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Nonconjugated segments in polymer semiconductors have been utilized to improve the processability of semiconducting polymers. Recently, several reports have described the improvement of stretchability of polymer semiconductors by incorporating nonconjugated spacers. However, the effect of relative flexibility of such conjugation breakers on mechanical and electrical properties has not yet been studied systematically. Here, conjugation breakers with different chain length and rigidity are incorporated into the backbone of diketopyrrolopyrrole‐based semiconductors. Interestingly, it is observed that the longer and more flexible conjugation breakers result in greater ductility and lower elastic modulus without significantly affecting mobility. The enhancement of stretchability is attributed to the reduced modulus and the decrease in crystallinity, as confirmed by X‐ray diffraction. With this newly established molecular …