A novel bisphthalonitrile monomer containing allyl groups (DBPA-Ph) had been synthesized via the reaction of diallyl bisphenol A (DBPA) and 4-nitrophthalonitrile. The chemical structure of DBPA-Ph was confirmed by 1HNMR, 13CNMR, and FTIR spectroscopy. The curing behaviors and processability of DBPA-Ph were studied by differential scanning calorimetry (DSC) and dynamic rheological analysis. The monomer manifested a two-stage thermal polymerization pattern. The first stage was attributed to the polymerization of allyl groups and the second to the ring-form polymerization of cyano groups. The result of dynamic rheological analysis indicated the monomer had wide curing window and the self-catalyzed curing behavior. DBPA-Ph polymers were prepared from the thermal polymerization with short curing time, showing high glass transition temperature (>350°C) and attractive thermal decomposition temperature (>430°C). The outstanding glass transition temperature, desirable thermo-oxidative stabilities, good processability and sound process conditions could provide more applications to the DBPA-Ph polymers. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 41203.