Development of Intramolecular Exciton-Coupled Bis-Squaraine Dyes for Application to Near-Infrared Organic Photodetectors

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  • SAWADA Ryuhei
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University
  • HAMA Reiji
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University
  • KINOSHITA Saki
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University
  • MAEDA Takeshi
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University
  • SUZUKI Naoya
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University
  • YAGI Shigeyuki
    Department of Applied Chemistry, Graduate School of Engineering, Osaka Metropolitan University

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  • 近赤外有機光検出器への応用を指向した分子内励起子相互作用を示すビススクアレン色素の開発

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Abstract

<p>We synthesized two bis-squaraine dyes consisting of benzo[1,2-b:5,4-b’]dipyrrole central components and indolenine-based semisquaraine or its dicyanovinylene analogue for application to electron donor materials for organic photodetectors with bulk heterojunction architecture. These dyes exhibited split electronic absorption bands attributed to intramolecular exciton coupling. The lower energy absorption band of the bis-squaraine dye with dicyanovinylene group was observed in the near-infrared region. In cyclic voltammograms of bis-squaraine dyes, broad redox waves were observed in oxidative scans, indicating that one-electron oxidized dyes have delocalized electronic states throughout two chromophores. The highest occupied molecular orbitals and the lowest unoccupied molecular orbitals of bis-squaraine dyes have suitable energy levels for electron donor materials toward the fullerene-based electron acceptor. A composite film comprised of a fullerene acceptor and a bis-squaraine dye showing near-infrared absorption exhibited a near infrared absorption with a maximum at ca. 780 nm, promising photo-induced electron transfer upon the irradiation of near infrared light. An organic photodetector with the composite film demonstrated a specific detectivity (D＊) of 4.6×1011 Jones under 750 nm illumination and 3.3×1011 Jones under 800 nm illumination. This indicated that the bis-squaraine dye can work as the donor material in organic photodetectors responsive to near-infrared light.</p>

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