Development of organic semiconductors based on organic chemistry and device physics: elucidation and utilization of physical properties

• Project/Area Number: 20KK0123
• Research Category: Fund for the Promotion of Joint International Research (Fostering Joint International Research (B))
• Allocation Type: Multi-year Fund
• Review Section: Medium-sized Section 35:Polymers, organic materials, and related fields
• Research Institution: Osaka University
• Principal Investigator: 家 裕隆 大阪大学, 産業科学研究所, 教授 (80362622)
• Co-Investigator(Kenkyū-buntansha): 横山 創一 大阪大学, 産業科学研究所, 助教 (40811211) ; 陣内 青萌 大阪大学, 産業科学研究所, 助教 (40861042) ; 安藤 直紀 大阪大学, 産業科学研究所, 助教 (80848979)
• Project Period (FY): 2020-10-27 – 2025-03-31
• Project Status: Granted (Fiscal Year 2023)
• Budget Amount: ¥18,720,000 (Direct Cost: ¥14,400,000、Indirect Cost: ¥4,320,000); Fiscal Year 2024: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000); Fiscal Year 2023: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2022: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2021: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
• Keywords: 有機半導体 / 共役化合物 / 有機太陽電池 / 有機エレクトロニクス

Outline of Research at the Start

有機エレクトロニクスは、次世代デバイスの有望候補である。本研究では、有機エレクトロニクスの新展開に繋がる有機半導体材料をマックスプランク高分子研究所と共同で開発することを目的とする。具体的には、分子設計指針が確立途上の物理的性質に着目し、これらの機能を積極的に付与した新機軸の有機半導体材料を創出する。本研究を通じて、若手研究者間の人的交流を含めた国際共同研究を系統的かつ多面的に実施することで、最先端の学術的知見を得るのみならず、分野横断型の強固な国際的ネットワークを構築する。

Outline of Annual Research Achievements

拡張π共役分子を有機半導体材料に応用する有機エレクトロニクスは、次世代デバイスの有望候補である。本研究では、有機エレクトロニクスの新展開に繋がる新機軸の有機半導体材料をマックスプランク高分子研究所（MPIP）の Blom 教授と共同で開発することを目的としてこれまで共同研究を行ってきた。とりわけ、高性能・高機能化に向けて重要であるにも関わらず、分子設計指針が確立途上の物理的性質に着目し、これらの機能を積極的に付与した新機軸の有機半導体材料を創出する。本研究では分子設計と有機合成を大阪大学産業科学研究所で実施し、研究代表者と研究分担者らがMPIPで薄膜・デバイス評価を行っている。有機エレクトロニクスにおけるデバイス物理の世界的研究拠点であるMPIPにおいて、プロジェクトリーダーの若手研究者間の人的交流を含めた国際共同研究を系統的かつ多面的に実施することで、最先端の学術的知見を得るのみならず、分野横断型の強固な国際的ネットワークを構築している。本年度の材料開発は昨年度に引き続き、励起子束縛エネルギーに着目した2次元構造の有機太陽電池材料の開発を行った。また、電子輸送材料に適した材料として、最低空軌道の深い分子開発を行い、現在、MPIPで物性評価を行っている。さらに、MPIPで見出した材料のエネルギーレベル評価に関しても阪大産研で行った。双極子モーメント、誘電率、近赤外吸収などのパラメーターに着目した材料開発も継続して行っている。

Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

電子輸送性材料、有機太陽電池など、有機エレクトロニクスに向けた材料開発は順調に進捗しており、MPIPとの共同研究を継続して実施しているため。

Strategy for Future Research Activity

今年度も引き続き材料開発と機能評価をMPIPと共同で実施する。

Research Products

• [Int'l Joint Research] マックスプランク高分子研究所(ドイツ)
• [Journal Article] Single-Layer Organic Light-Emitting Diode with Trap-Free Host Beats Power Efficiency and Lifetime of Multilayer Devices (2024)
  • Author(s): O. Sachnik, Y. Ie, N. Ando, X. Tan, P. W. M. Blom, G.-J. A. H. Wetzelaer
  • Journal Title: Adv. Mater. Volume: 36 Issue: 16 Pages: 2311892-2311892
  • DOI: 10.1002/adma.202311892
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Isothianaphthene Quinoids: Pyrazine-Annelated Structures for Tuning Electronic Properties (2024)
  • Author(s): K. Yamamoto, S. Jinnai, Y. Ie
  • Journal Title: Bull. Chem. Soc. Jpn. Volume: 97 Issue: 4
  • DOI: 10.1093/bulcsj/uoae036
  • Peer Reviewed
• [Journal Article] Green-light wavelength-selective organic solar cells for agrivoltaics: dependence of wavelength on photosynthetic rate (2024)
  • Author(s): S. Jinnai, N. Shimohara, K. Ishikawa, K. Hama, Y. Iimuro, T. Washio, Y. Watanabe, Y. Ie
  • Journal Title: Faraday Discuss. Volume: 250 Pages: 220-232
  • DOI: 10.1039/d3fd00141e
  • Peer Reviewed
• [Journal Article] Fluorinated Dihydropentalene-1,4-Dione: A Strong Electron-Accepting Unit with Organic Semiconductor Characteristics (2023)
  • Author(s): S. Yokoyama, Y. Ie
  • Journal Title: Chem. Eur. J. Volume: 29 Issue: 17
  • DOI: 10.1002/chem.202203873
  • Peer Reviewed
• [Journal Article] Green-Light Wavelength-Selective Organic Solar Cells Based on Poly(3-hexylthiophene) and Naphthobisthiadiazole-Containing Acceptors toward Agrivoltaics (2023)
  • Author(s): S. Jinnai, A. Oi, T. Seo, T. Moriyama, M. Terashima, M. Suzuki, K.-i. Nakayama, Y. Watanabe, Y. Ie
  • Journal Title: ACS Sustain. Chem. Eng. Volume: 11 Issue: 4 Pages: 1548-1556
  • DOI: 10.1021/acssuschemeng.2c06426
  • Peer Reviewed
• [Journal Article] Synthesis, Properties, and Photovoltaic Characteristics of Fluoranthenedione-containing Nonfullerene Acceptors for Organic Solar Cells (2022)
  • Author(s): S. Chatterjee, Y. Ie
  • Journal Title: Journal of Photopolymer Science and Technology Volume: 35 Issue: 2 Pages: 187-191
  • DOI: 10.2494/photopolymer.35.187
  • ISSN: 0914-9244, 1349-6336
  • Year and Date: 2022-12-16
  • Peer Reviewed
• [Journal Article] Tetrazolo[1,5-a]pyridine-Containing pi-Conjugated Systems: Synthesis, Properties, and Semiconducting Characteristics (2022)
  • Author(s): S. Tamba, M. Nitani, T. Seo, H. Nitta, H. Tanaka, K. Hagiya, Y. Aso, Y. Ie
  • Journal Title: Org. Lett. Volume: 24 Issue: 21 Pages: 3792-3796
  • DOI: 10.1021/acs.orglett.2c01310
  • Peer Reviewed
• [Journal Article] Effects of the rigid and sterically bulky structure of non-fused nonfullerene acceptors on transient photon-to-current dynamics (2022)
  • Author(s): Jinnai Seihou、Murayama Kasumi、Nagai Keisuke、Mineshita Megumi、Kato Kosaku、Muraoka Azusa、Yamakata Akira、Saeki Akinori、Kobori Yasuhiro、Ie Yutaka
  • Journal Title: Journal of Materials Chemistry A Volume: 10 Issue: 37 Pages: 20035-20047
  • DOI: 10.1039/d2ta02604j
  • Peer Reviewed / Open Access
• [Journal Article] A Fused pi-Extended Molecule Containing an Electron-Accepting Naphthobisthiadiazole and Its Incorporation into a Copolymer: Synthesis, Properties, and Semiconducting Performance (2022)
  • Author(s): R. Asakawa, T. Seo, S. Yokoyama, Y. Ie
  • Journal Title: Polym. J. Volume: 55 Issue: 4 Pages: 451-461
  • DOI: 10.1038/s41428-022-00716-x
  • Peer Reviewed
• [Journal Article] Role of Linker Functionality in Polymers Exhibiting Main-Chain Thermally Activated Delayed Fluorescence (2022)
  • Author(s): K. Philipps, Y. Ie, B. van der Zee, R.-Q. Png, P. K. H. Ho, L.-L. Chua, E. del Pino Rosendo, C. Ramanan, G.-J. A. H. Wetzelaer, P. W. M. Blom, J. J. Michels
  • Journal Title: Adv. Sci. Volume: ９ Issue: 19 Pages: 2200056-2200056
  • DOI: 10.1002/advs.202200056
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Cross-conjugated Isothianaphthene Quinoids: A Versatile Strategy for Controlling Electronic Structures (2022)
  • Author(s): K. Yamamoto, S. M. Quintero, S. Jinnai, E. Jeong, K. Matsuo, M. Suzuki, H. Yamada, J. Casado, Y. Ie
  • Journal Title: J. Mater. Chem. C Volume: 10 Issue: 11 Pages: 4424-4433
  • DOI: 10.1039/d1tc05794d
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Excited States Engineering Enables Efficient Near-infrared Lasing in Nanographenes (2022)
  • Author(s): G. M. Paterno, Q. Chen, R. Munoz-Marmol, M. Guizzardi, V. Bonal, R. Kabe, A. J. Barker, P. G. Boj, S. Chatterjee, Y. Ie, J. M. Villalvilla, J. A. Quintana, F. Scotognella, K. Mullen, M. A. Diaz-Garcia, A. Narita, G. Lanzani
  • Journal Title: Mater. Hor. Volume: 9 Issue: 1 Pages: 393-402
  • DOI: 10.1039/d1mh00846c
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Synthesis, Properties, and Photovoltaic Characteristics of Arch- and S-shaped Naphthobisthiadiazole-based Acceptors (2021)
  • Author(s): S. Jinnai, Y. Ie
  • Journal Title: Journal of Photopolymer Science and Technology Volume: 34 Issue: 3 Pages: 285-290
  • DOI: 10.2494/photopolymer.34.285
  • NAID: 130008119605
  • ISSN: 0914-9244, 1349-6336
  • Year and Date: 2021-06-11
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Electron-Accepting π-Conjugated Compound Containing Cyano-Substituted Naphthobisthiadiazole as Nonfullerene Acceptor in Organic Solar Cells (2021)
  • Author(s): S. Jinnai, A. Oi, T. Seo, T. Moriyama, R. Minami, S. Higashida, Y. Ie
  • Journal Title: Synthesis Volume: 53 Issue: 18 Pages: 3390-3396
  • DOI: 10.1055/a-1528-1632
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Nonfullerene acceptors for P3HT-based organic solar cells (2021)
  • Author(s): Chatterjee Shreyam, Seihou Jinnai, Yutaka Ie
  • Journal Title: Journal of Materials Chemistry A Volume: 9 Issue: 35 Pages: 18857-18886
  • DOI: 10.1039/d1ta03219d
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Single-Molecule Conductance of a π-Hybridized Tripodal Anchor while Maintaining Electronic Communication (2021)
  • Author(s): T. Ohto, A. Tashiro, T. Seo, N. Kawaguchi, Y. Numai, J. Tokumoto, S. Yamaguchi, R. Yamada, H. Tada, Y. Aso, Y. Ie
  • Journal Title: Small Volume: 17 Issue: 3 Pages: 2006709-2006709
  • DOI: 10.1002/smll.202006709
  • Peer Reviewed
• [Journal Article] Improving Intramolecular Hopping Charge Transport via Periodical Segmentation of π-Conjugation in a Molecule (2021)
  • Author(s): Y. Ie, Y. Okamoto, T. Inoue, T. Seo, T. Ohto, R. Yamada, H. Tada, Y. Aso
  • Journal Title: J. Am. Chem. Soc. Volume: 143 Issue: 2 Pages: 599-603
  • DOI: 10.1021/jacs.0c10560
  • Peer Reviewed / Open Access
• [Journal Article] Correlation between the Dipole Moment of Nonfullerene Acceptors and the Active Layer Morphology of Green-Solvent-Processed P3HT-Based Organic Solar Cells (2020)
  • Author(s): S. Chatterjee, T. Ohto, H. Tada, S. Jinnai, Y. Ie
  • Journal Title: ACS Sustainable Chem. Eng. Volume: 8 Issue: 51 Pages: 19013-19022
  • DOI: 10.1021/acssuschemeng.0c07114
  • Peer Reviewed / Open Access
• [Journal Article] The effect of a two-dimensional structure on the dielectric constant and photovoltaic characteristics (2020)
  • Author(s): K. Mishima, T. Sakai, K. Yokota, M. Taniguchi, Y. Aso, Y. Ie, K. Yamashita
  • Journal Title: J. Photochem. Photobiol. A Volume: 401 Pages: 112756-112756
  • DOI: 10.1016/j.jphotochem.2020.112756
  • Peer Reviewed
• [Presentation] スピロフルオレンを導入したシクロペンタチオフェンをπ共役リンカーとする非縮環型電子受容性分子の開発と波長選択型有機太陽電池への応用 (2024)
  • Author(s): 陣内 青萌、家 裕隆
  • Organizer: 日本化学会第104春季年会
• [Presentation] ジベンゾセキシチオフェンをコア骨格とした近赤外吸収特性をもつキノイド型オリゴチオフェンの合成と物性 (2024)
  • Author(s): 張 越、安藤 直紀、家 裕隆
  • Organizer: 日本化学会第104春季年会
• [Presentation] アルキル基修飾POSSの耐原子状酸素特性 (2024)
  • Author(s): 行松 和輝、横山 創一、後藤 亜希、丸山 幹人、木本 雄吾、家 裕隆
  • Organizer: 日本化学会第104春季年会
• [Presentation] ジベンゾクリセンを基盤とする3次元構造に拡張したπ電子系分子の開発 (2023)
  • Author(s): 森 宥貴、陣内 青萌、家 裕隆
  • Organizer: 第16回有機π電子系シンポジウム
• [Presentation] 5,5’-ビチアゾリリデン-4,4’-ジオン骨格を電子受容性ユニットとする近赤外吸収色素の合成と物性 (2023)
  • Author(s): 山田 澪奈、安藤 直紀、家 裕隆
  • Organizer: 第50回有機典型元素化学討論会
• [Presentation] 大きい電子分極率の実現に向けたジベンゾ[g,p]クリセンを中央ユニットとする3次元構造π共役化合物の開発 (2023)
  • Author(s): 森 宥貴、陣内 青萌、家 裕隆
  • Organizer: 第33回基礎有機化学討論会
• [Presentation] Green-light wavelength-selective organic solar cells for agrivoltaics (2023)
  • Author(s): Yutaka Ie
  • Organizer: 12th imec Handai International Symposium
  • Int'l Joint Research
• [Presentation] Green-light wavelength-selective organic solar cells for agrivoltaics (2023)
  • Author(s): Yutaka Ie
  • Organizer: Faraday Discussions
  • Int'l Joint Research
• [Presentation] Green-light wavelength-selective organic solar cells for agrivoltaics (2023)
  • Author(s): Yutaka Ie
  • Organizer: 243th ECS Meeting
  • Int'l Joint Research / Invited
• [Presentation] Development of Non-fused Nonfullerene Acceptors Bearing Spiro-Substituted Structures and Application to Green-light Wavelength-selective Organic Solar Cells for Agrivoltaics (2023)
  • Author(s): Yutaka Ie
  • Organizer: KJF International Conference
  • Int'l Joint Research / Invited
• [Presentation] Development of ladder-type pi-conjugated skeletons bearing spiro-substituted cyclopentadiaryl units for nonfullerene acceptors (2023)
  • Author(s): Kai Wang, Seihou Jinnai, Yutaka Ie
  • Organizer: KJF International Conference
  • Int'l Joint Research
• [Presentation] Green-light wavelength-selective organic solar cells toward agrivoltaics (2023)
  • Author(s): Seihou Jinnai, Taichi Moriyama, Mitsuharu Suzuki, Ken-ichi Nakayama, Yasuyuki Watanabe, Yutaka Ie
  • Organizer: 15th International Symposium on Functional pi-Electron Systems
  • Int'l Joint Research
• [Presentation] Development of Non-Fused Nonfullerene Acceptors Bearing Spiro-Substituted Structures and Application to Green-Light Wavelength-Selective Organic Solar Cells (2023)
  • Author(s): Yutaka Ie
  • Organizer: 11th East Asia Symposium on Functional Dyes and Advanced Materials
  • Int'l Joint Research / Invited
• [Presentation] Development of Ladder-Type Fused p-Conjugated Units Bearing Spirocyclopentadithiophenes for Non-Fullerene Acceptors in Organic Solar Cells (2023)
  • Author(s): Wang Kai, Takuji Seo, Hajime Nitta, Seihou Jinnai, Yutaka Ie
  • Organizer: 日本化学会第103春季年会
• [Presentation] 縮環構造をホッピングサイトとする長鎖分子ワイヤの開発 (2023)
  • Author(s): 淺川 亮、横山 創一、家 裕隆
  • Organizer: 日本化学会第103春季年会
• [Presentation] 5,5'-ビチアゾリリデン-4,4'-ジオン誘導体の物性と半導体特性評価 (2023)
  • Author(s): 山田 澪奈、安藤 直紀、家 裕隆
  • Organizer: 日本化学会第103春季年会
• [Presentation] エレクトロニクス機能を付与した有機π電子系の開発 (2022)
  • Author(s): 家 裕隆
  • Organizer: 第15回有機π電子系シンポジウム
  • Invited
• [Presentation] ドナー・アクセプター連結型有機光触媒の開発と分子変換反応への応用 (2022)
  • Author(s): 陣内 青萌、細田 靖、家 裕隆
  • Organizer: 第49回有機典型元素化学討論会
• [Presentation] フッ素置換ナフトビスチアジアゾール骨格を有するD-A型近赤外吸収色素の合成と物性並びに半導体特性評価 (2022)
  • Author(s): 宇都宮 桜、横山 創一、家 裕隆
  • Organizer: 第45回フッ素化学討論会
• [Presentation] 剛直かつ立体的に嵩高い構造が非フラーレン型アクセプターの太陽電池特性に与える影響 (2022)
  • Author(s): 陣内 青萌、村山 加純、永井 恵介、村岡 梓、山方 啓、佐伯 昭紀、小堀 康博、家 裕隆
  • Organizer: 第71回高分子討論会
• [Presentation] Functional pi-Conjugated Systems for Electronic Application (2022)
  • Author(s): Yutaka Ie
  • Organizer: 11th imec Handai International Symposium
  • Int'l Joint Research
• [Presentation] Development of Benzene-Annelated Quinoidal Systems for Acceptor Applications (2022)
  • Author(s): Yutaka Ie
  • Organizer: 241th ECS Meeting
  • Int'l Joint Research / Invited
• [Presentation] Development of Functional pi-Conjugated Molecules for Electronic Application (2022)
  • Author(s): Yutaka Ie
  • Organizer: KJF International Conference
  • Int'l Joint Research / Invited
• [Presentation] Development of Functional p-Conjugated Molecules Containing Cyclopentene-annelated Thiophene for Electronic Applications (2022)
  • Author(s): Yutaka Ie
  • Organizer: International Congress on Pure & Applied Chemistry
  • Int'l Joint Research / Invited
• [Presentation] Synthesis and physical properties of B-N fused nir-absorbing dyes with naphtobisthiadiazole unit toward organic semiconductor (2022)
  • Author(s): Sakura Utsunomiya, Soichi Yokoyama, Yutaka Ie
  • Organizer: The 25th SANKEN International Symposium
  • Int'l Joint Research
• [Presentation] Dipole Moment of Nonfullerene Acceptors: A Strategy for Green-Solvent Processed P3HT-Based Organic Solar Cells (2021)
  • Author(s): Yutaka Ie
  • Organizer: 239th ECS Meeting
  • Int'l Joint Research / Invited
• [Presentation] Nonfullerene Acceptors for Organic Solar Cells: Influence of Surface Free Energy and Dipole Moment on Film Morphologies (2021)
  • Author(s): Yutaka Ie
  • Organizer: The 11th International Conference on Flexible and Printed Electronics
  • Int'l Joint Research / Invited
• [Presentation] 精密分子設計に基づく有機太陽電池材料の開発 (2021)
  • Author(s): 家 裕隆
  • Organizer: 日本化学会第101春季年会
  • Invited
• [Presentation] ナフトビスチアジアゾ―ルを組み込んだ縮環型拡張π共役分子の合成と物性 (2021)
  • Author(s): 淺川 亮、横山 創一、家 裕隆
  • Organizer: 日本化学会第101春季年会
• [Presentation] Development of Nonfullerene Acceptors with Spiro-substituted Fluorene Units (2021)
  • Author(s): Keisuke Nagai, Takuji Seo, Seihou Jinnai, and Yutaka Ie
  • Organizer: 日本化学会第101春季年会
• [Presentation] 置換ナフトビスチアジアゾールを含む電子受容性分子の合成と有機太陽電池アクセプターへの応用 (2021)
  • Author(s): 大井 彩裕美、瀬尾 卓司、陣内 青萌、家 裕隆
  • Organizer: 日本化学会第101春季年会
• [Presentation] スピロフルオレン構造を有する電子受容性チオフェン系π共役オリゴマーの合成と有機太陽電池への応用 (2020)
  • Author(s): 陣内 青萌、瀬尾 卓司、家 裕隆
  • Organizer: 第47回有機典型元素化学討論会
• [Book] 有機半導体の開発と最新動向 (2023)
  • Author(s): 家 裕隆
  • Total Pages: 9
  • Publisher: シーエムシー出版
  • ISBN: 9784781317632