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Delopment of n-type oraganic semiconductors based on operating mechanism and establishment of rational molecular design

Research Project

Project/Area Number 16H04191
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic and hybrid materials
Research InstitutionOsaka University

Principal Investigator

Ie Yutaka  大阪大学, 産業科学研究所, 准教授 (80362622)

Research Collaborator Aso Yoshio  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥16,380,000 (Direct Cost: ¥12,600,000、Indirect Cost: ¥3,780,000)
Fiscal Year 2018: ¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2017: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2016: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Keywords有機導体 / 有機半導体材料 / 有機電界効果トランジスタ / 有機薄膜太陽電池 / 電子輸送性材料 / 有機薄膜型太陽電池
Outline of Final Research Achievements

We developed organic semiconducting materials based on pi-conjugated systems for use in organic field-effect transistors (OFETs) and organic photovoltaics (OPVs). Especially, we focused on the development of electron-accepting pi-conjugated systems for the application to electron-transporting (n-type) materials. For these purposes, we designed and synthesized a series of novel electronegative pi-conjugated units. Our newly synthesized pi-conjugated systems containing these units showed typical n-type characterisitics in OFETs or OPVs. Based on the results of physical measurements and device perfomances, we revealed structure-property-device function relationship. These results suggest the rational molecular design of n-type organic semiconductors for realization of high-performance OFETs or OPVs.

Academic Significance and Societal Importance of the Research Achievements

有機エレクトロニクスは次世代の電子デバイスとして有望視されている。しかし、材料開発の面から克服すべき課題が山積みの状況である。構造有機化学に基づく分子合成からOFET,OPV材料への応用に向けて研究を遂行し、構造物性機能相関の解明と材料としての高性能化に基づく設計指針の確立を達成できれば、材料開発のブレークスルーに直接的につながる。すなわち本研究は、学理追求型研究であるが産業的にもインパクトの高いチャレンジングな研究である点で学術的意義を有する。また、次世代エレクトロニクスに繋がる本研究は、高度技術化の利便性を享受しつつ人類の持続的発展に寄与する基盤を構築する点で社会的意義を満たすものである。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (50 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (2 results) Journal Article (14 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 14 results,  Open Access: 5 results,  Acknowledgement Compliant: 5 results) Presentation (33 results) (of which Int'l Joint Research: 13 results,  Invited: 19 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] マックスプランク高分子研究所(ドイツ)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] マックスプランク高分子研究所(ドイツ)

    • Related Report
      2017 Annual Research Report
  • [Journal Article] Synthesis, Properties, and Photovoltaic Characteristics of Donor-Acceptor Copolymers Based on Tetrafluoro-Substituted Benzodioxocyclohexene-Annelated Thiophene2018

    • Author(s)
      Y. Ie, Y. Kishimoto, K. Morikawa, Y. Aso
    • Journal Title

      Journal of Photopolymer Science and Technology

      Volume: 31 Issue: 2 Pages: 145-150

    • DOI

      10.2494/photopolymer.31.145

    • NAID

      130007481532

    • ISSN
      0914-9244, 1349-6336
    • Year and Date
      2018-06-25
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Antiaromatic character of cycloheptatriene-bis-annelated indenofluorene framework mainly originated from heptafulvene segment2018

    • Author(s)
      Yamamoto, Keitaro; Ie, Yutaka; Tohnai, Norimitsu; Kakiuchi, Fumitoshi; Aso, Yoshio
    • Journal Title

      Scientific Reports

      Volume: 8 Issue: 1 Pages: 1-11

    • DOI

      10.1038/s41598-018-35839-w

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] A Thiazole-Fused Antiaromatic Compound Containing an s-Indacene Chromophore with a High Electron Affinity2018

    • Author(s)
      Y. Ie, C. Sato, K. Yamamoto, M. Nitani, Y. Aso
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 12 Pages: 1534-1537

    • DOI

      10.1246/cl.180818

    • NAID

      130007534780

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorinated Naptho[1,2-c:5,6-c']bis[1,2,5]thiadiazole-Containing pi-Conjugated Compound: Synthesis, Properties, and Acceptor Application in Organic Solar Cells2018

    • Author(s)
      S. Chatterjee, Y. Ie, T. Seo, T. Moriyama, G.-J. A. H. Wetzelaer, P. W. M. Blom, Y. Aso
    • Journal Title

      NPG Asia Mater.

      Volume: 10 Issue: 10 Pages: 1016-1028

    • DOI

      10.1038/s41427-018-0088-4

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Oligothiophene Quinoids Containing a Benzo[c]thiophene Unit for the Stabilization of the Quinoidal Electronic Structure2018

    • Author(s)
      K. Yamamoto, Y. Ie, M. Nitani, N. Tohnai, F. Kakiuchi, K. Zhang, W. Pisula, K. Asadi, P. W. M. Blom, Y. Aso
    • Journal Title

      J. Mater. Chem. C

      Volume: 6 Issue: 28 Pages: 7493-7500

    • DOI

      10.1039/c8tc01802b

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole-Based Nonfullerene Acceptors: Effect of Substituents on the Thiophene Unit on Properties and Photovoltaic Characteristics2018

    • Author(s)
      S. Chatterjee, Y. Ie, Y. Aso
    • Journal Title

      ACS Omega

      Volume: 3 Issue: 5 Pages: 5814-5824

    • DOI

      10.1021/acsomega.8b00350

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enhanced Photovoltaic Performance of Amorphous Donor-Acceptor Copolymers Based on Fluorine-Substituted Benzodioxocyclohexene-Annelated Thiophene2017

    • Author(s)
      Y. Ie, K. Morikawa, W. Zajazkowski, W. Pisula, N. B. Kotadiya, G.-J. A. H. Wetzelaer, P. W. M. Blom, Y. Aso
    • Journal Title

      Adv. Energy Mater.

      Volume: 7 Issue: 13

    • DOI

      10.1002/aenm.201702506

    • Related Report
      2018 Annual Research Report 2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis, properties, and photovoltaic characteristics of p-type donor copolymers having fluorine-substituted benzodioxocyclohexene-annelated thiophene2017

    • Author(s)
      Y. Ie, K. Morikawa, M. Karakawa, N. B. Kotadiya, G.-J. A. H. Wetzelaer, P. W. M. Blom, Y. Aso
    • Journal Title

      J. Mater. Chem. A

      Volume: 5 Issue: 37 Pages: 19773-19780

    • DOI

      10.1039/c7ta05822e

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Influence of Terminal Imide Units on Properties and Photovoltaic Characteristics for Benzothiadiazole-based Nonfullerene Acceptors2017

    • Author(s)
      S. Chatterjee, Y. Ie, Y. Aso
    • Journal Title

      Journal of Photopolymer Science and Technology

      Volume: 30 Issue: 5 Pages: 557-560

    • DOI

      10.2494/photopolymer.30.557

    • NAID

      130005950303

    • ISSN
      0914-9244, 1349-6336
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Three-dimensional pi-conjugated compounds as non-fullerene acceptors in organic photovoltaics: the influence of acceptor unit orientation at phase interfaces on photocurrent generation efficiency2017

    • Author(s)
      S. Jinnai, Y. Ie, Y. Kashimoto, H. Yoshida, M. Karakawa, Y. Aso
    • Journal Title

      J. Mater. Chem. A.

      Volume: 5 Issue: 8 Pages: 3932-3938

    • DOI

      10.1039/c6ta10608k

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Electron-Accepting pi-Conjugated Molecules with Fluorine-Containing Dicyanovinylidene as Terminal Groups: Synthesis, Properties, and Semiconducting Characteristics2016

    • Author(s)
      Y. Ie, A. Uchida, N. Kawaguchi, M. Nitani, H. Tada, F. Kakiuchi, and Y. Aso
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 17 Pages: 4320-4323

    • DOI

      10.1021/acs.orglett.6b02070

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Properties, and Photovoltaic Performance of a Donor-Acceptor Copolymer Having Pyradinobisthiazole as the Acceptor Unit2016

    • Author(s)
      Y. Ie, S. Sasada, M. Karakawa, Y. Aso
    • Journal Title

      Journal of Photopolymer Science and Technology

      Volume: 29 Issue: 4 Pages: 571-574

    • DOI

      10.2494/photopolymer.29.571

    • NAID

      130005261799

    • ISSN
      0914-9244, 1349-6336
    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Electron-Accepting pi-Conjugated Systems for Organic Photovoltaics: Influence of Structural Modification on Molecular Orientation at Donor-Acceptor Interfaces2016

    • Author(s)
      S. Jinnai, Y. Ie, M. Karakawa, T. Aernouts, Y. Nakajima, S. Mori, Y. Aso
    • Journal Title

      Chem. Mater.

      Volume: 28 Issue: 6 Pages: 1705-1713

    • DOI

      10.1021/acs.chemmater.5b04551

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole-Containing pi-Conjugated Compound: Non-fullerene Electron Acceptor for Organic Photovoltaics2016

    • Author(s)
      S. Chatterjee, Y. Ie, M. Karakawa, Y. Aso
    • Journal Title

      Adv. Funct. Mater.

      Volume: 26 Issue: 8 Pages: 1161-1168

    • DOI

      10.1002/adfm.201504153

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] チオフェン縮環ナフトビスチアジアゾールを用いた半導体ポリマーの合成、物性、および、光電変換特性2019

    • Author(s)
      坂井泰士、森山太一、家 裕隆
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] フッ素化ベンゾジチオフェン-4, 8-ジオンをアクセプターユニットとするπ 共役コポリマーの合成と物性、および太陽電池特性2019

    • Author(s)
      岸本陽太、安蘇芳雄、家 裕隆
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] フッ素原子を導入したキノイドオリゴチオフェンの合成、物性、および半導体特性2019

    • Author(s)
      山本恵太郎、家 裕隆
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 含フッ素アクセプターを導入したπ共役系の開発と太陽電池応用2019

    • Author(s)
      家 裕隆
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 含フッ素ジオキソシクロアルケン縮環チオフェンをアクセプターユニットとするπ共役コポリマーの合成と物性、および太陽電池特性2019

    • Author(s)
      岸本陽太、安蘇芳雄、家 裕隆
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 構造物性機能相関に基づく有機薄膜太陽電池材料の開発2019

    • Author(s)
      家 裕隆
    • Organizer
      電気化学会第86回大会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] フッ素置換ナフトビスチアジアゾールをユニットとする電子受容性π共役分子の合成、物性、光電変換特性2018

    • Author(s)
      家 裕隆、Shreyam Chatterjee、伊津野 翔、Gert-Jan A. H. Wetzelaer、Paul W. M. Blom、安蘇芳雄
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 有機薄膜太陽電池への応用に向けた含フッ素ジオキソシクロアルケン縮環チオフェンを用いたアモルファス性ドナーポリマーの開発2018

    • Author(s)
      家 裕隆、森川功貴、岸本陽太、Gert-Jan A. H. Wetzelaer、Paul W. M. Blom、安蘇芳雄
    • Organizer
      第67回高分子討論会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Synthesis, Properties, and Photovoltaic Characteristics of Donor-Acceptor Copolymers Based on Tetrafluoro-substituted Benzodioxocyclohexene-annelated Thiophene2018

    • Author(s)
      Yutaka Ie
    • Organizer
      The 35rd International Conference of Photopolymer Science and Technology (ICPST-35)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Organic Photovoltaic Materials Containing Fluorine-Substituted Electron-Accepting Units2018

    • Author(s)
      Yutaka Ie
    • Organizer
      14th IUPAC International Conference on Novel Materials and their Synthesis (NMS-XIV)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of organic photovoltaic materials containing new electron-accepting units2018

    • Author(s)
      Yutaka Ie
    • Organizer
      ThinFilms2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Donor and Acceptor Materials Containing Fluorine-Substituted Electron-Accepting Units for Organic Photovoltaics2018

    • Author(s)
      Yutaka Ie
    • Organizer
      International Conference on Emerging Advanced Nanomaterials (ICEAN) 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 共役長を制御した単分子ワイヤの物性と電気伝導特性2018

    • Author(s)
      家 裕隆
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] フッ素含有ベンゾジオキソシクロアルケン縮環チオフェンをアクセプターユニットとする新規π 共役ポリマーの合成と物性、および太陽電池特性2018

    • Author(s)
      岸本陽太、森川功貴、家 裕隆、安蘇 芳雄
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] n 型有機半導体を指向したテトラゾロピリジンを含むπ共役系分子の合成と物性2018

    • Author(s)
      丹波俊輔、田中 光、萩谷一剛、家 裕隆、安蘇芳雄
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] フッ素置換ナフトビスチアジアゾールを用いた新規n 型半導体ポリマーの合成、物性、および、光電変換特性2018

    • Author(s)
      伊津野 翔、家 裕隆、安蘇芳雄
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Fluorinated Naphtho[1,2-c:5,6-c']bis[1,2,5]thiadiazole -based Non-fullerene Electron Acceptor for Organic Solar Cell2018

    • Author(s)
      Shreyam Chatterjee, Yutaka Ie, Yoshio Aso
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Development of novel units for single-molecule-based electronics2018

    • Author(s)
      Yutaka Ie
    • Organizer
      International workshop on molecular workshop
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] キノイド構造の安定化を指向してベンゼン縮環構造を導入したキノイドオリゴチオフェンの合成および物性2017

    • Author(s)
      山本恵太郎、家 裕隆、二谷真司、垣内史敏、安蘇芳雄
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶応義塾大学・日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] ナフトビスチアジアゾールを含む電子輸送型ポリマーの合成、物性、および、太陽電池特性評価2017

    • Author(s)
      伊津野 翔、家 裕隆、安蘇芳雄
    • Organizer
      第11回有機π電子系シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] テトラゾロピリジン骨格を含む高分子半導体材料の開発2017

    • Author(s)
      丹波俊輔、萩谷一剛、家 裕隆、安蘇芳雄
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Non-fullerene Acceptors for Application to Organic Photovoltaics: Structures-Thin-film Properties-Photovoltaic Characteristics Relationship2017

    • Author(s)
      Yutaka Ie
    • Organizer
      13th International Conference of Computational Methods in Science and Engineering
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of New pi-Conjugated Systems towards Electronic Device Applications2017

    • Author(s)
      Yutaka Ie
    • Organizer
      ISPAC 2017 International Symposium on Pure & Applied Chemistry 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Novel pi-Conjugated Systems for Organic Semiconducting Materials2017

    • Author(s)
      Yutaka Ie
    • Organizer
      81st Prague Meeting on Macromolecules
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of donor-acceptor copolymers based on fluorine-substituted benzodioxocyclohexene-annelated thiophene2017

    • Author(s)
      Yutaka Ie
    • Organizer
      1st SANKEN JSPS Symposium for the Circulation of Talented Researchers “Global Networking on Molecular Technology Research
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 縮環構造を導入したキノイド型オリゴチオフェンの合成、物性、および電子輸送特性2016

    • Author(s)
      山本恵太郎、家裕隆、二谷真司、垣内史敏、安蘇芳雄
    • Organizer
      第43回有機典型元素化学討論会
    • Place of Presentation
      仙台市民会館
    • Year and Date
      2016-12-08
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of Novel pi-Conjugated Systems for Electronic Application: Chemical Structures-Properties-Function Relationship2016

    • Author(s)
      Yutaka Ie, Yoshio Aso
    • Organizer
      The 14th International Conference on Frontiers of Polymers and Advanced Materials
    • Place of Presentation
      Deajeon, Korea
    • Year and Date
      2016-10-31
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of New pi-Conjugated Compounds towards Single-molecule Electronics and Thin-film Electronics2016

    • Author(s)
      Yutaka Ie, Yoshio Aso
    • Organizer
      IUPAC 12th International Conference on Novel Materials and their Synthesis
    • Place of Presentation
      Changsha, China
    • Year and Date
      2016-10-14
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 薄膜エレクトロニクスへの応用に向けた新規電子受容性ユニットに基づく有機半導体材料の開発2016

    • Author(s)
      家 裕隆
    • Organizer
      有機エレクトロニクスデバイス・材料に関する研究討論会
    • Place of Presentation
      銀杏会館
    • Year and Date
      2016-09-30
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Development of Electron-Transporting pi-Conjugated Systems for Organic Semiconducting Materials2016

    • Author(s)
      Yutaka Ie
    • Organizer
      International Conference on Flexible and Printed Electronics
    • Place of Presentation
      Yamagata University
    • Year and Date
      2016-09-06
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] フッ素含有ベンゾジオキソシクロアルケン縮環チオフェンをアクセプターユニットとする新規π共役コポリマーの開発:フッ素置換基が物性と太陽電池特性に与える影響2016

    • Author(s)
      森川功貴、家裕隆、辛川誠、安蘇芳雄
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島平和記念公園
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機薄膜型太陽電池に向けた非フラーレン系アクセプター材料の開発:構造と薄膜物性と光電変換特性の相関2016

    • Author(s)
      家 裕隆
    • Organizer
      第12回有機太陽電池シンポジウム
    • Place of Presentation
      おうばくプラザ
    • Year and Date
      2016-07-14
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Synthesis, Properties, and Photovoltaic Performance of Copolymers Having New Electron-Accepting Units2016

    • Author(s)
      Yutaka Ie
    • Organizer
      The 33rd International Conference of Photopolymer Science and Technology
    • Place of Presentation
      Makuhari Messe, Chiba
    • Year and Date
      2016-06-22
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Patent(Industrial Property Rights)] ナフトビスカルコゲナジアゾール誘導体2016

    • Inventor(s)
      家裕隆、安蘇芳雄、瀬尾卓司、森山太一
    • Industrial Property Rights Holder
      家裕隆、安蘇芳雄、瀬尾卓司、森山太一
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-254351
    • Filing Date
      2016-12-27
    • Related Report
      2016 Annual Research Report

URL: 

Published: 2016-04-21   Modified: 2020-03-30  

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