Organic light emitting diodes (OLEDs) offer several advantages to their inorganic counterparts including tunable energy levels, solution processability and the ability to be fabricated on flexible substrates. In spite of the remarkable progress, the performance of blue OLEDs has been plagued by the overwhelming problem of aggregation of the polymers and oxidative stability of wide band gap materials in both neat and host-guest systems. We have designed new emissive materials based on cross-conjugated benzobisoxazole cores that allows for fine-tuning of the HOMO and LUMO levels. We have also incorporated arenes with various levels of steric hindrance to reduce the aggregation within these systems. By implementing these strategies into our emitters, we have developed wide band gap materials that exhibit efficient emission in the blue region. When utilized in OLEDs via host-guest, and neat architectures, one example, tetrafluorene-benzobisoxazole reached a peak brightness of 1649 Cd/m2 and current efficiency of 1.93 Cd/A as a blue emitter at 450 nm. This is higher that that seen for a related polymeric system.