It’s known that the application of bismaleimide resins (BMI) is limited due to its brittleness and poor flame retardancy. A novel type of BMI monomer (MADQ) based on the typical phosphorus series flame retardant DOPO is designed to improve the fire safety of BMI. Besides, aliphatic long chain structure is introduced in MADQ, which is supposed to be conducive to reducing the rigidity of the BMI cross-linked network and thus to improve the toughness of BMI. It’s seen that with the incorporation of 5.24 wt% MADQ, the peak of heat release rate (PHRR) and total heat release (THR) of resultant BMI/MADQ-5 is reduced by 37.7% and 33.9%, respectively. Meanwhile, with modification of 1.07 wt% MADQ, BMI/MADQ-1 possesses UL-94V-0 rating. The relevant mechanism analysis reveals that the phosphaphenanthrene group in MADQ can exert flame retardancy effect both in condensed and gas phase. Besides, the impact strength of the BMI/MADQ is maximally increased by nearly 90.1%. Furthermore, the BMI/MADQ still maintains high tensile strength and thermal stability, which indicates the modification of MADQ did not deteriorate other properties of BMI. An innovative research idea and research basis for the preparation of intrinsic flame-retardant and toughened BMI is provided in this work.