Coloring resin composition, film, color filter, solid-state imaging element, and image display device
Provided are a coloring resin composition including a resin, a coloring material, and a solvent, in which the resin is a polyimide or polyimide precursor including a repeating unit represented by Formula (1-1) or Formula (1-2), and a content of the coloring material is 30 mass % or more with respect to a total solid content of the composition; a film; a color filter; a solid-state imaging element; and an image display device.
1. A coloring resin composition comprising:
a resin;
a coloring material; and
a solvent,
wherein the resin is a polyimide or polyimide precursor including a repeating unit represented by Formula (1-1) or Formula (1-2), and
a content of the coloring material is 30 mass % or more with respect to a total solid content of the composition,
in Formula (1-1), R 11 represents an aromatic hydrocarbon group having 6 to 14 carbon atoms, R 12 represents a monovalent substituent which is a substituent on the aromatic hydrocarbon group in R 11 , n represents an integer of 1 to nA, nA is a maximum number of substitutions of the aromatic hydrocarbon group in R 11 , and R 13 represents a tetravalent organic group,
in Formula (1-2), R 21 represents an aromatic hydrocarbon group having 6 to 14 carbon atoms, R 22 represents a monovalent substituent which is a substituent on the aromatic hydrocarbon group in R 21 , m represents an integer of 1 to mA, mA is a maximum number of substitutions of the aromatic hydrocarbon group in R 21 , R 23 represents a tetravalent organic group, and R 24 each independently represents a monovalent substituent,
wherein the resin includes at least one repeating unit selected from the group consisting of a repeating unit 1-1b which is the repeating unit represented by Formula (1-1) and in which R 12 in Formula (1-1) is a group R 1b including at least one curable group selected from the group consisting of a (meth)acryloxy group, a (meth)acrylamide group, an aromatic vinyl group, a maleimide group, an epoxy group, and an oxetanyl group, and a repeating unit 1-2b which is the repeating unit represented by Formula (1-2) and in which R 22 in Formula (1-2) is R 1b , or
wherein the resin includes at least one repeating unit selected from the group consisting of a repeating unit 1-1c which is the repeating unit represented by Formula (1-1) and in which R 12 in Formula (1-1) is a group R 1c having 12 or more carbon atoms, and a repeating unit 1-2c which is the repeating unit represented by Formula (1-2) and in which R 22 in Formula (1-2 is R 1c .
2. The coloring resin composition according to claim 1 ,
wherein the resin includes at least one repeating unit selected from the group consisting of a repeating unit 1-1a which is the repeating unit represented by Formula (1-1) and in which R 12 in Formula (1-1) is a group R 1a including at least one acid group selected from the group consisting of a carboxy group, a sulfo group, a phosphoric acid group, a sulfonamide group, and a hydroxy group, and a repeating unit 1-2a which is the repeating unit represented by Formula (1-2) and in which R 22 in Formula (1-2) is R 1a .
3. The coloring resin composition according to claim 1 ,
wherein R 1c includes at least one selected from the group consisting of a repeating unit derived from a (meth)acrylic acid ester compound, a repeating unit derived from a (meth)acrylamide compound, a repeating unit derived from an aromatic vinyl compound, and a polyester structure.
4. The coloring resin composition according to claim 1 ,
wherein R 13 and R 23 are groups including an alicyclic structure, or groups including a fluorine atom and an aromatic ring structure.
5. The coloring resin composition according to claim 1 ,
wherein R 24 is a group including at least one acid group selected from the group consisting of a carboxy group, a sulfo group, a phosphoric acid group, a sulfonamide group, and a hydroxy group, a group including at least one curable group selected from the group consisting of a (meth)acryloxy group, a (meth)acrylamide group, an aromatic vinyl group, a maleimide group, an epoxy group, and an oxetanyl group, or a group having 12 or more carbon atoms.
6. The coloring resin composition according to claim 1 ,
wherein an acid value of the resin is 20 to 150 mgKOH/g.
7. The coloring resin composition according to claim 1 ,
wherein a C═C value of the resin is 0.1 mmol/g to 3 mmol/g.
8. The coloring resin composition according to claim 1 ,
wherein a weight-average molecular weight of the resin is 5,000 to 20,000.
9. The coloring resin composition according to claim 1 ,
wherein, as the resin, the following resin 1 and resin 2 are included,
resin 1: a resin including at least one acid group selected from the group consisting of a carboxy group, a sulfo group, a phosphoric acid group, a sulfonamide group, and a hydroxy group and at least one curable group selected from the group consisting of a (meth)acryloxy group, a (meth)acrylamide group, an aromatic vinyl group, a maleimide group, an epoxy group, and an oxetanyl group,
resin 2: a resin including at least one acidic group selected from the group consisting of a carboxy group, a sulfo group, a phosphoric acid group, a sulfonamide group, and a hydroxy group and a group having 12 or more carbon atoms.
10. The coloring resin composition according to claim 1 ,
wherein the coloring material is an organic pigment.
11. The coloring resin composition according to claim 1 ,
wherein the coloring material includes at least one selected from a chromatic coloring material or a near-infrared absorbing coloring material.
12. The coloring resin composition according to claim 1 ,
wherein the coloring material includes a chromatic coloring material and a near-infrared absorbing coloring material.
13. The coloring resin composition according to claim 1 ,
wherein the coloring material includes a black coloring material.
14. The coloring resin composition according to claim 1 ,
wherein the coloring material includes at least one coloring material selected from the group consisting of a red coloring material, a yellow coloring material, a blue coloring material, and a violet coloring material.
15. The coloring resin composition according to claim 1 , further comprising:
a photopolymerization initiator.
16. The coloring resin composition according to claim 15 ,
wherein the photopolymerization initiator is an oxime initiator.
17. The coloring resin composition according to claim 1 ,
wherein the solvent includes at least one solvent selected from the group consisting of propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, cyclohexanone, cyclopentanone, butyl acetate, ethyl 3-ethoxypropionate, propylene glycol monoethyl ether acetate, ethyl lactate, 3-methoxybutanol, methyl isobutyl ketone, and dipropylene glycol monomethyl ether.
18. A film formed of the coloring resin composition according to claim 1 .
19. A color filter comprising:
the film according to claim 18 .
20. A solid-state imaging element comprising:
the film according to claim 18 .
21. An image display device comprising:
the film according to claim 18 .
22. A polyimide or a polyimide precursor comprising:
a repeating unit represented by Formula (2-1) or Formula (2-2),
in Formula (2-1), R 11 represents an aromatic hydrocarbon group having 6 to 14 carbon atoms, L 1 represents a group represented by Formula (L-1), Formula (L-2), or Formula (L-3), P 1 represents a molecular chain having a weight-average molecular weight of 1,000 to 10,000 and having no acid group and basic group, n1 is 1 or 2, R 14 represents a monovalent substituent which is a substituent on the aromatic hydrocarbon group in R 11 , m1 represents an integer of 0 to nA1, nA1 is a number obtained by subtracting n1 from a maximum number of substitutions of the aromatic hydrocarbon group in R 1 , and R 13 represents a tetravalent organic group,
in Formula (2-2), R 21 represents an aromatic hydrocarbon group having 6 to 14 carbon atoms, L 2 represents a group represented by Formula (L-1), Formula (L-2), or Formula (L-3), P 2 represents a molecular chain having a weight-average molecular weight of 1,000 to 10,000 and having no acid group and basic group, n2 is 1 or 2, R 25 represents a monovalent substituent which is a substituent on the aromatic hydrocarbon group in R 21 , m2 represents an integer of 0 to nA2, nA2 is a number obtained by subtracting n2 from a maximum number of substitutions of the aromatic hydrocarbon group in R 21 , R 23 represents a tetravalent organic group, and R 24 each independently represents a monovalent substituent,
in Formula (L-1), Formula (L-2), or Formula (L-3), X t represents —O— or —NR N —, L 3 represents a single bond, —O—, —NR N —, —S—, —C(═O)—, —NR N (C═O)O—, —CH 2 —CH(OH)—CH 2 —, a hydrocarbon group, or a group of a combination of two or more these groups, * represents a bonding site with R 11 or R 21 , ● represents a bonding site with P 1 or P 2 , and R N represents a hydrogen atom or a hydrocarbon group.
23. A polyimide or polyimide precursor comprising a repeating unit represented by Formula (1-1) or Formula (1-2),
in Formula (1-1), R 11 represents an aromatic hydrocarbon group having 6 to 14 carbon atoms, R 12 represents a monovalent substituent which is a substituent on the aromatic hydrocarbon group in R 11 , R 12 is R 1a or R 1b , n represents an integer of 1 to nA, nA is a maximum number of substitutions of the aromatic hydrocarbon group in R 11 , and R 13 represents a tetravalent organic group,
in Formula (1-2), R 21 represents an aromatic hydrocarbon group having 6 to 14 carbon atoms, R 22 represents a monovalent substituent which is a substituent on the aromatic hydrocarbon group in R 21 , R 21 is R 1a or R 1b , m represents an integer of 1 to mA, mA is a maximum number of substitutions of the aromatic hydrocarbon group in R 21 , R 23 represents a tetravalent organic group, and R 24 each independently represents a monovalent substituent,
R 1a : a group represented by Formula (A-1),
R 1b : a group represented by Formula (B-1),
in Formula (A-1), L a1 represents a single bond or an (na+1)-valent linking group, A a1 each independently represents a carboxy group, a phosphoric acid group, or a sulfonamide group, na represents an integer of 1 or more, and * represents a bonding site with R 11 ,
in Formula (B-1), L b1 represents a single bond or an (nb+1)-valent linking group, A b1 each independently represent at least one curable group selected from the group consisting of a (meth)acryloxy group, a (meth)acrylamide group, an aromatic vinyl group, a maleimide group, an epoxy group, and an oxetanyl group, nb represents an integer of 1 or more, and * represents a bonding site with R 11 .