Six samples of model compounds 4-HO-4’-X-N-(benzylidene)-anilines were synthesized and their molecular structures were identified by 1H NMR and 13C NMR. Their ultraviolet absorption spectra were measured in six kinds of solvents. The effects of substituents and solvents on the energies νmax of longest wavelength maximum of ultraviolet absorption spectra were discussed. The research results show that the substituent effect of X on the νmax is dominated by polar substituent constant σ and excited-state substituent parameterσexCC. While the solvent effect on the νmax is dominated by the n-octanol/water partition coefficient (logP) and the solvatochromic dye (ET(30)). Besides the logP and ET(30), there is a special solvent effect of dimethyl sulfoxide on the νmax.