Curable composition, cured film, near infrared cut filter, camera module and method for manufacturing camera module
A curable composition which can be used to produce a cured film that does not easily allow a near infrared-absorbing pigment to be eluted even when the cured film is immersed in a solvent is provided. A cured film, a near infrared cut filter, a camera module, and a method for manufacturing a camera module are also provided. The curable composition includes: a near infrared-absorbing pigment (A) and a curable compound (B) having one or more atoms or groups selected from a fluorine atom, a silicon atom, a linear alkyl group having 8 or more carbon atoms, and a branched alkyl group having 3 or more carbon atoms.
1. A curable composition comprising:
a near infrared-absorbing pigment (A); and
a curable compound (B) having one or more atoms or groups selected from fluorine atom, a silicon atom, a linear alkyl group having 8 or more carbon atoms, and a branched alkyl group having 3 or more carbon atoms,
wherein the near infrared-absorbing pigment (A) is a pigment selected from the group consisting of pyrrolo-pyrrole pigments, thiol complex-based compounds, squarylium-based pigments, and croconium compounds,
the curable compound (B) has a (meth)acryloyloxy group, and
the curable compound (B) is a polymer having at least a repeating unit represented by Formula (B1),
wherein in Formula (B1), each of R 1 to R 3 independently represents a hydrogen atom, an alkyl group, or a halogen atom, L 1 represents a divalent group which includes a group represented by —CONH—, and X 1 represents a (meth)acryloyloxy group.
2. The curable composition according to claim 1 ,
wherein the curable compound (B) has a fluorine atom and/or a branched alkyl group having 6 or more carbon atoms.
3. The curable composition according to claim 1 ,
wherein the curable compound (B) further has one or more curable functional groups selected from an epoxy group, an oxetanyl group, an isocyanate group, a hydroxyl group, an amino group, a carboxyl group, a thiol group, an alkoxysilyl group, a methylol group, a vinyl group, a (meth)acrylamide group, a styryl group, and a maleimide group.
4. The curable composition according to claim 3 ,
wherein the curable compound (B) further has one or more curable functional groups selected from an epoxy group and an oxetanyl group.
5. The curable composition according to claim 1 ,
wherein the curable compound (B) has two or more curable functional groups.
6. The curable composition according to claim 1 ,
wherein the curable compound (B) contains a repeating unit represented by Formula (B2) below;
in Formula (B2), each of R 4 to R 6 independently represents a hydrogen atom, an alkyl group, or a halogen atom, L 2 represents a single bond or a divalent linking group, X 2 represents an alkyl group substituted with a fluorine atom, an aryl group substituted with a fluorine atom, an alkylsilyl group, an arylsilyl group, a group having the following partial structure (S), a linear alkyl group having 8 or more carbon atoms, or a branched alkyl group having 3 or more carbon atoms;
* represents a bonding site to other atoms.
7. The curable composition according to claim 1 ,
wherein the content of the curable compound (B) is in a range of 1% by mass to 50% by mass of all solid contents of the curable composition.
8. The curable composition according to claim 1 , further comprising:
a curable compound (C) which is different from the curable compound (B).
9. The curable composition according to claim 1 ,
wherein a maximum absorption wavelength of the near infrared-absorbing pigment (A) is in a range of 700 nm to 1000 nm.
10. The curable composition according to claim 1 ,
wherein the near infrared-absorbing pigment (A) has a hydrophobic group.
11. The curable composition according to claim 1 ,
wherein the near infrared-absorbing pigment (A) has a site having a C Log P of 5.3 or higher.
12. The curable composition according to claim 1 ,
wherein the near infrared-absorbing pigment (A) has a hydrocarbon group having a C Log P of 5.3 or higher.
13. The curable composition according to claim 1 ,
wherein the near infrared-absorbing pigment (A) is a pyrrolo-pyrrole pigment.
14. The curable composition according to claim 13 ,
wherein the pyrrolo-pyrrole pigment is a compound represented by the following formula;
in the formula, each of R 1a and R 1b independently represents a substituent having an alkyl group, an aryl group, or a heteroaryl group; each of R 2 and R 3 independently represents a cyano group or a heterocyclic group; R 4 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, substituted boron, or a metallic atom and may form a covalent bond or a coordination bond with at least one of R 1a , R 1b , and R 3 .
15. The curable composition according to claim 1 , further comprising:
at least one component selected from a polymerization initiator (D), a curing agent (E), and a solvent (F).
16. The curable composition according to claim 1 ,
wherein the total amount of all solid contents in the curable composition is in a range of 5% by mass to 50% by mass.
17. A cured film formed using the curable composition according to claim 1 .
18. A method for manufacturing a cured film comprising:
applying the curable composition according to claim 1 in a lamellar shape;
irradiating the curable composition with active radioactive rays; and/or heating the curable composition.
19. A near infrared cut filter formed using the curable composition according to claim 1 .
20. A method for manufacturing a near infrared cut filter, comprising:
applying the curable composition according to claim 1 to a substrate in a lamellar shape; and
forming a pattern image by exposing the lamellar curable composition through a mask and then developing the curable composition.
21. A camera module comprising:
a solid-state imaging element and the near infrared cut filter according to claim 19 .
22. A method for manufacturing a camera module including a solid-state imaging element and a near infrared cut filter, comprising:
forming the near infrared cut filter by applying the curable composition according to claim 1 on a light-receiving side of the solid-state imaging element.
23. The curable composition according to claim 1 , wherein the weight-average molecular weight of the curable compound (B) is in a range of 5,000 to 100,000.
24. The curable composition according to claim 1 , wherein the curable compound (B) has a fluorine atom.
25. The curable composition according to claim 1 , wherein the near infrared-absorbing pigment (A) is a compound represented by Formula (A2),
wherein in Formula (A2), each of R 10 's independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, substituted boron, or a metal atom and may form a covalent bond or a coordination bond with R 12 ; each of R 11 and R 12 independently represents a hydrogen atom or a substituent, at least one of R 11 and R 12 is an electron-withdrawing group, and R 11 and R 12 may bond to each other and thus form a ring; and each of R's independently represents a branched alkyl group having 3 to 30 carbon atoms.
26. The curable composition according to claim 1 , wherein the near infrared-absorbing pigment (A) is a compound represented by Formula (A3),
wherein in Formula (A3), each of R 20 's independently represents a branched alkyl group having 3 to 30 carbon atoms, and each Ph represents a phenyl group.
27. The curable composition according to claim 1 ,
wherein the near infrared-absorbing pigment (A) is a pigment selected from the group consisting of pyrrolo-pyrrole pigments, copper compounds, and croconium compounds.
28. The curable composition according to claim 1 ,
wherein the content of the near infrared-absorbing pigment (A) is in a range of 0.5% by mass to 15% by mass of all solid contents in the composition.
29. The curable composition according to claim 1 ,
wherein X 1 represents an acryloyloxy group.
30. The curable composition according to claim 1 ,
wherein the curable composition further comprises an oxime compound.
31. The curable composition according to claim 1 ,
wherein the curable composition further comprises a curable compound (C) which is different from the curable compound (B), wherein the curable compound (C) contains a tri- or higher functional (meth)acrylate compound.
32. The curable composition according to claim 1 ,
wherein X 1 represents an acryloyloxy group, and
the near infrared-absorbing pigment (A) is a pyrrolo-pyrrole pigment represented by the following formula;
in the formula, each of R 1a and R 1b independently represents a substituent having an alkyl group, an aryl group, or a heteroaryl group; each of R 2 and R 3 independently represents a cyano group or a heterocyclic group; R 4 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, substituted boron, or a metallic atom and may form a covalent bond or a coordination bond with at least one of R 1a , R 1b , and R 3 .