Azo compound, colorant-containing curable composition, and color filter and method of producing the same
View Patent ↗The present invention provides a novel azo compound, a curable composition comprising a colorant superior in the light-fastness and heat resistance of a dye, pattern-forming characteristics (developing characteristics) and liquid preserving characteristics, a color filter using the curable composition and a method of producing the color filter.
1. An azo compound represented by the following formula (I):
wherein R 1 and R 2 respectively represent a hydrogen atom, an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms or an aralkyl group having 7 to 21 carbon atoms and R 1 and R 2 may form a hetero ring with nitrogen atoms bonded therewith; R 3 represents a halogen atom, a trihalomethyl group, an alkoxy group having 1 to 21 carbon atoms or a nitro group; R 4 represents a halogen atom or a —SO 3 M group; M represents a metal atom cation or a cation comprising a nitrogen-containing compound; m denotes an integer from 0 to 5; and n denotes an integer from 0 to 4.
2. A colorant-containing curable composition comprising a colorant, wherein the colorant contains a compound represented by the following formula (I):
wherein R 1 and R 2 respectively represent a hydrogen atom, an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms or an aralkyl group having 7 to 21 carbon atoms and R 1 and R 2 may form a hetero ring with nitrogen atoms bonded therewith; R 3 represents a halogen atom, a trihalomethyl group, an alkoxy group having 1 to 21 carbon atoms or a nitro group; R 4 represents a halogen atom or a —SO 3 M group; M represents a metal atom cation or a cation comprising a nitrogen-containing compound; m denotes an integer from 0 to 5; and n denotes an integer from 0 to 4.
3. A colorant-containing curable composition according to claim 2 , the composition further comprising a monomer.
4. A colorant-containing curable composition according to claim 3 , wherein said monomer contains a (meth)acrylate type monomer.
5. A colorant-containing curable composition according to claim 3 , wherein said monomer contains a (meth)acrylate type monomer that is at least tetra-functional.
6. A colorant-containing curable composition according to claim 2 , the composition further comprising a binder.
7. A colorant-containing curable composition according to claim 6 , wherein said binder comprises an alkali-soluble (meth)acryl type resin.
8. A colorant-containing curable composition according to claim 6 , wherein said binder contains an alkali-soluble (meth)acryl type resin having a polymerizable side chain.
9. A colorant-containing curable composition according to claim 2 , the composition further comprising a photoinitiator.
10. A colorant-containing curable composition according to claim 9 , wherein said photoinitiator is at least one compound selected from the group consisting of a trihalomethyltriazine compound, a benzyldimethylketal compound, an α-hydroxyketone compound, an α-aminoketone compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a triallylimidazole dimer, a benzothiazole compound, a benzophenone compound, an acetophenone compound and its derivative, a cyclopentadiene-benzene-iron complex and its salt, a halomethyloxadiazole compound, and a 3-aryl substituted cumarin compound.
11. A colorant-containing curable composition according to claim 9 , wherein said photoinitiator contains at least one compound generating no acid by decomposition.
12. A colorant-containing curable composition according to claim 9 , wherein said photoinitiator is at least one compound selected from the group consisting of an α-aminoketone compound, a phosphine oxide type compound, a metallocene compound, an oxime type compound and a triallylimidazole dimer.
13. A colorant-containing curable composition according to claim 2 , the composition further comprising a crosslinking agent.
14. A positive type colorant-containing curable composition, the composition comprising a compound represented by the formula (I), a photosensitizer and a solvent.
15. A positive type colorant-containing curable composition according to claim 14 , wherein said photosensitizer is an o-benzoquinonediazide sulfonate or an o-naphthoquinonediazide sulfonate.
16. A positive type colorant-containing curable composition according to claim 15 , the composition further comprising a hardener.
17. A positive type colorant-containing curable composition, the composition comprising a compound represented by the formula (I), a photo-acid generating agent and a hardener.
18. A color filter comprising a compound represented by the following formula (I):
wherein R 1 and R 2 respectively represent a hydrogen atom, an alkyl group having 1 to 21 carbon atoms, an alkenyl group having 2 to 21 carbon atoms, an aryl group having 6 to 21 carbon atoms or an aralkyl group having 7 to 21 carbon atoms and R 1 and R 2 may form a hetero ring with nitrogen atoms bonded therewith; R 3 represents a halogen atom, a trihalomethyl group, an alkoxy group having 1 to 21 carbon atoms or a nitro group; R 4 represents a halogen atom or a —SO 3 M group; M represents a metal atom cation or a cation comprising a nitrogen-containing compound; m denotes an integer from 0 to 5; and n denotes an integer from 0 to 4.
19. A color filter comprising the colorant-containing curable composition as claimed in claim 2 .
20. A method of producing a color filter, the method comprising applying the colorant-containing curable composition as claimed in claim 2 to a support, then exposing the composition to light through a mask and developing the composition to form a pattern.