Side-group engineering of semiconducting naphthalene diimide derivatives with high solution-processability and high thermal stability

Abstract

A series of new naphthalene diimide (NDI) semiconducting derivatives with different N -phenyl bicyclic side groups were rationally designed and synthesized in this study. The solubility of the orthogonal-shaped NDI derivatives with 5-tetralinyl and 4-indanyl side groups was found to be up to two orders of magnitude higher than that of the linear-shaped NDI derivatives with 6-tetralinyl and 5-indanyl side groups. The orthogonal-shaped NDI derivative with a 5-tetralinyl side group exhibited excellent solution processability due to its high solubility (e.g., 4 g/100 g dichlorobenzene), high thermal stability (e.g., lowest phase transition temperature of 380 °C), and high vertical carrier mobility (e.g., space-current-limited-current electron mobility of 7 × 10 −5 cm 2 /V·s). Therefore, the introduction of N -phenyl bicyclic side groups on organic semiconductors was confirmed to be a highly promising design strategy for achieving the desired physical properties. New orthogonal-shaped naphthalene diimide (NDI)-derived semiconductors with N -phenyl bicyclic side groups exhibited excellent solution processability, high thermal stability, and high electron mobility. • New naphthalene diimide semiconducting derivatives with N -phenyl bicyclic side groups were rationally synthesized. • The orthogonal-shaped derivatives were up to two orders of magnitude higher solubility than linear-shaped derivatives. • The orthogonal-shaped derivatives exhibited excellent solution processability, thermal stability, and electron mobility.