JP2012528100A5 - - Google Patents
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- JP2012528100A5 JP2012528100A5 JP2012512320A JP2012512320A JP2012528100A5 JP 2012528100 A5 JP2012528100 A5 JP 2012528100A5 JP 2012512320 A JP2012512320 A JP 2012512320A JP 2012512320 A JP2012512320 A JP 2012512320A JP 2012528100 A5 JP2012528100 A5 JP 2012528100A5
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- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- independently
- formula
- aryl
- 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
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- 239000004065 semiconductor Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 17
- 230000005669 field effect Effects 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000013086 organic photovoltaic Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 30
- 229910052799 carbon Inorganic materials 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 17
- 229910052717 sulfur Inorganic materials 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 150000001721 carbon Chemical group 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000005647 linker group Chemical group 0.000 claims 8
- 150000002430 hydrocarbons Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 229920001577 copolymer Polymers 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- -1 C 1 -C 4 Alkoxy Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000732 arylene group Chemical group 0.000 claims 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 3
- 125000005336 allyloxy group Chemical group 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000000178 monomer Substances 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 238000007334 copolymerization reaction Methods 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004419 alkynylene group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000005556 thienylene group Chemical group 0.000 claims 1
- 0 Cc1nc2c(*)c(*)c(*)c(*)c2nc1C Chemical compound Cc1nc2c(*)c(*)c(*)c(*)c2nc1C 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09161243 | 2009-05-27 | ||
| EP09161243.2 | 2009-05-27 | ||
| EP09170185 | 2009-09-14 | ||
| EP09170185.4 | 2009-09-14 | ||
| PCT/EP2010/057038 WO2010136401A2 (en) | 2009-05-27 | 2010-05-21 | Polycyclic dithiophenes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012528100A JP2012528100A (ja) | 2012-11-12 |
| JP2012528100A5 true JP2012528100A5 (https=) | 2013-07-04 |
| JP5886190B2 JP5886190B2 (ja) | 2016-03-16 |
Family
ID=42309549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012512320A Expired - Fee Related JP5886190B2 (ja) | 2009-05-27 | 2010-05-21 | 多環式ジチオフェン |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US9233930B2 (https=) |
| EP (1) | EP2435497B1 (https=) |
| JP (1) | JP5886190B2 (https=) |
| KR (1) | KR101805203B1 (https=) |
| CN (1) | CN102449023B (https=) |
| WO (1) | WO2010136401A2 (https=) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8859714B1 (en) | 2009-07-01 | 2014-10-14 | Northwestern University | Polymeric semiconductors and related devices |
| JP5666474B2 (ja) * | 2009-12-14 | 2015-02-12 | 出光興産株式会社 | 多環縮環化合物、及び、それを用いた有機薄膜トランジスタ |
| US8895693B2 (en) | 2010-06-25 | 2014-11-25 | Samsung Electronics Co., Ltd. | Electron-donating polymers and organic solar cells including the same |
| WO2012083510A1 (zh) * | 2010-12-20 | 2012-06-28 | 海洋王照明科技股份有限公司 | 有机半导体材料及其制备方法和应用 |
| JP2012162514A (ja) * | 2011-01-20 | 2012-08-30 | Kuraray Co Ltd | ジチエノゲルモール重合体及びそれを含有した有機半導体デバイス |
| KR20140015319A (ko) * | 2011-02-02 | 2014-02-06 | 이데미쓰 고산 가부시키가이샤 | 함질소 헤테로환 유도체, 유기 전기발광 소자용 전자 수송 재료, 및 그것을 이용하여 이루어지는 유기 전기발광 소자 |
| GB201105482D0 (en) * | 2011-03-31 | 2011-05-18 | Imp Innovations Ltd | Polymers |
| JP2014518904A (ja) * | 2011-04-27 | 2014-08-07 | ビーエーエスエフ ソシエタス・ヨーロピア | ジチエノピリドンコポリマーをベースとする半導体材料 |
| KR101853395B1 (ko) | 2011-05-23 | 2018-04-30 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 태양 전지 |
| US10316135B2 (en) * | 2011-06-17 | 2019-06-11 | The Regents Of The University Of California | Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications |
| KR101777326B1 (ko) | 2011-10-05 | 2017-09-12 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 유기 태양 전지 |
| EP2774940A4 (en) | 2011-11-02 | 2014-11-05 | Mitsubishi Chem Corp | METHOD OF PREPARING CONJUGATED POLYMER, CONJUGATED POLYMER, PHOTOELECTRIC CONVERSION ELEMENT, SOLAR CELL AND SOLAR CELL MODULE |
| JP6040939B2 (ja) | 2011-11-02 | 2016-12-07 | 三菱化学株式会社 | 縮合多環芳香族化合物の製造方法及び共役高分子 |
| US8835598B2 (en) * | 2012-03-22 | 2014-09-16 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
| KR101424978B1 (ko) * | 2012-05-24 | 2014-07-31 | 경상대학교산학협력단 | 길만시약 화합물을 이용한 헤테로 융합고리 화합물의 신규한 제조방법 |
| WO2014016219A1 (en) | 2012-07-23 | 2014-01-30 | Basf Se | Dithienobenzofuran polymers and small molecules for electronic application |
| EP2928940B1 (en) | 2012-12-04 | 2021-03-03 | CLAP Co., Ltd. | Functionalized benzodithiophene polymers for electronic application |
| US9472764B2 (en) * | 2012-12-04 | 2016-10-18 | Northwestern University | Conjugated polymers and their use in optoelectronic devices |
| JP6112717B2 (ja) * | 2013-05-13 | 2017-04-12 | 国立大学法人東京工業大学 | ジチエノゲルモール骨格を有する有機ヘテロ高分子およびその製造方法 |
| US20150047693A1 (en) * | 2013-06-28 | 2015-02-19 | New Energy Technologies, Inc. | Coatings for aircraft window surfaces to produce electricity for mission-critical systems and maintenance load on commercial aircraft |
| JP6184234B2 (ja) * | 2013-08-02 | 2017-08-23 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体薄膜および有機半導体材料 |
| CN103601740B (zh) * | 2013-09-17 | 2016-02-24 | 武汉工程大学 | 一种2,1,3-苯并噻二唑并二噻吩衍生溴代物及其合成方法 |
| JP6209099B2 (ja) * | 2014-02-10 | 2017-10-04 | 富士フイルム株式会社 | 光電変換素子およびその使用方法、光センサ、撮像素子、化合物およびその製造方法 |
| US10364317B2 (en) | 2014-09-09 | 2019-07-30 | Merck Patent Gmbh | Conjugated polymers |
| US10875957B2 (en) * | 2015-11-11 | 2020-12-29 | The Regents Of The University Of California | Fluorine substitution influence on benzo[2,1,3]thiodiazole based polymers for field-effect transistor applications |
| CN105906788B (zh) * | 2016-06-12 | 2018-06-29 | 南京邮电大学 | 含有吩嗪结构的聚合物及其制备方法和应用 |
| CN109791983B (zh) * | 2016-09-29 | 2023-06-16 | 富士胶片株式会社 | 微晶有机半导体膜、有机半导体晶体管及其制造方法 |
| US10312444B2 (en) | 2016-10-06 | 2019-06-04 | International Business Machines Corporation | Organic semiconductors with dithienofuran core monomers |
| CN106967096B (zh) * | 2017-05-17 | 2019-01-29 | 中节能万润股份有限公司 | 一种含噻吩结构的二唑类杂环化合物及其应用 |
| US20210009604A1 (en) * | 2018-05-07 | 2021-01-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd | Bifuran-imide-based materials and uses thereof |
| US11332579B1 (en) | 2021-11-19 | 2022-05-17 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovoltaics |
| US11326019B1 (en) | 2021-11-19 | 2022-05-10 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovoltaics |
| US11690283B2 (en) | 2021-11-19 | 2023-06-27 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovoltaics |
| US11849629B2 (en) | 2021-11-19 | 2023-12-19 | Phillips 66 Company | Fused dithieno benzothiadiazole polymers for organic photovolatics |
| CN114349766B (zh) * | 2021-12-20 | 2023-04-07 | 淮阴工学院 | 一种d-a-d型有机半导体材料及其制备方法和应用 |
| CN114507337A (zh) * | 2022-02-21 | 2022-05-17 | 东华大学 | 含有喹喔啉结构的共轭聚合物及其合成方法与应用 |
| CN115724873B (zh) * | 2022-11-01 | 2025-10-28 | 汕头大学 | 基于苯并二噻吩的稠环单体、其聚合物及制备方法和应用 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1459392B1 (en) | 2001-12-19 | 2011-09-21 | Merck Patent GmbH | Organic field effect transistor with an organic dielectric |
| EP1648864B1 (en) * | 2003-07-07 | 2015-08-19 | The University of Hong Kong | Photochromic diarylethene-containing coordination compounds and the production thereof |
| AU2005221648B2 (en) | 2004-03-04 | 2008-05-29 | The Procter And Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| EP2192123B1 (en) | 2006-03-10 | 2012-11-21 | Sumitomo Chemical Company, Limited | Fused tricyclic compounds useful in organic thin film devices such as transistors |
| CN101889016B (zh) | 2007-10-09 | 2014-02-12 | 巴斯夫欧洲公司 | 吡咯并吡咯衍生物、其制备及用途 |
| CN101835821B (zh) | 2007-10-25 | 2013-05-01 | 巴斯夫欧洲公司 | 作为有机半导体的酮基吡咯 |
| WO2009092671A2 (en) | 2008-01-25 | 2009-07-30 | Basf Se | Organic light emitting systems |
| EP2254929B1 (en) | 2008-03-17 | 2018-05-16 | Basf Se | Substituted oligo- or polythiophenes |
| KR101830592B1 (ko) | 2008-07-18 | 2018-02-20 | 유디씨 아일랜드 리미티드 | 전자 용품을 위한 아자피렌 |
| WO2010046259A1 (en) | 2008-10-21 | 2010-04-29 | Basf Se | Polycyclic compounds for electronic applications |
| EP2350160B1 (en) | 2008-10-31 | 2018-04-11 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| JP5583133B2 (ja) | 2008-10-31 | 2014-09-03 | ビーエーエスエフ ソシエタス・ヨーロピア | 有機電界効果トランジスタに使用するためのジケトピロロピロールポリマー |
| WO2010136353A1 (en) | 2009-05-27 | 2010-12-02 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
| EP2449561A2 (en) | 2009-06-30 | 2012-05-09 | Plextronics, Inc. | Polymers comprising at least one bithiophene repeat unit, methods synthetising said polymers and compositions comprising the same |
| US20110006287A1 (en) | 2009-07-10 | 2011-01-13 | Wei You | Polymers with tunable band gaps for photonic and electronic applications |
| CN102549791B (zh) * | 2009-08-28 | 2015-01-07 | 新加坡科技研究局 | 双极性聚合物半导体材料及有机电子器件 |
-
2010
- 2010-05-21 CN CN201080023293.5A patent/CN102449023B/zh not_active Expired - Fee Related
- 2010-05-21 JP JP2012512320A patent/JP5886190B2/ja not_active Expired - Fee Related
- 2010-05-21 EP EP10723972.5A patent/EP2435497B1/en active Active
- 2010-05-21 KR KR1020117031222A patent/KR101805203B1/ko not_active Expired - Fee Related
- 2010-05-21 US US13/322,506 patent/US9233930B2/en active Active
- 2010-05-21 WO PCT/EP2010/057038 patent/WO2010136401A2/en not_active Ceased
-
2015
- 2015-12-10 US US14/965,128 patent/US9716241B2/en not_active Expired - Fee Related
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