Development of photochemical synthesis of organic semiconducting aromatic compounds

2008 Fiscal Year Final Research Report

• Project/Area Number: 18550037
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Ehime University
• Principal Investigator: YAMADA Hiroko Ehime University, 大学院・理工学研究科, 准教授 (20372724)
• Project Period (FY): 2006 – 2008
• Keywords: 有機半導体 / 光反応 / アセン / ジケトン

Research Abstract

近年, ロールトゥロールやスクリーン法などの溶液プロセスにより有機半導体デバイスを作成することが求められている. 我々は顔料系の低分子有機半導体を溶液塗布するための, 光変換型前駆体を開発し, その光反応メカニズムや導電特性の詳細について検討した. ペンタセンでは, ジケトン前駆体の溶液塗布と光変換により作成したp型OFET で0. 34cm^2/Vs の電荷移動度を達成し, またポルフィリンジケトン前駆体の光変換にも成功した.

Research Products

• [Journal Article] Organic Thin-Film Transistor from a Pentacene Photo Precursor (2009)
  • Author(s): A. Masumoto ; Y. Yamashita ; S. Go ; T. Kikuchi ; H. Yamada ; T. Okujima ; N. Ono, *H. Uno
  • Journal Title: Jpn J. Appl. Phys. 48 Pages: 051505/1-5
• [Journal Article] Synthesis, Structures and Optical and Electrochemical Properties of Benzoporphycenes (2009)
  • Author(s): D. Kuzuhara, J. Mack, H. Yamada, T. Okujima, N. Ono, N. Kobayashi
  • Journal Title: Eur. J. Chem. (in press)
• [Journal Article] Synthesis of 2, 3-dihydrobenzo[1, 4]dithiin-fused porphyrins, Phosphorus (2009)
  • Author(s): G. Jin, ; T. Okujima ; Y. Hashimoto ; H. Yamada ; H. Uno ; N. Ono
  • Journal Title: Sulfur Silicon Relat. Elem (in press)
• [Journal Article] Synthesis of mono-, di-and tribenzoporphyrins from their soluble precursors (2009)
  • Author(s): T. Okujima ; Y. Hashimoto ; G. Jin ; H. Yamada ; N. Ono
  • Journal Title: Heterocycles 77 Pages: 1235-1248
• [Journal Article] Absorption and Emission Properties of Acenaphthoporphyrins (2009)
  • Author(s): J. Nakamura, N. Ono, H. Yamada, T. Okujima
  • Journal Title: Mol. Cryst. Liq. Cryst. 505 Pages: 349-355
• [Journal Article] 1-Aminoisoindoleasauseful -systemelongationunit (2009)
  • Author(s): T. Akiyama, H. Uoyama, T. Okujima, H. Yamada, N. Ono, H. Uno
  • Journal Title: Tetrahedron 65 Pages: 4345-4350
• [Journal Article] A Facile One Pot Synthesis of meso-Aryl-Substituted[14]Triphyrin(2.1.1) (2008)
  • Author(s): Z. -L. Xue, Z. Shen, J. Mack, D. Kuzuhara ; H. Yamada, T. Okuzima, N. Ono, X. -Z. You, N. Kobayashi
  • Journal Title: J. Am. Chem. Soc. 130 Pages: 16478-16479
• [Journal Article] Organic semiconductors based on small molecules with thermally or photochemically removable groups (Review) (2008)
  • Author(s): H. Yamada, T. Okujima, and N. Ono
  • Journal Title: Chem. Commun Pages: 2957-2974
• [Journal Article] Synthesis and Characterization of Tetraanthroporphyrins (2008)
  • Author(s): H. Yamada, D. Kuzuhara, T. Takahashi, Y. Shimizu, K. Uota, T. Okujima, H. Uno
  • Journal Title: N. Ono Org. Lett 10 Pages: 2947-2950
• [Journal Article] Selective synthesis of 5-alkenyl-15-alkynyl-porphyrin and 5, 15-dialkynyl-porphyrin by 2+2 acid-catalyzed condensation of dipyrrylmethane and TMS propynal (2008)
  • Author(s): H. Yamada, K. Kushibe, S. Mitsuogi, T. Okujima, H. Uno, N. Ono
  • Journal Title: Tetrahedron Lett 49 Pages: 4731-4733
• [Journal Article] Soluble precursors of 2, 3-naphthalocyanine and phthalocyanine for use in thin film transistors (2008)
  • Author(s): A. Hirao, T. Akiyama, T. Okujima, H. Yamada, H. Uno, Y. Sakai, S. Aramaki, N. Ono
  • Journal Title: Chem. Commun Pages: 4714-4716
• [Journal Article] Synthesis of extremely soluble precursors of tetrabenzoporphyrins (2008)
  • Author(s): T. Okujima, Y. Hashimoto, G. Jin, H. Yamada, H. Uno, and N. Ono
  • Journal Title: Tetrahedron 64 Pages: 2405-2411
• [Journal Article] Photocurrent generation of benzoporphyrin films prepared by solution process (2007)
  • Author(s): H. Yamada, N. Kamio, A. Ohishi, M. Kawano, T. Okujima, N. Ono
  • Journal Title: J. Porphyrins Phthalocyanines 11 Pages: 383-389
• [Journal Article] Polycrystalline tetrabenzoporphyrin organic field-effect transistors with nanostructuired channels (2007)
  • Author(s): P. B. Shea, C. Chen, J. Kanicki, L. R. Pattison, P. Petroff, H. Yamada, N. Ono
  • Journal Title: Appl. Phys. Lett 157 Pages: 190-197
• [Journal Article] Solution-processed polycrystalline copper tetrabenzoporphyrins thin-film transistors (2007)
  • Author(s): P. B. Shea, L.R. Pattison, M. Kawano, C. Chen, J. Chen, P. Petroff, D. C. Martin, H. Yamada, N. Ono, J. Kanicki
  • Journal Title: Synth. Metals 157 Pages: 190-197
• [Journal Article] Synthesis of phthalocyanine fused with bicycle[2. 2. 2]octadienes and thermal conversion into naphthalocyanine (2007)
  • Author(s): T. Akiyama, A. Hirao, T. Okujima, H. Yamada, H. Uno, and N. Ono
  • Journal Title: Heterocycles 74 Pages: 835-843
• [Journal Article] Effective photochemical synthesis of an air-stable anthracene-based organic semiconductor from its diketone precursor (2006)
  • Author(s): H. Yamada, E. Kawamura, S. Sakamoto, Y. Yamashita, T. Okujima, H. Uno, N. Ono
  • Journal Title: Tetrahedron Lett 47 Pages: 7501-7504
• [Journal Article] Novel one-pot synthesis of 5-alkenyl-15-alkynylporphyrins and their derivatisation to a butadiyne-linked benzoporphyrin dimer (2006)
  • Author(s): H. Yamada, K. Kushibe, T. Okujima, H. Uno, and N. Ono
  • Journal Title: Chem. Commun Pages: 383-385
• [Journal Article] A New Synthesis of Tetra(quinoxalino)tetraazaporphyrin by retro Diels-Alder Reaction of a Soluble Precursor (2006)
  • Author(s): T. Okujima, M. Kikuchi, H. Yamada, H. Uno, N. Ono
  • Journal Title: J. Porphyrins Phthalocyanines 10 Pages: 1197-1201
• [Journal Article] Solution-processed nickel tetrabenzo porphyrin thin-film transistors (2006)
  • Author(s): P. B. Shea, *J. Kanicki, L.R. Pattison, P. Petroff ; M. Kawano, H. Yamada, N. Ono
  • Journal Title: J. Appl. Phys. 100 Pages: 034502 0-7
• [Journal Article] Synthesis of 4, 7-Dihydro-2H-isoindole Derivatives via Diels-Alder Reaction of Tosylacetylene (2006)
  • Author(s): T. Okujima, G. Jin, Y. Hashimoto, H. Yamada, H. Uno, N. Ono
  • Journal Title: Heterocycles 70 Pages: 619-626
• [Presentation] ジケトンポルフィリンの合成と光物性の研究 (2009)
  • Author(s): 山田容子・村岸優・葛原大軌・宇野英満・小野昇
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 船橋市, 日本大学
  • Year and Date: 20090327-30
• [Presentation] ノナセンの合成研究 (2009)
  • Author(s): 勝田修平・山田容子
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 船橋市, 日本大学
  • Year and Date: 20090327-30
• [Presentation] 有機低分子半導体の光による高効率合成とデバイスへの応用 (2009)
  • Author(s): 山田容子
  • Organizer: SORSTシンポジウム(2)フレクシブルデバイス/マテリアルの未来像
  • Place of Presentation: 東京, コクヨホール
  • Year and Date: 20090212-13
• [Presentation] 塗布型低分子半導体の開発とエレクトロニクスへの応用 (2009)
  • Author(s): 山田容子 ; 小野昇
  • Organizer: 2009年電子情報通信学会大会
  • Place of Presentation: 松山市, 愛媛大学
  • Year and Date: 2009-03-19
• [Presentation] ピレン連結アントラセンのαジケトン前駆体の合成と物性 (2008)
  • Author(s): 谷本泰志・山田容子・小野昇
  • Organizer: 日本化学会第88回春季年会
  • Place of Presentation: 東京都, 立教大学
  • Year and Date: 20080326-30
• [Presentation] アルキル鎖を持つチオフェンを導入したアントラセン可溶性前駆体の合成と物性 (2008)
  • Author(s): 河野裕郎・山田容子・小野昇
  • Organizer: 日本化学会第88回春季年会
  • Place of Presentation: 東京都, 立教大学
  • Year and Date: 20080326-30
• [Presentation] 有機半導体の光による高効率合成とデバイスへの応用 (2008)
  • Author(s): 山田容子
  • Organizer: 第4回SORST横断デバイス物性研究会
  • Place of Presentation: 吹田市, 阪大
  • Year and Date: 2008-10-01
• [Presentation] 光反応を利用した有機半導体の高効率合成と物性 (2008)
  • Author(s): 山田容子
  • Organizer: 若手化学者のための化学道場
  • Place of Presentation: 徳島市, 眉山かんぽの宿
  • Year and Date: 2008-09-11
• [Presentation] Highly effective photochemical synthesis of organic semiconductors (2007)
  • Author(s): Hiroko Yamada ; Yuko Yamashita ; Noboru Ono
  • Organizer: 2007Korea-Japan Symposium on Frontier Photoscience
  • Place of Presentation: 韓国慶州
  • Year and Date: 20071122-25
• [Presentation] Photochemical Synthesis of Organic Semiconductors Hiroko Yamada (2007)
  • Author(s): 2th International Symposium on Integrated Molecular and Macromolecular Materials
  • Place of Presentation: 北京
  • Year and Date: 20071025-28
• [Presentation] Photochemical synthesis of acene compounds for organic electronics from diketone precursors (2007)
  • Author(s): Hiroko Yamada, Yuko Yamashita, Hiroo Kawano, Noboru Ono
  • Organizer: XXIII International Conference on Photochemisty
  • Place of Presentation: ケルン市, ドイツ
  • Year and Date: 20070729-0803
• [Presentation] Synthesis and photochemistry of diketone precursor of tetracene (2007)
  • Author(s): Yuko Yamashita, Hiroko Yamada, Noboru Ono
  • Organizer: XXIII International Conference on Photochemisty
  • Place of Presentation: ケルン市, ドイツ
  • Year and Date: 20070729-0803
• [Presentation] ポルフィリン連結アントラセンのαジケトン前駆体の合成と物性 (2007)
  • Author(s): 谷本泰志、高橋哲郎、山田容子、小野昇
  • Organizer: 第87回日本化学会春季年会
  • Place of Presentation: 吹田市, 関西大学
  • Year and Date: 20070325-28
• [Presentation] Photochemical synthesis of semiconducting acene compounds from diketone precursors Hiroko Yamada (2007)
  • Author(s): Yuko Yakmashita, Hiroo Kawano, Tetsuo Okujima, Hidemitsu Uno, Noboru Ono
  • Organizer: 国際有機電子移動化学シンポジウム
  • Place of Presentation: 神奈川・慶応大学
  • Year and Date: 20070107-10
• [Presentation] ペンタセンの光化学及び電気化学的合成 (2006)
  • Author(s): 山田容子, 山下裕子, 小野昇, 大久保敬, 福住俊一
  • Organizer: 電気化学会秋季大会
  • Place of Presentation: 同志社大学田辺キャンパス
  • Year and Date: 20060914-15
• [Presentation] Photochemical Synthesis of Pentacene and Anthracene Derivatives (2006)
  • Author(s): Hiroko Yamada, ^1 Yuko Yamashita, 1 Emi Kawamura, ^1 Sadaaki Sakamoto, ^1 Hidemitsu Uno, ^2 and Noboru Ono
  • Organizer: The Seventh Symposium on Functional π Electron System
  • Place of Presentation: 大阪市 Grand Cube Osaka
  • Year and Date: 20060515-20
• [Presentation] Photochemical Synthesis of Pentacene and its Derivatives (2006)
  • Author(s): Hiroko Yamada, Yuko Yamashita, Sadaaki Sakamoto, Hidemitsu Uno, and Noboru Ono
  • Organizer: XXIst IUPAC Symposium on Photochemistry
  • Place of Presentation: 京都市、京都テルサ
  • Year and Date: 20060402-07
• [Book] 低分子有機半導体材料の開発,『有機薄膜太陽電池の高効率化と耐久性向上』(分担執筆) (2009)
  • Author(s): 山田容子, 小野昇
  • Total Pages: 123-159
  • Publisher: サイエンス&テクノロジー株式会社
• [Book] 変換型半導体材料の開発とその応用『低分子有機半導体の高性能化(仮題)』(分担執筆) (2009)
  • Author(s): 山田容子, 小野昇, 荒牧晋司
  • Publisher: サイエンス&テクノロジー株式会社(In Press)
• [Book] Supramolecules Based on Porphyrins Top Heterocycl Chem(分担執筆) (2008)
  • Author(s): H. Yamada, T. Okujima, N. Ono
  • Total Pages: 123-159
  • Publisher: Springer-Verlag
• [Remarks] 前駆体を利用した溶液塗布型有機低分子半導体の開発 山田容子 化学工業 2009, 60, 4, 306-311.
• [Remarks] 可溶性前駆体の光反応による有機半導体の高効率合成 山田容子 光化学協会誌 2008, 39, 3, 209-213.
• [Patent(Industrial Property Rights)] ポルフィセン及びその製造法, フィルム, 半導体材料, 蛍光色素並びに太陽電池 (2008)
  • Inventor(s): 山田容子 ; 奥島鉄雄 ; 小野昇 ; 葛原大軌
  • Industrial Property Rights Holder: 三菱化学株式会社・国立大学法人愛媛大学
  • Industrial Property Number: 2008-245760
  • Filing Date: 2008-09-25
• [Patent(Industrial Property Rights)] 半導体素子の製造方法 (2007)
  • Inventor(s): 桝本茜, 菊池憲裕, 小野昇, 宇野英満, 中島容子
  • Industrial Property Rights Holder: キャノン株式会社, 国立大学法人愛媛大学
  • Industrial Property Number: 2007-232091
  • Filing Date: 2007-08-31
• [Patent(Industrial Property Rights)] 半導体素子の製造方法 (2006)
  • Inventor(s): 桝本茜, 小野昇, 宇野英満, 中島容子
  • Industrial Property Rights Holder: キャノン株式会社, 国立大学法人愛媛大学
  • Industrial Property Number: 2006-352555
  • Filing Date: 2006-12-27