Development of solution-processible highly crystalline organic semiconductor materials using reversible complexation of boron atom and their applications

• Project/Area Number: 17K17937
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic and hybrid materials; Organic chemistry
• Research Institution: Kyushu University
• Principal Investigator: MATSUO Kyohei 九州大学, 稲盛フロンティア研究センター, 特別研究員(SPD) (00778904)
• Project Period (FY): 2017-04-01 – 2019-03-31
• Project Status: Completed (Fiscal Year 2018)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2018: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2017: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 有機半導体 / 有機発光ダイオード / ホウ素

Outline of Final Research Achievements

Donor-acceptor type thermally activated delayed fluorescence molecules containing boronate-ester and boronate-thioester moieties as electron-accepting units were synthesized. High performance organic light-emitting diodes (OLEDs) based on these molecules have been successfully fabricated. While OLEDs with a boronate-thioester-based emitter achieved a high external electroluminescence quantum efficiency of 20%, OLEDs with a boronate-ester-based emitter exhibited deep-blue electroluminescence with external electroluminescence quantum efficiency of 12%.

Academic Significance and Societal Importance of the Research Achievements

有機発光ダイオードに代表される有機エレクトロルミネッセンス素子は、テレビやスマートフォンのディスプレイ等に実用化が進められており、高効率な発光材料の開発が望まれている。特に、フルカラー表示や白色光源に必要な青色発光材料では材料が限られており、大きな課題となっている。本研究では、分子を構成する元素をわずかに変えることで、発光効率や発光色が大きく変わることを見出し、優れた青色発光材料の開発に成功した。

Research Products

• [Journal Article] Boronate- and Borinate-Based π-Systems for Blue Thermally Activated Delayed Fluorescence Materials (2019)
  • Author(s): Kyohei Matsuo and Takuma Yasuda
  • Journal Title: Chemical Communications Volume: 55 Issue: 17 Pages: 2501-2504
  • DOI: 10.1039/c8cc10282a
  • Peer Reviewed
• [Journal Article] High-Performance Dibenzoheteraborin-Based Thermally Activated Delayed Fluorescence Emitters: Molecular Architectonics for Concurrently Achieving Narrowband Emission and Efficient Triplet-Singlet Spin Conversion (2018)
  • Author(s): In Seob Park, Kyohei Matsuo, Naoya Aizawa, and Takuma Yasuda
  • Journal Title: Advanced Functional Materials Volume: 28 Issue: 34 Pages: 1802031-1802031
  • DOI: 10.1002/adfm.201802031
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Highly Efficient Red-Orange Delayed Fluorescence Emitters Based on Strong π-Accepting Dibenzophenazine and Dibenzoquinoxaline Cores: toward a Rational Pure-Red OLED Design (2018)
  • Author(s): Furue Ryuhei、Matsuo Kyohei、Ashikari Yasuhiko、Ooka Hirohito、Amanokura Natsuki、Yasuda Takuma
  • Journal Title: Advanced Optical Materials Volume: 6 Issue: 5 Pages: 1701147-1701147
  • DOI: 10.1002/adom.201701147
  • Peer Reviewed
• [Journal Article] Enhancing thermally activated delayed fluorescence characteristics by intramolecular B-N coordination in a phenylpyridine-containing donor-acceptor π-system (2017)
  • Author(s): Matsuo Kyohei、Yasuda Takuma
  • Journal Title: Chemical Communications Volume: 53 Issue: 62 Pages: 8723-8726
  • DOI: 10.1039/c7cc04875k
  • Peer Reviewed
• [Presentation] Optoelectronic Properties of Doubly Twisted Donor-π-Acceptor Type Thermally Activated Delayed Fluorescence Molecules (2018)
  • Author(s): Matsuo Kyohei、Yasuda Takuma
  • Organizer: The Third International Symposium on the Synthesis and Application of Curved Organic π-Molecules & Materials (CURO-π3)
  • Int'l Joint Research
• [Presentation] Doubly Twisted Donor-π-Acceptor Type Thermally Activated Delayed Fluorescence Molecules and Their Applications in Organic Light-Emitting Diodes (2018)
  • Author(s): Matsuo Kyohei、Yasuda Takuma
  • Organizer: The Ninth International Forum on Chemistry of Functional Organic Chemicals (IFOC-9)
  • Int'l Joint Research
• [Presentation] Effect of Heteroatom Substitution on Photoluminescence and Electroluminescence Properties of Dibenzoheteraborin-Based Thermally Activated Delayed Fluorescence (2018)
  • Author(s): Kyohei Matsuo, In Soeb Park, Naoya Aizawa, Jiyoung Lee, Takuma Yasuda
  • Organizer: 日本化学会第98春季年会
• [Presentation] Energy Gap Tuning of Thermally Activated Delayed Fluorescence Emitters by Intramolecular B-N Coordination and Its Application in Organic Light-emitting Diodes (2017)
  • Author(s): Kyohei Matsuo, Takuma Yasuda
  • Organizer: 13th International Symposium on Functional π-Electron Systems
  • Int'l Joint Research
• [Presentation] ジベンゾ[b,e][1,4]ヘテラボリン骨格を用いた高効率熱活性化遅延蛍光材料の開発と有機発光ダイオードへの応用 (2017)
  • Author(s): 松尾恭平、パクインソプ、相沢直矢、李ジヨン、安田琢麿
  • Organizer: 第28回基礎有機化学討論会
• [Patent(Industrial Property Rights)] エレクトロクロミック化合物 (2019)
  • Inventor(s): 後藤 大輔・安田 琢麿・松尾 恭平・清永 紀行
  • Industrial Property Rights Holder: 九州大学、株式会社リコー
  • Industrial Property Rights Type: 特許
  • Industrial Property Number: 2019-035010
  • Filing Date: 2019
• [Patent(Industrial Property Rights)] 含ホウ素多環芳香族化合物とそれを用いた有機EL素子 (2018)
  • Inventor(s): 宮崎 祐樹・藤田 悦昌・安田 琢麿・松尾 恭平
  • Industrial Property Rights Holder: 九州大学、三星ディスプレイ株式会社
  • Industrial Property Rights Type: 特許
  • Filing Date: 2018