Synthesis and Application of polymers Containing Pendant Vinyl Ether Moiety Using Phase Transfer Catalysis

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Syntheses of polymers containing pendant vinyl ether moiety using phase transfer catalysis and applications of the resulting polymers were investigated. Polymer containing pendant vinyl ether moiety (P-1) was synthesized by the elimination reaction of poly(epichlorohydrin) (PECH) with potassium hydroxide or potassium tert-buthoxide using phase transfer catalysis under mild reaction conditions, and the resulting polymer decomposed by the irradiation of UV light using photo-generated cataionic catalyst (PGCC). However, the Tg of P-1 was low. Accordingly, synthesis of high Tg polymer (P-3) containing vinyl ether moiety and bulky substituent group was carried out by the elimination and substitution reactions of PECH using phase transfer catalysis. Although P-3 with PGCC decomposed by the irradiation of UV light, P-3 with aromatic bis-azide or di-thiol compounds gave the crosslinked gel compounds by the irradiation. This result indicates that P-3 can be applied to positive and negative types photoresists by the selection of the catalyst or photosensitizer. P-1 produced new optically active polymer containing pendant amino acid moiety by photochemical addition reaction with N-acetyl-L-cysteine using benzophenone as a photosensitizer in THF. A new polymer (P-4) containing pendant vinyl ether moiety was also prepared with about 80 mol-% conversion by the substitution reaction of poly(vinyl phenol) with 2-chloroethyl vinyl ether using phase transfer catalysis, and the photosensitivity of the resulting polymer with bis-azide or di-thiol compounds was examined. This result indicates that P-4 has high photosensitivity, and can be applied to negative type photo-resist.