US2008286693A1PendingUtilityA1
Sulfonate derivatives and the use thereof as latent acids
Est. expiryFeb 6, 2022(expired)· nominal 20-yr term from priority
G03F 7/0392G03F 7/0037G03F 7/0045Y10S430/114G03F 7/001C07C 323/66G03F 7/0758G03F 7/038G03F 7/0397C07C 381/00G03F 7/0382
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Claims
Abstract
Chemically amplified photoresist compositions 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) a compound of the formula Ia, Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, Vb or VIa wherein n is 1 or 2; m is 0 or 1; X 0 is —[CH 2 ] h —X or —CH═CH 2 ; h is 2, 3, 4, 5 or 6; R 1 , when n is 1, is for example optionally substituted phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl; R 1 , when n is 2, is for example optionally substituted phenylene or naphthylene; R 2 for example has one of the meanings of R 1 ; X is for example —OR 20 , —NR 21 R 22 , —SR 23 ; X′ is —X 1 -A 3 -X-; X 1 and X 2 are for example —O—, —S— or a direct bond; A 3 is e.g. phenylene; R 3 has for example one of the meanings given for R 1 ; R 4 has for example one of the meaning given for R 2 ; R 5 and R 6 e.g. are hydrogen; G i.a. is —S— or —O—; R 7 when n is 1, e.g. is phenyl, optionally substituted, when n is 2, is for example phenylene; R 8 and R 9 e.g. are C 1 -C 18 alkyl; R 10 has one of the meanings given for R 7 ; R 11 i.a. is C 1 -C 18 alkyl; R 12 , R 13 , R 14 , R 15 R 16 , R 17 and R 18 for example are hydrogen or C 1 -C 18 alkyl; R 20 , R 21 , R 22 and R 23 i.a. are phenyl or C 1 -C 18 alkyl; give high resolution with good resist profile.
Claims
exact text as granted — not AI-modified1 . A compound of the formula Ia, Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, Vb or VIa
n is 1 or 2;
m is 0 or 1;
X 0 is —[CH 2 ] h —X or —CH═CH 2 ;
h is 2, 3, 4, 5 or 6;
R 1 when n is 1, is phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl,
all of which are optionally substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or are substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , optionally the substituents —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 form 5-, 6- or 7-membered rings, via the radicals R 19 , R 20 , R 21 , R 22 and/or R 23 , with further substituents on the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring;
or R 1 is hydrogen, with the proviso that R 2 is not simultaneously hydrogen;
or R 1 is C 1 -C 18 alkyl; or is C 2 -C 18 alkyl which is interrupted by one or more C 3 -C 30 cycloalkylene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —S(CO)—, —NR 23 (CO)—, —SO—, —SO 2 —, or —OSO 2 —; optionally the radicals C 1 -C 18 alkyl and C 2 -C 18 alkyl are substituted by one or more C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 1 is C 3 -C 30 cycloalkyl, optionally interrupted by one or more —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, or —NR 23 (CO)—, and which is unsubstituted or substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 1 is C 1 -C 8 haloalkyl, C 2 -C 12 alkenyl, C 4 -C 30 cycloalkenyl, camphoryl;
or if m is 0, R 1 additionally is CN, C 2 -C 6 alkoxycarbonyl or phenoxycarbonyl, wherein C 2 -C 6 alkoxycarbonyl and phenoxycarbonyl optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or are substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
R 1 , when n is 2, is phenylene, naphthylene,
diphenylene, oxydiphenylene or
wherein these radicals are unsubstituted or substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , or R 1 is a direct bond
wherein all radicals R 1 with the exception of hydrogen and direct bond 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;
A 1 is a direct bond, C 1 -C 18 alkylene, —O—, —S—, —NR 23 —, —O(CO)—, —S(CO)—, —NR 23 (CO)—, —SO—, —SO 2 — or —OSO 2 —;
A 2 is a direct bond, C 1 -C 18 alkylene; or is C 2 -C 18 alkylene which is interrupted by one or more C 3 -C 30 cycloalkylene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —S(CO)—, —NR 23 (CO)—, —SO—, —SO 2 —, —OSO 2 — or —Ar 2 —; optionally the radicals C 1 -C 18 alkylene and C 2 -C 18 alkylene are substituted by one or more C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or A 2 is C 3 -C 30 cycloalkylene, optionally interrupted by one or more —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, or —NR 23 (CO)—, and which is unsubstituted or substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or A 2 is phenylene, naphthylene, wherein these radicals optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
R 2 has one of the meanings of R 1 or is C 2 -C 18 alkanoyl; benzoyl that is unsubstituted or substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 2 is NO 2 ; or R 2 is S(O) p C 1 -C 18 alkyl, S(O) p —C 6 -C 12 aryl, SO 2 O—C 1 -C 18 alkyl, SO 2 O—C 6 -C 10 aryl, diphenyl-phosphinoyl, all of which optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or are substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 1 and R 2 together form a 5-, 6- or 7-membered ring which is unsubstituted or substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or is substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ; and said 5-, 6- or 7-membered ring may additionally be interrupted by C 1-18 alkylene, C 3 -C 30 cycloalkylene, C 1 -C 8 haloalkylene, C 2 -C 12 alkenylene, C 4 -C 30 cycloalkenylene, phenylene, naphthalene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —NR 23 (CO)—, —S(CO)—, —SO—, —SO 2 —, or —OSO 2 —, and to said 5-, 6- or 7-membered ring optionally are fused one or more benzo radicals;
p is 1 or 2;
X is —O(CO)R 24 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 24 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 , —OSO 2 R 19 , or the groups
X′ is -X 1 -A 3 -X 2 -;
X 1 and X 2 independently of each other are —O(CO)—, —O(CO)O—, —O(CO)NR 23 —, —NR 23 (CO)—, —NR 23 (CO)O—, —O—, —NR 23 —, —S—, —SO—, —SO 2 —, —OSO 2 —,
or X 1 and X 2 are a direct bond, with the proviso that X 1 and X 2 are not both simultaneously a direct bond;
A3 is phenylene, naphthylene,
diphenylene, oxydiphenylene or
wherein these radicals are unsubstituted or substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , or A 3 is a direct bond,
R 3 has one of the meanings given for R 1 ; or R 3 is C 2 -C 18 alkanoyl; benzoyl which optionally is substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 3 is NO 2 ; or R 3 is S(O) p C 1 -C 18 alkyl, S(O) p —C 6 -C 12 aryl, SO 2 O—C 1 -C 18 alkyl, SO 2 O—C 6 -C 10 aryl, diphenyl-phosphinoyl, all of which optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or is substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
R 4 has one of the meaning given for R 2 , or R 3 and R 4 together form a 5-, 6- or 7-membered ring which optionally is substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or said 5-, 6- or 7-membered ring is substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
and said 5-, 6- or 7-membered ring optionally additionally is interrupted by C 1-18 alkylene, C 3 -C 30 cycloalkylene, C 1 -C 8 haloalkylene, C 2 -C 12 alkenylene, C 4 -C 30 cycloalkenylene, phenylene, naphthalene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —NR 23 (CO)—, —S(CO)—, —SO—, —SO 2 —, or —OSO 2 —;
and optionally one or more benzo radicals are fused to said 5-, 6- or 7-membered ring;
R 5 and R 6 independently of each other are hydrogen, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or R 5 and R 6 are halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 5 and R 6 together are —C(R 30 )═C(R 31 )—C(R 32 )═C(R 33 )— or —(CO)NR 23 (CO)—;
G is —S—, —O—, —NR 23 —, or a group of formula Z 1 , Z 2 , Z 3 or Z
R 7 when n is 1, is phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl,
all of optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)— or —NR 23 (CO)—; or are substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , optionally the substituents —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 form 5-, 6- or 7-membered rings, via the radicals R 19 , R 20 , R 21 , R 22 and/or R 23 , with further substituents on the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring;
or R 7 is C 1 -C 18 alkyl; or is C 2 -C 18 alkyl which is interrupted by one or more C 3 -C 30 cycloalkylene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —S(CO)—, —NR 23 (CO)—, —SO—, —SO 2 —, or —OSO 2 —; optionally the radicals C 1 -C 18 alkyl and C 2 -C 18 alkyl are substituted by one or more C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 7 is C 3 -C 30 cycloalkyl, optionally interrupted by one or more —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, or —NR 23 (CO)—, and optionally substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 7 is hydrogen, C 1 -C 8 haloalkyl, —OR 20 , —NR 21 R 22 , —NR 23 (CO)R 19 , —SR 23 , C 2 -C 12 alkenyl, C 4 -C 30 cycloalkenyl, camphoryl; and
R 7 , when n is 2, is phenylene, naphthylene,
diphenylene, oxydiphenylene or
wherein these radicals are optionally substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , or R 7 is a direct bond,
wherein all radicals R 7 with the exception of hydrogen and direct bond optionally additionally are substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid;
A4 is a direct bond, C 1 -C 18 alkylene, —O—, —S— or —NR 23 —;
R 8 and R 9 independently of each other are C 1 -C 18 alkyl; or are C 2 -C 18 alkyl which is interrupted by one or more C 3 -C 30 cycloalkylene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —S(CO)—, —NR 23 (CO)—, —SO—, —SO 2 —, —OSO 2 — or —Ar 2 —; optionally the radicals C 1 -C 18 alkyl and C 2 -C 18 alkyl are substituted by one or more C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 8 and R 9 are C 3 -C 30 cycloalkyl, optionally interrupted by one or more —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, or —NR 23 (CO)—, and optionally substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 8 and R 9 are hydrogen, halogen, C 1 -C 8 haloalkyl, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 8 and R 9 , if appropriate, together with C 1 -C 4 alkylene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —NR 23 (CO)— form a 5-, 6-, or 7-membered ring;
or R 7 and R 8 , if appropriate, together with C 1 -C 3 alkylene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —NR 23 (CO)— form a 5-, 6-, or 7-membered ring;
R 10 has one of the meanings given for R 7 ;
R 11 is C 1 -C 18 alkyl; or C 2 -C 18 alkyl which is interrupted by one or more C 3 -C 30 cycloalkylene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —S(CO)—, —NR 23 (CO)—, —SO—, —SO 2 —, —OSO 2 — or —Ar 2 —; optionally the radicals C 1 -C 18 alkyl and C 2 -C 18 alkyl are substituted by one or more C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 11 is C 3 -C 30 cycloalkyl, optionally interrupted by one or more —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, or —NR 23 (CO)—, and optionally substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
or R 11 is hydrogen, C 1 -C 8 haloalkyl, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 or —SO 2 R 19 ;
or R 10 and R 11 together form a 5-, 6- or 7-membered ring which optionally is substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or said 5-, 6- or 7-membered ring is substituted by halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ; and said 5-, 6- or 7-membered ring optionally additionally is interrupted by C 1 -C 12 alkylene, C 3 -C 30 cycloalkylene, C 1 -C 8 haloalkylene, C 2 -C 12 alkenylene, C 4 -C 30 cycloalkenylene, phenylene, naphthalene, —O—, —S—, —NR 23 —, —(CO)—, —O(CO)—, —NR 23 (CO)—, —S(CO)—, —SO—, —SO 2 —, or —OSO 2 —; and to said 5-, 6- or 7-membered ring optionally are fused one or more benzo radicals;
with the provisos that,
(1) if h is 2, X′ is -X 1 -A3-X 2 - and X 1 , X 2 and A 3 all are a direct bond, then R 10 and R 11 do not form a ring interrupted by —CO—;
(2) if X 0 is —CH═CH 2 and R 11 is methyl, then R 10 is not phenyl or naphthyl; and
(3) if X 0 is —CH═CH 2 or if X 0 is —[CH 2 ] h —X, X is OR 20 and R 20 is methyl, then R 10 and R 11 , together do not form 5-, 6- or 7-membered rings which are interrupted by —CO—;
R 12 , R 13 , R 14 and R 15 independently of each other are hydrogen, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or R 12 , R 13 , R 14 and R 15 are halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ; optionally the substituents R 12 , R 13 , R 14 and/or R 15 form 5-, 6- or 7-membered rings or fused rings, via the radicals R 12 , R 13 , R 14 and/or R 15 with further substituents on the phenyl to which R 12 , R 13 , R 14 and R 15 are bonded, or with one of the carbon atoms of said phenyl ring;
wherein all radicals radicals R 12 , R 13 , R 14 and/or R 15 with the exception of hydrogen optionally additionally are substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid;
R 16 , R 17 and R 18 independently of each other are hydrogen, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or R 16 , R 17 and R 18 are halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , optionally the substituents R 16 , R 17 , and/or R 18 form 5-, 6- or 7-membered rings or fused rings, via the radicals R 16 , R 17 , and/or R 18 with further substituents on the phenyl ring to which R 16 , R 17 and R 18 are bonded or with one of the carbon atoms of said phenyl ring;
wherein all radicals radicals R 16 , R 17 , and/or R 18 with the exception of hydrogen optionally additionally are substituted by a group having a —O—C-bond or a —O—Si-bond which cleaves upon the action of an acid;
with the proviso that
(4) R 16 , R 17 and R 18 are not all simultaneously hydrogen, if X 0 is —CH═CH 2 ;
R 19 is phenyl, naphthyl, C 3 -C 30 cycloalkyl, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 2 -C 12 alkenyl, C 4 -C 30 cycloalkenyl; or is C 2 -C 18 alkyl which is interrupted by one or more —O—; or is C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—;
all of which optionally are substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy;
or R 19 is hydrogen;
R 20 is phenyl, naphthyl, C 3 -C 30 cycloalkyl, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 2 -C 12 alkenyl, C 4 -C 30 cycloalkenyl; or is C 2 -C 18 alkyl which is interrupted by one or more —O—; or is C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)— or —NR 23 (CO)—; or is C 2 -C 18 alkanoyl, or is benzoyl, or is C 1 -C 18 alkylsulfonyl,
all of which optionally are substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy;
or R 20 is hydrogen, phenylsulfonyl, (4-methylphenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
R 21 , R 22 and R 23 independently of each other are phenyl, naphthyl, C 3 -C 30 cycloalkyl, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 2 -C 12 alkenyl, C 4 -C 30 cycloalkenyl; or are C 2 -C 18 alkyl which is interrupted by one or more —O—; or are C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or are C 2 -C 18 alkanoyl, benzoyl or C 1 -C 18 alkylsulfonyl,
all of which optionally are substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkyl-sulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy;
or R 21 , R 22 and R 23 independently of each other are hydrogen, phenylsulfonyl, (4-methyl-phenyl)sulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
or R 21 and R 22 , together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered ring which optionally is interrupted by —O— or by —NR 23 —;
with the provisos that
(5) if m is 1, X 0 is —[CH 2 ] h —X, X is OR 20 or NR 21 R 22 and R 20 is hydrogen, or R 2 , and R 22 both are hydrogen, then R 1 and R 2 are not both simultaneously p-tolyl or p-chlorophenyl;
(6) if m is 0, X 0 is —[CH 2 ] h —X, X is NR 21 R 22 and R 2 , and R 22 both are the same and are alkyl, which is interrupted by 0, then R 1 is not thienyl;
(7) if X 0 is —[CH 2 ] h —X, X is OR 20 , R 20 is ethyl and R 8 and R 9 both are hydrogen, then R 7 is not propyl;
(8) if X 0 is —CH═CH 2 , R 8 and R 9 both are hydrogen, n is 1, R 7 is NR 21 R 22 and R 21 is hydrogen, then R 22 is not n-C 3 H 7 , i-C 3 H 7 or cyclohexyl and R 21 and R 22 are not both simultaneously alkenyl;
R 24 is phenyl, naphthyl, C 3 -C 30 cycloalkyl, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 4 -C 30 cycloalkenyl; or is C 2 -C 18 alkyl which is interrupted by one or more —O—, or is C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—;
all of which are unsubstituted or substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 -haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 halo-alkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy;
or R 24 is hydrogen;
or R 23 and R 24 together with the N-atom to which they are attached form a 5-, 6- or 7-membered ring which optionally is interrupted by —CO— or —O— and which additionally optionally is fused with one or more benzo rings;
R 25 , R 26 and R 27 independently of each other are hydrogen; or are phenyl or naphthyl, both of which optionally are substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkyl-sulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy; or R 25 , R 26 and R 27 are C 3 -C 18 alkenyl or C 3 -C 18 alkynyl; or R 25 , R 26 and R 27 are C 1 -C 18 alkyl, C 2 -C 18 alkyl which is interrupted by one or more —O—, and wherein the radicals C 1 -C 18 alkyl and C 2 -C 18 alkyl are optionally substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy; or R 25 and R 26 , if appropriate together with C 1 -C 2 alkylene, —O—, —S—, or —CO—, form a fused ring; or R 25 , R 26 and R 27 , if appropriate together with C 1 -C 2 alkylene, —O—, —S—, or —CO—, form a 5-, 6-, or 7-membered ring; or R 25 , R 26 and R 27 together with the N + -atom to which they are bonded form a group
R 28 and R 29 independently of each other are phenyl which optionally is substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy; or R 28 and R 29 independently of each other are C 1 -C 18 alkyl, C 2 -C 18 alkyl which is interrupted by one or more —O—, and wherein the radicals C 1 -C 18 alkyl and C 2 -C 18 alkyl are optionally substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy;
or R 28 and R 29 , if appropriate together with C 1 -C 2 alkylene, —O—, —S—, or —CO—, form a fused ring; or R 28 and R 29 , if appropriate together with C 1 -C 2 alkylene, —O—, —S—, or —CO—, form a 5-, 6- or 7-membered ring;
R 30 , R 31 , R 32 and R 33 are independently of each other hydrogen, halogen, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, C 1 -C 8 haloalkyl, CN, NO 2 , C 2 -C 18 alkanoyl, benzoyl, phenyl, —S-phenyl, OR 20 , SR 23 , NR 21 R 22 , C 2 -C 6 alkoxycarbonyl, phenoxycarbonyl, S(O) p C 1 -C 18 alkyl, unsubstituted or C 1 -C 18 alkyl-substituted S(O) p —C 6 -C 12 aryl, SO 2 O—C 1 -C 18 alkyl, SO 2 O—C 6 -C 10 aryl or NHCONH 2 ;
R 34 and R 35 independently of each other have one of the meanings given for R 5 ;
or R 34 and R 35 together are —CO—NR 23 CO—; or R 34 and R 35 together are —C(R 30 )═C(R 31 )—C(R 32 )═C(R 33 )—;
Ar 1 is phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl,
all of which optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl; C 3 -C 30 cycloalkyl which is interrupted by one or more —O—, —S—, —NR 23 —, —O(CO)—, or —NR 23 (CO)—; or are substituted by halogen, —NO 2 , —CN, phenyl, —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , optionally the substituents —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 form 5-, 6- or 7-membered rings, via the radicals R 19 , R 20 , R 21 , R 22 and/or R 23 , with further substituents on the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring or with one of the carbon atoms of the phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl ring;
Ar 2 is phenylene, naphthylene,
diphenylene, oxydiphenylene or
wherein these radicals optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 , optionally the substituents —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 form 5-, 6- or 7-membered rings, via the radicals R 19 , R 20 , R 21 , R 22 and/or R 23 , with further substituents on these radicals or with one of the carbon atoms of these radicals;
M + is
Li + , Na + , K + , Cs + , ½Mg 2+ , ½Ca 2+ or ½Ba 2+ ;
L − is F − , Cl − , Br − , I − , HSO 4 − , ½SO 4 2− , NO 3 − ,
ClO 4 − , BF 4 − , PF 6 − , AsF 6 − , SbF 6 − (R 50 SO 2 ) 3 C − or (R 50 SO 2 ) 2 N − ;
R 36 , R 37 , R 38 and R 39 have one of the meanings given for R 25 , R 26 and R 27 ;
R 40 , R 41 and R 42 have one of the meanings given for R 28 and R 29 ;
R 43 and R 44 independently of each other are phenyl, which optionally is substituted by one or more Ar 1 , OH, C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, C 1 -C 12 alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, —NR 21 R 22 , C 1 -C 12 alkylthio, C 2 -C 12 alkoxycarbonyl, C 2 -C 8 haloalkanoyl, halobenzoyl, C 1 -C 12 alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C 1 -C 12 alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C 2 -C 12 alkanoyl, C 2 -C 12 alkanoyloxy, benzoyl and/or by benzoyloxy; or R 43 and R 44 , if appropriate together with C 1 -C 2 alkylene, —O—, —S—, or —CO—, form a fused ring;
R 45 is C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, camphoryl, phenyl-C 1 -C 3 alkyl, C 3 -C 30 cycloalkyl, C 4 -C 30 cycloalkenyl, phenyl, naphthyl, anthracyl or phenanthryl; all of which optionally are substituted by one or more C 1 -C 18 alkyl, C 1 -C 8 haloalkyl, C 3 -C 30 cycloalkyl, halogen, —NO 2 , —CN, —Ar 1 , —(CO)R 19 , —(CO)OR 20 , —(CO)NR 21 R 22 , —O(CO)R 19 , —O(CO)OR 20 , —O(CO)NR 21 R 22 , —NR 23 (CO)R 19 , —NR 23 (CO)OR 20 , —OR 20 , —NR 21 R 22 , —SR 23 , —SOR 19 , —SO 2 R 19 and/or —OSO 2 R 19 ;
R 46 and R 47 independently of one another have one of the meanings given for R 5 ; or R 46 and R 47 together are —CO—NR 23 —CO— or —C(R 30 )═C(R 31 )—C(R 32 )═C(R 33 )—;
R 48 and R 49 independently of one another have on of the meanings given for R 5 , or R 48 and R 49 together are —CO—NR 23 —CO— or —C(R 30 )═C(R 31 )—C(R 32 )═C(R 33 )—;
R 50 is C 1 -C 8 -perfluoroalkyl;
Q 1 is —CR 35 — or —N—; and
Q 2 is —CH 2 —, —S—, —O— or —NR 23 —.
2 . A compound of the formula Ia, Ib, IIa or IIb according to claim 1 .
3 . A compound of the formula Ia, Ib, IIa or IIb according to claim 1 , wherein
m is 0; R 2 is C 1 -C 8 haloalkyl or —CN; R 4 is —CN; G is —S— or a group of formula Z 1 .
4 . A 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 Ia, Ib, IIa, IIb, IIIa, IIIb, IVa, IVb, Va, Vb or VIa according to claim 1 .Cited by (0)
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