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OXIME ESTER PHOTOINITIATORS HAVING A SPECIAL AROYL CHROMOPHORE

20220121113 · 2022-04-21

    Inventors

    Cpc classification

    International classification

    Abstract

    Disclosed are α-keto oxime ester carbazole derivatives with a specific aroyl chromophore useful as a photo initiator, as well as photopolymerizable compositions comprising said photo initiator and ethylenically unsaturated compounds. The photopolymerizable compositions are useful, for example, in photoresist formulations for display applications, e.g. liquid crystal display (LCD), organic light emitting diode (OLED) and touch panel.

    Claims

    1. Compounds of the formula I ##STR00055## wherein R.sup.1 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sup.14, SR.sup.15, COOR.sup.14, CONR.sup.16R.sup.17, NR.sup.16R.sup.17, PO(OC.sub.kH.sub.2k+1).sub.2; or by ##STR00056## R.sup.1 is C.sub.2-C.sub.20alkyl which is interrupted by one or more O, CO, S, SO, SO.sub.2, C(O)O, OC(O), phenylene, naphthylene or NR.sup.18, wherein the interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more halogen, OR.sup.14, SR.sup.15, COOR.sup.14, CONR.sup.16R.sup.17, NR.sup.16R.sup.17; R.sup.1 is C.sub.2-C.sub.12alkenyl which is uninterrupted or is interrupted by one or more O, CO, S, SO, SO.sub.2, C(O)O, OC(O), phenylene, naphthylene or NR.sup.18, wherein the uninterrupted or interrupted C.sub.2-C.sub.12alkenyl are unsubstituted or are substituted by one or more halogen, OR.sup.14, SR.sup.15, COOR.sup.14, CONR.sup.16R.sup.17, NR.sup.16R.sup.17; R.sup.1 is C.sub.4-C.sub.8cycloalkenyl, C.sub.2-C.sub.12alkinyl, or C.sub.3-C.sub.10cycloalkyl which is uninterrupted or is interrupted by one or more O, CO, S, SO, SO.sub.2, C(O)O, OC(O), phenylene, naphthylene or NR.sup.18; or R.sup.1 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl each of which is unsubstituted or substituted by one or more phenyl, halogen, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, ##STR00057## COR.sup.3a, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, or by C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S, or NR.sup.18, or each of which is substituted by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14, CONR.sup.16R.sup.17, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aryloxycarbonyl, C.sub.3-C.sub.20heteroaryloxycarbonyl, OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17, or each of which is substituted by C.sub.3-C.sub.10cycloalkyl or by C.sub.3-C.sub.10cycloalkyl which is interrupted by one or more O, S, CO, or NR.sup.18; R.sup.2 is hydrogen, CN, COR.sup.3a, COOR.sup.14, CONR.sup.16R.sup.17, NO.sub.2, PO(OR.sup.3a).sub.2 or S(O).sub.mR.sup.3a; or R.sup.2 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, CN, COOR.sup.14, CONR.sup.16R.sup.17, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, ##STR00058## C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, PO(OR.sup.3a).sub.2 or S(O).sub.mR.sup.3a; or R.sup.2 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sup.16, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.14, CONR.sup.16R.sup.17, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17; or R.sup.2 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16 or COOR.sup.14; or R.sup.2 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, COOR.sup.14, COR.sup.3a CONR.sup.16R.sup.17, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, ##STR00059## C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14a, CONR.sup.16R.sup.17, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.16, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by one or more OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17; R.sup.2a is hydrogen, CN, COR.sup.3a, COOR.sup.14a, CONR.sup.16aR.sup.17a, NO.sub.2, PO(OR.sup.3a).sub.2 or S(O).sub.mR.sup.3a; or R.sup.2a is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, CN, COOR.sup.14a, CONR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2 or S(O).sub.mR.sup.3a; or R.sup.2a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sup.16a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.14a, CONR.sup.16aR.sup.17a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; or R.sup.2a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16a or COOR.sup.14a; or R.sup.2a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.14a, COR.sup.3a CONR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14a, CONR.sup.16aR.sup.17a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.16a, phenyl, naphthyl, benzoyl and naphthoyl, each of which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by one or more OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; R.sup.3 is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, CN, COOR.sup.14, CONR.sup.16R.sup.17, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O, S, CO or NR.sup.16, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17; or R.sup.3 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sup.16, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.14, CONR.sup.16R.sup.17, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17; or R.sup.3 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16 or COOR.sup.14; or R.sup.3 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, COOR.sup.14, COR.sup.3a or SO.sub.2—R.sup.3a; or R.sup.3 is C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more C.sub.1-C.sub.10alkyl, C.sub.1-C.sub.4haloalkyl, halogen, phenyl, C.sub.1-C.sub.20alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.3 is C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sup.16, CO, SO or SO.sub.2; or R.sup.3 is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, COOR.sup.14, (CO)R.sup.3a or SO.sub.2R.sup.3a; R.sup.3a is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, CN, COOR.sup.14a, CONR.sup.16aR.sup.17a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; or R.sup.3a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sup.16a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)—(C.sub.1-C.sub.8alkyl), COOR.sup.14a, CONR.sup.16aR.sup.17a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; or R.sup.3a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, each of which is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16a or COOR.sup.14a; or R.sup.3a is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.14a, (CO)—(C.sub.1-C.sub.8alkyl), benzoyl or SO.sub.2—(C.sub.1-C.sub.4haloalkyl); or R.sup.3a is C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more C.sub.1-C.sub.10alkyl, C.sub.1-C.sub.4haloalkyl, halogen, phenyl, C.sub.1-C.sub.20alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.3a is C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sup.16a, CO, SO or SO.sub.2; or R.sup.3a is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.14a, (CO)(C.sub.1-C.sub.8alkyl), SO.sub.2—(C.sub.1-C.sub.4haloalkyl), benzoyl, or ##STR00060## which benzoyl or ##STR00061## is unsubstituted or substituted by ##STR00062## R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 independently of each other are hydrogen, halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.20haloalkyl, C.sub.6-C.sub.20aryl, C.sub.1-C.sub.20alkoxy, C.sub.6-C.sub.20arylC.sub.1-C.sub.20alkyl, C.sub.3-C.sub.10cycloalkyl, amino, CN, NO.sub.2, O(CO)C.sub.1-C.sub.20alkyl, O(CO)C.sub.6-C.sub.10aryl, ##STR00063## COR.sup.13, COOR.sup.14, or R.sup.4 and R.sup.5 or R.sup.5 and R.sup.6, R.sup.7 and R.sup.8, R.sup.8 and R.sup.9, and R.sup.9 and R.sup.10 are ##STR00064## R.sup.11 and R.sup.12 independently of each other are hydrogen, halogen, C.sub.1-C.sub.30alkyl, C.sub.6-C.sub.20aryl, C.sub.1-C.sub.20alkoxy, C.sub.6-C.sub.20arylC.sub.1-C.sub.20alkyl, hydroxyC.sub.1-C.sub.20alky, hydroxyC.sub.1-C.sub.20alkoxyC.sub.1-C.sub.20alkyl, C.sub.3-C.sub.20cycloalkyl, C.sub.3-C.sub.20heterocycloalkyl, C.sub.3-C.sub.20cycloalkylC.sub.1-C.sub.20alkyl, C.sub.2-C.sub.30alkenyl, C.sub.2-C.sub.30alkynyl; or R.sup.11 and R.sup.12 are connected to each other to form a C.sub.2-C.sub.5alkylene ring, C.sub.2-C.sub.5alkenylene ring, or C.sub.2-C.sub.5alkynylene ring; R.sup.13 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl each of which is unsubstituted or substituted by one or more phenyl, halogen, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, or by C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S, or NR.sup.18, or each of which is substituted by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14, CONR.sup.16R.sup.17, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aryloxycarbonyl, C.sub.3-C.sub.20heteroaryloxycarbonyl, OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17; R.sup.14 is hydrogen, COR.sup.3a, COOR.sup.14a, CONR.sup.16R.sup.17, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, CN, COOR.sup.14a, CONR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2 or S(O).sub.mR.sup.3a; or R.sup.14 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sup.16a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.14a, CONR.sup.16aR.sup.17a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; or R.sup.14 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16a or COOR.sup.14a; or R.sup.14 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.14a, COR.sup.3a CONR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, ##STR00065## C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14a, CONR.sup.16aR.sup.17a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.16a; phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by one or more OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; or R.sup.14 together with one of the carbon atoms of R.sub.2 or M forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.16a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a, COR.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00066## or C.sub.3-C.sub.20cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a; R.sup.14a is hydrogen, (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.14a is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, 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)(C.sub.2-C.sub.4)alkenyl, O(CO)phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl and C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sup.14a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20het¬eroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.14a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); or R.sup.14a is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)C.sub.1-C.sub.8alkyl or (CO)N(C.sub.1-C.sub.8).sub.2, phenyl or benzoyl; or R.sup.14a is C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl, which C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; R.sup.15 is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a, CN, COOR.sup.14a, CONR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2 or S(O).sub.mR.sup.3a; or R.sup.15 is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sup.16a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.14a, CONR.sup.16aR.sup.17a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14a, SR.sup.15a, or NR.sup.16aR.sup.17a; or R.sup.15 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16a or COOR.sup.14a; or R.sup.15 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.14a, COR.sup.3a CONR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, ##STR00067## C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14a, CONR.sup.16aR.sup.17a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.16a, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; or R.sup.15 together with one of the carbon atoms of R.sub.2 or M forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.16a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COR.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00068## or C.sub.3-C.sub.20cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a; R.sup.15a is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, 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)(C.sub.2-C.sub.4)alkenyl, O(CO)phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl and C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sup.15a is C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl)2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.15a is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); or R.sup.15a is C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)C.sub.1-C.sub.8alkyl, (CO)N(C.sub.1-C.sub.8alkyl).sub.2, phenyl or benzoyl; or R.sup.15a is C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl, which C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; R.sup.16 and R.sup.17 independently of each other are hydrogen, S(O).sub.mR.sup.3a, O(CO)R.sup.3a, COR.sup.3a or CONR.sup.16aR.sup.17a; or R.sup.16 and R.sup.17 independently of each other are C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, C.sub.N COOR.sup.14a, COR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2 or S(O).sub.mR.sup.3a; or R.sup.16 and R.sup.17 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, NR.sup.16a, CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.14a, COR.sup.16aR.sup.17a, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14a, SR.sup.15a or NR.sup.16aR.sup.17a; or R.sup.16 and R.sup.17 independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16a or COOR.sup.14a; or R.sup.16 and R.sup.17 independently of each other are C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.14a, COR.sup.3a, CONR.sup.16aR.sup.17a, PO(OR.sup.3a).sub.2, S(O).sub.mR.sup.3a, ##STR00069## C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14a, CONR.sup.16aR.sup.17a, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, OR.sup.14a, SR.sup.15a, or NR.sup.16aR.sup.17a, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S or NR.sup.16a, phenyl, naphthyl, benzoyl and naphthoyl, which phenyl, naphthyl, benzoyl or naphthoyl is unsubstituted or substituted by OR.sup.14a, SR.sup.15a, or NR.sup.16aR.sup.17a; or R.sup.16 and R.sup.17 independently of each other are C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.16 and R.sup.17 independently of each other are C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, NR.sup.16a, CO, SO or SO.sub.2; or R.sup.16 and R.sup.17 independently of each other are C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.14a, COR.sup.3a or SO.sub.2R.sup.3a; or R.sup.16 together with one of the carbon atoms of R.sup.2 or M forms a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.16a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COR.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, ##STR00070## or C.sub.3-C.sub.20cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a; or R.sup.16 and R.sup.17 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.16a, and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COR.sup.3a, NO.sub.2, halogen, C.sub.1-C.sub.4-haloalkyl, CN, phenyl, ##STR00071## or C.sub.3-C.sub.20cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16a; R.sup.16a and R.sup.17a independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, S(O).sub.m(C.sub.1-C.sub.8alkyl), O(CO)(C.sub.1-C.sub.8alkyl), (CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl) or CON(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.16a and R.sup.17a independently of each other are C.sub.1-C.sub.20alkyl substituted by one or more halogen, OH, SH, CN, C.sub.3-C.sub.8alkenoxy, 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)(C.sub.2-C.sub.4)alkenyl, O(CO)phenyl, (CO)OH, (CO)O(C.sub.1-C.sub.8alkyl), C.sub.3-C.sub.8cycloalkyl, SO.sub.2(C.sub.1-C.sub.4haloalkyl), O(C.sub.1-C.sub.4haloalkyl), phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.3-C.sub.8cycloalkyl or C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sup.16a and R.sup.17a independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)(C.sub.1-C.sub.8alkyl), (CO)O(C.sub.1-C.sub.8alkyl), (CO)N(C.sub.1-C.sub.8alkyl).sub.2, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroaryl-carbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl or N(C.sub.1-C.sub.8alkyl).sub.2; or R.sup.16a and R.sup.17a independently of each other are C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl, which C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.8cycloalkyl is uninterrupted or interrupted by one or more O, S, CO, N(C.sub.1-C.sub.8alkyl) or COO(C.sub.1-C.sub.8alkyl); or R.sup.16a and R.sup.17a independently of each other are C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, CN, NO.sub.2, OH, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.8alkoxy, phenyl-C.sub.1-C.sub.3alkyloxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, diphenylamino, (CO)O(C.sub.1-C.sub.8alkyl), (CO)C.sub.1-C.sub.8alkyl, (CO)N(C.sub.1-C.sub.8alkyl).sub.2, phenyl or benzoyl; or R.sup.16a and R.sup.17a independently of each other are C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl, which C.sub.1-C.sub.20alkanoyl or C.sub.3-C.sub.12alkenoyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, OH, C.sub.1-C.sub.8alkoxy, phenoxy, C.sub.1-C.sub.8alkylsulfanyl, phenylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2 or diphenylamino; or R.sup.16a and R.sup.17a independently of each other are C.sub.1-C.sub.20alkoxy, which is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.8alkylphenyl or C.sub.1-C.sub.8alkoxyphenyl; or R.sup.16a and R.sup.17a independently of each other are C.sub.2-C.sub.20alkoxy, which is interrupted by one or more O, S, N(C.sub.1-C.sub.8alkyl), CO, SO or SO.sub.2; or R.sup.16a and R.sup.17a independently of each other are C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.8alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, CO(OC.sub.1-C.sub.8alkyl), (CO)(C.sub.1-C.sub.8alkyl) or SO.sub.2—(C.sub.1-C.sub.8alkyl); or R.sup.16a and R.sup.17a together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or N(C.sub.1-C.sub.8alkyl), and which 5- or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or more C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkylsulfanyl, N(C.sub.1-C.sub.8alkyl).sub.2, NO.sub.2, halogen, C.sub.1-C.sub.4haloalkyl, CN, phenyl or C.sub.3-C.sub.20cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or N(C.sub.1-C.sub.8alkyl); R.sup.18 is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.2-C.sub.20alkyl which is interrupted by one or more O, CO, C(O)O, or OC(CO), or is phenyl-C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or is interrupted by one or more O, CO, C.sub.1-C.sub.20alkyl, halogen, C.sub.1-C.sub.4haloalkyl, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17 or ##STR00072## or R.sup.18 is COR.sup.21; or R.sup.18 is phenyl or naphthyl both of which are unsubstituted or substituted by one or more C.sub.1-C.sub.20alkyl, halogen, C.sub.1-C.sub.4haloalkyl, OR.sup.14, SR.sup.15, or NR.sup.16R.sup.17, COR.sup.13; or R.sup.18 is C.sub.1-C.sub.6alkylene or C.sub.2-C.sub.6alkenylene linked to the phenyl or naphthyl ring of the carbazole moiety and forming a 5- or 6-membered saturated or unsaturated ring; R.sup.19 is COOR.sup.14, CONR.sup.16R.sup.17, COR.sup.14; or R.sup.19 has one of the meanings given for R.sup.16 and R.sup.17; R.sup.20 is COOR.sup.14, CONR.sup.16R.sup.17, or COR.sup.14; or R.sup.20 has one of the meanings given for R.sup.14; R.sup.23, R.sup.24, R.sup.25 and R.sup.26 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl, COR.sup.13, COOR.sup.14, OR.sup.14, or NO.sub.2; k is an integer 1 to 10; m is 1 or 2; n is integer 1 to 20; X.sup.1 is O, S, SO or SO.sub.2; X.sup.2 is O, CO, S or a direct bond; M is C.sub.1-C.sub.20alkylene which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, CN, COOR.sup.14, CONR.sup.16R.sup.17, C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O, S, CO or NR.sup.16, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, which C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14, SR.sup.15, or NR.sup.16R.sup.17; or M is C.sub.2-C.sub.20alkylene interrupted by one or more O, S, NR.sup.16, CO, SO or SO.sub.2, which C.sub.1-C.sub.20alkylene or C.sub.2-C.sub.20alkylene is unsubstituted or substituted by one or more substituents selected from the group consisting of C.sub.3-C.sub.8cycloalkyl, OH, SH, O(CO)R.sup.3a, COOR.sup.14, CONR.sup.16R.sup.17, C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl and C.sub.3-C.sub.20heteroarylcarbonyl, wherein C.sub.6-C.sub.20aryl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aroyl or C.sub.3-C.sub.20heteroarylcarbonyl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.8alkyl, OR.sup.14, SR.sup.15, or NR.sup.16R.sup.17; or M is C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene, which C.sub.2-C.sub.12alkenylene or C.sub.3-C.sub.20cycloalkylene is uninterrupted or interrupted by one or more O, S, CO, NR.sup.16 or COOR.sup.14; or M is C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene, which C.sub.6-C.sub.20arylene or C.sub.3-C.sub.20heteroarylene is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, C.sub.1-C.sub.4haloalkyl, phenyl, C.sub.1-C.sub.20alkylphenyl, C.sub.1-C.sub.8alkoxyphenyl, CN, NO.sub.2, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, COOR.sup.14, COR.sup.3a or SO.sub.2R.sup.3a; and Y is a direct bond, O, S or NR.sup.18.

    2. Compounds of the formula I according to claim 1, wherein the compounds are compounds of formula II: ##STR00073## R.sup.1 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sup.14, SR.sup.15, COOR.sup.14, NR.sup.16R.sup.17, CONR.sup.16R.sup.17, PO(OC.sub.kH.sub.2k+1).sub.2; or R.sup.1 is C.sub.2-C.sub.20alkyl which is interrupted by one or more O, CO, S, C(O)O, OC(O), phenylene, naphthylene or NR.sup.18, wherein the interrupted C.sub.1-C.sub.20alkyl is unsubstituted or substituted by one or more halogen, OR.sup.14, SR.sup.15, COOR.sup.14 NR.sup.16R.sup.17, CONR.sup.16R.sup.17; or R.sup.1 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl each of which is unsubstituted or substituted by one or more phenyl, halogen, C.sub.1-C.sub.4haloalkyl, CN, NO.sub.2, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, ##STR00074## or by C.sub.2-C.sub.20alkyl which is interrupted by one or more O, S, or NR.sup.18, or each of which is substituted by one or more C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, COOR.sup.14, CONR.sup.16R.sup.17, phenyl, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.20heteroaryl, C.sub.6-C.sub.20aryloxycarbonyl, C.sub.3-C.sub.20heteroaryloxycarbonyl, OR.sup.14, SR.sup.15 or NR.sup.16R.sup.17; R.sup.2 is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more substituents halogen, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, COOR.sup.14, ##STR00075## or C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O; or R.sup.2 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH, O(CO)R.sup.3a or COOR.sup.14; or R.sup.2 is C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl or C.sub.6-C.sub.20aryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, NO.sub.2, OR.sup.14, SR.sup.15, COOR.sup.14, COR.sup.3a or ##STR00076## or R.sup.2a is hydrogen, COR.sup.3a, COOR.sup.14a, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sup.14a, SR.sup.15a or C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O; R.sup.3 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sup.14, SR.sup.15, NR.sup.16R.sup.17, COOR.sup.14, C.sub.3-C.sub.8cycloalkyl or C.sub.3-C.sub.8cycloalkyl which is interrupted by one or more O; or R.sup.3 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more OH, O(CO)R.sup.3a or COOR.sup.14; or R.sup.3 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl; or R.sup.3 is C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, each of which is unsubstituted or substituted by one or more halogen or C.sub.1-C.sub.20alkyl; or R.sup.3 is C.sub.1-C.sub.20alkoxy, C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy; R.sup.3a is hydrogen, C.sub.1-C.sub.20alkyl, C.sub.2-C.sub.20alkyl interrupted by one or more O, C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl, C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl, which C.sub.6-C.sub.20aryl or C.sub.3-C.sub.20heteroaryl is unsubstituted or substituted by one or more halogen, C.sub.1-C.sub.20alkyl, OR.sup.14a, SR.sup.15a, NR.sup.16aR.sup.17a, COOR.sup.143, (CO)—(C.sub.1-C.sub.8alkyl) or benzoyl; or R.sup.3a is C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy, which C.sub.6-C.sub.20aryloxy or C.sub.3-C.sub.20heteroaryloxy is unsubstituted or substituted by benzoyl, or ##STR00077## which benzoyl or ##STR00078## is unsubstituted or substituted by ##STR00079## R.sup.4 to R.sup.12 are defined as in claim 1; R.sup.14 is hydrogen, COR.sup.3a, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl which is uninterrupted or interrupted by one or more O; or R.sup.14 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more C.sub.3-C.sub.8cycloalkyl, OH or COOR.sup.14a; or R.sup.14 is C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl or C.sub.6-C.sub.20aryl, which C.sub.6-C.sub.20aryl is unsubstituted or substituted by one or more halogen or C.sub.1-C.sub.20alkyl; or R.sup.14a is C.sub.1-C.sub.20alkyl; R.sup.15 is hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more OR.sup.14a, COOR.sup.14a, C.sub.3-C.sub.8cycloalkyl or C.sub.6-C.sub.20aryl; or R.sup.15 is C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by one or more OH or COOR.sup.14a; or R.sup.15 is C.sub.2-C.sub.12alkenyl or C.sub.3-C.sub.20cycloalkyl; or R.sup.15 is C.sub.6-C.sub.20aryl which is unsubstituted or substituted by one or more halogen or C.sub.2-C.sub.20alkyl which is uninterrupted or interrupted by one or more O; R.sup.15a is C.sub.1-C.sub.20alkyl; R.sup.16 and R.sup.17 independently of each other are hydrogen, C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by one or more halogen, OR.sup.14a, SR.sup.15a, COOR.sup.14a, C.sub.3-C.sub.8cycloalkyl or C.sub.6-C.sub.20aryl; or R.sup.16 and R.sup.17 independently of each other are C.sub.2-C.sub.20alkyl interrupted by one or more O, which interrupted C.sub.2-C.sub.20alkyl is unsubstituted or substituted by OH or SH; or R.sup.16 and R.sup.17 independently of each other are C.sub.2-C.sub.12alkenyl, C.sub.3-C.sub.20cycloalkyl or C.sub.6-C.sub.20aryl; or R.sup.16 and R.sup.17 together with the N-atom to which they are attached form a 5- or 6-membered saturated or unsaturated ring which is uninterrupted or interrupted by O, S or NR.sup.16a; R.sup.16a and R.sup.17a independently of each other are hydrogen or C.sub.1-C.sub.20alkyl; and X.sup.2 is CO or a direct bond.

    3. Compounds of the formula I according to claim 1 or 21, wherein the compounds are compounds of formula III: ##STR00080## wherein R.sup.1 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by NR.sup.16R.sup.17; or R.sup.1 is C.sub.2-C.sub.20alkyl which is interrupted by one or more C(O)O, OC(O) or phenylene, wherein the interrupted C.sub.1-C.sub.20alkyl is unsubstituted or substituted by NR.sup.16R.sup.17; or R.sup.1 is phenyl or thienyl each of which is unsubstituted or substituted by ##STR00081## R.sup.2 is C.sub.1-C.sub.20alkyl which is unsubstituted or substituted by halogen, SR.sup.15, NR.sup.16R.sup.17, COOR.sup.14 or C.sub.3-C.sub.8cycloalkyl; or R.sup.2 is C.sub.6-C.sub.20aryl which is unsubstituted or substituted by C.sub.1-C.sub.20alkyl; R.sup.2a is C.sub.1-C.sub.20alkyl or C.sub.6-C.sub.20aryl; R.sup.2a is C.sub.6-C.sub.20aryl which is unsubstituted or substituted by C.sub.1-C.sub.20alkyl; or R.sup.3 is C.sub.1-C.sub.20alkyl, C.sub.6-C.sub.20aryl or C.sub.1-C.sub.20alkoxy; R.sup.3a is C.sub.1-C.sub.20alkyl or C.sub.6-C.sub.20aryl; R.sup.8 is H, NO.sub.2, or COR.sup.13, wherein R.sup.11 and R.sup.12 independently of each other are hydrogen or C.sub.1-C.sub.20alkyl, R.sup.13 is phenyl, naphthyl or thienyl which is unsubstituted and substituted by phenyl, C.sub.1-C.sub.20alkyl, OR.sup.14, SR.sup.15, or NR.sup.16R.sup.17, wherein R.sup.14 is C.sub.1-C.sub.20alkyl or R.sup.14 together with one of the carbon atoms of R.sup.2 forms a 5- or 6-membered; R.sup.15 is C.sub.6-C.sub.20aryl; and R.sup.16 and R.sup.17 independently of each other are O(CO)R.sup.3a, COR.sup.3a or C.sub.1-C.sub.20alkyl.

    4. Compounds of the formula I according to claim 1, wherein the compounds are compounds of formula IV: ##STR00082## wherein R.sup.1 to R.sup.3, R.sup.11 and R.sup.12 are defined as in claim 1.

    5. A photopolymerizable composition comprising (a) at least one ethylenically unsaturated photopolymerizable compound and (b) as photoinitiator, at least one compound of the formula I as defined in claim 1.

    6. A photopolymerizable composition according to claim 5, wherein the component (a) is a resin obtained by the reaction of a saturated or unsaturated polybasic acid anhydride with a product of the reaction of an epoxy resin and an unsaturated monocarboxylic acid.

    7. A photopolymerizable composition according to claim 5, additionally to the photoinitiator (b) comprising at least one further photoinitiator (c), and/or other additives (d).

    8. A photopolymerizable composition according to claim 5 as further additive (d) comprising a pigment, or a mixture of pigments, or a dye, or a mixture of dyes, or a mixture of one or more pigments with one or more dyes.

    9. A photopolymerizable composition according to claim 8 as further additive (d) comprising a dispersant or a mixture of dispersants.

    10. A photopolymerizable composition according to claim 5, comprising 0.05 to 25% by weight of the photoinitiator (b), or the photoinitiators (b) and (c), based on the weight of the composition.

    11. A photopolymerizable composition according to claim 5 as further additive (d) comprising a photo sensitizer, in particular a compound selected from the group consisting of benzophenone, benzophenone derivatives, thioxanthone, thioxanthone derivatives, anthraquinone, anthraquinone derivatives, coumarin and coumarine derivatives.

    12. A photopolymerizable composition according to claim 5 additionally comprising a binder polymer (e), in particular a copolymer of methacrylate and methacrylic acid.

    13. A process for the preparation of a compound of the formula I according to claim 1 by reacting the corresponding oxime compound with an acyl halide of the formula I′ or an anhydride of the formula I″ ##STR00083## wherein Hal is a halogen, in particular CI, and R.sup.3 is as defined in claim 1, in the presence of a base or a mixture of bases.

    14. A process for the photopolymerization of compounds containing ethylenically unsaturated double bonds, which comprises irradiating a composition according to claim 5 with electromagnetic radiation in the range from 150 to 600 nm, or with electron beam or with X-rays.

    15. A process according to claim 14 for producing pigmented and nonpigmented paints and varnishes, powder coatings, printing inks, printing plates, adhesives, pressure sensitive adhesives, dental compositions, gel coats, photoresists for electronics, electroplating resists, etch resists, both liquid and dry films, solder resists, resists to manufacture color filters for a variety of display applications, resists to generate structures in the manufacturing processes of plasma-display panels, electroluminescence displays and LCD, spacers for LCD, for holographic data storage (HDS), as composition for encapsulating electrical and electronic components, for producing magnetic recording materials, micromechanical parts, waveguides, optical switches, plating masks, etch masks, colour proofing systems, glass fibre cable coatings, screen printing stencils, for producing three-dimensional objects by means of stereolithography, as image recording material, for holographic recordings, microelectronic circuits, decolorizing materials, decolorizing materials for image recording materials, for image recording materials using microcapsules, as a photoresist material for a UV and visible laser direct imaging system, as a photoresist material used for forming dielectric layers in a sequential build-up layer of a printed circuit board.

    16. Coated substrate which is coated on at least one surface with a composition according to claim 5.

    17. Process for the photographic production of relief images, in which a coated substrate according to claim 16 is subjected to imagewise exposure and then the unexposed portions are removed with a developer.

    18. A color filter prepared by providing red, green and blue picture elements and a black matrix, all comprising a photosensitive resin and a pigment on a transparent substrate and providing a transparent electrode either on the surface of the substrate or on the surface of the color filter layer, wherein said photosensitive resin comprises a polyfunctional acrylate monomer, an organic polymer binder and a photopolymerization initiator of formula I as defined in claim 1.

    19. Use of a compound of the formula (I) as defined in claim 1 for the photopolymerization of a composition comprising at least one ethylenically unsaturated photopolymerizable compound.

    20. Compounds of the formula (IA) ##STR00084## wherein R.sup.1, R.sup.2 and R.sup.4 to R.sup.12 are defined as in claim 1.

    Description

    SUBSTANCE EXAMPLES

    Example 1: Preparation of OE1

    [0435] OE1 is prepared as the following scheme:

    ##STR00049##

    [0436] Preparation of IM1-1

    [0437] To a solution of Fluorene (20.0 g) and Oxalyl Chloride (12.4 ml) in DCM (600 ml) was added aluminum chloride (16.8 g) at ice bath, the mixture was stirred for 1 h at room temperature. A solution of 9-ethylcarbazole in DCM was added to the reaction mixture at ice bath, the mixture was stirred for 1 h. Aluminum chloride (16.8 g) and 4-Methylvaleryl chloride (14.9 ml) was added to the reaction mixture at ice bath, the mixture was stirred for 1 h. The reaction mixture was quenched with ice water, extracted with DCM, washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product as a pale yellow solid (7.2 g).

    [0438] Preparation of IM1-2

    [0439] To a solution of IM1-1 (16.2 g) in DMSO (1300 ml) was added Potassium tert-butoxide (3.75 g) and 1-Iodobutane (3.8 ml), the mixture was stirred for 10 min at room temperature. Potassium tert-butoxide (3.75 g) and 1-Iodobutane (3.8 ml) were added to the reaction mixture, the mixture was stirred for 10 min at room temperature. The reaction mixture was quenched with ice water and the precipitate was collected by filtration. The solid was dissolved by ethyl acetate, washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to give the product as a pale yellow solid (20 g).

    [0440] Preparation of IM1-3

    [0441] To a solution of IM1-2 (19.1 g) and conc. HCl (2.7 ml) in DMF (120 ml) was added Amyl Nitrite (6.4 ml) at ice bath, the mixture was stirred for 15 h at room temperature. The reaction mixture was quenched with water, extracted with ethyl acetate, washed with brine, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to give the product as a pale yellow solid (7.8 g).

    [0442] Preparation of OE1

    [0443] To a solution of IM1-3 (4.9 g) and Triethylamine (1.1 ml) in DCM (100 ml) was added Acetyl Chloride (0.56 ml) at ice bath, the mixture was stirred for 15 min. The reaction mixture was quenched with water, extracted with DCM, and dried over anhydrous MgSO.sub.4. The solvent was removed under reduced pressure to give the product as a pale yellow solid (4.5 g).

    Example 2: Preparation of OE2

    [0444] OE2 is prepared as the following scheme:

    ##STR00050## ##STR00051##

    [0445] Preparation of IM2-1

    [0446] To 10.023 g of 9-ethylcarbazole and 8.052 g of aluminum chloride in dichloromethane (130 ml) was added 9.759 g of n-octanoyl chloride and stirred at rt under N.sub.2 flow conditions for 12 h. The reaction mixture was poured into ice-water and the precipitate was collected by filtration and dried in vacuo. The resulting solid was washed with mixture of hexane and dichloromethane, giving 8.628 g of IM2-1 as dark yellow sloid.

    [0447] Preparation of IM2-2

    [0448] To 2.078 g of IM2-1 and 1.377 g of 1-bromo-2-ethylhexane in DMA (10 ml) was added 0.475 g of potassium hydroxide, and stirred at room temperature for 12 h. Water is added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and dichloromethane (75:25 v/v) as eluent to give 2.397 g of IM2-2 as yellow oil.

    [0449] Preparation of IM2-4

    [0450] To 1.266 g of 9,9-dimethylfluorene-2-carboxylic acid was added 2.0 ml of thionyl chloride and stirred at 80° C. for 6 h. After cooling to room temperature, thionyl chloride was removed under reduced pressure, then, 1.363 g of IM2-3 was obtained as yellow resin. To 2.592 g of IM2-2 and 1.816 g of aluminum chloride in dichloromethane (30 ml) was added 1.363 g of IM2-3 and stirred at rt under N.sub.2 flow condition for 2 h. The reaction mixture was poured into ice-water and organic layer was separated. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and dichloromethane (90:10 to 30:70 v/v) as eluent to give 1.448 g of IM2-4 as pale yellow resin.

    [0451] Preparation of IM2-5

    [0452] To 1.448 g of IM2-4 was added mixture of dichloromethane (20 ml) and 4 mol/l of hydrochloric acid in 1,4-dioxane solution (1.0 ml) at room temperature. Then, 0.284 g of amyl nitrite was added and stirred for 2 h. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and dichloromethane (90:10 to 0:100 v/v) as eluent to give 0.716 g of IM2-5 as pale yellow resin.

    [0453] Preparation of OE2

    [0454] To 0.716 of IM2-5 and 0.126 of acetyl chloride in tetrahydrofuran (20 ml) was added 0.142 g of triethylamine at 0° C., then stirred at room temperature for 1 h. Water was added to the reaction mixture and organic layer was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under vacuum, and the crude was purified via column chromatography with hexane and dichloromethane (90:10 to 30:70 v/v) as eluent to give 0.496 g of OE2 as yellow resin.

    [0455] Compound List and Physical Data Thereof

    TABLE-US-00001 Oxime ester (OE) Structure .sup.1H NMR in CDCl.sub.3 OE1 [00052]embedded image 0.60-0.70 (m, 9H), 0.98 (d, 6H), 1.05-1.10 (m, 4H), 1.50-1.55 (m, 4H), 1.95-2.05 (m, 5H), 2.26 (s, 3H), 2.80 (d, 2H), 4.45 (q, 2H), 7.35-7.40 (m, 3H), 7.48 (d, 1H), 7.50 (d, 1H), 7.80-7.90 (m, 4H), 8.05 (dd, 1H), 8.34(dd, 1H), 8.72 (d, 1H), 8.91 (d, 1H) OE2 [00053]embedded image 0.84-0.89 (m, 6H), 0.95 (t, 3H), 1.26-1.56 (m, H), 2.03-2.11 (m, 1H), 2.25 (s, 3H), 2.84 (t, 2H), 4.26 (m, 2H), 7.93-7.43, (m, 2H), 7.47- 7.52 (m, 3H), 7.82-7.85 (m, 3H), 8.01 (s, 1H), 8.09 (dd, 1H), 8.29 (dd, 1H), 8.69 (d, 1H), 8.84 (d, 1H)

    APPLICATION EXAMPLES

    [0456] Sensitivity Test: A

    [0457] Preparation of Color Filter Resist (Blue)

    [0458] A blue pigment dispersion is prepared by mixing the following components and dispersing them by using a Paint conditioner (SKANDEX).

    [0459] Blue Dispersion

    TABLE-US-00002 5.6 parts by weight blue pigment (PB15:6, Blue E provided by Toyo Ink) 0.6 parts by weight violet pigment (PV23, Cromophtal Violet GA provided by BASF) 2.6 parts by weight dispersant (EFKA6745 provided by BASF) 0.4 parts by weight synergist (Solsperse S5000 provided by Lubrizol) 19.6 parts by weight  solvent (PGMEA)

    [0460] Color filter resists (blue) are prepared by further adding the following components to the above dispersion prepared.

    TABLE-US-00003 6.0 parts by weight alkaline developable binder, 37.8% solution (Ripoxy SPC-2000, provided by Shoko Highpolymer) 41.9 parts by weight  solvent (PGMEA) 5.0 parts by weight multifunctional acrylate (DPHA, provided by Sigma-Aldrich) 0.7 parts by weight Photoinitiator

    [0461] All operations are carried out under yellow light. The compositions are applied to a glass plate using a spincoater. The solvent is removed by heating at 80° C. for 10 minutes in a convection oven. The thickness of the dry film is approximately 1.2 μm. A stepwedge pattern mask with 9 linear steps and 9 logarithmic steps of different optical density (Edumund Optics, EIA GrayScale Pattern Slide) is placed on the resist directly. Exposure is carried out using a 250 W super high pressure mercury lamp (USHIO, USH-250BY) at a distance of 15 cm. A total exposure dose measured by an optical power meter (ORC UV Light Measure Model UV-M02 with UV-35 detector) on the glass filter is 500 mJ/cm.sup.2. After exposure, the exposed film is developed with an alkaline solution (5% aqueous solution of DL-A4, YOKOHAMA OILS & FATS) for 10 seconds after break time at 28° C. by using a spray type developer (AD-1200, MIKASA). Break time is the development time of the unexposed region. The necessary UV dose for full curing (i.e. the pattern is not dissolved with the alkaline solution) is calculated from the residual thickness of each step after development. The smaller the value of the dose, the more sensitive is the tested initiator. The results are listed in Table 1.

    [0462] Transparent Test: B

    [0463] All operations are carried out under yellow light. The compositions are applied to a glass plate using a spincoater. The film is measured transmittance from 350 nm to 780 nm after drying, exposure and baking using UV-VIS spectrometer (Shimazu, UV-2550). The solvent is removed by drying at 80° C. for 10 minutes in a convection oven. Exposure is carried out using a 250 W super high pressure mercury lamp (USHIO, USH-250BY) at a distance of 15 cm. A total exposure dose measured by an optical power meter (ORC UV Light Measure Model UV-M02 with UV-35 detector) on the glass filter is 50 mJ/cm.sup.2. After exposure, the exposed film is baked at 230° C. for 30 minutes in a forced convention oven. ΔE*ab at 0.094 of y is calculated from transmittance of the film. ΔE*ab means the difference of transmittance of the film after drying and of that after baking 230° C. for 30 minutes and smaller ΔE*ab value indicates less discoloration. The results are listed in Table 1.

    TABLE-US-00004 TABLE 1 Sensitivity and discoloration Example No. PI Sensitivity [mJ cm.sup.−2] ΔE*ab Example B1 OE1 50.6 2.62 Example B2 OE2 50.6 2.69 Comparative example 1 OE-R1 366 3.58 Comparative example 2 OE-R2 206.3 4.76

    [0464] The following photoinitiators were used in comparative examples 1 and 2:

    ##STR00054##

    [0465] As shown in table 1, the compounds of the present invention show significantly improved photosensitivity and at the same time reduced discoloration.