Synthesis, characterization and DFT study of new anthracene-based semiconducting polyethers for OLED application

New soluble semiconducting anthracene-based polyethers (An-BPS and An-TDP) were synthetized via the Williamson polycondensation of 9,10-dichloromethylanthracene with 4,4'-thiodiphenol (TDP) and bisphenol S (BPS), respectively. The polymers were investigated by density functional theory (DFT): the structural and optoelectronic properties, frontier molecular orbitals (HOMO/LUMO), as well as the infrared, absorption and fluorescence spectra were discussed. The polyethers structures were confirmed by NMR and FTIR spectroscopies, revealing good agreements between experimental and theoretical results. Quasiidentical absorption and blue emission properties were obtained for both polymers in dilute solutions, with a higher fluorescence efficiency for An-BPS. The cyclic voltammetry analysis of these electrochemically active materials showed a higher electron affinity for An-BPS and a lower ionization potential for An-TDP. The DFT calculations showed that the HOMO/LUMO frontier energy distributions are confined on the anthracene moiety in An-BPS. However in An-TDP, the LUMO distribution is localized on anthracene group, while the HOMO is on the TDP unit. The electric behavior of organic light-emitting diodes (OLEDs) based on these macromolecular structures has been investigated via numerical simulation using Silvaco TECAD software. Good electrical properties are estimated, with a low turn on voltages of 3.1 V and 2.9 V for An-TDP and An-BPS, respectively. However, An-BPS showed improved current conductivity, which makes it a good candidate for OLEDs. (C) 2021 Elsevier B.V. All rights reserved.