A series of aryl‐substituted naphthalenediimide derivatives that contain nitroxide radicals were prepared and their crystal structures were elucidated. Much stronger charge‐transfer interactions were present in the derivatives with perfluorobenzene substituents than those with phenyl or 4‐fluorophenyl substituents. These interactions result in the formation of single‐component charge‐transfer complexes by self‐assembly of the naphthalenediimide derivatives to provide black crystals. As a consequence, the naphthalenediimide derivatives with perfluorobenzene substituents have better field‐effect transistor (FET) properties than the other derivatives.

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