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The development of a one-step borylation of 1,3-diaryloxybenzenes, yielding novel boron-containing polycyclic aromatic compounds, is reported. The resulting boron-containing compounds possess high singlet-triplet excitation energies as a result of localized frontier molecular orbitals induced by boron and oxygen. Using these compounds as a host material, we successfully prepared phosphorescent organic light-emitting diodes exhibiting high efficiency and adequate lifetimes. Moreover, using the present one-step borylation, we succeeded in the synthesis of an efficient, thermally activated delayed fluorescence emitter and boron-fused benzo[6]helicene. [ABSTRACT FROM AUTHOR]

The triplet-energy control of polycyclic aromatic hydrocarbons (PAHs) was achieved by heteroatom incorporation. For instance, 4b-aza-12b-boradibenzo[g,p]chrysene showed a much larger ET value than the corresponding PAH, dibenzo[g,p]chrysene, and enable us to built phosphorescent organic light-emitting diodes (PHOLEDs) of high performance. We have also synthesized a variety of heteroatom-incorporated polycyclic aromatics with a large ET value, which improved not only efficiency of PHOLED but also lifetime. [ABSTRACT FROM AUTHOR]