Method of producing organic nanoparticles, organic nanoparticles thus obtained, inkjet ink for color filter, colored photosensitive resin composition and photosensitive resin transfer material, containing the same, and color filter, liquid crystal display device and CCD device, prepared using the same
A method of producing organic nanoparticles, comprising: mixing a solution of an organic material dissolved in a good solvent with a solvent that is compatible with the good solvent but is a poor solvent for the organic material, to prepare a dispersion in which the organic material is being formed to organic fine particles of a size in the order of nanometer; wherein the dispersion contains a polymer compound having a weight-average molecular weight of 1,000 or more represented by the following formula (1): wherein R 1 represents a (m+n)-valent connecting group; R 2 represents a single bond or a divalent connecting group; A 1 represents a specific monovalent organic group; when n is two or more, plural A 1 s may be the same or different; m represents 1 to 8; n represents 2 to 9; m+n is 3 to 10; and P 1 represents a polymer compound residue.
1. A method of producing organic nanoparticles, for use in production of a color filter in a liquid crystal device, comprising
dissolving an organic pigment material into a good solvent to form a solution,
mixing the solution with a poor solvent for the organic pigment, the poor solvent being compatible with the good solvent, but is the poor solvent for the organic pigment,
preparing a dispersion in which the organic pigment is being formed into organic fine particles of a size in the order of nanometer;
wherein the dispersion contains a polymer compound having a weight-average molecular weight of 1,000 or more represented by the following formula (2):
wherein R 3 represents a (x+y)-valent connecting group: R 4 and R 5 each independently represent a single bond or a divalent connecting group; A 2 is a monovalent organic group having a group selected from the group consisting of an acidic group, a nitrogen-containing basic group, a urea group, and a hydrocarbon group having 4 or more carbon atoms; when x is 2 or more, A 2 may be the same as or different from each other; y is a number of 1 to 2: x is a number of 3 to 6; and P 2 is a group derived from at least one polymer or copolymer selected from the group consisting of vinyl monomer-based polymers or copolymers, ester compound polymers, ether compound polymers, urethane compound polymers, amide compound polymers, epoxy compound polymers, silicone compound polymers, and the modified polymers and copolymers thereof:
wherein at least one compound represented by formula (D1) is added as a dispersing agent in the preparation of the organic nanoparticles in the dispersion: Formula (D1)
A-N═N—X—Y
wherein A represents a component capable of forming an azo dye together with X-Y; X represents a single bond, or a group selected from divalent connecting groups represented by structural formulae of formulae (i) to (v) set forth below; and Y represents a group represented by the following formula (D2);
wherein Z represents a lower alkylene group; —NR 21 represents a lower alkylamino group, or a nitrogen-containing, 5- or 6-membered, saturated heterocyclic group; and a represents 1 or 2,
wherein the dispersing agent is added to at least one of the solution of an organic pigment and the poor solvent, and
wherein, in the preparation of the organic fine particles in the dispersion, the organic pigment solution and the poor solvent are mixed with each other, allowing formation of the organic fine particles, and the organic fine particles are concentrated and thereafter added with the polymer compound, to give a concentrated liquid of the organic fine particles,
wherein the organic pigment particles form flocks in the concentrated liquid, after the concentration step, that are aggregated to a degree capable of re-dispersion.
2. The method of producing organic nanoparticles according to claim 1 , wherein the organic nanoparticles are particles of a pyrrolopyrrole compound pigment.
3. The method of producing organic nanoparticles according to claim 2 , wherein the pyrrolopyrrole compound pigment is a pigment represented by the following formula (V):
4. The method of producing organic nanoparticles according to claim 2 , wherein the pyrrolopyrrole compound pigment is a pigment represented by the following formula (Z):
5. The method of producing organic nanoparticles according to claim 2 , wherein the pyrrolopyrrole compound pigment is a pigment represented by the following formula (W):
6. The method of producing organic nanoparticles according to claim 1 , wherein the organic nanoparticles are particles of a dioxazine compound pigment.
7. The method of producing organic nanoparticles according to claim 6 , wherein the dioxazine compound pigment is C.I. Pigment Violet 37.
8. The method of producing organic nanoparticles according to claim 6 , wherein the dioxazine compound pigment is C.I. Pigment Violet 23.
9. The method of producing organic nanoparticles according to claim 1 , wherein the organic nanoparticles are particles of a phthalocyanine compound pigment.
10. The method of producing organic nanoparticles according to claim 9 , wherein the phthalocyanine compound pigment is C.I. Pigment green 7.
11. The method of producing organic nanoparticles according to claim 9 , wherein the phthalocyanine compound pigment is C.I. Pigment green 36.
12. The method of producing organic nanoparticles according to claim 9 , wherein the phthalocyanine compound pigment is C.I. Pigment green 15:6.
13. The method of producing organic nanoparticles according to claim 1 , wherein the polymer compound is a polymer compound having an acidic group.
14. The method of producing organic nanoparticles according to claim 1 , wherein the acidic group of the polymer compound is a carboxyl group.
15. The method of producing organic nanoparticles according to claim 1 , wherein the polymer compound has a weight-average molecular weight of 3,000 to 100,000.
16. The method of producing organic nanoparticles according to claim 1 , wherein a pigment dispersant having an amino group coexists in any of the steps, in the preparation of the organic nanoparticles in the dispersion.
17. The method of producing organic nanoparticles according to claim 1 , wherein the poor solvent for the organic pigment is a solvent selected from the group consisting of aqueous solvents, alcohol compound solvents, ketone compound solvents, ether compound solvents, ester compound solvents, and mixtures thereof.
18. The method of producing organic nanoparticles according to claim 1 , wherein the good solvent for the organic pigment is a solvent selected from the group consisting of aqueous solvents, alcohol compound solvents, ketone compound solvents, ether compound solvents, sulfoxide compound solvents, ester compound solvents, amide compound solvents, and mixtures thereof.
19. The method of producing organic nanoparticles according to claim 1 , wherein, in formation of the organic fine particles by mixing the organic pigment solution and the poor solvent, the fine particles are formed in 10 L or more of the poor solvent.
20. The method of claim 1 , wherein the flocks in the concentrated liquid are re-dispersed to be in a dispersion state that is released from an aggregation state.
21. The method of claim 1 , wherein the flocks in the concentrated liquid are re-dispersed in an organic solvent.