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Solution-processable ambipolar organic field-effect transistor based on Co-planar bisphthalocyaninato copper
Affiliation:1. Université de Perpignan Via Domitia, LAboratoire de Mathématiques et PhySique, 52 Avenue Paul Alduy, F-66860 Perpignan, France;2. J. Heyrovský Institute of Physical Chemistry, v.v.i., Academy of Sciences of the Czech Republic, Dolej?kova 3, 18223 Prague, Czech Republic;1. Institute of Physics, Bijeni?ka c. 46, P.O. Box 304, HR-10001 Zagreb, Croatia;2. National Physical Laboratory, Teddington, Middlesex TW11 0LW, United Kingdom;1. Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA;2. Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, USA;3. Athinoula A. Martinos Center for Biomedical Imaging, Department of Radiology, Massachusetts General Hospital, Harvard Medical School, Charlestown, MA 02129, USA;1. MOE Key Laboratory of Macromolecular Synthesis and Functionalization, State Key Laboratory of Silicon Materials and Department of Polymer Science and Engineering, Zhejiang University, Hangzhou 310027, PR China;2. Department of Materials Science and Engineering, University of California, Los Angeles, CA 90095, USA;3. Department of Chemistry, Zhejiang University, Hangzhou 310027, PR China;1. Department of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China;2. College of Chemical Engineering and Environmental Chemistry, Weifang University, Weifang 261061, China;1. Institute of Chemistry, Vietnam Academy of Science and Technology, 18 Hoang Quoc Viet, Cau Giay, Hanoi, Viet Nam;2. Department of Chemistry, Research Institute for Natural Sciences, Korea University, Seoul 136-701, South Korea
Abstract:A soluble binuclear phthalocyaninato copper (II) complex, Cu2Pc(COOC8H17)6]2 (1), with planar molecular structure and extended conjugation system, has been designed and synthesized. By fusing two phthalocyanine rings side by side and introducing electron withdrawing groups at periphery positions, the energy levels of HOMO and LUMO have been tuned successfully into the range of an air-stable ambipolar organic semiconductor required as revealed by the electrochemical studies. With the help of a solution-based quasi-Langmuir–Shäfer (QLS) method, thin solid films of this compound were fabricated and organic field effect transistors (OFETs) based on these QLS thin solid films were constructed. Because of the promising electrochemical properties as well as the high ordered packing structure of the molecules in the thin solid films, the OFETs performed excellent ambipolar operating properties, with the electron and hole mobility in air as high as 1.7 × 10?1 and 2.3 × 10?4 cm2 V?1 s?1, respectively. For comparison purpose, mononuclear compound CuPc(COOC8H17)8] (2) was comparatively studied. The QLS thin solid films of this compound possess similar ordered structure with that of Cu2Pc(COOC8H17)6]2 (1), but the OFETs based on the thin solid films of this compound can only show n-type properties under nitrogen atmosphere with an extremely small electron mobility of 1.6 × 10?4 cm2 V?1 s?1. This result suggests that extension on the conjugation system of an aromatic compound with multiple electron withdrawing groups can tune the molecule into an air stable ambipolar organic semiconductor.
Keywords:Ambipolar  OFET  Bisphthalocyanine  Co-planar
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