Synthesis and properties of hole-transporting indolo[3,2-b]carbazole-based hydrazones with reactive functional groups

The synthesis of indolo[3,2-b]carbazole-based mono- and dihydrazones with reactive vinylbenzyl or vinyloxyethyl functional groups at the nitrogen atom of hydrazine moiety is reported. The thermal, optical, photophysical, electrochemical and photoelectrical properties of the synthesized compounds are described. They exhibit moderate thermal stability with 5% weight loss temperatures ranging from 273 to 343 °C. Self-polymerization of the monomers with vinylbenzyl functional groups starts at around 180 °C. The values of ionization potentials of the compounds measured by cyclic voltammetry are in the range of 4.94-5.00 eV and those estimated by electron photoemission in air range from 4.99 to 5.21 eV. Electron affinities range from −2.28 to −2.23 eV. The molecular structure of these hydrazones allows stable amorphous films to be prepared and the hole drift mobilities of the films exceed 10−3 cm2/V s at high electric fields.

Graphical abstractDownload high-res image (115KB)Download full-size image