Small molecule organic semiconductors have well-defined structures and can be used in place of polymers which often show batch-to-batch variation. Many different electron-rich donor and electron-deficient acceptor units have been used to design materials with reduced HOMO-LUMO gaps and improved mobilities. Here we introduce a novel acceptor unit, 1-dodecyl-6-dodecoxynaphthyridine-2-one. This acceptor unit has been used in the synthesis of two novel compounds, with thiophene and 2,1,3-benzothiadiazole (BT) cores. The BT-containing compound shows a narrower HOMO-LUMO gap, broad solid-state absorption and has been applied to organic field-effect transistors, showing a mobility of 0.022 cm2 V−1 s−1 after optimisation of devices using self-assembled monolayers.