| Phthalocyanine compound is a kind of important organic photoconductive material, especially silicon phthalocyanine is new CGL, so it is significant to studied and improve the synthetic method of the phthalocyanine.A new synthesis method of metal-free phthalocyanine using 1,3-diiminoiso- indoline as main material and trimethoxysilane as hydrogen donator was developed in this paper. The influences of reaction conditions such as material ratio, reaction temperature and time were studied.The optimum preparing condition was that the mole ratio of 1,3-diiminoiso- indoline and trimethoxysilane was 4:3,sodium methylate and tributylamine as additive ,reaction time 11h at 220℃, the yield of metal-free phthalocyanine was 46.7%.Silicon phthalocyanine dichloride was synthesized through the reaction of 1,3-diiminoisoindoline with silicon tetrachloride in quinoline. The reaction conditions was briefly studied, The optimum preparing condition was that the mole ratio of silicon tetrachloride and 1,3-diiminoiso- indoline was 3:2 , reaction time 0.5h at 220℃. The precipitation in methanol was carried out when the mixture was cooled to 80℃ and then to filtrate in order to separate the product successfully. The highest product yield was 58.0%. Silicon phthalocyanine dihydroxide was prepared from silicon phthalocyanine dichloride through two methods. The first was alkali treating that meaned silicon phthalocyanine dihydroxide was treated in the ethanol solution containing sodium methylate .The second was acid treating meaned precipitating its solution in concentrated sulfuric acid into ice water. The product yield of the second method was 77.0%, which was higher than the method of alkali treating.IR, X-ray diffraction analysis, elemental analysis and differential thermal analysis were used to determine the structure, crystalline form and thermal stability of compounds synthesized in this paper. |