Pyrene-Benzimidazole Derivatives as Novel Blue Emitters for OLEDs

• Published in: Molecules (Basel, Switzerland) Vol. 26; no. 21; p. 6523
• Main Authors: De Silva, Thenahandi Prasanthi Deepthika, Youm, Sang Gil, Fronczek, Frank R., Sahasrabudhe, Girija, Nesterov, Evgueni E., Warner, Isiah M.
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 28.10.2021; MDPI
• Subjects: benzimidazole; Benzimidazoles; Chromophores; Compound A; Crystal structure; Crystallinity; Degree of crystallinity; Design; Efficiency; Electrodes; Electroluminescence; Emitters; Experiments; Fluorescence; Heterocyclic compounds; OLED; optoelectronic applications; Organic light emitting diodes; pyrene; Quantum efficiency; Solid state; Steric hindrance; Thin films; Voltammetry; X ray powder diffraction; X-ray diffraction; St Louis Missouri; United States > US
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules26216523

Three novel small organic heterocyclic compounds: 2-(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound A), 1,3-di(1,2-diphenyl)-1H-benzimidazole-7-tert-butylpyrene (compound B), and 1,3,6,8-tetra(1,2-diphenyl)-1H-benzimidazolepyrene (compound C) were synthesized and characterized for possible applications as blue OLED emitters. The specific molecular design targeted decreasing intermolecular aggregation and disrupting crystallinity in the solid-state, in order to reduce dye aggregation, and thus obtain efficient pure blue photo- and electroluminescence. Accordingly, the new compounds displayed reasonably high spectral purity in both solution- and solid-states with average CIE coordinates of (0.160 ± 0.005, 0.029 ± 0.009) in solution and (0.152 ± 0.007, 0.126 ± 0.005) in solid-state. These compounds showed a systematic decrease in degree of crystallinity and intermolecular aggregation due to increasing steric hindrance, as revealed using powder X-ray diffraction analysis and spectroscopic studies. An organic light-emitting diode (OLED) prototype fabricated using compound B as the non-doped emissive layer displayed an external quantum efficiency (EQE) of 0.35 (±0.04)% and luminance 100 (±6) cd m−2 at 5.5 V with an essentially pure blue electroluminescence corresponding to CIE coordinates of (0.1482, 0.1300). The highest EQE observed from this OLED prototype was 4.3 (±0.3)% at 3.5 V, and the highest luminance of 290 (±10) cd m−2 at 7.5 V. These values were found comparable to characteristics of the best pure blue OLED devices based on simple fluorescent small-molecule organic chromophores.