Patent ID: 6261738
Filing Date: 2001-07-17
Classification: C07C,C07D,G03F,G03G,Y10S

Abstract:
A chemically amplified photoresist composition comprising,(a) a compound which cures upon the action of an acid or a compound whose solubility is increased upon the action of an acid; and(b) as photosensitive acid donor, at least one compound of the formula I, II or III ##STR124##whereinR.sub.1 is hydrogen, unsubstituted C.sub.1 -C.sub.12 alkyl; C.sub.1 -C.sub.12 alkyl which is substituted by C.sub.3 -C.sub.30 -cycloalkyl; or R.sub.1 is C.sub.3 -C.sub.30 cycloalkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.4 -C.sub.8 cycloalkenyl, C.sub.6 -C.sub.12 bicycloalkenyl, camphoryl; phenyl, which is unsubstituted or substituted by one or more of the radicals C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl-C.sub.1 -C.sub.3 -alkyl, halogen, phenyl, OR.sub.4, NR.sub.5 R.sub.6, SR.sub.7, SOR.sub.7, and/or SO.sub.2 R.sub.7, optionally the substituents OR.sub.4, SR.sub.7 and NR.sub.5 R.sub.6 form 5- or 6-membered rings, via the radicals R.sub.4, R.sub.5, R.sub.6 and/or R.sub.7, with further substituents on the phenyl ring or with one of the carbon atoms of the phenyl ring;or R.sub.1 is naphthyl, anthracyl or phenanthryl, wherein the radicals naphthyl, anthracyl and phenanthryl are unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl, phenyl, OR.sub.4, NR.sub.5 R.sub.6, SR.sub.7, SOR.sub.7, and/or SO.sub.2 R.sub.7, optionally the substituents OR.sub.4, SR.sub.7 and NR.sub.5 R.sub.6 form 5- or 6-membered rings, via the radicals R.sub.4, R.sub.5, R.sub.6 and /or R.sub.7 with further substituents on the naphthyl, anthracyl or phenanthryl ring or with one of the carbon atoms of the naphthyl, anthracyl or phenanthryl ring;or R.sub.1 is a heteroaryl radical which is unsubstituted or substituted by C.sub.1 -C.sub.6 alkyl, phenyl, OR.sub.4, NR.sub.5 R.sub.6, SR.sub.7, SOR.sub.7, and/or SO.sub.2 R.sub.7, optionally the substituents OR.sub.4, SR.sub.7 and NR.sub.5 R.sub.6 form 5- or 6-membered rings, via the radicals R.sub.4, R.sub.5, R.sub.6 and/or R.sub.7 with further substituents on the heteroaryl ring or with one of the carbon atoms of the heteroaryl ring;wherein all radicals R.sub.1 with the exception of hydrogen can additionally be substituted by a group having a --O--C-bond or a --O--Si-bond which cleaves upon the action of an acid;R'.sub.1 is phenylene, naphthylene, ##STR125##diphenylene or oxydiphenylene, wherein these radicals are unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl; orR'.sub.1 is C.sub.1 -C.sub.12 alkylene or ##STR126##A is --O--, --S--, --NR.sub.4 --, --O(CO)--, --S(CO)--, --NR.sub.4 (CO)--, --SO--, --SO.sub.2 --, or --OSO.sub.2 --;A.sub.1 is C.sub.1 -C.sub.12 alkylene or C.sub.2 -C.sub.12 alkylene, which is interrupted by one or more --O--;R.sub.2 is halogen or C.sub.1 -C.sub.10 haloalkyl;R.sub.3 is C.sub.1 -C.sub.18 alkylsulfonyl, C.sub.1 -C.sub.10 haloalkylsulfonyl, camphorylsulfonyl, phenyl-C.sub.1 -C.sub.3 -alkylsulfonyl, C.sub.3 -C.sub.12 cycloalkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the groups cycloalkyl, phenyl, naphthyl, anthracyl and phenanthryl of the radicals C.sub.3 -C.sub.12 cycloalkylsulfonyl, phenyl-C.sub.1 -C.sub.3 alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl and phenanthrylsulfonyl are unsubstituted or substituted by one or more halogen, C.sub.1 -C.sub.4 haloalkyl, CN, NO.sub.2, C.sub.1 -C.sub.16 alkyl, phenyl, C.sub.1-C.sub.4 -alkylthio, OR.sub.4, COOR.sub.7, C.sub.1 -C.sub.4 alkyl-(OC)O--, R.sub.7 OSO.sub.2 -- and/or --NR.sub.5 R.sub.6 ;or R.sub.3 is C.sub.2 -C.sub.6 haloalkanoyl, halobenzoyl, or a group ##STR127##Y.sub.1, Y.sub.2 and Y.sub.3 independently of each other are O or S;R'.sub.3 is phenylenedisulfonyl, naphthylenedisulfonyl, ##STR128##diphenylenedisulfonyl, or oxydiphenylenedisulfonyl, wherein these radicals are unsubstituted or substituted by C.sub.1 -C.sub.12 alkyl; or R'.sub.3 is C.sub.2 -C.sub.12 alkylenedisulfonyl;X is halogen;R.sub.4 is hydrogen, phenyl, C.sub.1 -C.sub.18 alkyl which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 -alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 -alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C.sub.2 -C.sub.6 alkanoyl;or R.sub.4 is C.sub.2 -C.sub.18 alkyl which is interrupted by one or more --O--, and which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or by C.sub.2 -C.sub.6 alkanoyl;or R.sub.4 is C.sub.2 -C.sub.18 alkanoyl which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 alkanoyl; or R.sub.4 is C.sub.1 -C.sub.18 alkylsulfonyl which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 -alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 -alkanoyl;or R.sub.4 is phenylsulfonyl, or (4-methylphenyl)sulfonyl;R.sub.5 and R.sub.6 independently of each other are hydrogen orC.sub.1 -C.sub.18 alkyl which is unsubstituted or substituted by OH, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, phenylamino, phenylaminocarbonyl, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methyl-phenyl)sulfonyl and/or C.sub.1 -C.sub.6 alkanoyl;or R.sub.5 and R.sub.6 are C.sub.2 -C.sub.18 alkyl which is interrupted by one or more --O--, and which is unsubstituted or substituted by OH, C.sub.1 -C.sub.4 alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, phenylamino, phenylaminocarbonyl, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl and/or C.sub.1 -C.sub.6 alkanoyl;or R.sub.5 and R.sub.6 are C.sub.2 -C.sub.18 alkanoyl, which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 -alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, phenylamino, phenylaminocarbonyl, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 alkanoyl;or R.sub.5 and R.sub.6 are C.sub.1 -C.sub.18 alkylsulfonyl which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, phenylamino, phenylaminocarbonyl, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 alkanoyl;or R.sub.5 and R.sub.6 are phenyl, benzoyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;or R.sub.5 and R.sub.6, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring which may be interrupted by --O-- or by --NR.sub.4 --;R.sub.7 is hydrogen, phenyl,C.sub.1 -C.sub.18 alkyl which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 -alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 -alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 alkanoyl;or R.sub.7 is C.sub.2 -C.sub.18 alkyl which is interrupted by one or more --O-- and which unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 alkanoyl;or R.sub.7 is C.sub.2 -C.sub.18 alkanoyl which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 alkanoyl;or R.sub.7 is C.sub.1 -C.sub.18 alkylsulfonyl which is unsubstituted or substituted by phenyl, OH, C.sub.1 -C.sub.12 -alkoxy, C.sub.2 -C.sub.12 alkoxycarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.5 R.sub.6, C.sub.1 -C.sub.12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, and/or by C.sub.2 -C.sub.6 -alkanoyl;or R.sub.7 is phenylsulfonyl, or (4-methylphenyl)sulfonyl;R.sub.8, R.sub.9 and R.sub.10 independently of one another are C.sub.1 -C.sub.6 alkyl which is unsubstituted or substituted by halogen;or R.sub.8, R.sub.9 and R.sub.10 are phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or halogen;or R.sub.9 and R.sub.10 together are 1,2-phenylene or C.sub.2 -C.sub.6 alkylene which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl or halogen.