Development of Electronegative Three-dimensional Conjugated Systems

• Project/Area Number: 22750127
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Functional materials chemistry
• Research Institution: Osaka University
• Principal Investigator: IE Yutaka 大阪大学, 産業科学研究所, 准教授 (80362622)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000); Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
• Keywords: 光物性 / 有機太陽電池 / 有機エレクトロニクス / 有機電界効果トランジタ / 薄膜型有機太陽電池 / 電子輸送性材料 / 共役系分子 / 構造物性機能相関

Research Abstract

A series of three-dimensional pi-conjugated compounds bearing electronegative character was synthesized, and their electronic properties and structures were investigated by spectroscopic and electrochemical measurements. Some of these compounds showed n-type semiconducting behavior on transistor and photovoltaic devices.

Research Products

• [Journal Article] Electron-Transporting Oligothiophenes Containing Dicyanomethylene-Substituted Cyclopenta[ b] thiophene : Chemical Tuning for Air-stability in OFETs (2011)
  • Author(s): Yutaka Ie, Kazufumi Nishida, Makoto Karakawa, Hirokazu Tada, Yoshio Aso
  • Journal Title: J. Org. Chem Volume: 76 Pages: 6604-6610
  • Peer Reviewed
• [Journal Article] Solution-Processable n-Type OFET Materials Based on Carbonyl-Bridged Bithiazole and Dioxocyclopentene-Annelated Thiophenes (2011)
  • Author(s): Masashi Nitani, Yutaka Ie, Hirokazu Tada, Yoshio Aso
  • Journal Title: Chem. Asian. J Volume: 6 Pages: 2352-2361
  • Peer Reviewed
• [Journal Article] Air-Stable n-Type Organic Field-Effect Transistors Based on Solution-Processable, Electronegative Oligomers Containing Dicyanomethylene-Substituted Cyclopenta[b]thiophene (2011)
  • Author(s): Y.Ie, K.Nishida, M.Karakawa, H.Tada, A.Asano, A.Saeki, S.Seki, Y.Aso
  • Journal Title: Chem.Eur.J. Volume: 17 Issue: 17 Pages: 4750-4758
  • DOI: 10.1002/chem.201002995
  • Peer Reviewed
• [Journal Article] Solution-Processable n-Type OFET Materials Based on Carbonyl-Bridged Bithiazole and Dioxocyclopentene-Annelated Thiophenes (2011)
  • Author(s): M.Nitani, Y.Ie, H.Tada, Y.Aso
  • Journal Title: Chem.Asian.J. Volume: 6 Issue: 9 Pages: 2352-2361
  • DOI: 10.1002/asia.201190035
  • Peer Reviewed
• [Journal Article] Electron-Transporting Oligothiophenes Containing Dicyanomethylene-Substituted Cyclopenta[b]thiophene : Chemical Tuning for Air Stability in OFETs (2011)
  • Author(s): Y.Ie, K.Nishida, M.Karakawa, H.Tada, Y.Aso
  • Journal Title: J.Org.Chem. Volume: 76 Issue: 16 Pages: 6604-6610
  • DOI: 10.1021/jo200890b
  • Peer Reviewed
• [Journal Article] Synthesis of Tripodal Anchor Units Having Pyridine or Amine Functional Groups and Their Adsorption Behavior on Metal Electrodes (2011)
  • Author(s): T.Hirose, Y.Ie, Y.Aso
  • Journal Title: Chem.Lett. Volume: 40 Pages: 204-205
  • NAID: 10027815065
  • Peer Reviewed
• [Journal Article] Solution-processed n-Type Organic Field-effect Transistors Based on Electronegative Oligothiophenes Having Fully Oxo-substituted Terthiophenes (2010)
  • Author(s): Yutaka Ie, Masashi Nitani, Hirokazu Tada, Yoshio Aso
  • Journal Title: Org. Electron Volume: 11 Pages: 1740-1745
  • URL: http://dx.doi.org/10.1016/j.orgel.2010.07.014
  • Peer Reviewed
• [Journal Article] Solution-processed n-Type Organic Field-effect Transistors Based on Electronegative Oligothiophenes Having Fully Oxo-substituted Terthiophenes (2010)
  • Author(s): Y.Ie, M.Nitani, H.Tada, Y.Aso
  • Journal Title: Org.Electron. Volume: 11 Pages: 1740-1745
  • Peer Reviewed
• [Journal Article] N-Channel Organic Field-Effect Transistors Containing Carbonyl-Bridged Bithiazole Derivative Fabricated Using Polyfluorene Derivatives as Solution-Processed Buffer Layers (2010)
  • Author(s): H.Kajii, Y.Ie, M.Nitani, Y.Hirose, Y.Aso, Y.Ohmori
  • Journal Title: Org.Electron. Volume: 11 Pages: 1886-1890
  • Peer Reviewed
• [Presentation] ジシアノメチレン基を有するチオフェン系π共役分子の合成、物性、および、電子機能 (2012)
  • Author(s): 陣内青萌、家裕隆、安蘇芳雄
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 神奈川
  • Year and Date: 2012-03-27
• [Presentation] 新規な電子輸送性部位を含む有機半導体材料の開発 (2012)
  • Author(s): 家裕隆
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 神奈川
  • Year and Date: 2012-03-27
• [Presentation] インダセノジチアゾールを基本ユニットとする交互共重合体の合成と物性評価 (2012)
  • Author(s): 植田将史、家裕隆、安蘇芳雄
  • Organizer: 日本化学会第92春季年会
  • Place of Presentation: 神奈川
  • Year and Date: 2012-03-25
• [Presentation] 含フッ素置換基を導入したポリ(3-ヘキシルチオフェン)の合成と物性 (2011)
  • Author(s): 小島彩、辛川誠、家裕隆、永井隆文、安蘇芳雄
  • Organizer: 第38回有機典型元素化学討論会
  • Place of Presentation: 金沢
  • Year and Date: 2011-12-07
• [Presentation] Synthesis, Properties, and Photovoltaic Performances of Copolymers Containing Difluorodioxocyclopentene-annelated Thiophene or Naphtho[ 2, 3-c] thiophene-4, 9-dione (2011)
  • Author(s): Yutaka Ie, Jianming Huang, Makoto Karakawa, Yoshio Aso
  • Organizer: 21st International Photovoltaic Science and Engineering Conference
  • Place of Presentation: 福岡
  • Year and Date: 2011-11-30
• [Presentation] Synthesis, Properties, and Photovoltaic Performances of Copolymers Containing Difluorodioxocyclopentene-annelated Thiophene or Naphtho[2,3-c]thiophene-4,9-dione (2011)
  • Author(s): Yutaka Ie, Jianming Huang, Makoto Karakawa, Yoshio Aso
  • Organizer: 21st International Photovoltaic Science and Engineering Conference
  • Place of Presentation: 福岡
  • Year and Date: 2011-11-30
• [Presentation] 電子輸送性有機半導体材料への応用に向けた新奇π電子系分子の開発 (2011)
  • Author(s): 家裕隆
  • Organizer: 第4回臭素化学懇話会年会
  • Place of Presentation: 宇都宮
  • Year and Date: 2011-11-25
• [Presentation] 電子輸送性有機半導体材料への応用に向けた新奇π電子系分子の開発 (2011)
  • Author(s): 家裕隆
  • Organizer: 第4回臭素化学懇話会年会
  • Place of Presentation: 宇都宮(招待講演)
  • Year and Date: 2011-11-25
• [Presentation] Synthesis, Properties, and n-Type OFET Performances of Electronegativeπ-Conjugated Systems Containing Dicyanomethylene-Substituted Cyclopenta[ b] thiophene (2011)
  • Author(s): Yutaka Ie, Kazufumi Nishida, Makoto Karakawa, Yoshio Aso
  • Organizer: 10th International Symposium on Functional p-Electron Systems
  • Place of Presentation: 北京、中国
  • Year and Date: 2011-10-15
• [Presentation] Synthesis, Properties, and n-Type OFET Performances of Electronegative π-Conjugated Systems Containing Dicyanomethylene-Substituted Cyclopenta[b]thiophene (2011)
  • Author(s): Yutaka Ie, Kazufumi Nishida, Makoto Karakawa, Yoshio Aso
  • Organizer: 10th International Symposium on Functional p-Electron Systems
  • Place of Presentation: 北京
  • Year and Date: 2011-10-15
• [Presentation] 縮環型電子求引性ユニットを含むπ電子系分子の開発と塗布型有機半導体材料への応用 (2011)
  • Author(s): 家裕隆、西田和史、黄建明、二谷真司、辛川誠、安蘇芳雄
  • Organizer: 第60回高分子討論会
  • Place of Presentation: 岡山
  • Year and Date: 2011-09-28
• [Presentation] カルボニル架橋チアゾールを有する縮合多環系n型FET材料の開発 (2011)
  • Author(s): 植田将史、家裕隆、安蘇芳雄
  • Organizer: 第72回応用物理学会学術講演会
  • Place of Presentation: 山形
  • Year and Date: 2011-08-31
• [Presentation] 有機n型半導体材料への応用を指向した新規π共役系化合物の開発 (2011)
  • Author(s): 家裕隆
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-28
• [Presentation] 有機n型半導体材料への応用を指向した新規π共役系化合物の開発 (2011)
  • Author(s): 家裕隆
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜(招待講演)
  • Year and Date: 2011-03-28
• [Presentation] 塗布系n型OFET材料を指向したジシアノメチレンシクロペンテン縮環チオフェンを含む電子受容性オリゴマーの開発 (2011)
  • Author(s): 西田和史、家裕隆、安蘇芳雄
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-27
• [Presentation] ペリレンビス(ジカルボキシイミド)基を周辺部に有する三次元構造n型材料の合成と物性 (2011)
  • Author(s): 櫻井隆裕、家裕隆、安蘇芳雄
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-27
• [Presentation] カルボニル架橋型チアゾール部位を有する電子受容性π電子共役系の合成、物性とn型FET特性 (2011)
  • Author(s): 植田将史、家裕隆、安蘇芳雄
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-27
• [Presentation] ジオキソシクロペンタ[c]チオフェンを含む被覆型電子受容性オリゴチオフェンの合成と物性 (2011)
  • Author(s): 遠藤克、家裕隆、安蘇芳雄
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-27
• [Presentation] 有機太陽電池材料としてのジフルオロジオキソシクロペンテン縮環チオフェンユニットを有する共重合体の合成と評価 (2011)
  • Author(s): 黄建明、家裕隆、辛川誠、安蘇芳雄
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-27
• [Presentation] 単分子エレクトロニクス応用に向けたユニット開発 (2011)
  • Author(s): 家裕隆
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-26
• [Presentation] カルボニル架橋ビチアゾールをコアユニットとする塗布系n型FET材料の開発 (2011)
  • Author(s): 二谷真司、家裕隆、安蘇芳雄
  • Organizer: 第58回応用物理学関係連合講演会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-25
• [Presentation] Air-stable and Solution-processable FET Materials Based Electronegative Oligomers Having Dicyanomethylene Cyclopentene-annelated Thiophene (2011)
  • Author(s): Yutaka Ie, Kazufumi Nishida, Yoshio Aso
  • Organizer: The 14th SANKEN International Symposium 2011
  • Place of Presentation: 滋賀
  • Year and Date: 2011-01-25
• [Presentation] Air-stable and Solution-processable FET Materials Based Electronegative Oligomers Having Dicyanomethylene Cyclopentene-annelated Thiophene (2011)
  • Author(s): Y.Ie, K.Nishida, Y.Aso
  • Organizer: The 14^<th> SANKEN International Symposium 2011
  • Place of Presentation: 滋賀
  • Year and Date: 2011-01-25
• [Presentation] Synthesis and Properties of Twisted Polythiophenes for Organic Electronics Materials (2011)
  • Author(s): M.Karakawa, Y.Ie, Y.Aso
  • Organizer: The 14^<th> SANKEN International Symposium 2011
  • Place of Presentation: 滋賀
  • Year and Date: 2011-01-25
• [Presentation] Development of Conjugated Oligomers Based on Carbonyl-Bridged Bithiazole for Solution-processable n-Type OFET Materials. (2010)
  • Author(s): M.Nitani, Y.Ie, Y.Aso
  • Organizer: Pacifichem 2010
  • Place of Presentation: ハワイ、アメリカ合衆国
  • Year and Date: 2010-12-19
• [Presentation] Synthesis, Properties, and OFET Performances of Conjugated Oligomers Having Bis(dicyanomethylene)difluorocyclopentene-annelated Thiophenes (2010)
  • Author(s): K.Nishida, Y.Ie, Y.Aso
  • Organizer: Pacifichem 2010
  • Place of Presentation: ハワイ、アメリカ合衆国
  • Year and Date: 2010-12-19
• [Presentation] Development of Electronegative pi-Conjugated Systems towards n-Type Organic Field-effect Transistor Materials (2010)
  • Author(s): Yutaka Ie, Yoshio Aso
  • Organizer: Pacifichem 2010
  • Place of Presentation: ハワイ、アメリカ合衆国
  • Year and Date: 2010-12-16
• [Presentation] Development of Electronegative π-Conjugated Systems towards n-Type Organic Field-effect Transistor Materials (2010)
  • Author(s): Y.Ie, Y.Aso
  • Organizer: Pacifichem 2010
  • Place of Presentation: ハワイ、アメリカ合衆国
  • Year and Date: 2010-12-16
• [Presentation] カルボニル架橋を有する含チアゾール新規π共役分子の合成、物性、及びFET特性 (2010)
  • Author(s): 植田将史、家裕隆、安蘇芳雄
  • Organizer: 第37回有機典型元素化学討論会
  • Place of Presentation: 室蘭
  • Year and Date: 2010-11-26
• [Presentation] 塗布系n型FET材料としてのジシアノメチレンシクロペンテン縮環チオフェンを含むオリゴマーの開発 (2010)
  • Author(s): 西田和史、家裕隆、安蘇芳雄
  • Organizer: 第37回有機典型元素化学討論会
  • Place of Presentation: 室蘭
  • Year and Date: 2010-11-25
• [Presentation] 完全オキソ置換オリゴチオフェンの合成、物性、および、塗布系n型FETへの応用 (2010)
  • Author(s): 家裕隆、二谷真司、安蘇芳雄
  • Organizer: 第4回有機π電子シンポジウム
  • Place of Presentation: 神戸
  • Year and Date: 2010-11-19
• [Presentation] π共役を制御したポリチオフェンの合成と電流電圧特性 (2010)
  • Author(s): 辛川誠、家裕隆、安蘇芳雄
  • Organizer: 第4回有機π電子シンポジウム
  • Place of Presentation: 神戸
  • Year and Date: 2010-11-19
• [Presentation] フルオロアルキル基含有フラーレン誘導体 (2010)
  • Author(s): 永井隆文、辛川誠、入田友美、足達健二、金村崇、田中義人、家裕隆、安蘇芳雄
  • Organizer: 第34回フッ素化学討論会
  • Place of Presentation: 札幌
  • Year and Date: 2010-10-19
• [Presentation] フルオロアルキル基含有フラーレン誘導体の有機薄膜太陽電池特性 (2010)
  • Author(s): 辛川誠、永井隆文、入田友美、家裕隆、安蘇芳雄
  • Organizer: 第71回応用物理学会学術講演会
  • Place of Presentation: 長崎
  • Year and Date: 2010-09-15
• [Presentation] カルボニル基を導入したチオフェン、あるいは、チアゾールを骨格とする共役化合物の合成、物性とFET特性 (2010)
  • Author(s): 家裕隆、二谷真司、竹谷純一、関修平、辛川誠、安蘇芳雄
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-10
• [Presentation] 完全オキソ置換により電子受容性を向上させたオリゴチオフェンの合成、物性、および、塗布型FET素子への応用 (2010)
  • Author(s): 二谷真司、家裕隆、安蘇芳雄
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-10
• [Presentation] アンカー部位として両末端に硫黄官能基を有する完全被覆型オリゴチオフェンの合成と物性 (2010)
  • Author(s): 遠藤克、家裕隆、安蘇芳雄
  • Organizer: 第21回基礎有機化学討論会
  • Place of Presentation: 名古屋
  • Year and Date: 2010-09-10
• [Presentation] Synthesis, Properties, and n-Type Performances of pi-Conjugated Systems Containing Carbonyl-Bridged Bithiazole (2010)
  • Author(s): Yutaka Ie, Masashi Nitani, Makoto Karakawa, Yoshio Aso
  • Organizer: International Conference on Science and Technology of Synthetic Metals 2010
  • Place of Presentation: 京都
  • Year and Date: 2010-07-08
• [Presentation] Synthesis, Properties, and n-Type Performances of □-Conjugated Systems Containing Carbonyl-Bridged Bithiazole (2010)
  • Author(s): Y.Ie, M.Nitani, M.Karakawa, Y.Aso
  • Organizer: International Conference on Science and Technology of Synthetic Metals 2010
  • Place of Presentation: 京都
  • Year and Date: 2010-07-08
• [Presentation] Twisted Polythiophenes as a New Organic Memory Materials (2010)
  • Author(s): M.Karakawa, Y.Ie, Y.Aso
  • Organizer: International Conference on Science and Technology of Synthetic Metals 2010
  • Place of Presentation: 京都
  • Year and Date: 2010-07-08
• [Presentation] Dendritic Oligothiophenes Bearing Perylene Bis(dicarboximide) Groups as Active Materials for Photovoltaic Device (2010)
  • Author(s): Yutaka Ie, Toshihiko Uto, Akinori Saeki, Shu Seki, Seiichi Tagawa, Yoshio Aso
  • Organizer: 9th International Symposium on Functional pi-Electron Systems
  • Place of Presentation: アトランタ、アメリカ合衆国
  • Year and Date: 2010-05-27
• [Presentation] Dendritic Oligothiophenes Bearing Perylene Bis(dicarboximide) Groups as Active Materials for Photovoltaic Device (2010)
  • Author(s): Y.Ie, T.Uto, A.Saeki, S.Seki, S.Tagawa, Y.Aso
  • Organizer: 9^<th> International Symposium on Functional pi-Electron Systems
  • Place of Presentation: アトランタ、アメリカ合衆国
  • Year and Date: 2010-05-27
• [Presentation] Development of Oligomers Containing Carbonyl-bridged Bithiazole as Solution-Processible n-Type Organic Field-Effect Transistor Materials (2010)
  • Author(s): M.Nitani, Y.Ie, Y.Aso
  • Organizer: 9^<th> International Symposium on Functional pi-Electron Systems
  • Place of Presentation: アトランタ、アメリカ合衆国
  • Year and Date: 2010-05-27
• [Presentation] ねじれを有するポリチオフェンの合成と素子特性 (2010)
  • Author(s): 辛川誠、家裕隆、安蘇芳雄
  • Organizer: 第59回高分子学会年次大会
  • Place of Presentation: 横浜
  • Year and Date: 2010-05-26
• [Presentation] Air-stable N-Type Organic Field-Effect Transistors Based on Carbonyl Bridged Bithiazole Compound (2010)
  • Author(s): Y.Ie, M.Nitani, M.Karakawa, Y.Aso
  • Organizer: 9^<th> International Symposium on Functional pi-Electron Systems
  • Place of Presentation: アトランタ、アメリカ合衆国
  • Year and Date: 2010-05-25
• [Book] プリンテッドエレクトロニクス技術最前線(分筆) (2010)
  • Author(s): 家裕隆、安蘇芳雄
  • Publisher: シーエムシー出版
• [Book] ヘテロ元素の特性を活かした新機能材料(分筆) (2010)
  • Author(s): 家裕隆、安蘇芳雄
  • Publisher: シーエムシー出版
• [Book] プリンテッドエレクトロニクス技術最前線(分筆)(菅沼克昭監修)"プリンテッドエレクトロニクスに向けた有機半導体材料" (2010)
  • Author(s): 家裕隆、安蘇芳雄
  • Publisher: シーエムシー出版
• [Book] ヘテロ元素の特性を活かした新機能材料(分筆)(中條善樹監修)機能性オリゴチオフェンの開発と有機電界効果トランジスタ材料への応用 (2010)
  • Author(s): 家裕隆、安蘇芳雄
  • Publisher: シーエムシー出版