CN113563205A - 新型化合物以及包含上述新型化合物的有机发光元件 - Google Patents
新型化合物以及包含上述新型化合物的有机发光元件 Download PDFInfo
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- CN113563205A CN113563205A CN202110470494.XA CN202110470494A CN113563205A CN 113563205 A CN113563205 A CN 113563205A CN 202110470494 A CN202110470494 A CN 202110470494A CN 113563205 A CN113563205 A CN 113563205A
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114773210A (zh) * | 2021-12-28 | 2022-07-22 | 北京鼎材科技有限公司 | 一种有机化合物及其应用 |
WO2023210698A1 (ja) * | 2022-04-26 | 2023-11-02 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
CN117088781A (zh) * | 2023-10-20 | 2023-11-21 | 浙江华显光电科技有限公司 | 一种有机化合物、具有该化合物的oled和有机发光装置 |
CN118373748A (zh) * | 2024-06-24 | 2024-07-23 | 浙江华显光电科技有限公司 | 一种有机化合物、具有该化合物的oled及应用 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20180116740A (ko) * | 2017-04-17 | 2018-10-25 | 주식회사 동진쎄미켐 | 신규 화합물 및 이를 포함하는 유기 발광 소자 |
TW201942330A (zh) * | 2018-03-30 | 2019-11-01 | 南韓商東進世美肯股份有限公司 | 新穎化合物及包含其的有機發光裝置 |
CN110642819A (zh) * | 2018-06-27 | 2020-01-03 | 东进世美肯株式会社 | 新颖化合物及包含其的有机发光器件 |
CN110698448A (zh) * | 2018-07-10 | 2020-01-17 | 东进世美肯株式会社 | 新颖化合物及包含其的有机发光器件 |
CN113272287A (zh) * | 2019-02-15 | 2021-08-17 | 株式会社Lg化学 | 新型化合物及利用其的有机发光器件 |
CN114207861A (zh) * | 2019-08-02 | 2022-03-18 | 德山新勒克斯有限公司 | 有机电子器件 |
-
2021
- 2021-04-28 KR KR1020210054862A patent/KR20210133882A/ko active Search and Examination
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20180116740A (ko) * | 2017-04-17 | 2018-10-25 | 주식회사 동진쎄미켐 | 신규 화합물 및 이를 포함하는 유기 발광 소자 |
TW201942330A (zh) * | 2018-03-30 | 2019-11-01 | 南韓商東進世美肯股份有限公司 | 新穎化合物及包含其的有機發光裝置 |
CN110642819A (zh) * | 2018-06-27 | 2020-01-03 | 东进世美肯株式会社 | 新颖化合物及包含其的有机发光器件 |
CN110698448A (zh) * | 2018-07-10 | 2020-01-17 | 东进世美肯株式会社 | 新颖化合物及包含其的有机发光器件 |
CN113272287A (zh) * | 2019-02-15 | 2021-08-17 | 株式会社Lg化学 | 新型化合物及利用其的有机发光器件 |
CN114207861A (zh) * | 2019-08-02 | 2022-03-18 | 德山新勒克斯有限公司 | 有机电子器件 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114773210A (zh) * | 2021-12-28 | 2022-07-22 | 北京鼎材科技有限公司 | 一种有机化合物及其应用 |
CN114773210B (zh) * | 2021-12-28 | 2024-04-23 | 北京鼎材科技有限公司 | 一种有机化合物及其应用 |
WO2023210698A1 (ja) * | 2022-04-26 | 2023-11-02 | 出光興産株式会社 | 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器 |
CN117088781A (zh) * | 2023-10-20 | 2023-11-21 | 浙江华显光电科技有限公司 | 一种有机化合物、具有该化合物的oled和有机发光装置 |
CN118373748A (zh) * | 2024-06-24 | 2024-07-23 | 浙江华显光电科技有限公司 | 一种有机化合物、具有该化合物的oled及应用 |
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