JP2013525514A5 - - Google Patents
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- Publication number
- JP2013525514A5 JP2013525514A5 JP2013501344A JP2013501344A JP2013525514A5 JP 2013525514 A5 JP2013525514 A5 JP 2013525514A5 JP 2013501344 A JP2013501344 A JP 2013501344A JP 2013501344 A JP2013501344 A JP 2013501344A JP 2013525514 A5 JP2013525514 A5 JP 2013525514A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- aryl
- independently
- optionally substituted
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000001188 haloalkyl group Chemical group 0.000 claims description 40
- 239000004065 semiconductor Substances 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 239000010409 thin film Substances 0.000 claims description 13
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000003106 haloaryl group Chemical group 0.000 claims description 6
- 230000005693 optoelectronics Effects 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229920005603 alternating copolymer Polymers 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- -1 pyrrolo [3,2-b] pyrrole-2,5 (1H, 4H) -dione-3,6-diyl moiety Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 3
- 239000002356 single layer Substances 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229920005604 random copolymer Polymers 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims 2
- 125000000962 organic group Chemical group 0.000 claims 1
- 0 CC(C)(C(C)(CC1)C*1(C)C(C)(C)[Al]C)[Al] Chemical compound CC(C)(C(C)(CC1)C*1(C)C(C)(C)[Al]C)[Al] 0.000 description 26
- 239000000203 mixture Substances 0.000 description 7
- 230000005669 field effect Effects 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 239000003989 dielectric material Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FFYCHOLHKRDMDL-UHFFFAOYSA-N CC(C)(C1(C)CCC(C)(C)CC1)[AlH2] Chemical compound CC(C)(C1(C)CCC(C)(C)CC1)[AlH2] FFYCHOLHKRDMDL-UHFFFAOYSA-N 0.000 description 1
- DKHDQTBBXQMFPP-UHFFFAOYSA-N Cc1ccc(-c2ccc(C)[s]2)[s]1 Chemical compound Cc1ccc(-c2ccc(C)[s]2)[s]1 DKHDQTBBXQMFPP-UHFFFAOYSA-N 0.000 description 1
- GWQOOADXMVQEFT-UHFFFAOYSA-N Cc1ccc(C)[s]1 Chemical compound Cc1ccc(C)[s]1 GWQOOADXMVQEFT-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31591110P | 2010-03-20 | 2010-03-20 | |
| US61/315,911 | 2010-03-20 | ||
| PCT/US2011/029112 WO2011119446A1 (en) | 2010-03-20 | 2011-03-19 | Pyrrolo[3,2-b]pyrrole semiconducting compounds and devices incorporating same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013525514A JP2013525514A (ja) | 2013-06-20 |
| JP2013525514A5 true JP2013525514A5 (OSRAM) | 2014-05-08 |
| JP5588559B2 JP5588559B2 (ja) | 2014-09-10 |
Family
ID=44065288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013501344A Active JP5588559B2 (ja) | 2010-03-20 | 2011-03-19 | ピロロ［３，２−ｂ］ピロール半導体化合物およびそれを組み込んだデバイス |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8598448B2 (OSRAM) |
| EP (1) | EP2550688B1 (OSRAM) |
| JP (1) | JP5588559B2 (OSRAM) |
| CN (1) | CN102893422B (OSRAM) |
| WO (1) | WO2011119446A1 (OSRAM) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI511997B (zh) * | 2009-05-21 | 2015-12-11 | Raynergy Tek Inc | 共軛聚合物及其於光電子裝置的用途 |
| TWI510488B (zh) * | 2010-09-13 | 2015-12-01 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent elements |
| EP2630676B1 (en) | 2010-10-22 | 2015-03-04 | Raynergy Tek Inc. | Conjugated polymers and their use in optoelectronic devices |
| US8598450B2 (en) | 2010-11-24 | 2013-12-03 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
| DE112011104436T5 (de) * | 2010-12-17 | 2013-09-12 | Merck Patent Gmbh | Konjugierte Polymere |
| JP2014515043A (ja) * | 2011-03-11 | 2014-06-26 | 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 | 共役ポリマー |
| JP2014516468A (ja) * | 2011-03-25 | 2014-07-10 | 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 | ピロロ［３，２−ｂ］ピロール−２，５−ジオンおよび有機半導体としてのそれらの使用 |
| EP2692761A4 (en) * | 2011-03-31 | 2014-09-17 | Kuraray Co | BLOCK COPOLYMER AND PHOTOELECTRIC CONVERSION ELEMENT |
| JP6165135B2 (ja) * | 2011-06-22 | 2017-07-19 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 有機半導体素子内で使用するためのジケトピロロピロールオリゴマー |
| JP5786504B2 (ja) * | 2011-07-08 | 2015-09-30 | 住友化学株式会社 | 高分子化合物及びそれを用いた有機光電変換素子 |
| 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） |
| ITMI20120284A1 (it) * | 2012-02-27 | 2013-08-28 | E T C Srl | Transistor ambipolare elettroluminescente organico ad effetto di campo ad emissione luminosa distribuita |
| US8835598B2 (en) | 2012-03-22 | 2014-09-16 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
| EP2650938A1 (en) * | 2012-04-13 | 2013-10-16 | Acreo Swedish ICT AB | Organic Field-Effect Transistor Device |
| EP2680336A1 (en) * | 2012-06-25 | 2014-01-01 | Tata Steel Nederland Technology B.V. | Photoactive material having an imide based conjugated backbone |
| US9029695B2 (en) * | 2013-02-24 | 2015-05-12 | Raynergy Tek Inc. | Heteroaromatic semiconducting polymers |
| CN103214490A (zh) * | 2013-03-25 | 2013-07-24 | 中国科学院青岛生物能源与过程研究所 | 一种新型有机场效应晶体管材料的制备方法 |
| EP2818493A1 (en) * | 2013-06-25 | 2014-12-31 | Basf Se | Near infrared absorbing polymers for electronic applications |
| CN105131640B (zh) * | 2015-07-28 | 2017-10-20 | 华南理工大学 | 异吡咯并吡咯二酮染料及其应用 |
| KR102069406B1 (ko) * | 2016-03-21 | 2020-01-22 | 주식회사 엘지화학 | 가스센서 |
| WO2018076247A1 (en) * | 2016-10-27 | 2018-05-03 | South University Of Science And Technology Of China | A weak electron-donating building block, copolymers thereof and their preparation methods as well as their applications |
| US12256588B2 (en) | 2019-04-18 | 2025-03-18 | The University Of North Carolina At Chapel Hill | Perovskite solar cells with near-infrared sensitive layers |
| WO2024003969A1 (en) * | 2022-06-27 | 2024-01-04 | Koala Tech Inc. | Organic solid-state laser, compound and use thereof |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0163609A3 (de) * | 1984-05-30 | 1987-05-13 | Ciba-Geigy Ag | Verfahren zum Färben von hochmolekularem organischem Material, neue polycyclische Verbindungen sowie deren Herstellung |
| DE3525109A1 (de) | 1985-07-13 | 1987-01-15 | Bayer Ag | Heterocyclische vrbindungen |
| TWI290164B (en) * | 1999-08-26 | 2007-11-21 | Ciba Sc Holding Ag | DPP-containing conjugated polymers and electroluminescent devices |
| JP4089472B2 (ja) * | 2003-03-10 | 2008-05-28 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| JP4093083B2 (ja) * | 2003-03-10 | 2008-05-28 | 東洋インキ製造株式会社 | 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子 |
| US7939818B2 (en) | 2003-10-28 | 2011-05-10 | Basf Se | Diketopyrrolopyrrole polymers |
| WO2007003520A1 (en) * | 2005-07-05 | 2007-01-11 | Ciba Specialty Chemicals Holding Inc. | Fluorescent diketopyrrolopyrroles and derivatives |
| CA2655076A1 (en) | 2006-06-30 | 2008-01-03 | Ciba Holding Inc. | Diketopyrrolopyrrole polymers as organic semiconductors |
| US7910684B2 (en) * | 2007-09-06 | 2011-03-22 | Xerox Corporation | Diketopyrrolopyrrole-based derivatives for thin film transistors |
| US7932344B2 (en) | 2007-09-06 | 2011-04-26 | Xerox Corporation | Diketopyrrolopyrrole-based polymers |
| JP5431340B2 (ja) | 2007-10-09 | 2014-03-05 | ビーエーエスエフ ソシエタス・ヨーロピア | ピロロピロール誘導体、その製造及び使用 |
| EP2350161B1 (en) | 2008-10-31 | 2018-11-21 | Basf Se | Diketopyrrolopyrrole polymers for use in organic field effect transistors |
| KR101754432B1 (ko) | 2009-03-23 | 2017-07-05 | 바스프 에스이 | 유기 반도체 장치에 사용하기 위한 디케토피롤로피롤 중합체 |
| TWI511997B (zh) | 2009-05-21 | 2015-12-11 | Raynergy Tek Inc | 共軛聚合物及其於光電子裝置的用途 |
| US8598450B2 (en) | 2010-11-24 | 2013-12-03 | Polyera Corporation | Conjugated polymers and their use in optoelectronic devices |
| JP2014515043A (ja) | 2011-03-11 | 2014-06-26 | 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 | 共役ポリマー |
-
2011
- 2011-03-19 CN CN201180024713.6A patent/CN102893422B/zh active Active
- 2011-03-19 JP JP2013501344A patent/JP5588559B2/ja active Active
- 2011-03-19 EP EP11711227.6A patent/EP2550688B1/en active Active
- 2011-03-19 WO PCT/US2011/029112 patent/WO2011119446A1/en not_active Ceased
- 2011-03-19 US US13/052,055 patent/US8598448B2/en active Active
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