Creation of Revolutionary Organic Light-emitting Materials Exhibiting Highly Efficient Solid-state Emission

• Project/Area Number: 22350081
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Functional materials/Devices
• Research Institution: Kyoto Institute of Technology (2011-2012); Kyoto University (2010)
• Principal Investigator: SHIMIZU Masaki 京都工芸繊維大学, 工芸科学研究科, 教授 (10272709)
• Co-Investigator(Kenkyū-buntansha): MORISUE Mitsuhiko 京都工芸繊維大学, 工芸科学研究科, 助教 (40403357)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥11,830,000 (Direct Cost: ¥9,100,000、Indirect Cost: ¥2,730,000); Fiscal Year 2012: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000); Fiscal Year 2011: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000); Fiscal Year 2010: ¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
• Keywords: 発光材料 / 蛍光 / 固体蛍光 / 固体発光 / パイ共役系 / 量子収率 / キナクリドン

Research Abstract

We have succeeded in the development of diaminobis(styryl)-benzenes, diaminoterephthalates, bis(EWD-substituted phenyl)bis(EDG-substituted phenyl)ethenes, spirobi(2,3-diarylindene)s, and silicon-bridged 2-arylindoles as novel fluorophores that exhibit highly efficient photoluminescence in the solid states. The relationship between substituents and emission colors are disclosed in each chromophore. Some of the designed compounds are confirmed to act as superior light-emitting materials in organic light-emitting devices.

Research Products

• [Journal Article] ケイ素ビアリールの新合成法と発光特性 (2013)
  • Author(s): 清水剛毅
  • Journal Title: 有機合成化学協会誌 Volume: 71(4) Pages: 307-318
  • URL: http://dx.doi.org/10.5059/yukigoseikyokaishi.71.307
  • Peer Reviewed
• [Journal Article] 固体のままで美しく発光する有機材料 (2013)
  • Author(s): 清水剛毅
  • Journal Title: 化学 Volume: 68(1) Pages: 24-29
  • URL: http://www.kagakudojin.co.jp/kagaku/web-kagaku03/c6801/c6801-shimizu/HTML/index1.html
  • Peer Reviewed
• [Journal Article] Efficient blue electroluminescence of silylenebridged 2-(2-naphthyl)indole (2012)
  • Author(s): Shimizu, M.;Mochida, K.; Asai, Y.; Yamatani, A.; Kaki, R.;Hiyama, T.; Nagai, N.; Yamagishi, H.; Furutani, H.
  • Journal Title: J. Mater. Chem Volume: 22(10) Issue: 10 Pages: 4337-4342
  • DOI: 10.1039/c2jm15173a
  • Peer Reviewed
• [Journal Article] 1,4-Bis(diarylamino)-2,5-bis(4-cyanophenylethenyl) benzenes: Fluorophores Exhibiting Efficient Red and Near-Infrared Emissions in Solid State (2012)
  • Author(s): Shimizu, M.; Kaki, R.; Takeda, Y.; Hiyama, T.; Nagai, N.; Yamagishi, H.; Furutani, H.
  • Journal Title: Angew. Chem. Int. Ed Volume: 51(17) Pages: 4095-4099
  • Peer Reviewed
• [Journal Article] Silicon-Bridged Biaryls: Molecular Design, New Synthesis, and Luminescence Control (2012)
  • Author(s): Shimizu, M.; Hiyama, T.
  • Journal Title: Synlett Volume: 23(07) Issue: 07 Pages: 973-989
  • DOI: 10.1055/s-0031-1290566
  • Peer Reviewed
• [Journal Article] 1,4-Bis(diarylamino)-2,5-bis(4-cyanophenylethenyl)benzenes: Fluorophores Exhibiting Efficient Red and Near-Infrared Emissions in Solid State (2012)
  • Author(s): Masaki Shimizu
  • Journal Title: Angewandte Chemie International Edition Volume: 51 Issue: 17 Pages: 4095-4099
  • DOI: 10.1002/anie.201108943
  • Peer Reviewed
• [Journal Article] Photophysical properties of heteroaromatic ring-fused (di)benzosiloles. (2011)
  • Author(s): Shimizu, M.; Mochida, K.; Katoh, M.; Hiyama, T.
  • Journal Title: Sci. China Chem Volume: 54(12) Issue: 12 Pages: 1937-1947
  • DOI: 10.1007/s11426-011-4396-6
  • Peer Reviewed
• [Journal Article] Highly Efficient Blue Fluorescence from 3,2'- Silylene-Bridged 2-Phenylindoles in the Solid State (2011)
  • Author(s): Shimizu, M.; Mochida, K.; Hiyama, T.
  • Journal Title: J.Phys. Chem. C Volume: 115(22) Issue: 22 Pages: 11265-11274
  • DOI: 10.1021/jp201168x
  • Peer Reviewed
• [Journal Article] Synthesis and Photophysical Properties of Dimethoxybis(3,3,3-trifluoropropen-l-yl)benzenes : Compact Chromophores Exhibiting Violet Fluorescence in the Solid State (2011)
  • Author(s): Masaki Shimizu, Yohei Takeda, Masahiro Higashi, Tamejiro Hiyama
  • Journal Title: Chemistry-An Asian Journal Volume: 9 Issue: 9 Pages: 2536-2544
  • DOI: 10.1002/asia.201100176
  • Peer Reviewed
• [Journal Article] Twisting strategy applied to N,N-diorganoquinacridones leads to organic chromophores exhibiting efficient solid-state fluorescence. (2011)
  • Author(s): Shimizu, M.; Asai, Y.; Takeda, Y.; Yamatani, A.; Hiyama, T.
  • Journal Title: Tetrahedron Lett Volume: 52(32) Issue: 32 Pages: 4084-4089
  • DOI: 10.1016/j.tetlet.2011.05.087
  • Peer Reviewed
• [Journal Article] Synthesis and Photophysical Properties of Dimethoxybis (3,3,3-trifluoropropen-1-yl) benzenes : Compact Chromophores Exhibiting Violet Fluorescence in the Solid State (2011)
  • Author(s): Shimizu Masaki, Takeda Youhei, Higashi Masahiro, Hiyama Tamejiro
  • Journal Title: Chemistry-An Asian Journal Volume: 6 Pages: 2536-2544
  • Peer Reviewed
• [Presentation] D-π-A 型シラフルオレンの設計と白色 発光ポリマーへの対応 (2013)
  • Author(s): 清水剛毅
  • Organizer: 日本化学会第93春季年会
  • Place of Presentation: 立命館大学(草津)
• [Presentation] D-π-A 型シラフルオレンの設計と白色 発光ポリマーへの応用 (2013)
  • Author(s): 清水正毅
  • Organizer: 日本化学会第９３春季年会
  • Place of Presentation: 立命館大学
• [Presentation] reparation and Properties of Silylene-bridged 2-(2-naphthyl)indole (2012)
  • Author(s): Masaki Shimizu
  • Organizer: 4th Asian Silicon Symposium
  • Place of Presentation: Tsukuba
• [Presentation] Preparation and Properties of Silylene-bridged 2-(2-naphthyl)indole (2012)
  • Author(s): Masaki Shimizu
  • Organizer: 4th Asian Silicon Symposium
  • Place of Presentation: Tsukuba, Japan
• [Presentation] Silicon-bridged Biaryls: Molecular Design, New Synthesis, and Luminescence Control (2011)
  • Author(s): Masaki Shimizu
  • Organizer: 6th Green Elements Science Symposium (International Symposium)
  • Place of Presentation: Okayama
  • Year and Date: 2011-12-03
• [Presentation] 2,3-ジアリールインデン誘導体の光物性 (2011)
  • Author(s): 清水正毅・富岡陽介・山谷昭徳・浅井唯我・檜山爲次郎
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-29
• [Presentation] 2,5-ジアミノー1,4-ジアロイルベンゼンの光物性 (2011)
  • Author(s): 浅井唯我・清水正毅・檜山爲次郎
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-29
• [Presentation] パラジウム触媒を用いる1,2-ジボリル化合物と1-アルキニル-2-(2,2-ジブロモエテニル)アレーンとの連続的交差カップリング/カルボパラジウム化/交差カップリング反応 (2011)
  • Author(s): 門脇嗣規・長尾育弘・清水正毅
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
  • Year and Date: 2011-03-27
• [Presentation] Palladium-catalyzed Synthesis and Luminescent Properties of Silicon-bridged Biaryls (2011)
  • Author(s): Masaki Shimizu
  • Organizer: 2011 Japan-Taiwan Joint Symposium on Organic Chemistry
  • Place of Presentation: Kyoto
• [Presentation] Palladium-catalyzed Synthesis and Luminescent Properties of Silicon-bridged Biaryls (2011)
  • Author(s): Masaki Shimizu
  • Organizer: Second International Collaborative and Cooperative Chemistry Symposium
  • Place of Presentation: The University of Queensland, Brisbane (Australia)
• [Presentation] Design and development of novel π-conjugated molecules exhibiting highly efficient solid state emission (2011)
  • Author(s): Masaki Shimizu
  • Organizer: 10th International Symposium on Functional π-Electron Systems
  • Place of Presentation: Friendship Hotel, Beijing(China)
• [Presentation] Palladium-Catalyzed Synthesis and Photophysical Properties of Silicon-Bridged Biaryls (2011)
  • Author(s): Masaki Shimizu
  • Organizer: The 14th Asian Chemical Congress (14ACC)
  • Place of Presentation: Bangkok (Thailand)
• [Presentation] Palladium-Catalyzed Synthesis and Photophysical Properties of Silicon-Bridged Biaryls (2011)
  • Author(s): Masaki Shimizu
  • Organizer: The 14th Asian Chemical Congress (14ACC)
  • Place of Presentation: Bangkok, Thailand
  • Invited
• [Presentation] Design and development of novel π‐conjugated molecules exhibiting highly efficient solid state emission (2011)
  • Author(s): Masaki Shimizu
  • Organizer: 10th International Symposium on Functional π-Electron Systems
  • Place of Presentation: Beijing, China
  • Invited
• [Presentation] Palladium-catalyzed Synthesis and Luminescent Properties of Silicon-bridged Biaryls (2011)
  • Author(s): Masaki Shimizu
  • Organizer: Second International Collaborative and Cooperative Chemistry Symposium
  • Place of Presentation: Brisbane, Australia
  • Invited
• [Presentation] Palladium-catalyzed Synthesis and Luminescent Properties of Silicon-bridged Biaryls (2011)
  • Author(s): Masaki Shimizu
  • Organizer: 2011 Japan-Taiwan Joint Symposium on Organic Chemistry
  • Place of Presentation: Kyoto, Japan
  • Invited
• [Presentation] Synthesis and Photophysical Properties of 2-Donor-7-acceptor-9-silafluorenes (2010)
  • Author(s): Masaki Shimizu, Kenji Mochida, Masaki Katoh, Tamejiro Hiyama
  • Organizer: 57th Symposium on Organometallic Chemistry, Japan
  • Place of Presentation: Tokyo, Japan
  • Year and Date: 2010-09-18
• [Presentation] Efficient Synthesis of Polycyclic Aromatic Hydrocarbons Based on Double Cross-coupling Reaction of vic-Diboryl Reagents and Bromo (2-bromoethenyl) arenes (2010)
  • Author(s): Ikuhiro Nagao, Masaki Shimizu, Yosuke Tomioka, Tsugumi Kadowaki, Tamerjiro Hiyama
  • Organizer: 57th Symposium on Organometallic Chemistry, Japan
  • Place of Presentation: Tokyo, Japan
  • Year and Date: 2010-09-18
• [Presentation] Development of Fluorinated π-conjugated Molecules Directed Toward Applications in Optoelectronic Devices (2010)
  • Author(s): Masaki Shimizu
  • Organizer: Perugia Fluorine Days
  • Place of Presentation: Perugia, Italy(招待講演)
  • Year and Date: 2010-07-13
• [Presentation] Synthesis and Properties of Fluorinated π-Conjugated Functional Molecules (2010)
  • Author(s): Masaki Shimizu
  • Organizer: The 8th Japan-China Symposium on Fluorochemical Industry
  • Place of Presentation: Tokyo, Japan(招待講演)
  • Year and Date: 2010-06-11
• [Presentation] Synthesis and Photophysical Properties of 2-Donor-7-acceptor-9-silafluorenes (2010)
  • Author(s): Masaki Shimizu
  • Organizer: 57th Symposium on Organometallic Chemistry
  • Place of Presentation: Tokyo
• [Presentation] Development of Fluorinated π-conjugated Molecules Directed Toward Applications in Optoelectronic Devices (2010)
  • Author(s): Masaki Shimizu
  • Organizer: Perugia Fluorine Days
  • Place of Presentation: Perugia (Italy)
• [Presentation] Synthesis and Properties of Fluorinated π-Conjugated Functional Molecules (2010)
  • Author(s): Masaki Shimizu
  • Organizer: The 8th Japan-China Symposium on Fluorochemical Industry
  • Place of Presentation: Tokyo
• [Presentation] Silicon-bridged Biaryls: Molecular Design, New Synthesis, and Luminescence Control
  • Author(s): Masaki Shimizu
  • Organizer: 6th Green Elements Science Symposium (International Symposium)
  • Place of Presentation: Okayama, Japan
  • Invited
• [Book] Diaminobenzene-Cored Fluorophores Exhibiting Highly Efficient Solid-State LuminescenceIn Aggregation- Induced Emission Chapter 4 (B. Z. Tang, A. Qin,Eds.) (2013)
  • Author(s): Masaki Shimizu
  • Publisher: Wiley(in press)