CN110857267B - 芳香酮化合物及其有机发光器件 - Google Patents
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- CN110857267B CN110857267B CN201810960049.XA CN201810960049A CN110857267B CN 110857267 B CN110857267 B CN 110857267B CN 201810960049 A CN201810960049 A CN 201810960049A CN 110857267 B CN110857267 B CN 110857267B
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- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
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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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
Abstract
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Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0348202A (ja) * | 1989-03-08 | 1991-03-01 | Kuraray Co Ltd | パターン作製法 |
JPH03251846A (ja) * | 1990-02-28 | 1991-11-11 | Kuraray Co Ltd | 感光性樹脂組成物、それを用いたパターンおよびパターン作製法 |
JPH04309954A (ja) * | 1991-04-08 | 1992-11-02 | Kuraray Co Ltd | パターン作製法 |
CN101460588A (zh) * | 2006-05-31 | 2009-06-17 | 默克专利有限公司 | 用于有机电致发光器件的新材料 |
JP2010202620A (ja) * | 2009-03-06 | 2010-09-16 | Nihon Univ | 1,3,5−トリベンゾイルベンゼンの製造方法 |
CN102076818A (zh) * | 2008-07-18 | 2011-05-25 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
CN102264798A (zh) * | 2008-10-23 | 2011-11-30 | 巴斯夫欧洲公司 | 支化聚芳醚和含所述醚的热塑性模塑材料 |
CN103265421A (zh) * | 2013-03-28 | 2013-08-28 | 大连理工大学 | 由1,3,5-苯三甲酸合成1,3,5-三(4-氟苯酰基)苯的合成方法 |
CN104628544A (zh) * | 2015-01-13 | 2015-05-20 | 黑龙江省科学院石油化学研究院 | 一种三分支芳族结构的丙烯基苯氧基化合物及其制备方法和利用其改性的双马来酰亚胺树脂 |
KR20150110157A (ko) * | 2014-03-24 | 2015-10-02 | 주식회사 엘지화학 | [3,5-비스(4-플루오로벤조일)페닐](4-플루오로페닐)메탄온의 제조 방법 |
CN108137444A (zh) * | 2015-12-04 | 2018-06-08 | 广州华睿光电材料有限公司 | 三联苯并环戊二烯类化合物、高聚物、混合物、组合物以及有机电子器件 |
CN108977197A (zh) * | 2018-08-21 | 2018-12-11 | 电子科技大学 | 有机电致发光材料及制备方法和有机电致发光器件 |
CN109988305A (zh) * | 2017-12-29 | 2019-07-09 | 深圳光启尖端技术有限责任公司 | 改性双马来酰亚胺树脂及其制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013142038A2 (en) * | 2012-03-23 | 2013-09-26 | Oxigene, Inc. | Compositions and methods for inhibition of cathepsins |
-
2018
- 2018-08-22 CN CN201810960049.XA patent/CN110857267B/zh active Active
- 2018-09-06 TW TW107131321A patent/TWI683802B/zh active
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0348202A (ja) * | 1989-03-08 | 1991-03-01 | Kuraray Co Ltd | パターン作製法 |
JPH03251846A (ja) * | 1990-02-28 | 1991-11-11 | Kuraray Co Ltd | 感光性樹脂組成物、それを用いたパターンおよびパターン作製法 |
JPH04309954A (ja) * | 1991-04-08 | 1992-11-02 | Kuraray Co Ltd | パターン作製法 |
CN101460588A (zh) * | 2006-05-31 | 2009-06-17 | 默克专利有限公司 | 用于有机电致发光器件的新材料 |
CN102076818A (zh) * | 2008-07-18 | 2011-05-25 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
CN102264798A (zh) * | 2008-10-23 | 2011-11-30 | 巴斯夫欧洲公司 | 支化聚芳醚和含所述醚的热塑性模塑材料 |
JP2010202620A (ja) * | 2009-03-06 | 2010-09-16 | Nihon Univ | 1,3,5−トリベンゾイルベンゼンの製造方法 |
CN103265421A (zh) * | 2013-03-28 | 2013-08-28 | 大连理工大学 | 由1,3,5-苯三甲酸合成1,3,5-三(4-氟苯酰基)苯的合成方法 |
KR20150110157A (ko) * | 2014-03-24 | 2015-10-02 | 주식회사 엘지화학 | [3,5-비스(4-플루오로벤조일)페닐](4-플루오로페닐)메탄온의 제조 방법 |
CN104628544A (zh) * | 2015-01-13 | 2015-05-20 | 黑龙江省科学院石油化学研究院 | 一种三分支芳族结构的丙烯基苯氧基化合物及其制备方法和利用其改性的双马来酰亚胺树脂 |
CN108137444A (zh) * | 2015-12-04 | 2018-06-08 | 广州华睿光电材料有限公司 | 三联苯并环戊二烯类化合物、高聚物、混合物、组合物以及有机电子器件 |
CN109988305A (zh) * | 2017-12-29 | 2019-07-09 | 深圳光启尖端技术有限责任公司 | 改性双马来酰亚胺树脂及其制备方法 |
CN108977197A (zh) * | 2018-08-21 | 2018-12-11 | 电子科技大学 | 有机电致发光材料及制备方法和有机电致发光器件 |
Non-Patent Citations (3)
Title |
---|
""Trade-Off " Hidden in Condensed State Solvation: Multiradiative Channels Design for Highly Efficient Solution-Processed Purely Organic Electroluminescence at High Brightness";Xinyi Cai等;《Adv. Funct. Mater.》;20180214;第28卷(第7期);第1704927(1-9)页 * |
"Examination of Halogen Bonding Interactions in Electronically Distinct but Structurally Related Tris(haloarenes)";F. Christopher Pigge等;《Crystal Growth & Design》;20101231;第10卷(第1期);第224-231页 * |
"Metal-free synthesis of 1,3,5-trisubstituted benzenes by the cyclotrimerization of enaminones or alkynes in water";Jie-Ping Wan等;《RSC Advances》;20141231;第20499-20505页 * |
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