New 4,4′-Bis(9-carbazolyl)–Biphenyl Derivatives with Locked Carbazole–Biphenyl Junctions: High-Triplet State Energy Materials

We synthesized a series of 4,4′-bis­(9-carbazolyl)–biphenyl (CBP) derivatives, using methyl groups as spatially demanding groups, locking the angle between the carbazole subunit and the biphenyl backbone as potential matrix material for blue organic light-emitting diodes (OLEDs). The locked rotation was achieved by four methyl groups either in positions 1 and 8 of the carbazole subunit (1) or in positions 3, 5, 3′, and 5′ of the biphenyl subunit (2), and the fixed spatial arrangement was confirmed by X-ray analysis. The physical properties of CBP derivatives based on parent structure 2 were further tailored by electron-withdrawing CF3 groups in positions 3 and 6 (3) or positions 2 and 7 of the carbazole subunits (4) or alternatively by electron-donating CH3O groups in positions 2 and 7 (5) of the same building blocks. Increased triplet energies (E T) compared to that of the parent compound CBP were found for all synthesized CBP derivatives 1–5. Enhanced glass transition temperatures ranging between 129 and 202 °C further corroborate the application potential of these derivatives for matrix material in blue OLEDs.