Synthesis and electroluminescence of thiophene-based bipolar small molecules with different arylamine moieties

A series of fluorescent dyes consisted of a thiophene unit, an 1,3,4-oxadiazole unit and four different arylamine moieties were prepared using a facile multi-steps synthetic route with high yield. The four arylamine structures studied were triphenylamine, N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine, diphenyl(1-naphthyl)amine and 9-phenylcarbazole. Experimental results shown that their HOMOs varied from 5.21 to 5.73 eV strongly affected by the arylamine chemistry while their LUMOs remained relatively unchanged. Their corresponding emission colors ranged from UV (393 nm) to bluish green (483 nm). In general, the thiophene unit enhanced the overall thermal stability of the compounds. According to cyclic voltammetry, the compounds are predominantly hole-transporting while OLED results indicated cpd 10 possess both hole and electron transport properties. Single layer OLED fabricated from 10 resulted in ca. 2000 cd/m2 (luminous intensity) and 1.10 cd/A (current efficiency) max, whereas, a multilayer OLED using 10 as the hole transporting layer achieved over 7400 cd/m2 and 2.3 cd/A max.