Towards Blue AIE/AIEE: Synthesis and Applications in OLEDs of Tetra-/Triphenylethenyl Substituted 9,9-Dimethylacridine Derivatives

Abstract

Aiming to design blue fluorescent emitters with high photoluminescence quantum yields in solid-state, nitrogen-containing heteroaromatic 9,9-dimethylacridine was refined by tetraphenylethene and triphenylethene. Six tetra-/triphenylethene-substituted 9,9-dimethylacridines were synthesized by the Buchwald-Hartwig method with relatively high yields. Showing effects of substitution patterns, all emitters demonstrated high fluorescence quantum yields of 26−53% in non-doped films and 52−88% in doped films due to the aggregation induced/enhanced emission (AIE/AIEE) phenomena. In solid-state, the emitters emitted blue (451−481 nm) without doping and deep-blue (438−445 nm) with doping while greenish-yellow emission was detected for two compounds with additionally attached cyano-groups. The ionization potentials of the derivatives were found to be in the relatively wide range of 5.43−5.81 eV since cyano-groups were used in their design. Possible applications of the emitters were demonstrated in non-doped and doped organic light-emitting diodes with up to 2.3 % external quantum efficiencies for simple fluorescent devices. In the best case, deep-blue electroluminescence with chromaticity coordinates of (0.16, 0.10) was close to blue color standard (0.14, 0.08) of the National Television System Committee.

Keywords

• tetra-/triphenylethene
• acridan
• aggregation induced emission enhancement
• electroluminescence