Synthesis and polymerization of N-(4-tetrahydropyranyl-oxyphenyl)maleimide

N-(4-Tetrahydropyranyl-oxy-phenyl)maleimide (THPMI) was prepared and polyme rized by radical or anionic initiators. THPMI could be polymerized by 2,2'- azobis(isobutyronitrile) (NBN) and potassium tert-butoxide. Radical polymer s (poly(THPMI)r) were obtained in 15-50% yields for AIBN in THF at 65 degre es C after 2-5 h. The yield of anionic polymers (poly(THPMI)a) obtained fro m potassium tert-butoxide in THF at 0 degrees C after 20 h was 91%. The mol ecular weights of poly(THPMI)r and poly(THPMI)a were M-n = 2750-3300 (M-w/M -n = 1.2-3.3) and M-n = 11300 (M-w/M-n = 6.0), respectively. The difference in molecular weights of the polymers was due to the differences in the ter mination mechanism of polymerization and the solubility of these polymers i n THF. The thermal decomposition temperatures were 205 and 365 degrees C. T he first decomposition step was based on elimination of the tetrahydropyran yl group from the poly(THPMI). Positive image patterns were obtained by che mical amplification of positive photoresist composed of poly(THPMI) and 4-m orpholinophenyl diazonium trifluoromethanesulfonate used as an acid generat or. (C) 1999 John Wiley & Sons, Inc.