The invention provides an oligomeric chitosan structure-based binaphthalene-containing axial chiral quaternary ammonium salt phase transfer catalyst and a preparation method thereof. The preparation method comprises the following steps: under alkali catalysis, performing a constant-temperature reaction on N-substituted oligomeric chitosan and chiral binaphthyl benzyl bromide in a dry organic solvent, and after completion of the reaction, washing, extracting and separating to obtain the oligomeric-chitosan-structure-based binaphthalene-containing axial chiral quaternary ammonium salt phase transfer catalyst. By the preparation method, the novel oligomeric chitosan structure-based binaphthalene-containing axial chiral quaternary ammonium salt phase transfer catalyst is prepared, and the oligomeric chitosan structure-based binaphthalene-containing axial chiral quaternary ammonium salt phase transfer catalyst can be used for catalyzing a conjugation addition reaction performed on malonate and alpha, beta-unsaturated carbonyl compounds so as to prepare an addition product at a high yield of 45-82% and a medium enantioselective ee value of 20-53%.