3 환은 공동으로 중성 두 자리 리간드를 포함하는 것인 화합물.
- 제55항에 있어서, 제2 환은 2,6-디메틸페닐; 2,4,6-트리메틸페닐; 2,3,4,5,6-펜타메틸페닐; 2,6-디메틸-4-페닐페닐; 2,6-디메틸-4-(3,5-디메틸페닐)페닐; 2,6-디메틸-4-(2,6-디메틸페닐)페닐; 2,6-디메틸-4-(4-피리딜)페닐; 2,6-디메틸-4-(2,6-디메틸-4-피리딜)페닐; 2,4-디메틸-3-나프틸; 2,6-디메틸-4-시아노페닐; 2,6-디메틸-4-(9-카바졸릴)페닐; 2,6-디메틸-4-(9-페닐-3-카바졸릴)페닐; 2,6-디메틸-4-(2,6-디메틸-4-시아노페닐)페닐; 1,8-디메틸-9-카바졸릴; 2,6-디-이소프로필페닐; 2,4,6-트리-이소프로필페닐; 2,6-디-이소프로필-4-페닐페닐; 2,6-디-이소프로필-4-(3,5-디메틸페닐)페닐; 2,6-디-이소프로필-4-(2,6-디메틸페닐)페닐; 2,6-디-이소프로필-4-(4-피리딜)페닐; 2,6-디-이소프로필-4-(2,6-디메틸-4-피리딜)페닐; 2,4-디-이소프로필-3-나프틸; 2,6-디-이소프로필-4-시아노페닐; 2,6-디-이소프로필-4-(9-카바졸릴)페닐; 2,6-디-이소프로필-4-(9-페닐-3-카바졸릴)페닐; 2,6-디-이소프로필-4-(2,6-디메틸-4-시아노페닐)페닐; 2,6-디-t-부틸페닐; 2,6-디-t-부틸-4-(3,5-디메틸페닐)페닐; 2,6-비스(트리메틸실릴)페닐; 2,6-비스(디메틸페닐실릴)페닐; 2,6-비스(트리메틸실릴)-4-(3,5-디메틸페닐)페닐; 2,6-디-페닐페닐; 2,6-디(4-이소프로필페닐)-4-이소프로필페닐; 2,6-디(4-이소프로필페닐)-4-메틸페닐; 2,6-디(4-이소프로필페닐)-4-t-부틸페닐; 2,4,6-트리페닐페닐; 2,6-디-(4-이소프로필페닐)페닐; 2,6-디-(3,5-디메틸페닐)페닐; 2,4,6-트리(4-이소프로필페닐)페닐; 2,6-디-(4-t-부틸페닐)페닐; 2,6-디-(4-플루오로페닐)페닐; 2,6-디-(9-카바졸릴)-4-이소프로필페닐; 2,6-디-(9-페닐-3-카바졸릴)-4-이소프로필페닐; 2,6-디-(4-메톡시페닐)페닐; 2,6-디페닐-4-플루오로페닐; 2,6-디-(2-트리페닐레닐)페닐; 2,6-디-(2-트리페닐레닐)-4-이소프로필페닐; 2,6-디-(2,6-디메틸-4-피리딜)페닐; 2,6-디-(4-시아노페닐)-4-이소프로필페닐; 2,6-디-2-나프틸페닐; 2,6-디-(4-페닐페닐)-4-이소프로필페닐; 2,6-디-(3-페닐페닐)-4-이소프로필페닐; 2,6-디-(4-디페닐아미노페닐)페닐; 2,6-디-(4-디메틸아미노페닐)페닐; 2,6-디-(4-트리메틸실릴페닐)페닐; 2,6-디-(4-트리페닐실릴페닐)페닐; 2,6-디-(4-디페닐메틸실릴페닐)페닐; 및 하기 c1 내지 c7 및 c9 중에서 선택되는 것인 화합물:상기 식 중에서,R1a,c는 각각 2개 이상의 탄소를 포함하는 히드로카빌, 이종원자 치환된 히드로카빌, 아릴 및 헤테로아릴로 구성되는 군 중에서 독립적으로 선택되고;R1b-d는 각각 H, F, 시아노, 알콕시, 아릴옥시, 히드로카빌, 이종원자 치환된 히드로카빌, 아릴 및 헤테로아릴로 구성되는 군 중에서 독립적으로 선택되고, 또한 R1b-d 중 임의의 두 개는 연결되어 환을 형성할 수 있으며;Ar1,2,3은 각각 독립적으로 아릴 또는 헤테로아릴이다.
- 제55항에 있어서, 제1 환은 하기 f1 내지 f4 중에서 선택되는 것인 화합물:상기 식 중에서,Arsr은 제2 환이고,R1a,b는 각각 수소, 히드로카빌, 이종원자 치환된 히드로카빌, 시아노 및 F로 구성되는 군 중에서 독립적으로 선택되고, 또한, R1a,b는 연결되어 환을 형성할 수 있으며;f2, f3 및 f4의 경우, R2a는 제1 환 상의 치환체로서 제3 환이고, 상기 제3 환은 금속에 직접 결합된 아릴 또는 헤테로아릴 환이며;f1의 경우, R2b는 제1 환 상의 치환체로서 제3 환이고, 상기 제3 환은 금속에 직접 결합된 아릴 또는 헤테로아릴 환이며, R2a는 수소, 히드로카빌, 이종원자 치환된 히드로카빌, 시아노 및 F로 구성되는 군 중에서 독립적으로 선택된다.
- 제55항에 있어서, 리간드는 하기 I1 내지 I7, I20 내지 I22 및 I41 내지 I46 중에서 선택되는 것인 화합물:[상기 식 중에서, Ar1은 아릴 또는 헤테로아릴이다][상기 식 중에서,R1a-i는 각각 수소, 히드로카빌, 이종원자 치환된 히드로카빌, 시아노 및 F로 구성되는 군 중에서 독립적으로 선택되고,R2a,b는 각각 2 이상의 탄소를 포함하는 히드로카빌, 이종원자 치환된 히드로카빌, 아릴 및 헤테로아릴로 구성되는 군 중에서 독립적으로 선택된다][상기 식 중에서,R1a-i는 각각 수소, 히드로카빌, 이종원자 치환 히드로카빌, 시아노 및 F로 구성되는 군 중에서 독립적으로 선택되고,Ar1은 아릴 또는 헤테로아릴이고,Ar3a는 4-이소프로필페닐이고;Ar3b는 3,5-디메틸페닐이다]
- 제55항에 있어서, 금속 착물은 하기 중에서 선택되는 것인 화합물:[상기 식 중에서,Ar3은 아릴 또는 헤테로아릴이고,m은 1, 2 또는 3이고,n은 상기 금속의 원자가를 만족시키기 위해 선택된 정수이다][상기 식 중에서,Ar3a는 4-이소프로필페닐이고,Ar3b는 3,5-디메틸페닐이다][상기 식 중에서,R2a-c, R1a-d, R1f-h 및 R1j-q는 각각 수소, 히드로카빌, 이종원자 치환된 히드로카빌, 시아노 및 F로 구성되는 군 중에서 선택되고, R1e 및 R1i는 각각 독립적으로 아릴, 헤테로아릴 또는 알킬이고,Ar1-3은 아릴 또는 헤테로아릴이고,Arsr은 제2 환이고,Arc는 9-카바졸릴 또는 치환된 9-카바졸릴이고,Ln은 동일하거나 상이할 수 있는 보조 리간드이고,m은 1, 2 또는 3이고,n은 M의 원자가를 만족시키기 위해 선택된 정수이고,M은 Re, Ru, Os, Rh, Ir, Pd, Pt, Au 및 하기 화합물 m1 내지 m72로 구성되는 군 중에서 선택되는 금속이다.(상기 표에서, gs1, gs2 및 gs3은 다음과 같다
- 제55항에 있어서, 제1 환이 벤젠 환인 화합물.
- 제55항에 있어서, 제1 환이 나프탈렌 환인 화합물.
- 제55항에 있어서, 제1 환이 퀴놀린 환인 화합물.
- 제55항에 있어서, 제1 환이 이소퀴놀린 환인 화합물.
- 제55항에 있어서, 제1 환이 피리딘 환인 화합물.
- 제55항에 있어서, 제1 환이 피리미딘 환인 화합물.
- 제55항에 있어서, 제1 환이 피리다진 환인 화합물.
- 제55항에 있어서, 제1 환이 피롤 환인 화합물.
- 제55항에 있어서, 제1 환이 옥사졸 환인 화합물.
- 제55항에 있어서, 제1 환이 티아졸 환인 화합물.
- 제55항에 있어서, 제1 환이 옥사디아졸 환인 화합물.
- 제55항에 있어서, 제1 환이 티아디아졸 환인 화합물.
- 제55항에 있어서, 제1 환이 푸란 환인 화합물.
- 제55항에 있어서, 제1 환이 티오펜 환인 화합물.
- 제55항에 있어서, 금속 착물은 두 자리 단일음이온성 N,N-도너 리간드를 포함하는 것인 화합물.
- 제55항에 있어서, 금속 착물은 카벤 도너를 포함하는 것인 화합물.
- 제99항에 있어서, 카벤 도너가 두 자리 단일음이온성 리간드의 일부인 화합물.
- 제55항에 있어서, 제2 환은 플루오라이드 이외의 기에 의해 치환되는 것인 화합물.
- 제55항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 삼중항 에너지가 2.5 eV 초과인 화합물.
- 제55항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 230 g/mol 초과인 화합물.
- 청구항 104은(는) 설정등록료 납부시 포기되었습니다.제55항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 430 g/mol 초과인 화합물.
- 청구항 105은(는) 설정등록료 납부시 포기되었습니다.제55항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 530 g/mol 초과인 화합물.
- 제55항에 있어서,제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 750 g/mol 초과인 화합물.
- 제55항에 있어서, 산정된 단일항-삼중항 갭이 0.4 eV 미만인 화합물.
- 청구항 108은(는) 설정등록료 납부시 포기되었습니다.제55항에 있어서, 산정된 단일항-삼중항 갭이 0.3 eV 미만인 화합물.
- 제55항에 있어서, 산정된 단일항-삼중항 갭이 0.2 eV 미만인 화합물.
- 청구항 110은(는) 설정등록료 납부시 포기되었습니다.제55항에 있어서, 산정된 단일항-삼중항 갭이 0.1 eV 미만인 화합물.
- 제55항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.1 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 112은(는) 설정등록료 납부시 포기되었습니다.제55항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.2 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 제55항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.3 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 114은(는) 설정등록료 납부시 포기되었습니다.제55항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.4 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 제55항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.5 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 제55항에 있어서, 하기 수학식에 의해 산정되는 경우, 델타 E가 0.6 eV 미만인 화합물:델타 E = (삼중항 에너지) - (변형 전기화학적 갭);상기 식에서,삼중항 에너지는 상기 금속 착물의 인광 방출 스펙트럼에서 최고 에너지 피크의 에너지(eV)이며;변형 전기화학적 갭은 금속 착물의 산화 전위와 리간드에 상응하는 중성 화합물의 환원 전위 간의 차이를 나타낸다.
- 청구항 117은(는) 설정등록료 납부시 포기되었습니다.제116항에 있어서, 델타 E가 0.5 eV 미만인 화합물.
- 제116항에 있어서, 델타 E가 0.4 eV 미만인 화합물.
- 청구항 119은(는) 설정등록료 납부시 포기되었습니다.제116항에 있어서, 델타 E가 0.3 eV 미만인 화합물.
- 제116항에 있어서, 델타 E가 0.2 eV 미만인 화합물.
- 애노드; 캐소드; 및 방출층을 포함하는 유기 발광 장치로서,방출층은 애노드와 캐소드 사이에 위치하고, 방출층은 제55항에 따른 인광성 화합물을 포함하는 것인 유기 발광 장치.
- 청구항 122은(는) 설정등록료 납부시 포기되었습니다.인광성 화합물로서,인광성 화합물은 한 자리, 두 자리, 세 자리, 네 자리, 다섯 자리 또는 여섯 자리 리간드의 중성 금속 착물이고;리간드는 금속에 직접 결합된 적어도 하나의 제1 아릴 또는 헤테로아릴 환을 포함하며;제1 환은 금속에 직접 결합되지 않고 두 오르토 위치에서 H 또는 할라이드 이외의 기에 의해 치환된 제2 아릴 또는 헤테로아릴 환에 의해 치환되며;제1 환은 제1 질소 원자를 통해 금속에 배위된 이미다졸이고;금속 착물은 유기 금속 착물이며;
- 청구항 123은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환은 제1 환의 제2 질소 원자에 부착되는 것인 화합물.
- 청구항 124은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 금속은 Re, Ru, Os, Rh, Ir, Pd, Pt 및 Au로 구성된 군 중에서 선택되는 것인 화합물.
- 청구항 125은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 금속은 Os, Ir 및 Pt로 구성된 군 중에서 선택되는 것인 화합물.
- 청구항 126은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 금속이 Ir인 화합물.
- 청구항 127은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환은 아릴, 헤테로아릴 또는 전자 끄는 기에 의해 치환되는 것인 화합물.
- 청구항 128은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, H 또는 할라이드 이외의 기가 알킬 기인 화합물.
- 청구항 129은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, H 또는 할라이드 이외의 기가 2 이상의 탄소를 포함하는 알킬 기인 화합물.
- 청구항 130은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, H 또는 할라이드 이외의 기가 아릴 기인 화합물.
- 청구항 131은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, H 또는 할라이드 이외의 기가 헤테로아릴 기인 화합물.
- 청구항 132은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 480 nm 미만의 파장에서 인광 방출 스펙트럼에서의 최고 에너지 피크를 갖는 화합물.
- 청구항 133은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 동종리간드성 화합물인 화합물.
- 청구항 134은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 이종리간드성 화합물인 화합물.
- 청구항 135은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 승화성 화합물인 화합물.
- 청구항 136은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제1 환은 금속에 또한 직접 결합된 제3 아릴 또는 헤테로아릴 환에 의해 치환되는 것인 화합물.
- 청구항 137은(는) 설정등록료 납부시 포기되었습니다.제136항에 있어서, 제1 및 제3 환은 공동으로 단일음이온성 두 자리 리간드를 포함하는 것인 화합물.
- 청구항 138은(는) 설정등록료 납부시 포기되었습니다.
- 청구항 139은(는) 설정등록료 납부시 포기되었습니다.제136항에 있어서, 제1 및 제3 환은 공동으로 단일음이온성 세 자리 리간드를 포함하는 것인 화합물.
- 청구항 140은(는) 설정등록료 납부시 포기되었습니다.제136항에 있어서, 제1 및 제3 환은 공동으로 중성 두 자리 리간드를 포함하는 것인 화합물.
- 청구항 141은(는) 설정등록료 납부시 포기되었습니다.삭제
- 청구항 142은(는) 설정등록료 납부시 포기되었습니다.삭제
- 청구항 143은(는) 설정등록료 납부시 포기되었습니다.삭제
- 청구항 144은(는) 설정등록료 납부시 포기되었습니다.삭제
- 청구항 145은(는) 설정등록료 납부시 포기되었습니다.삭제
- 청구항 146은(는) 설정등록료 납부시 포기되었습니다.삭제
- 청구항 147은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 금속 착물은 두 자리 단일음이온성 N,N-도너 리간드를 포함하는 것인 화합물.
- 청구항 148은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 금속 착물은 카벤 도너를 포함하는 것인 화합물.
- 청구항 149은(는) 설정등록료 납부시 포기되었습니다.제148항에 있어서, 카벤 도너가 두 자리 단일음이온성 리간드의 일부인 화합물.
- 청구항 150은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환은 플루오라이드 이외의 기에 의해 치환되는 것인 화합물.
- 청구항 151은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 삼중항 에너지가 2.5 eV 초과인 화합물.
- 청구항 152은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 230 g/mol 초과인 화합물.
- 청구항 153은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 430 g/mol 초과인 화합물.
- 청구항 154은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 530 g/mol 초과인 화합물.
- 청구항 155은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 제2 환에 상응하는 아렌 또는 헤테로아렌의 분자량이 750 g/mol 초과인 화합물.
- 청구항 156은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 산정된 단일항-삼중항 갭이 0.4 eV 미만인 화합물.
- 청구항 157은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 산정된 단일항-삼중항 갭이 0.3 eV 미만인 화합물.
- 청구항 158은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 산정된 단일항-삼중항 갭이 0.2 eV 미만인 화합물.
- 청구항 159은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 산정된 단일항-삼중항 갭이 0.1 eV 미만인 화합물.
- 청구항 160은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.1 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 161은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.2 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 162은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.3 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 163은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.4 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 164은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 리간드의 환원 전위는 제2 환 대신 메틸 기를 갖는 상응하는 리간드의 것보다 적어도 0.5 V만큼 덜한 음의 값을 갖는 것인 화합물.
- 청구항 165은(는) 설정등록료 납부시 포기되었습니다.제122항에 있어서, 하기 수학식에 의해 산정되는 경우, 델타 E가 0.6 eV 미만인 화합물:델타 E = (삼중항 에너지) - (변형 전기화학적 갭);상기 식에서,삼중항 에너지는 상기 금속 착물의 인광 방출 스펙트럼에서 최고 에너지 피크의 에너지(eV)이며;변형 전기화학적 갭은 금속 착물의 산화 전위와 리간드에 상응하는 중성 화합물의 환원 전위 간의 차이를 나타낸다.
- 청구항 166은(는) 설정등록료 납부시 포기되었습니다.제165항에 있어서, 델타 E가 0.5 eV 미만인 화합물.
- 청구항 167은(는) 설정등록료 납부시 포기되었습니다.제165항에 있어서, 델타 E가 0.4 eV 미만인 화합물.
- 청구항 168은(는) 설정등록료 납부시 포기되었습니다.제165항에 있어서, 델타 E가 0.3 eV 미만인 화합물.
- 청구항 169은(는) 설정등록료 납부시 포기되었습니다.제165항에 있어서, 델타 E가 0.2 eV 미만인 화합물.
- 청구항 170은(는) 설정등록료 납부시 포기되었습니다.애노드; 캐소드; 및 방출층을 포함하는 유기 발광 장치로서,방출층은 애노드와 캐소드 사이에 위치하고, 방출층은 제122항에 따른 인광성 화합물을 포함하는 것인 유기 발광 장치.
- 제19항에 있어서, 상기 오르토 위치 치환체는 제2 환에 융합되지 않는 것인 화합물.
- 제175항에 있어서, 상기 제1 환은 이미다졸, 퀴놀린, 이소퀴놀린, 피리딘, 피리미딘, 피리다진, 피롤, 옥사졸, 티아졸, 옥사디아졸 및 티아디아졸로 구성되는 군 중에서 선택되는 것인 화합물.
- 제73항에 있어서, 상기 오르토 위치 치환체는 제2 환에 융합되지 않는 것인 화합물.
- 제177항에 있어서, 상기 제1 환은 이미다졸, 퀴놀린, 이소퀴놀린, 피리딘, 피리미딘, 피리다진, 피롤, 옥사졸, 티아졸, 옥사디아졸 및 티아디아졸로 구성되는 군 중에서 선택되는 것인 화합물.
- 제178항에 있어서, 상기 오르토 위치 치환체 둘 다는 C1-20 알킬인 화합물.
- 제122항에 있어서, 상기 오르토 위치 치환체는 제2 환에 융합되지 않는 것인 화합물.
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US11/241,981 US9051344B2 (en) | 2005-05-06 | 2005-10-04 | Stability OLED materials and devices |
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US20200006674A1 (en) | 2020-01-02 |
KR20080007570A (ko) | 2008-01-22 |
TW201420722A (zh) | 2014-06-01 |
TW200706635A (en) | 2007-02-16 |
JP5473326B2 (ja) | 2014-04-16 |
TWI432552B (zh) | 2014-04-01 |
CN101180304A (zh) | 2008-05-14 |
US20220328774A1 (en) | 2022-10-13 |
CN101180304B (zh) | 2015-08-19 |
TW201738359A (zh) | 2017-11-01 |
EP1878053B1 (en) | 2009-08-26 |
US20060251923A1 (en) | 2006-11-09 |
TWI595075B (zh) | 2017-08-11 |
US9051344B2 (en) | 2015-06-09 |
US10381579B2 (en) | 2019-08-13 |
WO2006121811A1 (en) | 2006-11-16 |
CN107011388A (zh) | 2017-08-04 |
US20150249225A1 (en) | 2015-09-03 |
JP5730957B2 (ja) | 2015-06-10 |
EP1878053A1 (en) | 2008-01-16 |
JP2013221157A (ja) | 2013-10-28 |
US11404650B2 (en) | 2022-08-02 |
CN102775447A (zh) | 2012-11-14 |
ATE441208T1 (de) | 2009-09-15 |
JP2008542203A (ja) | 2008-11-27 |
DE602006008771D1 (de) | 2009-10-08 |
CN115160374A (zh) | 2022-10-11 |
TWI618777B (zh) | 2018-03-21 |
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