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Development of amphiphilic thienoisoindigo polymers and investigation of device performance based on fiber formation

Research Project

Project/Area Number 26410087
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Functional solid state chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Ashizawa Minoru  東京工業大学, 物質理工学院, 助教 (80391845)

Co-Investigator(Kenkyū-buntansha) 松本 英俊  東京工業大学, 物質理工学院, 准教授 (40345393)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2015: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2014: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords有機半導体 / チエノイソインジゴ / 電界効果トランジスタ / 機能性有機半導体 / 有機合成 / 有機電界効果トランジスタ / 近赤外光熱電変換素子 / 有機デバイス / 光熱電変換素子 / 有機薄膜太陽電池
Outline of Final Research Achievements

In this study, we have designed and synthesized hole-transport thienoisoindigo (TII) based polymers bearing near infrared region absorption arising from narrow energy gap. The long wavelength absorption specifically characteristic of TII polymers is coming from quinoidal structure of TII unit. In addition, we have developed useful synthetic approach for large scale preparation of H-intact TII unit at the N-position. Of particular note is that H-intact TII unit has the synthetic diversity to attaching various types of solubilizing side-chain groups. In the single crystal, H-intact TII form densely packed two-dimensional conduction path via intermolecular hydrogen-bonding, resulting in higher ambipolar performance in organic field effect transistors (OFETs) than that of N-substituted TII. Notably, H-intact TII substituted with flanking phenyl group exhibits well balanced hole and electron mobilities of 0.1 cm2/Vs.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (31 results)

All 2017 2016 2015 2014 Other

All Int'l Joint Research (1 results) Journal Article (6 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 6 results,  Open Access: 3 results,  Acknowledgement Compliant: 5 results) Presentation (23 results) (of which Int'l Joint Research: 7 results) Remarks (1 results)

  • [Int'l Joint Research] Department of Chemical Engneering/Stanford University(米国)

    • Related Report
      2015 Research-status Report
  • [Journal Article] N-unsubstituted thienoisoindigos: preparation, molecular packing and ambipolar organic field-effect transistors2017

    • Author(s)
      Dongho Yoo, Tsukasa Hasegawa, Minoru Ashizawa, Tadashi Kawamoto, Hiroyasu Masunaga, Takaaki Hikima, Hidetoshi Matsumoto, and Takehiko Mori
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 5 Issue: 10 Pages: 2509-2512

    • DOI

      10.1039/c7tc00327g

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Influence of structure-property relationships of two structural isomers of thiophene-flanked diazaisoindigo on carrier-transport properties2016

    • Author(s)
      Minoru Ashizawa, Tsukasa Hasegawa, Susumu Kawauchi, Hiroyasu Masunaga, Takaaki Hikima, and Hidetoshi Matsumoto
    • Journal Title

      RSC Advances

      Volume: 6 Issue: 111 Pages: 109434-109441

    • DOI

      10.1039/c6ra17424h

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Ambipolar Organic Transistors Based on Isoindigo Derivatives2016

    • Author(s)
      Minoru Ashizawa, Naoaki Masuda, Toshiki Higashino, Tomofumi Kadoya, Tadashi Kawamoto, Hidetoshi Matsumoto, Takehiko Mori
    • Journal Title

      Org. Electron.

      Volume: 35 Pages: 95-100

    • DOI

      10.1016/j.orgel.2016.05.013

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] An ultra-narrow bandgap derived from thienoisoindigo polymers: structural influence on reducing bandgap and self-organization2016

    • Author(s)
      Tsukasa Hasegawa, Minoru Ashizawa, Junya Hiyoshi, Susumu Kawauchi, Jianguo Mei, Zhenan Bao, and Hidetoshi Matsumoto
    • Journal Title

      Polymer Chemistry

      Volume: 7 Issue: 5 Pages: 1181-1190

    • DOI

      10.1039/c5py01870f

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Quinoxalineimide as a novel electron-accepting building block for organic optoelectronics2015

    • Author(s)
      Tsukasa Hasegawa, Koutarou Aoyagi, Minoru Ashizawa, Yuichi Konosu, Susumu Kawauchi, Niyazi Serdar Sariciftci, and Hidetoshi Matsumoto
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 8 Pages: 1128-1130

    • DOI

      10.1246/cl.150407

    • NAID

      130005092581

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Design and structure-property relationship of benzothienoisoindigo in organic field effect transistors2015

    • Author(s)
      Tsukasa Hasegawa, Minoru Ashizawa, and Hidetoshi Matsumoto
    • Journal Title

      RSC Advances

      Volume: 5 Issue: 75 Pages: 61035-61043

    • DOI

      10.1039/c5ra07660a

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] キノキサリンイミド誘導体を用いた大気安定n型半導体ポリマーの合成と物性2017

    • Author(s)
      長谷川司, 芦沢実, 川内進, 松本英俊
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 水素原子を残したチエノイソインジゴ誘導体の合成と物性2017

    • Author(s)
      芦沢実, 長谷川司, 劉東昊, 川本正, 松本英俊, 森健彦
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 狭エネルギーギャップポリマーを用いた近赤外光熱電変換素子の作製2017

    • Author(s)
      長谷川司, 芦沢実, 間中孝彰, 川内進, 松本英俊
    • Organizer
      第64回応用物理学会春季学術講演会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2017-03-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] Ambipolar organic field-effect transistors based on thienoisoindigo analogs2016

    • Author(s)
      D. Yoo, T. Hasegawa, M. Ashizawa, T. Kawamoto, H. Matsumoto, T. Mori
    • Organizer
      12th Japan-China Joint Symposium on Conduction and Photoconduction in Organic Solids and Related Phenomena
    • Place of Presentation
      Waseda University
    • Year and Date
      2016-10-17
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] p型およびn型狭エネルギーギャップポリマーの合成と近赤外光熱電変換素子への応用2016

    • Author(s)
      長谷川司, 芦沢実, 間中孝彰, 川内進, 松本英俊
    • Organizer
      第65回高分子討論会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2016-09-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] チエノイソインジゴ類縁体を用いた有機電界効果トランジスタ2016

    • Author(s)
      劉東昊, 長谷川司, 芦沢実, 川本正, 松本英俊, 森健彦
    • Organizer
      第10回分子科学討論会
    • Place of Presentation
      神戸ファッションマート
    • Year and Date
      2016-09-13
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis and characterization of diazaisoindigo-based molecules: impact of the connection modes on carrier-transport properties2016

    • Author(s)
      M. Ashizawa, T. Hasegawa, S. Kawauchi, H. Masunaga, T. Hikima, H. Matsumoto
    • Organizer
      The 7th International Conference on Flexible and Printed Electronics (ICFPE 2016)
    • Place of Presentation
      Yamagata University
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of n-type thiaziazole-fused quinoxalineimide: structural characterization and field-effect transistor application2016

    • Author(s)
      T. Hasegawa, M. Ashizawa, H. Masunaga, T. Hikima, H. Matsumoto
    • Organizer
      The 7th International Conference on Flexible and Printed Electronics (ICFPE 2016)
    • Place of Presentation
      Yamagata University
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis, characterization, and carrier-transport properties of diazaisoindigo-based conjugated polymers2016

    • Author(s)
      M. Ashizawa, T. Hasegawa, S. Kawauchi, H. Masunaga, T. Hikima, H. Matsumoto
    • Organizer
      International Conference on the Science and Technology of Synthetic Metals (ICSM2016)
    • Place of Presentation
      Guangzhou, China
    • Year and Date
      2016-06-26
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] チアジアゾロキノキサリンイミド骨格を有する大気安定n型半導体ポリマーの合成とキャリア輸送特性2016

    • Author(s)
      長谷川司, 芦沢実, 青柳晃太朗, 川内進, 松本英俊
    • Organizer
      第63回応用物理学会春季学術講演会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2016-03-19
    • Related Report
      2015 Research-status Report
  • [Presentation] ヘテロ環式イソインジゴ類縁体を用いた有機電界効果トランジスタ2016

    • Author(s)
      劉東昊, 増田直彰, 芦沢実, 川本正, 松本英俊, 森健彦
    • Organizer
      第63回応用物理学会春季学術講演会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2016-03-19
    • Related Report
      2015 Research-status Report
  • [Presentation] Organic field-effect transistors based on isoindigo derivatives2015

    • Author(s)
      N. Masuda, T. Higashino, T. Kadoya, M. Ashizawa, T. Kawamoto, H. Matsumoto, T. Mori
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (Pacifichem 2015)
    • Place of Presentation
      Honolulu, HI, United States
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Structural influence on carrier transport of ultra-narrow bandgap polymers derived from thienoisoindigo2015

    • Author(s)
      T. Hasegawa, M. Ashizawa, J. Hiyoshi, S. Kawauchi, J. Mei, Z. Bao, H. Matsumoto
    • Organizer
      2015 MRS Fall Meeting & Exhibit
    • Place of Presentation
      Boston, MA, United States
    • Year and Date
      2015-11-29
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Polymer semiconductor nanofiber networks for enhancement of carrier mobility and stability of organic photovoltaic devices2015

    • Author(s)
      H. Matsumoto, Y. Konosu, S. Inagaki, M. Ashizawa, A. Tanioka
    • Organizer
      2015 MRS Fall Meeting & Exhibit
    • Place of Presentation
      Boston, MA, United States
    • Year and Date
      2015-11-29
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] イソインジゴを活性層に用いた有機電界効果トランジスタ2015

    • Author(s)
      増田直彰, 東野寿樹, 角屋智史, 芦沢実, 川本正, 松本英俊, 森健彦
    • Organizer
      第9回分子科学討論会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2015-09-16
    • Related Report
      2015 Research-status Report
  • [Presentation] 新規ベンゾチエノイソインジゴ骨格の合成とキャリア輸送特性2015

    • Author(s)
      長谷川司, 芦沢実, 松本英俊
    • Organizer
      第9回分子科学討論会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2015-09-16
    • Related Report
      2015 Research-status Report
  • [Presentation] ジアザイソインジゴ骨格を用いた誘導体の構造と物性2015

    • Author(s)
      芦沢実, 長谷川司, 日吉淳也, 川内進, 松本英俊
    • Organizer
      第9回分子科学討論会
    • Place of Presentation
      東京工業大学大岡山キャンパス
    • Year and Date
      2015-09-16
    • Related Report
      2015 Research-status Report
  • [Presentation] 狭バンドギャップポリマーへの展開を目指した高平面性チエノイソインジゴオリゴマーの電子構造と光学特性における鎖長依存性の検討2015

    • Author(s)
      長谷川司, 芦沢実, 日吉淳也, 川内進, 松本英俊
    • Organizer
      第64回高分子学会年次大会
    • Place of Presentation
      札幌コンベンションセンター
    • Year and Date
      2015-05-27
    • Related Report
      2015 Research-status Report
  • [Presentation] キノキサリンイミド骨格を有する新規D-A-D型有機半導体材料の合成と有機薄膜太陽電池への応用2015

    • Author(s)
      青柳晃太郎, 芦沢実, 鴻巣裕一, 松本英俊
    • Organizer
      第62回応用物理学会春季学術講演会
    • Place of Presentation
      東海大学湘南キャンパス
    • Year and Date
      2015-03-11 – 2015-03-15
    • Related Report
      2014 Research-status Report
  • [Presentation] キノキサリンイミド骨格を縮合したジベンゾTTFアクセプターの合成とBHJ型太陽電池への応用2014

    • Author(s)
      芦沢実, 長谷川司, 鴻巣裕一, 日吉淳也, 川内進, 松本英俊
    • Organizer
      第8回分子科学討論会
    • Place of Presentation
      広島大学東広島キャンパス
    • Year and Date
      2014-09-21 – 2014-09-24
    • Related Report
      2014 Research-status Report
  • [Presentation] チエノイソインジゴ骨格を有するD-A型オリゴマーの合成と物性2014

    • Author(s)
      長谷川司, 芦沢実, 松本英俊
    • Organizer
      第8回分子科学討論会
    • Place of Presentation
      広島大学東広島キャンパス
    • Year and Date
      2014-09-21 – 2014-09-24
    • Related Report
      2014 Research-status Report
  • [Presentation] イソインジゴ誘導体を活性層に用いた有機電界効果トランジスタ2014

    • Author(s)
      増田直彰, 東野寿樹, 角屋智史, 小田島岳史, 芦沢実, 川本正, 松本英俊, 森健彦
    • Organizer
      第8回分子科学討論会
    • Place of Presentation
      広島大学東広島キャンパス
    • Year and Date
      2014-09-21 – 2014-09-24
    • Related Report
      2014 Research-status Report
  • [Presentation] チエノイソインジゴ骨格を有する新規半導体ポリマーの合成と物性2014

    • Author(s)
      長谷川司, 芦沢実, 日吉淳也, 川内進, 松本英俊
    • Organizer
      第63回高分子学会年次大会
    • Place of Presentation
      名古屋国際会議場
    • Year and Date
      2014-05-28 – 2014-05-30
    • Related Report
      2014 Research-status Report
  • [Remarks] 光を熱に変えるプラスチックフィルムで発電に成功 ~生体内発電に新たな“光”

    • URL

      http://main.spsj.or.jp/koho/65t/65t_2.pdf

    • Related Report
      2016 Annual Research Report

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Published: 2014-04-04   Modified: 2022-01-27  

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