• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Development of high-performance n-type semiconducting polymers by precise control of molecular orbitals

Research Project

Project/Area Number 22K14745
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionHiroshima University

Principal Investigator

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

Project Period (FY) 2022-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2023: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2022: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywords半導体ポリマー / π共役系材料 / 有機薄膜太陽電池 / 有機トランジスタ / n型半導体 / π共役系化合物 / 電子輸送材料 / 有機電界効果トランジスタ / n型半導体ポリマー / 電子輸送性材料 / イミド化合物 / 有機エレクトロニクス
Outline of Research at the Start

高性能なn型半導体ポリマーの開発は、有機エレクトロニクスの発展に直結する重要課題の1つである。n型半導体ポリマーの高性能化には、ポリマー中に発生した電子を、①安定に輸送できる低い最低空軌道(LUMO)準位と、②効率的に輸送できる経路構築の両立が鍵である。本研究では、ポリマー主鎖内のLUMOの非局在化に着目し、主鎖内・主鎖間の両方を効率的な電子輸送経路として活用する高性能n型半導体ポリマーを開発する。

Outline of Final Research Achievements

In this study, we developed an n-type semiconductor polymers based on moderate electron-deficient building unit quinoxaline imide (QI) to delocalize LUMO along the polymer backbone. We found that whereas QI-based monomer itself showed insufficiently low LUMO energy levels, QI-based polymer showed sufficiently low LUMO that function as n-type materials. This results clearly indicated that delocalization of LUMO along the backbone is effective to lower the LUMO energy levels of the polymer. Furthermore, organic transistors based on QI-based polymer exhibited ambipolar behavior with high electron mobility more than 1 cm2/Vs.

Academic Significance and Societal Importance of the Research Achievements

塗って作製できる有機トランジスタや薄膜太陽電池は、次世代のデバイスとして注目されている。これらの開発にはp型及びn型半導体ポリマーの両方が必要であるが、p型に比べてn型ポリマーの開発が遅れている。従来、強力な電子欠損性を持つ骨格をポリマー主鎖に導入してLUMO準位を低下させることがn型半導体ポリマーの分子設計指針であった。一方、本研究では、LUMOの非局在化に着目した新しい分子設計により、「適度な」電子欠損性を持つ骨格を用いて十分に低いLUMO準位を有するポリマーの開発に成功した。新しい分子設計指針を示した本研究は、n型半導体ポリマーの高性能化へ向けて重要な知見となる。

Report

(3 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • Research Products

    (34 results)

All 2024 2023 2022 Other

All Int'l Joint Research (1 results) Journal Article (10 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 10 results,  Open Access: 4 results) Presentation (21 results) (of which Int'l Joint Research: 6 results,  Invited: 2 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] Purdue University(米国)

    • Related Report
      2023 Annual Research Report
  • [Journal Article] Manipulating the functionality and structures of π-conjugated polymers utilizing intramolecular noncovalent interactions towards efficient organic photovoltaics2024

    • Author(s)
      Kamimura Satoshi、Saito Masahiko、Teshima Yoshikazu、Yamanaka Kodai、Ichikawa Hiroyuki、Sugie Ai、Yoshida Hiroyuki、Jeon Jihun、Kim Hyung Do、Ohkita Hideo、Mikie Tsubasa、Osaka Itaru
    • Journal Title

      Chemical Science

      Volume: 15 Issue: 17 Pages: 6349-6362

    • DOI

      10.1039/d4sc00899e

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two Isomeric Benzo[d]imidazole-Based Nonfullerene Acceptors for Organic Photovoltaics2024

    • Author(s)
      Ono Shohei、Mikie Tsubasa、Nakano Kyohei、Tajima Keisuke、Osaka Itaru
    • Journal Title

      ACS Applied Energy Materials

      Volume: 7 Issue: 7 Pages: 2946-2954

    • DOI

      10.1021/acsaem.4c00212

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A highly crystalline face-on π-conjugated polymer based on alkoxythiophene-flanked benzobisthiazole for organic photovoltaics2024

    • Author(s)
      Doi Shuhei、Mikie Tsubasa、Yamanaka Kodai、Sato Yuki、Ohkita Hideo、Saito Masahiko、Osaka Itaru
    • Journal Title

      Polymer Journal

      Volume: - Issue: 11 Pages: 1051-1059

    • DOI

      10.1038/s41428-024-00906-9

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Bending the Rule: Naphthobisthiadiazole-Based Terpolymers with Both High Solubility and Crystallinity for Organic Photovoltaics2024

    • Author(s)
      Chou Li-Hui、Chen Fengkun、Nakano Kyohei、Yamanaka Kodai、Mikie Tsubasa、Saito Masahiko、Liu Cheng-Liang、Tajima Keisuke、Osaka Itaru
    • Journal Title

      ACS Applied Polymer Materials

      Volume: 6 Issue: 5 Pages: 2586-2593

    • DOI

      10.1021/acsapm.3c02772

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Simple π-Conjugated Polymers Based on Bithiazole for Nonfullerene Organic Photovoltaics2024

    • Author(s)
      Teshima Yoshikazu、Yamanaka Kodai、Sato Yuki、Ohkita Hideo、Mikie Tsubasa、Saito Masahiko、Osaka Itaru
    • Journal Title

      ACS Applied Materials Interfaces

      Volume: 16 Issue: 3 Pages: 3735-3743

    • DOI

      10.1021/acsami.3c14494

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ordered π-conjugated polymer backbone in amorphous blend for high efficiency nonfullerene organic photovoltaics2023

    • Author(s)
      Masahiko Saito, Hiroya Yamada, Kakaraparthi Kranthiraja, Jihun Jeon, Hyung Do Kim, Tsubasa Mikie, Akinori Saeki, Hideo Ohkita, Itaru Osaka
    • Journal Title

      Communications Materials

      Volume: 4 Issue: 1 Pages: 1-10

    • DOI

      10.1038/s43246-023-00395-y

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Naphthobispyrazine bisimide-based semiconducting polymers as electron acceptors for all-polymer photovoltaic cells2023

    • Author(s)
      Okamoto Kenta、Iwasaki Yuka、Mikie Tsubasa、Osaka Itaru
    • Journal Title

      Polymer Journal

      Volume: 55 Issue: 4 Pages: 443-450

    • DOI

      10.1038/s41428-022-00749-2

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Exciton dynamics of a fused ring π-conjugated nonfullerene molecule based on dithienonaphthobisthiadiazole2023

    • Author(s)
      Sato Yuki、Mikie Tsubasa、Yamada Hiroya、Osaka Itaru、Ohkita Hideo
    • Journal Title

      Japanese Journal of Applied Physics

      Volume: 62 Issue: SK Pages: SK1012-SK1012

    • DOI

      10.35848/1347-4065/acc66b

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Ester-functionalized quinoxaline-based polymers for application in organic photovoltaics2022

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

      Materials Chemistry and Physics

      Volume: 287 Pages: 126225-126225

    • DOI

      10.1016/j.matchemphys.2022.126225

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Halogen‐Free π‐Conjugated Polymers Based on Thienobenzobisthiazole for Efficient Nonfullerene Organic Solar Cells: Rational Design for Achieving High Backbone Order and High Solubility2022

    • Author(s)
      Nakao Naoya、Saito Masahiko、Mikie Tsubasa、Ishikawa Takumi、Jeon Jihun、Kim Hyung Do、Ohkita Hideo、Saeki Akinori、Osaka Itaru
    • Journal Title

      Advanced Science

      Volume: 10 Issue: 5 Pages: 2205682-2205682

    • DOI

      10.1002/advs.202205682

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] ビチアゾールジオンを基調としたπ 共役系ポリマーの合成とn 型半導体特性2023

    • Author(s)
      土井 脩平、三木江 翼、尾坂 格
    • Organizer
      第5回フロンティア太陽電池セミナー
    • Related Report
      2023 Annual Research Report
  • [Presentation] π共役系ポリマーの電荷輸送性を高める新しい分子設計と有機光触媒への応用2023

    • Author(s)
      三木江 翼
    • Organizer
      第7回次世代の有機化学・広島シンポジウム
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] 縮環チエノキノイド骨格を有するπ共役系ポリマーの電荷輸送特2023

    • Author(s)
      三木江 翼、岩﨑 優佳、土井 修平、石井 宏幸、尾坂 格
    • Organizer
      第84回応用物理学会秋季講演会
    • Related Report
      2023 Annual Research Report
  • [Presentation] Synthesis and charge transport property of a small bandgap polymer based on quinoidal bithiazole2023

    • Author(s)
      Shuhei Doi, Tsubasa Mikie, Itaru Osaka
    • Organizer
      The 13th SPSJ International Polymer Conference (IPC 2023)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of π-Conjugated Polymers Based on Dithienonaphthobisthiadiazole for Organic Transistors and Photovoltaics2023

    • Author(s)
      Kazuya Matsui, Tusbasa Mikie, Takuji Seo, Yutaka Ie, Itaru Osaka
    • Organizer
      The 13th SPSJ International Polymer Conference (IPC 2023)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] S-Pechmann-based polymer that realized high interchain charge carrier transport via extended π-electron delocalization2023

    • Author(s)
      Tsubasa Mikie, Keitaro Iguchi, Ryosuke Kamimura, Itaru Osaka
    • Organizer
      15th International Symposium on Functional π-Electron Systems (Fπ15)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] S-ペックマン系ポリマーにおける共役拡張による電荷移動度向上2023

    • Author(s)
      三木江 翼 ・井口 景太郎 ・上村 亮介・尾坂 格
    • Organizer
      第72回高分子年次大会
    • Related Report
      2023 Annual Research Report
  • [Presentation] ビチアゾールジオンを基調としたπ共役系ポリマーの合成と有機トランジスタへの応用2023

    • Author(s)
      土井 脩平 ・ 三木江翼 ・尾坂 格
    • Organizer
      第72回高分子年次大会
    • Related Report
      2023 Annual Research Report
  • [Presentation] ジチエノナフトビスチアジアゾールを有するπ共役系ポリマーの合成と物性2023

    • Author(s)
      松井 和哉・三木江 翼・瀬尾 卓司・家 裕隆・尾坂 格
    • Organizer
      第72回高分子年次大会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 低電圧損失と高電荷生成効率を両立する半導体ポリマーの開発と非フラーレン太陽電池の高効率化2022

    • Author(s)
      三木江 翼・駿河 翔太・森奥 友和・佐藤 友揮・石川 巧・キム ヒョンド・大北 英生・尾坂 格
    • Organizer
      第19回 「次世代の太陽光発電システム」シンポジウム
    • Related Report
      2022 Research-status Report
  • [Presentation] 結晶性半導体ポリマーを用いたナノ粒子光触媒の開発2022

    • Author(s)
      三木江 翼・藤田 知勇・尾坂 格
    • Organizer
      第71回 高分子討論会
    • Related Report
      2022 Research-status Report
  • [Presentation] キノイド型拡張縮環骨格を有する狭バンドギャップ半導体ポリマーの合成と電荷輸送特性2022

    • Author(s)
      岩﨑 優佳 ・三木江 翼・尾坂 格
    • Organizer
      第71回 高分子討論会
    • Related Report
      2022 Research-status Report
  • [Presentation] 有機薄膜太陽電池において低電圧損失と高電荷生成効率を両立する高性能半導体ポリマーの開発2022

    • Author(s)
      駿河 翔太・三木江 翼・石川 巧・佐藤 友揮・キム ヒョンド・大北 英生・尾坂 格
    • Organizer
      第71回 高分子討論会
    • Related Report
      2022 Research-status Report
  • [Presentation] ベンズイミダゾール部位を有する新規非フラーレンアクセプターの開発2022

    • Author(s)
      大野 翔平・三木江 翼・尾坂 格
    • Organizer
      第83回 応用物理学会秋季学術講演会
    • Related Report
      2022 Research-status Report
  • [Presentation] キノイド型拡張縮環骨格を有する狭バンドギャップ半導体ポリマーの合成と電荷輸送性2022

    • Author(s)
      岩﨑 優佳・三木江 翼・尾坂 格
    • Organizer
      第12回 CSJ化学フェスタ
    • Related Report
      2022 Research-status Report
  • [Presentation] ベンズイミダゾール部位を有する新規非フラーレンアクセプターの開発2022

    • Author(s)
      大野 翔平・三木江 翼・尾坂 格
    • Organizer
      第12回 CSJ化学フェスタ
    • Related Report
      2022 Research-status Report
  • [Presentation] A novel π-conjugated polymer enabling small voltage loss and high charge carrier generation in nonfullerene-based organic photovoltaics2022

    • Author(s)
      Tsubasa Mikie, Shota Suruga, Yuuki Sato, Takumi Ishikawa, Hyung Do Kim, Hideo Ohkita, Itaru Osaka
    • Organizer
      33rd International Photovoltaic Science and Engineering Conference
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of π-Conjugated Polymers Based on Dithienonaphthobisthiadiazole for High-Efficiency Organic Photovoltaics2022

    • Author(s)
      Tsubasa Mikie
    • Organizer
      The International Congress on Pure & Applied Chemistry Kota Kinabalu
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] キノキサリンイミドを有するπ共役系ポリマーの合成と電荷輸送特性2022

    • Author(s)
      上村 亮介・三木江 翼・尾坂 格
    • Organizer
      日本化学会第103回春季年会
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] ジチエノナフトビスチアジアゾールを有するπ共役系ポリマーの合成と有機トランジスタ特性2022

    • Author(s)
      松井 和哉・三木江 翼・瀬尾 卓司・家 裕隆・尾坂 格
    • Organizer
      日本化学会第103回春季年会
    • Related Report
      2022 Research-status Report
  • [Presentation] テトラチエノアセンジオン骨格を有するπ共役系ポリマーの合成と物性2022

    • Author(s)
      岩﨑 優佳・三木江 翼・尾坂 格
    • Organizer
      日本化学会第103回春季年会
    • Related Report
      2022 Research-status Report
  • [Remarks] 尾坂研究室website

    • URL

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

    • Related Report
      2023 Annual Research Report
  • [Patent(Industrial Property Rights)] 共役系重合体、電子供与性有機材料、光起電力素子用材料および光起電力素子2024

    • Inventor(s)
      尾坂 格、三木江 翼、土井 脩平
    • Industrial Property Rights Holder
      尾坂 格、三木江 翼、土井 脩平
    • Industrial Property Rights Type
      特許
    • Filing Date
      2024
    • Related Report
      2023 Annual Research Report

URL: 

Published: 2022-04-19   Modified: 2025-01-30  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi