Novel 2,5-bis(6-(trimethylamonium)hexyl)-3,6-diaryl-1,4-diketopyrrolo [3,4-c]pyrrole pigments as levelers for efficient electroplating applications

2,5-Bis(6-(trimethylamonium)hexyl)-3,6-diaryl-1,4-diketopyrrolo [3,4-c]pyrrole (DPP) pigments are excellent choices as levelers for copper electrodeposition. Herein, novel 4-methoxylaryl (1b) and 4-trifluoromethoxyaryl (1d) diketopyrrolopyrrole-based levelers were synthesized and the inhibitory ability of these levelers is evaluated by electrochemical measurements on copper electrodeposition which were compared with 4-methylaryl (1a) and 4-trifluoromethylaryl (1c) diketopyrrolopyrrole-based levelers. To investigate interactions between metal surface and additives, quantum chemical calculations and molecular dynamics simulations were used. Among them, the 4-trifluoromethoxy-DPP (1d) showed optimal inhibition and strong adsorption capacity on the copper surface. Then, as the representative leveler, 1d was selected for the systematic study of the leveling influence during microvia filling. Notably, 1d has achieved the bottom-up deposition of microvias under the synergistic effect of the microvia filling performance reached 96.9%. These results demonstrated that 1d could serve as a promising leveler for microvia filling and provide theoretical guidance to the discovery and synthesis of novel levelers.

Automated summary

Novel 4-methoxylaryl and 4-trifluoromethoxyaryl DPP-based levelers were synthesized and evaluated for their inhibitory ability on copper electrodeposition. Among them, 4-trifluoromethoxy-DPP showed optimal inhibition and strong adsorption capacity, making it a promising leveler for microvia filling. The systematic study demonstrated that 4-trifluoromethoxy-DPP achieved a high filling rate of 96.9% under the synergistic effect of the microvia filling performance.