A novel diamine containing naphthalene and 1,2,3-triazole was synthesized by click reaction in the presence of Cu (I) catalyst. The synthesized diamine reacts with commercially available dianhydride and zinc oxide (ZnO) to form polyimide (PI) nanocomposites by a conventional two-step method. The structure of the monomers and polymers was characterized by Fourier transform infrared and proton nuclear magnetic resonance spectra. The morphology of the PI and PI/ZnO nanocomposite films was investigated by scanning electron microscopy and X-ray diffraction analysis. Meanwhile, due to the presence of a naphthalene side group, PI and PI/ZnO nanocomposite films possess high thermal stability, with a glass transition temperature over 259°C and a decomposition temperature with 5% weight loss over 501°C under nitrogen atmosphere. Also, low moisture absorption (0.28%) and good optical transparency were evident. The hybrid films possessed good mechanical properties, with a tensile strength of 112–127 MPa, an elongation at break of 10–15%, and a tensile modulus of 2.8–3.2 GPa.
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