New Fluorinated Dithienyldiketopyrrolopyrrole Monomers and Polymers for Organic Electronics

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.