Phenolic photosensitizers containing quinone diazide and acidic halide substituents
AssigneeHoechst Celanese Corporation
InventorsRobert E. Potvin, Jonas O. St. Alban, Chester J. Sobodacha
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Abstract
The invention relates to mixed ester photosensitive compounds and photosensitizer compositions comprised thereof. The photosensitive compounds and photosensitizer compositions are prepared by condensing phenolic compounds with a 1,2-naphthoquinonediazide-4-sulfonic acid halide and an organic acid halide in specific ratios. Photoresist compositions comprising the photosensitive compounds and photosensitizer compositions are also disclosed. The photosensitizer compositions exhibit excellent solution stablity and resistance to precipitation when formulated in alkali-soluble resin photoresist compositions. The photoresist compositions have improved shelf life.
Claims18
A photosensitive compound represented by the formulae (1), (2) or (3):
- ##STR37## wherein R is H, --X--R.sub.b or ##STR38## X is a single C--C bond, --O--, --S--, --SO.sub.2 --, ##STR39## n is 1 or 2, R.sub.a is H, --OH, --OY, --OZ, halogen or lower alkyl, with at least one R.sub.a radical being --0Y and at least one thereof being --OZ, R.sub.b is H, alkyl, aryl, substituted alkyl, or substituted aryl;
- ##STR40## wherein R.sub.1 is H, or ##STR41## R.sub.c is H, --OH, --OY or --OZ, with at least one R.sub.c radical being --OY and at least one thereof being --OZ;
- and ##STR42## wherein R.sub.2 is H, alkyl, aryl, substituted alkyl, or substituted aryl, Rd is --OH, --OY or --OZ with at least one R.sub.d radical being --OY and at least one thereof being --OZ;
- wherein y is 1,2-naphthoquinonediazide-4-sulfonyl and Z is --W--R.sub.3, where W is ##STR43## or --SO.sub.2 --, and R.sub.3 is alkyl, aryl, substituted alkyl or substituted aryl.
A photosensitizer composition comprising the condensation product of:
- (I) phenolic compound selected from the group consisting of:
- ##STR44## wherein R is H, --X--R.sub.b, or ##STR45## R.sub.a is H, --OH, halogen or lower alkyl, with at least two and not greater than six R.sub.a radicals being --OH, X is a single C--C bond, --O--, --S--, --SO.sub.2 --, ##STR46## n is 1 or 2, R.sub.b is H, alkyl, aryl, substituted alkyl or substituted aryl;
- ##STR47## wherein R.sub.1 is H or ##STR48## R.sub.c is H or --OH with at least two R.sub.c radicals being --OH;
- and ##STR49## wherein R.sub.2 is H, alkyl, aryl, substituted alkyl, or substituted aryl;
- and
- (II) a 1,2-naphthoquinonediazide-4-sulfonic acid (Diazo);
- and
- (III) an organic acid halide represented by the formula:
- W--R.sub.3
- wherein W is ##STR50## V is halogen and R.sub.3 is alkyl, aryl, substituted alkyl or substituted aryl;
- wherein the molar ratio of the amount of Diazo reacted to the amount of organic acid reacted is in the range of from about 1:1 to about 39:1.
Dependencies are inferred from the claim text.