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

2018 Fiscal Year Annual Research Report

Development of high-performance organic semiconductors by multi-hierarchy control

Research Project

Project/Area Number 15H02196
Research InstitutionTohoku University

Principal Investigator

瀧宮 和男  東北大学, 理学研究科, 教授 (40263735)

Project Period (FY) 2015-04-01 – 2019-03-31
Keywords有機半導体 / 有機導体 / 超分子 / 有機エレクトロニクス / 有機薄膜デバイス
Outline of Annual Research Achievements

前年度までの研究成果を受け、本年度は以下の検討を行った。
1.優れたn型半導体骨格であるNTIの合成上の問題点を克服するため、昨年度開発した二つのCH結合活性化反応(NDIの選択的モノハロゲン化、及びNTIチオフェンα位の直接アリール化)のうち、後者の直接アリールの適用範囲を明らかにし、多様なNTI誘導体の合成を行った。このうち、複数のNTIユニットを三次元的に配置した新規な誘導体の開発もにも成功し、NTIユニットの数と物性、配向性、結晶性の相関を得た。また、これら新規分子を用いることで、現状で5%程度の光電変換効率の太陽電池が得られている。
2.アセンジチオフェン系の結晶構造制御に関し、π拡張分子に関して結晶構造と移動度との相関を明らかにしただけでなく、分子構造を含セレン系にも拡張した。単結晶構造解析と単結晶トランジスタを用いる構造物性相関研究に加え、今年度、Hirshfeld表面解析とSymmetry Adapted Perturbation Theory計算を取り入れ、分子構造と結晶構造の相関を検討した。その結果、アセンジカルコゲノフェン系の結晶構造制御に関して分子間相互作用に関する定量的な知見を得た。この考えを他の分子骨格系にも拡張したところ、実際に結晶構造が系統的に変化することを見出した。
3.-4.3 eVもの高いHOMOを持ちながら比較的安定なn型ドープ材料を開発した。その安定性は、分子内に回転の自由度をもつことが関連することが示唆された。また、この新規ドーパントにより代表的なn型ポリマーであるN2200のドープを行い、物性評価も行うことが出来た。
このほか、種々のDNTT誘導体化のための鍵中間体の開発、光学活性分岐アルキル基導入のための試薬の開発、更には非平面有機半導体のための基本骨格の開発など、多くの多階層制御のための基本分子群を得ることに成功している。

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。

  • Research Products

    (30 results)

All 2019 2018

All Journal Article (5 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results,  Open Access: 3 results) Presentation (25 results) (of which Int'l Joint Research: 17 results,  Invited: 11 results)

  • [Journal Article] Two Isomeric Perylenothiophene Diimides: Physicochemical Properties and Applications in Organic Semiconducting Devices2019

    • Author(s)
      Nakano Masahiro, Nakano Kyohei, Takimiya Kazuo, Tajima Keisuke,
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 7 Pages: 2267-2275

    • DOI

      10.1039/c8tc05577g

    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of Thiophene‐annulated Naphthalene Diimide‐based Small‐Molecular Acceptors via Two‐step C-H Activation2019

    • Author(s)
      Maitisideike Rukeyamu, Takimiya Kazuo
    • Journal Title

      Chemistry an Asian Journal

      Volume: 0 Pages: 0

    • DOI

      10.1002/asia.201801655

    • Peer Reviewed / Open Access
  • [Journal Article] Thienoquinoidal System: Promising Molecular Architecture for Optoelectronic Applications2018

    • Author(s)
      Takimiya Kazuo, Kawabata Kohsuke
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 76 Pages: 1176–1184

    • DOI

      10.5059/yukigoseikyokaishi.76.1176

    • Peer Reviewed / Open Access
  • [Journal Article] Solution-crystallized n-type organic thin-film transistors: An impact of branched alkyl chain on high electron mobility and thermal durability2018

    • Author(s)
      Kumagai Shohei, Nakano Masahiro, Takimiya Kazuo, Takeya Junichi
    • Journal Title

      Organic Electronics

      Volume: 62 Pages: 548-553

    • DOI

      10.1016/j.orgel.2018.06.029

    • Peer Reviewed
  • [Journal Article] Air-stable and balanced split-gate organic transistors2018

    • Author(s)
      Yoo Hocheon, Nakano Masahiro, On Sungmin, Ahn Hyungju, Lee Han-Koo, Takimiya Kazuo
    • Journal Title

      Organic Electronics

      Volume: 63 Pages: 200-206

    • DOI

      10.1016/j.orgel.2018.09.022

    • Peer Reviewed / Int'l Joint Research
  • [Presentation] 高移動度有機半導体へのアプローチ:結晶構造制御の可能性2019

    • Author(s)
      瀧宮 和男
    • Organizer
      情報化学用有機材料第142委員会  A部会(インテリジェント有機材料)第140回、B部会(有機光エレクトロニクス) 第85回、合同研究会
    • Invited
  • [Presentation] 有機半導体分子の現在・過去・未来2019

    • Author(s)
      瀧宮 和男
    • Organizer
      日本化学会・第99春季年会(2019)
    • Invited
  • [Presentation] pブロック官能基を用いる有機半導体の結晶構造制御2019

    • Author(s)
      瀧宮 和男
    • Organizer
      日本化学会・第99春季年会(2019)
    • Invited
  • [Presentation] Near-infrared absorbing organic semiconductors based on naphthodithiophenedione2019

    • Author(s)
      川畑 公輔
    • Organizer
      日本化学会・第99春季年会(2019)
  • [Presentation] Control of packing structure of organic semiconductors by introduction of small substituents2019

    • Author(s)
      大垣 拓也
    • Organizer
      日本化学会・第99春季年会(2019)
  • [Presentation] Rational Packing Design to Approach Thienoacene-based Organic Semiconductors Rivaling Rubrene2019

    • Author(s)
      Wang Chengyuan
    • Organizer
      日本化学会・第99春季年会(2019)
  • [Presentation] Thiophene-fused naphthalene diimides: New building blocks for electron deficient π-functional materials2018

    • Author(s)
      瀧宮 和男
    • Organizer
      【116委員会】シンガポールー日本合同シンポジウム "Singapore‐Japan Bilateral Meeting"
    • Int'l Joint Research
  • [Presentation] Thiophene-fused naphthalene diimides: New building blocks for electron deficient π-functional materials2018

    • Author(s)
      瀧宮 和男
    • Organizer
      ICOE-2018:14th International conference on organic electronics
    • Int'l Joint Research / Invited
  • [Presentation] Thiophene-Fused Naphthalene Diimides: New Building Blocks for Electron Deficient π-Functional Materials2018

    • Author(s)
      瀧宮 和男
    • Organizer
      ICSM 2018:The International Conference on Science and Technology of Synthetic Metals 2018
    • Int'l Joint Research / Invited
  • [Presentation] Control of packing structure of thienoacene-based organic semiconductors2018

    • Author(s)
      瀧宮 和男
    • Organizer
      ILCC2018:27th International Liquid Crystal Conference
    • Int'l Joint Research / Invited
  • [Presentation] Thiophene-fused naphthalene diimides: New building blocks for electron deficient π-functional materials2018

    • Author(s)
      瀧宮 和男
    • Organizer
      ICCC2018:43rd International Conference on Coordination Chemistry
    • Int'l Joint Research / Invited
  • [Presentation] Control of packing structure of thienoacene-based organic semiconductors2018

    • Author(s)
      瀧宮 和男
    • Organizer
      ISOCS-28:28th International Symposium on the Organic Chemistry of Sulfur
    • Int'l Joint Research / Invited
  • [Presentation] Control of packing structure of thienoacene-based organic semiconductors: toward “artificial rubrene”2018

    • Author(s)
      瀧宮 和男
    • Organizer
      The 3rd International Symposium on Chemical Communication
    • Int'l Joint Research / Invited
  • [Presentation] 合成化学で創る電子機能 ~有機半導体の設計と合成~2018

    • Author(s)
      瀧宮 和男
    • Organizer
      電通大先端化学セミナー
    • Invited
  • [Presentation] Control of packing structure of thienoacene-based organic semiconductors: toward “artificial rubrene”2018

    • Author(s)
      瀧宮 和男
    • Organizer
      豊田理研国際ワークショップ"The 8th TOYOTA RIKEN International Workshop on Organic semiconductors, conductors, and electronics"
    • Int'l Joint Research / Invited
  • [Presentation] Alkylthionation of Thienoacenes to Tune Their Packing, Molecular Orientation and Semiconducting Properties2018

    • Author(s)
      Wang Chengyuan
    • Organizer
      2018 MRS Spring Meeting & Exhibit
    • Int'l Joint Research
  • [Presentation] Control of Major Carriers in an Ambipolar Polymer Semiconductor by Self-Assembled2018

    • Author(s)
      中野 正浩
    • Organizer
      ICOE-2018:14th International conference on organic electronics
    • Int'l Joint Research
  • [Presentation] Alkylthionation of Thienoacenes to Tune the Packing, Molecular Orientation and Semiconducting Properties2018

    • Author(s)
      Wang Chengyuan
    • Organizer
      ICOE-2018:14th International conference on organic electronics
    • Int'l Joint Research
  • [Presentation] Structural Effects on Dynamic Polymerization Behavior of Naphthodithiophene Diradicaloids2018

    • Author(s)
      鈴木 直弥
    • Organizer
      豊田理研国際ワークショップ"The 8th TOYOTA RIKEN International Workshop on Organic semiconductors, conductors, and electronics"
    • Int'l Joint Research
  • [Presentation] Acenedithiophenediones: a new class electron-defcient π-building blocks2018

    • Author(s)
      川畑 公輔
    • Organizer
      豊田理研国際ワークショップ"The 8th TOYOTA RIKEN International Workshop on Organic semiconductors, conductors, and electronics"
    • Int'l Joint Research
  • [Presentation] Pyrene derivatives modiNed with small substituents as potential organic semiconductors2018

    • Author(s)
      大垣 拓也
    • Organizer
      豊田理研国際ワークショップ"The 8th TOYOTA RIKEN International Workshop on Organic semiconductors, conductors, and electronics"
    • Int'l Joint Research
  • [Presentation] Acenedithiophenediones as new electron-withdrawing building units in Donor-Acceptor-Donor triads2018

    • Author(s)
      川畑 公輔
    • Organizer
      IFOC:International Forum on Chemistry of Functional Organic Chemicals
    • Int'l Joint Research
  • [Presentation] Structural Effects on Reversible Polymerization Behavior of Naphthodithiophene Diradicaloids2018

    • Author(s)
      鈴木 直弥
    • Organizer
      IFOC:International Forum on Chemistry of Functional Organic Chemicals
    • Int'l Joint Research
  • [Presentation] Pyrene derivatives modified with small substituents as potential organic semiconductors2018

    • Author(s)
      大垣 拓也
    • Organizer
      IFOC:International Forum on Chemistry of Functional Organic Chemicals
    • Int'l Joint Research
  • [Presentation] チオフェン縮環ぺリレンジイミドの開発と有機半導体材料への応用2018

    • Author(s)
      中野 正浩
    • Organizer
      第45回有機典型元素化学討論会

URL: 

Published: 2019-12-27  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi