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Development of thiophene-fused phthalocyanines with high crystallinity and application to organic thin-film devices

Research Project

Project/Area Number 22750171
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Functional materials/Devices
Research InstitutionHiroshima University

Principal Investigator

MIYAZAKI Eigo  広島大学, 大学院・工学研究院, 助教 (00432683)

Project Period (FY) 2010 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2012: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsフタロシアニン / 有機半導体 / 有機薄膜デバイス / 電子デバイス
Research Abstract

In order to improve device performance of organic field-effect transistors (OFETs) and organic photovoltaics (OPVs) based on phthalocyanines (Pcs), I have investigated properties of new porphyrazines with aromatic5-membered fused-ring heterocycle and its π-extended compound, and applied to organic thin-film devices. In this project, I have designed thiophene-fused porphyrazine (Tc), benzothiophene-fused porphyrazine (BTc), and thiadiazole-fused porphrazine (TzPz) as new Pcs. Alkylated Tc- and BTc-based devices showed p-channel characteristics with mobility of ~0.3 cm2 V^<-1>s^<-1> for Tc and ~10^<-2>cm^V^<-1>s^<-1>for BTc. However, alkylated TzPz-based devices showed no field-effect response. Alkylated Tc/C60bilayer OPV showed the efficiency of 1.2%. Whereas other Pcs-based OPVs showed no photovoltaics response. These results indicate that simple modification of molecule by π-extension leads to no improvement of device performance.

Report

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

    (47 results)

All 2012 2011 2010

All Journal Article (32 results) (of which Peer Reviewed: 32 results) Presentation (15 results)

  • [Journal Article] A Soluble alpha-DithienotetrathiafulvaleneDerivative for Organic Field-Effect Transistors2012

    • Author(s)
      I. DOI:, K. Goshome, E. Miyazaki,K. Takimiya
    • Journal Title

      Chem. Lett

      Volume: Vol.41 Issue: 4 Pages: 435-437

    • DOI

      10.1246/cl.2012.435

    • NAID

      130004426558

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of anthra [2,3-b] chalcogenophenes2012

    • Author(s)
      K. Niimi, E. Miyazaki,S. Shinamura, K. Takimiya
    • Journal Title

      Synthesis -Stuttgart

      Volume: 44 Issue: 13 Pages: 2102-2106

    • DOI

      10.1055/s-0031-1291141

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Largely π-Extended Thienoacenes with Internal Thieno[3,2-b]thiophene Substructures: Synthesis, Characterization, and OrganicField-Effect Transistor Applications2012

    • Author(s)
      T. Yamamoto, T. Nishimura, T. Mori, E. Miyazaki, I. Osaka, K. Takimiya
    • Journal Title

      Org.Lett

      Volume: 14 Issue: 18 Pages: 4914-4917

    • DOI

      10.1021/ol302243t

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Organic photovoltaics based on 5-hexylthiophene-fused porphyrazines2012

    • Author(s)
      H. Mori, E. Miyazaki, I. Osaka, K. Takimiya
    • Journal Title

      Org. Electronics

      Volume: 13 Issue: 10 Pages: 1975-1980

    • DOI

      10.1016/j.orgel.2012.05.023

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Orthogonally Functionalized Naphthodithiophenes: Selective Protection and Borylation2012

    • Author(s)
      S. Shinamura, R. Sugimoto, N. Yanai,N. Takemura, T. Kashiki, I. Osaka, E. Miyazaki, K. Takimiya
    • Journal Title

      Org.Lett

      Volume: 14 Issue: 18 Pages: 4718-4721

    • DOI

      10.1021/ol301797g

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Characterization, and Transistor and Solar Cell Applications of A Naphthobisthiadiazole-Based Semiconducting Polymer2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Journal of American Cheimical Society

      Volume: Vol. 134 Issue: 7 Pages: 3498-3507

    • DOI

      10.1021/ja210687r

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Angular-shaped naphthodifurans, naphtho[1, 2-6; 5, 6-6']- and naphtho[2, 1-b; 6, 5-b']- difuran : Are they isoelectronic with chrysene?2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Chemical Communications

      Volume: Vol. 48 Issue: 45 Pages: 5671-5673

    • DOI

      10.1039/c2cc31546g

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] [2, 2']Bi[naphtho[2, 3-b]furanyl] : a versatile organic semiconductor with a furan-furan junction2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Chemical Communications

      Volume: Vol. 48 Issue: 47 Pages: 5892-5894

    • DOI

      10.1039/c2cc31960h

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Isomerically pure anthra[2, 3-b : 6, 7-b']-difuran (anti-ADF), -dithiophene (anti-ADT), and -diselenophene (anti-ADS) : Selective synthesis, electronic structures, and application to organic field-effect transistors2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      The Journal of Organic Chemistry

      Volume: Vol. 77 Issue: 18 Pages: 8099-8111

    • DOI

      10.1021/jo301438t

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Largely π-Extended Thienoacenes with Internal Thieno[3, 2-b] thiophene Substructures : Synthesis, Characterization, and Organic Field-Effect Transistor Applications2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Organic Letters

      Volume: Vol. 14 Pages: 4914-4917

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Orthogonally Functionalized Naphthodithiophenes : SelectiveProtection and Borylation2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Organic Letters

      Volume: Vol. 14 Pages: 4718-4721

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Borylation on Benzo[1,2-b : 4, 5-b']- and Naphtho[1,2-b : 5, 6-b']- dichalcogenophenes : Different Chalcogene Atom Effects on Borylation Reaction Depending on Fused Ring Structure2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Organic Letters

      Volume: Vol. 14 Pages: 5448-5451

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two Isomeric Didecyl-dinaphtho[2,3-b : 2', 3'-f] thieno [3, 2-b] thiophenes : Impact of Alkylation Positions on Packing Structures and Organic Field-effect Transistor Characteristics2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Japanese Journal of Applied Physics

      Volume: Vol. 51 Issue: 11S Pages: 11PD04-11PD04

    • DOI

      10.1143/jjap.51.11pd04

    • NAID

      210000141621

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thienannulation reaction : efficient synthesis of ・-extended thienoacenes applicable to organic semiconductors2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      European Journal of Organic Chemistry

      Volume: Vol. 2 Issue: 2 Pages: 217-227

    • DOI

      10.1002/ejoc.201201139

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Anion effects on the cyclobis(paraquat-p-phenylene) host2012

    • Author(s)
      宮碕栄吾
    • Journal Title

      Chemical Communications

      Volume: Vol. 48 Issue: 42 Pages: 5157-5159

    • DOI

      10.1039/c2cc31225e

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Organic Conductors with Self-assembled Architectures of Biomolecules: Synthesis and Crystal Structures of Nucleobase-functionalized Tetrathiafulvalene Derivatives2012

    • Author(s)
      Y. Morita, 他6人
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 85 Issue: 9 Pages: 995-1006

    • DOI

      10.1246/bcsj.20120102

    • NAID

      130004153120

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Alkylated Dinaphtho[2,3-b:2',3'-f]Thieno[3,2-b] Thiophenes (C-n-DNTTs): Organic Semiconductors for High-Performance Thin-Film Transistors2011

    • Author(s)
      M. J. Kang, I. DOI:, H.Mori, E. Miyazaki,K. Takimiya,M. Ikeda, H. Kuwabara
    • Journal Title

      Adv. Mater

      Volume: Vol.23 Issue: 10 Pages: 222-222

    • DOI

      10.1002/adma.201001283

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] General Synthesis of Dinaphtho [2,3-b:2',3'-f]thieno[3,2-b]thiophene (DNTT) Derivatives2011

    • Author(s)
      K. Niimi, M. J. Kang, E. Miyazaki,I. Osaka, K. Takimiya
    • Journal Title

      Org.Lett

      Volume: Vol.13 Issue: 13 Pages: 3430-3433

    • DOI

      10.1021/ol2010837

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Linear- and Angular-Shaped Naphthodithiophenes : Selective Synthesis, Properties, and Application to Organic Field-Effect Transistors2011

    • Author(s)
      Shoji Shinamura, Itaru Osaka, Eigo Miyazaki, Akiko Nakao, Masakazu Yamagishi, Jun Takeya, Kazuo Takimiya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 13 Pages: 5024-5035

    • DOI

      10.1021/ja110973m

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Simple Oligothiophene-Based Dyes for Dye-Sensitized Solar Cells (DSSCs): Anchoring Group Effects on Molecular Properties and Solar Cell Performance2011

    • Author(s)
      E. Miyazaki, E. Okanishi, Y. Suzuki
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: Vol.84 Issue: 5 Pages: 459-465

    • DOI

      10.1246/bcsj.20100302

    • NAID

      130004152902

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thienoacene-Based Organic Semiconductors2011

    • Author(s)
      K. Takimiya, S. Shinamura, I. Osaka, E. Miyazaki ;et al
    • Journal Title

      Heterocycles

      Volume: Vol.82 Issue: 2 Pages: 1317-1317

    • DOI

      10.3987/com-10-s(e)78

    • Related Report
      2012 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Benzo[1,2-b:3,4-b0:5,6-b00]trithiophene (BTT) Oligomers2011

    • Author(s)
      宮碕栄吾
    • Journal Title

      Journal of Organic Chemistry

      Volume: Vol.76 Issue: 10 Pages: 4061-4070

    • DOI

      10.1021/jo2005044

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Patternable solution-crystallized organic transistors with high charge carrier mobility2011

    • Author(s)
      K.Nakayama, Y.Hirose, J.Soeda, M.Yoshizumi, T.Uemura, M.Uno, W.Li, M.Uno, Jin Kang, M.Yamagishi, Y.Okada, E.Miyazaki, Y.Nakazawa, A.Nakao, K.Takimiya, J.Takeya
    • Journal Title

      ADVANCED MATERIALS

      Volume: 23 Issue: 14 Pages: 1626-1629

    • DOI

      10.1002/adma.201004387

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] General Synthesis of Dinaphtho-[2,3-b:20,30-f]thieno[3,2-b] thiophene (DNTT) Derivatives2011

    • Author(s)
      宮碕栄吾
    • Journal Title

      Organic Letters

      Volume: Vol.13 Pages: 3430-3433

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dianthra[2,3-b:2',3'-f]thieno[3,2-b]thiophene (DATT) : Synthesis, Characterization, and FET Characteristics of New π-Extended Heteroarene with Eight Fused Aromatic Rings2011

    • Author(s)
      Kazuki Niimi, Shoji Shinamura, Itaru Osaka, Eigo Miyazaki, Kazuo Takimiya
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 22 Pages: 8732-8739

    • DOI

      10.1021/ja202377m

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-step synthesis of [1]benzothieno[3,2-b][1]benzothiophene from o-chlorobenzaldehyde2011

    • Author(s)
      宮碕栄吾
    • Journal Title

      Tetrahedron Letters

      Volume: Vol.52 Pages: 285-288

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Air-Stable and High-Mobility Organic Semiconductors Based on Heteroarenes for Field-Effect Transistors2011

    • Author(s)
      Shoji Shinamura, Itaru Osaka, Eigo Miyazaki, Kazuo Takimiya
    • Journal Title

      Heterocycles

      Volume: 83 Issue: 6 Pages: 1187-1204

    • DOI

      10.3987/rev-10-690

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Quinoidal Oligothiophenes with (Acyl) cyanoinethylene Termini : Synthesis, Characterization, Properties, and Solution Processed n-Channel Organic Field-Effect Transistors2011

    • Author(s)
      宮碕栄吾
    • Journal Title

      Chemistry of Materials

      Volume: Vol.23 Issue: 3 Pages: 795-804

    • DOI

      10.1021/cm102109p

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thienoacene-Based Organic Semiconductors2011

    • Author(s)
      Kazuo Takimiya, Shoji Shinamura, Itaru Osaka, Eigo Miyazaki
    • Journal Title

      Advanced Materials

      Volume: 23 Issue: 38 Pages: 4347-4370

    • DOI

      10.1002/adma.201102007

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] ((Alkyloxy)carbonyl)cyanomethylene-Substituted Thienoquinoidal Compounds: a NewClass of Soluble n-Channel Organic Semiconductors for Air-Stable Organic Field-Effect Transistors2010

    • Author(s)
      Y. Suzuki, E. Miyazaki, K. Takimiya
    • Journal Title

      J. Am. Chem. Soc

      Volume: Vol.132 Issue: 30 Pages: 10453-10466

    • DOI

      10.1021/ja103171y

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Properties, Crystal Structures, and Semiconductor Characteristics of Naphtho[1,2-b:5,6-b´]-dithiophene and -diselenophene Derivatives, S. Shinamura2010

    • Author(s)
      E. Miyazaki, K. Takimiya
    • Journal Title

      J. Org. Chem

      Volume: Vol.75 Issue: 4 Pages: 1228-1234

    • DOI

      10.1021/jo902545a

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Unique Three-Dimensional (3D) Molecular Array in Dimethyl-DNTT Crystals: a New Approach to 3D Organic Semiconductors2010

    • Author(s)
      M. J. Kang, T. Yamamoto, S. Shinamura, E. Miyazaki, K. Takimiya
    • Journal Title

      Chem. Sci

      Volume: Vol.1 Pages: 179-183

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Presentation] Synthesis of Benzo[b]thiophene-fused Porphyrazines and Application to Organic Field-Effect Transistor2012

    • Author(s)
      宮碕 栄吾
    • Organizer
      ISOE2012:International Symposium on Organic Electronics 2012
    • Place of Presentation
      沖縄科学技術大学院・大学
    • Year and Date
      2012-10-03
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis of Benzo[b]thiophene-fused Porphyrazines and Application to Organic Field-Effect Transistor2012

    • Author(s)
      宮碕栄吾
    • Organizer
      ISOE2012 International Symposium on Organic Electronics 2012
    • Place of Presentation
      沖縄科学技術大学院大学
    • Year and Date
      2012-10-03
    • Related Report
      2012 Annual Research Report
  • [Presentation] チアゾール縮環ポルフィラジンの合成と物性2012

    • Author(s)
      五百川諒祐
    • Organizer
      日本化学会第92春季年会(2012)
    • Place of Presentation
      慶應義塾大学矢上キャンパス
    • Year and Date
      2012-03-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] オリゴチオフェンを有する新規チオフェン縮環ポルフイラジンの合成と物性2011

    • Author(s)
      五百川諒祐
    • Organizer
      2011年日本化学会西日本大会
    • Place of Presentation
      徳島大学工学部
    • Year and Date
      2011-11-12
    • Related Report
      2011 Annual Research Report
  • [Presentation] ピリジン環を持つオリゴチオフェン系増感色素の合成と太陽電池への応用2011

    • Author(s)
      柳井直幸
    • Organizer
      2011年日本化学会西日本大会
    • Place of Presentation
      徳島大学工学部
    • Year and Date
      2011-11-12
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis of Thiophene-fused Porphyrazines Bearing Quaterthiophenes and Application to Organic Photovoltaics2011

    • Author(s)
      宮碕 栄吾
    • Organizer
      MDF Workshop
    • Place of Presentation
      10
    • Year and Date
      2011-10-17
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis of Thiophene-fused Porphyrazines Bearing Quaterthiophenes and Application to Organic Photovoltaics2011

    • Author(s)
      宮碕栄吾
    • Organizer
      MDF Workshop
    • Place of Presentation
      梅田スカイビルディング
    • Year and Date
      2011-10-07
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis and Properties of Benzo[b]thiophene-fused Porphyrazines2011

    • Author(s)
      宮碕 栄吾
    • Organizer
      14th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      University of Oregon,アメリカオレゴン州
    • Year and Date
      2011-07-24
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis and Properties of Benzo[b]thiophene-fused Porphyrazines2011

    • Author(s)
      宮碕栄吾
    • Organizer
      14th International Symposium on Novel Aromatic Compounds
    • Place of Presentation
      アメリカ(オレゴン)
    • Year and Date
      2011-07-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] 5-Alkylthiophene-fused porphyrazines: application to solution-processed organic thin-film devices2010

    • Author(s)
      宮碕 栄吾
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      Kamehameha Halls IIand IIIConventionCenter,アメリカハワイ州
    • Year and Date
      2010-12-18
    • Related Report
      2012 Final Research Report
  • [Presentation] 5-Alkylthiophene-fused porphyrazines : application to solution-processed organic thin-film devices2010

    • Author(s)
      宮碕栄吾
    • Organizer
      PACIFICHEM 2010
    • Place of Presentation
      ハワイ:Kamehameha HallsII and III(Convention Center)(アメリカ)
    • Year and Date
      2010-12-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] Synthesis of Thiophene-Fused Porphyrazines and Application to Solution-Processed Organic Field-Effect Transistors2010

    • Author(s)
      宮碕 栄吾
    • Organizer
      ICSM2010
    • Place of Presentation
      京都国際会館
    • Year and Date
      2010-07-05
    • Related Report
      2012 Final Research Report
  • [Presentation] Synthesis of Thiophene-Fused Porphyrazines and Application to Solution-Processed Organic Field-Effect Transistors2010

    • Author(s)
      宮碕栄吾
    • Organizer
      ICSM2010
    • Place of Presentation
      京都:Kyoto International Conference Center
    • Year and Date
      2010-07-05
    • Related Report
      2010 Annual Research Report
  • [Presentation] Solution-Processable Phthalocyantine-based Semiconductor:Development of Thiophene-fused Porphyrazines and Application to Organic Thin-film Devices2010

    • Author(s)
      宮碕 栄吾
    • Organizer
      Fπ9
    • Place of Presentation
      Georgia Institute ofTechnology,アメリカジョージア州
    • Year and Date
      2010-05-27
    • Related Report
      2012 Final Research Report
  • [Presentation] Solution-Processable Phthalocyantine-based Semiconductor : Development of Thiophene-fused Porphyrazines and Application to Organic Thin-film Devices2010

    • Author(s)
      宮碕栄吾
    • Organizer
      Fπ9
    • Place of Presentation
      アトランタ:ジョージア工科大学(アメリカ)
    • Year and Date
      2010-05-27
    • Related Report
      2010 Annual Research Report

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

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