Novel Luminescent Benzimidazole-Substituent Tris(2,4,6-trichlorophenyl)methyl Radicals: Photophysics, Stability, and Highly Efficient Red-Orange Electroluminescence

Abstract

Luminescent radicals have various applications because they simultaneously possess optoelectronic, electronic, and magnetic properties. Despite the development of some luminescent tris(2,4,6-trichlorophenyl)methyl (TTM)-based radicals, all the substituents directly attached to the TTM skeleton are electron-donating groups. Herein, the electron-withdrawing group is first attached to a p carbon of the parent TTM radical, and two novel stable open-shell adducts based on the benzimidazole unit with red-orange emission are obtained. Their photophysical properties, photochemical stabilities, and electroluminescent performances are fully investigated. Because of the introduction of the benzimidazole unit, the intramolecular charge transfer property of D–A type molecules is suppressed to a large extent, and the delocalization of the sole electron is strengthened. Both radicals exhibit largely improved photostability compared to that of the TTM core. High PL quantum yields (Φ F ) of 0.39 and 0.36 in doped films are achieved, which are among the highest values for luminescent radicals. Extremely high-voltage-durable characteristic is demonstrated in the organic light-emitting diodes utilizing them as emitters. One device has a maximal external quantum efficiency that even exceeds the classical theoretical upper limit of 5%.