Synthesis and electronic properties of novel symmetric spirosilabifluorene derivatives

ORGN 171

Sang Ho Lee and Zakya H. Kafafi. Optical Sciences Division, US Naval Research Laboratory, 4555 Overlook Ave, SW, Washington, DC 20375
Silacyclopentadiene (silole) derivatives are promising p-conjugated materials for use in electro-optic devices such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs) due to their high solid state fluorescence quantum yields and excellent electron transporting properties. Recently, we have reported on the synthesis and electronic properties of asymmetrically substituted spirosilafluorene derivatives containing either electron withdrawing or donating substituents. These derivatives have exhibited excellent thermal and morphological stabilities (Tgs; 205 to 230 °C) that are far superior to corresponding silole analogues (Tg; 77 °C). Here we report the synthesis of symmetrically substituted spirosilabifluorene derivatives via the cyclization of dilithio biphenyls with silicon tetrachloride. The electronic and optical properties of these compounds, and their incorporation into OLEDs as electro- and photo-active materials (either light-emitting or electron transporting materials) will be discussed.