Synthesis And Application Of Novel Gemini Quaternary Ammonium Compounds

The linear gemini compounds were generally prepared by the reflux reaction of a mixture of tertiary amines and a dihalide in ethanol.The series of gemini compounds containing pyridinium rings as the head groups were obtained by reacting the mixture of 4,4_-bipyridine and alkyl or aryl bromides in N,N-dimethylformamide(DMF)at reflux.After removal of the solvent under vacuum,the residue was recrystallized two times.The reactive conditions of several Gemini quaternary ammonium compounds were investigated.The optimum reaction time,temperature,raw material ratio and the yield of the target product were determined in the experiments.1H NMR and FT-IR spectra were used to characterize the the molecular structure of the Gemini compounds.The six kinds of synthesized Gemini quaternary ammonium compounds and their SPS mixtures were used as additives in copper electrodeposition of TSV.They include linear and pyridinium gemini series.Galvanostatic experiments(potential-time curves),the measurement of carbon contents and scanning electron microscopy(SEM)were used to investigate the structure-property relationship of the Gemini compounds.The TSV vias were perfectly filled by using the Gemini compounds as an additive in copper electrodeposition.Thus,the Gemini compounds appears to be a promising candidate as an additive in the feature filling electrodeposition.The type and the length of the spacer of Geminis are of major importance for their suppressing capability and the vias filling performance.Gemini molecules response to SPS shows structure dependence and depends mainly on the rigidity of the hydrophobic tails.SPS may improve the via filling performance for the geminis with flexible hydrophobic tails,while it may lead to a reduced via filling behavior for those with the rigid hydrophobic tails.Potential oscillation in the galvanostatic experiment can be associated with the rigidity of the hydrophobic tails of Geminis.