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Development of next-generation photosensitive organic insulating material wit low dielectric constant and low dissipation factor

Research Project

Project/Area Number 14350484
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionTokyo Institute of Technology

Principal Investigator

UEDA Mitsuru  Tokyo Institute of Technology, Organic & Polymeric Materials, Professor, 大学院・理工学研究科, 教授 (20007199)

Co-Investigator(Kenkyū-buntansha) SHIBASAKI Yuji  Tokyo Institute of Technology, Organic & Polymeric Materials, Assistant Professor, 大学院・理工学研究科, 助手 (90323790)
Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥14,500,000 (Direct Cost: ¥14,500,000)
Fiscal Year 2003: ¥5,200,000 (Direct Cost: ¥5,200,000)
Fiscal Year 2002: ¥9,300,000 (Direct Cost: ¥9,300,000)
Keywordsphotosensitive polymer / thermal stability / low dielectric constant / low dissipation factor / photosensitive poly(naphthylene) / photoacid generator / alkaline developable / 酸発生剤 / 感光性ポリ(フェニレンエーテル) / 感光性ポリベンズオキサゾール / アルカリ現象 / 全脂環式感光性ポリイミド
Research Abstract

1.A convenient synthesis of regiocontrolled poly(2,6-dihydroxy-1,5-naphthylene) (PDHN) with high molecular weights by oxidative coupling polymerization of 2,6-dihydroxynaphthalene has been developed. A negative working and chemically amplified photosensitive polymer based on PDHN, a cross-linker, and a photoacid generator PTMA has been developed. The resist showed a sensitivity of 8.3 mJ cm^<-2> and a contrast of 11. The optically estimated dielectric constant of the resist system in 2.88. A positive working and chemically amplified photosensitive polymer based on partially (30%) Ο-methylated poly(2,6-dihydroxy-1,5-naphthylene) [PMPDHN (30)], as an acidolytic de-cross-linker, and a photoacid generator PTMA has been developed. The resist showed a sensitivity of 19.4 mJ cm^<-2> and a contrast of 7.5. The optically estimated dielectric constants (at 1 MHz) of this resist 2.9. The moisture absorption (1.7 wt% this resist system based on PMPDHN (30) and TVEB is very low compared to that (4. … More 3%) of the resist system consisting of conventional PDHN resist system.
2.A chemically amplified photosensitive and thermosetting polymer based on poly[2,6-di(3-methyl-2-butenyl)phenol(15mol%)-co-2,6-dimethylphenol(85 mol%)] and a photoacid PTMA has been developed. The average refractive index of the cured copolymer film was 1.5452, from which the dielectric constant (ε) at 1 MHz was estimated as 2.6. The resist showed a sensitivity of 35 mJ cm^<-2> and a contrast of 1.6. The glass transition temperature of this polymer is 300℃ after thermal curing. Poly[(2-allyl-6-methyl-phenol(20mol%)-co-2,6-dimethylphenol(85 mol%)] after curing also showed low ε (2.6) and low dissipation factor 0.0015-0.0019 at 1 MHz.
3.A novel thermally stable and low dielectric poly(binaphthylene ether) has been developed. Polymer was easily prepared by oxidative coupling polymerization of 2,2'-bis(1-naphthyloxy)-1,1'-binaphthyl with FeCl_3 as an oxidant. The ε of polymer at 1 MHz was directly measured from the capacitance as 2.50. The modulus and hardness of polymer were determined as 9.8 GPa and 0.42 GPa. Less

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (50 results)

All Other

All Publications (50 results)

  • [Publications] T.Fukuhara, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of Thermosetting Poly(phenylene ether) containing Allyl Groups"Polymer. 45. 843-847 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Watanabe, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of Semiaromatic Polyimides from Aromatic Diamines Containing Adamantyl Units and Alicyclic Dianhydrides"J.Polym.Sci.Part-A Polym.Chem.. 41. 144-150 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Matsumoto, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of photosensitive and Thermosetting Poly(phenylene ether) Containing Allyl Groups"J.Polym.Sci.Part-A Polym.Chem.,. (Submitted).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tsuchiya, Y Shibasaki, M.Suzuki, M.Ueda: "Photosensitive Polymer Based on Poly(2,6-dihydroxy-1,5-naphthalene), a Cross-Linker, and a Photoacid Generator"J.Polym.Sci.Part-A Polym.Chem.,. 42. 2235-2240 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukukawa, Y Shibasaki, M.Ueda: "Photosensitive Poly(benzoxazole) via Poly(o-hydroxy azomethine) II : Environmentally Benign Process in Ethyl Lactate"Polym.J.. (In press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tsuchiya, Y Shibasaki, M.Suzuki, M.Ueda: "A Positive Type Alkaline Developable Thermally stable and Photosensitive Polymer Based on Partially O-Methylated Poly(2,6-dihydroxy-1,5-naphthylene), an acidolytic de-cross-linker, and a Photoacid Generator Submitted for publication in Polymer"Polymer. (submitted).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tsuchiya, H.Ishii, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of a Novel Poly(Biaphthalene ether)r with a Low Dielectric Constant."Macromolecules. (In press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tuchiya, Y Shibasaki, M.Suzuki, M.Ueda: "A New Negative-Type Photosensitive Polymer Based on Poly(2,6-dihydro-1,5-naphthylene), a Cross-Linker, and a Photoacid Generato"J.Photopolym.Sci & Technol.. 16. 285-286 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Ueda, K.Ebara, Y.Shibasaki: "New Convenient Synthetic Route for Photosensitive Poly(benzoxazole)"J.Photopolym.Sci & Technol. 16. 237-242 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Ebara, Y Shibasaki, M.Ueda: "Chemically Amplified Photosensitive Poly(benzoxazole)"J.Photopolym.Sci & Technol. 16. 287-292 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Morita, K.Ebara, Y.Shibasaki, K.Goto, S.Tami, M.Ueda: "New Positive-type Photosensitive Polyimide Having Sulfo Groups"Polymer. 44. 6235-6239 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "Photosensitive poly(benzoxazole) based on Precursor from Diphenyl Isophthalate and Bis(o-aminophenol)"Polymer. 44. 333-339 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Sasada, Y.Shibasaki, M.Suzuki, M.Ueda: "Convenient Synthesis of Poly(2,6-dihydroxy-1,5-naphthylene) by Cu(II)-amin Catalyzed Oxidative Coupling Polymerization"Polymer. 44. 355-360 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Sasada, Y.Shibasaki, M.Suzuki, M.Ueda: "New Positive-Type Photosensitive Polymer Based on Poly(2,6-dihydroxy-1,5-naphthylene) and Diazonaphtoquinone"J.Polym.Sci.Part-A Polym.Chem.. 40. 393-398 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Watanabe, Y.Sakai, Y.Shibasaki, S.Ando, M.Ueda, Y.Oishi, K.Mori: "Synthesis of Wholly Alicyclic Polyimides from N-Silylated Alicyclic Diamines and Alicyclic Dianhydrides"Macromolecules. 35. 2277-2281 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Watanabe, Y.Shibasaki, S.Ando, M.Ueda: "New Positive-Type Photosensitive Alkaline-Developable Alicyclic Polyimide Based on Poly(amic acid silylester) as a Polyimide Precursor and Diazonaphthoquinone as a Photosensitive Compound"Chem.Mater.. 14. 1762-1766 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Ebara, Y Shibasaki, M.Ueda: "New Synthetic Route for Photosensitive Poly(benzoxazole)"J.Polym.Sci.Part-A Polym.Chem. 40. 3379-3405 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Fukuhara, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of Thermosetting Poly(phenylene ether) containing Allyl Groups"Polymer. 45. 843-847 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Watanabe, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of Semiaromatic Polyimides from Aromatic Diamines Containing Adamantyl Units and Alicyclic Dianhydrides"J.Polym.Sci.Part-A, Polym.Chem.. 41. 144-150 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Matsumoto, Y.Shibasaki, S.Ando, M.Ueda: "Photosensitive Polymer Based on Poly(2,6-dihydroxy-1,5-naphthalene), a Cross-Linker, and a Photoacid Generator"J.Polym.Sci.Part-A, Polym.Chem.. (submitted for publication).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tsuchiya, Y.Shibasaki, M.Suzuki, Mitsuru Ueda: "Photosensitive Polymer Based on Poly(2,6-dihydroxy-1,5-naphthalene), a Cross-Linker, and a Photoacid Generator"J.Polym.Sci.Part-A Polym.Chem.. 42. 2235-2240 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Fukukawa, Y.Shibasaki, M.Ueda: "Photosensitive Poly(benzoxazole) via Poly(ο-hydroxy azomethine) II : Environmentally Benign Process in Ethyl Lactate"Polym.J.. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tsuchiya, Y.Shibasaki, M.Suzuki, M.Ueda: "A Positive Type Alkaline Developable Thermally stable and Photosensitive Poly(2,6-dihydroxy-1,5-naphthylene), an acidolytic de-cross-linker, and a Photoacid Generator"Polymer. (submitted for publication).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tsuchiya, H.Ishii, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of a Novel Poly(Biaphthalene ether)r with a Low Dielectric Constant"Macromolecules. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tuchiya, Y.Shibasaki, M.Suzuki, M.Ueda: "A New Negative-Type Photosensitive Polymer Based on Poly(2,6-dihydro-1,5-naphthylene), a Cross-Linker, and a Photoacid Generator"J.Photopolym.Sci & Technol.. 16. 285-286 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Ueda, K.Ebara, Y.Shibasaki: "New Convenient Synthetic Route for Photosensitive Poly(benzoxazole)"J.Photopolym.Sci & Technol.. 16. 237-242 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "Chemically Amplified Photosensitive Poly(benzoxazole)"J.Photopolym. Sci & Technol.. 16. 287-292 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Morita, K.Ebara, Y.Shibasaki, K.Goto, S.Tami, M.Ueda: "New Positive-type Photosensitive Polyimide Having Sulfo Groups"Polymer. 44. 6235-6239 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "Photosensitive poly(benzoxazole) based on Precursor from Diphenyl Isophthalate and Bis(o-aminophenol)"Polymer. 44. 333-339 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Sasada, Y.Shibasaki, M.Suzuki, M.Ueda: "Convenient Synthesis of Poly(2,6-dihydroxy-1,5-naphthylene) by Cu(II)-amin Catalyzed Oxidative Coupling Polymerization"Polymer. 44. 355-360 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Sasada, Y.Shibasaki, M.Suzuki, M.Ueda: "New Positive-Type Photosensitive Polymer Based on Poly(2,6-dihydroxy-1,5-naphthylene) and Diazonaphtoquinoe"J.Polym.Sci.Part-A Polym.Chem.. 40. 393-398 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Watanabe, Y.Sakai, Y.Shibasaki, S.Ando, M.Ueda, Y.Oishi, K.Mori: "Synthesis of Wholly Alicyclic Polyimides from N-Silylated Alicyclic Diamines and Alicyclic Dianhydrides"Macromolecules. 35. 2277-2281 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Watanabe, Y.Shibasaki, S.Ando, M.Ueda.: "A New Positive-Type Photosensitive Alkaline-Developable Alicyclic Polyimide Based on Poly(amic acid silylester) as a Polyimide Precursor and Diazonaphthoquinone as a Photosensitive Compound"Chem.Mater.. 14. 1762-1766 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "New Synthetic Route for Photosensitive Poly(benzoxazole)"J.Polym.Sci.Part-A Polym.Chem.. 40. 3379-3405 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Tuchiya, Y.Shibasaki, M.Suzuki, M.Ueda: "A New Negative-Type Photosensitive Polymer Based on Poly (2,6-dihydro-1,5-naphthalene), a Cross-Linker, and a Photoacid Generator"J.Photopolym.Sci.& Technol.. 16. 285-286 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Fukuhara, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of Thermosetting Poly(phenylene ether) containing Allyl Groups"Polymer. 45. 843-847 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "New Synthetic Route for Photosensitive Poly(benzoxazole)"J.Polym.Sci.Part-A Polym.Chem.. 40. 3379-3405 (2002)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Tsuchiya, Y.Shibasaki, M.Suzuki, M.Ueda: "Photosensitive Polymer Based on Poly(2,6-dihydroxy-1,5-naphthalene), A Cross-Linker, and a Photoacid Generator"J.Polym.Sci.Part-A Polym.Chem.. (in press).

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Watanabe, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of Semiaromatic Polyimides from Aromatic Diamines Containing Adamantyl Units and Alicyclic Dianhydrides"J.Polym.Sci.Part-A Polym.Chem.. 41. 144-150 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Fukukawa, Y.Shibasaki, M.Ueda: "Photosensitive Poly(benzoxazole) via Poly(o-hydroxy azomethine) II : Environmentally Benign Process in Ethyl Lactate"Polym.J.. (in press).

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Ueda, K.Ebara, Y.Shibasaki: "New Convenient Synthetic Route for Photosensitive Poly(benzoxazole)"J.Photopolym.Sci.& Technol.. 16. 237-242 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "Chemically Amplified Photosensitive Poly(benzoxazole)"J.Photopolym.Sci.& Technol.. 16. 287-292 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Morita, K.Ebara, Y.Shibasaki, K.Goto, S.Tami, M.Ueda: "New Positive-type Photosensitive Polyimide Having Sulfo Groups"Polymer. 44. 6235-6239 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Matsumoto, Y.Shibasaki, S.Ando, M.Ueda: "Synthesis of photosensitive and Thermosetting Poly(phenylene ether) Containing Allyl Groups"J.Photopolym.Sci.& Technol.. (in press).

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Sasada, Y.Shibasaki, M.Suzuki, M.Ueda: "New Positive-Type Photosensitive Polymer Based on Poly (2,6-dihydroxy -1,5-naphthylene) and Diazonaphtoquinone"J.Polym.Sci.Part-A Polym.Chem. 40. 393-398 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Watanabe, Y.Sakai, Y.Shibasaki, S.Ando, M.Ueda, Y.Oishi, K.Mori: "Synthesis of Wholly Alicyclic Polyimides from-Silylated Alicyclic Diamines and Alicyclic Dianhydrides"Macromolecules. 35. 2277-2281 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Watanabe, Y.Shibasaki, S.Ando, M.Ueda: "A New Positive-Type Photosensitive AlkalineDevelopable Alicyclic Polyimide Based on Poly(amic acid silylester) a Polyimide Precursor and Diaonaphthoquinone a sa Photosensitive Compound"Chem.Mater. 14. 1762-1766 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "New Synthetic Route for Photosensitive Poly(benzoxazole)"J.Polym.Sci.Part-A Polym.Chem. 40. 3379-3405 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Ebara, Y.Shibasaki, M.Ueda: "Photosensitive poly(benzoxazole) based on Precursor from Diphenyl Isophthalate and Bis (aminophenol)"Polymer. 44. 333-339 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.Sasada, Y.Shibasaki, M.Suzuki, M.Ueda: "Convenient Synthesis of Poly ( 2, dihydroxy-1, 5-naphthylene) by Cu(II)-amin Catalyzed Oxidative Coupling Polymerization"Polymer. 44. 355-360 (2003)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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