2,8-Difluoro-5,11-bis(triethylsilylethynyl)anthradithiophene (dif-TES-ADT) is a small molecule organic semiconductor that has drawn much interest as an active channel in Organic Thin Film Transistors (OTFTs). In particular, the solubility of dif-TES-ADT in numerous solvents and amorphous polymers, its chemical stability, and its ease in processing make it a supreme candidate for high performance devices. This review summarizes the progress in material crystallization and the film formation approach, including the surface treatment of Source/Drain metal electrodes with various self-assembled monolayers (SAMs) and the works on vertical phase segregation derived from blending dif-TES-ADT with various polymers. Electrical and environmental stabilities in dif-TES-ADT-based OTFTs and their origins are summarized. Finally, a discussion on the emerging applications of dif-TES-ADT OTFTs is explored. We believe that the individual effort summarized in this work will shed light on optimizing the electrical performance of dif-TES-ADT-based transistors and reveal their potential qualities, which will be useful to their applications in next-generation high performance organic electronics.