Photosensitive resin composition, color filter, and liquid crystal display element thereof

A photosensitive resin composition, comprising:

• an alkali-soluble resin (A);
• a compound (B) having an ethylenically unsaturated group;
• a photoinitiator (C);
• a solvent (D);
• a black pigment (E);
• and
• a compound (H) represented by formula (10);
• wherein in formula (10), Z1, Z2, and Z3 each independently represent a trialkoxysilane group bonded by an alkylene group or an arylene group,
• wherein the compound (B) having an ethylenically unsaturated group contains a compound (B-1) having an acidic group and at least three ethylenically unsaturated groups;
• the photoinitiator (C) comprises a photoinitiator (C-1) represented by formula (1);
• wherein R1, R2, R3, R4, R5, R6, R7, and R8 are each independently hydrogen, a C1 to C20 alkyl group, COR16, OR17, halogen, NO2, a group represented by formula (2), or a group represented by formula (3),
• or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are each independently C2 to C10 alkenyl groups substituted by a group represented by formula (4)
• or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are each independently —(CH2)p—Y—(CH2)q— at the same time;
• or R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 are each independently a group represented by formula (5) at the same time;
• provided that at least one pair in R1 and R2, R2 and R3, R3 and R4, R5 and R6, R6 and R7, or R7 and R8 is a group represented by formula (5),
• R9, R10, R11, and R12 are each independently hydrogen or a C1 to C20 alkyl group, and the C1 to C20 alkyl group is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, a phenyl group, CN, OH, SH, a C1 to C4 alkoxy group, —(CO)OH, or —(CO)O—(C1 to C4 alkyl);
• or R9, R10, R11, and R12 are each independently an unsubstituted phenyl group or a phenyl group substituted by one or a plurality of the following groups:
• a C1 to C6 alkyl group, halogen, CN, OR17, SR18, or NR19R20;
• or R9, R10, R11, and R12 are each independently halogen, CN, OR17, SR18, SOR18, SO2R18, or NR19R20, wherein the substituent OR17, SR18, or NR19R20 forms a 5-membered or 6-membered ring with one carbon atom in a naphthyl ring via groups R17, R18, R19, and/or R20 as needed;
• or R9, R10, R11, and R12 are each independently COR16, NO2, or a group represented by formula (2),
• Y represents O, S, NR26, or a direct bond;
• p represents an integer of 0, 1, 2, or 3;
• q represents an integer of 1, 2, or 3;
• X represents CO or a direct bond;
• R13 represents a C1 to C20 alkyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, R17, COOR17, OR17, SR18, CONR19R20, NR19R20, PO(OCkH2k+1)2, or a group represented by formula (6);
• or R13 represents a C2 to C20 alkyl group interrupted with one or a plurality of O, S, SO, SO2, NR26, or CO, or a C2 to C12 alkenyl group interrupted or uninterrupted with one or a plurality of O, CO, or NR26, wherein the interrupted C2 to C20 alkyl group and the uninterrupted or is interrupted C2 to C12 alkenyl group is unsubstituted or substituted by one or a plurality of halogens;
• or R13 represents a C4 to C8 cycloalkenyl group, a C2 to C12 alkynyl group, or a C3 to C10 cycloalkyl group uninterrupted or is interrupted with one or a plurality of O, S, CO, or NR26;
• or R13 represents a phenyl group or a naphthyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• OR17, SR18, NR19R20, COR16, CN, NO2, halogen, a C1 to C20 alkyl group, a C1 to C4 haloalkyl group, a C2 to C20 alkyl group, which is interrupted with one or a plurality of O, S, CO, or NR26, or a group represented by formula (7),
• or the phenyl group or naphthyl group is substituted by a C3 to C10 cycloalkyl group or a C3 to C10 cycloalkyl group interrupted with one or a plurality of O, S, CO, or NR26;
• k represents an integer of 1 to 10;
• R14 represents hydrogen, a C3 to C8 cycloalkyl group, a C2 to C5 alkenyl group, a C1 to C20 alkoxy group, or a C1 to C20 alkyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, a phenyl group, a C1 to C20 alkylphenyl group, or CN;
• or R14 represents a phenyl group or a naphthyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C6 alkyl group, a C1 to C4 haloalkyl group, halogen, CN, OR17, SR18, and/or NR19R20;
• or R14 represents a C3 to C20 heteroaryl group, a C1 to C8 alkoxy group, a benzyloxy group, or a phenoxy group, and the benzyloxy group and the phenoxy group are unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C6 alkyl group, a C1 to C4 haloalkyl group, and/or halogen;
• R15 represents a C6 to C20 aryl group or a C3 to C20 heteroaryl group that is unsubstituted or substituted by one or a plurality of the following groups:
• a phenyl group, halogen, a C1 to C4 haloalkyl group, CN, NO2, OR17, SR18, NR19R20, PO(OCkH2k+1)2, SO—C1 to C10 alkyl, SO2—C1 to C10 alkyl, or a C2 to C20 alkyl group interrupted with one or a plurality of O, S, or NR26;
• or the C6 to C20 aryl group or C3 to C20 heteroaryl group is substituted by a C1 to C20 alkyl group, and the C1 to C20 alkyl group is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, COOR17, CONR19R20, a phenyl group, a C3 to C8 cycloalkyl group, a C3 to C20 heteroaryl group, a C6 to C20 aryloxycarbonyl group, a C3 to C20 heteroaryloxycarbonyl group, OR17, SR18, or NR19R20;
• or R15 represents hydrogen, a C2 to C12 alkenyl group, a C3 to C8 cycloalkyl group uninterrupted or is interrupted with one or a plurality of O, CO, or NR26;
• or R15 represents a C1 to C20 alkyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, OR17, SR18, a C3 to C8 cycloalkyl group, a C3 to C20 heteroaryl group, a C6 to C20 aryloxycarbonyl group, a C3 to C20 heteroaryloxycarbonyl group, NR19R20, COOR17, CONR19R20, PO(OCkH2k+1)2, a phenyl group, a group represented by formula (6), or a group represented by formula (8),
• or the C1 to C20 alkyl group is substituted by a phenyl group, and the phenyl group is substituted by halogen, a C1 to C20 alkyl group, a C1 to C4 haloalkyl group, OR17, SR18, or NR19R20;
• or R15 represents a C2 to C20 alkyl group interrupted with one or a plurality of O, S, or SO2, and the interrupted C2 to C20 alkyl group is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, OR17, COOR17, CONR19R20, a phenyl group, or a phenyl group substituted by OR17, SR18, or NR19R20;
• or R15 represents a C2 to C20 alkanoyl group or a benzoyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C6 alkyl group, halogen, a phenyl group, OR17, SR18, or NR19R20;
• or R15 represents a naphthoyl group that is unsubstituted or substituted by one or a plurality of OR17, or a C3 to C14 heteroarylcarbonyl group;
• or R15 represents a C2 to C12 alkoxycarbonyl group that is uninterrupted or is interrupted with one or a plurality of O and the interrupted or uninterrupted C2 to C12 alkoxycarbonyl group is unsubstituted or substituted by one or a plurality of hydroxyl groups;
• or R15 represents a phenoxycarbonyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C6 alkyl group, halogen, a C1 to C4 haloalkyl group, a phenyl group, OR17, SR18, or NR19R20;
• or R15 represents CN, CONR19R20, NO2, a C1 to C4 haloalkyl group, S(O)m— C1 to C6 alkyl, S(O)m-phenyl that is unsubstituted or substituted by a C1 to C12 alkyl group or SO2—C1 to C6 alkyl;
• or R15 represents SO2O-phenyl that is unsubstituted or substituted by a C1 to C12 alkyl group;
• or R15 represents a diphenylphosphinoyl group or di-(C1 to C4 alkoxy)-phosphinoyl;
• m represents 1 or 2;
• R′14 is defined the same as one of the R14's;
• R′15 is defined the same as one of the R15's;
• X1 represents O, S, SO, or SO2;
• X2 represents O, CO, S, or a direct bond;
• R16 represents a C6 to C20 aryl group or a C3 to C20 heteroaryl group that is unsubstituted or substituted by one or a plurality of the following groups:
• a phenyl group, halogen, a C1 to C4 haloalkyl group, CN, NO2, OR17, SR18, NR19R20, or a C1 to C20 alkyl group interrupted with one or a plurality of O, S, or NR26;
• or the C6 to C20 aryl group or C3 to C20 heteroaryl group is substituted by one or a plurality of a C1 to C20 alkyl group, and the C1 to C20 alkyl group is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, COOR17, CONR19R20, a phenyl group, a C3 to C8 cycloalkyl group, a C3 to C20 heteroaryl group, a C6 to C20 aryloxycarbonyl group, a C3 to C20 heteroaryloxycarbonyl group, OR17, SR18, or NR19R20;
• or R16 represents hydrogen or a C1 to C20 alkyl group, and the C1 to C20 alkyl group is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, a phenyl group, OH, SH, CN, a C3 to C6 alkenyloxy group, OCH2CH2CN, OCH2CH2(CO)O(C1 to C4 alkyl), O(CO)—(C1 to C4 alkyl), O(CO)-phenyl, (CO)OH, or (CO)O(C1 to C4 alkyl);
• or R16 represents a C2 to C12 alkyl group interrupted with one or a plurality of O, S, or NR26;
• or R16 represents (CH2CH2O)n+1H, (CH2CH2O)n(CO)—(C1 to C8 alkyl), a C2 to C12 alkenyl group, or a C3 to C8 cycloalkyl group;
• or R16 represents a phenyl group substituted by SR18, wherein the group R18 represents a direct bond bonded to the phenyl group or naphthyl ring of a carbazole portion to which the COR16, group is attached;
• n represents 1 to 20;
• R 17 represents hydrogen, phenyl-C1 to C3 alkyl, or a C1 to C20 alkyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, OH, SH, CN, a C3 to C6 alkenyloxy group, OCH2CH2CN, OCH2CH2(CO)O(C1 to C4 alkyl), O(CO)—(C1 to C4 alkyl), O(CO)—(C2 to C4)alkenyl, O(CO)-phenyl, (CO)OH, (CO)O(C1 to C4 alkyl), a C3 to C20 cycloalkyl group, SO2—(C1 to C4 haloalkyl), O(C1 to C4 haloalkyl), or a C3 to C20 cycloalkyl group interrupted with one or a plurality of O;
• or R17 represents a C2 to C20 alkyl group interrupted with one or a plurality of O, S, or NR26;
• or R17 represents (CH2CH2O)n+1H, (CH2CH2O)n(CO)—(C1 to C8 alkyl), a C1 to C8 alkanoyl group, a C2 to C12 alkenyl group, a C3 to C6 alkenoyl group, or a C3 to C20 cycloalkyl group uninterrupted or is interrupted with one or a plurality of O, S, CO, or NR26;
• or R17 represents C1 to C8 alkyl-C3 to C10 cycloalkyl that is uninterrupted or is interrupted with one or a plurality of O;
• or R17 represents a benzoyl group that is unsubstituted or substituted by one or a plurality of a C1 to C6 alkyl group, halogen, OH, or a C1 to C3 alkoxy group;
• or R17 represents a phenyl group, a naphthyl group, or a C3 to C20 heteroaryl group that is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, OH, a C1 to C12 alkyl group, a C1 to C12 alkoxy group, CN, NO2, phenyl-C1 to C3 alkoxy, a phenoxy group, a C1 to C12 alkylthio group, a phenylthio group, N(C1 to C12 alkyl)2, diphenyl-amine, or a group represented by formula (7);
• or R17 forms a direct bond bonded to one of the carbon atoms of the phenyl group or naphthyl ring having a group represented by formula (2) or a group represented by formula (7),
• R18 represents hydrogen, a C2 to Cl2 alkenyl group, a C3 to C20 cycloalkyl group, or phenyl-C1 to C3 alkyl, wherein the C2 to C12 alkenyl group, C3 to C20 cycloalkyl group, or phenyl-C1 to C3 alkyl is uninterrupted or is interrupted with one or a plurality of O, S, CO, NR26, or COOR17;
• or R18 is a C1 to C20 alkyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• OH, SH, CN, C3 to C6 alkenyloxy, OCH2CH2CN, OCH2CH2(CO)O(C1 to C4 alkyl), O(CO)—(C2 to C4)alkenyl, O(CO)—(C1 to C4 alkyl), O(CO)-phenyl, or (CO)OR17;
• or R18 represents a C2 to C20 alkyl group interrupted with one or a plurality of O, S, CO, NR26, or COOR17;
• or R18 represents (CH2CH2O)nH, (CH2CH2O)n(CO)—(C1 to C8 alkyl), a C2 to C8 alkanoyl group, or a C3 to C6 alkenoyl group;
• or R18 represents a benzoyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C6 alkyl group, halogen, OH, a C1 to C4 alkoxy group, or a C1 to C4 alkylthio group;
• or R18 represents a phenyl group, a naphthyl group, or a C3 to C20 heteroaryl group that is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, a C1 to C12 alkyl group, a C1 to C4 haloalkyl group, a C1 to C 12 alkoxy group, CN, NO2, phenyl-C1 to C3 alkoxy, a phenoxy group, a C1 to C12 alkylthio group, a phenylthio group, N(C1 to C12 alkyl)2, a diphenylamino group, (CO)O(C1 to C8 alkyl), (CO)—C1 to C8 alkyl, (CO)N(C1 to C8 alkyl)2, or a group represented by formula (7)
• R19 and R20 are each independently hydrogen, a C1 to C20 alkyl group, a C2 to C4 hydroxyalkyl group, a C2 to C10 alkoxyalkyl group, a C2 to C5 alkenyl group, a C3 to C20 cycloalkyl group, phenyl-C1 to C3 alkyl, a C1 to C8 alkanoyl group, a C1 to C8 alkanoyloxy group, a C3 to C12 alkenoyl group, SO2—(C1 to C4 haloalkyl), or a benzoyl group;
• or R19 and R20 each independently represent a phenyl group, a naphthyl group, or a C3 to C20 heteroaryl group that is unsubstituted or substituted by one or a plurality of the following groups:
• halogen, a C1 to C4 haloalkyl group, a C1 to C20 alkoxy group, a C1 to C12 alkyl group, a benzoyl group, or a C1 to C12 alkoxy group;
• or R19 and R20 form a 5-membered or 6-membered saturated or unsaturated ring that is uninterrupted or is interrupted with O, S, or NR17 with a nitrogen atom attached thereto, and the 5-membered or 6-membered saturated or unsaturated ring is unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C20 alkyl group, a C1 to C20 alkoxy group, ═O, OR17, SR18, NR21R22, (CO)R23, NO2, halogen, C1 to C4-haloalkyl, CN, a phenyl group, a C3 to C20 cycloalkyl group that is uninterrupted or is interrupted with one or a plurality of O, S, CO, or NR17, or a group represented by formula (7)
• or R19 and R20 form a heteroaromatic ring system with a nitrogen atom attached thereto, and the ring system is unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C20 alkyl group, a C1 to C4 haloalkyl group, a C1 to C20 alkoxy group, ═O, OR17, SR18, NR21R22, (CO)R23, halogen, NO2, CN, a phenyl group, or a C3 to C20 cycloalkyl group that is uninterrupted or is interrupted with one or a plurality of O, S, CO, or NR17, or a group represented by formula (7)
• R21 and R22 are each independently hydrogen, a C1 to C20 alkyl group, a C1 to C4 haloalkyl group, a C3 to C10 cycloalkyl group, or a phenyl group;
• or R21 and R22 form a 5-membered or 6-membered saturated or unsaturated ring that is uninterrupted or is interrupted with O, S, or NR26 with a nitrogen atom attached thereto, and the 5-membered or 6-membered saturated or unsaturated ring is not fused or the 5-membered or 6-membered saturated or unsaturated ring is fused with a benzene ring;
• R23 represents hydrogen, OH, a C1 to C20 alkyl group, a C1 to C4 haloalkyl group, a C2 to C20 alkyl group interrupted with one or a plurality of O, CO, or NR26, a C3 to C20 cycloalkyl group that is uninterrupted or is interrupted with O, S, CO, or NR26, or R23 represents a phenyl group, a naphthyl group, phenyl-C1 to C4 alkyl, OR17, SR18, or NR21R22;
• R24 represents (CO)OR17, CONR19R20, or (CO)R17;
• or R24 is defined the same as one of the R19's and R20's;
• R25 represents COOR17, CONR19R20, or (CO)R17;
• or R25 is defined the same as one of the R17's;
• R26 represents hydrogen, a C1 to C20 alkyl group, a C1 to C4 haloalkyl group, or a C2 to C20 alkyl group interrupted with one or a plurality of O or CO;
• or phenyl-C1 to C4 alkyl or a C3 to C8 cycloalkyl group that is uninterrupted or is interrupted with one or a plurality of O or CO;
• or (CO)R19;
• or a phenyl group that is unsubstituted or substituted by one or a plurality of the following groups:
• a C1 to C20 alkyl group, halogen, a C1 to C4 haloalkyl group, OR17, SR18, NR19R20, or a group represented by formula (7)
• provided that, at least one group represented by formula (2) or formula (7) is present in the molecule