Spirobifluorene (SBF) is one of the most commonly utilized scaffolds in the construction of Organic Semi-Conductors (OSCs) for organic electronics. In the last ten years, new generations of SBF positional isomers have been surfaced in the literature. The various substitution places have enabled the tailoring of important electrical properties for the future construction of materials. These new generations of organic semiconductors have shown great promise to the field of electronics, particularly when utilized as a host material for Thermally Activated Delayed Fluorescence OLEDs. We present these new generations of SBF compounds, as well as the impact of positional isomerism on electrical characteristics and device performance, in this featured article. We show how distinct structural and electrical characteristics drive and can be adjusted to the electrochemical and photophysical properties of SBF regio-isomers. Such research lays the groundwork for organic electronic material design.