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Scale-up Chemical Synthesis of Thermally-activated Delayed Fluorescence Emitters Based on the Dibenzothiophene-S,S-Dioxide Core
Published on: October 24, 2017
Axially Chiral Biphenyl Compound-Based Thermally Activated Delayed Fluorescent Materials for High-Performance
Zhen-Long Tu1, Zhi-Ping Yan1, Xiao Liang1
1State Key Laboratory of Coordination Chemistry Collaborative Innovation Center of Advanced Microstructures Jiangsu Key Laboratory of Advanced Organic Materials School of Chemistry and Chemical Engineering Nanjing University Nanjing 210023 P. R. China.
Abstract:
To boost intrinsic circularly polarized luminescence (CPL) properties of chiral emitters, an axially chiral biphenyl unit is inlaid in thermally activated delayed fluorescent (TADF) skeleton, urging the participation of chiral source in frontier molecular orbital distributions. A pair of enantiomers, (R)-BPPOACZ and (S)-BPPOACZ, containing the cyano as electron-withdrawing moieties and carbazole and phenoxazine as electron-donating units are synthesized and separated. The circularly polarized TADF enantiomers exhibit both high photoluminescence quantum yield of 86.10% and excellent CPL activities with maximum dissymmetry factor |g PL| values of almost 10-2 in solution and 1.8 × 10-2 in doped film, which are among the best values of previously reported small chiral organic materials. Moreover, the circularly polarized organic light-emitting diodes based on the TADF enantiomers achieve the maximum external quantum efficiency of 16.6% with extremely low efficiency roll-off. Obvious circularly polarized electroluminescence signals with |g EL| values of 4 × 10-3 are also recorded.
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