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Denvelopment of OLED materials based on polyaromatic hydrocarbons possessing semi- and super-conductivities

Research Project

Project/Area Number 18H02043
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionGunma University

Principal Investigator

Yamaji Minoru  群馬大学, 大学院理工学府, 准教授 (20220361)

Co-Investigator(Kenkyū-buntansha) 岡本 秀毅  岡山大学, 自然科学研究科, 准教授 (30204043)
Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Fiscal Year 2020: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2019: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2018: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
Keywords光環化反応 / 多環芳香族炭化水素 / 有機半導体性 / 有機超伝導性 / 固体発光 / フェナセン / 多環芳香族炭化水素化合物 / 有機半導体 / 有機超伝導体 / 有機EL発光素子 / 有機超伝導 / OLED発光体 / 光縮環反応 / マイクロフローリアクター / 有機超電装 / 高発光効率分子 / OLED / 電界発光素子 / 有機ELケイ光体
Outline of Final Research Achievements

Organic synthesis of fused aromatic compounds of a large number of the benzene ring requires multistep synthetic procedures whereas photocylization process of corresponding ethene precursors is a facile procedure for synthesizing them. In advance of the main study, we made a flowphotoreactor that achieves efficient photocyclization. By using this instrument, we synthesized small phenacene derivatives, such as phenanthrene, chrysene and picene, with bromomethyl and formyl groups at various substituted positions used as the basic chromophores for the following photocyclization of diarylethenes. We prepared various diarylethenes, and carried out their photocyclization to obtain a variety of cyclized aromatic compound. Photophysical properties of compounds were studied based on emission and transient absorption measurements as well as the single crystal structures by X-ray crystallography. The electronic properties as semiconductor and electroluminescence devices were examined.

Academic Significance and Societal Importance of the Research Achievements

光環化反応で作成可能なフェナセンは外部環境に対し堅牢であり半導体性・超伝導性を示し、ベンゼン環数を変化させると電気物性が変化する一方、発光効率は良くない。本研究の成果としてフェナセンをビルディングブロックとした複数のクロモファーから成る芳香族化合物が効率の良い固体青色発光を誘起することを見出した。マルチクロモファー分子は青色OLEDの発光層としての応用が期待される。また、ベンゼン環の縮環様式をフェナセンとアセンのハイブリッド化した分子の半導体性が分子の対称性に依存することを見出した。この発見は、有機半導体化合物の設計方針の一助になると考えられる。

Report

(4 results)
  • 2022 Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (29 results)

All 2023 2022 2019 2018 Other

All Journal Article (15 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 15 results,  Open Access: 3 results) Presentation (11 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results) Remarks (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Red, green, and blue radio-luminescent polymer dots doped with heteroleptic tris-cyclometalated iridium complexes2023

    • Author(s)
      Liu Zouyue、Nguyen Hieu Thi Minh、Asanuma Daiki、Tojo Sachiko、Yamaji Minoru、Kawai Kiyohiko、Pratx Guillem、Fujitsuka Mamoru、Osakada Yasuko
    • Journal Title

      RSC Advances

      Volume: 13 Issue: 22 Pages: 15126-15131

    • DOI

      10.1039/d3ra01216f

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Solvent-dependent fluorescence behaviour of imide-fused [<i>n</i>]phenacenes (<i>n</i> = 3, 5, 7)2023

    • Author(s)
      Nose Keito、Yoshioka Kaito、Yamaji Minoru、Tani Fumito、Goto Kenta、Okamoto Hideki
    • Journal Title

      RSC Advances

      Volume: 13 Issue: 6 Pages: 4096-4101

    • DOI

      10.1039/d2ra07771j

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Star-burst polycyclic aromatic hydrocarbons prepared by multi-photocyclization and the photophysical features2023

    • Author(s)
      Yamaji Minoru、Okamoto Hideki
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 436 Pages: 114387-114387

    • DOI

      10.1016/j.jphotochem.2022.114387

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Mesolysis of an asymmetric diphenyldisulfide radical anion studied by <i>γ</i>-ray and pulsed-electron radiolyses2023

    • Author(s)
      Yamaji Minoru、Tojo Sachiko、Majima Tetsuro、Fujitsuka Mamoru
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 25 Issue: 13 Pages: 9152-9157

    • DOI

      10.1039/d3cp00780d

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fabrication and characterization of thin-film field-effect transistors with alkyl-phenyl[n]phenacenes (n=4-6)2022

    • Author(s)
      Zhang, Yanting; Eguchi, Ritsuko; Okamoto, Hideki; Goto, Kenta; Tani, Fumito; Yamaji, Minoru; Goto, Hidenori; Kubozono, Yoshihiro
    • Journal Title

      J. Mater. Chem. C

      Volume: 10 Issue: 43 Pages: 16309-16320

    • DOI

      10.1039/d2tc03383f

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Blue fluorescence from N,O-coordinated BF2 complexes having aromatic chromophores in solution and solid state2019

    • Author(s)
      Minoru Yamaji, Kazuhiro Tomonari, Keisuke Ikuma, Kenta Goto, Fumito Tani, Hideki Okamoto
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 18 Issue: 12 Pages: 2884-2892

    • DOI

      10.1039/c9pp00410f

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorescence properties of amido-substituted 2,3-naphthalimides: Excited-state intramolecular proton transfer (ESIPT) fluorescence and responses to Ca2+ ions2019

    • Author(s)
      Lei Wang, Mayu Fujii, Misa Namba, Minoru Yamaji, Hideki Okamoto
    • Journal Title

      Tetrahedron Lett.

      Volume: 60 Issue: 43 Pages: 151189-151189

    • DOI

      10.1016/j.tetlet.2019.151189

    • NAID

      120007163673

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Spectroscopic properties of push-pull 2-(4-carboxyphenyl-6-dimethylaminobenzothiazole derivatives in solution and the solid state2019

    • Author(s)
      Takahashi, Yusuke; Uehara, Takuya; Matsuhashi, Chihiro; Yamaji, Minoru; Mutai, Toshiki; Yoshikawa, Isao; Houjou, Hirohiko; Kitagawa, Kota; Suenobu, Tomoyoshi; Maki, Shojiro; Hirano, Takashi
    • Journal Title

      Journal of Photochemistry and Photobiology, A: Chemistry

      Volume: 376 Pages: 324-332

    • DOI

      10.1016/j.jphotochem.2019.03.021

    • Related Report
      2019 Annual Research Report 2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Halogen-substituent effect on the spectroscopic properties of 2-phenyl-6-dimethylaminobenzothiazoles2019

    • Author(s)
      Misawa Rena、Matsuhashi Chihiro、Yamaji Minoru、Mutai Toshiki、Yoshikawa Isao、Houjou Hirohiko、Noguchi Keiichi、Maki Shojiro、Hirano Takashi
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 26 Pages: 1702-1705

    • DOI

      10.1016/j.tetlet.2019.05.052

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of isomeric coumarin-fluorene hybrids by photocyclization and the photophysical features2018

    • Author(s)
      Yamaji Minoru、Okamoto Hideki、Goto Kenta、Kato Shin-ichiro、Tani Fumito、Nakamura Yosuke
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 13 Pages: 1216-1219

    • DOI

      10.1016/j.tetlet.2018.02.033

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state2018

    • Author(s)
      Yamaji Minoru、Okamoto Hideki
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 印刷中 Pages: 1010-6030

    • DOI

      10.1016/j.jphotochem.2018.04.017

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Fluorescence behaviour of 2-, 3- and 4-amino-1,8-naphthalimides: effects of the substitution positions of the amino functionality on the photophysical properties2018

    • Author(s)
      Wang Lei、Fujii Mayu、Yamaji Minoru、Okamoto Hideki
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 17 Issue: 10 Pages: 1319-1328

    • DOI

      10.1039/c8pp00302e

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Excited-state intramolecular proton transfer (ESIPT) fluorescence from 3-amidophthalimides displaying RGBY emission in the solid state2018

    • Author(s)
      Okamoto, Hideki Itani, Kazumasa Yamaji, Minoru Konishi, Hiroyuki Ota, Hiromi
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 4 Pages: 388-391

    • DOI

      10.1016/j.tetlet.2017.12.049

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Laser Photolysis Studies of ω-Bond Dissociation in Aromatic Carbonyls of Five-Membered Rings Induced by Triplet Sensitization2018

    • Author(s)
      Fujino, Shota Yamaji, Minoru Marciniak, Bronislaw
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 365 Pages: 39-44

    • DOI

      10.1016/j.jphotochem.2018.07.028

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Structure-fluorescence relationship of push-pull 2-phenylbenzothiazole derivatives designed based on the firefly light-emitter2018

    • Author(s)
      Fujikawa Tomoya、Uehara Takuya、Yamaji Minoru、Kanetomo Takuya、Ishida Takayuki、Maki Shojiro、Hirano Takashi
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 14 Pages: 1431-1434

    • DOI

      10.1016/j.tetlet.2018.02.075

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] ジフェニルナフタレンの固体発光と結晶構造の関連性について2022

    • Author(s)
      山路 稔、岡本秀毅、鈴木健吾、務台俊樹、吉川功、北條博彦
    • Organizer
      2022光化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Blue fluorescence from N,O-coordinated BF2 complexes with aromatic chromophores in solution and solid state2019

    • Author(s)
      M. Yamaji
    • Organizer
      Asian Chemicl Confress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Blue fluorescence from N,O-coordinated BF2 complexes having aromatic chromophores in solution and solid state2019

    • Author(s)
      山路 稔
    • Organizer
      2019年光化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 放射線化学的手法によるジアリルエテンの光化学的性質の研究2019

    • Author(s)
      山路 稔
    • Organizer
      放射線化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Blue fluorescence from N,O-coordinated BF2 complexes having aromatic chromophores in solution and solid state2019

    • Author(s)
      M. Yamaji
    • Organizer
      The 12th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] カルボニル基をもつナフトール類とそのボロン錯体の光物理特性の研究2018

    • Author(s)
      山路稔、岡本秀毅、五島健太、谷文都
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] フタルイミド誘導体のESIP蛍光特性に及ぼすアミド置換2018

    • Author(s)
      伊谷一将、山路稔、岡本秀毅
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] π共役拡張フェナセンの光環化による合成と電子スペクトル特性2018

    • Author(s)
      岡本 秀毅 、久保園 久保園 芳博、浜尾 志乃 、郷田 慎、杉野 久子、 山路 稔
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Preparation of Amino-substituted 1,8-Naphthalimide Derivatives and Their Fluorescence Properties2018

    • Author(s)
      Lei Wang, Minoru Yamaji, Hideki Okamnoto
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state2018

    • Author(s)
      Minoru Yamaji,1 Hideki Okamoto,2 Kenta Goto3 and Fumito Tani
    • Organizer
      The 11th Japan-Taiwan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Photoinduced ω-bond dissociation of aromatic carbonyls in higher triplets triggered upon triplet sensitization studied by laser flash photolysis2018

    • Author(s)
      Minoru Yamaji
    • Organizer
      Asian Photochemistry Conference 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Remarks] 励起分子科学研究室

    • URL

      http://photochem.chem-bio.st.gunma-u.ac.jp/~yamaji/Japanese/Welcome.html

    • Related Report
      2018 Annual Research Report
  • [Patent(Industrial Property Rights)] 化合物、化合物の製造方法、青色発光材料及び有機発光素子2019

    • Inventor(s)
      山路 稔
    • Industrial Property Rights Holder
      山路 稔
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2019 Annual Research Report
  • [Patent(Industrial Property Rights)] 青色固体発光材料、青色固体発光材料の製造方法及び有機発光素子2019

    • Inventor(s)
      山路 稔
    • Industrial Property Rights Holder
      群馬大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2018 Annual Research Report

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Published: 2018-04-23   Modified: 2024-01-30  

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