Organosoluble, low‐dielectric‐constant fluorinated polyimides based on 2,6‐bis(4‐amino‐2‐trifluoromethylphenoxy)naphthalene

Abstract

AbstractA novel fluorinated bis(ether amine) monomer, 2,6‐bis(4‐amino‐2‐trifluoromethylphenoxy) naphthalene, was prepared through the nucleophilic aromatic substitution reaction of 2‐chloro‐5‐nitrobenzotrifluoride and 2,6‐dihydroxynaphthalene in the presence of potassium carbonate, followed by catalytic reduction with hydrazine and Pd/C in ethanol. A series of novel trifluoromethylated polyimides were synthesized from the diamine with various commercially available aromatic tetracarboxylic dianhydrides using a two‐stage process with thermal imidization of poly(amic acid) films. Most of the resulting polyimides were highly soluble in a variety of organic solvents and could afford transparent and tough films via solution casting. These polyimides exhibited moderately high glass transition temperatures (Tgs) of 249–311 °C, high thermal stability and good mechanical properties. Low moisture (0.19–0.85 %), low dielectric constants (2.49–3.59 at 10 kHz), and low color intensity were also observed. For a comparative study, a series of analogous polyimides based on 2,6‐bis(4‐aminophenoxy)naphthalene were also prepared and characterized. Copyright © 2005 Society of Chemical Industry