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Development of Ultraviolet Thermally Activated Delayed Fluorescence Molecules Based on Boron-Containing Conjugated Ladder-Type Structures

Research Project

Project/Area Number 21K05033
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionUniversity of Hyogo (2023)
Ibaraki University (2021-2022)

Principal Investigator

Agou Tomohiro  兵庫県立大学, 理学研究科, 教授 (90466798)

Co-Investigator(Kenkyū-buntansha) 安田 琢麿  九州大学, 高等研究院, 教授 (00401175)
Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2023: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2022: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2021: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords蛍光発光体 / 有機ホウ素化合物 / 二重発光分子 / 紫外発光分子 / 発光分子 / 紫外蛍光発光 / 蛍光分子 / 熱活性化遅延蛍光 / ヘテラボリン / 発光材料 / 有機エレクトロルミネッセンス / 有機典型元素化学 / 典型元素化学 / 近紫外発光体 / 有機ホウ素化学
Outline of Research at the Start

パイ共役骨格にホウ素を導入したラダー型ヘテラボリンを基本構造とし、熱活性化遅延蛍光特性を付与することで近紫外光を発する有機エレクトロルミネッセンス(EL)用発光体を開発する。本発光体と青・緑・赤の蛍光材料を組み合わせたHyperfluorescence素子を構築しフルカラー有機ELディスプレイや照明へ応用すると共に、医療用紫外光源への利用を検討し、水銀フリーの紫外光源の高効率化に貢献する。

Outline of Final Research Achievements

In this study, we have investigated the development of ultraviolet (UV) luminescent molecules based on the boron-containing ladder-type conjugated structures and their application to thermally activated delayed fluorescent (TADF)-type electroluminescent (EL) emitting matterials. Although the targeted TADF UV emitting materials have not been obtained so far, we synthesized several boron-containing fluorescent molecules showing optical functionality in ther course of the experimental studeis toward the UV-TADF molecules. We obtained conjugated ladder-type compounds that exhibited narrow-band near-UV fluorescence, which are currently under investigation as near-UV OLED emitting materials. We have also synthesized boron-conjugated ladder-type molecules that exhibit dual emission. The dual emissions were sensitive to enviromental changes, such as temperature, polarity, and viscosity.

Academic Significance and Societal Importance of the Research Achievements

狭帯域で色純度の高い紫外発光性分子は未だに例が少なく、本研究で開発した有機ホウ素化合物は近紫外領域での狭帯域発光を示し発光量子収率も高いものであったことから、紫外有機EL用発光体への展開が期待でき、現在、発光量子収率の向上とEL特性評価を検討している。また、本研究で合成した二重発光性ホウ素化合物は温度、極性、粘度といった環境変化に鋭敏に応答して発光が変化することから、環境センシングへの応用が可能である。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • 2021 Research-status Report
  • Research Products

    (22 results)

All 2024 2023 2022 2021

All Journal Article (17 results) (of which Peer Reviewed: 17 results) Presentation (2 results) (of which Invited: 1 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Synthesis and optical properties of tris(2,4,6-trichlorophenyl)methyl-type luminescent radicals bearing multiple carbazole substituents2024

    • Author(s)
      Yang Peiyuan、Nagata Masakazu、Fukumoto Hiroki、Nakashima Kouichi、Yasuda Takuma、Agou Tomohiro
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 97 Issue: 5

    • DOI

      10.1093/bulcsj/uoae045

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and optical properties of antimony(v) complexes of a trianionic N2O2-type tetradentate dipyrrin ligand2024

    • Author(s)
      Tomohiro Agou, Shunsuke Kuroiwa, Hiroki Fukumoto, Tatsuya Nabeshima
    • Journal Title

      Chemical Communications

      Volume: 60 Issue: 34 Pages: 4557-4560

    • DOI

      10.1039/d4cc00630e

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 3-Perfluoroalkylated fluorescent coumarin dyes: rational molecular design and photophysical properties2024

    • Author(s)
      Ikemura Ayano、Karuo Yukiko、Uehashi Yuki、Agou Tomohiro、Ebihara Masahiro、Kubota Yasuhiro、Inuzuka Toshiyasu、Omote Masaaki、Funabiki Kazumasa
    • Journal Title

      Molecular Systems Design & Engineering

      Volume: 9 Issue: 4 Pages: 332-344

    • DOI

      10.1039/d4me00006d

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and optical properties of dithieno-1,4-thiaborins bearing electron-donating amino groups2024

    • Author(s)
      Agou Tomohiro、Hayama Shota、Takano Naoya、Yamada Shigeyuki、Konno Tsutomu、Oshiki Toshiyuki、Komatsuzaki Hidehito、Fukumoto Hiroki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 97 Issue: 2

    • DOI

      10.1093/bulcsj/uoae014

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effects of fluorine atoms introduced into flexible chains or mesogenic structures on their liquid-crystalline and photoluminescence characteristics2024

    • Author(s)
      Yamada Shigeyuki、Yoshida Keigo、Hara Mitsuo、Agou Tomohiro、Yasui Motohiro、Konno Tsutomu
    • Journal Title

      Journal of Molecular Liquids

      Volume: 393 Pages: 123545-123545

    • DOI

      10.1016/j.molliq.2023.123545

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and characterization of a polystyrene-type polymer bearing a cyclic perfluoroalkylene group2023

    • Author(s)
      Hisa Tatsuro、Kanno Yasunori、Shirai Tomohiro、Oshiki Toshiyuki、Mizuhata Yoshiyuki、Tokitoh Norihiro、Fukumoto Hiroki、Agou Tomohiro
    • Journal Title

      Polymer

      Volume: 265 Pages: 125588-125588

    • DOI

      10.1016/j.polymer.2022.125588

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of perfluoroalkylene-vinylene-arylene copolymers via the Mizoroki-Heck co-polymerization of 1,4-divinylperfluorobutane and 1,6-divinylperfluorohexane with dihalogenated arylene monomers2022

    • Author(s)
      Tsukada Hiroto、Hisa Tatsuro、Shirai Tomohiro、Oshiki Toshiyuki、Mizuhata Yoshiyuki、Tokitoh Norihiro、Fukumoto Hiroki、Agou Tomohiro
    • Journal Title

      Journal of Fluorine Chemistry

      Volume: 261-262 Pages: 110033-110033

    • DOI

      10.1016/j.jfluchem.2022.110033

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photophysical and thermophysical behavior of D-π-A-type fluorinated diphenylacetylenes bearing an alkoxy and an ethoxycarbonyl group at both longitudinal molecular terminals2022

    • Author(s)
      Yamada Shigeyuki、Kataoka Mitsuki、Yoshida Keigo、Nagata Masakazu、Agou Tomohiro、Fukumoto Hiroki、Konno Tsutomu
    • Journal Title

      Journal of Fluorine Chemistry

      Volume: 261-262 Pages: 110032-110032

    • DOI

      10.1016/j.jfluchem.2022.110032

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Boron complexes of π-extended nitroxide ligands exhibiting three-state redox processes and near-infrared-II (NIR-II) absorption properties2022

    • Author(s)
      Nakamura Marika、Hyakutake Risa、Morisako Shogo、Sasamori Takahiro、Mizuhata Yoshiyuki、Tokitoh Norihiro、Nakashima Kouichi、Fukumoto Hiroki、Agou Tomohiro
    • Journal Title

      Dalton Transactions

      Volume: 51 Issue: 36 Pages: 13675-13680

    • DOI

      10.1039/d2dt02545k

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Aggregation-induced enhanced fluorescence by hydrogen bonding in π-conjugated tricarbocycles with a CF2CF2-containing cyclohexa-1,3-diene skeleton2022

    • Author(s)
      Ohsato Haruka、Morita Masato、Yamada Shigeyuki、Agou Tomohiro、Fukumoto Hiroki、Konno Tsutomu
    • Journal Title

      Molecular Systems Design & Engineering

      Volume: 7 Issue: 9 Pages: 1129-1137

    • DOI

      10.1039/d2me00055e

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Design, Regioselective Synthesis, and Photophysical Properties of Perfluoronaphthalene-Based Donor?Acceptor?Donor Fluorescent Dyes2022

    • Author(s)
      Funabiki Kazumasa、Yamada Kengo、Arisawa Yuta、Watanabe Arina、Agou Tomohiro、Kubota Yasuhiro、Inuzuka Toshiyasu、Miwa Yohei、Udagawa Taro、Kutsumizu Shoichi
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 87 Issue: 17 Pages: 11751-11765

    • DOI

      10.1021/acs.joc.2c01446

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Catalytic aerobic photooxidation of triarylphosphines using dibenzo-fused 1,4-azaborines2022

    • Author(s)
      Kondo Masaru、Agou Tomohiro
    • Journal Title

      Chemical Communications

      Volume: 58 Issue: 32 Pages: 5001-5004

    • DOI

      10.1039/d2cc00782g

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Regio- as well as stereoselective epoxide ring opening reactions using 3,3,3-trifluoroprop-1?yne2022

    • Author(s)
      Yamazaki Takashi、Iida Minato、Kawasaki-Takasuka Tomoko、Agou Tomohiro
    • Journal Title

      Journal of Fluorine Chemistry

      Volume: 257-258 Pages: 109971-109971

    • DOI

      10.1016/j.jfluchem.2022.109971

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, characterization, and formation of self-assembled monolayers of a phosphonic acid bearing a vinylene-bridged fluoroalkyl chain2022

    • Author(s)
      Shirai Tomohiro、Yamauchi Satoshi、Kikuchi Hikari、Fukumoto Hiroki、Tsukada Hiroto、Agou Tomohiro
    • Journal Title

      Applied Surface Science

      Volume: 577 Pages: 151959-151959

    • DOI

      10.1016/j.apsusc.2021.151959

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and photoluminescence properties of fluorine‐containing poly(phenylene vinylene) bearing hexafluorocyclopentene‐fused phenanthrene unit2021

    • Author(s)
      Fukumoto Hiroki、Shiitsuka Kazuki、Yamada Keisuke、Yamada Shigeyuki、Konno Tsutomu、Kubota Toshio、Agou Tomohiro
    • Journal Title

      Polymer International

      Volume: 71 Issue: 1 Pages: 117-123

    • DOI

      10.1002/pi.6291

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, structural characterization, and reactivity of a dinuclear cobalt(II) (μ-hydroxo)(μ-pyrazolato) complex based on a hydrotris(pyrazolyl)borate ligand2021

    • Author(s)
      Komatsuzaki Hidehito、Ohira Kazunari、Tadokoro Shun、Yamasaki Yuta、Oouchi Hitomi、Satoh Minoru、Agou Tomohiro、Tanaka Yuya、Akita Munetaka、Nakazawa Jun、Hikichi Shiro
    • Journal Title

      Inorganica Chimica Acta

      Volume: 527 Pages: 120533-120533

    • DOI

      10.1016/j.ica.2021.120533

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fused-Nonacyclic Multi-Resonance Delayed Fluorescence Emitter Based on Ladder-Thiaborin Exhibiting Narrowband Sky-Blue Emission with Accelerated Reverse Intersystem Crossing2021

    • Author(s)
      Masakazu Nagata, Hyukgi Min, Erika Watanabe, Hiroki Fukumoto, Yoshiyuki Mizuhata, Norihiro Tokitoh, Tomohiro Agou, Takuma Yasuda
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Issue: 37 Pages: 20280-20285

    • DOI

      10.1002/anie.202108283

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Presentation] ホウ素の特徴を活かした光機能性分子の開発2023

    • Author(s)
      吾郷友宏
    • Organizer
      相模中央化学研究所第7回材料相模セミナー
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] ドナー・アクセプター・ドナー型ジチエノチアボリンの合成と性質2022

    • Author(s)
      葉山翔太、吾郷友宏、福元博基
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Patent(Industrial Property Rights)] パーフルオロアルキレン基を有する芳香族化合物の製造方法2023

    • Inventor(s)
      吾郷友宏、馬場智也、井上大輔
    • Industrial Property Rights Holder
      吾郷友宏、馬場智也、井上大輔
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2023-216689
    • Filing Date
      2023
    • Related Report
      2023 Annual Research Report
  • [Patent(Industrial Property Rights)] 含フッ素スチレン誘導体及びその重合体並びにその製造方法2021

    • Inventor(s)
      吾郷友宏、福元博基、菅野康徳、比佐達郎、白井智大
    • Industrial Property Rights Holder
      東ソー・ファインケム株式会社
    • Industrial Property Rights Type
      特許
    • Filing Date
      2021
    • Acquisition Date
      2022
    • Related Report
      2022 Research-status Report
  • [Patent(Industrial Property Rights)] 含フッ素重合体及びその製造方法2021

    • Inventor(s)
      吾郷友宏、福元博基、塚田大翔、白井智大
    • Industrial Property Rights Holder
      東ソー・ファインケム株式会社
    • Industrial Property Rights Type
      特許
    • Filing Date
      2021
    • Acquisition Date
      2022
    • Related Report
      2022 Research-status Report

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Published: 2021-04-28   Modified: 2025-01-30  

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