Naphthalene Diimide-Based Polymeric Semiconductors. Effect of Chlorine Incorporation and N-Channel Transistors Operating in Water

Abstract

We demonstrate here the design, synthesis and characterization of two new chlorinated polymers, P(NDI2HD-T2Cl2) and P(NDI2OD-T2Cl2) based on N,N-difunctionalized naphthalene diimide (NDI) and 3,3-dichloro-2,2-bithiophene (T2Cl2) moieties. Our results indicate that organic thin-film transistors (OTFTs) based on these new chlorinated polymers exhibit electron mobilities approaching 0.1 cm(2)V(-1)s(-1) (I-on:I-off similar to 10(6)-10(7)), with far less ambipolarity due to their lower highest occupied molecular orbital energies, and they are more stable under deleterious high-humidity conditions (RH similar to 60%) and upon submersion in water, compared with those fabricated with the parent non-chlorinated polymers. In addition, OTFTs fabricated with the new chlorinated polymers exhibit excellent operational stabilities with <3% degradations upon bias-stress test.