# US 2024/0199889 A1 · Composition for forming colored layer, optical film, and display device

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- Number: US 2024/0199889 A1
- Document ID: US20240199889A1
- Status: Published application
- Kind: A1
- Application number: 18/440,204
- Filed: 2024-02-13
- Published: 2024-06-20
- Earliest claimed: 2021-08-17
- Assignees: Toppan Inc.
- Applicants: Toppan Inc.
- Inventors: Kai FUTAMATA; Yoshiko ISHIMARU; Takenori GODA; Shigeki FURUKAWA; Hanae TAGAMI
- Web page: https://patentgrep.com/patent/US20240199889A1

## CPC

- C09D 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
- H10K 50/86: Arrangements for improving contrast, e.g. preventing reflection of ambient light
- C08F 2/44: Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
- C08F 2/50: with sensitising agents
- C08F 220/14: Methyl esters {, e.g. methyl (meth)acrylate}
- C08J 7/042: {with two or more layers, where at least one layer of a composition contains a polymer binder}
- C08J 7/046: Forming abrasion-resistant coatings; Forming surface-hardening coatings
- C08J 7/048: Forming gas barrier coatings
- C09D 5/006: {Anti-reflective coatings}
- C09D 5/16: Antifouling paints; Underwater paints
- C09D 7/41: Organic pigments; Organic dyes
- C09D 7/61: inorganic
- C09D 135/02: Homopolymers or copolymers of esters (C09D135/06, C09D135/08 take precedence)
- G02B 1/113: using inorganic layer materials only
- G02B 5/223: {containing organic substances, e.g. dyes, inks or pigments}
- G09F 9/30: in which the desired character or characters are formed by combining individual elements (panels comprising a number of electrodes in a single cell controlling light arriving from an independent light source, e.g. electro-optical or magneto-optical cell, G02F1/00)
- C08J 2301/12: Cellulose acetate
- C08J 2333/12: Homopolymers or copolymers of methyl methacrylate
- C08J 2367/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence)
- C08J 2429/04: Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
- C08J 2433/06: of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C08J 2433/12: Homopolymers or copolymers of methyl methacrylate
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G09F: DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS

## Abstract

A composition for forming a colored layer includes a dye, an ionizing radiation-curable resin, a photoinitiator, and a solvent. The dye contains a first colorant and a second colorant, the first colorant has a wavelength of maximum absorption in a range of 470 nm to 530 nm, and an absorption spectrum with a full width at half maximum of 15 nm to 45 nm, the second colorant has a wavelength of maximum absorption in a range of 560 nm to 620 nm, and an absorption spectrum with a full width at half maximum of 15 nm to 55 nm, and the ionizing radiation-curable resin contains a resin having an amine structure.

## Claims

### Claim 1

A composition for forming a colored layer, comprising:
a dye (A), an ionizing radiation-curable resin (B), a photoinitiator (C), and a solvent (D), wherein
the dye (A) contains a first colorant and a second colorant,
the first colorant has a wavelength of maximum absorption in a range of 470 nm to 530 nm, and an absorption spectrum with a full width at half maximum of 15 nm to 45 nm,
the second colorant has a wavelength of maximum absorption in a range of 560 nm to 620 nm, and an absorption spectrum with a full width at half maximum of 15 nm to 55 nm, and
the ionizing radiation-curable resin (B) contains a resin having an amine structure.

### Claim 2 (depends on 1)

The composition for forming the colored layer of claim 1, wherein
the ionizing radiation-curable resin (B) is a polymer containing a structural unit represented by following formula (1),
[where R1 represents a hydrogen atom, halogen atom, carboxyl group, sulfo group, cyano group, hydroxy group, alkyl group having 10 or fewer carbon atoms, alkoxycarbonyl group having 10 or fewer carbon atoms, alkylsulfonylaminocarbonyl group having 10 or fewer carbon atoms, arylsulfonylaminocarbonyl group, alkylsulfonyl group, arylsulfonyl group, acylaminosulfonyl group having 10 or fewer carbon atoms, alkoxy group having 10 or fewer carbon atoms, alkylthio group having 10 or fewer carbon atoms, aryloxy group having 10 or fewer carbon atoms, nitro group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, acyloxy group having 10 or fewer carbon atoms, acyl group having 10 or fewer carbon atoms, carbamoyl group, sulfamoyl group, aryl group having 10 or fewer carbon atoms, substituted amino group, substituted ureido group, substituted phosphono group, or a heterocyclic group; R2 represents a hydrogen atom or an alkyl group having 30 or fewer carbon atoms; and X represents a single bond, an ester group, an aliphatic alkyl chain having 30 or fewer carbon atoms, an aromatic chain, a polyethylene glycol chain, or a linking group formed by combination thereof, and any of these may contain a spirodioxane ring.]

### Claim 3 (depends on 1)

The composition for forming the colored layer of claim 1, wherein
the ionizing radiation-curable resin (B) further contains a polymer having a structural unit represented by following formula (2),
[where R3 represents a hydrogen atom, halogen atom, carboxyl group, sulfo group, cyano group, hydroxy group, alkyl group having 10 or fewer carbon atoms, alkoxycarbonyl group having 10 or fewer carbon atoms, alkylsulfonylaminocarbonyl group having 10 or fewer carbon atoms, arylsulfonylaminocarbonyl group, alkylsulfonyl group, arylsulfonyl group, acylaminosulfonyl group having 10 or fewer carbon atoms, alkoxy group having 10 or fewer carbon atoms, alkylthio group having 10 or fewer carbon atoms, aryloxy group having 10 or fewer carbon atoms, nitro group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, acyloxy group having 10 or fewer carbon atoms, acyl group having 10 or fewer carbon atoms, carbamoyl group, sulfamoyl group, aryl group having 10 or fewer carbon atoms, substituted amino group, substituted ureido group, substituted phosphono group, or a heterocyclic group; R4 represents a hydrogen atom or an alkyl group having 30 or fewer carbon atoms; and X represents a single bond, an ester group, an aliphatic alkyl chain having 30 or fewer carbon atoms, an aromatic chain, a polyethylene glycol chain, or a linking group formed by combination thereof, and any of these may contain a spirodioxane ring.]

### Claim 4 (depends on 1)

The composition for forming the colored layer of claim 1, further comprising one or more additives (E) selected from a radical scavenger, a peroxide decomposer, and a singlet oxygen quencher.

### Claim 5 (depends on 4)

The composition for forming the colored layer of claim 4, wherein
the singlet oxygen quencher is a dialkyl phosphate, dialkyldithiocarbamate, or benzenedithiol, or a transition metal complex thereof.

### Claim 6 (depends on 1)

The composition for forming the colored layer of claim 1, wherein
the dye (A) contains one or more selected from the group consisting of compounds having a porphyrin structure, merocyanine structure, phthalocyanine structure, azo structure, cyanine structure, squarylium structure, coumarin structure, polyene structure, quinone structure, tetradiporphyrin structure, pyrromethene structure, and indigo structure; and a metal complex thereof.

### Claim 7 (depends on 1)

The composition for forming the colored layer of claim 1, wherein
the dye (A) further contains a third colorant whose wavelength of lowest transmittance within a wavelength range of 380 nm to 780 nm is within a range of 650 nm to 780 nm.

### Claim 8 (depends on 1)

An optical film, comprising:
a colored layer that is a cured product of the composition for forming the colored layer of claim 1;
a transparent substrate located on one surface of the colored layer; and
a functional layer located on one or the other surface of the colored layer, wherein
one or both of the transparent substrate and the functional layer have an ultraviolet shielding rate of 85% or higher as measured according to a method described in JIS L 1925, and
the functional layer functions as an antireflection layer or an antiglare layer.

### Claim 9 (depends on 8)

The optical film of claim 8, further comprising an oxygen barrier layer having an oxygen permeability of 10 cm3/(m2·day·atm) or lower as the functional layer.

### Claim 10 (depends on 8)

The optical film of claim 8, further comprising an antistatic layer or an antifouling layer as the functional layer.

### Claim 11 (depends on 8)

A display device comprising the optical film of claim 8.

### Claim 12

A composition for forming a colored layer, comprising:
a dye (A), an ionizing radiation-curable resin (B), a photoinitiator (C), and a solvent (D), wherein
the dye (A) contains at least one of
a first colorant having a wavelength of maximum absorption in a first range of 470 nm to 530 nm, and an absorption spectrum with a full width at half maximum of 15 nm to 45 nm,
a second colorant having a wavelength of maximum absorption in a second range of 560 nm to 620 nm, and an absorption spectrum with a full width at half maximum of 15 nm to 55 nm, and
a third colorant whose wavelength of minimum transmittance within a wavelength range of 380 nm to 780 nm is within a third range of 650 nm or higher and 780 nm or lower,
minimum transmittance is 1% or higher and lower than 50% in only one of the first to third ranges, and
the ionizing radiation-curable resin (B) contains a resin having an amine structure.

### Claim 13 (depends on 12)

The composition for forming the colored layer of claim 12, wherein
the ionizing radiation-curable resin (B) is a polymer containing a structural unit represented by following formula (1),
[where R1 represents a hydrogen atom, halogen atom, carboxyl group, sulfo group, cyano group, hydroxy group, alkyl group having 10 or fewer carbon atoms, alkoxycarbonyl group having 10 or fewer carbon atoms, alkylsulfonylaminocarbonyl group having 10 or fewer carbon atoms, arylsulfonylaminocarbonyl group, alkylsulfonyl group, arylsulfonyl group, acylaminosulfonyl group having 10 or fewer carbon atoms, alkoxy group having 10 or fewer carbon atoms, alkylthio group having 10 or fewer carbon atoms, aryloxy group having 10 or fewer carbon atoms, nitro group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, acyloxy group having 10 or fewer carbon atoms, acyl group having 10 or fewer carbon atoms, carbamoyl group, sulfamoyl group, aryl group having 10 or fewer carbon atoms, substituted amino group, substituted ureido group, substituted phosphono group, or a heterocyclic group; R2 represents a hydrogen atom or an alkyl group having 30 or fewer carbon atoms; and X represents a single bond, an ester group, an aliphatic alkyl chain having 30 or fewer carbon atoms, an aromatic chain, a polyethylene glycol chain, or a linking group formed by combination thereof, and any of these may contain a spirodioxane ring.]

### Claim 14 (depends on 12)

The composition for forming the colored layer of claim 12, wherein
the ionizing radiation-curable resin (B) further contains a polymer having a structural unit represented by following formula (2),
[where R3 represents a hydrogen atom, halogen atom, carboxyl group, sulfo group, cyano group, hydroxy group, alkyl group having 10 or fewer carbon atoms, alkoxycarbonyl group having 10 or fewer carbon atoms, alkylsulfonylaminocarbonyl group having 10 or fewer carbon atoms, arylsulfonylaminocarbonyl group, alkylsulfonyl group, arylsulfonyl group, acylaminosulfonyl group having 10 or fewer carbon atoms, alkoxy group having 10 or fewer carbon atoms, alkylthio group having 10 or fewer carbon atoms, aryloxy group having 10 or fewer carbon atoms, nitro group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, acyloxy group having 10 or fewer carbon atoms, acyl group having 10 or fewer carbon atoms, carbamoyl group, sulfamoyl group, aryl group having 10 or fewer carbon atoms, substituted amino group, substituted ureido group, substituted phosphono group, or a heterocyclic group; R4 represents a hydrogen atom or an alkyl group having 30 or fewer carbon atoms; and X represents a single bond, an ester group, an aliphatic alkyl chain having 30 or fewer carbon atoms, an aromatic chain, a polyethylene glycol chain, or a linking group formed by combination thereof, and any of these may contain a spirodioxane ring.]

### Claim 15 (depends on 12)

The composition for forming the colored layer of claim 12, further comprising one or more additives (E) selected from a radical scavenger, a peroxide decomposer, and a singlet oxygen quencher.

### Claim 16 (depends on 15)

The composition for forming the colored layer of claim 15, wherein
the singlet oxygen quencher is a dialkyl phosphate, dialkyldithiocarbamate, or benzenedithiol, or a transition metal complex thereof.

### Claim 17 (depends on 12)

The composition for forming the colored layer of claim 12, wherein
the dye (A) contains one or more selected from the group consisting of compounds having a porphyrin structure, merocyanine structure, phthalocyanine structure, azo structure, cyanine structure, squarylium structure, coumarin structure, polyene structure, quinone structure, tetradiporphyrin structure, pyrromethene structure, and indigo structure; and a metal complex thereof.

### Claim 18 (depends on 12)

An optical film, comprising:
a colored layer that is a cured product of the composition for forming the colored layer of claim 12;
a transparent substrate located on one surface of the colored layer; and
a functional layer located on one or the other surface of the colored layer, wherein
one or both of the transparent substrate and the functional layer have an ultraviolet shielding rate of 85% or higher as measured according to a method described in JIS L 1925, and
the functional layer functions as an antireflection layer or an antiglare layer.

### Claim 19 (depends on 18)

The optical film of claim 18, further comprising an oxygen barrier layer having an oxygen permeability of 10 cm3/(m2·day·atm) or lower as the functional layer.

### Claim 20 (depends on 18)

The optical film of claim 18, further comprising an antistatic layer or an antifouling layer as the functional layer.

### Claim 21 (depends on 18)

A display device comprising the optical film of claim 18.
