On the doping of zinc phthalocyanine with 2,2′-difluoro-1,3,2-dioxaborines derived from halo-substituted quinizarines

New 2,2′-difluoro-1,3,2-dioxaborines with pronounced electron accepting properties have been prepared by reaction of quinizarines/halo-substituted quinizarines with BF3·Et2O. From the results of electrochemical analysis, the electron affinities (EAs) of 1,3,2-dioxaborines can be increased when the hydrogen atoms are replaced by halogen ones. Furthermore, conductance of zinc phthalocyanine (ZnPc), a most versatile organic (photo)conductors used in organic light-emitting diodes (OLEDs), can be enhanced greatly when 4,9,10,11,12-pentachloro-2,2,7,7-tetrafluoro-2,7-dihydro-1,3,6,8-tetraoxa-2,7-dibora-benzo[e]pyrene (4c) doped as charge-transport materials which suggesting halogen substitution is a versatile tool for creating efficient new p-dopants.