JP2014520186A5 - - Google Patents
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- JP2014520186A5 JP2014520186A5 JP2014516086A JP2014516086A JP2014520186A5 JP 2014520186 A5 JP2014520186 A5 JP 2014520186A5 JP 2014516086 A JP2014516086 A JP 2014516086A JP 2014516086 A JP2014516086 A JP 2014516086A JP 2014520186 A5 JP2014520186 A5 JP 2014520186A5
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- JP
- Japan
- Prior art keywords
- donor
- regioregular
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- acceptor
- independently
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- 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.)
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- 125000003118 aryl group Chemical group 0.000 claims description 38
- 239000000178 monomer Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 15
- -1 alkyl luma Chemical compound 0.000 claims description 12
- 230000005669 field effect Effects 0.000 claims description 11
- 229910052732 germanium Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 claims description 8
- RJVPHPXQVBVPLV-UHFFFAOYSA-N cyclopenta[2,1-b:3,4-b']dithiophene Chemical compound S1C=CC2=CC3=CCSC3=C21 RJVPHPXQVBVPLV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002800 charge carrier Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000004065 semiconductor Substances 0.000 claims description 3
- 238000006254 arylation reaction Methods 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims 30
- 238000006243 chemical reaction Methods 0.000 claims 5
- 238000006880 cross-coupling reaction Methods 0.000 claims 5
- 241000023320 Luma <angiosperm> Species 0.000 claims 1
- 238000005700 Stille cross coupling reaction Methods 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161498390P | 2011-06-17 | 2011-06-17 | |
| US61/498,390 | 2011-06-17 | ||
| US201261645970P | 2012-05-11 | 2012-05-11 | |
| US61/645,970 | 2012-05-11 | ||
| PCT/US2012/043004 WO2012174561A2 (en) | 2011-06-17 | 2012-06-18 | REGIOREGULAR PYRIDAL[2,1,3]THIADIAZOLE π-CONJUGATED COPOLYMERS FOR ORGANIC SEMICONDUCTORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014520186A JP2014520186A (ja) | 2014-08-21 |
| JP2014520186A5 true JP2014520186A5 (https=) | 2015-07-30 |
| JP6141577B2 JP6141577B2 (ja) | 2017-06-07 |
Family
ID=47354196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014516086A Active JP6141577B2 (ja) | 2011-06-17 | 2012-06-18 | 有機半導体のための位置規則性ピリダル［２，１，３］チアジアゾールπ−共役コポリマー |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US9293708B2 (https=) |
| EP (1) | EP2721087B1 (https=) |
| JP (1) | JP6141577B2 (https=) |
| WO (1) | WO2012174561A2 (https=) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9000423B2 (en) * | 2007-10-31 | 2015-04-07 | The Regents Of The University Of California | Processing additive for single-component solution processed organic field-effect transistors |
| WO2012074853A1 (en) | 2010-11-22 | 2012-06-07 | The Regents Of The University Of California | Organic small molecule semiconducting chromophores for use in organic electronic devices |
| US10186661B2 (en) | 2015-03-02 | 2019-01-22 | The Regents Of The University Of California | Blade coating on nanogrooved substrates yielding aligned thin films of high mobility semiconducting polymers |
| US9573158B2 (en) * | 2014-01-03 | 2017-02-21 | The Regents Of The University Of California | High mobility polymer thin-film transistors with capillarity-mediated self-assembly |
| EP2768880B1 (en) | 2011-10-20 | 2025-11-26 | Université Laval | Preparation of high molecular weight polymers by direct arylation and heteroarylation |
| JP2013237813A (ja) * | 2012-05-16 | 2013-11-28 | Kuraray Co Ltd | π電子共役重合体及びそれを用いた有機半導体デバイス |
| US10128441B2 (en) | 2012-09-07 | 2018-11-13 | The Regents Of The University Of California | Field-effect transistors based on macroscopically oriented polymers |
| US9559306B2 (en) | 2012-09-07 | 2017-01-31 | The Regents Of The University Of California | Field-effect transistors based on macroscopically oriented polymers with high saturation mobility |
| CN103848960A (zh) * | 2012-11-28 | 2014-06-11 | 海洋王照明科技股份有限公司 | 含噻吩-苯-噻吩单元的聚合物及其制备方法和太阳能电池器件 |
| US9796811B2 (en) | 2013-08-23 | 2017-10-24 | Sumitomo Chemical Company, Limited | Polymer compound and organic semiconductor device using the same |
| KR102386679B1 (ko) * | 2014-05-26 | 2022-04-13 | 메르크 파텐트 게엠베하 | 테트라-아릴 인다세노디티오펜계 폴리시클릭 중합체 및 이들의 용도 |
| EP3174915A1 (en) | 2014-07-29 | 2017-06-07 | Merck Patent GmbH | Tetra-heteroaryl indacenodithiophene-based polycyclic polymers and their use |
| CN104637823B (zh) * | 2015-02-06 | 2019-07-16 | 京东方科技集团股份有限公司 | 薄膜晶体管的制备方法及薄膜晶体管、阵列基板 |
| JP6104973B2 (ja) | 2015-03-30 | 2017-03-29 | 株式会社東芝 | 光電変換素子およびその製造方法 |
| JP6864635B2 (ja) * | 2015-05-12 | 2021-04-28 | 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Ｍｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | チアジアゾロピリジンポリマー、その合成およびその使用 |
| WO2017006765A1 (ja) | 2015-07-07 | 2017-01-12 | 富士フイルム株式会社 | 有機半導体素子、化合物、有機半導体組成物、および、有機半導体膜の製造方法 |
| JP6484724B2 (ja) | 2015-11-20 | 2019-03-13 | 富士フイルム株式会社 | 有機半導体組成物、有機半導体膜、有機薄膜トランジスタおよび有機薄膜トランジスタの製造方法 |
| US20180371157A1 (en) * | 2015-12-18 | 2018-12-27 | Merck Patent Gmbh | Thiadiazolopyridine polymers, their synthesis and their use |
| EP3432375B1 (en) | 2016-03-16 | 2021-12-29 | FUJIFILM Corporation | Organic semiconductor composition, method for manufacturing organic thin film transistor, and organic thin film transistor |
| JP6706316B2 (ja) | 2016-04-01 | 2020-06-03 | 富士フイルム株式会社 | 有機半導体素子、重合体、有機半導体組成物及び有機半導体膜 |
| JP6574052B2 (ja) | 2016-04-01 | 2019-09-11 | 富士フイルム株式会社 | 有機半導体素子、重合体、有機半導体組成物及び有機半導体膜 |
| WO2018181055A1 (ja) | 2017-03-31 | 2018-10-04 | 富士フイルム株式会社 | 有機半導体素子、有機半導体組成物、有機半導体膜の製造方法、有機半導体膜、並びに、これらに用いる化合物及びポリマー |
| JP6752466B2 (ja) | 2017-03-31 | 2020-09-09 | 富士フイルム株式会社 | 有機半導体素子、有機半導体組成物、有機半導体膜の製造方法、有機半導体膜、並びに、これらに用いる化合物及びポリマー |
| JP6814448B2 (ja) | 2017-03-31 | 2021-01-20 | 富士フイルム株式会社 | 有機半導体素子、有機半導体組成物、有機半導体膜の製造方法、有機半導体膜、並びに、これらに用いる化合物及びポリマー |
| JP7270254B2 (ja) | 2017-06-16 | 2023-05-10 | デューク ユニバーシティ | 改善された標識検出、演算、検体感知、および調整可能な乱数生成のための共鳴体ネットワーク |
| CN107573489B (zh) * | 2017-08-03 | 2019-12-27 | 湘潭大学 | 一种含双吡啶二唑衍生物受体的聚合物半导体及其制备方法与应用 |
| US20190181348A1 (en) * | 2017-09-27 | 2019-06-13 | The Regents Of The University Of California | Branch point effect on structure and electronic properties of conjugated polymers |
| US11233207B2 (en) * | 2017-11-02 | 2022-01-25 | The Regents Of The University Of California | Narrow bandgap non-fullerene acceptors and devices including narrow bandgap non-fullerene acceptors |
| EP3745484B1 (en) | 2018-01-23 | 2023-09-27 | FUJIFILM Corporation | Organic semiconductor element, organic semiconductor composition, organic semiconductor film, method for producing organic semiconductor film, and polymer used therefor |
| KR101947055B1 (ko) * | 2018-02-08 | 2019-05-02 | 울산과학기술원 | Pbdttt 기반 고분자의 제조방법 |
| EP3790918A4 (en) | 2018-05-05 | 2022-03-16 | Jason D. Azoulay | OPEN LAYER CONJUGATED POLYMERIC CONDUCTORS, COMPOSITES, AND COMPOSITIONS |
| KR102441144B1 (ko) * | 2018-05-17 | 2022-09-06 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 전자 소자 |
| CN110655637A (zh) * | 2018-06-29 | 2020-01-07 | 华南理工大学 | 一类含吡啶杂环单元的规整型聚合物其及制备方法与应用 |
| CN110655639B (zh) * | 2018-06-29 | 2022-07-26 | 华南理工大学 | 一类含吡啶杂环单元的嵌段共聚物及其制备方法与应用 |
| CN110655653B (zh) * | 2018-06-29 | 2022-04-22 | 华南理工大学 | 一类主链含金属元素的a-d-a型聚合物及制备方法与其应用 |
| US11649320B2 (en) | 2018-09-21 | 2023-05-16 | University Of Southern Mississippi | Thiol-based post-modification of conjugated polymers |
| US11781986B2 (en) | 2019-12-31 | 2023-10-10 | University Of Southern Mississippi | Methods for detecting analytes using conjugated polymers and the inner filter effect |
| CN111233898B (zh) * | 2020-03-09 | 2021-05-11 | 湘潭大学 | 一种含等规双吡啶噻二唑受体的有机小分子共轭材料及其制备方法与应用 |
| KR102509090B1 (ko) * | 2020-04-10 | 2023-03-10 | 한양대학교 산학협력단 | 탄소나노튜브의 분산 방법, 공액고분자-탄소나노튜브 복합체를 포함하는 전도성 필름 및 이를 포함하는 열전소자 |
| CN113461713B (zh) * | 2021-07-14 | 2022-07-22 | 南京邮电大学 | 一种cpdt基梯形格分子及其制备方法和应用 |
| KR102855934B1 (ko) * | 2021-11-30 | 2025-09-04 | 한국화학연구원 | P형 유기 반도체 화합물, 이의 제조방법 및 이를 함유하는 반투명 유기 태양전지 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7144950B2 (en) * | 2003-09-17 | 2006-12-05 | The Regents Of The University Of California | Conformationally flexible cationic conjugated polymers |
| US7781673B2 (en) | 2005-07-14 | 2010-08-24 | Konarka Technologies, Inc. | Polymers with low band gaps and high charge mobility |
| US7772485B2 (en) * | 2005-07-14 | 2010-08-10 | Konarka Technologies, Inc. | Polymers with low band gaps and high charge mobility |
| US20080275212A1 (en) | 2005-11-24 | 2008-11-06 | Martin Heeney | Process of Preparing Regioregular Polymers |
| EP2144949A2 (en) * | 2007-05-15 | 2010-01-20 | Plextronics, Inc. | Mixed halogen polymerization |
| US20100311879A1 (en) * | 2007-10-31 | 2010-12-09 | Reike Metals Inc. | Reverse addition process for preparation of regioregular conducting polymers |
| WO2009152165A2 (en) * | 2008-06-09 | 2009-12-17 | Plextronics, Inc. | Sulfonated polythiophenes comprising fused ring repeat units |
| US8343382B2 (en) * | 2009-05-22 | 2013-01-01 | The Regents Of The University Of California | Band gap control in conjugated oligomers and polymers via Lewis acids |
| AU2010266105B2 (en) | 2009-07-02 | 2015-12-10 | University Of Florida Research Foundation, Inc. | Soluble alternating donor-acceptor conjugated polymer electrochromes |
| US8729221B2 (en) * | 2012-04-25 | 2014-05-20 | The Regents Of The University Of California | Conjugated copolymers chiral side chain for organic thin film transistors |
| US9559306B2 (en) * | 2012-09-07 | 2017-01-31 | The Regents Of The University Of California | Field-effect transistors based on macroscopically oriented polymers with high saturation mobility |
| WO2014039049A1 (en) * | 2012-09-07 | 2014-03-13 | Empire Technology Development Llc | Regioregular copolymers and methods for making same |
-
2012
- 2012-06-18 WO PCT/US2012/043004 patent/WO2012174561A2/en not_active Ceased
- 2012-06-18 JP JP2014516086A patent/JP6141577B2/ja active Active
- 2012-06-18 US US13/526,371 patent/US9293708B2/en active Active
- 2012-06-18 EP EP12801086.5A patent/EP2721087B1/en active Active
-
2013
- 2013-11-22 US US14/087,702 patent/US10396286B2/en active Active
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