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

Molecules. 2020 Jan 21;25(3):445. doi: 10.3390/molecules25030445.

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: acridan; aggregation induced emission enhancement; electroluminescence.; tetra-/triphenylethene.

MeSH terms

  • Acridones / chemical synthesis
  • Acridones / chemistry*
  • Calorimetry, Differential Scanning
  • Electricity
  • Electrochemistry
  • Furans / chemistry
  • Luminescence*
  • Spectrophotometry, Ultraviolet
  • Temperature
  • Toluene / chemistry

Substances

  • Acridones
  • Furans
  • Toluene
  • tetrahydrofuran