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2007 Fiscal Year Final Research Report Summary

ドナーーアクセプター型分極分子に基づく単一成分導体および特異な導電体の開発

Research Project

Project/Area Number 15073212
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionTokyo Institute of Technology

Principal Investigator

山下 敬郎  Tokyo Institute of Technology, 大学院・総合理工学研究科, 教授 (90116872)

Co-Investigator(Kenkyū-buntansha) 西田 純一  東京工業大学, 助教 (70334521)
Project Period (FY) 2003 – 2007
Keywords有機半導体 / 有機トランジスタ / 分子性結晶 / 機能材料 / 有機エレクトロニクス / 合成化学
Research Abstract

ヘテロ環オリゴマーの末端にトリフルオロメチルフェニル基を導入して高性能のn-型のFETを開発した。中心のπ電子コアにチアゾロチアゾール誘導体、およびビチアゾール誘導体を用いて、高い移動度を実現した。コアとしてターチオフェンおよびその類縁体を用いた化合物も高性能を示した。ターチオフェンは電子供与性であるために、電子受容性は低いが、高移動度(0.37cm^2/Vs)を示し、閾値45Vもチアゾール系よりも低下した。これは分子間の相互作用が大きく、電極と半導体のコンタクトも良いためと考えられる。電子受容性を高めるためにピラジン環を縮環した化合物の移動度は0.22cm^2/Vsであり、閾値は20Vとさらに低下した。これらのチオフェン環をセレノフェン環に置換した化合物についても合成した。セレン原子の導入で分子間の相互作用が強まり、若干の性能向上が見られた。さらに新規なn-型半導体としてインデノフルオレンジオン誘導体およびピラジン類縁体を合成した。インデノフルオレンジオン誘導体のトップコンタクトのFETデバイスは移動度0.16cm^2/Vsであったが、閾値は75Vと高い値を示した。ピラジン環を導入することで電子受容性が大きくなり、閾値は大幅に低下した。また、TTF系において多環芳香族環を縮合させることで、系の安定化と分子間π-π相互作用を強くすることが出来た。例えば、ナフタレン縮合化合物はホール移動度0.42cm^2/Vsを示したが、酸素に対して不安定であった。一方、キノキサリン誘導体は電子受容性のキノキサリン環と電子供与性のTTF骨格との分子間電荷移動相互作用でπ-スタック構造を取っており、そのFETのホール移動度は0.20cm^2/Vsであった。フッ素などの電子受容基を導入することでTTFとして初めてn型特性を実現した。

  • Research Products

    (43 results)

All 2007 2006 2005 2004 2003

All Journal Article (43 results) (of which Peer Reviewed: 43 results)

  • [Journal Article] n-Type Organic Field-Effect Transistors with High Electron Mobilities Based on Thiazole-thiazolothiazole Conjugated Molecules2007

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

      Mater. Chem. 19

      Pages: 5404-5409

    • Peer Reviewed
  • [Journal Article] Photooxidation and Reproduction of Pentacene Derivatives Substituted by Aromatic Groups2007

    • Author(s)
      K. Ono, H. Totani, T. Hiei, A. Yoshino, K. Saito, K. Eguchi, M. Tomura, J. Nishida, Y. Yamashita
    • Journal Title

      Tetrahedron 63

      Pages: 9699-9704

    • Peer Reviewed
  • [Journal Article] High-performance n-Type Organic Field-effect Transistors Based on Co-oligomers Containing a Trifluoromethylphenylthiazolyl Group and a Biphenylene Core2007

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

      Chem. Lett. 36

      Pages: 1198-1199

    • Peer Reviewed
  • [Journal Article] Organic Field-Effect Transistors Based on Asymmetrical Tetrathiafulvalene Analogues2007

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

      Asia. Chem. Lett. 11

      Pages: 179-184

    • Peer Reviewed
  • [Journal Article] Synthesis, Physical Properties and Field-Effect Transistors of Novel Thiazolothiazole/Phenylene Co-Oligomers2007

    • Author(s)
      S. Ando, D. Kumaki, J. Nishida, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita
    • Journal Title

      J. Mater. Chem 17

      Pages: 553-558

    • Peer Reviewed
  • [Journal Article] Synthesis, Characterization and Electroluminescence Properties of New Iridium Complexes Based on Cyclic Phenylvinylpyridine Derivatives : Tuning of Emission Colour and Efficiency by Structural Contorl2007

    • Author(s)
      S. Takizawa, Y. Sasaki, M. Akhtaruzzaman, H. Echizen, J. Nishida, T. Iwata, S. Tokito, Y. Yamashita
    • Journal Title

      J. Mater. Chem 17

      Pages: 841-849

    • Peer Reviewed
  • [Journal Article] Organic Field-Effect Transistors Based on Heterocyclic Co-Oligomers Containing a Pyrazine Ring2007

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

      Chem. Commun

      Pages: 1430-1432

    • Peer Reviewed
  • [Journal Article] High-Performance and Light-Emitting n-Type Organic Field-Effect Transistors Based on Dithienylbenzothiadiazole and Related Heterocycles2007

    • Author(s)
      T. Kono, D. Kumaki, J. Nishida, T. Sakanoue, M. Kakita, H. Tada, S. Tokito, Y. Yamashita
    • Journal Title

      Chem. Mater 19

      Pages: 1218-1220

    • Peer Reviewed
  • [Journal Article] Significant Improvement of Electron Mobility in Organic Thin-Film Transistors Based on Thiazolothiazole Derivatives by Employing Self-Assembled Monolayer2007

    • Author(s)
      D. Kumaki, S. Ando, S. Shimono, Y. Yamashita, T. Umeda, S. Tokito
    • Journal Title

      Appl. Phys. Lett. 90

      Pages: 053506

    • Peer Reviewed
  • [Journal Article] Phosphorescent Iridium Complexes Based on 2-Phenylimidazo[1, 2-a]pyridine Ligands : Tuning of Emission Color Toward the Blue Region, and Application to Polymer Light-Emitting Devices2007

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

      Inorg. Chem 46

      Pages: 4308-4319

    • Peer Reviewed
  • [Journal Article] n-Type and Ambipolar FET Characteristics Using Pyrazinophenanthrolines Linked with Oligothiophenes2006

    • Author(s)
      J. Nishida, S. Murakami, H. Tada, Y. Yamashita
    • Journal Title

      Chem. Lett. 35

      Pages: 1236-1237

    • Peer Reviewed
  • [Journal Article] High Performance n- and p-Type Field-Effect Transistors Based on Tetrathiafulvalene Derivatives2006

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

      J. Am. Chem. Soc 128

      Pages: 9898-9599

    • Peer Reviewed
  • [Journal Article] Phosphorescence Color Tunable Iridium Complexes with Ligands of 2-Phenyimidazo[1, 2-a]pyridine Derivatives2006

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

      Mol. Cryst. Liq. Cryst. 455

      Pages: 381-385

    • Peer Reviewed
  • [Journal Article] Finely Tuned Blue Phosphorescent Iridium Complexes Based on 2-Phenypyridine Derivatives and Application to Polymer Organic Light-emitting Device2006

    • Author(s)
      S. Takizawa, H. Echizen, J. Nishida, T. Tsuzuki, S. Tokito, Y. Yamashita
    • Journal Title

      Chem. Lett. 35

      Pages: 748-749

    • Peer Reviewed
  • [Journal Article] Physical properties and field-effect transistors based on novel thiazolothiazole/heterocyclic and thiazolothiazole/phenylene co-oligomers2006

    • Author(s)
      S. Ando, J. Nishida, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita
    • Journal Title

      Synth. Met. 156

      Pages: 327-331

    • Peer Reviewed
  • [Journal Article] n-Type Organic Field-Effect Transistors with Very High Electron Mobilities Based on Thiazole Oligomers with Trifluoromethylphenyl Groups2005

    • Author(s)
      S. Ando, R. Murakami, J. Nishida, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 14996-14997

    • Peer Reviewed
  • [Journal Article] Preparation and Electroluminescent Characteristics of a Series of Electron Rich Cyclometalated Phenylpyridine Ir(III) Complexes with a Diphenylamino Group2005

    • Author(s)
      J. Nishida, H. Echizen, H. Iwata, Y. Yamashita
    • Journal Title

      Chem. Lett. 34

      Pages: 1378-1379

    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Novel Iridium Complexes with Ligands of 2-Phenylimidazo[1, 2-a]pyridine Derivatives, and Application to Organic Light-Emitting Diode2005

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

      Chem. Lett 34

      Pages: 1222-1223

    • Peer Reviewed
  • [Journal Article] High Performance Organic Field-Effect Transistors Based on π-Extended Tetrathiafulvalene Derivatives2005

    • Author(s)
      Naraso, J. Nishida, S. Ando, J. Yamaguchi, K. Itaka, H. Koinuma, H. Tada, S. Tokito, Y. Yamashita
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 10142-10143

    • Peer Reviewed
  • [Journal Article] Synthesis, Characterization and FET Properties of Novel Dithazolylbenzothiadiazole Derivatives2005

    • Author(s)
      M. Akhtaruzzaman, N. Kamata, J. Nishida, S. Ando, H. Tada, M. Tomura, Y. Yamashita
    • Journal Title

      Chem. Commun.

      Pages: 3183-3185

    • Peer Reviewed
  • [Journal Article] TTF Derivatives Containing Fused-Pyrazine Rings for Novel Donor-Acceptor Systems2005

    • Author(s)
      Naraso, J. Nishida, M. Tomura, Y. Yamashita
    • Journal Title

      Synth. Met. 153

      Pages: 389-392

    • Peer Reviewed
  • [Journal Article] Novel TTF Vinylogues Containing Phenyl Groups at the Vinyl Positions2005

    • Author(s)
      M. Osada, T. Kumagai, M. Sugimoto, J. Nishida, Y. Yamashita
    • Journal Title

      Synth. Met. 152

      Pages: 429-432

    • Peer Reviewed
  • [Journal Article] High Performance n-Type Organic Field-Effect Transistors Based on π-Electronic Systems with Trifluoromethylphenyl Groups2005

    • Author(s)
      S. Ando, J. Nishida, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita
    • Journal Title

      J. Am. Chem. Soc. 127

      Pages: 5336-5337

    • Peer Reviewed
  • [Journal Article] Preparation, Characterization and Electroluminescence Characteristics of α-Diimine-type Platinum(II) Complexes with Perfluorinated Phenyl Groups as Ligands2005

    • Author(s)
      J. Nishida, A. Maruyama, T. Iwata, Y. Yamashita
    • Journal Title

      Chem. Lett. 34

      Pages: 592-593

    • Peer Reviewed
  • [Journal Article] Novel p-and n-Type Organic Semiconductors with an Anthracene Unit2005

    • Author(s)
      S. Ando, J. Nishida, E. Fujiwara, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita
    • Journal Title

      Chem. Mater. 17

      Pages: 1261-1264

    • Peer Reviewed
  • [Journal Article] Field-Effect Transistors Based on Single Crystalline Wires of Bis(l, 2, 5-thiadiazolo)-p-quinobis(1, 3-dithiole)2005

    • Author(s)
      E. Fujiwara, M. Takada, Y. Yamashita, H. Tada
    • Journal Title

      Jpn. J. Applied. Phys. 44

      Pages: L82-L84

    • Peer Reviewed
  • [Journal Article] Novel Field-Effect Transistors Based on Bis(1, 3-dithiol-2-ylidene) Compounds with a Conjugated Spacer Group2004

    • Author(s)
      Y. Morioka, J. Nishida, E. Fujiwara, H. Tada, Y. Yamashita
    • Journal Title

      Chem. Lett. 33

      Pages: 1632-1633

    • Peer Reviewed
  • [Journal Article] Characterization and Field-Effect Transistor Performance of Heterocyclic Oligomers Containing a Thiazolothiazole Unit2004

    • Author(s)
      S. Ando, J. Nishida, ^+ E. Fujiwara, H. Tada, Y. Inoue, S. Tokito, Y. Yamashita
    • Journal Title

      Chem. Lett. 33

      Pages: 1170-1171

    • Peer Reviewed
  • [Journal Article] Novel Donor-π-Acceptor Compounds Containing 1, 3-Dithiol-2-ylidene and Tetracyanobutadiene units2004

    • Author(s)
      Y. Morioka, N. Yoshizawa, J. Nishida, Y. Yamashita
    • Journal Title

      Chem. Lett. 33

      Pages: 1190-1191

    • Peer Reviewed
  • [Journal Article] Novel Thiophene Oligomers Containing a Redox Active Hexaarylethane Unit2004

    • Author(s)
      J. Nishida, T. Miyagawa, Y. Yamashita
    • Journal Title

      Org. Lett. 6

      Pages: 2523-2526

    • Peer Reviewed
  • [Journal Article] Preparation, Characterization and FET Properties of Novel Dicyanopyrazinoquinoxaline Derivatives2004

    • Author(s)
      J. Nishida, Naraso, S. Murai, E. Fujiwara, H. Tada, M. Tomura, Y. Yamashita
    • Journal Title

      Org. Lett 6

      Pages: 2007-2010

    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Novel Dipyridylbenzothiadiazole and Bisbenzothiadiazole Derivatives2004

    • Author(s)
      M. Akhtaruzzaman, M. Tomura, J. Nishida, Y. Yamashita
    • Journal Title

      J. Org. Chem. 69

      Pages: 2953-2958

    • Peer Reviewed
  • [Journal Article] Synthesis, Physical Properties, and Field-Effect Transistors of Novel Thiophene/Thiazolothiazole Co-Oligomers2004

    • Author(s)
      S. Ando, J. Nishida, Y. Inoue, S. Tokito, Y, Yamashita
    • Journal Title

      J. Mater. Chem. 14

      Pages: 1787-1790

    • Peer Reviewed
  • [Journal Article] Pyrazino-tetracyanonaphthoquinodimethanes : Sterically Deformed Electron Acceptors Affording Zwitterionic Radicals2004

    • Author(s)
      T. Suzuki, S. Miyanari, H. Kawai, K. Fujiwara, T. Fukushima, T. Miyashi, Y. Yamashita
    • Journal Title

      Tetrahedron 60

      Pages: 1997-2003

    • Peer Reviewed
  • [Journal Article] Combined Spectroscopic and Theoretical Study of Narrow-Bandgap Heterocyclic Cooligomers Containing Alternating Aromatic-Donor and o-Quinonoid-Acceptor Units2004

    • Author(s)
      M. C. R. Delgado, V. Hernandez, J. T. L. Navarrete, S. Tanaka, Y. Yamashita
    • Journal Title

      J. Phys. Chem. B 108

      Pages: 2516-2526

    • Peer Reviewed
  • [Journal Article] 4, 5-Diiodo[1, 2, 5]thiadiazolotetrathiafulvalene2004

    • Author(s)
      M. Tomura, Y. Yamashita
    • Journal Title

      Acta Cryst. Sect. E 60

      Pages: o63-o65

    • Peer Reviewed
  • [Journal Article] Crystal Structure of 4, 7-Dibromo-2, 1, 3-benzothiadiazole, C6H2Br2N2S2003

    • Author(s)
      M. Tomura, Y. Yamashita
    • Journal Title

      Z. Kristallogr. NCS 218

      Pages: 555-556

    • Peer Reviewed
  • [Journal Article] (1, 3-Dithio-2-ylidene)propanedinitrile2003

    • Author(s)
      M. Tomura, Y. Yamashita
    • Journal Title

      Acta Cryst. Sect. E 59

      Pages: o1941-o1943

    • Peer Reviewed
  • [Journal Article] Preparation, Structure and Properties of Novel 1, 3-Dithiole-2-ylidene Derivatives Containing Bis(ethynylpyridine) Units2003

    • Author(s)
      T. Kumagai, M. Tomura, J. Nishida, Y. Yamashita
    • Journal Title

      Tetrahedron Lett. 44

      Pages: 6845-6848

    • Peer Reviewed
  • [Journal Article] Unusual Hydrogen Bonding Networks Consisted of π-Extended 4, 4'-Bipyridines and Chloranilic Acid2003

    • Author(s)
      M. Akhtaruzzaman, M. Tomura, K. Takahashi, J. Nishida, Y. Yamashita
    • Journal Title

      Supramolecular Chemistry 15

      Pages: 239-243

    • Peer Reviewed
  • [Journal Article] Linear Molecules with Ethynylpyridine and Bisbenzothiadiazole Units2003

    • Author(s)
      M. Akhtaruzzaman, M. Tomura, J. Nishida, Y. Yamashita
    • Journal Title

      Synth. Met. 137

      Pages: 873-874

    • Peer Reviewed
  • [Journal Article] Novel Electron Acceptors Containing Thiadiazole and Thiophene Units2003

    • Author(s)
      Y. Yamashita, K. Suzuki, M. Tomura
    • Journal Title

      Synth. Met. 133

      Pages: 341-343

    • Peer Reviewed
  • [Journal Article] Unsymmetrical Tetrathiafulvalene with a Fused 1, 2, 5-Thiadiazole Ring and an Ethylenedioxy Group2003

    • Author(s)
      M. Tomura, Y. Yamashita
    • Journal Title

      Acta Cryst. Sect. E 59

      Pages: o145-o147

    • Peer Reviewed

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Published: 2010-06-09   Modified: 2016-04-21  

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