A novel carbazole based bismaleimide monomer: Synthesis, characterization, thermal and optical properties

Abstract

In this study, a novel bismaleimide monomer: Carbazole-Bismaleimide (Cz-BisMI) was introduced to the literature as a first. Cz-BisMI was synthesized by a catalytic cyclodehydration reaction of 3,6-bismalemic acid carbazole which is an intermediate product obtained by an imidization reaction of 3,6-diamino carbazole. Then, the chemical structure of Cz-BisMI was elucidated by FT-IR, 1H NMR, 13C NMR and LC-MS spectroscopies. The thermal properties of Cz-BisMI were investigated by DSC in comparison with a commercial bismaleimide monomer, 4,4-bismaleimidophenylmethane (DPM-BisMI). Cz-BisMI has a melting point of 192°C and also, the onset temperature of the exothermic curve was measured as 293°C. Furthermore, it was determined that Cz-BisMI has a 35.6 percent larger processing window than DPM-BisMI. The spin-coated films of Cz-BisMI showed a high refractive index in the range of 1.61 to 1.50 between 400 and 650 nm with good transparency of over 85%. On the other hand, a new poly(bismaleimide): P(Cz-BisMI)s containing carbazole units was prepared by the self-polymerization process of Cz-BisMI. P(Cz-BisMI)s showed a high thermal transition temperature of 356°C. In conclusion, Cz-BisMI is a viable choice as a bismaleimide monomer for the development of opto-electronic materials due to its enhanced optical properties and thermal behavior.