Dianthracenylazatrioxa[8]circulene: synthesis, characterization and application in OLEDs

A soluble and green-blue fluorescent π-extended azatrioxa[8]circulene was synthesized by oxidative condensation of a 3,6-dihydroxycarbazole and 1,4-anthraquinone utilizing benzofuran scaffolding. This is the first circulene to incorporate anthracene within it carbon framework. Solvent-dependent fluorescence and bright green electroluminescence accompanied by excimer emission are key optical properties of this material. The presence of sliding π-stacked columns in the single crystal of dianthracenylazatrioxa[8]circulene is found to cause a very high rate for the electron hopping making this material a promising n-type organic semiconductor with an electron mobility predicted around 2.26 cm 2 V -1 s -1 . The best OLED device based on the dianthracenylazatrioxa[8]circulene fluorescent emitter has a brightness around 16 000 Cd m -2 and external quantum efficiency of 3.3%. By using dianthracenylazatrioxa[8]circulene as a host matrix material the quantum dots based OLEDs were fabricated.