Synthesis and characterization of highly soluble 9,10-diphenyl-substituted poly(2,6-anthracenevinylene)

We report the synthesis and optoelectronic properties of highly soluble poly(9,10-bis(3',4'-di(2 ''-ethyl-hexyloxy))phenyl)-2,6-anthracenevinylene) (HSM-PAV). The key intermediate for the synthesis of HSM-PAV is 2,6-dimethyl-9,10-dibromoanthracene, and the high solubility of HSM-PAV is from the incorporation of lateral 3,4-di(2-ethylhexyloxy)phenyl moieties into the 9,10-positions of anthracene units. The increase of side alkyloxy groups endows HSM-PAV with higher molecular weight (M-n = 3.2 x 10(4)) and better electroluminescence performances (L-max = 590 cd/m(2), LEmax = 0.27 cd/A) compared with the poly(2,6-anthracenevinylene) with lateral monoalkyoxy moieties (M-n = 1.9 X 10(4), L-max = 340 cd/m(2), LEmax = 0.17 cd/A). The electrical conductivity of doped HSM-PAV film with iodine is 5 x 10(-2) S cm(-1) that is several order higher than that of doped 9,10-anthracene-based polymers, further demonstrating that linkage position has a dramatic effect on the optoelectronic properties of anthracene-based conjugated polymers. (C) 2009 Elsevier Ltd. All rights reserved.