Negative dye-containing curable composition, color filter and method of producing the same
View Patent ↗The present invention provides a negative dye-containing curable composition comprising at least (A) an alkali-soluble binder, (B) an organic solvent-soluble dye, (C) a photopolymerization initiator, (D) a radical-polymerizable monomer and (E) an organic solvent, wherein the organic solvent-soluble dye (B) comprises at least one kind of azomethine-type dye represented by the following formula (I) and at least one kind of tetraazaporphyrin-type dye represented by the following formula (A), and the photopolymerization initiator (C) is an oxime-type compound, wherein R 1 represents a hydrogen atom or a substituent group; R 2 to R 5 each represent a hydrogen atom or a substituent group, R 6 to R 7 each represent an alkyl group, alkenyl group, aryl group or heterocyclic group, Za and Zb each represent —N═ or —C(R 8 )═; R 8 represents a hydrogen atom, alkyl group, aryl group or heterocyclic group; M 1 represents a metal, and Z 1 to Z 4 each represent an atomic group forming a 6-membered ring composed of atoms selected from carbon and nitrogen.
1. A negative dye-containing curable composition comprising at least (A) an alkali-soluble binder, (B) an organic solvent-soluble dye, (C) a photopolymerization initiator, (D) a radical-polymerizable monomer and (E) an organic solvent,
wherein the organic solvent soluble dye (B) comprises at least one kind of azomethine-type dye represented by the following formula (I) and at least one kind of tetraazaporphyrin-type dye represented by the following formula (A), and the photopolymerization initiator (C) is an oxime-type compound,
wherein R 1 represents a hydrogen atom or a substituent group; R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom or a substituent group; R 6 and R 7 each independently represent an alkyl group, alkenyl group, aryl group or heterocyclic group; Za and Zb each independently represent —N═ or —C(R 8 )═; R 8 represents a hydrogen atom, alkyl group, aryl group or heterocyclic group; and R 2 and R 3 , R 3 and R 6 , R 4 and R 5 , R 5 and R 7 , or R 6 and R 7 each independently may be bonded to each other to form a 5- to 7-membered ring,
wherein M 1 represents a metal, and Z 1 , Z 2 , Z 3 and Z 4 each independently represent an atomic group forming a 6-membered ring composed of atoms selected from a carbon atom and a nitrogen atom.
2. The negative dye-containing curable composition according to claim 1 , wherein the azomethine-type dye represented by the formula (I) is an azomethine-type dye represented by the following formula (II):
wherein R 1 represents a hydrogen atom or a substituent group; R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent group; R 6 represents an alkyl group, alkenyl group, aryl group or heterocyclic group; R 9 , R 10 , R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or a substituent group; Za and Zb each independently represent —N═ or —C(R 8 )═; R 8 represents a hydrogen atom, alkyl group, aryl group or heterocyclic group; and R 2 and R 3 , R 3 and R 6 , R 6 and R 9 , or R 4 and R 14 each independently may be bonded to each other to form a 5- to 7-membered ring.
3. The negative dye-containing curable composition according to claim 1 , wherein the azomethine-type represented by the formula (I) is an azomethine-type dye represented by the following formula (III):
wherein R 1 represents a hydrogen atom or a substituent group; R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent group; R 6 represents an alkyl group, alkenyl group, aryl group or heterocyclic group; R 9 , R 10 , R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or a substituent group; R 15 represents a hydrogen atom, alkyl group, aryl group or heterocyclic group; and R 2 and R 3 , R 3 and R 6 , R 6 and R 9 , or R 4 and R 14 each independently may be bonded to each other to form a 5- to 7-membered ring.
4. The negative dye-containing curable composition according to claim 1 , wherein the tetraazaporphyrin-type dye represented by the formula (A) is a phthalocyanine dye represented by the following formula (B):
wherein M 1 represents a metal; and R 101 to R 116 each independently represent a hydrogen atom or a substituent group.
5. The negative dye-containing curable composition according to claim 1 , wherein a ratio of a mass of the azomethine-type dye represented by the formula (I) to a mass of the tetraazaporphyrin-type dye represented by the formula (A) (azomethine-type dye/tetraazaporphyrin-type dye) is in the range of from 1/9 to 9/1.
6. The negative dye-containing curable composition according to claim 1 , wherein the total concentration of (B) the organic solvent-soluble dye is in the range of from 0.5% by mass to 80% by mass based on the total solid components.
7. The negative dye-containing curable composition according to claim 1 , wherein (A) the alkali-soluble binder is a resin having an unsaturated double bond in a side chain thereof.
8. The negative dye-containing curable composition according to claim 1 , wherein (E) the organic solvent comprises a cyclic ketone solvent.
9. The negative dye-containing curable composition according to claim 1 , wherein the oxime-type compound is selected from
2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octane dione and
1-(O-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone.
10. A color filter, produced by using a negative dye-containing curable composition comprising at least (A) an alkali-soluble binder, (B) an organic solvent-soluble dye, (C) a photopolymerization initiator, (D) a radical-polymerizable monomer and (E) an organic solvent,
wherein the organic solvent-soluble dye (B) comprises at least one kind of azomethine-type dye represented by the following formula (I) and at least one kind of tetraazaporphyrin-type dye represented by the following formula (A), and the photopolymerization initiator (C) is an oxime-type compound,
wherein R 1 represents a hydrogen atom or a substituent group; R 2 , R 3 , R 4 and R 5 each independently represent a hydrogen atom or a substituent group; R 6 and R 7 each independently represent an alkyl group, alkenyl group, aryl group or heterocyclic group; Za and Zb each independently represent —N═ or —C(R 8 )═; R 8 represents a hydrogen atom, alkyl group, aryl group or heterocyclic group; and R 2 and R 3 , R 3 and R 6 , R 4 and R 5 , R 5 and R 7 , or R 6 and R 7 each independently may be bonded to each other to form a 5- to 7-membered ring,
wherein M 1 represents a metal, and Z 1 , Z 2 , Z 3 and Z 4 each independently represent an atomic group forming a 6-membered ring composed of atoms selected from a carbon atom and a nitrogen atom.
11. The color filter according to claim 10 , wherein the azomethine-type dye represented by the formula (I) is an azomethine-type dye represented by the following formula (II):
wherein R 1 represents a hydrogen atom or a substituent group; R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent group; R 6 represents an alkyl group, alkenyl group, aryl group or heterocyclic group; R 9 , R 10 , R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or a substituent group; Za and Zb each independently represent —N═ or —C(R 8 )═; R 8 represents a hydrogen atom, alkyl group, aryl group or heterocyclic group; and R 2 and R 3 , R 3 and R 6 , R 6 and R 9 , or R 4 and R 14 each independently may be bonded to each other to form a 5- to 7-membered ring.
12. The color filter according to claim 10 , wherein the azomethine-type dye represented by the formula (I) is an azomethine-type dye represented by the following formula (III):
wherein R 1 represents a hydrogen atom or a substituent group; R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent group; R 6 represents an alkyl group, alkenyl group, aryl group or heterocyclic group; R 9 , R 10 , R 11 , R 12 , R 13 and R 14 each independently represent a hydrogen atom or a substituent group; R 15 represents a hydrogen atom alkyl group, aryl group or heterocyclic group; and R 2 and R 3 , R 3 and R 6 , R 6 and R 9 , or R 4 and R 14 each independently may be bonded to each other to form a 5- to 7-membered ring.
13. The color filter according to claim 10 , wherein the tetraazaporphyrin-type dye represented by the formula (A) is a phthalocyanine dye represented by the following formula (B):
wherein M 1 represents a metal; and R 101 to R 116 each independently represent a hydrogen atom or a substituent group.
14. The color filter according to claim 10 , wherein a ratio of a mass of the azomethine-type dye represented by the formula (I) to a mass of the tetraazaporphyrin-type dye represented by the formula (A) (azomethine-type dye/tetraazaporphyrin-type dye) is in the range of from 1/9 to 9/1.
15. The color filter according to claim 10 , wherein the total concentration of (B) the organic solvent soluble dye is in the range of from 0.5% by mass to 80% by mass based on the total solid components.
16. The color filter according to claim 10 , wherein (A) the alkali-soluble binder is a resin having an unsaturated double bond in a side chain thereof.
17. The color filter according to claim 10 , wherein (E) the organic solvent comprises a cyclic ketone solvent.
18. The color filter according to claim 10 , wherein the oxime-type compound is selected from 2-(O-benzoyloxime)-1-[4-phenylthio)phenyl]-1,2-octane dione and 1-(O-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone.
19. A method of producing a color filter comprising applying the negative dye-containing cable composition according to claim 1 onto a substrate, exposing the applied negative dye-containing curable composition through a mask; and developing the exposed negative dye-containing curable composition to form a pattern.