CN110746344A - 一种化合物及其应用 - Google Patents
一种化合物及其应用 Download PDFInfo
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- CN110746344A CN110746344A CN201911136445.1A CN201911136445A CN110746344A CN 110746344 A CN110746344 A CN 110746344A CN 201911136445 A CN201911136445 A CN 201911136445A CN 110746344 A CN110746344 A CN 110746344A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
化合物 | HOMO(eV) | LUMO(eV) | S<sub>1</sub>(eV) | T<sub>1</sub>(eV) | △E<sub>ST</sub>(eV) | E<sub>g</sub>(eV) |
P1 | -5.205 | -1.943 | 3.035 | 2.803 | 0.23 | 3.26 |
P2 | -5.208 | -1.952 | 3.01 | 2.790 | 0.22 | 3.26 |
P3 | -5.206 | -1.961 | 3.0112 | 2.791 | 0.22 | 3.25 |
P4 | -5.231 | -1.951 | 3.027 | 2.792 | 0.23 | 3.28 |
P55 | -5.340 | -1.967 | 3.116 | 2.826 | 0.29 | 3.37 |
P63 | -5.621 | -1.776 | 3.532 | 2.741 | 0.79 | 3.84 |
C1 | -5.000 | -1.963 | 2.875 | 2.431 | 0.44 | 3.04 |
Claims (18)
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Publication number | Priority date | Publication date | Assignee | Title |
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CN110563763A (zh) * | 2019-09-29 | 2019-12-13 | 上海天马有机发光显示技术有限公司 | 一种化合物及其应用 |
US11760764B2 (en) | 2020-05-22 | 2023-09-19 | Aligos Therapeutics, Inc. | Methods and compositions for targeting PD-L1 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2161272A1 (en) * | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
CN102812574A (zh) * | 2010-03-31 | 2012-12-05 | 出光兴产株式会社 | 有机电致发光元件用材料和使用其的有机电致发光元件 |
US20150279909A1 (en) * | 2012-10-31 | 2015-10-01 | Panasonic Intellectual Property Management Co., Ltd. | Organic electroluminescence element and illumination device |
CN108727398A (zh) * | 2018-06-28 | 2018-11-02 | 宁波卢米蓝新材料有限公司 | 一种稠环化合物及其制备方法和用途 |
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Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2161272A1 (en) * | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
CN102812574A (zh) * | 2010-03-31 | 2012-12-05 | 出光兴产株式会社 | 有机电致发光元件用材料和使用其的有机电致发光元件 |
US20150279909A1 (en) * | 2012-10-31 | 2015-10-01 | Panasonic Intellectual Property Management Co., Ltd. | Organic electroluminescence element and illumination device |
CN108727398A (zh) * | 2018-06-28 | 2018-11-02 | 宁波卢米蓝新材料有限公司 | 一种稠环化合物及其制备方法和用途 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110563763A (zh) * | 2019-09-29 | 2019-12-13 | 上海天马有机发光显示技术有限公司 | 一种化合物及其应用 |
US11760764B2 (en) | 2020-05-22 | 2023-09-19 | Aligos Therapeutics, Inc. | Methods and compositions for targeting PD-L1 |
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