Highly Efficient Blue Organic Light-Emitting Diodes Based on 2-(Diphenylamino)fluoren-7-ylvinylarene Derivatives that Bear a tert-Butyl Group

摘要

Blue fluorescent materials with a 2-(diphenylamino)fluoren-7-ylvinylarene emitting unit and tert-butyl-based blocking units were synthesized. The photophysical properties of these materials, including UV/Vis absorption, photoluminescent properties, and HOMO–LUMO energy levels, were characterized and rationalized with quantum-mechanical DFT calculations. The electroluminescent properties of these molecules were examined through the fabrication of multilayer devices with a structure of indium–tin oxide, 4,4′-bis{N-[4-(N,N-di-m-tolylamino)phenyl]-N-phenylamino}biphenyl, 4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl, and blue materials doped in 2-methyl-9,10-di(2-naphthyl)anthracene/tris(8-quinolinolato)aluminum/LiF/Al. All devices exhibit highly efficient blue electroluminescence with high external quantum efficiency (3.20–7.72 % at 20 mA cm−2). A deep-blue device with Commission Internationale de l’Eclairage (CIE) coordinates of (0.15, 0.11) that uses 7-[2-(3′,5′-di-tert-butylbiphenyl-4-yl)vinyl]-9,9-diethyl-2-N-(3,5-di-tert-butylphenyl)-2,4-difluorobenzenamino-9H-fluorene as a dopant in the emitting layer showed a luminous efficiency and external quantum efficiency of 3.95 cd A−1 and 4.23 % at 20 mA cm−2, respectively. Furthermore, a highly efficient sky-blue device that uses the dopant 7-{2-[2-(3,5-di-tert-butylphenyl)-9,9′-spirobifluorene-7-yl]vinyl}-9,9-diethyl-2-N,N-diphenylamino-9H-fluorene exhibited a luminous efficiency and high quantum efficiency of 10.3 cd A−1 and 7.7 % at 20 mA cm−2, respectively, with CIE coordinates of (0.15, 0.20).