A novel n-type organic semiconductor comprising a 1,5-naphthyridine-2,6-dione unit

The first examples of 1,5-naphthyridine-2,6-dione (NTD)-based n-type small molecules, NTDT-DCV and NTDP-DCV with an electron-withdrawing dicyanovinyl terminal unit and different aromatic bridging groups (thiophene and benzene, respectively), were synthesized and characterized. Two different bridging rings were incorporated to explore the structure-property relationship as well as to precisely control the electrical properties. Among them, NTDT-DCV exhibited a higher maximum electron mobility of 0.14 cm 2 V −1 s −1 in organic thin-film transistors (OFETs), attributed to the planar structure, low reorganization energy, and well-connected smooth surface thin-films. To further demonstrate the n-type properties of NTDT-DCV , we have fabricated a p-type OFET device with overlaid NTDT-DCV nanopatches. While the pristine OFET with a p-type NTDT semiconductor showed a hole mobility of 1.29 cm 2 V −1 s −1 , that with an overlaid NTDT-DCV nanopatch showed an increased hole mobility of 2.41 cm 2 V −1 s −1 , ascribed to the appropriate energy level offset and efficient intermolecular charge-transfer doping interaction into the overlaid nanopatch. The first examples of 1,5-naphthyridine-2,6-dione (NTD)-based n-type small molecules, NTDT-DCV and NTDP-DCV with an electron-withdrawing dicyanovinyl terminal unit and different aromatic bridging groups were synthesized and characterized.