CN109790163B - 咔唑类化合物及其应用 - Google Patents
咔唑类化合物及其应用 Download PDFInfo
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- CN109790163B CN109790163B CN201780059447.8A CN201780059447A CN109790163B CN 109790163 B CN109790163 B CN 109790163B CN 201780059447 A CN201780059447 A CN 201780059447A CN 109790163 B CN109790163 B CN 109790163B
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- carbazole
- organic
- based compound
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 253
- -1 Carbazole compound Chemical class 0.000 title abstract description 79
- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 239000000463 material Substances 0.000 claims description 121
- 125000003118 aryl group Chemical group 0.000 claims description 85
- 239000010410 layer Substances 0.000 claims description 53
- 229920000642 polymer Polymers 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 19
- 230000000903 blocking effect Effects 0.000 claims description 18
- 238000002347 injection Methods 0.000 claims description 18
- 239000007924 injection Substances 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 230000005669 field effect Effects 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 239000002346 layers by function Substances 0.000 claims description 6
- 238000013086 organic photovoltaic Methods 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 239000003849 aromatic solvent Substances 0.000 claims description 3
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000005453 ketone based solvent Substances 0.000 claims description 3
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- 125000001072 heteroaryl group Chemical group 0.000 description 56
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- 238000000034 method Methods 0.000 description 29
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 16
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 125000006413 ring segment Chemical group 0.000 description 13
- 238000001035 drying Methods 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
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- 125000003368 amide group Chemical group 0.000 description 11
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- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 10
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- 239000000243 solution Substances 0.000 description 10
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
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- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 4
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- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 description 4
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- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
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- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Indole Compounds (AREA)
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CN2016111232849 | 2016-12-08 | ||
CN201611123284 | 2016-12-08 | ||
PCT/CN2017/115309 WO2018103745A1 (fr) | 2016-12-08 | 2017-12-08 | Composé carbazole et son utilisation |
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CN109790163A CN109790163A (zh) | 2019-05-21 |
CN109790163B true CN109790163B (zh) | 2022-04-05 |
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KR102342248B1 (ko) * | 2019-07-15 | 2021-12-22 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
KR102342249B1 (ko) * | 2019-07-15 | 2021-12-23 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
CN113336771B (zh) * | 2021-06-25 | 2024-04-30 | 长春海谱润斯科技股份有限公司 | 一种稠环咔唑衍生物及其有机电致发光器件 |
CN115636813A (zh) * | 2021-07-19 | 2023-01-24 | 上海和辉光电股份有限公司 | 一种电子传输材料及其制备方法和应用 |
CN116445172A (zh) * | 2023-04-04 | 2023-07-18 | 淮阴工学院 | 一种含三氮苯咔唑盘状光固化液晶的4d打印形状记忆树脂材料及其制备方法和应用 |
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CN104350627B (zh) * | 2012-06-12 | 2016-05-18 | 东丽株式会社 | 发光元件材料及发光元件 |
KR101720079B1 (ko) * | 2015-03-31 | 2017-03-28 | (주)위델소재 | 퀴녹살린 유도체 화합물 및 이를 이용한 유기전계 발광소자 |
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