Photoelectric Conversion Properties Of Naphthalocyanine Compounds

With the rapid developments of organic optoelectronic devices, such as organic solar cells, it becomes an impending need to develop organic semiconductor materials with broad absorption range, especially in the near infrared region. In this dissertation, based on molecular design and material composition, the typical p-type material of zinc phthalocyanine was benzoannulated. The effect of the extending p-conjugated system on energy levels and electron-donating ability was investigated in details. The azo group moieties were also introduced to the periphery of phthalocyanine ring, in order to obtain organic semiconductor materials with a broader spectrum absorption range matching the solar spectrum.A series of 2,3-naphthaloeyaninatozinc compounds have been successfully prepared by using the Diels-Alder reaction. Their molecular structures were characterized by FT-IR, elemental analysis, and MALDI-TOF mass spectrum. The mechanism of the synthetic reactions and the factors which have influence on reactions were discussed.The energy band of ZnNc was studied by cyclic voltammetry and optical absorption spectra. The results demonstrated that the extension of the conjugated system reduced the band gap of ZnNc compound. The composites of ZnNc with electron acceptors of N,N-dipyrimidinyl-3,4,9,10-perylenetetracarboxylic diimide (DMP), C₆₀, and 1-(3-methoxycarbonyl)propyl-1-phenyl [6,6]C₆₁ (PCBM) were prepared by solution-blending, layer-by-layer evaporation, and spin-coating, respectively. The fluorescence quenching of the composites indicated that the photo-induced charge transfer occurred due to the energy level offset between ZnNc and the acceptor molecules.A novel phthalocyanine substituted with azo group moiety on the periphery of phthalocyanine ring was synthesized. Compared to normal phthalocyanines, the obtained compound showed broad absorption in the near infrared region as well as the visible region.