American Chemical Society
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New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics

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journal contribution
posted on 2017-09-15, 16:39 authored by Thomas Bura, Serge Beaupré, Olzhas A. Ibraikulov, Marc-André Légaré, Jesse Quinn, Patrick Lévêque, Thomas Heiser, Yuning Li, Nicolas Leclerc, Mario Leclerc
Diketopyrrolopyrrole (DPP) derivatives are among the most efficient materials studied for both polymer solar cells (PSCs) and organic field-effect transistors (OFETs) applications. We report here the synthesis of new fluorinated dithienyl­diketo­pyrrolopyrrole (fDT-DPP) monomers suitable for direct heteroarylation polymerization. fDT-DPP copolymers were then prepared to probe the effect of the fluorination. It was found that they feature deeper HOMO energy levels and smaller bandgaps than their non-fluorinated analogues. Moreover, some fDT-DPP copolymers show ambipolar behavior when tested in OFETs. For example, P2 shows hole mobility up to 0.8 cm2 V–1 s–1 and electron mobility up to 0.5 cm2 V–1 s–1. Inverted PSCs with power conversion efficiency (PCE) up to 7.5% were also obtained for P5. These results reported here (OFETs and PSCs) confirm that the fluorination of dithienyl-DPP moieties improves the performance of organic electronics devices. This study is also evidencing the strength of the direct heteroarylation polymerization and fDT-DPP as a new class of conjugated polymers.