KR102001624B1 - 함질소 방향족 화합물, 유기 반도체 재료 및 유기 전자 디바이스 - Google Patents
함질소 방향족 화합물, 유기 반도체 재료 및 유기 전자 디바이스 Download PDFInfo
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- KR102001624B1 KR102001624B1 KR1020147018764A KR20147018764A KR102001624B1 KR 102001624 B1 KR102001624 B1 KR 102001624B1 KR 1020147018764 A KR1020147018764 A KR 1020147018764A KR 20147018764 A KR20147018764 A KR 20147018764A KR 102001624 B1 KR102001624 B1 KR 102001624B1
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- carbon atoms
- organic
- organic semiconductor
- aromatic heterocyclic
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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|---|---|---|---|
| JP2011268918 | 2011-12-08 | ||
| JPJP-P-2011-268918 | 2011-12-08 | ||
| PCT/JP2012/081045 WO2013084805A1 (ja) | 2011-12-08 | 2012-11-30 | 含窒素芳香族化合物、有機半導体材料及び有機電子デバイス |
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| KR20140101411A KR20140101411A (ko) | 2014-08-19 |
| KR102001624B1 true KR102001624B1 (ko) | 2019-07-18 |
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| JP (1) | JP6073806B2 (zh) |
| KR (1) | KR102001624B1 (zh) |
| CN (1) | CN103987715B (zh) |
| TW (1) | TWI586667B (zh) |
| WO (1) | WO2013084805A1 (zh) |
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|---|---|---|---|---|
| WO2015145315A1 (en) * | 2014-03-25 | 2015-10-01 | Basf Se | Azaazene analogues and their use as semiconductor |
| US9929353B2 (en) | 2014-04-02 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN104251751B (zh) * | 2014-09-26 | 2017-01-25 | 中国科学院半导体研究所 | 一种多感官集成的电子皮肤及其制造方法 |
| EP3305792B1 (en) * | 2015-06-03 | 2024-04-10 | LG Chem, Ltd. | Nitrogen-containing condensed cyclic compound and organic light emitting element using same |
| CN107987086A (zh) * | 2017-12-26 | 2018-05-04 | 长春海谱润斯科技有限公司 | 基于咔唑类结构的稠环化合物及其有机发光器件 |
| EP3865486A1 (en) | 2020-02-13 | 2021-08-18 | Idemitsu Kosan Co., Ltd. | Heterocyclic compound and an organic electroluminescence device comprising the heterocyclic compound |
| KR102319866B1 (ko) * | 2020-02-21 | 2021-10-29 | 성균관대학교산학협력단 | 유기 발광재료 및 이를 포함하는 유기 전계 발광장치 |
| KR102597660B1 (ko) * | 2020-12-10 | 2023-11-03 | 성균관대학교산학협력단 | 보론산계 화합물을 포함하는 나노 박막, 이의 제조 방법, 및 이를 포함하는 복합 나노 박막 |
| KR102588564B1 (ko) * | 2020-12-10 | 2023-10-13 | 성균관대학교산학협력단 | 2개의 벤젠고리 및 아민기를 갖는 화합물을 포함하는 나노 박막, 이의 제조 방법, 및 이를 포함하는 복합 나노 박막 |
| KR102524386B1 (ko) * | 2020-12-10 | 2023-04-21 | 성균관대학교산학협력단 | 2개의 질소-포함 방향족 헤테로 고리를 갖는 화합물을 포함하는 나노 박막, 이의 제조 방법, 및 이를 포함하는 복합 나노 박막 |
| KR102592869B1 (ko) * | 2020-12-10 | 2023-10-24 | 성균관대학교산학협력단 | 질소-포함 방향족 헤테로 고리를 갖는 화합물을 포함하는 나노 박막, 이의 제조 방법, 및 이를 포함하는 복합 나노 박막 |
| KR20220092768A (ko) | 2020-12-25 | 2022-07-04 | 삼성전자주식회사 | 함질소 축합환 화합물, 형광발광제, 유기 전계 발광 소자용 재료 및 유기 전계 발광 소자 |
| KR20220092799A (ko) | 2020-12-25 | 2022-07-04 | 삼성전자주식회사 | 함질소 축합환 화합물, 형광 발광제, 유기 전계발광 소자용 재료 및 유기 전계발광 소자 |
| CN114573597B (zh) * | 2022-03-23 | 2024-01-26 | 浙江虹舞科技有限公司 | 一种具有多个大位阻基团围绕的含氮杂环化合物、发光材料及有机发光元件 |
| EP4450589A1 (en) | 2023-04-18 | 2024-10-23 | Samsung Electronics Co., Ltd. | Blue luminescent compound and organic light-emitting device |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009290091A (ja) | 2008-05-30 | 2009-12-10 | Idemitsu Kosan Co Ltd | 有機薄膜太陽電池用材料及びそれを用いた有機薄膜太陽電池 |
| JP2011222974A (ja) | 2010-03-23 | 2011-11-04 | Nippon Steel Chem Co Ltd | 有機半導体材料及び有機半導体素子 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2199437B1 (en) | 2001-08-09 | 2015-07-29 | Asahi Kasei Kabushiki Kaisha | Use of an organic semiconductor solution to form oriented polyacene crystals on a substrate |
| CN101394365A (zh) * | 2007-09-17 | 2009-03-25 | 上海华为技术有限公司 | 一种消息关联方法及用户终端以及服务器 |
| JP2009090091A (ja) * | 2007-09-18 | 2009-04-30 | Olympus Corp | 歯科用観察装置 |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009290091A (ja) | 2008-05-30 | 2009-12-10 | Idemitsu Kosan Co Ltd | 有機薄膜太陽電池用材料及びそれを用いた有機薄膜太陽電池 |
| JP2011222974A (ja) | 2010-03-23 | 2011-11-04 | Nippon Steel Chem Co Ltd | 有機半導体材料及び有機半導体素子 |
Non-Patent Citations (1)
| Title |
|---|
| New Journal of Chemistry, 2010, Vol.34, No.7, 1243-1246 |
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| WO2013084805A1 (ja) | 2013-06-13 |
| JPWO2013084805A1 (ja) | 2015-04-27 |
| TWI586667B (zh) | 2017-06-11 |
| CN103987715B (zh) | 2017-06-30 |
| TW201335159A (zh) | 2013-09-01 |
| JP6073806B2 (ja) | 2017-02-01 |
| CN103987715A (zh) | 2014-08-13 |
| KR20140101411A (ko) | 2014-08-19 |
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