Addressing the thermal resistance between rough interfaces without applying pressure to the interfacial sandwich has been a challenge. Herein, a thermal interface phase change material (TIPCM) is designed to realize a 3D support skeleton with a dynamic crosslinking network by introducing a boron ester crosslinking backbone into paraffin wax (PW) and ethylene-octene copolymer (EOC), thus enabling the TIPCM to ensure mechanical integrity without leakage even above the melting temperature of EOC. The chemical cross-linking between the organic solid–liquid phase change material (PCM) and the polymer realizes thermally triggered self-healing and adaptive shape memory properties. The phase transition of PW leads to a decrease in the modulus of TIPCM and activates the ester exchange of the dynamic covalent bonding of boron esters, which allows TIPCM to self-heal and self-adapt to a variety of object surfaces. These enabled the TIPCM to fill the interface gaps through small stress deformations, forming an interlocking structure that reduces contact thermal resistance and promotes heat transfer. The obtained TIPCM achieves excellent chip thermal management performance, cooling the analog CPU temperature by 67 °C at 5 V. In conclusion, this study provides a potential strategy for redesigning TIPCMs with high latent heat and special physical properties for thermal management.