Synthesis and characterisation of rubbing-resistant polyimides with naphthalimide side-chain for liquid-crystal alignment layers

A novel diamine with a side-chain containing naphthalimide ring and non-polar alkyl end group, N-octyl-4-(3,5-dinitrobenzoyl)-amido-1,8-naphthalimide (N8), was synthesised and its chemical structure was confirmed by FTIR (fourier transform infrared) spectroscopy and nuclear magnetic resonance spectroscopy (¹H-NMR). Then, a new family of polyimides (PIs) containing naphthalimide unit in the side-chains has been successfully synthesised by reaction of 4,4′-oxydiphthalic anhydride (ODPA) and 3,3′-dimethyl-4,4′-methylenediamine (DMMDA) with the novel functional diamine N8. The obtained polymers showed excellent solubility in a broad range of solvents, including tetrahydrofuran. Thermal properties of polymers were good enough to permit the use of these PIs on liquid-crystal displays (LCDs) applications. Alignment films obtained by casting offered outstanding rubbing-resistant ability, meanwhile kept the pretilt angle high above 89°. The PI seems to be prospective materials for alignment layers in LCDs.