Synthesis, properties, and application of new luminescent polymers with both hole and electron injection abilities for light-emitting devices

New luminescent polymers that contain both electron-withdrawing cyano groups and electron-rich moieties, triphenylamine (TPA) or tetraphenyldiaminobiphenyl (TPD), were synthesized by Knoevenagel condensation of 1,4-bis(cyanomethyl)-2-[(2-ethylhexyl)oxy]-5-methoxybenzene with the dialdehyde of TPA or TPD, respectively. The polymers were characterized by NMR, FT-IR, microanalysis, GPC, DSC, and TGA. Efficient orange photoluminescence was observed with an absolute quantum efficiency of 48% for the TPA incorporated polymer (TPA-CNPPV). Cyclic voltammetry investigation showed that the polymers presented reversible oxidation and reduction with relatively low potentials, which suggested that the polymers have both good electron and hole injection abilities. We demonstrated an effective approach to synthesize polymers with the triad properties of efficient photoluminescence, good hole injection and high electron-affinity properties, which are highly desirable for application in light-emitting devices. This point was supported by the demonstration of a single layer light-emitting device with a configuration of ITO/TPA-CNPPV/A1, in which good external quantum efficiency (0.1%) and bright luminance of 2100 cd/m² was achieved. Multilayer LEDs using the polymers as the active layers and different charge injection/transporting layers were also investigated. © 1999 American Chemical Society.