Anthracene-Based Organic Small-Molecule Electron-Injecting Material for Inverted Organic Light-Emitting Diodes

A diphenylanthracene dimethylamine derivative (9-{3,5-di(N,N-dimethylaminoethoxy)phenyl}-10-phenyl-anthracene, DPAMA) was synthesized by the Suzuki–Miyaura cross-coupling reaction. Its ammonium salt, 9-{3,5-di(trimethylammonium ethoxy)phenyl}-10-phenyl-anthracene dichloride (DPAMA-Cl), was also synthesized as a reference material. DPAMA was characterized by UV–vis and fluorescence spectroscopy, cyclic voltammetry, photoelectron yield spectroscopy, and X-ray photoelectron spectroscopy to evaluate the work function-modifying ability of DPAMA on indium tin oxide (ITO) and ZnO. The work functions of ITO and ZnO changed from 4.4 and 4.0 eV (pristine) to 3.8 and 3.9 eV, respectively. Using this surface modification effect of DPAMA, inverted organic light-emitting diodes were fabricated with device structures of ITO/DPAMA/Alq3/NPD/MoO3/Al (Alq3 = tris(8-hydroxyquinolinato)aluminum; NPD = N,N′-di-[(1-naphthyl)-N,N′-diphenyl]-1,1′-(biphenyl)-4,4′-diamine) and ITO/ZnO/DPAMA/Alq3/NPD/MoO3/Al. Both devices showed good performance at the range of current density, 1–300 mA/cm2. The best inverted organic light-emitting diodes device showed luminance of 7720 cd/m2, current efficiency of 4.51 cd/A, and external quantum efficiency of 1.45%. Also, poly(3-hexylthiophene):mixed phenyl-C61 and C71 butyric acid methyl ester-based organic solar cells using DPAMA and DPAMA-Cl as electron-transporting materials showed power conversion efficiencies of 3.3 and 3.4%, respectively.