Preparation and properties of highly organosoluble polyimides derived from 2,2′-disubstituted-4,4′-oxydianilines

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Abstract

Four novel aromatic, symmetrical ether diamines (2,2′-bis(biphenyl)-4,4′-oxydianiline, 2,2′-bis[4′-(3″,4″,5″-trifluorophenyl)phenyl]-4,4′-oxydianiline, 2,2′-bis[4-(naphthalene-1-yl)phenyl]-4,4′-oxydianiline, and 2,2′-bis[4″-(diphenylamino)phenyl]-4,4′-oxydianiline), were successfully synthesized through four steps using p-chloronitrobenzene as a starting material. Highly organosoluble polyimides were obtained by the reaction of these diamines with 2′2 ′-bis[4′-(3″,4″,5″-trifluorophenyl)phenyl]-4,4′,5,5′-biphenyltetracarboxylic dianhydride via a conventional two-step chemical imidization method. All the polyimides were thoroughly characterized by Fourier transform infrared, ultraviolet, fluorescence, gel permeation chromatography, and thermogravimetric analysis. The effect of the fluorine atoms directly linked to the lateral phenyl rings showed excellent dissolution and strong fluorescence. The polyimides exhibited excellent thermal stability, with decomposition temperatures (at 10% weight loss) above 530°C and glass transition temperatures in the range of 258–320°C. These outstanding combined features ensured that these polyimides could be used as memory materials for advanced microelectronic applications.

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