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2012 Fiscal Year Final Research Report

Synthesis of Cyclic Oligomers by the Dynamic Covalent Chemistry Mechanism and their Application for Resist Materials

Research Project

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Project/Area Number 22350088
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic industrial materials
Research InstitutionKansai University (2012)
Kanagawa University (2010-2011)

Principal Investigator

KUDO Hiroto  関西大学, 化学生命工学部, 准教授 (30343635)

Project Period (FY) 2010 – 2012
Keywordsレジスト
Research Abstract

A new dynamic covalent chemistry (DCC) system in the reaction of resorcinol and 1,5-pentanedial could be achieved, yielding a only soluble oligomer noria (noria means water wheel in Latin) in high yield, resembling a water-wheel in appearance. Application of the noria derivatives with pendant photo-reactive groups were examined for UV-curing materials and photo-resist materials. The obtained noria derivatives had good solubility, good film-forming ability, high thermal stability, and high photo-chemical reactivity. Furthermore, certain new ladder cyclic oligomers could be synthesized using a similar approach to that employed for the synthesis of noria and their application as next generation resist materials was also investigated

  • Research Products

    (32 results)

All 2013 2012 2011 2010 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results) Presentation (18 results) Remarks (1 results)

  • [Journal Article] Synthesis and Property of Noria (Water-Wheel Like Macrocycle) Derivatives with Pendant Alkoxyl and Adamantyl Ester Groups, and Their Application for Extreme Ultraviolet (EUV) Resist2013

    • Author(s)
      Nobumitsu Niina, Hiroto Kudo, Hiroaki Oizumi, Toshiro Itani, and Tadatomi Nishikubo
    • Journal Title

      Thin Solid Films

      Volume: 534 Pages: 459-464

    • Peer Reviewed
  • [Journal Article] 動的共有結合化学システムによるラダー型環状オリゴマーの合成とそれらを基盤とした光機能性材料2012

    • Author(s)
      工藤 宏人、西久保忠臣
    • Journal Title

      有機合成化学協会誌5月号(総合論文)

      Volume: 70 Pages: 492-507

    • Peer Reviewed
  • [Journal Article] Impregnation of waterwheel supramolecules as proton carriers in Nafion-perfluorinated ionomer membranes2012

    • Author(s)
      Nadzrinahamin. A. Nazir, Hiroto Kudo, Tadatomi Nishikubo, Thein Kyu
    • Journal Title

      J Mater Sci

      Volume: 47 Pages: 7269-7279

    • Peer Reviewed
  • [Journal Article] Synthesis of Triple-ringed[14]Arene via Dynamic Covalent Chemistry Mechanism in Condensation Reaction of Phenols with m-Benzenedicarboaldehyde2012

    • Author(s)
      Hiroyuki Seki, Shingo Kuwabara, Hiroto Kudo, and Tadatomi Nishikubo
    • Journal Title

      Chemistry Letters

      Volume: 41 Pages: 699-701

    • Peer Reviewed
  • [Journal Article] Extreme Ultraviolet (EUV)-Resist Material Based on Noria (Water Wheel-like Macrocycle) Derivatives with Pendant Alkoxyl and Adamantyl Ester Groups2012

    • Author(s)
      Hiroto Kudo, Nobumitsu Niina, Tomoharu Sato, Hiroaki Oizumi, Toshiro Itani, Takuro Miura, Takeo Watanabe, Hiroo Kinoshita
    • Journal Title

      J. Photopolym. Sci. Technol.

      Volume: 25 Pages: 587-592

    • Peer Reviewed
  • [Journal Article] Synthesis and Property of Tellurium-containing Polymers Obtained by SimpleCondensation Reaction of Tetrachlorotellurium and 1,3-Dimethoxybenzene2011

    • Author(s)
      Hiroto Kudo, Hideatsu Ishihara, and Masashi Tomita
    • Journal Title

      Chemistry Letters

      Volume: 40 Pages: 762-764

    • Peer Reviewed
  • [Journal Article] Condensation Reaction of Phenols with 1,5-Pentanedial for Synthesis of Noria-like Ladder-cyclic Oligomer by Dynamic Covalent Chemistry Mechanism2011

    • Author(s)
      Hiroyuki Seki, Shingo Kuwabara, Hiroto Kudo and Tadatomi Nishikubob
    • Journal Title

      Chemistry Letters

      Volume: 40 Pages: 464-466

    • Peer Reviewed
  • [Journal Article] Extreme Ultraviolet Resist Fabricated Using Water Wheel-Like Cyclic Oligomer with Pendant Adamantyl Ester Groups, Jpn2011

    • Author(s)
      Hiroyuki Seki, Hiroto Kudo, Hiroaki Oizumi, Toshiro Itani, and Tadatomi Nishikubo
    • Journal Title

      J. Appl. Phys

      Volume: 50 Pages: 121602-1 - 7

    • Peer Reviewed
  • [Journal Article] Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups2011

    • Author(s)
      Nobumitsu Niina, Hiroto Kudo, Ken Maruyama, Toshiyuki Kai,Tsutomu Shimokawa, Hiroaki Oizumi, Toshiro Itani, Tadatomi Nishikubo
    • Journal Title

      Polymer Journal

      Volume: 43 Pages: 407-413

    • Peer Reviewed
  • [Journal Article] Synthesis and Photo-Cross-Linking Reaction of Noria Derivatives Containing Photoreactive Groups2010

    • Author(s)
      Hiroto Kudo, Nobumitsu Niina, Rieko Hayashi, Ken Kojima, Tadatomi Nishikubo
    • Journal Title

      Macromolecules

      Volume: 43(10) Pages: 4822 - 4826

    • Peer Reviewed
  • [Journal Article] Negative-type extreme ultraviolet resist materials based on water-wheel-like cyclic oligomer (noria)2010

    • Author(s)
      Hiroyuki Seki, Yuki kato, Hiroto Kudo, Hiroaki oizumi, Toshiro Itani, Tadatomi Nishikubo
    • Journal Title

      Jpn. J. Appl.

      Volume: 49 Pages: 06GF06

    • Peer Reviewed
  • [Journal Article] Novel extreme ultraviolet (EUV)-resist material based on noria(water wheel-like cyclic oligomer)2010

    • Author(s)
      Hiroto Kudo, Yuji Suyama, Hiroaki Oizumi, Toshiro Itani, Tadatomi Nishikubo
    • Journal Title

      Journal of Materials Chemistry

      Volume: 20(21) Pages: 4445-4450

    • Peer Reviewed
  • [Journal Article] xtreme Ultraviolet (EUV)-Resist Materials of Noria (Water Wheel-Like Cyclic Oligomer) Derivatives containing Acetal Moieties2010

    • Author(s)
      Hiroto Kudo, Mayumi Jinguji, Tadatomi Nishikubo, Hiroaki Oizumi, Toshiro Itani
    • Journal Title

      J. Photopolym. Sci. Technol

      Volume: 23(5) Pages: 657 - 664

    • Peer Reviewed
  • [Presentation] Novel Molecular Resist Materials based on Cyclic Oligomers2013

    • Author(s)
      Hiroto Kudo
    • Organizer
      2nd International EUV Resist Synmpojium
    • Place of Presentation
      大阪大学中之島センター(大阪)
    • Year and Date
      20130213-20130214
  • [Presentation] Extreme Ultraviolet (EUV)-Resist Material Based on Noria (Water Wheel-like Macrocycle) Derivatives2012

    • Author(s)
      Hiroto Kudo
    • Organizer
      International Advanced Nanopatterning Materials and Processes Workshop
    • Place of Presentation
      早稲田国際会議場(東京)
    • Year and Date
      20120703-20120704
  • [Presentation] Extreme Ultraviolet (EUV)-Resist Material Based on Noria (Water Wheel-like Macrocycle) Derivatives with Pendant Alkoxyl and Adamantyl Ester Groups2012

    • Author(s)
      Hiroto Kudo, Nobumitsu Niina, Tomoharu Sato, Hiroaki Oizumi, Toshiro Itani, Takuro Miura, Takeo Watanabe, Hiroo Kinoshita
    • Organizer
      The 29th International Conference of Photopolymer Science and Technology
    • Place of Presentation
      千葉大学コンベンションホール(千葉県)
    • Year and Date
      20120627-20120630
  • [Presentation] 動的共有結合による籠状分子の合成と光機能材料への応用2012

    • Author(s)
      工藤 宏人
    • Organizer
      高分子学会
    • Place of Presentation
      横浜国際会議場(神奈川県)
    • Year and Date
      20120530-20120531
  • [Presentation] 極端紫外線(EUVL)用分子レジスト材料の開発 (1Xnm以下の解像性をめざして)2012

    • Author(s)
      工藤 宏人
    • Organizer
      日本化学会 第92春季年会 (招待講演)
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2012-03-28
  • [Presentation] アセタール残基を有するNoria誘導体を基盤としたレジスト材料の開発2011

    • Author(s)
      神宮司真由美・工藤 宏人・西久保忠臣・老泉博昭・伊谷俊郎・丸山研・木村徹・下川努
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山大学
    • Year and Date
      2011-09-30
  • [Presentation] コアに空孔を有する構造が制御されたスターポリスチレンの合成2011

    • Author(s)
      木原宏介・工藤 宏人・西久保忠臣
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山大学
    • Year and Date
      2011-09-30
  • [Presentation] ビシクロオルソエステル残基を有するカリックスアレーン類の合成とそれらの屈折率変換特性2011

    • Author(s)
      清水達記、工藤 宏人、西久保忠臣
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山大学
    • Year and Date
      2011-09-30
  • [Presentation] オキセタニル基とカルボキシル基を有するアミノ酸誘導体類の合成と自己重付加反応、および得られたポリマー類の物理特性と生分解性2011

    • Author(s)
      大城利樹.・工藤 宏人・西久保忠臣
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山大学
    • Year and Date
      2011-09-29
  • [Presentation] 環状チオウレタン類を開始剤として用いた環拡大重合法による構造の制御された環状ポリマーの合成2011

    • Author(s)
      武士由希・島 茂記・工藤 宏人・西久保 忠臣
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山大学
    • Year and Date
      2011-09-29
  • [Presentation] Recent Development in Molecular Resists for Extreme Ultraviolet Lithography2011

    • Author(s)
      工藤 宏人・西久保忠臣
    • Organizer
      The 28th International Conference of Photopolymer Science and Technology (ICPST-28)
    • Place of Presentation
      千葉大学
    • Year and Date
      2011-06-22
  • [Presentation] Extreme Ultraviolet (EUV) . Resist Materials based on Water Wheel-like Cyclic Oligomer (Noria)2011

    • Author(s)
      工藤宏人・西久保忠臣
    • Organizer
      RadTech Asia 2011
    • Place of Presentation
      横浜国際会議場
    • Year and Date
      2011-06-21
  • [Presentation] アダマンチルエステル残基を有するカリックス[4]レゾルシンアレーントリマー(C7-trimer)誘導体の合成とそれらのEUVレジスト材料への応用2011

    • Author(s)
      石原 秀篤・森山 和樹・ 工藤 宏人・西久保 忠臣・老泉博昭・井谷 俊郎
    • Organizer
      第60回高分子学会年次大会
    • Place of Presentation
      大阪国際会議場
    • Year and Date
      2011-05-26
  • [Presentation] レゾルシノールと1,6-ヘキサンジア.ルの縮合反応によるラダ.型環状オリゴマーの合成とそれらの極端紫外線(EUV)レジスト材料への応用2011

    • Author(s)
      佐藤 友治・井谷 俊郎・老泉博昭・工藤 宏人・西久保 忠臣
    • Organizer
      60回高分子学会年次大会
    • Place of Presentation
      大阪国際会議場
    • Year and Date
      2011-05-26
  • [Presentation] ダマンチルアセタール残基を有するNoria誘導体の合成と、それらのEB、EUVレジスト特性2011

    • Author(s)
      神宮司 真由美・工藤 宏人・西久保 忠臣・老泉 南昭・井谷 俊郎・ 丸山 研・木村 徹・下川 努
    • Organizer
      第60回高分子学会年次大会
    • Place of Presentation
      大阪国際会議場
    • Year and Date
      2011-05-26
  • [Presentation] ビシクロオルソエステル残基を有するカリックスアレ-ン誘導.の合成と光反応およびそれらの屈折率上昇材2011

    • Author(s)
      清水 達記・工藤 宏人・西久保 忠臣
    • Organizer
      第60回高分子学会年次大会
    • Place of Presentation
      大阪国際会議場
    • Year and Date
      2011-05-25
  • [Presentation] 動的共有結合化学システムの構築による特殊構造分子の合成と応用(16 nm以下の高解像度レジスト材料の開発を目指して)2010

    • Author(s)
      工藤 宏人
    • Organizer
      関東高分子若手研究会
    • Place of Presentation
      横浜国立大学
    • Year and Date
      2010-11-20
  • [Presentation] Positive and Negative Type Extreme Ultraviolet (EUV) . Resist Materials based on Noria (Water Wheel-like Cyclic Oligomer)2010

    • Author(s)
      工藤 宏人
    • Organizer
      The 27th International Conference of Photopolymer Science and Technology Materials and Propcess for Advanced Microlithography and Nanotechnology
    • Place of Presentation
      千葉大学
    • Year and Date
      2010-06-23
  • [Remarks]

    • URL

      http://www2.kansai-u.ac.jp/kudo-lab/

URL: 

Published: 2014-08-29  

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