CN105837630A - 一种癸基咪唑类蓝光发射有机发光材料及其制备方法 - Google Patents
一种癸基咪唑类蓝光发射有机发光材料及其制备方法 Download PDFInfo
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- CN105837630A CN105837630A CN201610269874.6A CN201610269874A CN105837630A CN 105837630 A CN105837630 A CN 105837630A CN 201610269874 A CN201610269874 A CN 201610269874A CN 105837630 A CN105837630 A CN 105837630A
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- Prior art keywords
- decyl
- blue
- organic material
- imidazoles
- luminous organic
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- 239000000463 material Substances 0.000 title claims abstract description 31
- LYNVLWLRSACENL-UHFFFAOYSA-N 2-decyl-1h-imidazole Chemical compound CCCCCCCCCCC1=NC=CN1 LYNVLWLRSACENL-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000011368 organic material Substances 0.000 claims description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 16
- 238000003786 synthesis reaction Methods 0.000 abstract description 16
- 239000007787 solid Substances 0.000 abstract description 10
- -1 phenanthroimidazole compound Chemical class 0.000 abstract description 8
- 238000007306 functionalization reaction Methods 0.000 abstract description 5
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 abstract description 5
- 125000002883 imidazolyl group Chemical group 0.000 abstract description 4
- 238000012545 processing Methods 0.000 abstract description 3
- 239000011343 solid material Substances 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000004090 dissolution Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000002189 fluorescence spectrum Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 150000005072 1,3,4-oxadiazoles Chemical class 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000000695 excitation spectrum Methods 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 2
- 230000029553 photosynthesis Effects 0.000 description 2
- 238000010672 photosynthesis Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical group C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- YIEXWEQZQHCRJF-UHFFFAOYSA-N FC(C1=CC=CC=C1N=C1C2=CC=CC=C2)=C1F.C1=CN=CN1 Chemical class FC(C1=CC=CC=C1N=C1C2=CC=CC=C2)=C1F.C1=CN=CN1 YIEXWEQZQHCRJF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000002587 enol group Chemical class 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000006081 fluorescent whitening agent Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
- C07F9/65068—Five-membered rings having the nitrogen atoms in positions 1 and 3 condensed with carbocyclic rings or carbocyclic ring 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
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
Claims (5)
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CN201610269874.6A CN105837630B (zh) | 2016-04-27 | 2016-04-27 | 一种癸基咪唑类蓝光发射有机发光材料及其制备方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105837568A (zh) * | 2016-03-23 | 2016-08-10 | 中国广州分析测试中心 | 一种芴基β-咔啉类化合物,其作为有机发光材料和聚集诱导荧光增强材料的应用及制备方法 |
CN106831864A (zh) * | 2017-01-23 | 2017-06-13 | 黑龙江大学 | 基于苯基苯并咪唑单极热激发延迟荧光主体、电子传输材料的制备方法及应用 |
CN111220580A (zh) * | 2018-11-27 | 2020-06-02 | 恩德莱斯和豪瑟尔分析仪表两合公司 | 传感器膜、膜盖和光化学传感器 |
Citations (6)
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EP0239867A1 (de) * | 1986-03-20 | 1987-10-07 | BASF Aktiengesellschaft | Phenanthroimidazol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
CN101490125A (zh) * | 2006-07-14 | 2009-07-22 | 西巴控股有限公司 | 用于电子应用的新型电致发光聚合物 |
CN103509054A (zh) * | 2012-09-21 | 2014-01-15 | Tcl集团股份有限公司 | 磷光主体材料、其制备方法和应用及电致磷光发光器件 |
CN103865526A (zh) * | 2014-04-03 | 2014-06-18 | 吉林大学 | 基于菲并咪唑衍生物的主体材料及电致发光器件 |
CN104370964A (zh) * | 2014-09-23 | 2015-02-25 | 武汉光电工业技术研究院有限公司 | 电子型磷氧衍生物及电致磷光发光器件 |
CN105061320A (zh) * | 2015-08-12 | 2015-11-18 | 中国广州分析测试中心 | 一种咪唑三酰腙类化合物,其作为有机发光材料的应用及其制备方法 |
-
2016
- 2016-04-27 CN CN201610269874.6A patent/CN105837630B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0239867A1 (de) * | 1986-03-20 | 1987-10-07 | BASF Aktiengesellschaft | Phenanthroimidazol-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
CN101490125A (zh) * | 2006-07-14 | 2009-07-22 | 西巴控股有限公司 | 用于电子应用的新型电致发光聚合物 |
CN103509054A (zh) * | 2012-09-21 | 2014-01-15 | Tcl集团股份有限公司 | 磷光主体材料、其制备方法和应用及电致磷光发光器件 |
CN103865526A (zh) * | 2014-04-03 | 2014-06-18 | 吉林大学 | 基于菲并咪唑衍生物的主体材料及电致发光器件 |
CN104370964A (zh) * | 2014-09-23 | 2015-02-25 | 武汉光电工业技术研究院有限公司 | 电子型磷氧衍生物及电致磷光发光器件 |
CN105061320A (zh) * | 2015-08-12 | 2015-11-18 | 中国广州分析测试中心 | 一种咪唑三酰腙类化合物,其作为有机发光材料的应用及其制备方法 |
Non-Patent Citations (1)
Title |
---|
李维军 等: "含菲并咪唑基团的蓝色电致发光材料", 《高等学校化学学报》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105837568A (zh) * | 2016-03-23 | 2016-08-10 | 中国广州分析测试中心 | 一种芴基β-咔啉类化合物,其作为有机发光材料和聚集诱导荧光增强材料的应用及制备方法 |
CN105837568B (zh) * | 2016-03-23 | 2018-02-23 | 中国广州分析测试中心 | 一种芴基β‑咔啉类化合物,其作为有机发光材料和聚集诱导荧光增强材料的应用及制备方法 |
CN106831864A (zh) * | 2017-01-23 | 2017-06-13 | 黑龙江大学 | 基于苯基苯并咪唑单极热激发延迟荧光主体、电子传输材料的制备方法及应用 |
CN106831864B (zh) * | 2017-01-23 | 2019-04-19 | 黑龙江大学 | 基于苯基苯并咪唑单极热激发延迟荧光主体、电子传输材料的制备方法及应用 |
CN111220580A (zh) * | 2018-11-27 | 2020-06-02 | 恩德莱斯和豪瑟尔分析仪表两合公司 | 传感器膜、膜盖和光化学传感器 |
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Address after: Guangzhou City, Guangdong province 510070 martyrs Road No. 100 building 34 Patentee after: GUANGDONG INSTITUTE OF ANALYSIS (CHINA NATIONAL ANALYTICAL CENTER, GUANGZHOU) Address before: Guangzhou City, Guangdong province 510070 martyrs Road No. 100 building 34 Patentee before: CHINA NATIONAL ANALYTICAL CENTER, GUANGZHOU |
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Address after: 510070 Guangzhou City, Guangzhou, Guangdong, No. 34 Patentee after: Institute of testing and analysis, Guangdong Academy of Sciences (Guangzhou analysis and testing center, China) Address before: 510070 Guangzhou City, Guangzhou, Guangdong, No. 34 Patentee before: GUANGDONG INSTITUTE OF ANALYSIS (CHINA NATIONAL ANALYTICAL CENTER, GUANGZHOU) |
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