JP2010520241A5 - - Google Patents
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- Publication number
- JP2010520241A5 JP2010520241A5 JP2009552094A JP2009552094A JP2010520241A5 JP 2010520241 A5 JP2010520241 A5 JP 2010520241A5 JP 2009552094 A JP2009552094 A JP 2009552094A JP 2009552094 A JP2009552094 A JP 2009552094A JP 2010520241 A5 JP2010520241 A5 JP 2010520241A5
- Authority
- JP
- Japan
- Prior art keywords
- hexane
- mmol
- added
- dcm
- solution
- 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.)
- Granted
Links
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- -1 triethylsilylethynyl Chemical group 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DAMUWSYTQPWFIY-UHFFFAOYSA-N anthra[2,3-b:6,7-b inverted exclamation marka]dithiophene Chemical compound C1=C2C=C(C=C3C(C=CS3)=C3)C3=CC2=CC2=C1C=CS2 DAMUWSYTQPWFIY-UHFFFAOYSA-N 0.000 description 1
- KUFWTXSQQKDMAI-UHFFFAOYSA-N ethynylsilicon Chemical group [Si]C#C KUFWTXSQQKDMAI-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- FWSPXZXVNVQHIF-UHFFFAOYSA-N triethyl(ethynyl)silane Chemical group CC[Si](CC)(CC)C#C FWSPXZXVNVQHIF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07004633 | 2007-03-07 | ||
| EP07004633.9 | 2007-03-07 | ||
| EP07005029 | 2007-03-12 | ||
| EP07005029.9 | 2007-03-12 | ||
| EP07006166 | 2007-03-26 | ||
| EP07006166.8 | 2007-03-26 | ||
| PCT/EP2008/001482 WO2008107089A1 (en) | 2007-03-07 | 2008-02-25 | Silylethynylated heteroacenes and electronic devices made therewith |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014051016A Division JP2014193861A (ja) | 2007-03-07 | 2014-03-14 | シリルエチニル化されたヘテロアセン類およびそれで作製された電子装置 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010520241A JP2010520241A (ja) | 2010-06-10 |
| JP2010520241A5 true JP2010520241A5 (enExample) | 2011-04-14 |
| JP5562652B2 JP5562652B2 (ja) | 2014-07-30 |
Family
ID=39314905
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009552094A Expired - Fee Related JP5562652B2 (ja) | 2007-03-07 | 2008-02-25 | シリルエチニル化されたヘテロアセン類およびそれで作製された電子装置 |
| JP2014051016A Pending JP2014193861A (ja) | 2007-03-07 | 2014-03-14 | シリルエチニル化されたヘテロアセン類およびそれで作製された電子装置 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014051016A Pending JP2014193861A (ja) | 2007-03-07 | 2014-03-14 | シリルエチニル化されたヘテロアセン類およびそれで作製された電子装置 |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2132213B1 (enExample) |
| JP (2) | JP5562652B2 (enExample) |
| KR (1) | KR101591101B1 (enExample) |
| CN (1) | CN101657458B (enExample) |
| GB (1) | GB2460579B (enExample) |
| TW (1) | TWI410427B (enExample) |
| WO (1) | WO2008107089A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2132213B1 (en) * | 2007-03-07 | 2013-05-15 | University of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
| CN101926017B (zh) | 2007-12-17 | 2013-09-25 | 3M创新有限公司 | 基于蒽的可溶液加工的有机半导体 |
| CN102124015B (zh) * | 2008-05-30 | 2015-03-11 | 3M创新有限公司 | 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 |
| CN102119164A (zh) * | 2008-06-19 | 2011-07-06 | 3M创新有限公司 | 可溶液处理的有机半导体 |
| KR101935644B1 (ko) | 2008-10-31 | 2019-01-04 | 바스프 에스이 | 유기 전계 효과 트랜지스터에 사용하기 위한 디케토피롤로피롤 중합체 |
| BRPI1011853A2 (pt) | 2009-05-27 | 2019-09-24 | Basf Se | polímero, material, camada ou componente semicondutores orgânicos, dispositivo semicondutor, processos para a preparação de um dispositivo semicondutor orgânico, e de um polímero, e, uso do polímero e/ou do material, camada ou componente semicondutores orgãnicos. |
| EP2435446B8 (en) | 2009-05-29 | 2017-02-22 | 3M Innovative Properties Company | Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same |
| KR101097313B1 (ko) * | 2009-08-10 | 2011-12-23 | 삼성모바일디스플레이주식회사 | 유기 발광 소자 |
| KR101626363B1 (ko) * | 2009-12-16 | 2016-06-02 | 엘지디스플레이 주식회사 | 안트라세닐계 교호 공중합체, 그 제조 방법 및 이를 이용한 유기 박막 트랜지스터 |
| WO2011076325A1 (en) | 2009-12-23 | 2011-06-30 | Merck Patent Gmbh | Compositions comprising polymeric binders |
| WO2011076324A1 (en) | 2009-12-23 | 2011-06-30 | Merck Patent Gmbh | Compositions comprising organic semiconducting compounds |
| KR102045196B1 (ko) | 2010-04-12 | 2019-11-15 | 메르크 파텐트 게엠베하 | 개선된 성능을 갖는 조성물 |
| US20130026421A1 (en) | 2010-04-12 | 2013-01-31 | Merck Patent Gmbh | Composition and method for preparation of organic electronic devices |
| KR101839636B1 (ko) | 2010-05-19 | 2018-03-16 | 바스프 에스이 | 유기 반도체 소자에 사용하기 위한 디케토피롤로피롤 중합체 |
| WO2011147523A1 (en) | 2010-05-27 | 2011-12-01 | Merck Patent Gmbh | Formulation and method for preparation of organic electronic devices |
| WO2012017005A2 (en) | 2010-08-05 | 2012-02-09 | Basf Se | Polymers based on benzodiones |
| US9306172B2 (en) | 2010-08-13 | 2016-04-05 | Merck Patent Gmbh | Anthra[2,3-b:7,6-b']dithiophene derivatives and their use as organic semiconductors |
| WO2012028244A1 (en) | 2010-09-02 | 2012-03-08 | Merck Patent Gmbh | Process for preparing an organic electronic device |
| US20130161568A1 (en) * | 2010-09-10 | 2013-06-27 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anthra[2,3-b:7,6-b']dithiophene Derivatives and their Use as Organic Semiconductors |
| CN103249739B (zh) * | 2010-12-06 | 2016-02-17 | 默克专利有限公司 | 非线性并苯衍生物及其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 |
| ITMI20111447A1 (it) * | 2011-07-29 | 2013-01-30 | E T C Srl | Transistor organico elettroluminescente |
| WO2013050401A2 (en) | 2011-10-04 | 2013-04-11 | Basf Se | Polymers based on benzodiones |
| WO2013083506A1 (en) | 2011-12-07 | 2013-06-13 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| GB201203159D0 (en) | 2012-02-23 | 2012-04-11 | Smartkem Ltd | Organic semiconductor compositions |
| US9505877B2 (en) | 2012-04-02 | 2016-11-29 | Basf Se | Phenanthro[9,10-B]furan polymers and small molecules for electronic applications |
| KR102079604B1 (ko) | 2012-04-04 | 2020-04-08 | 바스프 에스이 | 디케토피롤로피롤 중합체 및 소분자 |
| JP6207606B2 (ja) | 2012-07-23 | 2017-10-04 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ジチエノベンゾフランポリマーおよび電子的な応用のための小分子 |
| EP2917304B1 (en) | 2012-11-07 | 2016-10-26 | Basf Se | Polymers based on naphthodiones |
| WO2014086722A1 (en) | 2012-12-04 | 2014-06-12 | Basf Se | Functionnalized benzodithiophene polymers for electronic application |
| CN105324441B (zh) | 2013-06-24 | 2018-01-02 | 巴斯夫欧洲公司 | 基于稠合二酮基吡咯并吡咯的聚合物 |
| EP2818493A1 (en) | 2013-06-25 | 2014-12-31 | Basf Se | Near infrared absorbing polymers for electronic applications |
| KR102091906B1 (ko) | 2013-08-28 | 2020-03-20 | 스마트켐 리미티드 | 고분자 유기 반도체 조성물 |
| CN103554138B (zh) * | 2013-10-31 | 2016-02-17 | 兰州大学 | 一种具有有机场效应晶体管性质的材料及其制备方法 |
| JP6181318B2 (ja) | 2014-04-29 | 2017-08-16 | サビック グローバル テクノロジーズ ビー．ブイ． | 光電子工学用途のための高い導電性および吸収を有する小分子／オリゴマーの合成 |
| JP2017017216A (ja) * | 2015-07-02 | 2017-01-19 | Dic株式会社 | 半導体組成物、半導体インク |
| WO2017008883A1 (en) | 2015-07-15 | 2017-01-19 | Merck Patent Gmbh | Composition comprising organic semiconducting compounds |
| WO2017068009A1 (en) | 2015-10-21 | 2017-04-27 | Basf Se | Polymers and compounds based on dipyrrolo[1,2-b:1',2'-g][2,6]naphthyridine-5,11-dione |
| WO2017202635A1 (en) | 2016-05-25 | 2017-11-30 | Basf Se | Semiconductors |
| WO2018114883A1 (de) * | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100303934B1 (ko) * | 1997-03-25 | 2001-09-29 | 포만 제프리 엘 | 낮은작동전압을필요로하는유기반도체를갖는박막전장효과트랜지스터 |
| US5936259A (en) * | 1997-10-16 | 1999-08-10 | Lucent Technologies Inc. | Thin film transistor and organic semiconductor material thereof |
| CN1237626C (zh) * | 1998-08-19 | 2006-01-18 | 普林斯顿大学理事会 | 有机光敏光电器件 |
| JP5089986B2 (ja) * | 2003-11-28 | 2012-12-05 | 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 ハフツング | 有機半導体層およびその改善 |
| US7382040B2 (en) * | 2004-01-15 | 2008-06-03 | Matsushita Electric Industrial Co., Ltd. | Organic field effect transistor and display using same |
| JP2005253231A (ja) * | 2004-03-05 | 2005-09-15 | Fuji Electric Fa Components & Systems Co Ltd | 無停電電源装置、無停電電源管理システム及び無停電電源管理方法 |
| JP2006125270A (ja) * | 2004-10-28 | 2006-05-18 | Takeshi Uchida | 回転駆動装置 |
| WO2006054686A1 (ja) * | 2004-11-18 | 2006-05-26 | Konica Minolta Holdings, Inc. | 有機薄膜トランジスタの製造方法及び有機薄膜トランジスタ |
| JP2006168085A (ja) * | 2004-12-15 | 2006-06-29 | Nissan Motor Co Ltd | 情報化核酸含有木質材料及びその製造方法 |
| JP2006283536A (ja) * | 2005-03-31 | 2006-10-19 | Kagawa Setsubi Kogyosho:Kk | 配管用貫通穴埋め治具 |
| 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 |
| JP2007067262A (ja) * | 2005-09-01 | 2007-03-15 | 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 |
| JP2006151379A (ja) * | 2005-11-21 | 2006-06-15 | Yuji Nishimura | 盗難防止兼用サドルカバー |
| JP5228907B2 (ja) * | 2006-03-10 | 2013-07-03 | コニカミノルタ株式会社 | 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 |
| US7372071B2 (en) * | 2006-04-06 | 2008-05-13 | Xerox Corporation | Functionalized heteroacenes and electronic devices generated therefrom |
| 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 |
| JP2007324288A (ja) * | 2006-05-31 | 2007-12-13 | Konica Minolta Holdings Inc | 有機半導体膜及びその製造方法、有機薄膜トランジスタ及びその製造方法 |
| JP2007335760A (ja) * | 2006-06-16 | 2007-12-27 | Fujifilm Corp | 光電変換膜、並びに、該光電変換膜を含む太陽電池、光電変換素子、又は撮像素子 |
| US20080042127A1 (en) * | 2006-08-17 | 2008-02-21 | Watson Mark D | Transition metal free coupling of highly fluorinated and non-fluorinated pi-electron systems |
| JP2008103464A (ja) * | 2006-10-18 | 2008-05-01 | 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 |
| EP2132213B1 (en) * | 2007-03-07 | 2013-05-15 | University of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
-
2008
- 2008-02-25 EP EP08716025.5A patent/EP2132213B1/en not_active Not-in-force
- 2008-02-25 KR KR1020097020741A patent/KR101591101B1/ko not_active Expired - Fee Related
- 2008-02-25 WO PCT/EP2008/001482 patent/WO2008107089A1/en not_active Ceased
- 2008-02-25 JP JP2009552094A patent/JP5562652B2/ja not_active Expired - Fee Related
- 2008-02-25 CN CN200880007457.8A patent/CN101657458B/zh not_active Expired - Fee Related
- 2008-02-25 GB GB0917170A patent/GB2460579B/en not_active Expired - Fee Related
- 2008-03-04 TW TW097107508A patent/TWI410427B/zh not_active IP Right Cessation
-
2014
- 2014-03-14 JP JP2014051016A patent/JP2014193861A/ja active Pending
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