Oxime derivatives and use thereof as latent acids

A compound of the formula I, II or III

• wherein
• R1 is C1-C18alkylsulfonyl or phenylsulfonyl, both of which optionally are substituted by one or more C1-C18alkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl;
• C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• or are substituted by NO2, CN, Ar2, (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7 and/or OSO2R7;
• or R1 is camphorylsulfonyl, phenyl-C1-C3alkylsulfonyl, C3-C30cycloalkylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl, wherein the camphorylsulfonyl, phenyl-C1-C3alkylsulfonyl, C3-C30cycloalkylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl are optionally substituted by one or more C1-C18alkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl;
• C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• or are substituted by halogen, C1-C10haloalkyl, NO2, CN, Ar2, (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7 and/or OSO2R7;
• or R1 is a group
• X1, X2 and X3 independently of each other are O or S;
• R′1 is phenylenedisulfonyl, naphthylenedisulfonyl,
• diphenylenedisulfonyl, or oxydiphenylenedisulfonyl, wherein these radicals are unsubstituted or substituted by C1-C12alkyl;
• or R′1 is C1-C12alkylenedisulfonyl;
• R2 is halogen or C1-C10haloalkyl;
• X is halogen;
• Ar1 is fluorenyl, which optionally is substituted by one or more C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl;
• C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• or is substituted by halogen, NO2, CN, Ar2, (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7, and/or OSO2R7, optionally the substituents (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, —NR4R5, SR6, SOR7, SO2R7, and/or OSO2R7 form 5-, 6- or 7-membered rings, via the radicals R3, R4, R5, R6 and/or R7, with further substituents on the fluorenyl ring or with one of the carbon atoms of the fluorenyl ring;
• or optionally the substituents C1-C18alkyl form alkylene bridges from one carbon atom of the fluorenyl ring to another carbon atom of said ring;
• said alkylene bridges optionally being condensed with further phenyl rings;
• or Ar1 is biphenylyl substituted by one or more C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl;
• C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• halogen, NO2, CN, Ar2, (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7, and/or OSO2R7, optionally the substituents (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7, and/or OSO2R7 form 5-, 6- or 7-membered rings, via the radicals R3, R4, R5, R6 and/or R7, with further substituents on the biphenylyl ring or with one of the carbon atoms of the biphenylyl ring;
• or optionally the substituents C1-C18alkyl form alkylene bridges from one carbon atom of the biphenylyl ring to another carbon atom of said ring;
• said alkylene bridges optionally being condensed with further phenyl rings;
• or Ar1 is naphthyl substituted by halogen, NO2, CN, (CO)R7, (CO)OR3, (CO)NR4R5, optionally the substituents (CO)R7, (CO)OR3 and/or (CO)NR4R5, form 5-, 6- or 7-membered rings, via the radicals R3, R4, R5, with further substituents on the naphthyl ring or with one of the carbon atoms of the naphthyl ring;
• or Ar1 is naphthyl substituted by C1-C18alkyl wherein the C1-C18alkyl substituent forms an alkylene bridge from one carbon atom of the naphthyl ring to another carbon atom of said ring;
• said alkylene bridges optionally being condensed with further phenyl rings;
• wherein all radicals Ar1 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;
• Ar′1 is heteroarylene, which is unsubstituted or substituted by one or more C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, NO2, CN, Ar2, (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7, and/or OSO2R7;
• wherein all radicals Ar′1 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;
• R3 is phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or is C2-C18alkyl which is interrupted by one or more O;
• or is C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO) or NR6(CO);
• or R3 is C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
• all of which optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R3 is hydrogen;
• R4 and R5 independently of each other are phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or are C2-C18alkyl which is interrupted by one or more O;
• or are C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• or are C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
• all of which optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R4 and R5 independently of each other are hydrogen;
• or R4 and R5, 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, NR6 or CO;
• R6 is phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or is C2-C18alkyl which is interrupted by one or more O;
• or is C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• or is C2-C18alkanoyl, benzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, naphthylsulfonyl, anthracylsulfonyl or phenanthrylsulfonyl;
• all of which optionally is substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R6 is hydrogen;
• R7 is phenyl, naphthyl, C3-C30cycloalkyl, C1-C18alkyl, C1-C10haloalkyl, C2-C12alkenyl, C4-C30cycloalkenyl;
• or is C2-C18alkyl which is interrupted by one or more O;
• or is C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• all of which optionally are substituted by one or more Ar2, OH, C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl, halogen, NO2, CN, C1-C18alkoxy, phenoxy, phenoxycarbonyl, phenylthio, phenylthiocarbonyl, NR4R5, C1-C12alkylthio, C2-C18alkoxycarbonyl, C2-C10haloalkanoyl, halobenzoyl, C1-C18alkylsulfonyl, phenylsulfonyl, (4-methylphenyl)sulfonyl, C1-C18alkylsulfonyloxy, phenylsulfonyloxy, (4-methylphenyl)sulfonyloxy, C2-C18alkanoyl, C2-C18alkanoyloxy, benzoyl and/or by benzoyloxy;
• or R7 is hydrogen;
• Ar2 is phenyl, naphthyl, anthracyl, phenanthryl, or heteroaryl, all of which are optionally substituted by one or more C1-C18alkyl, C1-C10haloalkyl, phenyl-C1-C3-alkyl, C3-C30cycloalkyl;
• C3-C30cycloalkyl which is interrupted by one or more O, S, NR6, O(CO), or NR6(CO);
• or are substituted by halogen, NO2, CN, phenyl, (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7, and/or OSO2R7, optionally the substituents (CO)R7, (CO)OR3, (CO)NR4R5, O(CO)R7, O(CO)OR3, O(CO)NR4R5, NR6(CO)R7, NR6(CO)OR3, OR3, NR4R5, SR6, SOR7, SO2R7, and/or OSO2R7 form 5-, 6- or 7-membered rings, via the radicals R3, R4, R5, R6 and/or R7, with further substituents on the phenyl, biphenylyl, naphthyl, anthracyl, phenanthryl, heteroaryl, or fluorenyl ring;
• or with one of the carbon atoms of the phenyl, biphenylyl, naphthyl, anthracyl, phenanthryl, heteroaryl, or fluorenyl ring;
• or optionally the substituents C1-C18alkyl form alkylene bridges from one carbon atom of the phenyl, biphenylyl, naphthyl, anthracyl, phenanthryl, heteroaryl, or fluorenyl ring to another carbon atom of said ring;
• said alkylene bridges optionally being condensed with further phenyl rings;
• R8, R9, R10 and R11 independently of one another are C1-C6alkyl which is unsubstituted or substituted by halogen;
• or R8, R9 and R10 are phenyl which is unsubstituted or substituted by C1-C4alkyl or halogen;
• or R10 and R11 together are 1,2-phenylene or C2-C6alkylene which is unsubstituted or substituted by C1-C4alkyl or halogen.