JP2011525044A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011525044A5 JP2011525044A5 JP2011513554A JP2011513554A JP2011525044A5 JP 2011525044 A5 JP2011525044 A5 JP 2011525044A5 JP 2011513554 A JP2011513554 A JP 2011513554A JP 2011513554 A JP2011513554 A JP 2011513554A JP 2011525044 A5 JP2011525044 A5 JP 2011525044A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- group
- unsubstituted
- alkyl
- heteroaryl
- 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
- 239000000203 mixture Substances 0.000 claims description 33
- 239000011877 solvent mixture Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000001491 aromatic compounds Chemical class 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 11
- 239000004065 semiconductor Substances 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 5
- 125000004405 heteroalkoxy group Chemical group 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 10
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 8
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 8
- JCHJBEZBHANKGA-UHFFFAOYSA-N 1-methoxy-3,5-dimethylbenzene Chemical compound COC1=CC(C)=CC(C)=C1 JCHJBEZBHANKGA-UHFFFAOYSA-N 0.000 description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- 0 CC(CC1)N1C1(C)C=CC(*C(C)=CC)=CC=C1 Chemical compound CC(CC1)N1C1(C)C=CC(*C(C)=CC)=CC=C1 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 2
- OSIGJGFTADMDOB-UHFFFAOYSA-N 1-Methoxy-3-methylbenzene Chemical compound COC1=CC=CC(C)=C1 OSIGJGFTADMDOB-UHFFFAOYSA-N 0.000 description 1
- QGRPVMLBTFGQDQ-UHFFFAOYSA-N 1-chloro-2-methoxybenzene Chemical compound COC1=CC=CC=C1Cl QGRPVMLBTFGQDQ-UHFFFAOYSA-N 0.000 description 1
- YUKILTJWFRTXGB-UHFFFAOYSA-N 1-chloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1 YUKILTJWFRTXGB-UHFFFAOYSA-N 0.000 description 1
- YRGAYAGBVIXNAQ-UHFFFAOYSA-N 1-chloro-4-methoxybenzene Chemical compound COC1=CC=C(Cl)C=C1 YRGAYAGBVIXNAQ-UHFFFAOYSA-N 0.000 description 1
- BLMBNEVGYRXFNA-UHFFFAOYSA-N 1-methoxy-2,3-dimethylbenzene Chemical compound COC1=CC=CC(C)=C1C BLMBNEVGYRXFNA-UHFFFAOYSA-N 0.000 description 1
- UJCFZCTTZWHRNL-UHFFFAOYSA-N 2,4-Dimethylanisole Chemical compound COC1=CC=C(C)C=C1C UJCFZCTTZWHRNL-UHFFFAOYSA-N 0.000 description 1
- GFNZJAUVJCGWLW-UHFFFAOYSA-N 2-methoxy-1,3-dimethylbenzene Chemical compound COC1=C(C)C=CC=C1C GFNZJAUVJCGWLW-UHFFFAOYSA-N 0.000 description 1
- SJZAUIVYZWPNAS-UHFFFAOYSA-N 2-methoxy-1,4-dimethylbenzene Chemical compound COC1=CC(C)=CC=C1C SJZAUIVYZWPNAS-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- LVUBSVWMOWKPDJ-UHFFFAOYSA-N 4-methoxy-1,2-dimethylbenzene Chemical compound COC1=CC=C(C)C(C)=C1 LVUBSVWMOWKPDJ-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6059508P | 2008-06-11 | 2008-06-11 | |
| US61/060,595 | 2008-06-11 | ||
| PCT/US2009/045571 WO2009151978A1 (en) | 2008-06-11 | 2009-05-29 | Mixed solvent systems for deposition of organic semiconductors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011525044A JP2011525044A (ja) | 2011-09-08 |
| JP2011525044A5 true JP2011525044A5 (cg-RX-API-DMAC7.html) | 2012-07-19 |
| JP5406284B2 JP5406284B2 (ja) | 2014-02-05 |
Family
ID=40910017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011513554A Expired - Fee Related JP5406284B2 (ja) | 2008-06-11 | 2009-05-29 | 有機半導体の堆積のための混合溶媒系 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8232550B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2304821B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5406284B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102106012B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009151978A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0612929D0 (en) | 2006-06-29 | 2006-08-09 | Univ Cambridge Tech | High-performance organic field-effect transistors based on dilute, crystalline-crystalline polymer blends and block copolymers |
| PL3981502T3 (pl) | 2007-04-26 | 2025-06-16 | Johnson Matthey Public Limited Company | Katalizatory scr z metalami przejściowymi/zeolitem |
| JP5658145B2 (ja) * | 2008-05-30 | 2015-01-21 | スリーエム イノベイティブ プロパティズ カンパニー | シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法 |
| KR20170091788A (ko) * | 2009-12-23 | 2017-08-09 | 메르크 파텐트 게엠베하 | 중합체성 결합제를 포함하는 조성물 |
| JP5840621B2 (ja) | 2009-12-23 | 2016-01-06 | メルク パテント ゲーエムベーハー | 有機半導体化合物を含む組成物 |
| WO2011147523A1 (en) * | 2010-05-27 | 2011-12-01 | Merck Patent Gmbh | Formulation and method for preparation of organic electronic devices |
| GB201013820D0 (en) * | 2010-08-18 | 2010-09-29 | Cambridge Display Tech Ltd | Low contact resistance organic thin film transistors |
| US8389744B1 (en) * | 2011-10-11 | 2013-03-05 | University Of New Hampshire | TTPO (5 6,7-trithiapentacene-13-one) and its derivatives: a new class of thermally stable, photooxidatively resistant organic semiconductors |
| US9293711B2 (en) | 2012-08-09 | 2016-03-22 | Polyera Corporation | Organic semiconductor formulations |
| KR102145424B1 (ko) * | 2013-11-11 | 2020-08-18 | 엘지디스플레이 주식회사 | 표시장치 제조용 잉크 및 이를 이용한 표시장치의 제조방법 |
| JP6578645B2 (ja) * | 2014-10-21 | 2019-09-25 | 東ソー株式会社 | 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ |
| JP7019559B2 (ja) * | 2015-07-15 | 2022-02-15 | メルク パテント ゲーエムベーハー | 有機半導体化合物を含む組成物 |
| US11495744B2 (en) * | 2017-03-21 | 2022-11-08 | Nippon Kayaku Kabushiki Kaisha | Organic semiconductor composition, organic thin film, and organic thin film transistor |
| GB2560934A (en) | 2017-03-28 | 2018-10-03 | Sumitomo Chemical Co | Solvent systems for the preparation of photosensitive organic electronic devices |
| US11283023B2 (en) | 2017-06-08 | 2022-03-22 | Corning Incorporated | Doping of other polymers into organic semi-conducting polymers |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6265243B1 (en) * | 1999-03-29 | 2001-07-24 | Lucent Technologies Inc. | Process for fabricating organic circuits |
| EP1364420B1 (en) * | 2001-02-27 | 2012-10-10 | Cambridge Display Technology Limited | Formulation for depositing a material on a substrate using ink jet printing |
| KR100552866B1 (ko) * | 2001-08-09 | 2006-02-20 | 아사히 가세이 가부시키가이샤 | 유기 반도체 소자 |
| US6690029B1 (en) * | 2001-08-24 | 2004-02-10 | University Of Kentucky Research Foundation | Substituted pentacenes and electronic devices made with substituted pentacenes |
| CN1582506A (zh) * | 2001-09-27 | 2005-02-16 | 3M创新有限公司 | 取代并五苯半导体 |
| US7098525B2 (en) * | 2003-05-08 | 2006-08-29 | 3M Innovative Properties Company | Organic polymers, electronic devices, and methods |
| ATE475971T1 (de) * | 2003-11-28 | 2010-08-15 | Merck Patent Gmbh | Organische halbleiterschicht-formulierungen mit polyacenen und organischen binderpolymeren |
| DE102004007777A1 (de) * | 2004-02-18 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Lösungen organischer Halbleiter |
| DE102004023276A1 (de) * | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Lösungen organischer Halbleiter |
| KR20070093075A (ko) | 2004-12-28 | 2007-09-17 | 이데미쓰 고산 가부시키가이샤 | 유기 ｅｌ 도포막 형성용 잉크 및 그의 제조 방법 |
| US7264872B2 (en) * | 2004-12-30 | 2007-09-04 | 3M Innovative Properties Company | Durable high index nanocomposites for AR coatings |
| US7241437B2 (en) | 2004-12-30 | 2007-07-10 | 3M Innovative Properties Company | Zirconia particles |
| US7211679B2 (en) * | 2005-03-09 | 2007-05-01 | 3M Innovative Properties Company | Perfluoroether acyl oligothiophene compounds |
| 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 |
| US7319153B2 (en) * | 2005-07-29 | 2008-01-15 | 3M Innovative Properties Company | 6,13-Bis(thienyl)pentacene compounds |
| US7514710B2 (en) | 2005-12-28 | 2009-04-07 | 3M Innovative Properties Company | Bottom gate thin film transistors |
| US20070146426A1 (en) * | 2005-12-28 | 2007-06-28 | Nelson Brian K | All-inkjet printed thin film transistor |
| US7608679B2 (en) * | 2006-03-31 | 2009-10-27 | 3M Innovative Properties Company | Acene-thiophene copolymers |
| US7495251B2 (en) * | 2006-04-21 | 2009-02-24 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers with silylethynyl groups |
| US7666968B2 (en) * | 2006-04-21 | 2010-02-23 | 3M Innovative Properties Company | Acene-thiophene copolymers with silethynly groups |
| JP2007311677A (ja) * | 2006-05-22 | 2007-11-29 | Konica Minolta Holdings Inc | 有機薄膜トランジスタの製造方法、有機薄膜トランジスタ |
| JP5055849B2 (ja) * | 2006-06-14 | 2012-10-24 | コニカミノルタホールディングス株式会社 | 表示装置、有機薄膜トランジスタの製造方法 |
| JP2010512005A (ja) | 2006-12-01 | 2010-04-15 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 改善された溶液処理方法による有機半導体膜の性能特性の向上 |
| 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 |
| JP5658145B2 (ja) * | 2008-05-30 | 2015-01-21 | スリーエム イノベイティブ プロパティズ カンパニー | シリルメチルペンタセン化合物及び組成物、並びにそれらの製造及び使用方法 |
| 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 |
| WO2009158201A1 (en) | 2008-06-27 | 2009-12-30 | 3M Innovative Properties Company | Methods op fabricating crystalline organic semiconductive layers |
| 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 |
| US7948016B1 (en) * | 2009-11-03 | 2011-05-24 | 3M Innovative Properties Company | Off-center deposition of organic semiconductor in an organic semiconductor device |
-
2009
- 2009-05-29 EP EP09763269A patent/EP2304821B1/en not_active Not-in-force
- 2009-05-29 WO PCT/US2009/045571 patent/WO2009151978A1/en not_active Ceased
- 2009-05-29 CN CN2009801295021A patent/CN102106012B/zh not_active Expired - Fee Related
- 2009-05-29 US US12/996,473 patent/US8232550B2/en not_active Expired - Fee Related
- 2009-05-29 JP JP2011513554A patent/JP5406284B2/ja not_active Expired - Fee Related