Alkylated selenophene-based ladder-type monomers via a facile route for high performance thin-film transistor applications

We report the synthesis of two new selenophene containing ladder-type monomers, cyclopentadiselenophene (CDS) and indacenodiselenophene (IDSe), via a twofold and fourfold Pd catalyzed coupling with a 1,1-diborylmethane derivative. Co-polymers with benzothiadiazole (BT) were prepared in high yield by Suzuki polymerization to afford co-polymers which exhibited excellent solubility in a range of non-chlorinated solvents. The CDS co-polymer exhibited a band gap of just 1.18 eV, which is amongst the lowest reported for donor-acceptor polymers. Thin-film transistors were fabricated using environmentally benign, non-chlorinated solvents with the CDS and IDSe co-polymers exhibiting hole mobility up to 0.15 and 6.4 cm2 /Vs, respectively. This high performance was achieved without the undesirable peak in mobility often observed at low gate voltages due to parasitic contact resistance.