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有機エレクトロニクスデバイスの高性能化を可能にする2次元拡張型π電子系の開発

Research Project

Project/Area Number 17J10525
Research Category

Grant-in-Aid for JSPS Fellows

Allocation TypeSingle-year Grants
Section国内
Research Field Functional solid state chemistry
Research InstitutionKyoto University

Principal Investigator

中村 智也  京都大学, 工学研究科, 特別研究員(DC2)

Project Period (FY) 2017-04-26 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2018: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2017: ¥1,000,000 (Direct Cost: ¥1,000,000)
Keywords分子配向 / 非晶質性 / 有機半導体 / 有機エレクトロニクス / 水素結合 / ペロブスカイト太陽電池
Outline of Annual Research Achievements

有機エレクトロニクスデバイスの高性能化には,素子を構成する薄膜中で有機半導体分子をどのように並べるか,すなわち分子配向の制御が決定的に重要である.基板に垂直な方向の電荷輸送が必要となる有機太陽電池では,分子のπ軌道が基板に対して垂直方向に重なるface-on配向が望ましい.さらに,有機ELやペロブスカイト太陽電池の電荷輸送材料には膜の平滑性が求められる.そのためには材料の結晶性を低く保ったまま分子を配向させることが重要となるが,特に溶液法においては,非晶質性と配向制御の両立は困難であった.
そこで,私は分子間の水素結合の形成に着目し,トリアジンにフタルイミドを3つ導入したY字型分子を設計した.この分子では,フタルイミド部位の回転による複数の配座異性体の存在により結晶化が抑制されることに加え,分子間の水素結合によってface-on配向型の分子集合体を形成できると考えた.実際,Boc保護体を前駆体化合物として,その薄膜を水素置換体へと変換させる過程で,非晶質性を保ちながらその配向がface-onへと変化することがわかった.また,フタルイミドを2つ導入したV字型分子との比較から,2次元シート状の水素結合ネットワークの形成が分子をface-onに配向させる推進力となっていることを見出した.さらに,基板に対して垂直な方向の電子移動度を評価した結果,face-on配向を示したY字型分子は,face-on配向を示したV字型分子よりも1桁程度高い電子移動度を示すことが明らかになった.

Research Progress Status

平成30年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

平成30年度が最終年度であるため、記入しない。

Report

(2 results)
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (20 results)

All 2019 2018 2017

All Journal Article (7 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 6 results,  Open Access: 1 results) Presentation (11 results) (of which Int'l Joint Research: 8 results,  Invited: 1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Molecular Orientation Change in Naphthalene Diimide Thin Films Induced by Removal of Thermally Cleavable Substituents2019

    • Author(s)
      Nakamura Tomoya、Shioya Nobutaka、Shimoaka Takafumi、Nishikubo Ryosuke、Hasegawa Takeshi、Saeki Akinori、Murata Yasujiro、Murdey Richard、Wakamiya Atsushi
    • Journal Title

      Chemistry of Materials

      Volume: 31 Issue: 5 Pages: 1729-1737

    • DOI

      10.1021/acs.chemmater.8b05237

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure-property relations in Ag-Bi-I compounds: potential Pb-free absorbers in solar cells2019

    • Author(s)
      A. Koedtruad, M. Goto, M. Amano Patino, Z. Tan, H. Guo, T. Nakamura, T. Handa, W. -T. Chen, Y. -C. Chuang, H. -S. Sheu, T. Saito, D. Kan, Y. Kanemitsu, A. Wakamiya, and Y. Shimakawa
    • Journal Title

      J. Mater. Chem. A

      Volume: 7 Issue: 10 Pages: 5583-5588

    • DOI

      10.1039/c8ta11227d

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Influence of Alkoxy Chain Length on the Properties of Two‐Dimensionally Expanded Azulene‐Core‐Based Hole‐Transporting Materials for Efficient Perovskite Solar Cells2019

    • Author(s)
      Truong Minh Anh、Lee Jaehyun、Nakamura Tomoya、Seo Ji‐Youn、Jung Mina、Ozaki Masashi、Shimazaki Ai、Shioya Nobutaka、Hasegawa Takeshi、Murata Yasujiro、Zakeeruddin Shaik Mohammed、Gratzel Michael、Murdey Richard、Wakamiya Atsushi
    • Journal Title

      Chemistry - A European Journal

      Volume: 印刷中 Issue: 27 Pages: 6741-6752

    • DOI

      10.1002/chem.201806317

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Donor-acceptor polymers containing thiazole-fused benzothiadiazole acceptor units for organic solar cells2019

    • Author(s)
      Nakamura Tomoya、Ishikura Yasuhisa、Arakawa Noriko、Hori Megumi、Satou Motoi、Endo Masaru、Masui Hisashi、Fuse Shinichiro、Takahashi Takashi、Murata Yasujiro、Murdey Richard、Wakamiya Atsushi
    • Journal Title

      RSC Advances

      Volume: 9 Issue: 13 Pages: 7107-7114

    • DOI

      10.1039/c9ra00229d

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Doping Polycyclic Arenes with Nitrogen-Boron-Nitrogen (NBN) Units2018

    • Author(s)
      Yang Deng-Tao、Nakamura Tomoya、He Zhechang、Wang Xiang、Wakamiya Atsushi、Peng Tai、Wang Suning
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 21 Pages: 6741-6745

    • DOI

      10.1021/acs.orglett.8b02850

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] ペロブスカイト太陽電池のための有機半導体材料―電荷輸送材料の分子設計2018

    • Author(s)
      中村 智也,若宮 淳志
    • Journal Title

      化学

      Volume: 73 Pages: 66-67

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Synthesis of Azole-fused Benzothiadiazoles as Key Units for Functional π-Conjugated Compounds2017

    • Author(s)
      Tomoya Nakamura, Shuhei Okazaki, Noriko Arakawa, Motoi Satou, Masaru Endo, Yasujiro Murata, Atsushi Wakamiya*
    • Journal Title

      Journal of Photopolymer Science and Technology

      Volume: 30 Issue: 5 Pages: 561-568

    • DOI

      10.2494/photopolymer.30.561

    • NAID

      130005950293

    • ISSN
      0914-9244, 1349-6336
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] Molecular Orientation Control in Naphthalene Diimides2018

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Atsushi Wakamiya
    • Organizer
      The 15th International Symposium on Inorganic Ring Systems (IRIS-15)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Hydrogen Bond Networks for Controlling Molecular Orientation of Naphthalene Diimides2018

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Richard Murdey, Atsushi Wakamiya
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis (MACOS)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Control of Molecular Orientation in Naphthalene Diimides2018

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Atsushi Wakamiya
    • Organizer
      First International Conference on 4D Materials and Systems (ECS-4DMS)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Weakly Interacting Hydrogen Bond Networks for Controlling Molecular Orientation of Naphthalene Diimides2018

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Richard Murdey, Atsushi Wakamiya
    • Organizer
      28th International Symposium on the Organic Chemistry of Sulfur (ISOCS-28)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 水素結合ネットワークを利用した有機半導体薄膜の分子配向制御2018

    • Author(s)
      中村 智也,塩谷 暢貴,下赤 卓史,長谷川 健,村田 靖次郎,マーディー リチャード,若宮 淳志
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Hydrogen Bond Networks for Controlling Molecular Orientation of Organic Semiconductor Thin Films2018

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Richard Murdey, Atsushi Wakamiya
    • Organizer
      The 18th Japan-Korea Joint Symposium on Organometallic and Coordination Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 水素結合ネットワークを利用したn型有機半導体の分子配向制御2018

    • Author(s)
      中村 智也,塩谷 暢貴,下赤 卓史,長谷川 健,村田 靖次郎,マーディー リチャード,若宮 淳志
    • Organizer
      第3回pMAIRSワークショップ
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Azole-fused Benzothiadiazoles as Key Units for Functional π-Conjugated Compounds2017

    • Author(s)
      Tomoya Nakamura, Shuhei Okazaki, Noriko Arakawa, Motoi Satou, Masaru Endo, Yasuhisa Ishikura, Yasujiro Murata, Atsushi Wakamiya
    • Organizer
      The 34th International Conference of Photopolymer Science and Technology
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Naphthalene Diimide-based Electron-Transporting Layer for n-i-p Type Planer Perovskite Solar Cells2017

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Atsushi Wakamiya
    • Organizer
      17th International Symposium on Novel Aromatic Compounds
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Naphthalene Diimide-Based Electron-Transporting Layer for Planer Perovskite Solar Cells2017

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Atsushi Wakamiya
    • Organizer
      IRCCS-JST CREST Joint Symposium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Control of Molecular Orientation in Rylene Diimides2017

    • Author(s)
      Tomoya Nakamura, Nobutaka Shioya, Takafumi Shimoaka, Takeshi Hasegawa, Yasujiro Murata, Atsushi Wakamiya
    • Organizer
      日本化学会第98回年会
    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] 新規化合物2018

    • Inventor(s)
      若宮 淳志,中村 智也
    • Industrial Property Rights Holder
      若宮 淳志,中村 智也
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2018-165868
    • Filing Date
      2018
    • Related Report
      2018 Annual Research Report
  • [Patent(Industrial Property Rights)] 電子輸送層、及び電子輸送層の製造方法2017

    • Inventor(s)
      若宮淳志、中村智也
    • Industrial Property Rights Holder
      若宮淳志、中村智也
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2017-142184
    • Filing Date
      2017
    • Related Report
      2017 Annual Research Report

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Published: 2017-05-25   Modified: 2024-03-26  

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