Triboelectric nanogenerator (TENG) has garnered significant attention as a promising technology for energy harvesters and flexible electronics. However, the current state-of-the-art TENG suffer from the low electric output and limited lifespan, which pose significant obstacles to their broader implementation. Therefore, a TENG with ultra-high electric output and circular life cycles is developed by combining dynamic covalent chemistry and TENG technologies. Specifically, imine-vitrimer elastomers (IVEs) with excellent compression resilience are synthesized and utilized to fabricate TENG as an electronegative tribolayer. The assembled TENG can generate ∼18-fold higher electric charge density than traditional PTFE-based TENG. This substantial improvement enables the TENG to power over 2400 commercial LEDs, showcasing the great potential for high-sensitivity traffic sensors and energy intensive device. Moreover, to solve inevitable wear or tear of the tribolayers during mechanical friction, efficient self-healing and recycling of tribolayer are achieved, ensuring their consistently high electric output and durability. This study proved a new sight to fabricate the next generation TENG with high performance and circular life cycles.