CN102124015B - 甲硅烷基乙炔基并五苯化合物和组合物及其制备和使用方法 - Google Patents
甲硅烷基乙炔基并五苯化合物和组合物及其制备和使用方法 Download PDFInfo
- Publication number
- CN102124015B CN102124015B CN200980128699.7A CN200980128699A CN102124015B CN 102124015 B CN102124015 B CN 102124015B CN 200980128699 A CN200980128699 A CN 200980128699A CN 102124015 B CN102124015 B CN 102124015B
- Authority
- CN
- China
- Prior art keywords
- unsubstituted
- pentacene
- pentacene compound
- substituted
- replace
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Thin Film Transistor (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5771508P | 2008-05-30 | 2008-05-30 | |
| US61/057,715 | 2008-05-30 | ||
| PCT/US2009/045667 WO2009155106A1 (en) | 2008-05-30 | 2009-05-29 | Silylethynyl pentacene compounds and compositions and methods of making and using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102124015A CN102124015A (zh) | 2011-07-13 |
| CN102124015B true CN102124015B (zh) | 2015-03-11 |
Family
ID=41078164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200980128699.7A Expired - Fee Related CN102124015B (zh) | 2008-05-30 | 2009-05-29 | 甲硅烷基乙炔基并五苯化合物和组合物及其制备和使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8956555B2 (https=) |
| EP (1) | EP2307427B1 (https=) |
| JP (2) | JP5658145B2 (https=) |
| KR (1) | KR101622420B1 (https=) |
| CN (1) | CN102124015B (https=) |
| WO (1) | WO2009155106A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101622420B1 (ko) | 2008-05-30 | 2016-05-18 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 실릴에티닐 펜타센 화합물 및 조성물 및 그의 제조 및 사용 방법 |
| JP5406284B2 (ja) * | 2008-06-11 | 2014-02-05 | スリーエム イノベイティブ プロパティズ カンパニー | 有機半導体の堆積のための混合溶媒系 |
| SG176209A1 (en) * | 2009-05-29 | 2012-01-30 | 3M Innovative Properties Co | Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same |
| US8779179B2 (en) | 2010-05-28 | 2014-07-15 | 3M Innovative Properties Company | Synthesis of silyl acetylenes |
| WO2011150020A1 (en) | 2010-05-28 | 2011-12-01 | 3M Innovative Properties Company | Synthesis of silyl acetylenes |
| EP2614068A1 (en) * | 2010-09-10 | 2013-07-17 | Merck Patent GmbH | Anthra[2,3-b:7,6b']dithiophene derivatives and their use as organic semiconductors |
| WO2012071243A2 (en) | 2010-11-22 | 2012-05-31 | 3M Innovative Properties Company | Assembly and electronic devices including the same |
| US9373801B2 (en) | 2011-01-28 | 2016-06-21 | Merck Patent Gmbh | Flavanthrene derivatives and their use as organic semiconductors |
| CN103415526A (zh) | 2011-03-11 | 2013-11-27 | 默克专利股份有限公司 | 二萘并[2,3-a:2’,3’-h]吩嗪类和它们作为有机半导体的用途 |
| GB201108864D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Transistors and methods of making them |
| GB201108865D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Semiconductor compounds |
| GB2491810B (en) * | 2011-05-31 | 2018-03-21 | Smartkem Ltd | Organic semiconductor compositions |
| GB201203159D0 (en) | 2012-02-23 | 2012-04-11 | Smartkem Ltd | Organic semiconductor compositions |
| US10354049B2 (en) | 2012-08-22 | 2019-07-16 | Koninklijke Philips N.V. | Automatic detection and retrieval of prior annotations relevant for an imaging study for efficient viewing and reporting |
| CN105229814B (zh) * | 2013-05-23 | 2017-11-10 | 富士胶片株式会社 | 有机半导体组合物、有机薄膜晶体管、以及电子纸及显示装置 |
| KR102091906B1 (ko) | 2013-08-28 | 2020-03-20 | 스마트켐 리미티드 | 고분자 유기 반도체 조성물 |
| CN106328812B (zh) * | 2015-07-06 | 2019-10-18 | 元太科技工业股份有限公司 | 有源元件及其制作方法 |
| CN106854218B (zh) * | 2016-12-30 | 2019-03-05 | 上海升翕光电科技有限公司 | 一种硅蒽类衍生物及其制备方法和有机发光器件 |
| CN107464879A (zh) * | 2017-10-17 | 2017-12-12 | 上海幂方电子科技有限公司 | 可喷墨打印的有机半导体材料组合物 |
| CN115785141A (zh) * | 2022-11-30 | 2023-03-14 | 西北师范大学 | 噻二唑喹喔啉衍生物及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008107089A1 (en) * | 2007-03-07 | 2008-09-12 | University Of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
| WO2008128618A1 (en) * | 2007-04-19 | 2008-10-30 | Merck Patent Gmbh | Process for preparing substituted pentacenes |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6026A (en) * | 1849-01-09 | Cast-iron car-wheel | ||
| JP4855616B2 (ja) | 1999-10-27 | 2012-01-18 | スリーエム イノベイティブ プロパティズ カンパニー | フルオロケミカルスルホンアミド界面活性剤 |
| CA2401487C (en) | 2000-02-29 | 2011-06-21 | Japan Science And Technology Agency | Polyacene derivatives and process of producing thereof |
| EP2199437B1 (en) | 2001-08-09 | 2015-07-29 | Asahi Kasei Kabushiki Kaisha | Use of an organic semiconductor solution to form oriented polyacene crystals on a substrate |
| US6690029B1 (en) | 2001-08-24 | 2004-02-10 | University Of Kentucky Research Foundation | Substituted pentacenes and electronic devices made with substituted pentacenes |
| JP2005504811A (ja) | 2001-09-27 | 2005-02-17 | スリーエム イノベイティブ プロパティズ カンパニー | 置換ペンタセン半導体 |
| US7098525B2 (en) | 2003-05-08 | 2006-08-29 | 3M Innovative Properties Company | Organic polymers, electronic devices, and methods |
| EP1783781A3 (en) * | 2003-11-28 | 2007-10-03 | Merck Patent GmbH | Organic semiconducting layer formulations comprising polyacenes and organic binder polymers |
| US7385221B1 (en) | 2005-03-08 | 2008-06-10 | University Of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
| US20060220007A1 (en) | 2005-04-05 | 2006-10-05 | Bailey David B | Acene compounds having a single terminal fused thiophene as semiconductor materials for thin film transistors and methods of making the same |
| EP1986247A1 (en) * | 2005-05-12 | 2008-10-29 | MERCK PATENT GmbH | Polyacene and semiconductor Formulation |
| JP2008545631A (ja) | 2005-05-21 | 2008-12-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | オリゴマーポリアセンおよび半導体調製物 |
| US20060267004A1 (en) * | 2005-05-27 | 2006-11-30 | Fallis Alexander G | Compounds comprising a linear series of five fused carbon rings, and preparation thereof |
| US7498662B2 (en) | 2005-11-18 | 2009-03-03 | 3M Innovative Properties Company | Dielectric media including surface-treated metal oxide particles |
| JP2007158062A (ja) * | 2005-12-06 | 2007-06-21 | Konica Minolta Holdings Inc | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| US20070146426A1 (en) * | 2005-12-28 | 2007-06-28 | Nelson Brian K | All-inkjet printed thin film transistor |
| EP1974401A1 (en) | 2006-01-21 | 2008-10-01 | Merck Patent GmbH | Electronic short channel device comprising an organic semiconductor formulation |
| US7666968B2 (en) | 2006-04-21 | 2010-02-23 | 3M Innovative Properties Company | Acene-thiophene copolymers with silethynly groups |
| US7495251B2 (en) * | 2006-04-21 | 2009-02-24 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers with silylethynyl groups |
| JP2007299852A (ja) | 2006-04-28 | 2007-11-15 | Konica Minolta Holdings Inc | 有機半導体材料、有機半導体膜、有機半導体デバイス及び有機薄膜トランジスタ |
| US7879688B2 (en) | 2007-06-29 | 2011-02-01 | 3M Innovative Properties Company | Methods for making electronic devices with a solution deposited gate dielectric |
| US20090001356A1 (en) | 2007-06-29 | 2009-01-01 | 3M Innovative Properties Company | Electronic devices having a solution deposited gate dielectric |
| EP2232606A1 (en) | 2007-12-17 | 2010-09-29 | 3M Innovative Properties Company | Solution processable organic semiconductors based on anthracene |
| KR101622420B1 (ko) | 2008-05-30 | 2016-05-18 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 실릴에티닐 펜타센 화합물 및 조성물 및 그의 제조 및 사용 방법 |
| JP5406284B2 (ja) * | 2008-06-11 | 2014-02-05 | スリーエム イノベイティブ プロパティズ カンパニー | 有機半導体の堆積のための混合溶媒系 |
| WO2009158201A1 (en) | 2008-06-27 | 2009-12-30 | 3M Innovative Properties Company | Methods op fabricating crystalline organic semiconductive layers |
| SG176209A1 (en) | 2009-05-29 | 2012-01-30 | 3M Innovative Properties Co | Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same |
-
2009
- 2009-05-29 KR KR1020107029524A patent/KR101622420B1/ko not_active Expired - Fee Related
- 2009-05-29 US US12/995,145 patent/US8956555B2/en not_active Expired - Fee Related
- 2009-05-29 CN CN200980128699.7A patent/CN102124015B/zh not_active Expired - Fee Related
- 2009-05-29 EP EP09767417.0A patent/EP2307427B1/en not_active Not-in-force
- 2009-05-29 JP JP2011511852A patent/JP5658145B2/ja not_active Expired - Fee Related
- 2009-05-29 WO PCT/US2009/045667 patent/WO2009155106A1/en not_active Ceased
-
2014
- 2014-07-17 JP JP2014146824A patent/JP2015007049A/ja not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008107089A1 (en) * | 2007-03-07 | 2008-09-12 | University Of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
| WO2008128618A1 (en) * | 2007-04-19 | 2008-10-30 | Merck Patent Gmbh | Process for preparing substituted pentacenes |
Non-Patent Citations (4)
| Title |
|---|
| Design,Synthesis,andPropertiesofNew Derivatives of Pentacene;JinyueJiang 等;《J.Org.Chem.》;20060207;第71卷;2155-2158 * |
| FunctionalizedHigher Acenes:Hexacene and Heptacene;MarciaM.Payne,SeanR.Parkin,and JohnE.Anthony*;《J.AM.CHEM.SOC.》;20051231;第127卷(第22期);8028-8029 * |
| Stable,Crystalline Acenedithiophenes;MarciaM.Payne,SusanA.Odom,SeanR.Parkin,andJohnE.Anthony*;《ORGANIC LETTERS》;20040824;第6卷(第19期);3325-3328 * |
| Synthesis and Characterization of Electron-Deficient Pentacenes;ChristopherR.Swartz 等;《ORGANIC LETTERS》;20050630;第7卷(第15期);3163-3166 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5658145B2 (ja) | 2015-01-21 |
| EP2307427A1 (en) | 2011-04-13 |
| US8956555B2 (en) | 2015-02-17 |
| KR20110026437A (ko) | 2011-03-15 |
| JP2011521972A (ja) | 2011-07-28 |
| US20110073813A1 (en) | 2011-03-31 |
| EP2307427B1 (en) | 2015-02-18 |
| JP2015007049A (ja) | 2015-01-15 |
| CN102124015A (zh) | 2011-07-13 |
| WO2009155106A1 (en) | 2009-12-23 |
| KR101622420B1 (ko) | 2016-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20150311 Termination date: 20190529 |
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| CF01 | Termination of patent right due to non-payment of annual fee |