Synthesis and characterization of fluorene and carbazole dithienosilole derivatives for potential applications in organic light-emitting diodes

Abstract

Several fluorene or carbazole-based dithienosiloles (DTSs) have been synthesized and their thermal, photophysical, and electrochemical properties have been systematically investigated. These compounds show high thermal stability with glass transition temperature above 110 °C as well as decomposition temperatures at ∼400 °C. Intense green emission is observed in the spectral region of 500–510 nm for all compounds (ΦPL=0.31–0.80), that is, attributed to both the 5,5′-substituents of the DTS ring and DTS-based π–π∗ transition. Based on the emission spectra at 77 K, the triplet energy for these compounds was calculated to be within 2.1–2.2 eV, indicating that they may be used as host materials for red emitters in organic light-emitting diodes (OLEDs). All compounds exhibit reversible oxidation and possess low-lying LUMO energies, owing to the conjugated fluorene/carbazole substituents on the DTS. This along with the high thermal/electrochemical stabilities and high fluorescent quantum efficiencies makes the new DTSs compounds promising candidates for use in OLEDs as emitters, host and electron-transporting materials.