Abstract
Three conjugated triphenylamine-based poly(azomethine)s were prepared via well-known polycondensation chemistry using cheap and readily available starting materials and the results were contrasted with rrP3HT. Three functionalized diaminetriphenylamines (TPA(X), X ¼ –H, –OMe, –CN) were polymerized in a simple one-step process with 2,3-dihydrothieno[3,4-b][1,4]dioxine-5,7-dicarbaldehyde (ThOx), with water being the only side product. The resulting polymers (TPA(X)ThOx, X ¼ –H, –OMe, –CN) were characterized by GPC, IR and NMR, and show a good thermal stability. The opto-electronic properties could be tuned by changing the functionalization (X ¼ –H, –OMe, –CN) on the triphenylamine moiety. Photovoltaic devices based on TPA(X)ThOx/PCBM (1 : 2) showed power conversion efficiencies in the range of 0.02–0.04%. TRMC measurements showed that the presence of PCBM as an electron acceptor facilitates the formation of free mobile charges after excitation of the polymer. The low device efficiencies are attributed to a low hole-mobility of the polymer in combination with poor active layer morphology.
Highlights
In this paper we will present our efforts in exploring azomethine-based condensation polymers for photovoltaic applications
Solar cells were prepared by covering pre-cleaned ITO patterned glass substrates with PEDOT:PSS (Clevios P, VP Al4083)
The low efficiencies were explained by the low hole mobility of the polymer in combination with a poor morphology of the active layer
Summary
In this paper we will present our efforts in exploring azomethine-based condensation polymers for photovoltaic applications. In the last few years, a wide range of (record breaking) small bandgap hole-transporting polymers have been developed, mostly synthesized via Suzuki and Wittig type reactions. These chemistries, make use of expensive metal catalysts, require inert reaction conditions, and need substantial product puri cation to obtain the polymers in the required purity, making large-scale application limited if not altogether impossible. E-mail: t.j.dingemans@tudel .nl bDutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands cOptoelectronic Materials Section, Department of Chemical Engineering, Del University of Technology, 2628 BL Del , The Netherlands dUniversity of Cambridge, Optoelectronics Group, Cavendish Laboratory, J.J. Thomson Avenue, Cambridge, CB3 0HE, UK eLaboratory for Chemistry of Novel Materials, University of Mons, Place du Parc 20, 7000 Mons, Belgium been applied, to some extent successfully, as hole transporting materials in organic solar cells by this group and others.. Thomson Avenue, Cambridge, CB3 0HE, UK eLaboratory for Chemistry of Novel Materials, University of Mons, Place du Parc 20, 7000 Mons, Belgium been applied, to some extent successfully, as hole transporting materials in organic solar cells by this group and others. The azomethine bond is isoelectronic with its vinyl analogue, its synthesis is more advantageous as water is the only by-product and (expensive) catalysts are not required
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