Cooperative Aggregations of Nitrogen-Containing Perylene Diimides Driven by Rigid and Flexible Functional Groups

Shohei Kumagai; Hiroyuki Ishii; Go Watanabe; Tatsuro Annaka; Eiji Fukuzaki; Yukio Tani; Hiroki Sugiura; Tetsuya Watanabe; Tadanori Kurosawa; Jun Takeya; Toshihiro Okamoto

doi:10.1021/acs.chemmater.0c01888

journal article·2020-11-10

Cooperative Aggregations of Nitrogen-Containing Perylene Diimides Driven by Rigid and Flexible Functional Groups

Shohei Kumagai, Hiroyuki Ishii, Go Watanabe, Tatsuro Annaka, Eiji Fukuzaki, Yukio Tani, Hiroki Sugiura, Tetsuya Watanabe, Tadanori Kurosawa, Jun Takeya, Toshihiro Okamoto

Chemistry of Materials· Volume 32· Issue 21

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Source abstract

Abstract

Variation of aggregated structures driven by side chains is a crucial issue in organic semiconductors (OSCs) for achieving high carrier mobility and device durability. In this work, phenylalkyl side chains composed of a rigid terminal phenyl group and a flexible alkyl linker were studied based on a state-of-the-art n-type π-electron system, 3,4,9,10-benzo[de]isoquinolino[1,8-gh]quinolinetetracarboxylic diimide (BQQDI), from the viewpoints of aggregated structures and thin-film transistors. An appropriate length of the alkyl, i.e., propyl, linker led to stable formation of a unique aggregated structure regardless of solution-grown single-crystal and vacuum-deposited polycrystalline thin films likely due to cooperation of rigid phenyl and flexible alkyl moieties. In contrast, a shorter ethyl linker showed polymorphism in the polycrystalline film. An absence of polymorphism did not only result in high mobility and low threshold voltage but also show low contact resistance. Hence, this work proposes opportunities to design n-type OSCs by introduction of both rigid and flexible characters to the side chains.

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Research context

Electronic materials

OpenAlex topics: Organic Electronics and Photovoltaics · Molecular Junctions and Nanostructures · Force Microscopy Techniques and Applications

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Material Innovation Research Center (MIRC) and Department of Advanced Materials Science, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan

Department of Applied Physics, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan

Department of Physics, School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan

Fujifilm Corp., 577 Ushijima, Kaisei-machi, Ashigarakami-gun, Kanagawa 258-8577, Japan

National Institute of Advanced Industrial Science and Technology (AIST)-University of Tokyo Advanced Operando-Measurement Technology Open Innovation Laboratory (OPERANDO-OIL), AIST, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8561, Japan

MANA, National Institute for Materials Science (NIMS), 1-1 Namiki, Tsukuba 205-0044, Japan

PRESTO, JST, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan

Funding

Ministry of Education, Culture, Sports, Science and Technology

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