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New synthesis of nitrogen-containing polyaryl compounds catalyzed by transitionmetal complexes and application to organic EL devices

Research Project

Project/Area Number 13555250
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Synthetic chemistry
Research InstitutionTohoku University

Principal Investigator

INOUE Yoshio  Tohoku University, Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (50005518)

Co-Investigator(Kenkyū-buntansha) KITA Hiroshi  Konica Minolta Japan, Technology Center, Chief Investigator, 材料技術研究所, 主任研究員
OI Shuichi  Tohoku University, Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (00241547)
Project Period (FY) 2001 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥13,400,000 (Direct Cost: ¥13,400,000)
Fiscal Year 2004: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2003: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 2002: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 2001: ¥7,700,000 (Direct Cost: ¥7,700,000)
Keywordsdirect arylation / ruthenium complex / aryl halide / organic EL device / phosphorescence luminescence / electron transporting material / C-H結合活性化 / アゾベンゼン / アリールカップリング / アルケニルピリジン / ロジウム錯体 / アリール化 / イミダゾリン / フェノール / 遷移金属錯体 / ポリアリール
Research Abstract

1.We observed that direct arylation of the ortho position in the benzene ring of 2-phenylpyridine took place when 2-phenylpyridine and aryl halides were reacted in the presence of a ruthenium complex catalyst and base. After intensive works, the best conditions were established for this important reaction as follows : Ruthenium complex catalysts coordinating tertiary phosphine, above all, [η^6-C_6H_6RuCl_2]_2-4PPh_3 showed the best performance in activity. The employment of potassium carbonate as base, N-methyl pyrrolidine as solvent, 120℃ as reaction temperature, 20-40 h as reaction time were found to be the best reaction conditions.
2.Pyridyl group is inevitable for the reaction to occur as the directing group which facilitates the ortho directing reaction by coordinating the ruthenium center. However pyridyl group is hard to be converted into another functional group. Development of easily convertible directing group seems essential. We exploited imino and oxazoyl group as the directing group for the direct ortho arylation of the aromatic ring. These groups can easily be converted into other functional groups : Imino group can be converted into ketone, aldehyde, alcohol, amine, and oxazole group can be converted into carboxylic acid, ester, and amide.
3.Then we prepared several nitrogen-containing polyaryl compounds utilizing above reaction method, and investigated the utility of these compounds as organic EL device. They were found to be good electron transporting material and also good ligand for iridium and platinum complexes with efficient phosphorescence luminescence.

Report

(5 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (34 results)

All 2005 2004 2003 2002 2001 Other

All Journal Article (15 results) Patent(Industrial Property Rights) (8 results) Publications (11 results)

  • [Journal Article] Ortho Selective Direct Cross-Coupling Reaction of 2-Aryloxazolines and 2-Arylimidazolines with Aryl and Alkenyl Halides Catalyzed by Ruthenium Complexes2005

    • Author(s)
      Shuichi Oi
    • Journal Title

      The Journal of Organic Chemistry (印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Rhodium-catalyzed addition of aryldifluoromethylsilanes to N-sulfonylaldimines2004

    • Author(s)
      Shuichi Oi
    • Journal Title

      Tetrahedron Letters 45

      Pages: 4855-4857

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Asymmetric 1,4-Addition of Alkenylzirconium Reagents to α,β-Unsaturated Ketones Catalyzed by Chiral Rhodium Complexes2004

    • Author(s)
      Shuichi Oi
    • Journal Title

      Tetrahedron Letters 45・26

      Pages: 5051-5055

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Rhodium-catalyzed addition of aryldifluoromethylsilanes to N-sulfonylaldimines2004

    • Author(s)
      Shuichi Oi
    • Journal Title

      Tetrahedron Letters 45・25

      Pages: 4855-4857

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Asymmetric 1,4-Addition of Organosiloxanes to α,β-Unsaturated Carbonyl Compounds Catalyzed by a Chiral Rhodium Complex2003

    • Author(s)
      Shuichi Oi
    • Journal Title

      Organic Letters 5

      Pages: 97-99

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Rhodium-catalyzed addition of arylstannanes to carbon-heteroatom double bond2003

    • Author(s)
      Shuichi Oi
    • Journal Title

      Tetrahedron 59

      Pages: 4351-4361

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Rhodium-HMPT-catalyzed direct ortho arylation of phenols with aryl bromides2003

    • Author(s)
      Shuichi Oi
    • Journal Title

      Tetrahedron Letters 44

      Pages: 8665-8668

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Rhodium-catalyzed conjugate addition of aryl- and alkenyl-stannanes to α,β-unsaturated carbonyl compounds2002

    • Author(s)
      Shuichi Oi
    • Journal Title

      Tetrahedron 58

      Pages: 91-97

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Conjugate Addition of Organosiloxanes to α,β-unsatuated carbonyl compounds catalyzed by a Cationic Rhodium Complex2002

    • Author(s)
      Shuichi Oi
    • Journal Title

      Organic Letters 4

      Pages: 667-669

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Ruthenium Complex Catalyzed Direct Ortho Arylation and Alkenylation of Aromatic Imines with Organic Halides2002

    • Author(s)
      Shuichi Oi
    • Journal Title

      Organic Letters 4

      Pages: 1783-1785

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Rhodium-catalyzed conjugate addition of aryl-and alkenyl-stannanes to α, β -unsaturated carbonyl compounds2002

    • Author(s)
      Shuichi Oi
    • Journal Title

      Tetrahedron 58

      Pages: 91-97

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Conjugate Addition of Organosiloxanes to α,β -unsaturated carbonyl compounds catalyzed by a Cationic Rhodium Complex2002

    • Author(s)
      Shuichi Oi
    • Journal Title

      Organic Letters 4

      Pages: 667-669

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Rhodium-Catalyzed Addition of Phenylmethyldifluorosilane to Aldehydes2001

    • Author(s)
      Shuichi Oi
    • Journal Title

      Organometallics 20

      Pages: 1036-1037

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Cationic Platinum-Complex-Catalyzed Skeletal Reorganization of Enynes2001

    • Author(s)
      Shuichi Oi
    • Journal Title

      Organometallics 20

      Pages: 3704-3709

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Ruthenium Complex-Catalyzed Direct Ortho Arylation and Alkenylation of 2-Arylpyridines with Organic Halides2001

    • Author(s)
      Shuichi Oi
    • Journal Title

      Organic Letters 3

      Pages: 2579-2581

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子、表示装置2004

    • Inventor(s)
      井上 祥雄等
    • Industrial Property Rights Holder
      コニカミノルタ
    • Patent Publication Number
      2004-319438
    • Filing Date
      2004-02-27
    • Acquisition Date
      2004-11-11
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子用材料2004

    • Inventor(s)
      井上 祥雄等
    • Industrial Property Rights Holder
      コニカミノルタ
    • Industrial Property Number
      2004-051538
    • Filing Date
      2004-02-26
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子用材料2004

    • Inventor(s)
      井上 祥雄等
    • Industrial Property Rights Holder
      コニカミノルタ
    • Industrial Property Number
      2004-103249
    • Filing Date
      2004-03-31
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子用材料2004

    • Inventor(s)
      井上 祥雄等
    • Industrial Property Rights Holder
      コニカミノルタ
    • Industrial Property Number
      2004-103250
    • Filing Date
      2004-03-31
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子用材料2004

    • Inventor(s)
      井上 祥雄等
    • Industrial Property Rights Holder
      コニカミノルタ
    • Industrial Property Number
      2004-103251
    • Filing Date
      2004-03-31
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子,表示装置,照明装置及びロジウム錯体化合物2004

    • Inventor(s)
      北 弘志, 井上 祥雄外2名
    • Industrial Property Rights Holder
      コニカミノルタホールディングス株式会社
    • Patent Publication Number
      2004-319483
    • Filing Date
      2004-02-27
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子および表示装置2002

    • Inventor(s)
      井上 祥雄等
    • Industrial Property Rights Holder
      コニカミノルタ
    • Patent Publication Number
      2003-282270
    • Filing Date
      2002-03-25
    • Acquisition Date
      2003-10-03
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機エレクトロルミネッセンス素子及び表示装置2002

    • Inventor(s)
      井上 祥雄等
    • Industrial Property Rights Holder
      コニカミノルタ
    • Patent Publication Number
      2004-111193
    • Filing Date
      2002-09-18
    • Acquisition Date
      2004-04-08
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Shuichi Oi: "Asymmetric 1,4-addition of organosiloxanes to α,β-unsaturated cabonyl compounds catalyzed by a chiral rhodium complex"Organic Letters. 5・1. 97-99 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Shuichi Oi: "Rhodium-catalyzed addition of arystannanes to carbon-heteroatom double bond"Tetrahedron. 59・24. 4351-4361 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Shuichi Oi: "Rhodium-HMPT-catalyzed direct ortho arylation of phenols with aryl bromides"Tetrahedron Letters. 44・48. 8665-8668 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Shuichi Oi: "Rhodium-catalyzed conjugate addition of aryl-and alkenylstannanes to α,β-unsaturated carbonyl compounds"Tetrahedron. 58・1. 91-97 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shuichi Oi: "Conjugate Addition of Organosiloxanes to α,β-Unsaturated Carbonyl Compounds Catalyzed by a Cationic Rhodium Complex"Organic Letters. 4・4. 667-669 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shuichi Oi: "Ruthenium Complex Catalyzed Direct Ortho Arylation and Alkenylation of Aromatic Imines with Organic Halides"Organic Letters. 4・10. 1783-1785 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shuichi Oi: "Asymmetric 1,4-Addition of Organosiloxanes to α,β-Unsaturated Carbonyl Compounds Catalyzed by a Chiral Rhodium Complex"Organic Letters. 5・1. 97-99 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] Shuichi Oi: "Rhodium-Catalyzed Addition of Phenylmethyldifluorosilane to Aldehdes"Organometallics. 20, 6. 1036-1037 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Naofumi Tsukada: "Synthesis and crystal structure of twisted dinuclear η^3-allylpalladium complexes containing tetradentate ligands"Journal of Organometallic Chemistry. 627. 121-126 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Shuichi Oi: "Catinic Platinum-Complex-Catalyzed Skeletal Reorganization of Enynes"Organometallics. 20, 17. 3704-3709 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Shuichi Oi: "Ruthenium Complex-Catalyzed Direct Ortho Arylation and Alkenylation of 2-Arylpyridines with Organic Halides"Organic Letters. 3, 16. 2579-2581 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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