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2012 Fiscal Year Final Research Report

Research of organic electronics using novel nitrogen heterocyclic compounds

Research Project

  • PDF
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
Keywords有機半導体デバイス / 有機合成化学
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).

  • Research Products

    (28 results)

All 2013 2012 2011 2010 Other

All Journal Article (18 results) (of which Peer Reviewed: 18 results) Presentation (9 results) Remarks (1 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) Pages: 3097-3101

    • DOI

      DOI:10.1016/j.orgel.2012.09.005

    • 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) Pages: 3994-4000

    • DOI

      DOI:10.1021/am300822z

    • 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) Pages: 3356-3359

    • DOI

      DOI:10.1021/ol3013364

    • 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) Pages: 8964-8970

    • DOI

      DOI:10.1002/chem..201200591

    • 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) Pages: 671-676

    • DOI

      DOI:10.1021/cm202650u

    • 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 Pages: 425-431

    • DOI

      DOI:10.1016/j.orgel.2011.11.020

    • 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) Pages: 136-143

    • DOI

      DOI:10.1246/bcsj.20110255

    • 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) Pages: 4483-4490

    • DOI

      DOI:10.1039/C2JM14955A

    • 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) Pages: 16442-16447

    • DOI

      DOI:10.1039/C1JM12650D

    • 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(9) Pages: 998-1000

    • DOI

      DOI:10.1246/cl.2011.998

    • 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) Pages: 822-824

    • DOI

      DOI:10.1246/cl.2011.822

    • 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) Pages: 510-511

    • DOI

      DOI:10.1246/cl.2011.510

    • 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) Pages: 6607-6613

    • DOI

      DOI:10.1039/C1JM00002K

    • 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) Pages: 2323-2328

    • DOI

      DOI:10.1016/j.synthmet.2010.09.005

    • 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) Pages: 17920-17925

    • DOI

      DOI:10.1021/jp912047u

    • 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) Pages: 1884-1891

    • DOI

      DOI:10.1016/j.synthmet.2010.07.004

    • 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) Pages: 6472-6478

    • DOI

      DOI:10.1039/C0JM00715C

    • Peer Reviewed
  • [Journal Article] Tetracyanoanthraquinodimethanes Having Biaryl Substituents: Synthesis, Crystal Structures, and Physical Properties

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

      Chem. Lett.

      Volume: 2012 Pages: 482-484

    • DOI

      DOI:10.1246/cl.2012.482

    • 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
    • Year and Date
      20130329-31
  • [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
    • Year and Date
      20121108-10
  • [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
    • Year and Date
      20120919-21
  • [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
    • Year and Date
      20120906-08
  • [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
    • Year and Date
      20111121-24
  • [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
    • Year and Date
      20111013-17
  • [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
    • Year and Date
      20110909-11
  • [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
    • Year and Date
      20101125-27
  • [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
    • Year and Date
      20100704-09
  • [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

URL: 

Published: 2014-08-29  

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