Synthesis of π-Conjugated Polymers Containing Benzotriazole Units via Palladium-Catalyzed Direct C-H Cross-Coupling Polycondensation for OLEDs Applications

Abstract

Four D-π-A conjugated polymers, namely P1–P4, which contain benzotriazole building blocks in their backbone as acceptor, are synthesized via palladium-catalyzed direct C-H cross-coupling polycondensation of 5,6-difluorobenzotriazole with different thiophene derivatives, including 3-octylthiophene, 2,2’-bithiophene, thieno[3,4-b][1,4]dioxine, and 4,4-dioctyl-4H-silolo-[3,2-b:4,5-b’]dithiophene as donor units, respectively. Taking the polymer P1 as an example, the chemical structure of the polymer is demonstrated by 1H and 19F NMR spectra. The optical, electrochemical, and thermal properties of these polymers are assessed by UV–vis absorption and fluorescence spectroscopy, cyclic voltammetry (CV), and thermal gravimetric analysis (TGA), respectively. DFT simulations of all polymers are also performed to understand their physicochemical properties. Furthermore, P1 and P2, which have relatively higher molecular weights and better fluorescent quantum efficiency than those of P3 and P4, are utilized as lighting emitters for organic light-emitting diodes (OLEDs), affording promising green and red luminescence with 0.07% and 0.14% of maximum external quantum efficiency, respectively, based on a device with an architecture of ITO/PEDOT:PSS/PTAA/the polymer emitting layer/TPBi/LiF/Al.