This paper systematically demonstrated a variety of experimental phenomena of random lasers (RLs) of N,N′-di-(3-(isobutyl polyhedral oligomeric silsesquioxanes)propyl) perylene diimide (DPP) organic/inorganic hybrid laser dye, which is composed of perylene diimide (PDI) as gain media and polyhedral oligomeric silsesquioxanes (POSS) as scattering media at a mole ratio of 1:2. In this work, we observe the transition from incoherent RL in the DPP-doped solutions and polymer membrane systems using dip-coating method to coherent RL in the polymer membrane system with defect waveguide using semi-polymerization (SP) coating method. Meanwhile, we found that the hybrid dye-DPP has a long lasing lifetime compared with the traditional laser dyes, which indicates that the POSS group can suppress the photo-bleaching effect to extend the working life of laser dyes.