Triplet-Energy Control of Polycyclic Aromatic Hydrocarbons by BN Replacement: Development of Ambipolar Host Materials for Phosphorescent Organic Light-Emitting Diodes

Abstract

In this work, we achieved the triplet-energy control of polycyclic aromatic hydrocarbons (PAHs) by replacing the Carbon−Carbon (CC) unit with a Boron−Nitrogen (BN) unit. Time-dependent density functional theory calculations suggested that the insertion of the BN unit may cause localization of the singly occupied molecular orbitals 1 and 2 (SOMO1/SOMO2) in the triplet state, which in turn can reduce the exchange interaction and dramatically increase the high singlet–triplet excitation energy (ET). The PAH containing the BN unit, 4b-aza-12b-boradibenzo[g,p]chrysene, showed a large ET value and ambipolar carrier-transport abilities. The introduction of a phenyl substituent on 4b-aza-12b-boradibenzo[g,p]chrysene slightly reduced the ET values and the carrier-transport abilities, but increased the glass-transition temperatures. On the basis of these findings, we successfully built phosphorescent organic light-emitting diodes using the BN compounds as host materials, which exhibit a superior performance over the device using a representative host material, 4,4′-bis(N-carbazolyl)-1,1′-biphenyl, not only in terms of efficiency but also in terms of device lifetime. This study demonstrated the potential of BN-embedded polycyclic aromatics in organic electronics and showed a novel strategy to achieve triplet-energy control of aromatic compounds.