Synthesis, crystal structure, photo- and electro-luminescence of 3-(4-(anthracen-10-yl)phenyl)-7-(N,N′-diethylamino)coumarin

A new coumarin derivative, 3-(4-(anthracen-10-yl)phenyl)-7-(N,N′-diethylamino)coumarin, was synthesized and characterized by FT-IR, 1H NMR, element analysis and single crystal X-ray crystallography. The dihedral angle of coumarin ring and phenyl group is 30.83°, and the dihedral angle of phenyl group and anthracene skeleton is 76.99°. The photoluminescent (PL) and electroluminescent (EL) properties of the compound were investigated. The results show that the compound exhibits high fluorescence quantum yield (0.83), large Stokes shift and strong blue emission (466 nm). The electroluminescence devices comprised of vacuum vapor-deposited films using the compound as dopant were fabricated, showing blue emission that is identical to its photoluminescent spectrum in chloroform solutions. The electroluminescence device of indium tin oxide (ITO)/4,4′,4″-tris[2-naphthyl (phenyl)-amino]triphenylamine (2-TNATA) (5 nm)/N,N-bis-(1-naphthyl)-N,N′-diphenyl-1,1′-biphenyl-4,4′-diamine (NPB) (40 nm)/4,4-N,N-dicarbazole-biphenyl (CBP): dopant (1.0 wt%, 30 nm)/2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole (PBD) (30 nm)/LiF (1 nm)/Al (100 nm) gives a maximum luminous efficiency of 3.3 cd/A at the current density of 20 mA/cm2, and maximum luminance of 5070 cd/m2 at 16 V.