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The development of high-performance n-type organic semiconductors with herringbone molecular assembly

Research Project

Project/Area Number 20J12608
Research Category

Grant-in-Aid for JSPS Fellows

Allocation TypeSingle-year Grants
Section国内
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionThe University of Tokyo

Principal Investigator

YU CRAIG PEIQI  東京大学, 新領域創成科学研究科, 特別研究員(DC2)

Project Period (FY) 2020-04-24 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 2021: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2020: ¥1,100,000 (Direct Cost: ¥1,100,000)
Keywordsorganic semiconductors / molecular design / π-electron systems / field-effect transistors / n-type
Outline of Research at the Start

Organic semiconductors (OSCs) are promising materials for low-cost, and flexible electronics. To construct logic-circuits for high-end electronics, both p- and n-type OSCs are required. To develop high-performance n-type OSCs, the applicant proposes the following molecular features: 1) achieve two-dimensional molecular assemblies in the crystal structures; 2) fine
-tuning of intermolecular orbital overlaps and suppression of molecular motions; 3) achieve balanced effective masses; 4) obtain air-stable n-type semiconductor performances higher than 10 cm2 V/s.

Outline of Annual Research Achievements

In this fiscal year, my research focused on the molecular designs for effective solid-state packing structures with strong and balanced intermolecular orbital overlaps and resilience towards dynamic disorders in high-performance n-type organic semiconductors. The electron-deficient benzo[de]isoquinolino[1,8-gh]quinolinetetracarboxylic diimide (BQQDI) π-electron system is continuously used as the molecular design template and various substituents are incorporated to fine-tune the molecular assembly. With the use of bulky substituents on the BQQDI π-electron system, we achieved a two-dimensional isotropic packing motif and an isotropic charge transport for electron carriers. We demonstrated for the first time that the isotropic electron-carrier transport provides resilience to dynamic disorders and it is extremely beneficial for achieving high electron-carrier mobilities. We experimentally confirmed the isotropic charge transport and obtained an excellent air-stable electron mobility up to 3.0 cm2/Vs using four-probe field-effect transistors. In addition to this study, we also developed a synthetically and functionally versatile electron-deficient benzo[de]isoquinolino[1,8-gh]quinoline Diamide π-electron system that can access a wide range of orbital energies for various organic electronic applications including organic field-effect transistors and organic photovoltaics.

Research Progress Status

令和3年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

令和3年度が最終年度であるため、記入しない。

Report

(2 results)
  • 2021 Annual Research Report
  • 2020 Annual Research Report
  • Research Products

    (12 results)

All 2022 2021 2020

All Journal Article (7 results) (of which Int'l Joint Research: 7 results,  Peer Reviewed: 7 results,  Open Access: 4 results) Presentation (5 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] “Nitrogen-Containing Perylene Diimides: Molecular Design, Robust Aggregated Structures, and Advances in n-Type Organic Semiconductors”2022

    • Author(s)
      Shohei Kumagai, Hiroyuki Ishii, Go Watanabe, Craig P. Yu, Shun Watanabe, Jun Takeya, and Toshihiro Okamoto
    • Journal Title

      Acc. Chem. Res.

      Volume: 55 Issue: 5 Pages: 660-672

    • DOI

      10.1021/acs.accounts.1c00548

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Mixed-Orbital Charge Transport in N-Shaped Benzene- and Pyrazine-Fused Organic Semiconductors2022

    • Author(s)
      Yu Craig P., Kumagai Shohei, Kushida Tomokatsu, Mitani Masato, Mitsui Chikahiko, Ishii Hiroyuki, Takeya Jun, Okamoto Toshihiro
    • Journal Title

      Journal of American Chemical Society

      Volume: Accepted Issue: 25 Pages: 11159-11167

    • DOI

      10.1021/jacs.2c01357

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Approaching isotropic charge transport of n-type organic semiconductors with bulky substituents2021

    • Author(s)
      Yu Craig P.、Kojima Naoya、Kumagai Shohei、Kurosawa Tadanori、Ishii Hiroyuki、Watanabe Go、Takeya Jun、Okamoto Toshihiro
    • Journal Title

      Communications Chemistry

      Volume: 4 Issue: 1 Pages: 1-10

    • DOI

      10.1038/s42004-021-00583-2

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Role of Perfluorophenyl Group in the Side Chain of Small-Molecule n-Type Organic Semiconductors in Stress Stability of Single-Crystal Transistors2021

    • Author(s)
      Kumagai, S.; Yu, C. P.; Nakano, S.; Annaka, T.; Mitani, M.; Yano, M.; Ishii, H.; Takeya, J.; Okamoto, T.
    • Journal Title

      The Journal of Physical Chemistry Letters

      Volume: 12 Issue: 8 Pages: 2095-2101

    • DOI

      10.1021/acs.jpclett.0c03012

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Effect of Electronically Distinct Aromatic Substituents on the Molecular Assembly and Hole Transport of V-Shaped Organic Semiconductors2020

    • Author(s)
      Yu Craig P.、Mitani Masato、Ishii Hiroyuki、Yamagishi Masakazu、Kitamura Hiroki、Yano Masafumi、Takeya Jun、Okamoto Toshihiro
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 124 Issue: 32 Pages: 17503-17511

    • DOI

      10.1021/acs.jpcc.0c04088

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Bent-Shaped p-Type Small Molecule Organic Semiconductors: A Molecular Design Strategy for Next-Generation Practical Applications2020

    • Author(s)
      T. Okamoto, C. Yu, C. Mitsui, M. Yamagishi, H. Ishii, J. Takeya
    • Journal Title

      Journal of the American Chemical Society

      Volume: - Issue: 20 Pages: 9083-9096

    • DOI

      10.1021/jacs.9b10450

    • NAID

      120007168343

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Alkyl-Substituted Selenium-Bridged V-Shaped Organic Semiconductors Exhibiting High Hole Mobility and Unusual Aggregation Behavior2020

    • Author(s)
      Okamoto Toshihiro、Mitani Masato、Yu Craig P.、Mitsui Chikahiko、Yamagishi Masakazu、Ishii Hiroyuki、Watanabe Go、Kumagai Shohei、Hashizume Daisuke、Tanaka Shota、Yano Masafumi、Kushida Tomokatsu、Sato Hiroyasu、Sugimoto Kunihisa、Kato Takashi、Takeya Jun
    • Journal Title

      Journal of the American Chemical Society

      Volume: 142 Issue: 35 Pages: 14974-14984

    • DOI

      10.1021/jacs.0c05522

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Design and Synthesis of Benzo[de]isoquinolino[1,8-gh]quinolineDiamides π-Electron Systems2022

    • Author(s)
      Craig P. Yu, Akito Yamamoto, Shohei Kumagai, Hiroyuki Ishii, Jun Takeya, Toshihiro Okamoto
    • Organizer
      102nd CSJ Chemistry Annual Meeting
    • Related Report
      2021 Annual Research Report
  • [Presentation] Multi-Band Charge Transport in Bent-Shaped p-Type Organic Semiconductors2022

    • Author(s)
      Yu Craig P., Kumagai Shohei, Kushida Tomokatsu, Mitani Masato, Mitsui Chikahiko, Ishii Hiroyuki, Takeya Jun, Okamoto Toshihiro
    • Organizer
      69th The Japan Society of Applied Physics Spring Meeting
    • Related Report
      2021 Annual Research Report
  • [Presentation] Two-Dimensional Isotropic Charge Transport in n-Type Organic Semiconductors with Sterically Demanding Substituents2021

    • Author(s)
      Yu Craig P.、Kojima Naoya、Kumagai Shohei、Kurosawa Tadanori、Ishii Hiroyuki、Watanabe Go、Takeya Jun、Okamoto Toshihiro
    • Organizer
      Materials Research Meeting
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of Benzo[de]isoquinolino[1,8-gh]quinoline Diimide n-Type Organic Semiconductors with Asymmetric Substituents2021

    • Author(s)
      Craig P. Yu, Shohei Kumagai, Hiroyuki Ishii, Go Watanabe, Hiroki Sugiura, Yukio Tani, Tetsuya Watanabe, Jun Takeya, Toshihiro Okamoto
    • Organizer
      101st CSJ Chemistry Annual Meeting
    • Related Report
      2021 Annual Research Report
  • [Presentation] Development of Benzo[de]isoquinolino[1,8-gh]quinoline Diimide n-Type Organic Semiconductors with Asymmetric Substituents2021

    • Author(s)
      Craig P. Yu, Shohei Kumagai, Hiroyuki Ishii, Go Watanabe, Hiroki Sugiura4, Yukio Tani, Tetsuya Watanabe, Jun Takeya, and Toshihiro Okamoto
    • Organizer
      The 101st CSJ Annual Meeting
    • Related Report
      2020 Annual Research Report

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Published: 2020-07-07   Modified: 2024-03-26  

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