Synthesis and Late-Stage Diversification of BN-Embedded Dibenzocorannulenes as Efficient Fluorescence Organic Light-Emitting Diode Emitters

We report the synthesis and late-stage diversification of a new class of hetero-buckybowl, BN-embedded dibenzocorannulenes (B2N2-DBCs). The synthesis is achieved via one-shot halogenative borylation, comprising the nitrogen-directed haloboration of alkyne and an intramolecular bora-Friedel-Crafts reaction, which provides BN-embedded dibenzocorannulene possessing two bromo substituents (B2N2-DBC-Br). B2N2-DBC-Br undergoes diversification via coupling reactions to provide a variety of arylated derivatives (B2N2-DBC-R), exhibiting strong blue fluorescence. An organic light-emitting diode (OLED) employing one of the derivatives as an emitter exhibited a high external quantum efficiency of 6.6 % and long operational lifetime of 907 h at an initial luminance of 1000 cd m(-2), indicating the significant potential for the development of efficient and stable hetero-buckybowl-based OLED materials.