Synthesis Of Hole Transporting Materials Containing Butadiene Moiety And Their Properties Study

The compounds containing butadiene moiety is a kind of important Hole Transporting Materials(HTM). Due to their easy prepared, high hole mobility and forming film without the addition of polymers, they can be widely used in Organic Photo-Conductors(OPC). In this thesis, 1,1-diphenyl-3-chloropropylene was prepared by the Grignard reaction, dehydration reaction and chloromethylation reaction using bromobenzene and acetophenone as the raw materials, and its optimal technical conditions were studied. 1-(1-naphthyl)-1-phenyl-3-chloropropylene was prepared by the same route, while five kinds of N,N-disubstituted aminobenzaldehyde like 4-(N-phenyl-N-(4'-methyphenyl))aminobenzaldehyde were synthesizd by the Vilsmeier reaction firstly. Then three kinds of 1,1,4,4-tetraaryl-1,3-butadiene derivatives were synthesized via Grignard and dehydration reaction using 1,1-diaryl- 3-chloropropylene and bis(4-(diethylamino)phenyl)methanone as the raw materials, and the optimal technical conditions of synthesis of 4,4'-(4,4-diphenyl-1,3- butadienylidene)bis[N,N-diethyl-benzenamine] (CT6) were studied. And five kinds of 4-(4,4-diphenyl-1,3-butadienyl)-N,N-disubstituted benzenamine like 4-(4,4-diphenyl -1,3-butadienyl)-N,N-bis(4-methylphenyl) benzenamine (CT5) were obtained by the Wittig-Horner reaction using 1,1-diphenyl-3-chloropropylene and N,N-disubstituted aminobenzaldehyde as the raw materials. The structure of the synthesized compounds were determined by UV, IR, MS, EA, 1H NMR and X-ray diffraction.Finally, the OPC of functional separation type were fabricated using synthesized compounds containing butadiene moiety as the HTM and Y-TiOPc as the charge generation materials, The test results showed that all of the synthesized compounds containing butadiene moiety had excellent photographic performance except that the OPC can't be prepared by using 1,1,4,4-tetraaryl-1,3-butadiene as HTM. The data of their half-decay exposure were less than 1.00 lx·s, residual voltage were no higher than 80V, dark decay speed were less than 25.0 V·s-1. When using the synthesized compounds CT5 and CT6 as HTM in Organic Light-Emitting Diodes (OLED), they show much more excellent hole-transporting properties than the traditional HTM N,N'-diphenyl-N,N'-di(4-tolyl)-[1,1'-biphenyl]-4,4'-diamine.