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Development of high-performance quinoid-based semiconducting polymers

Research Project

Project/Area Number 20K22535
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeMulti-year Fund
Review Section 0501:Physical chemistry, functional solid state chemistry, organic chemistry, polymers, organic materials, biomolecular chemistry, and related fields
Research InstitutionHiroshima University

Principal Investigator

Mikie Tsubasa  広島大学, 先進理工系科学研究科(工), 助教 (40881280)

Project Period (FY) 2020-09-11 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2021: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords有機半導体材料 / π共役系ポリマー / 半導体ポリマー / キノイド骨格 / 有機電界効果トランジスタ / 有機エレクトロニクス / 有機半導体 / 主鎖内伝導 / 結合交替
Outline of Research at the Start

優れた電荷輸送性を示すπ共役系ポリマーの開発は、有機デバイスの高性能化において重要課題の1つである。従来、π-π相互作用向上により高い「主鎖間伝導」を持つポリマーが多数開発されてきたが、本研究では、ポリマー主鎖の共役長拡張による「主鎖内伝導」の向上に着目した。共役長拡張の有効な手段であるキノイド骨格の導入により、高い主鎖内伝導と主鎖間伝導を両立する「高性能電荷輸送ポリマー」の創出を目指す。

Outline of Final Research Achievements

Rational design of π-conjugated polymers for improving “intrachain” charge carrier transport along the backbone still remains a formidable challenge. In this study, we designed and synthesized new π-conjugated polymers based on non-fused and fused ring quinoid structures. Careful investigation of electronic properties, associated with the structural analysis of the model compounds, structural orders, and theoretical band simulations suggested that highly π-electron delocalization along the π-conjugated backbone resulted in the greatly improved intrachain charge carrier transport and thus the remarkably high mobility in the π-conjugated polymer. We believe that our study would provide new guidelines for the design of π-conjugated polymers with high intrachain charge carrier transport.

Academic Significance and Societal Importance of the Research Achievements

従来のポリマー主鎖間の電荷輸送性を改善するという開発指針に基づいた研究では、π共役系ポリマーの電荷移動度は頭打ちになりつつあった。本研究成果により、ポリマー主鎖内の電荷輸送性向上が可能となったことで、今後、さらにπ共役系ポリマーの高移動度化が進むことが期待される。高移動度ポリマーの開発により、有機トランジスタのみならず有機薄膜太陽電池や有機熱電変換素子など、様々なプリンテッドデバイスの性能が飛躍的に向上し、IoT社会、低炭素化社会実現に大きく貢献することができる。

Report

(3 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • Research Products

    (30 results)

All 2022 2021 2020 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Open Access: 2 results) Presentation (16 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Naphthobispyrazine Bisimide: A Strong Acceptor Unit for Conjugated Polymers Enabling Highly Coplanar Backbone, Short π-π Stacking, and High Electron Transport2022

    • Author(s)
      Mikie Tsubasa、Okamoto Kenta、Iwasaki Yuka、Koganezawa Tomoyuki、Sumiya Masatomo、Okamoto Toshihiro、Osaka Itaru
    • Journal Title

      Chemistry of Materials

      Volume: 34 Issue: 6 Pages: 2717-2729

    • DOI

      10.1021/acs.chemmater.1c04196

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Naphthobisthiadiazole-Based π-Conjugated Polymers for Nonfullerene Solar Cells: Suppressing Intermolecular Interaction Improves Photovoltaic Performance2022

    • Author(s)
      Chou Li-Hui、Mikie Tsubasa、Saito Masahiko、Liu Cheng-Liang、Osaka Itaru
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 14 Issue: 12 Pages: 14400-14409

    • DOI

      10.1021/acsami.2c01606

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] N-type Semiconducting Polymers Based on Dicyano Naphthobisthiadiazole: High Electron Mobility with Unfavorable Backbone Twist2021

    • Author(s)
      Iguchi Keitaro、Mikie Tsubasa、Saito Masahiko、Komeyama Kimihiro、Seo Takuji、Ie Yutaka、Osaka Itaru
    • Journal Title

      Chemistry of Materials

      Volume: 33 Issue: 6 Pages: 2218-2228

    • DOI

      10.1021/acs.chemmater.1c00204

    • Related Report
      2021 Annual Research Report 2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Bithiazole Dicarboxylate Ester: An Easily Accessible Electron-Deficient Building Unit for π-Conjugated Polymers Enabling Electron Transport2021

    • Author(s)
      Teshima Yoshikazu、Saito Masahiko、Mikie Tsubasa、Komeyama Kimihiro、Osaka Itaru
    • Journal Title

      Macromolecules

      Volume: 54 Issue: 7 Pages: 3489-3497

    • DOI

      10.1021/acs.macromol.1c00080

    • Related Report
      2021 Annual Research Report 2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Effect of Ester Side Chains on Photovoltaic Performance in Thiophene-Thiazolothiazole Copolymers2021

    • Author(s)
      Yamanaka Kodai、Saito Masahiko、Mikie Tsubasa、Osaka Itaru
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 8 Pages: 2019-2027

    • DOI

      10.1246/bcsj.20210172

    • NAID

      130008087845

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Extended π-Electron Delocalization in Quinoid-Based Conjugated Polymers Boosts Intrachain Charge Carrier Transport2021

    • Author(s)
      Mikie Tsubasa、Hayakawa Masahiro、Okamoto Kenta、Iguchi Keitaro、Yashiro Shuhei、Koganezawa Tomoyuki、Sumiya Masatomo、Ishii Hiroyuki、Yamaguchi Shigehiro、Fukazawa Aiko、Osaka Itaru
    • Journal Title

      Chemistry of Materials

      Volume: 33 Issue: 21 Pages: 8183-8193

    • DOI

      10.1021/acs.chemmater.1c02072

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pronounced Backbone Coplanarization by π-Extension in a Sterically Hindered Conjugated Polymer System Leads to Higher Photovoltaic Performance in Non-Fullerene Solar Cells2021

    • Author(s)
      Nakao Naoya、Ogawa Soichiro、Kim Hyung Do、Ohkita Hideo、Mikie Tsubasa、Saito Masahiko、Osaka Itaru
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 13 Issue: 47 Pages: 56420-56429

    • DOI

      10.1021/acsami.1c17199

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Controlled steric selectivity in molecular doping towards closest-packed supramolecular conductors2020

    • Author(s)
      Kohno Shinya、Yamashita Yu、Kasuya Naotaka、Mikie Tsubasa、Osaka Itaru、Takimiya Kazuo、Takeya Jun、Watanabe Shun
    • Journal Title

      Communications Materials

      Volume: 1 Issue: 1 Pages: 1-6

    • DOI

      10.1038/s43246-020-00081-3

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Small-bandgap quinoid-based π-conjugated polymers2020

    • Author(s)
      Mikie Tsubasa、Osaka Itaru
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 8 Issue: 41 Pages: 14262-14288

    • DOI

      10.1039/d0tc01041c

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Presentation] 非フラーレン型太陽電池において低電圧損失と高電流を両立するπ共役系ポリマー2022

    • Author(s)
      三木江 翼、駿河 翔太、石川 巧、キム ヒョンド、大北 英生、尾坂 格
    • Organizer
      第69回応用物理学会春季学術講演会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 高効率有機薄膜太陽電池へ向けたジチエノナフトビスチアジアゾール系半導体ポリマーの開発2022

    • Author(s)
      駿河 翔太、三木江 翼、石川 巧、キム ヒョンド、大北 英生、尾坂 格
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ナフトビスチアジアゾールを基調とする新規縮環π拡張骨格とそれを有するπ共役系ポリマーの合成2022

    • Author(s)
      藤田 知勇、三木江 翼、尾坂 格
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ナフトビスピラジンを有するπ共役系ポリマーの開発と有機デバイスへの応用2021

    • Author(s)
      三木江 翼、岡本 健太、尾坂格
    • Organizer
      第14回有機π電子系シンポジウム
    • Related Report
      2021 Annual Research Report
  • [Presentation] ジチエノベンゾジチオフェンジオン骨格を有する狭バンドギャップポリマーの合成と物性2021

    • Author(s)
      岩﨑 優佳、三木江 翼、斎藤 慎彦、尾坂 格
    • Organizer
      日本化学会 第101春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] A novel semiconducting polymer based on dithienonaphthobisthiadiazole that enables high fill factor of 0.8 with thick organic solar cells2021

    • Author(s)
      Tsubasa Mikie, Itaru Osaka
    • Organizer
      FSE 若手 2nd event
    • Related Report
      2021 Annual Research Report
  • [Presentation] Thick-Film Polymer Solar cells with Excellent Fill Factor2021

    • Author(s)
      Tsubasa Mikie, Itaru Osaka
    • Organizer
      The 38th International Conference of Photopolymer Science and Technology (38th ICPST)
    • Related Report
      2021 Annual Research Report
  • [Presentation] 高効率有機薄膜太陽電池を目指した ジチエノナフトビスチアジアゾール系ポリマーの開発2021

    • Author(s)
      三木江 翼、駿河 翔太、森奥 友和、キム ヒョンド、大北 英生、尾坂 格
    • Organizer
      第70回高分子討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] S-ペックマン骨格を基調とする半導体ポリマーにおけるアルキル基が トランジスタ特性に及ぼす影響2021

    • Author(s)
      井口 景太郎、三木江 翼、尾坂 格
    • Organizer
      第70回高分子討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] フィルファクター0.8を示す厚膜有機太陽電池2021

    • Author(s)
      三木江 翼、キム ヒョンド、大北 英生、尾坂 格
    • Organizer
      第82回応用物理学会秋季学術講演会
    • Related Report
      2021 Annual Research Report
  • [Presentation] キノイド骨格を有する無色透明有機半導体の開発2021

    • Author(s)
      岩﨑 優佳、三木江 翼、尾坂 格
    • Organizer
      第82回応用物理学会秋季学術講演会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Dithienonaphothobisthiadiazole-Based π-Conjugated Polymers for High-Efficiency Organic Solar Cells2021

    • Author(s)
      Tsubasa Mikie
    • Organizer
      2021 Materials Research Society-Taiwan International Conference (2021 MRSTIC)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 半導体ポリマーの高性能化に向けた新たな分子デザイン手法の開拓2021

    • Author(s)
      三木江 翼
    • Organizer
      第3回ナノ茶論オンラインセミナー
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Extended π-conjugation in quinoidal bithiophenedione-based polymers leads to high charge transport along the main chain2021

    • Author(s)
      Tsubasa Mikie, Masahiro Hayakawa, Aiko Fukazawa, Shigehiro Yamaguchi, Itaru Osaka
    • Organizer
      International Conference on the Science and Technology of Synthetic Metals 2021
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research
  • [Presentation] ナフトビスピラジンを有するπ共役系ポリマーの開発と 有機デバイスへの応用2021

    • Author(s)
      三木江 翼、岡本 健太、尾坂 格
    • Organizer
      第14回 有機π電子系シンポジウム
    • Related Report
      2020 Research-status Report
  • [Presentation] エステル基とイミド基を有するキノキサリンを基調とした π共役系ポリマーの合成とn型半導体特性2020

    • Author(s)
      三木江 翼、岡本 健太、手島 慶和、尾坂 格
    • Organizer
      第80回秋季応用物理学会
    • Related Report
      2020 Research-status Report
  • [Remarks] 研究室ウェブサイト

    • URL

      https://osaka.hiroshima-u.ac.jp

    • Related Report
      2021 Annual Research Report
  • [Remarks] 個人ウェブサイト

    • URL

      https://mikie.hiroshima-u.ac.jp

    • Related Report
      2021 Annual Research Report
  • [Remarks] 尾坂研究室ホームページ

    • URL

      https://osaka.hiroshima-u.ac.jp/

    • Related Report
      2020 Research-status Report
  • [Patent(Industrial Property Rights)] 高分子化合物及びその製造方法、並びにそれを用いた有機薄膜太陽電池及び有機トランジスタ2022

    • Inventor(s)
      尾坂 格、三木江 翼、森山 太一、有海 裕作
    • Industrial Property Rights Holder
      尾坂 格、三木江 翼、森山 太一、有海 裕作
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2022-034404
    • Filing Date
      2022
    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 高分子化合物、高分子化合物の製造方法、有機薄膜太陽電池材料及び有機薄膜太陽電池2021

    • Inventor(s)
      尾坂 格、三木江 翼、森山 太一、有海 裕作
    • Industrial Property Rights Holder
      尾坂 格、三木江 翼、森山 太一、有海 裕作
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2021-132762
    • Filing Date
      2021
    • Related Report
      2021 Annual Research Report

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Published: 2020-09-29   Modified: 2023-01-30  

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