Photoresist compositions

A hydroxylamine-ester of the formula IC′

• wherein
• R1-R4 each represent C1-C6alkyl;
• and
• R5 and R6 each represent independently of one another hydrogen, C1-C6alkyl or C6-C10aryl;
• or R5 and R6 together represent oxygen,
• Ra is an acyl radical selected from —C(═O)—H, —C(═O)—C1-C32alkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkylene-C6-C10aryl, C(═O)—C2-C4alkylene-C(═O)—C1-C32alkyl, —C(═O)—C6-C10aryl, —C(═O)—O—C1-C32alkyl, —C(═O)—O-benzyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl and —C(═O)—N(C1-C32alkyl)2, wherein C1-C32alkyl and C6-C10aryl may be optionally interrupted by one or more O or C═O and/or substituted by one or more halogen, OR9, COOR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9, or NR9R10;
• wherein R9 and R10 independently of one another are hydrogen or unsubstituted or substituted C1-C32alkyl, C6-C10 aryl, C4-C10 heteroaryl, C7-C20 aralkyl or C4-C20 cycloalkyl, whereby the alkyl and cycloalkyl are uninterrupted or interrupted by O;
• G3 is a C2-C8 alkylene substituted by OR7
• R7 is C1-C32alkyl, C4-C20 cycloalkyl, —C(═O)—C4-C20 cycloalkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkenyl-C6-C10aryl, —C(═O)—(CH2)1-4—C(═O)—C1-C32alkyl, —C(═O)—C6-C10aryl, —C(═O)-benzyl, —C(═O)—O—C1-C32alkyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl —C(═O)—N(C1-C32alkyl)2 or —C(═S)—NH—C6-C10aryl, wherein C1-C32alkyl, C4-C20 cycloalkyl and C6-C10aryl may be optionally substituted by one or more halogen, OR8, COOR8, CONR8R9, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR8, OR8, or NR8R9 and/or C1-C32alkyl and C4-C20 cycloalkyl may be interrupted by one or more O or C═O;
• or —C(═O)—C1-C32alkyl, which is interrupted by one or more O or C═O and/or substituted by one or more halogen, OR8, COOR8, CONR8R9, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR8, OR8, or NR8R9;
• R8 is hydrogen, C1-C32alkyl, C4-C20 cycloalkyl, —C(═O)—C1-C32alkyl, —C(═O)—C4-C20 cycloalkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkenyl-C6-C10aryl, —C(═O)—C6-C10aryl, —C(═O)—O—C1-C32alkyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl —C(═O)—N(C1-C32alkyl)2 or —C(═S)—NH—C6-C10aryl, wherein C1-C32alkyl, C4-C20 cycloalkyl and C6-C10aryl may be optionally substituted by one or more halogen, OR9, COOR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9, or NR9R10 and/or C1-C32alkyl and C4-C20 cycloalkyl may be interrupted by one or more O or C═O;
• R9 and R10 independently of one another are hydrogen or unsubstituted or substituted C1-C32alkyl, C6-C10aryl, C4-C10heteroaryl, C7-C20 aralkyl or C4-C20 cycloalkyl, whereby the alkyl and cycloalkyl are uninterrupted or interrupted by O.

A radically polymerizable composition comprising:

• (a) at least one alkaline developable resin;
• (b) at least one acrylate monomer;
• (c) at least a photoinitiator;
• (d) at least one hydroxylamine ester compound of formula IA′
• or a hydroxylamine-ester of the formula IC′
• wherein
• in formula (IA′)
• R1-R4 each represent C1-C6alkyl;
• and
• R5 and R6 each represent independently of one another hydrogen, C1-C6alkyl or C6-C10aryl;
• or R5 and R6 together represent oxygen,
• Ra is an acyl radical selected from —C(═O)—H, —C(═O)—C1-C32alkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkylene-C6-C10aryl, C(═O)—C2-C4alkylene-C(═O)—C1-C32alkyl, —C(═O)—C6-C10aryl, —C(═O)—O—C1-C32alkyl, —C(═O)—O-benzyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl and —C(═O)—N(C1-C32alkyl)2 wherein C1-C32alkyl and C6-C10aryl may be optionally interrupted by one or more O or C═O and/or substituted by one or more halogen, OR9, COOR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9 or NR9R10;
• wherein R9 and R10 independently of one another are hydrogen or unsubstituted or substituted C1-C32alkyl, C6-C10aryl, C4-C10heteroaryl, C7-C20 aralkyl or C4-C20 cycloalkyl, whereby the alkyl and cycloalkyl are uninterrupted or interrupted by O;
• G C1-C32alkyl or —C(═O)—C1-C32alkyl, wherein C1-C32alkyl is interrupted by one or more C═O and/or substituted by one or more halogen, OR9, COOR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9, or NR9R10;
• or G is
• —C(═O)—C4-C20 cycloalkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkylene-C6-C10aryl, C(═O)—C2-C4alkylene-C(═O)C1-C32alkyl, or
• —C(═O)—C6-C10aryl, wherein C1-C32alkyl, C4-C20 cycloalkyl and C6-C10aryl may be optionally substituted by one or more halogen, OR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9 or NR9R10 and/or C1-C32alkyl and C4-C20 cycloalkyl may be interrupted by one or more O or C═O;
• or
• C4-C20 cycloalkyl, —C(═O)—O—C1-C32alkyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl —C(═O)—N(C1-C32alkyl)2 or —C(═S)—NH—C6-C10aryl, wherein C1-C32alkyl, C4-C20 cycloalkyl and C6-C10aryl may be optionally substituted by one or more halogen, OR9, COOR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9 or NR9R10 and/or C1-C32alkyl and C4-C20cycloalkyl may be interrupted by one or more O or C═O;
• R9 and R10 independently of one another are hydrogen or unsubstituted or substituted C1-C32alkyl, C6-C10aryl, C4-C10heteroaryl, C7-C20 aralkyl or C4-C20 cycloalkyl, whereby the alkyl and cycloalkyl are uninterrupted or interrupted by 0,
• in formula (IC′)
• R1-R4 each represent C1-C6alkyl;
• and
• R5 and R6 each represent independently of one another hydrogen, C1-C6alkyl or C6-C10aryl;
• or R5 and R6 together represent oxygen,
• Ra is an acyl radical selected from —C(═O)—H, —C(═O)—C1-C32alkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkylene-C6-C10aryl, C(═O)—C2-C4alkylene-C(═O)—C1-C32alkyl, —C(═O)—C6-C10aryl, —C(═O)—O—C1-C32alkyl, —C(═O)—O-benzyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl and —C(═O)—N(C1-C32alkyl)2, wherein C1-C32alkyl and C6-C10aryl may be optionally interrupted by one or more O or C═O and/or substituted by one or more halogen, OR9, COOR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9, or NR9R10;
• wherein R9 and R10 independently of one another are hydrogen or unsubstituted or substituted C1-C32alkyl, C6-C10aryl, C4-C10heteroaryl, C7-C20 aralkyl or C4-C20 cycloalkyl, whereby the alkyl and cycloalkyl are uninterrupted or interrupted by O;
• G3 is a C2-C8 alkylene substituted by OR7
• R7 is C1-C32alkyl, C4-C20 cycloalkyl, —C(═O)—C4-C20 cycloalkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkenyl-C6-C10aryl, —C(═O)—(CH2)1-4—C(═O)—C1-C32alkyl, —C(═O)—C6-C10aryl, —C(═O)-benzyl, —C(═O)—O—C1-C32alkyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl —C(═O)—N(C1-C32alkyl)2 or —C(═S)—NH—C6-C10aryl, wherein C1-C32alkyl, C4-C20 cycloalkyl and C6-C10aryl may be optionally substituted by one or more halogen, OR8, COOR8, CONR8R9, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR8, OR8, or NR8R9 and/or C1-C32alkyl and C4-C20 cycloalkyl may be interrupted by one or more O or C═O;
• or —C(═O)—C1-C32alkyl, which is interrupted by one or more O or C═O and/or substituted by one or more halogen, OR8, COOR8, CONR8R9, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR8, OR8, or NR8R9;
• R8 is hydrogen, C1-C32alkyl, C4-C20 cycloalkyl, —C(═O)—C1-C32alkyl, —C(═O)—C4-C20 cycloalkyl, —C(═O)—C2-C32alkenyl, —C(═O)—C2-C4alkenyl-C6-C10aryl, —C(═O)—C6-C10aryl, —C(═O)—O—C1-C32alkyl, —C(═O)—O—C6-C10aryl, —C(═O)—NH—C1-C32alkyl, —C(═O)—NH—C6-C10aryl —C(═O)—N(C1-C32alkyl)2 or —C(═S)—NH—C6-C10aryl, wherein C1-C32alkyl, C4-C20 cycloalkyl and C6-C10aryl may be optionally substituted by one or more halogen, OR9, COOR9, CONR9R10, phenyl or phenyl substituted by halogen, C1-C32alkyl, C1-C4haloalkyl, SR9, OR9, or NR9R10 and/or C1-C32alkyl and C4-C20 cycloalkyl may be interrupted by one or more O or C═O;
• R9 and R10 independently of one another are hydrogen or unsubstituted or substituted C1-C32alkyl, C6-C10aryl, C4-C10heteroaryl, C7-C20 aralkyl or C4-C20 cycloalkyl, whereby the alkyl and cycloalkyl are uninterrupted or interrupted by O.