JP2014501695A5 - - Google Patents
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- JP2014501695A5 JP2014501695A5 JP2013530700A JP2013530700A JP2014501695A5 JP 2014501695 A5 JP2014501695 A5 JP 2014501695A5 JP 2013530700 A JP2013530700 A JP 2013530700A JP 2013530700 A JP2013530700 A JP 2013530700A JP 2014501695 A5 JP2014501695 A5 JP 2014501695A5
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- Japan
- Prior art keywords
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- alkyl
- compound
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- formula
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 42
- 150000001875 compounds Chemical class 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 239000004065 semiconductor Substances 0.000 claims 13
- 125000003118 aryl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000001931 aliphatic group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 125000004434 sulfur atom Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 3
- 125000002723 alicyclic group Chemical group 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 1
- -1 CF 3 and / or F Chemical group 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 230000005669 field effect Effects 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 238000007738 vacuum evaporation Methods 0.000 claims 1
- 0 C*N(C(c1ccc(C#N)[s]1)=C(C1=C(c2ccc(C#N)[s]2)N2**)C2=O)C1=O Chemical compound C*N(C(c1ccc(C#N)[s]1)=C(C1=C(c2ccc(C#N)[s]2)N2**)C2=O)C1=O 0.000 description 2
- HOTARSKVZZCXJW-CKCYJDGVSA-N CCCCCCC(CCCC)CN(C(c1ccc(C#N)[o]1)=C1C2=C(/C(/C)=C/C=C(/C#N)\O)N(CC(CCCC)/C=C/CCCC)[C@@H]1O)C2=O Chemical compound CCCCCCC(CCCC)CN(C(c1ccc(C#N)[o]1)=C1C2=C(/C(/C)=C/C=C(/C#N)\O)N(CC(CCCC)/C=C/CCCC)[C@@H]1O)C2=O HOTARSKVZZCXJW-CKCYJDGVSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10182051 | 2010-09-29 | ||
| EP10182051.2 | 2010-09-29 | ||
| EP11157264.0 | 2011-03-08 | ||
| EP11157264 | 2011-03-08 | ||
| PCT/EP2011/066763 WO2012041849A1 (en) | 2010-09-29 | 2011-09-27 | Semiconductors based on diketopyrrolopyrroles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014501695A JP2014501695A (ja) | 2014-01-23 |
| JP2014501695A5 true JP2014501695A5 (OSRAM) | 2014-11-13 |
| JP5921554B2 JP5921554B2 (ja) | 2016-05-24 |
Family
ID=44719925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013530700A Expired - Fee Related JP5921554B2 (ja) | 2010-09-29 | 2011-09-27 | ジケトピロロピロール系の半導体 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2621927B1 (OSRAM) |
| JP (1) | JP5921554B2 (OSRAM) |
| KR (1) | KR101880777B1 (OSRAM) |
| CN (1) | CN103140492B (OSRAM) |
| WO (1) | WO2012041849A1 (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9362508B2 (en) | 2011-06-22 | 2016-06-07 | Basf Se | Diketopyrrolopyrrole oligomers for use in organic semiconductor devices |
| CN103874742B (zh) | 2011-08-12 | 2016-08-17 | 巴斯夫欧洲公司 | 咔唑并咔唑-二(二碳酰亚胺)和它们作为半导体的用途 |
| TW201321427A (zh) * | 2011-08-19 | 2013-06-01 | Univ Washington | 基於二酮吡咯並吡咯之新型聚（雜亞芳基亞乙烯基） |
| US9209412B2 (en) | 2011-09-02 | 2015-12-08 | Basf Se | Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers |
| CN103044430B (zh) * | 2011-10-11 | 2015-04-29 | 中国科学院化学研究所 | 并吡咯二酮-噻吩醌化合物及其制备方法与应用 |
| CN103975453B (zh) | 2011-12-07 | 2018-01-30 | 巴斯夫欧洲公司 | 有机场效应晶体管 |
| CN103975454B (zh) | 2011-12-07 | 2018-02-09 | 巴斯夫欧洲公司 | 用于有机半导体器件的二酮基吡咯并吡咯聚合物 |
| JP6419065B2 (ja) | 2012-04-02 | 2018-11-07 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 電子工学用途のためのフェナントロ［９，１０−ｂ］フランポリマーおよび小分子化合物 |
| EP2834286B1 (en) | 2012-04-04 | 2019-01-23 | Basf Se | Diketopyrrolopyrrole polymers and small molecules |
| CN102675340B (zh) * | 2012-05-18 | 2015-04-01 | 中国科学院长春应用化学研究所 | 化合物、聚合物、聚合物半导体材料及有机薄膜晶体管 |
| EP2818493A1 (en) | 2013-06-25 | 2014-12-31 | Basf Se | Near infrared absorbing polymers for electronic applications |
| JP6187007B2 (ja) * | 2013-08-07 | 2017-08-30 | 株式会社リコー | 置換基脱離性ジケトピロロピロール誘導体、有機半導体材料、及び有機半導体材料膜 |
| CN105683193B (zh) * | 2013-10-28 | 2018-09-18 | 株式会社Lg化学 | 单分子和包含其的太阳能电池 |
| WO2015076171A1 (ja) * | 2013-11-21 | 2015-05-28 | 株式会社ダイセル | 有機トランジスタ製造用溶剤 |
| JP5907233B1 (ja) * | 2014-10-23 | 2016-04-26 | 東洋インキＳｃホールディングス株式会社 | 有機エレクトロルミネッセンス素子用材料およびその用途 |
| JP5907289B1 (ja) * | 2015-02-06 | 2016-04-26 | 東洋インキＳｃホールディングス株式会社 | 有機エレクトロルミネッセンス素子用材料およびその用途 |
| CN106632410B (zh) * | 2016-12-20 | 2019-04-23 | 中国科学院化学研究所 | 吡啶并噻吩基吡咯并吡咯二酮及其聚合物 |
| CN107732018B (zh) * | 2017-11-22 | 2020-08-14 | 常州大学 | 一种用于三元共混太阳能电池的活性层及其应用 |
| EP3762979A1 (en) | 2018-03-07 | 2021-01-13 | Clap Co., Ltd. | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
| JP7075682B2 (ja) | 2018-03-08 | 2022-05-26 | クラップ カンパニー リミテッド | 半導電性単層カーボンナノチューブ及び有機半導電性材料を含む有機電界効果トランジスタ |
| CN112074548B (zh) | 2018-06-26 | 2023-07-25 | Clap有限公司 | 作为电介质的乙烯醚类聚合物 |
| CN110183452B (zh) * | 2019-05-16 | 2021-06-01 | 中山大学 | 一种全氟丁基取代化合物及其制备方法和应用 |
| JP7451951B2 (ja) * | 2019-11-14 | 2024-03-19 | Ｔｏｐｐａｎホールディングス株式会社 | 着色性組成物、赤外線パスフィルター、固体撮像素子用フィルターおよび固体撮像素子 |
| CN112280010A (zh) * | 2020-11-10 | 2021-01-29 | 杭州奥得科技有限公司 | 一种基于二（并二噻吩）-吡咯并吡咯二酮与联二噻吩结构单元的共聚物及制备方法和应用 |
| WO2024107930A1 (en) * | 2022-11-16 | 2024-05-23 | Ubiquitous Energy, Inc. | Transparent photovoltaic devices including photoactive materials derived from5 diketopyrrolopyrrole |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE22104T1 (de) | 1982-05-17 | 1986-09-15 | Ciba Geigy Ag | Herstellung von pyrrolo-(3,4-c)-pyrrolen. |
| EP0184982B1 (de) | 1984-11-07 | 1991-01-23 | Ciba-Geigy Ag | Verfahren zur Herstellung von Pyrrolo-[3,4-c]-pyrrolen und neue Pyrrolo-[3,4-c]-pyrrole |
| US5703436A (en) | 1994-12-13 | 1997-12-30 | The Trustees Of Princeton University | Transparent contacts for organic devices |
| US6420031B1 (en) | 1997-11-03 | 2002-07-16 | The Trustees Of Princeton University | Highly transparent non-metallic cathodes |
| AT411306B (de) | 2000-04-27 | 2003-11-25 | Qsel Quantum Solar Energy Linz | Photovoltaische zelle mit einer photoaktiven schicht aus zwei molekularen organischen komponenten |
| US20030021913A1 (en) | 2001-07-03 | 2003-01-30 | O'neill Mary | Liquid crystal alignment layer |
| US20040004433A1 (en) | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
| KR101130094B1 (ko) | 2003-04-10 | 2012-03-28 | 시바 홀딩 인크 | 형광성 디케토피롤로피롤 |
| DE10326547A1 (de) | 2003-06-12 | 2005-01-05 | Siemens Ag | Tandemsolarzelle mit einer gemeinsamen organischen Elektrode |
| US7194173B2 (en) | 2004-07-16 | 2007-03-20 | The Trustees Of Princeton University | Organic devices having a fiber structure |
| JP2006117591A (ja) | 2004-10-22 | 2006-05-11 | Toyo Ink Mfg Co Ltd | 蛍光性ジケトピロロピロール化合物 |
| US20070079867A1 (en) | 2005-10-12 | 2007-04-12 | Kethinni Chittibabu | Photovoltaic fibers |
| JP2007266285A (ja) * | 2006-03-28 | 2007-10-11 | Nippon Kayaku Co Ltd | 電界効果トランジスタ |
| 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 |
| CN101479272B (zh) * | 2006-06-30 | 2014-11-19 | 西巴控股有限公司 | 作为有机半导体的二酮基吡咯并吡咯聚合物 |
| KR100918362B1 (ko) * | 2006-07-27 | 2009-09-22 | 주식회사 엘지화학 | 유기 박막 트랜지스터 및 이의 제조방법 |
| JP2008078247A (ja) * | 2006-09-19 | 2008-04-03 | Toyo Ink Mfg Co Ltd | 有機トランジスタ |
| WO2008044302A1 (en) * | 2006-10-12 | 2008-04-17 | Toyo Ink Mfg. Co., Ltd. | Organic transistor |
| US7910684B2 (en) | 2007-09-06 | 2011-03-22 | Xerox Corporation | Diketopyrrolopyrrole-based derivatives for thin film transistors |
| US8404864B2 (en) * | 2007-10-09 | 2013-03-26 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use |
| WO2010049321A1 (en) * | 2008-10-31 | 2010-05-06 | Basf Se | Diketopyrrolopyrrole polymers for use in organic field effect transistors |
| JP5635070B2 (ja) | 2009-03-23 | 2014-12-03 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 有機半導体デバイスでの使用のためのジケトピロロピロールポリマー |
-
2011
- 2011-09-27 KR KR1020137010758A patent/KR101880777B1/ko not_active Expired - Fee Related
- 2011-09-27 WO PCT/EP2011/066763 patent/WO2012041849A1/en not_active Ceased
- 2011-09-27 JP JP2013530700A patent/JP5921554B2/ja not_active Expired - Fee Related
- 2011-09-27 CN CN201180047342.3A patent/CN103140492B/zh not_active Expired - Fee Related
- 2011-09-27 EP EP11761589.8A patent/EP2621927B1/en active Active