Solution-processed deep-blue (y∼0.06) fluorophores based on triphenylamine-imidazole (donor-acceptor) for OLEDs: computational and experimental exploration

Abstract

Developing solution-processable deep-blue emitters for organic light-emitting diodes (OLEDs) is still a challenging task. In this context, two new solution-processable deep-blue emitters, N, N-diphenyl-4’-(1-(3-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)-[1,1’-biphenyl]-4-amine(4-PIMCFTPA) and 4’-(4,5-diphenyl-1-(3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)-N,N-diphenyl-[1,1’-biphenyl]-4-amine (4-BICFTPA), were successfully designed and synthesized by incorporating phenanthroimidazole (PI)/diphenylimidazole (BI)-triphenylamine (TPA), which is functional at the N1 position of the imidazole, with Ph-mCF3. The thermal, photophysical, and electrochemical properties of both fluorophores were systematically explored. These fluorophores showed a deep-blue emission in the solution as well as in the solid state. The highest occupied molecular orbital (HOMO) – lowest unoccupied molecular orbital (LUMO) energy level of the fluorophores was calculated using electrochemical studies and compared with the theoretical calculation [the density functional theory (DFT)]. The asymmetrically twisted conformation of 4-PIMCFTPA between PI-TPA efficiently showed a high photoluminescence quantum yield. OLED (undoped and doped) devices were fabricated with the newly synthesized emitters, and 4-PIMCFTPA demonstrated better electroluminescence (EL) performance than the BI-based emitter. Thus, the OLED based on 4-PIMCFTPA (1 wt% in the CBP host) had the best EL performance, with a maximum external quantum efficiency 1.7% and CIE coordinates of (0.17, 0.06).

Keywords

• blue fluorophores
• phenanthroimidazole
• oled
• organic electronics