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

Research of organic electronics using novel nitrogen heterocyclic compounds

Research Project

Project/Area Number 22550162
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials/Devices
Research InstitutionTokyo Institute of Technology

Principal Investigator

NISHIDA Junichi  東京工業大学, 大学院・総合理工学研究科, 助教 (70334521)

Co-Investigator(Renkei-kenkyūsha) YAMASHITA Yoshiro  東京工業大学, 大学院・総合理工学研究科, 教授 (90116872)
Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2012: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機半導体デバイス / 有機合成化学 / 有機化学 / 半導体物性 / 高効率太陽電池材料・素子 / 有機導体 / 有機半導体 / 複素環化合物 / 色素増感太陽電池 / 分子集合体
Research Abstract

In this work, novel nitrogen heterocyclic compounds were designed and synthesized for application to organic electronic devices. π-Conjugated compounds having nitrogen atoms have good electron-donating or accepting properties and afford unique physical properties and intramolecular interactions owing to polarized structures. Optical and electrochemical properties in solution and solid state were investigate. Organic electronic devices were prepared by using these compounds. Diazaboroles containing nitrogen and boron atoms work as p-type semiconductors in Field-Effect Transistors (FET). Diazaboroles fused with a quinone unit work as n-type semiconductors in FET devices. Dioxapyrrolopyrrole derivatives show good electron-transporting properties, when they form hydrogen-bonding networks. Diindenopyrazinedione derivatives with C=N double bonds have low LUMO energy level and give low threshold voltages of FET characteristics. N-Phenylimide derivatives with a trifluoromethylphenyl group at the phenyl group form noncentrosymmetric molecular arrangement and show triboluminescence (TL).

Report

(4 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (48 results)

All 2013 2012 2011 2010 Other

All Journal Article (22 results) (of which Peer Reviewed: 22 results) Presentation (23 results) Remarks (3 results)

  • [Journal Article] Synthesis and Photo-Electrochemical Properties of Novel Thienopyrazine and Quinoxaline Derivatives, and Their Dye-Sensitized Solar Cell Performance2012

    • Author(s)
      T. Kono, T. N. Murakami, J. Nishida, Y. Yoshida, K. Hara, Y. Yamashita
    • Journal Title

      Org.Electronics

      Volume: 13(12) Issue: 12 Pages: 3097-3101

    • DOI

      10.1016/j.orgel.2012.09.005

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Solution-processed and Air-stable n-Type Organic Thin-Film Transistors Based on Thiophenefused Dicyanoquinonediimine (DCNQI) Derivative2012

    • Author(s)
      S. Chen, Y. Zhao, A. Bolag, J. Nishida, Y. Liu, Y. Yamashita
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 4(8) Issue: 8 Pages: 3994-4000

    • DOI

      10.1021/am300822z

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Ambipolar Behavior of Hydrogen-Bonded Diketopyrrolopyrrole-thiophene Cooligomers Formed from Their Soluble Precursors2012

    • Author(s)
      Y. Suna, J. Nishida, Y. Fujisaki, Y. Yamashita
    • Journal Title

      Org. Lett.

      Volume: 14(13) Issue: 13 Pages: 3356-3359

    • DOI

      10.1021/ol3013364

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis Crystal Structure and Properties of 6,12-Diaryl Substituted Indeno[1,2-b]fluorenes2012

    • Author(s)
      J. Nishida, S. Tsukaguchi, Y. Yamashita
    • Journal Title

      Chem. Eur. J.

      Volume: 18(29) Issue: 29 Pages: 8964-8970

    • DOI

      10.1002/chem.201200591

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Tetracyanoanthraquinodimethanes Having Biaryl Substituents: Synthesis, Crystal Structures, and Physical Properties2012

    • Author(s)
      H. Chiba, J. Nishida, Y. Ya mashita
    • Journal Title

      Chem. Lett.

      Volume: 2012 Issue: 5 Pages: 482-484

    • DOI

      10.1246/cl.2012.482

    • NAID

      130004426568

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Crystal Structures and Triboluminescence Based on Trifluoromethyl and Pentafluorosulfanyl Substituted Asymmetric N-Phenyl Imide Compounds2012

    • Author(s)
      H. Nakayama, J. Nishida, N. Takada, H. Sato, Y. Yamashita
    • Journal Title

      Chem. Mater

      Volume: 24(4) Issue: 4 Pages: 671-676

    • DOI

      10.1021/cm202650u

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Enhanced performance of dye-sensitized solar cells with novel 2,6-diphenyl-4H-pyranylidene dyes2012

    • Author(s)
      A. Bolag, J. Nishida, K. Hara, Y. Yamashita
    • Journal Title

      Org. Electronics

      Volume: 13 Issue: 3 Pages: 425-431

    • DOI

      10.1016/j.orgel.2011.11.020

    • NAID

      130004646047

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Characterization, and OFET and OLED Properties of π-Extended Ladder-Type Heteroacenes Based on Indolodibenzothiophene2012

    • Author(s)
      C. Wang, J. Nishida, M. R. Bryce, Y. Yamashita
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 85(1) Issue: 1 Pages: 136-143

    • DOI

      10.1246/bcsj.20110255

    • NAID

      130004152975

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation and n-type FET characteristics of substituted diindenopyrazinediones and bis(dicyanomethylene) derivatives2012

    • Author(s)
      J. Nishida, H. Deno, S. Ichimura, T.Nakagawa, Y. Yamashita
    • Journal Title

      J. Mater. Chem.

      Volume: 22(10) Issue: 10 Pages: 4483-4490

    • DOI

      10.1039/c2jm14955a

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Diazaboroles with quinone units: hydrogen bonding network and n-type FETs involving a three-coordinate boron atom2011

    • Author(s)
      J. Nishida, T. Fujita, Y. Fujisaki, S. Tokito, Y. Yamashita
    • Journal Title

      J. Mater. Chem.

      Volume: 21(41) Issue: 41 Pages: 16442-16447

    • DOI

      10.1039/c1jm12650d

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] n-Type Field-effect Transistors Based on Thieno [3,2-b] thiophene-2.5-dione and the Bis (dicyanomethylene) Derivatives2011

    • Author(s)
      S.Chen, A.Bolag, J.Nishida, Y.Yamashita
    • Journal Title

      Chem.Lett.

      Volume: 40 Issue: 9 Pages: 998-1000

    • DOI

      10.1246/cl.2011.998

    • NAID

      10029522471

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and n-Type Field-effect Transistor Characteristics of Dioxopyrrolopyrrole Derivatives2011

    • Author(s)
      Y. Suna, J. Nishida, Y. Fujisaki, Y. Yamashita
    • Journal Title

      Chem. Lett.

      Volume: 40(8) Issue: 8 Pages: 822-824

    • DOI

      10.1246/cl.2011.822

    • NAID

      130004426278

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dye-Sensitized Solar Cells Based on Novel Diphenypyran Derivatives2011

    • Author(s)
      A. Bolag, J. Nishida, K. Hara, Y. Yamashita
    • Journal Title

      Chem. Lett.

      Volume: 40(5) Issue: 5 Pages: 510-511

    • DOI

      10.1246/cl.2011.510

    • NAID

      130004426212

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organic Field-effect Transistors Based on Novel Organic Semiconductors Containing Diazaboroles2011

    • Author(s)
      T. Kojima, D. Kumaki, J. Nishida, S. Tokito, Y. Yamashita
    • Journal Title

      J. Mater. Chem.

      Volume: 21(18) Issue: 18 Pages: 6607-6613

    • DOI

      10.1039/c1jm00002k

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Organic Field-effect Transistors Based on Novel Organic Semiconductors Containing Diazaboroles2011

    • Author(s)
      T.Kojima, D.Kumaki, J.Nishida, S.Tokito, Y.Yamashita
    • Journal Title

      Journal of Materials Chemistry

      Volume: (In press)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] n- and p-Channel field-effect transistors based on diquinoxalinoTTF derivatives2010

    • Author(s)
      N. Borjigin, J. Nishida, S. Tokito, L. Theogarajan, Y. Yamashita
    • Journal Title

      Synthetic Metals

      Volume: 160(21-22) Issue: 21-22 Pages: 2323-2328

    • DOI

      10.1016/j.synthmet.2010.09.005

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Design of Organic Dye toward Retardation of Charge Recombination at Semiconductor/Dye/Electrolyte Interface: Introduction of Twisted π-Linker2010

    • Author(s)
      J. Nishida, T. Masuko, Y. Cui, K. Hara, H. Shibuya, M. Ihara, T. Hosoyama, R. Goto, S. Mori, Y. Yamashita
    • Journal Title

      J. Phys. Chem. C

      Volume: 114(41) Issue: 41 Pages: 17920-17925

    • DOI

      10.1021/jp912047u

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and characterization of 1,3,2-diazaboroine derivatives for organic thin-film transistor applications2010

    • Author(s)
      Y. Lu, A. Bolag, J. Nishida, Y. Yamashita
    • Journal Title

      Synthetic Metals

      Volume: 160(17-18) Issue: 17-18 Pages: 1884-1891

    • DOI

      10.1016/j.synthmet.2010.07.004

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and FET characteristics of phenylene-vinylene and anthracene-vinylene compounds containing cyano groups2010

    • Author(s)
      K. Shoji, J. Nishida, D. Kumaki, S. Tokito, Y. Yamashita
    • Journal Title

      J. Mater. Chem.

      Volume: 20(31) Issue: 31 Pages: 6472-6478

    • DOI

      10.1039/c0jm00715c

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] n- and p-Channel Field-Effect Transistors Based on DiquinoxalinoTTF derivatives2010

    • Author(s)
      N.Borjigin, J.Nishida, S.Tokito, L.Theogarajan, Y.Yamashita
    • Journal Title

      Synthetic Metals

      Volume: 160 Pages: 2323-2328

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Design of Organic Dye toward Retardation of Charge Recombination at Semiconductor/Dye/Electrolyte Interface : Introduction of Twisted pi-Linker2010

    • Author(s)
      J.Nishida, T.Masuko, C.Y.Cui, K.Hara, H.Shibuya, M.Ihara, T.Hosoyama, R.Goto, S.Mori, Y.Yamashita
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 114 Pages: 17920-17925

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and FET Characteristics of Phenylene-vinylene and Anthracene-vinvlene Compounds Containing Cvano Groups2010

    • Author(s)
      K.Shoji, J.Nishida, D.Kumaki, S.Tokito, Y.Yamashita
    • Journal Title

      Journal of Materials Chemistry

      Volume: 20 Pages: 6472-6478

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] チオフェン置換されたトリフルオロメチ ルフェニルイミド化合物の性質とトリボルミネッセンス2013

    • Author(s)
      長谷川弘侑, 西田純一, 高田徳幸, 山下敬郎
    • Organizer
      電気化学会第80回大会
    • Place of Presentation
      仙台
    • Related Report
      2012 Final Research Report
  • [Presentation] チオフェン置換されたトリフルオロメチルフェニルイミド化合物の性質とトリボルミネッセンス2013

    • Author(s)
      長谷川弘侑・西田純一・高田徳幸・山下敬郎
    • Organizer
      電気化学会第80回大会
    • Place of Presentation
      東北大学川内キャンパス(宮城県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] トリフルオロメチルフェニル基を有するカルバゾール誘導体の合成とトリボルミネッセンス2013

    • Author(s)
      長峯巧弥・西田純一・山下敬郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] トリイソプロピルシリルエチニル基を有するジシアノテトラアザアセン類の合成と物性2013

    • Author(s)
      楊帆・西田純一・山下敬郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] ピラジン骨格を有する新規色素の合成と色素増感太陽電池への応用2013

    • Author(s)
      寺田絢香・西田純一・山下敬郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 新規なDPP誘導体の合成と有機薄膜太陽電池のn型有機半導体への応用2013

    • Author(s)
      伊藤晋平・西田純一・山下敬郎
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 非対称化合物の合成と光学特性2012

    • Author(s)
      西田純一, 中山光, 永山裕樹, 長谷川弘侑, 大山将史, 長峰巧弥, 高田徳幸, 佐藤寛泰, 山下敬郎
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Final Research Report
  • [Presentation] Preparation, properties and FET characteristics of diindenopyrazinediones and related compounds2012

    • Author(s)
      Jun-ichi Nishida, Hironori Deno, Satoru Ichimura, Tomohiro Nakagawa, Yo shiro Yamashita
    • Organizer
      2012 International Conference on Flexible and Printed Electronics (2012ICFPE)
    • Place of Presentation
      Tokyo
    • Related Report
      2012 Final Research Report
  • [Presentation] アリール置換されたインデノフルオレン誘導体の合成、結晶構造と物性2012

    • Author(s)
      西田純一, 塚口晋吾, 山下敬郎
    • Organizer
      第21回有機結晶シンポジ ウム
    • Place of Presentation
      横浜
    • Related Report
      2012 Final Research Report
  • [Presentation] トリフルオロメチルフェニル基を導入したカルバゾール誘導体の合成と物性2012

    • Author(s)
      長峯巧弥・西田純一・山下敬郎
    • Organizer
      第6回有機π電子系シンポジウム
    • Place of Presentation
      松山(愛媛県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] アリール置換されたインデノフルオレン誘導体の合成、結晶構造と物性2012

    • Author(s)
      西田純一・塚口晋吾・山下敬郎
    • Organizer
      第21回有機結晶シンポジウム
    • Place of Presentation
      東京工業大学すずかけ台キャンパス(神奈川県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] チオフェン縮環イミド化合物の構造と物性2012

    • Author(s)
      原正敏・西田純一・山下敬郎
    • Organizer
      第21回有機結晶シンポジウム
    • Place of Presentation
      東京工業大学すずかけ台キャンパス(神奈川県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] アリール基を導入したテトラシアノアントラキノジメタン誘導体の結晶構造と物性2012

    • Author(s)
      千葉宙・西田純一・山下敬郎
    • Organizer
      第21回有機結晶シンポジウム
    • Place of Presentation
      東京工業大学すずかけ台キャンパス(神奈川県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 非対称化合物の合成と光学特性2012

    • Author(s)
      西田純一・中山光・永山裕樹・長谷川弘侑・大山将史・長峰巧弥・高田徳幸・佐藤寛泰・山下敬郎
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 2-フェニル-1,3,2-ベンゾジアザボロール誘導体の合成と物性2012

    • Author(s)
      大山将史・永山裕樹・西田純一・山下敬郎
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 水素結合型ジケトピロロピロールーチオフェンコオリゴマーの電解効果トランジスタ特性2012

    • Author(s)
      砂有紀・西田純一・山下敬郎
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 有機π電子化合物の分子配列制御と固体薄膜物性に関する研究2011

    • Author(s)
      西田純一
    • Organizer
      電気化学会第78回大会
    • Place of Presentation
      朱鷺メッセ(新潟市)(依頼講演2H11)(招待講演)
    • Year and Date
      2011-09-10
    • Related Report
      2011 Annual Research Report
  • [Presentation] 有機π電子化合物の分子配列制御と固体薄膜物性に関する研究2011

    • Author(s)
      西田純一
    • Organizer
      2011年電気化学秋季大会(依頼講演)
    • Place of Presentation
      新潟
    • Related Report
      2012 Final Research Report
  • [Presentation] physical properties and FET characteristics of diindenopyrazinediones and related compounds2011

    • Author(s)
      Jun-ichi Nishida, Satoru Ichimura, Hironori Deno, Tomohiro Nakagawa, Yoshiro Yamashita、 Preparation
    • Organizer
      10th International Symposium on Organic Reactions (ISOR10)
    • Place of Presentation
      Tokyo
    • Related Report
      2012 Final Research Report
  • [Presentation] Preparation, physical properties and FET characteristics of planar π-conjugated molecules containing diazaborole and quinone units2011

    • Author(s)
      Jun-ichi Nishida, Takahiro Kojima, Tomohiro Fujita, Yinxiang Lu, Yoshihide Fujisaki, Shizuo Tokito, Yoshiro Yamashita
    • Organizer
      10th International Symposium of functional pi-electron systems (Fπ10)
    • Place of Presentation
      Beijing, China
    • Related Report
      2012 Final Research Report
  • [Presentation] ジアザボロール及びジアザボリニンで架橋された平面π電子化合物の物性と半導体的性質2010

    • Author(s)
      西田純一、小島崇寛、呂銀祥、藤田智博、藤崎好英、時任静士、山下敬郎
    • Organizer
      第37回有機典型元素化学討論会
    • Place of Presentation
      室蘭市民会館ホール(室蘭市輪西町)
    • Year and Date
      2010-11-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] ジアゾボロール及びジアザボリニン誘導体で架橋された平面π電子化合物の物性と半導体的性質2010

    • Author(s)
      西田純一, 小島崇寛, 呂銀祥, 藤田智博,藤崎好英, 時任静士, 山下敬郎
    • Organizer
      第37回有機典型元素化学討論会
    • Place of Presentation
      室蘭
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis and n-type FET characteristics ofphenylene-vinylene compounds containing cyano groups2010

    • Author(s)
      Jun-ichi Nishida, Kohei Shoji, Daisuke Kumaki, Shizuo Tokito, Yoshiro Yamashita
    • Organizer
      The International Conference on Science and Technology of Synthetic Metals(ICSM-2010)
    • Place of Presentation
      Kyoto
    • Related Report
      2012 Final Research Report
  • [Remarks] 山下研究室のホームページにようこそ

    • URL

      http://www.echem.titech.ac.jp/~yamashita/index.html

    • Related Report
      2012 Final Research Report
  • [Remarks] 山下研究室のホームページにようこそ

    • URL

      http://www.echem.titech.ac.jp/~yamashita/index1.html

    • Related Report
      2012 Annual Research Report
  • [Remarks]

    • URL

      http://www.echem.titech.ac.jp/~yamashita/index.html

    • Related Report
      2011 Annual Research Report

URL: 

Published: 2010-08-23   Modified: 2019-07-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi