Core-chlorinated naphthalene tetracarboxylic diimides (NDIs) with fluoroalkyl chains are synthesized and employed for n-channel organic thin-film transistors (OTFTs). Structural analyses of the single crystals and thin films are performed and their charge-transport behavior is investigated in terms of structure–property relationships. NDIs with two chlorine substituents are shown to exhibit a herringbone structure with a very close π-plane distance (3.3–3.4 Å), a large π-stack overlap (slipping angle ca. 62°), and high crystal densities (2.046–2.091 g cm−3). These features result in excellent field-effect mobilities of up to 1.43 cm2 V−1 s−1 with minimal hysteresis and high on–off ratios (ca. 107) in air. This is similar to the highest n-channel mobilities in air reported so far. Despite the repulsive interactions of bulky Cl substituents, tetrachlorinated NDIs adopt a slip-stacked face-to-face packing with an interplanar distance of around 3.4 Å, resulting in a high mobility (up to 0.44 cm2 V−1 s−1). The air-stability of dichlorinated NDIs is superior to that of tetrachlorinated NDIs, despite of their higher LUMO levels. This is closely related to the denser packing of the fluorocarbon chains of dichlorinated NDIs, which serves as a kinetic barrier to the diffusion of ambient oxidants. Interestingly, these NDIs show an optimal performance either on bare SiO2 or on octadecyltrimethoxysilane (OTS)-treated SiO2, depending on the carbon number of the fluoroalkyl chains. Their synthetic simplicity and processing versatility combined with their high performance make these semiconductors highly promising for practical applications in flexible electronics.
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