Synthesis And Process Optimization Of A 2,6-naphthalene Diamine Derivative

Triarylamine with good hole-transporting ability are one of the most important materials for organic electroluminescent diodes (OLEDs). However, the common triarylamine have a low melting point and glass transition temperature, poor thermal stability. Their layer represents the weakest link in the electroluminescent structure considering the thermal stability of these materials.By studying different organic electroluminescent materials, this dissertation designe d a new compound-N,N-bis(9,9-dimethyl-9H-fluoren-7-yl)-N',N'-diphenylnaphthalene-2, 6-diamine:a naphthalene ring, two fluorene rings with dimethyl in C-9, two benzene rings. Target product is expected to have a high fluorescence quantum efficiency, melt ing point, glass transition temperature and good solubility.This dissertation designed several synthetic methods. After a full evaluation, a be st route was determinated, which was also verified by mechanism analysis. Started fro m 2-naphthol by bromination,6-bromo-2-naphthol was obtained, and then condensed with aniline at high temperature to obtain 6-bromo-N-phenyl-2-naphthylamine. The for mer product react with iodobenzene to prepare 6-bromo-N,N-diphenyl-2-naphthylamine. After the N-arylation of tert-butyl carbamate with 2-bromo-(9,9-dimethyl)fluorene, it was then deprotected and bis(9,9-dimethyl-9H-fluoren-7-yl)amine was obtained. Finally, 6-bromo-N,N-diphenyl-2-naphthylamine and bis(9,9-dimethyl-9H-fluoren-7-yl)amine wer e used to obtained N,N-bis(9,9-dimethyl-9H-fluoren-7-yl)-N',N'-diphenylnaphthyl-2,6-dia mine.This synthetic route was quite feasible because of common raw materials, mild r eaction conditions and a good yield.Single-factor experiments were carried out to find the best reaction conditions, such as time, temperature, material ratio, catalyst, ligand, etc. Several synthetic methods were carried out to determine schemes that meet different requirements. The structure of the synthetic products were characterized by infrared(IR), mass spectra(MS) and'H nuclear magnetic resonance(NMR), the result showed that each intermediate and the target product conformed to the design requirements and the synthetic method was feasible.