CN111278838A - 含硼杂环化合物、高聚物、混合物、组合物及其用途 - Google Patents
含硼杂环化合物、高聚物、混合物、组合物及其用途 Download PDFInfo
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- CN111278838A CN111278838A CN201880068814.5A CN201880068814A CN111278838A CN 111278838 A CN111278838 A CN 111278838A CN 201880068814 A CN201880068814 A CN 201880068814A CN 111278838 A CN111278838 A CN 111278838A
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- Prior art keywords
- boron
- group
- containing heterocyclic
- atoms
- heterocyclic compound
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 127
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 127
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 82
- 229920000642 polymer Polymers 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 title claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 128
- 125000003118 aryl group Chemical group 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 47
- -1 cyclane Chemical class 0.000 claims description 44
- 125000006413 ring segment Chemical group 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 230000000903 blocking effect Effects 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000006467 substitution reaction Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 229910052805 deuterium Inorganic materials 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
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- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
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- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000005067 haloformyl group Chemical group 0.000 claims description 2
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 11
- 150000002894 organic compounds Chemical class 0.000 description 11
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 10
- XSAOVBUSKVZIBE-UHFFFAOYSA-N (9-phenylcarbazol-2-yl)boronic acid Chemical compound C=1C(B(O)O)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 XSAOVBUSKVZIBE-UHFFFAOYSA-N 0.000 description 9
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- 150000004982 aromatic amines Chemical class 0.000 description 8
- 238000003775 Density Functional Theory Methods 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 230000005669 field effect Effects 0.000 description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical group 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
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- 229910052698 phosphorus Inorganic materials 0.000 description 5
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- 125000005259 triarylamine group Chemical group 0.000 description 5
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
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- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005136 tetraphenes Chemical class 0.000 description 1
- ONCNIMLKGZSAJT-UHFFFAOYSA-N thieno[3,2-b]furan Chemical compound S1C=CC2=C1C=CO2 ONCNIMLKGZSAJT-UHFFFAOYSA-N 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明涉及一种含硼杂环化合物、高聚物、混合物、组合物及其用途，所述含硼杂环化合物具有如通式(1)或通式(2)所示的结构：
Description
PCT国内申请，说明书已公开。
Claims (15)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201711449989 | 2017-12-27 | ||
| CN2017114499894 | 2017-12-27 | ||
| PCT/CN2018/118989 WO2019128633A1 (zh) | 2017-12-27 | 2018-12-03 | 含硼杂环化合物、高聚物、混合物、组合物及其用途 |
Publications (2)
| Publication Number | Publication Date |
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| CN111278838A true CN111278838A (zh) | 2020-06-12 |
| CN111278838B CN111278838B (zh) | 2023-01-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201880068814.5A Active CN111278838B (zh) | 2017-12-27 | 2018-12-03 | 含硼杂环化合物、高聚物、混合物、组合物及其用途 |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN111278838B (zh) |
| WO (1) | WO2019128633A1 (zh) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114075396A (zh) * | 2020-11-02 | 2022-02-22 | 广东聚华印刷显示技术有限公司 | 组合物、印刷墨水及发光器件 |
| WO2022063107A1 (zh) * | 2020-09-28 | 2022-03-31 | 江苏三月科技股份有限公司 | 一种作为oled掺杂材料的含硼有机化合物及其应用 |
| CN114262339A (zh) * | 2020-09-16 | 2022-04-01 | 广州华睿光电材料有限公司 | 含硼杂环的有机化合物、混合物、组合物及有机电子器件 |
| CN114315876A (zh) * | 2020-09-28 | 2022-04-12 | 江苏三月科技股份有限公司 | 一种作为oled掺杂材料的含硼有机化合物及有机发光器件 |
| WO2022121920A1 (zh) * | 2020-12-10 | 2022-06-16 | 季华实验室 | 一种硼氮化合物、有机电致发光组合物及包含其的有机电致发光器件 |
| WO2022121951A1 (zh) * | 2020-12-10 | 2022-06-16 | 季华实验室 | 一种硼氮化合物、有机电致发光组合物及包含其的有机电致发光器件 |
| WO2023142486A1 (zh) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | 一种硼氮化合物及其制备方法和应用 |
| WO2023142485A1 (zh) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | 一种硼氮化合物及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3763719A1 (en) * | 2019-07-11 | 2021-01-13 | Cynora Gmbh | Organic molecules for optoelectronic devices |
| CN110627822A (zh) * | 2019-10-08 | 2019-12-31 | 吉林大学 | 一种绿光窄光谱三配位硼发光化合物、发光组合物及其应用 |
| CN110759918B (zh) * | 2019-10-31 | 2021-07-06 | 上海天马有机发光显示技术有限公司 | 一种化合物、显示面板及电子设备 |
| CN112778309B (zh) * | 2019-11-06 | 2022-08-12 | 广州华睿光电材料有限公司 | 一种含n稠环化合物及其在有机电子器件中应用 |
| CN112898325A (zh) * | 2019-12-03 | 2021-06-04 | 北京鼎材科技有限公司 | 一种化合物及其应用、包含其的有机电致发光器件 |
| KR20220154774A (ko) * | 2020-03-17 | 2022-11-22 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 헤테로방향족 화합물 |
| KR20220154751A (ko) * | 2020-03-17 | 2022-11-22 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 복소환 화합물 |
| US11296292B2 (en) | 2020-04-15 | 2022-04-05 | Cynora Gmbh | Organic electroluminescent device emitting green light |
| CN114075230A (zh) * | 2020-12-28 | 2022-02-22 | 广东聚华印刷显示技术有限公司 | 含氧硼烷类有机化合物、混合物、组合物及有机电子器件 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501311A (zh) * | 2017-07-14 | 2017-12-22 | 瑞声科技（南京）有限公司 | 有机电致发光材料及其发光器件 |
-
2018
- 2018-12-03 WO PCT/CN2018/118989 patent/WO2019128633A1/zh active Application Filing
- 2018-12-03 CN CN201880068814.5A patent/CN111278838B/zh active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107501311A (zh) * | 2017-07-14 | 2017-12-22 | 瑞声科技（南京）有限公司 | 有机电致发光材料及其发光器件 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114262339A (zh) * | 2020-09-16 | 2022-04-01 | 广州华睿光电材料有限公司 | 含硼杂环的有机化合物、混合物、组合物及有机电子器件 |
| WO2022063107A1 (zh) * | 2020-09-28 | 2022-03-31 | 江苏三月科技股份有限公司 | 一种作为oled掺杂材料的含硼有机化合物及其应用 |
| CN114315876A (zh) * | 2020-09-28 | 2022-04-12 | 江苏三月科技股份有限公司 | 一种作为oled掺杂材料的含硼有机化合物及有机发光器件 |
| CN114075396A (zh) * | 2020-11-02 | 2022-02-22 | 广东聚华印刷显示技术有限公司 | 组合物、印刷墨水及发光器件 |
| WO2022121920A1 (zh) * | 2020-12-10 | 2022-06-16 | 季华实验室 | 一种硼氮化合物、有机电致发光组合物及包含其的有机电致发光器件 |
| WO2022121951A1 (zh) * | 2020-12-10 | 2022-06-16 | 季华实验室 | 一种硼氮化合物、有机电致发光组合物及包含其的有机电致发光器件 |
| WO2023142486A1 (zh) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | 一种硼氮化合物及其制备方法和应用 |
| WO2023142485A1 (zh) * | 2022-01-28 | 2023-08-03 | 季华恒烨(佛山)电子材料有限公司 | 一种硼氮化合物及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2019128633A1 (zh) | 2019-07-04 |
| CN111278838B (zh) | 2023-01-10 |
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