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2011 Fiscal Year Final Research Report

Development of multifunctional materials based on fused heterocyclic compounds aiming at innovation of organic electronic devices

Research Project

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Project/Area Number 20685005
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

TSUJI Hayato  東京大学, 大学院・理学系研究科, 准教授 (20346050)

Project Period (FY) 2008 – 2011
Keywords元素科学 / 複素環 / 有機合成 / 機能性材料 / 有機半導体 / 有機EL
Research Abstract

Novelπ-conjugated hetero-and carbocyclic compounds have been developed based on new synthetic methodology of "modular synthesis", aiming at improvement in efficiency of organic electronic devices as well as proof of principle of innovative concepts of devices. Noteworthy is that the versatility of fused furans has been found out to serve as stable and high-performance semiconducting materials. For example, an ambipolar benzodifuran allowed us to fabricate efficient homojunction OLED that emit light across the full visible color range and perform at a level close to the theoretical limit. A naphtodiduran showed even higher mobility than amorphous silicon. Novel stable n-type materials, such as benzophospholes and bis(cinnoline) s have been also developed, and their versatility has been demonstrated by applying them to cathode buffer materials in thin-film solar cells. Multifunctional materials, such as highly emissive ambipolar material, near infrared-light absorbing/emitting materials, have been successfully obtained as well.

  • Research Products

    (35 results)

All 2012 2011 2010 2009 2008 Other

All Journal Article (9 results) Presentation (10 results) Book (1 results) Remarks (11 results) Patent(Industrial Property Rights) (4 results)

  • [Journal Article] Naphtho[ 2, 1-b : 6, 5-b'] difuran : a Versatile Motif Available for Solution-processed Single-crystal Organic Field-effect Transistors with High Hole Mobility2012

    • Author(s)
      Mitsui, C.; Soeda, J.; Miwa, K.; Tsuji, H.; Takeya, J.; Nakamura, E
    • Journal Title

      J. Am. Chem. Soc

      Volume: 134 Pages: 5448-5451

    • DOI

      DOI:10.1021/ja2120635

  • [Journal Article] Air-and Heat-stable Planar Tri-p-quinodimethane with Distinct Biradical Characteristics2011

    • Author(s)
      Zhu, X.; Tsuji, H.; Nakabayashi, K.; Ohkoshi, S.-i.; Nakamura, E
    • Journal Title

      J. Am. Chem. Soc

      Volume: 133 Pages: 16342-16345

    • DOI

      DOI:10.1021/ja206060n

  • [Journal Article] Bis-cinnolines as n-Type Semiconducting Material with High Electron-mobility and Thermal Stability and their Application to Organic Photovoltaic Cells2011

    • Author(s)
      Tsuji, H.; Yokoi, Y.; Sato, Y.; Tanaka, H.; Nakamura, E
    • Journal Title

      Chem. Asian J

      Volume: 6 Pages: 2005-2008

    • DOI

      DOI:10.1002/asia.201100326

  • [Journal Article] Synthesis of Tetra substituted Alkenes by Stereo-and Regioselective Stannyl lithiation of Diaryl acetylenes2010

    • Author(s)
      Tsuji, H.; Ueda, Y.; Ilies, L.; Nakamura E
    • Journal Title

      J. Am. Chem. Soc

      Volume: 132 Pages: 11854-11855

    • DOI

      DOI:10.1021/ja1059119

  • [Journal Article] Modular Synthesis of 1H-Indenes, Dihydro-s-Indacene, and Diindenoindacene-A Carbon-bridged p-Phenylene vinylene Congener2009

    • Author(s)
      Zhu, X.; Mitsui, C.; Tsuji, H.; Nakamura, E
    • Journal Title

      J. Am. Chem. Soc

      Volume: 131 Pages: 13596-13597

    • DOI

      DOI:10.1021/ja905626b

  • [Journal Article] Benzo[ b] phosphole Sulfides. Highly Electron-transporting and Thermally Stable Molecular Materials for Organic Semiconductor Devices2009

    • Author(s)
      Tsuji, H.; Sato, K.; Sato, Y.; Nakamura, E
    • Journal Title

      J. Mater. Chem

      Volume: 19 Pages: 3364-3366

    • DOI

      DOI:10.1039/B906197E

  • [Journal Article] Bis(carbazolyl) benzodifuran : AHigh-mobility Ambipolar Material for Homojunction Organic Light-emitting Diode Devices2009

    • Author(s)
      Tsuji, H.; Mitsui, C.; Sato, Y.; Nakamura, E.
    • Journal Title

      Adv. Mater

      Volume: 21 Pages: 3776-3379

    • DOI

      DOI:10.1002/adma.200900634

  • [Journal Article] Manganese-Catalyzed Benzene Synthesis by[ 2+2+2] Couplingof 1, 3-Dicarbonyl Compound and Terminal Acetylene2008

    • Author(s)
      Tsuji, H.; Yamagata, K.-i.; Fujimoto, T.; Nakamura, E.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 130 Pages: 7792-7793

    • DOI

      DOI:10.1021/ja8015186

  • [Journal Article] Modular Synthesis of Functionalized Benzosiloles by Tin-Mediated Cyclization of(o-Alkynylphenyl) silane2008

    • Author(s)
      Ilies, L.; Tsuji, H.; Sato, Y.; Nakamura, E.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 130 Pages: 4240-4241

    • DOI

      DOI:10.1021/ja800636g

  • [Presentation] 新反応が拓く新規有機デバイス材料2012

    • Author(s)
      辻勇人
    • Organizer
      日本化学会第92春年会
    • Place of Presentation
      慶應義塾大学,横浜
    • Year and Date
      2012-03-28
  • [Presentation] Carbon-Bridged Oligo(phenylenevinyl-ene) s : Rigid planar i-Conjugated Systemwith High Photo-and Electrochemical Stability2011

    • Author(s)
      Tsuji, H.; Zhu, X.; Nakamura, E.
    • Organizer
      10th International Symposium onOrganic Reactions(ISOR10)
    • Place of Presentation
      Keio University, Yokohama
    • Year and Date
      20111121-24
  • [Presentation] π電子共役系機能性物質のモジュラー合成と有機デバイスへの応用2011

    • Author(s)
      辻勇人
    • Organizer
      第46回有機反応若手の会
    • Place of Presentation
      水上
    • Year and Date
      20110707-09
  • [Presentation] Synthesis ofπ-Conjugated System Containing Group 15 Elements and Their Application to OrganicSemiconducting Devices2010

    • Author(s)
      Tsuji, H.; Nakamura, E.
    • Organizer
      The 5thInternational Conference on Cutting-EdgeOrganic Chemistry in Asia(ICCEOCA-5)
    • Place of Presentation
      Hsinchu, Taiwan.
    • Year and Date
      20101107-11
  • [Presentation] π共役系の機能モジュレーション2010

    • Author(s)
      辻勇人
    • Organizer
      第59回高分子討論会
    • Place of Presentation
      北海道大学,札幌
    • Year and Date
      20100915-17
  • [Presentation] 電子共役系機能性物質のモジュラー合成2010

    • Author(s)
      辻勇人
    • Organizer
      第27回有機合成化学セミナー
    • Place of Presentation
      舞子,神戸
    • Year and Date
      20100902-04
  • [Presentation] Property Modulation of BenzodifuranDerivatives via Zn-Mediated Cyclization2010

    • Author(s)
      Tsuji, H.; Mitsui, C.; Sato, Y.; Nakamura, E.
    • Organizer
      24th International Conference onOrganometallic Chemistry(ICOMC)
    • Place of Presentation
      Taipei, Taiwan.
    • Year and Date
      20100718-23
  • [Presentation] Synthesis of Benzophosphole Derivativesand Their Utility as n-Type Material forOrganic Semiconducting Devices2010

    • Author(s)
      Tsuji, H.; Sato, K.; Sato, Y.; Nakamura, E.
    • Organizer
      Pacifi-chem
    • Place of Presentation
      Honolulu, HI, USA.
    • Year and Date
      2010-12-17
  • [Presentation] Modular Synthesis of-Conjugated System Including Group 15Elements2009

    • Author(s)
      Tsuji, H.; Yokoi, Y.; Sato, K.; Sato, Y.; Nakamura, E.
    • Organizer
      Modular Synthesis of-Conjugated System Including Group 15Elements
    • Place of Presentation
      Luxembourg.
    • Year and Date
      20090719-24
  • [Presentation] Synthesis of Fused pi-ConjugatedMolecules and their Applications to OrganicElectronic Devices2009

    • Author(s)
      Tsuji, H.
    • Organizer
      5th Sino-JapaneseSymposium on Organic Chemistry forYoung Scientists
    • Place of Presentation
      Chengdu, China.
    • Year and Date
      2009-10-08
  • [Book] 「有機EL照明用材料の開発と評価技術」サイエンス & テクノロジー2010

    • Author(s)
      辻勇人
    • Total Pages
      44-52
  • [Remarks] 研究成果に関するサイトのURL東京大学プレスリリース「見えてきた照明・ディスプレイの未来形」

    • URL

      http://www.s.u-tokyo.ac.jp/press/press-2009-12.html

  • [Remarks] 受賞Banyu Chemistry Award2009「炭素環およびヘテロ環形成反応の開発と応用」2009. 12. 5

  • [Remarks] 受賞有機合成化学奨励賞「電子共役系機能性物質のモジュラー合成」2010. 2. 19

  • [Remarks] 受賞平成22年度文部科学大臣表彰若手科学者賞「有機電子素子の革新に資する含典型元素有機材料開発の研究」2010. 4. 13

  • [Remarks] 受賞Thieme Chemistry Journal Award2011, 2010. 11. 29

  • [Remarks] 研究成果に関する新聞報道日本経済新聞(2009. 5. 25,夕刊1面)

  • [Remarks] 研究成果に関する新聞報道毎日新聞(2009. 5. 25,夕刊6面)

  • [Remarks] 研究成果に関する新聞報道日経産業新聞(2009. 5. 26, 11面)

  • [Remarks] 研究成果に関する新聞報道読売新聞(2009. 7. 5,朝刊23面)

  • [Remarks] 研究成果に関する新聞報道神戸新聞(2009. 7. 25,朝刊5面)

  • [Remarks] 解説記事等辻勇人・中村栄一,「【化学レビュー】第32回物理有機化学有機エレクトロニクスの最前線?分子を並べて機能を発現させる」,化学,化学同人, Vol.66, No.11, pp.54-58(2011).

  • [Patent(Industrial Property Rights)] ベンゾホスホール化合物を用いた有機光電変換素子2012

    • Inventor(s)
      中村栄一,佐藤佳晴,辻勇人,佐藤恒輔
    • Industrial Property Rights Holder
      JST
    • Industrial Property Number
      特許、第4964258号
    • Acquisition Date
      2012-04-06
  • [Patent(Industrial Property Rights)] 縮環ピロール化合物を用いた有機電界発光素子2012

    • Inventor(s)
      中村栄一,佐藤佳晴,辻勇人,横井優季
    • Industrial Property Rights Holder
      JST
    • Industrial Property Number
      特許、第4906810号
    • Acquisition Date
      2012-01-20
  • [Patent(Industrial Property Rights)] 芳香族アミン化合物を用いた有機電界発光素子2010

    • Inventor(s)
      中村栄一,佐藤佳晴,辻勇人,三津井親彦
    • Industrial Property Rights Holder
      JST
    • Industrial Property Number
      特許、第4583470
    • Acquisition Date
      2010-11-17
  • [Patent(Industrial Property Rights)] インダセン誘導体及びその製造方法,並びに炭素架橋p.フェニレンビニレン誘導体及びその製造方法2009

    • Inventor(s)
      中村栄一,辻勇人,朱曉張
    • Industrial Property Rights Holder
      東京大学
    • Industrial Property Number
      特許、特願2009-178975
    • Filing Date
      2009-07-31

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Published: 2013-07-31  

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