An Organic Borate Salt with Superior <i>p</i>‐Doping Capability for Organic Semiconductors

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  • Berthold Wegner
    Institut für Physik and IRIS Adlershof Humboldt‐Universität zu Berlin Berlin D‐12489 Germany
  • Dominique Lungwitz
    Institut für Physik and IRIS Adlershof Humboldt‐Universität zu Berlin Berlin D‐12489 Germany
  • Ahmed E. Mansour
    Institut für Physik and IRIS Adlershof Humboldt‐Universität zu Berlin Berlin D‐12489 Germany
  • Claudia E. Tait
    Berlin Joint EPR Lab Fachbereich Physik Freie Universität Berlin Berlin D‐14195 Germany
  • Naoki Tanaka
    Laboratory for Chemistry and Life Science Institute of Innovative Research Tokyo Institute of Technology Yokohama 226‐8503 Japan
  • Tianshu Zhai
    Institute of Functional Nano and Soft Materials (FUNSOM) Jiangsu Key Laboratory for Carbon‐Based Functional Materials and Devices and Joint International Research Laboratory of Carbon‐Based Functional Materials and Devices Soochow University Suzhou 215123 P. R. China
  • Steffen Duhm
    Institute of Functional Nano and Soft Materials (FUNSOM) Jiangsu Key Laboratory for Carbon‐Based Functional Materials and Devices and Joint International Research Laboratory of Carbon‐Based Functional Materials and Devices Soochow University Suzhou 215123 P. R. China
  • Michael Forster
    Makromolekulare Chemie and Institut für Polymertechnologie Bergische Universität Wuppertal Wuppertal D‐42097 Germany
  • Jan Behrends
    Berlin Joint EPR Lab Fachbereich Physik Freie Universität Berlin Berlin D‐14195 Germany
  • Yoshiaki Shoji
    Laboratory for Chemistry and Life Science Institute of Innovative Research Tokyo Institute of Technology Yokohama 226‐8503 Japan
  • Andreas Opitz
    Institut für Physik and IRIS Adlershof Humboldt‐Universität zu Berlin Berlin D‐12489 Germany
  • Ullrich Scherf
    Makromolekulare Chemie and Institut für Polymertechnologie Bergische Universität Wuppertal Wuppertal D‐42097 Germany
  • Emil J. W. List‐Kratochvil
    Institut für Physik and IRIS Adlershof Humboldt‐Universität zu Berlin Berlin D‐12489 Germany
  • Takanori Fukushima
    Laboratory for Chemistry and Life Science Institute of Innovative Research Tokyo Institute of Technology Yokohama 226‐8503 Japan
  • Norbert Koch
    Institut für Physik and IRIS Adlershof Humboldt‐Universität zu Berlin Berlin D‐12489 Germany

説明

<jats:title>Abstract</jats:title><jats:p>Molecular doping allows enhancement and precise control of electrical properties of organic semiconductors, and is thus of central technological relevance for organic (opto‐) electronics. Beyond single‐component molecular electron acceptors and donors, organic salts have recently emerged as a promising class of dopants. However, the pertinent fundamental understanding of doping mechanisms and doping capabilities is limited. Here, the unique capabilities of the salt consisting of a borinium cation (Mes<jats:sub>2</jats:sub>B<jats:sup>+</jats:sup>; Mes: mesitylene) and the tetrakis(penta‐fluorophenyl)borate anion [B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>4</jats:sub>]<jats:sup>−</jats:sup> is demonstrated as p‐type dopant for polymer semiconductors. With a range of experimental methods, the doping mechanism is identified to comprise electron transfer from the polymer to Mes<jats:sub>2</jats:sub>B<jats:sup>+</jats:sup>, and the positive charge on the polymer is stabilized by [B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>4</jats:sub>]<jats:sup>−</jats:sup>. Notably, the former salt cation leaves during processing and is not present in films. The anion [B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>4</jats:sub>]<jats:sup>−</jats:sup> even enables the stabilization of polarons and bipolarons in poly(3‐hexylthiophene), not yet achieved with other molecular dopants. From doping studies with high ionization energy polymer semiconductors, the effective electron affinity of Mes<jats:sub>2</jats:sub>B<jats:sup>+</jats:sup>[B(C<jats:sub>6</jats:sub>F<jats:sub>5</jats:sub>)<jats:sub>4</jats:sub>]<jats:sup>−</jats:sup> is estimated to be an impressive 5.9 eV. This significantly extends the parameter space for doping of polymer semiconductors.</jats:p>

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