KR102270475B1 - 다환 화합물 및 이를 포함하는 유기 발광 소자 - Google Patents
다환 화합물 및 이를 포함하는 유기 발광 소자 Download PDFInfo
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- KR102270475B1 KR102270475B1 KR1020190081379A KR20190081379A KR102270475B1 KR 102270475 B1 KR102270475 B1 KR 102270475B1 KR 1020190081379 A KR1020190081379 A KR 1020190081379A KR 20190081379 A KR20190081379 A KR 20190081379A KR 102270475 B1 KR102270475 B1 KR 102270475B1
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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| US20210078992A1 (en) * | 2018-07-05 | 2021-03-18 | Lg Chem, Ltd. | Polycyclic compound and organic light emitting diode comprising same |
| US20220052273A1 (en) * | 2019-02-13 | 2022-02-17 | Hodogaya Chemical Co., Ltd. | Compound having benzazole ring structure, and organic electroluminescent device |
| CN112300143B (zh) * | 2019-07-30 | 2022-08-16 | 江苏三月科技股份有限公司 | 一种基于咔唑为核心的有机化合物及其应用 |
| CN112851649B (zh) * | 2019-11-28 | 2023-09-29 | 南京高光半导体材料有限公司 | 一种含有多元杂环结构的有机电致发光化合物及有机电致发光器件和应用 |
| KR102170558B1 (ko) * | 2020-03-12 | 2020-10-27 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기발광소자 |
| KR102517278B1 (ko) * | 2020-11-12 | 2023-04-05 | 주식회사 랩토 | 트리아진 또는 피리미딘 유도체, 및 이를 포함한 유기전계발광소자 |
| CN113336744B (zh) * | 2021-06-23 | 2024-04-26 | 长春海谱润斯科技股份有限公司 | 一种杂环衍生物及其有机电致发光器件 |
| CN113527280B (zh) * | 2021-07-09 | 2024-04-16 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
| CN113845512B (zh) * | 2021-09-18 | 2023-05-05 | 长春海谱润斯科技股份有限公司 | 一种包含杂环的化合物及其有机电致发光器件 |
| CN113816921B (zh) * | 2021-09-23 | 2023-12-19 | 长春海谱润斯科技股份有限公司 | 一种杂环类化合物及其有机电致发光器件 |
| CN114149361B (zh) * | 2021-12-17 | 2024-01-26 | 长春海谱润斯科技股份有限公司 | 一种杂环衍生物及其有机电致发光器件 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3533788A1 (en) * | 2018-02-28 | 2019-09-04 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
| WO2019231212A1 (ko) * | 2018-05-29 | 2019-12-05 | 주식회사 엘지화학 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
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