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The need of new electrolytes with wide electrochemical window, good stability and conductivity has promoted novel ionic liquids (ILs) as new solutions for supercapacitors. In this work, four hydrophobic room temperature ionic liquids based on organic superbase-derived cations and Trifluoromethanesulfonimide (TFSI) anion were synthetized. The structures of the novel ILs were analyzed, characterized and their performance as a supercapacitor electrolyte was evaluated. The ILs have high decomposition temperatures of up to 490 °C and electrochemical window up to 4.8 V. It was found that there was an optimal chemical structure providing the best stability and operational potential window coupled with moderate conductivity. The IL with the shortest alkyl chain structure provided the highest conductivity but suffered from instability. The performance of the ILs with longer alkyl chains was hindered by lower conductivities and, in the case of the largest chemical structures, also by reduced cyclic stabilities in open air. However, the ionic liquid with moderate alkyl chain length was found to be stable even in open air providing decent conductivity, which can be utilized in future research to develop other hydrophobic ionic liquids suitable as supercapacitor electrolytes.