A new series of short axially symmetrically and asymmetrically 1,3,6,8-tetrasubstituted pyrenes with two types of substituents: Syntheses, structures, photophysical properties and electroluminescence

Abstract

A new series of short axially symmetrically (4a and 4b) and asymmetrically (4c and 4d) 1,3,6,8-tetrasubstituted pyrene-based compounds with two phenyl moieties and two diphenylamine units on the pyrene core were designed and synthesized based on stepwise synthetic strategy. These compounds were structurally characterized and their photoelectric properties were investigated by spectroscopy, electrochemical and theoretical studies. The structures of 4a and 4b were determined by single-crystal X-ray diffraction analysis, indicating that the compounds are twisted by the peripheral substituents and the intermolecular π-π interactions have been efficiently interrupted. The four compounds exhibit high absolute fluorescence quantum yields (ФF) in dichloromethane (83.31–88.45%) and moderate ФFs in film states (20.78–38.68%). In addition, compounds 4a and 4b display relatively higher absolute ФFs than those of 4c and 4d in film states. All the compounds exhibit high thermal stability with decomposition temperatures above 358 °C and the values of 4c and 4d are higher than 4a and 4b. Compounds 4a and 4b can form morphologically stable amorphous thin films with Tg values of 146 °C and 149 °C, respectively. However, there are no obvious Tg observed in compounds 4c and 4d. Electroluminescent devices using 4a and 4b as doped emission layer show promising device performance with low turn-on voltage (3.0 V), maximum brightness around 15100 cd/m2 and 16100 cd/m2, maximum luminance efficiency of 12.4 cd/A and 13.6 cd/A and maximum external quantum efficiency of 5.34% and 5.63%, respectively.