Sulfonium compounds, their preparation and use

Abstract

Compounds of the formula (I), (Ia) or (Ib) wherein A.sub.1, and A.sup. is for example (II) is 1 or 2; X is C.sub.1-C.sub.4 alkylene or CO; Y is for example O, O(CO), O(CO)O, R.sub.1 is for example hydrogen, d-dsalkyl, C.sub.3-C.sub.30cycloalkyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or C.sub.3-C.sub.20heteroaryl, all of which optionally are substituted; R.sub.2 and R.sub.3 for example are C.sub.1-C.sub.10haloalkylene which is optionally substituted, or R.sub.2 and R.sub.3 are phenylene, which optionally is substituted; R.sub.4 is a group (A) or a group (B); R.sub.5 and R.sub.6 for example are C.sub.1-C.sub.20alkyl; or R.sub.4 and R.sub.5 or R.sub.4 and R.sub.6 together form a straight-chain C.sub.2-C.sub.6alkylene, R.sub.5 and R.sub.6 together form a straight-chain C.sub.2-C.sub.6alkylene; R.sub.7, R.sub.8, R.sub.9 and R.sub.10 ifor example are C.sub.1-C.sub.20alkyl; M for example is C.sub.1-C.sub.20alkylene, C.sub.2-C.sub.20alkenylene, C.sub.2-C.sub.20alkynylene; R.sub.25 and R.sub.26 are for example hydrogen, C.sub.1-C.sub.20alkyl; R.sub.27, R.sub.28, R.sub.29, R.sub.30 and R.sub.31 are for example hydrogen, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkenyl, C.sub.3-C.sub.20cycloalkyl, or two radicals R.sub.27 and R.sub.28, R.sub.28 and R.sub.29, R.sub.29 and R.sub.30 and/or R.sub.30 and R.sub.31 together form a straight-chain C.sub.2-C.sub.6alkylene, or R.sub.25 and R.sub.27 together form 1,2-phenylene, R.sub.33 and R.sub.34 for example are hydrogen, C.sub.1-C.sub.20alkyl; R.sub.35, R.sub.36 and R.sub.37 for example are hydrogen, C.sub.1-C.sub.20alkyl; are suitable as thermo-acid generators. ##STR00001##

Claims

1. A compound of the formula I, Ia or Ib ##STR00049## wherein A.sub.1.sup. is an anion selected from the group consisting of ##STR00050## A.sup. is an anion selected from the group consisting of ##STR00051## PF.sub.6.sup., SbF.sub.6.sup., BF.sub.4.sup., tetrakis(pentafluorophenyl)borate, fluoroalkylphosphate, pentafluorobenzenesulfonate, nitrobenzenesulfonate, di(alkoxycarbonyl)benzenesulfonate, perfluoroalkanesulfonate, difluoromethanedisulfonate, alkylsulfonate, tris(trifluoromethanesulfonyl)methide, bis(perfluoroalkanesulfonyl)imide and 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide; provided that at least one anion A.sup. is ##STR00052## and provided that the anions A.sub.1.sup. and A.sup. are not ##STR00053## n is 1 or 2; X is C.sub.1-C.sub.4alkylene or CO; X.sub.1 is CH.sub.2, CO, O, S, CF.sub.2O, SO.sub.2, SO.sub.2O, SO.sub.2N or (CO)O; Y is O, O(CO), O(CO)O, O(CO)NR.sub.11, O(CO)NR.sub.11(CO), OSO.sub.2, O(CS), or O(CS)NR.sub.11, in which for each of these the oxygen atom is directly bound to X; or is NR.sub.11, S, NR.sub.11(CO)O, NR.sub.11(CS)O, in which the N- or S-atom is directly bound to X; R.sub.1 is hydrogen, C.sub.1-C.sub.18alkyl, C.sub.2-C.sub.18alkyl which is interrupted by one or more of O, S, NR.sub.14, CO, O(CO) or NR.sub.14(CO), or is phenyl-C.sub.1-C.sub.3-alkyl or C.sub.1-C.sub.10haloalkyl, wherein said C.sub.1-C.sub.18alkyl, interrupted C.sub.2-C.sub.18alkyl, phenyl-C.sub.1-C.sub.3-alkyl or C.sub.1-C.sub.10haloalkyl are unsubstituted or are substituted by one or more identical or different Z.sub.1; or R.sub.1 is C.sub.2-C.sub.12alkenyl or C.sub.2-C.sub.18alkenyl which is interrupted by one or more of O, S, NR.sub.14, CO, O(CO), NR.sub.14(CO) or Z.sub.3, wherein said uninterrupted or interrupted C.sub.2-C.sub.12alkenyl is unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.1 is C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl, wherein said C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl is unsubstituted or substituted by one or more identical or different Z.sub.1 and wherein said unsubstituted or substituted C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl optionally is interrupted by one or more identical or different O, S, NR.sub.14, CO, O(CO) or NR.sub.14(CO); or R.sub.1 is phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or C.sub.3-C.sub.20heteroaryl wherein said phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, fluorenyl or C.sub.3-C.sub.20heteroaryl are unsubstituted or are substituted by one or more identical or different Z.sub.2; or R.sub.1 is NR.sub.12R.sub.13 or a monovalent C.sub.17-C.sub.50hydrocarbon group of steroid structure which optionally comprises one or more heteroatoms; Z.sub.3 is phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or C.sub.3-C.sub.20heteroarylene, wherein said phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or C.sub.3-C.sub.20heteroarylene are unsubstituted or substituted by one or more identical or different Z.sub.1; R.sub.2 and R.sub.3 independently of each other are C.sub.1-C.sub.10haloalkylene, C.sub.1-C.sub.10haloalkylene substituted by one or more identical or different Z.sub.1; or R.sub.2 and R.sub.3 are C.sub.1-C.sub.18alkylene, C.sub.3-C.sub.30cycloalkylene, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkylene, C.sub.2-C.sub.12alkenylene or C.sub.4-C.sub.30cycloalkenylene wherein said C.sub.1-C.sub.18alkylene, C.sub.3-C.sub.30cycloalkylene, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkylene, C.sub.2-C.sub.12alkenylene or C.sub.4-C.sub.30cycloalkenylene is uninterrupted or interrupted by one or more identical or different O, S, NR.sub.14, CO, O(CO) or NR.sub.14(CO) and wherein said uninterrupted or interrupted C.sub.1-C.sub.18alkylene, C.sub.3-C.sub.30cycloalkylene, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkylene, C.sub.2-C.sub.12alkenylene or C.sub.4-C.sub.30cycloalkenylene is unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.2 and R.sub.3 are phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or C.sub.3-C.sub.20heteroarylene, wherein said phenylene, naphthylene, anthracylene, phenanthrylene, biphenylene or C.sub.3-C.sub.20heteroarylene is unsubstituted or substituted by one or more identical or different Z.sub.2; or R.sub.2 and R.sub.3 independently of each other are a direct bond, provided that R.sub.2 and R.sub.3 are not both simultaneously a direct bond; R.sub.4 is a group ##STR00054## or a group ##STR00055## R.sub.5 and R.sub.6 independently of one another are unsubstituted C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.20alkyl substituted by one or more identical or different R.sub.2a, or C.sub.2-C.sub.20alkyl interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), wherein said interrupted C.sub.2-C.sub.20alkyl optionally is substituted by one or more identical or different R.sub.2a, or C.sub.2-C.sub.20alkenyl, C.sub.2-C.sub.20alkenyl substituted by one or more identical or different R.sub.2a, wherein said unsubstituted or substituted C.sub.2-C.sub.20alkenyl optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), or R.sub.5 and R.sub.6 are C.sub.2-C.sub.20alkynyl, C.sub.2-C.sub.20alkynyl substituted by one or more identical or different R.sub.2a, wherein said unsubstituted or substituted C.sub.2-C.sub.20-alkynyl optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), or R.sub.5 and R.sub.6 are C.sub.3-C.sub.20cycloalkyl, C.sub.3-C.sub.20cycloalkyl interrupted by one or more CO, and optionally substituted by one or more identical or different radicals R.sub.2b, or R.sub.5 and R.sub.6 are C.sub.3-C.sub.20heterocycloalkyl, C.sub.3-C.sub.20heterocycloalkyl interrupted by one or more CO and optionally substituted by one or more identical or different radicals R.sub.2b, or R.sub.5 and R.sub.6 are C.sub.6-C.sub.20aryl, C.sub.6-C.sub.20aryl substituted by one or more identical or different R.sub.2c, or R.sub.5 and R.sub.6 are C.sub.3-C.sub.20heteroaryl, C.sub.3-C.sub.20heteroaryl substituted by one or more identical or different R.sub.2c; or R.sub.4 and R.sub.5 or R.sub.4 and R.sub.6 together form a straight-chain C.sub.2-C.sub.6alkylene, straight-chain C.sub.2-C.sub.6-alkenylene or a (CH.sub.2).sub.aC.sub.6H.sub.4(CH.sub.2).sub.b, wherein said C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6-alkenylene and the alkylene moiety of (CH.sub.2).sub.aC.sub.6H.sub.4(CH.sub.2).sub.b optionally are substituted by one or more identical or different radicals R.sub.32 and wherein said unsubstituted or substituted C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6-alkenylene and the alkylene moiety of (CH.sub.2).sub.aC.sub.6H.sub.4(CH.sub.2).sub.b optionally are interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); or R.sub.5 and R.sub.6 together form a straight-chain C.sub.2-C.sub.6alkylene, a straight-chain C.sub.2-C.sub.6alkenylene, or a straight-chain (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d, wherein said C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene and the alkylene moiety of (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d optionally is substituted by one or more identical or different radicals R.sub.32 and wherein said C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene and the alkylene moiety of (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d optionally is fused to 1 or 2 phenyl rings; and wherein said C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene and the alkylene moiety of (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); a and b are an integer from 0 to 10 and the sum of a and b is 1 to 10; c and d are an integer from 0 to 10 and the sum of c and d is 1 to 10; R.sub.2a is F, Cl, Br, I, CN, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.3-C.sub.20cycloalkyl, C.sub.3-C.sub.20cycloalkyl substituted by one or more identical or different R.sub.2ab, wherein the unsubstituted or substituted C.sub.3-C.sub.20cycloalkyl optionally is interrupted by one or more CO, or R.sub.2a is C.sub.3-C.sub.20heterocycloalkyl, C.sub.3-C.sub.20heterocycloalkyl substituted by one or more identical or different R.sub.2ab, wherein the unsubstituted or substituted C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO, or R.sub.2a is C.sub.3-C.sub.20heteroaryl or C.sub.6-C.sub.10aryl, where said C.sub.3-C.sub.20heteroaryl or C.sub.6-C.sub.10aryl optionally are substituted by one or more identical or different R.sub.2ac; R.sub.2ab is F, Cl, Br, I, C.sub.1-C.sub.12-alkyl, C.sub.1-C.sub.12-haloalkyl, CN, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22 or CONR.sub.23R.sub.24; R.sub.2ac is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, or CONR.sub.23R.sub.24; R.sub.2b is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, CN, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.6-C.sub.10aryl or C.sub.3-C.sub.20heteroaryl where said C.sub.6-C.sub.10aryl or C.sub.3-C.sub.20heteroaryl optionally is substituted by one or more identical or different R.sub.2ac; R.sub.2c is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, phenyl, C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally are interrupted by one or more CO; R.sub.7, R.sub.8, R.sub.9 and R.sub.10 independently of one another are C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), substituted by one or more identical or different R.sub.2a, wherein said C.sub.1-C.sub.20alkyl or interrupted C.sub.2-C.sub.20alkyl optionally is substituted by one or more identical or different R.sub.2a; or R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are C.sub.2-C.sub.20alkenyl, C.sub.2-C.sub.20alkenyl interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), wherein said C.sub.2-C.sub.20alkenyl or interrupted C.sub.2-C.sub.20alkenyl optionally is substituted by one or more identical or different R.sub.2a; or R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are C.sub.2-C.sub.20alkynyl, C.sub.2-C.sub.20alkynyl interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), wherein said C.sub.2-C.sub.20alkynyl or interrupted C.sub.2-C.sub.20alkynyl optionally is substituted by one or more identical or different R.sub.2a; or R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are C.sub.3-C.sub.20cycloalkyl, C.sub.3-C.sub.20cycloalkyl interrupted by one or more CO, wherein said C.sub.3-C.sub.20cycloalkyl or interrupted C.sub.3-C.sub.20cycloalkyl optionally is substituted by one or more identical or different R.sub.2b; or R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are C.sub.3-C.sub.20heterocycloalkyl, C.sub.3-C.sub.20heterocycloalkyl interrupted by one or more CO, wherein said C.sub.3-C.sub.20heterocycloalkyl or interrupted C.sub.3-C.sub.20heterocycloalkyl optionally is substituted by one or more identical or different R.sub.2b; or R.sub.7, R.sub.8, R.sub.9 and R.sub.10 are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, wherein said C.sub.6-C.sub.20aryl and C.sub.3-C.sub.20heteroaryl optionally is substituted by one or more identical or different R.sub.2c; or R.sub.7 and R.sub.8 and/or R.sub.9 and R.sub.10 together form a straight-chain C.sub.2-C.sub.6alkylene, a straight-chain C.sub.2-C.sub.6alkenylene or a straight-chain (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d, wherein said C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene and the alkylene moiety of (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d optionally is substituted by one or more identical or different R.sub.32 and wherein said C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene and the alkylene moiety of (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d optionally is fused to 1 or 2 phenyl rings, and wherein said C.sub.2-C.sub.6alkylene, C.sub.2-C.sub.6alkenylene and the alkylene moiety of (CH.sub.2).sub.cC.sub.6H.sub.4(CH.sub.2).sub.d optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); M is C.sub.1-C.sub.20alkylene, C.sub.2-C.sub.20alkenylene, C.sub.2-C.sub.20alkynylene, wherein said C.sub.1-C.sub.20alkylene, C.sub.2-C.sub.20alkenylene or C.sub.2-C.sub.20alkynylene optionally is substituted by one or more identical or different R.sub.Ma, and wherein said unsubstituted or substituted C.sub.1-C.sub.20alkylene, C.sub.2-C.sub.20alkenylene or C.sub.2-C.sub.20alkynylene optionally is interrupted by one or more identical or different non-adjacent R.sub.Mi; or M is C.sub.3-C.sub.20cycloalkylene or C.sub.3-C.sub.20heterocycloalkylene, wherein said C.sub.3-C.sub.20cycloalkylene or C.sub.3-C.sub.20heterocycloalkylene optionally is interrupted by one or more CO, and wherein said uninterrupted or interrupted C.sub.3-C.sub.20cycloalkylene or C.sub.3-C.sub.20heterocycloalkylene optionally is substituted by one or more identical or different R.sub.Mb; or M is C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene, wherein said C.sub.6-C.sub.20arylene is selected from the group consisting of phenylen, napthylene, anthracenediyl, and phenanthrenediyl, and wherein said C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene optionally is substituted by one or more identical or different R.sub.Mc; R.sub.Mi is O, S, C(O), OC(O) or N(R.sub.N), or R.sub.Mi is C.sub.3-C.sub.20cycloalkylene, OC.sub.3-C.sub.20cycloalkylene, OC.sub.3-C.sub.20cycloalkylene-O or C.sub.3-C.sub.20heterocycloalkylene, wherein said C.sub.3-C.sub.20cycloalkylene, OC.sub.3-C.sub.20cycloalkylene, OC.sub.3-C.sub.20cycloalkylene-O or C.sub.3-C.sub.20heterocycloalkylene optionally is interrupted by one or more CO groups and wherein said uninterrupted or interrupted C.sub.3-C.sub.20cycloalkylene, OC.sub.3-C.sub.20cycloalkylene, OC.sub.3-C.sub.20cycloalkylene-O or C.sub.3-C.sub.20heterocycloalkylene optionally is substituted by one or more identical or different R.sub.Mib; or R.sub.Mi is C.sub.6-C.sub.20arylene, OC.sub.6-C.sub.20arylene, OC.sub.6-C.sub.20arylene-O, SC.sub.6-C.sub.20arylene, SC.sub.6-C.sub.20arylene-S or C.sub.3-C.sub.20heteroarylene, wherein said is C.sub.6-C.sub.20arylene, OC.sub.6-C.sub.20arylene, OC.sub.6-C.sub.20arylene-O, SC.sub.6-C.sub.20arylene, SC.sub.6-C.sub.20arylene-S or C.sub.3-C.sub.20heteroarylene optionally is substituted by one or more R.sub.Mib; R.sub.Ma is F, Cl, Br, I, CN, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22 or CONR.sub.23R.sub.24, C.sub.6-C.sub.10aryl or C.sub.3-C.sub.20heteroaryl wherein said C.sub.6-C.sub.10aryl or C.sub.3-C.sub.20heteroaryl optionally is substituted by one or more identical or different radicals selected from C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, F, Cl, Br, I, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22 or CONR.sub.23R.sub.24; R.sub.Mib is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22 or CONR.sub.23R.sub.24 or phenyl; R.sub.Mb is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, CN, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22 or CONR.sub.23R.sub.24, C.sub.6-C.sub.10aryl or C.sub.3-C.sub.20heteroaryl wherein said C.sub.6-C.sub.10aryl or C.sub.3-C.sub.20heteroaryl optionally is substituted by one or more identical or different radicals selected from the group consisting of C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, F, Cl, Br, I, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22 and CONR.sub.23R.sub.24; R.sub.Mc is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22 or CONR.sub.23R.sub.24, phenyl, C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO; R.sub.11 is hydrogen, C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl; or R.sub.11 is C.sub.2-C.sub.18alkyl which is interrupted by one or more of O, S, NR.sub.11a, CO, O(CO) or NR.sub.11a(CO); or R.sub.11 is C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl, wherein said C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl optionally is interrupted by one or more identical or different O, S, NR.sub.11a, CO, O(CO) or NR.sub.11a(CO); or R.sub.11 is phenyl, naphthyl, anthracyl, phenanthryl, biphenyl, heteroaryl, C.sub.1-C.sub.18alkanoyl, benzoyl, C.sub.2-C.sub.18alkoxycarbonyl, phenoxycarbonyl, C.sub.1-C.sub.18alkylsulfonyl or phenylsulfonyl; wherein the C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, C.sub.4-C.sub.30cycloalkenyl, phenyl-C.sub.1-C.sub.3-alkyl, interrupted C.sub.2-C.sub.18alkyl, interrupted C.sub.3-C.sub.30cycloalkyl, interrupted C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl, interrupted C.sub.4-C.sub.30cycloalkenyl, phenyl, naphthyl, anthracyl, phenanthryl, biphenyl, heteroaryl, C.sub.1-C.sub.18alkanoyl, benzoyl, C.sub.2-C.sub.18alkoxycarbonyl, phenoxycarbonyl, C.sub.1-C.sub.18alkylsulfonyl or phenylsulfonyl are unsubstituted or substituted one or more identical or different Z.sub.1; or R.sub.1 and R.sub.11, together with the nitrogen atom to which R.sub.11 is attached, form a 5-, 6- or 7-membered ring which optionally is interrupted by one or more O, NR.sub.11a or CO; R.sub.12 and R.sub.13 independently of each other are hydrogen, C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.18alkyl or C.sub.2-C.sub.18alkyl which is interrupted by one or more identical or different O, S, NR.sub.11a CO, O(CO) or NR.sub.11a(CO) and wherein said C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.18alkyl or interrupted C.sub.2-C.sub.18alkyl is unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.12 and R.sub.13 are C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl, wherein said C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl optionally is interrupted by one or more identical or different O, S, NR.sub.11a, CO, O(CO) or NR.sub.11a(CO) and wherein said uninterrupted or interrupted C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.8alkyl or C.sub.4-C.sub.30cycloalkenyl are unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.12 and R.sub.13 independently of each other are (CO)R.sub.21, CO)OR.sub.21 or Ar which is unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.12 and R.sub.13, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring which optionally is interrupted by one or more O, NR.sub.11a or CO; R.sub.11a is hydrogen, C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.18alkyl or C.sub.2-C.sub.18alkyl which is interrupted by one or more of O, S, CO or O(CO), wherein said C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.18alkyl or interrupted C.sub.2-C.sub.18alkyl is unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.11a is C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl wherein said C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl optionally is interrupted by one or more identical or different O, S, CO or O(CO) and wherein said uninterrupted or interrupted C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl is unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.11a is phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, C.sub.3-C.sub.20heteroaryl, C.sub.1-C.sub.18alkanoyl, benzoyl, C.sub.2-C.sub.18alkoxycarbonyl, phenoxycarbonyl, C.sub.1-C.sub.18alkylsulfonyl or phenylsulfonyl, wherein said phenyl, naphthyl, anthracyl, phenanthryl, biphenylyl, C.sub.3-C.sub.20heteroaryl, C.sub.1-C.sub.18alkanoyl, benzoyl, C.sub.2-C.sub.18alkoxycarbonyl, phenoxycarbonyl, C.sub.1-C.sub.18alkylsulfonyl or phenylsulfonyl is unsubstituted or substituted one or more identical or different Z.sub.2; R.sub.14 is hydrogen, Ar, C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.18alkyl or C.sub.2-C.sub.18alkyl which is interrupted by one or more identical or different O, S, NR.sub.11a, CO, O(CO) or NR.sub.11a(CO), wherein said Ar, C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.18alkyl or interrupted C.sub.2-C.sub.18alkyl is unsubstituted or substituted by one or more identical or different Z.sub.1; or R.sub.14 is C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl wherein said C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl optionally is interrupted by one or more identical or different O, S, NR.sub.11a, CO, O(CO) or NR.sub.11a(CO) and wherein said uninterrupted or interrupted C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl is unsubstituted or substituted by one or more identical or different Z.sub.1; Ar is phenyl, biphenylyl, fluorenyl, naphthyl, anthracyl, phenanthryl or heteroaryl, wherein said phenyl, biphenylyl, fluorenyl, naphthyl, anthracyl, phenanthryl or heteroaryl are unsubstituted or substituted one or more identical or different Z.sub.2; Z.sub.1 is Ar, OH, C.sub.1-C.sub.18alkyl, C.sub.1-C.sub.10haloalkyl, phenyl-C.sub.1-C.sub.3-alkyl, C.sub.3-C.sub.30cycloalkyl, halogen, NO.sub.2, CN, C.sub.1-C.sub.18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR.sub.12R.sub.13, C.sub.1-C.sub.12alkylthio, C.sub.2-C.sub.18alkoxycarbonyl, C.sub.2-C.sub.10haloalkanoyl, halobenzoyl, C.sub.1-C.sub.18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C.sub.1-C.sub.18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C.sub.1-C.sub.18alkanoyl, C.sub.1-C.sub.18alkanoyloxy, benzoyl and/or by benzoyloxy; Z.sub.2 is C.sub.1-C.sub.18alkyl, C.sub.2-C.sub.18alkyl which is interrupted by one or more of O, S, NR.sub.11a, CO, O(CO) or NR.sub.11a(CO); or Z.sub.2 is C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl, wherein said C.sub.3-C.sub.30cycloalkyl, C.sub.3-C.sub.30cycloalkyl-C.sub.1-C.sub.18alkyl or C.sub.4-C.sub.30cycloalkenyl optionally is interrupted by one or more identical or different O, S, NR.sub.11a, CO, O(CO) or NR.sub.11a(CO); or Z.sub.2 is C.sub.1-C.sub.10haloalkyl, C.sub.2-C.sub.12alkenyl, phenyl-C.sub.1-C.sub.3-alkyl, halogen, NO.sub.2, CN, (CO)R.sub.21, (CO)OR.sub.22, (CO)NR.sub.12R.sub.13, O(CO)R.sub.21, O(CO)OR.sub.22, O(CO)NR.sub.12R.sub.13, NR.sub.11a(CO)R.sub.21, NR.sub.11a(CO)OR.sub.21, NR.sub.11a(CO)NR.sub.12R.sub.13, OR.sub.20, NR.sub.12R.sub.13, SR.sub.11a, phenyl, biphenylyl, fluorenyl, naphthyl, anthracyl, phenanthryl and/or heteroaryl; R.sub.19 and R.sub.20 independently of one another are hydrogen, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally are interrupted by one or more CO; or R.sub.19 and R.sub.20 are C.sub.2-C.sub.20alkyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); or R.sub.19 and R.sub.20 are C.sub.1-C.sub.8-alkyl substituted by one or more identical or different R.sub.19a; or R.sub.19 and R.sub.20 are (CH.sub.2CH.sub.2O).sub.mH, (CH.sub.2CH.sub.2O).sub.m(CO)(C.sub.1-C.sub.8-alkyl), C.sub.2-C.sub.8-alkanoyl, C.sub.2-C.sub.8-haloalkanoyl, C.sub.3-C.sub.6-alkenoyl, benzoyl or benzoyl which is substituted by one or more identical or different F, Cl, Br, I, C.sub.1-C.sub.6-alkyl, OH or C.sub.1-C.sub.4-alkoxy; or R.sub.19 and R.sub.20 are phenyl, naphthyl, both of which optionally are substituted by one or more identical or different R.sub.19c; or R.sub.19 and R.sub.20 are phenyl or naphthyl which forms a 5- or 6-membered ring via the phenyl ring to which SR.sub.19 or OR.sub.20, respectively, is attached via a single bond, C.sub.1-C.sub.4alkylene, O, S, CO or NR.sub.23; m is 1-20; R.sub.19a is F, Cl, Br, I, OH, SH, CN, C.sub.3-C.sub.10cycloalkyl, C.sub.3-C.sub.20heterocycloalkyl, phenyl, C.sub.3-C.sub.6alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), O(CO)-phenyl, (CO)OH or (CO)O(C.sub.1-C.sub.8alkyl); R.sub.19c is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12haloalkyl, C.sub.1-C.sub.12alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.12alkylsulfanyl, phenylsulfanyl, (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2 or phenyl; R.sub.21 is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.12alkenyl, C.sub.1-C.sub.20-alkyl which is interrupted by one or more non-adjacent O, S, CO or N(R.sub.N); or R.sub.21 is C.sub.1-C.sub.8alkyl substituted by one or more identical or different R.sub.21a, or R.sub.21 is (CH.sub.2CH.sub.2O).sub.mH, (CH.sub.2CH.sub.2O).sub.m(CO)(C.sub.1-C.sub.8-alkyl), C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO; or R.sub.21 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, both of which optionally are substituted by one or more radicals identical or different R.sub.19c; R.sub.21a is F, Cl, Br, I, OH, SH, CN, phenyl, C.sub.3-C.sub.6alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), O(CO)-phenyl, (CO)OH or (CO)O(C.sub.1-C.sub.8alkyl); R.sub.22 is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.12alkenyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), or R.sub.22 is C.sub.1-C.sub.8alkyl substituted by one or more identical or different R.sub.22a, or R.sub.22 is (CH.sub.2CH.sub.2O).sub.mH, (CH.sub.2CH.sub.2O).sub.m(CO)(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.10cycloalkyl, C.sub.3-C.sub.20heteroycloalkyl, wherein said C.sub.3-C.sub.10cycloalkyl, C.sub.3-C.sub.20heteroycloalkyl optionally are interrupted by one or more CO; or R.sub.22 is phenyl or naphthyl, both of which optionally are substituted by one or more identical or different R.sub.19c; R.sub.22a is F, Cl, Br, I, OH, SH, CN, C.sub.3-C.sub.6alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), O(CO)-phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8-alkyl), phenyl or naphthyl, wherein said phenyl or naphthyl optionally are substituted by one or more identical or different R.sub.19c; R.sub.23 and R.sub.24 independently of one another are hydrogen, OR.sub.20, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.12alkenyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); or R.sub.23 and R.sub.24 are C.sub.1-C.sub.8-alkyl substituted by one or more identical or different R.sub.23a; or R.sub.23 and R.sub.24 are (CH.sub.2CH.sub.2O).sub.mH, (CH.sub.2CH.sub.2O).sub.m(CO)(C.sub.1-C.sub.8alkyl), C.sub.2-C.sub.8alkanoyl, C.sub.2-C.sub.8-haloalkanoyl, C.sub.3-C.sub.6-alkenoyl, benzoyl, benzoyl which is substituted by one or more identical or different F, Cl, Br, I, C.sub.1-C.sub.6alkyl, OH or C.sub.1-C.sub.4alkoxy; or R.sub.23 and R.sub.24 are C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally are interrupted by one or more CO; or R.sub.23 and R.sub.24 are phenyl or naphthyl both of which optionally are substituted by one or more identical or different R.sub.19c; R.sub.23a is F, Cl, Br, I, OH, SH, CN, phenyl, C.sub.3-C.sub.6alkenoxy, OCH.sub.2CH.sub.2CN, OCH.sub.2CH.sub.2(CO)O(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), O(CO)-phenyl, (CO)OH or (CO)O(C.sub.1-C.sub.8alkyl); or R.sub.23 and R.sub.24 together form a C.sub.2-C.sub.5alkylene group, which optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); R.sub.25 and R.sub.26 independently of one another are hydrogen, F, Cl, Br, I, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N) and wherein said uninterrupted C.sub.1-C.sub.20alkyl or interrupted C.sub.2-C.sub.20alkyl optionally is substituted by one or more identical or different R.sub.2a; or R.sub.25 and R.sub.26 are C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO and wherein said uninterrupted or interrupted C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is substituted by one or more identical or different R.sub.2b; or R.sub.25 and R.sub.26 are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, wherein said C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl optionally is substituted by one or more identical or different R.sub.2c; R.sub.27, R.sub.28, R.sub.29, R.sub.30 and R.sub.31 independently of one another are hydrogen, F, Cl, Br, I, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), wherein said C.sub.1-C.sub.20alkyl or interrupted C.sub.2-C.sub.20alkyl optionally is substituted one or more identical or different R.sub.2a; or R.sub.27, R.sub.28, R.sub.29, R.sub.30 and R.sub.31 are C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20alkynyl, wherein said C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20alkynyl optionally are substituted one or more identical or different R.sub.2a and wherein said unsubstituted or substituted C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20alkynyl optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); or R.sub.27, R.sub.28, R.sub.29, R.sub.30 and R.sub.31 are C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO and wherein said C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is substituted by one or more identical or different R.sub.2b; or R.sub.27, R.sub.28, R.sub.29, R.sub.30 and R.sub.31 are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, wherein said C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl optionally is substituted by one or more identical or different R.sub.2c; or two radicals R.sub.27 and R.sub.28, R.sub.28 and R.sub.29, R.sub.29 and R.sub.30 and/or R.sub.30 and R.sub.31 together form a straight-chain C.sub.2-C.sub.6alkylene or a straight-chain C.sub.2-C.sub.6alkenylene, wherein said C.sub.2-C.sub.6alkylene or C.sub.2-C.sub.6alkenylene optionally is substituted by one or more identical or different R.sub.32 and wherein said unsubstituted or substituted C.sub.2-C.sub.6alkenylene optionally is fused to 1 or 2 C.sub.6-C.sub.10aryl rings and wherein said unsubstituted or substituted, unfused or fused C.sub.2-C.sub.6alkenylene optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); R.sub.32 is F, Cl, Br, I, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20alkynyl; or R.sub.32 is C.sub.2-C.sub.20alkyl, C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20-alkynyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), wherein said uninterrupted C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkenyl, C.sub.2-C.sub.20alkynyl or said interrupted C.sub.2-C.sub.20alkyl, C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20-alkynyl optionally is substituted one or more identical or different R.sub.32a, or R.sub.32 is C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO and wherein said interrupted or uninterrupted C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is substituted by one or more identical or different R.sub.32b; or R.sub.32 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, both of which optionally are substituted by one or more identical or different R.sub.32c; R.sub.32a is F, Cl, Br, I, CN, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl wherein C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO and wherein said uninterrupted or interrupted C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is substituted by one or more identical or different R.sub.2ab; or R.sub.32a is phenyl or phenyl which is substituted by one or more identical or different R.sub.2ac; R.sub.32b is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12-haloalkyl, CN, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, phenyl or phenyl which is substituted by one or more identical or different R.sub.2ac; R.sub.32c is F, Cl, Br, I, C.sub.1-C.sub.12alkyl, C.sub.1-C.sub.12 haloalkyl, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, phenyl, C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO; R.sub.N is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.10alkanoyl, C.sub.6-C.sub.10aroyl, C.sub.1-C.sub.20alkylsulfonyl, C.sub.2-C.sub.20alkenylsulfonyl, C.sub.6-C.sub.10arylsulfonyl, C.sub.6-C.sub.10aryl, C.sub.3-C.sub.20heteroaryl, C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl wherein said C.sub.3-C.sub.10cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally are interrupted by one or more CO; R.sub.33 and R.sub.34 independently of one another are hydrogen, F, Cl, Br, I, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), wherein said C.sub.1-C.sub.20alkyl or interrupted C.sub.2-C.sub.20alkyl optionally is substituted by one or more R.sub.2a; or R.sub.33 and R.sub.34 are C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, where said C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is interrupted by one or more CO and wherein said C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is substituted by one or more identical or different R.sub.2b; or R.sub.33 and R.sub.34 are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, wherein C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl optionally is substituted by one or more identical or different R.sub.2c; R.sub.35, R.sub.36 and R.sub.37 independently of one another are hydrogen, F, Cl, Br, I, CN, NO.sub.2, SR.sub.19, OR.sub.20, COR.sub.21, COOR.sub.22, CONR.sub.23R.sub.24, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N), wherein said C.sub.1-C.sub.20alkyl or interrupted C.sub.2-C.sub.20alkyl optionally is substituted by one or more R.sub.2a; or R.sub.35, R.sub.36 and R.sub.37 are C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20alkynyl, wherein said C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20-alkynyl optionally is substituted by one or more identical or different R.sub.2a and wherein said unsubstituted or substituted C.sub.2-C.sub.20alkenyl or C.sub.2-C.sub.20alkynyl optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); or R.sub.35, R.sub.36 and R.sub.37 are C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl, wherein said C.sub.3-C.sub.20cycloalkyl or C.sub.3-C.sub.20heterocycloalkyl optionally is substituted by one or more identical or different R.sub.2b; or R.sub.35, R.sub.36 and R.sub.37 are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, wherein optionally is substituted by one or more identical or different R.sub.2c; or R.sub.35 and R.sub.36 together form straight-chain C.sub.2-C.sub.6alkylene or a straight-chain C.sub.2-C.sub.6alkenylene, wherein said C.sub.2-C.sub.6alkylene or C.sub.2-C.sub.6alkenylene optionally is substituted by one or more identical or different R.sub.32 and wherein said C.sub.2-C.sub.6alkylene or C.sub.2-C.sub.6alkenylene optionally is interrupted by one or more non-adjacent O, S, C(O) or N(R.sub.N); or two radicals R.sub.33 and R.sub.35, R.sub.33 and R.sub.37, R.sub.34 and R.sub.35 and/or R.sub.34 and R.sub.37 together form straight-chain C.sub.2-C.sub.6alkylene or C.sub.2-C.sub.6alkenylene, wherein said C.sub.2-C.sub.6alkylene or C.sub.2-C.sub.6alkenylene optionally is substituted by one or more identical or different R.sub.32 and wherein said unsubstituted or substituted C.sub.2-C.sub.6alkylene optionally is interrupted by one or more non-adjacent groups O, S, C(O), C(O)O, C(O)N(R.sub.N) or N(R.sub.N).

2. The compound of claim 1 having formula I or Ia, wherein A.sub.1.sup. is ##STR00056## A.sup. ##STR00057## provided that the anions A.sub.1.sup. and A.sup. are not ##STR00058## n is 2; X is methylene or CO; Y is O, O(CO) or OSO.sub.2, in which for each of these the oxygen atom is directly bound to X; R.sub.1 is hydrogen, C.sub.1-C.sub.8alkyl, or phenyl-C.sub.1-C.sub.3-alkyl, or R.sub.1 is phenyl which is unsubstituted or are substituted by one or more identical or different Z.sub.2; R.sub.4 is ##STR00059## R.sub.5 is unsubstituted C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.20alkyl substituted by one or more identical or different R.sub.2a, C.sub.3-C.sub.20cycloalkyl, C.sub.6-C.sub.20aryl or C.sub.6-C.sub.20aryl substituted by one or more identical or different R.sub.2c; R.sub.6 is unsubstituted C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.20alkyl substituted by one or more identical or different R.sub.2a, C.sub.6-C.sub.20aryl, C.sub.6-C.sub.20aryl substituted by one or more identical or different R.sub.2c; or R.sub.5 and R.sub.6 together form a straight-chain C.sub.2-C.sub.6alkylene; R.sub.2a is OR.sub.20, C.sub.3-C.sub.20heterocycloalkyl or C.sub.6-C.sub.10aryl; R.sub.2c is OR.sub.20; R.sub.7, R.sub.8, R.sub.9 and R.sub.10 independently of one another are C.sub.1-C.sub.20alkyl; M is C.sub.1-C.sub.20alkylene; Z.sub.2 is C.sub.1-C.sub.18alkyl; R.sub.20 is hydrogen; R.sub.25 and R.sub.26 are hydrogen; and R.sub.27, R.sub.28, R.sub.29, R.sub.30 and R.sub.31 are hydrogen; or two radicals R.sub.30 and R.sub.31 together form a straight-chain C.sub.2-C.sub.6alkenylene.

3. A heat-curable composition comprising (a) at least one compound which is capable of undergoing cationic polymerization; and (b) at least one compound of formula I, Ia or Ib according to claim 1.

4. The heat-curable composition according to claim 3, wherein the compound which is capable of undergoing cationic polymerization has at least one group selected from the group consisting of an epoxy group, oxetane group and vinyl ether group.

5. The heat-curable composition according to claim 3, where the compound which is capable of undergoing cationic polymerization is an epoxy resin.

6. The heat-curable composition according to claim 3, further comprising at least one component selected from the group consisting of solvent, reactive diluents, photoinitiators, photoacid generators, pigments, dispersants, ethylenically unsaturated compounds, binder being different from compounds (a) and different from ethylenically unsaturated compounds, sensitizer, thermal curing promoters being different from compounds of formula I, Ia and Ib, further additives and mixtures thereof.

7. A method for curing a cationic polymerizable composition, the method comprising applying a composition to a substrate, and exposing said composition to a treatment with heat, wherein said composition comprises (a) at least one compound which is capable of undergoing cationic polymerization; and (b) at least one sulfonium compound selected from compounds of the formula I, Ia and Ib according to claim 1.

8. A thermal acid generator compound comprising a compound of formula I, Ia or Ib according to claim 1.

9. A layer or a component of a flat panel display comprising the composition according to claim 3.

10. The layer or component according to claim 9, wherein the flat panel display is a liquid crystal display, OLED display or plasma display panel.

11. The layer or component according to claim 9, wherein the layer is an overcoat layer of a color filter or an insulating layer or a dielectric layer.

12. A pigmented paint, a nonpigmented paint, a printing ink, a printing plate, an adhesive, a dental composition or a gel coat comprising the composition according to claim 3.

13. The method according to claim 7, wherein the substrate is a layer or a component of a flat panel display.

14. The method according to claim 7, wherein the substrate is an overcoat layer of a color filter or an insulating layer or a dielectric layer.

15. A coated substrate which is coated on at least one surface with the composition according to claim 3.

16. The composition according to claim 3 further comprising one or more additives selected from the group consisting of hardeners, crosslinkers, reinforcing materials, dyes, flow control assistants, UV stabilizers, heat stabilizers, weatherability improvers, rheology modifiers, flame retardants, antioxidants, discoloration inhibitors, biocides, antistatic agents, plasticizers, lubricants, slip additives, wetting agents, film-forming assistants, adhesion promoters, corrosion inhibitors, antifreeze agents, defoamers, mold release agents, and photolatent acids.

17. The compound of claim 1 having formula I.

18. The compound of claim 1 having formula Ia.

19. The compound of claim 1 having formula Ib.

20. The compound of claim 1, which is selected from the group consisting of ##STR00060## ##STR00061## ##STR00062## ##STR00063## ##STR00064##

Description

APPLICATION EXAMPLES

Example A1

Thermal Curing Tests of Epoxy Formulation

(1) An epoxy formulation is prepared by mixing:

(2) TABLE-US-00002 25.0 parts by weight poly[(o-cresyl glycidyl ether)-co-formaldehyde] (Sigma-Ardrich) 75.0 parts by weight propylene glycol monomethyl ether acetate 0.5 parts by weight sulfonium sulfonate according to the examples

(3) The sulfonium sulfonate to be tested is added to a solution of poly[(o-cresyl glycidyl ether)-co-formaldehyde] and mixed. The mixture is applied to a silicon wafer using a spin coater (1H-DX2, MIKASA). The solvent is removed by heating at 80 C. for 2 min in a convection oven. The thickness of the dry film is approximately 1.2 m. The coating is further baked at 150 C. for 60 min or 180 C. for 60 min. The conversion of the epoxy group in baking is determined by measuring the IR absorption at 910 cm.sup.1 with a FT-IR spectrometer (FT-720, HORIBA) before and after baking. The higher the conversion, the more active is the tested sulfonium sulfonate. The results of the tests are given in table 2.

(4) The formulations comprising the compounds of the comparative examples 1 and 2 were processed in the same manner as described above, except that the content of C2 in the formulation instead of 0.5 part by weight was 1 part by weight.

(5) TABLE-US-00003 TABLE 2 Epoxy conversion (%) Compound 150 C. for 60 min 180 C. for 60 min S1 94.4 100.0 S2 93.8 99.0 S3 95.4 98.3 S4 94.2 100.0 S5 95.0 100.0 S6 97.4 99.6 S7 98.1 99.0 S8 92.6 99.5 S9 92.2 99.5 S10 94.8 99.7 S11 96.6 100.0 S12 95.5 100.0 S13 94.3 100.0 S14 93.9 99.5 S15 95.5 99.6 S16 82.9 99.2 S17 96.8 99.7 S18 97.7 99.7 S19 97.7 99.2 S20 91.3 99.6 S21 90.4 98.8 S22 90.8 98.6 S23 97.5 99.1 S24 98.0 100.0 S25 97.1 100.0 S26 98.8 98.8 S27 100.0 98.7 S28 100.0 99.7 S29 98.8 99.5 C1 80.2 88.1 C2 16.1 20.9 San-Aid SI-80, product of Sanshin Chemical Industry Co., Ltd San-Aid SI-110L, product of Sanshin Chemical Industry Co., Ltd