In order to improve the toughness and solubility of bismaleimide resin and improve its application in the field of high frequency and high speed copper clad laminate, a silicone modified bismaleimide resin (Si-D936) was designed and synthesized from silicone and D936 type bismaleimide in this paper. The characteristic structure of Si-D936 and silicon-D936 monomer were characterized by IR, NMR, and gel permeation chromatography. Additionally, the effects of different silicon contents on the solubility, heat resistance, mechanical properties, and dielectric properties at 10 GHz of the Si-D936 were explored. The results show that compared with the modified D936, the solubility of Si-D936 in butanone is obviously improved, and the highest solubility can reach 30% (at room temperature). However, with the increase of Si content, the molecular weight of Si-D936 increases, and the solubility decreases slightly. The Si-D936 modified resin has good thermal properties after curing, but the heat resistance and residual carbon rate decrease gradually with the increase of Si content. The silicone modification can improve the mechanical properties of D936 resin, in which the impact strength and tensile strength of Si-D936-1 (the molar ratio of D936 to HMM is 3:1) increase by 35% and 24.6%, respectively. However, with the further increase of Si content, the cross-linking degree of the modified resin is affected, and the impact strength, bending strength, and tensile strength of the modified resin decrease. After silicone modification, the dielectric properties of the modified resin are improved, and the dielectric loss is reduced from 0.009 4 to 0.007 2 (10 GHz).