# US 12,006,386 B2 · Alkali soluble, photo-curable and thermo-curable copolymer, and photosensitive resin composition, photosensitive resin film and color filter using the same

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- Number: US 12,006,386 B2
- Document ID: US12006386B2
- Status: Granted
- Kind: B2
- Application number: 17/058,473
- Filed: 2020-03-20
- Published: 2021-07-01
- Granted: 2024-06-11
- Earliest claimed: 2019-03-27
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Hye Jin Park; Changho Cho
- Web page: https://patentgrep.com/patent/US12006386B2

## CPC

- C08F 220/32: containing epoxy radicals
- G03F 7/0388: {with ethylenic or acetylenic bands in the side chains of the photopolymer}
- C08F 2/50: with sensitising agents
- C08F 220/18: with acrylic or methacrylic acids
- C08F 220/1807: {C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate}
- C08F 265/06: Polymerisation of acrylate or methacrylate esters on to polymers thereof
- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- 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
- G03F 7/00: Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor (using photoresist structures for special production processes, see the relevant places, e.g. B44C, H10P76/00, H05K)
- G03F 7/0007: {Filters, e.g. additive colour filters; Components for display devices}
- G03F 7/028: with photosensitivity-increasing substances, e.g. photoinitiators
- G03F 7/033: the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
- G03F 7/038: Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021)
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- C08J 2333/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- 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)
- 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)

## Abstract

The present invention relates to an alkali soluble, photo-curable and thermo-curable copolymer containing three types of (meth)acrylate repeating units classified by the type of functional groups present at the terminal, and a photosensitive resin composition, a photosensitive resin film, and a color filter using the same.

## Claims

### Claim 1

An alkali soluble, photo-curable and thermo-curable copolymer comprising:
a first (meth)acrylate repeating unit having a branched chain in which an organic functional group including an epoxy group is bonded to a terminal of the branched chain;
a second (meth)acrylate repeating unit having a branched chain in which an organic functional group including an alkenyl group is bonded to a terminal of the branched chain; and
a third (meth)acrylate repeating unit having a branched chain in which an organic functional group including an alkenyl group is bonded to a terminal of the branched chain,
wherein in the second (meth)acrylate repeating unit, the branched chain includes any one functional group selected from an alkyl ester group having 1 to 20 carbon atoms substituted with a hydroxy group; an oxyalkyl ester group having 1 to 20 carbon atoms substituted with a hydroxy group; an alkyl ester group substituted by a cycloalkyl group having 3 to 30 carbon atoms substituted with a hydroxy group; a polycyclic alkyl ester group having 7 to 30 carbon atoms substituted with a hydroxy group; and an alkyl ester group substituted by a polycyclic alkyloxy group having 7 to 30 carbon atoms substituted with a hydroxy group,
wherein in the third (meth)acrylate repeating unit, the branched chain includes any one functional group selected from an alkyl ester group having 1 to 20 carbon atoms in which a substituent containing a carboxyl group is introduced to the terminal; an oxyalkyl ester group having 1 to 20 carbon atoms in which a substituent containing a carboxyl group is introduced to the terminal; an alkyl ester group substituted by a cycloalkyl group having 3 to 30 carbon atoms in which a substituent containing a carboxyl group is introduced to the terminal; a polycyclic alkyl ester group having 7 to 30 carbon atoms in which a substituent containing a carboxyl group is introduced to the terminal; and an alkyl ester group substituted by a polycyclic alkyloxy group having 7 to 30 carbon atoms in which a substituent containing a carboxyl group is introduced to the terminal, and
wherein the organic functional group including the epoxy group includes any one functional group of a functional group represented by Chemical Formula 2 and a functional group represented by Chemical Formula 3:
in the Chemical Formula 2, R4, and R5 are each independently a direct bond, or an alkylene group having 1 to 5 carbon atoms,
in the Chemical Formula 3, R6, and R7 are each independently a direct bond, or an alkylene group having 1 to 5 carbon atoms, and X is a direct bond, —O—, or —S—.

### Claim 2 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein the first (meth)acrylate repeating unit is contained in an amount of at least 5 mol % based on the total of the repeating units contained in the copolymer.

### Claim 3 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein a molar content of the first (meth)acrylate repeating unit is 20 moles or more and 500 moles or less based on the total mole number 100 moles of the second (meth)acrylate repeating unit and the third (meth)acrylate repeating unit.

### Claim 4 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein the branched chain in the first (meth)acrylate repeating unit includes any one functional group selected from a carbonyl group; an alkyl ester group having 1 to 20 carbon atoms; and an oxyalkyl ester group having 1 to 20 carbon atoms.

### Claim 5 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein the first (meth)acrylate repeating unit is represented by Chemical Formula 4:
in the Chemical Formula 4,
R8 to R10 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms,
L1 is a direct bond, an alkylene group having 1 to 20 carbon atoms or an oxyalkylene group having 1 to 20 carbon atoms, and
R11 is the organic functional group including an epoxy group.

### Claim 6 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein the organic functional group including the alkenyl group contained in the second (meth)acrylate repeating unit and the third (meth)acrylate repeating unit includes a (meth)acryloyl group or a (meth)acryloyloxy group.

### Claim 7 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein the second (meth)acrylate repeating unit is represented by Chemical Formula 5:
in the Chemical Formula 5, R12 to R14 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms,
L2 is a direct bond, an alkylene group having 1 to 20 carbon atoms, or an oxyalkylene group having 1 to 20 carbon atoms,
L3 is an alkylene group having 1 to 20 carbon atoms substituted with a hydroxy group, an oxyalkylene group having 1 to 20 carbon atoms substituted with a hydroxy group, a cycloalkylene group having 3 to 30 carbon atoms substituted with a hydroxy group, or a polycyclic alkylene group having 7 to 30 carbon atoms substituted with a hydroxy group, and
R15 is the organic functional group including an alkenyl group.

### Claim 8 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein the substituent containing a carboxyl group at the terminal contained in the third (meth)acrylate repeating unit is represented by Chemical Formula 6:
in the Chemical Formula 6,
R16 and R17 are each independently hydrogen, or are bonded to each other to form an aliphatic ring or aromatic ring.

### Claim 9 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein the third (meth)acrylate repeating unit is represented by Chemical Formula 7:
in the Chemical Formula 7,
R18 to R20 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms,
L4 is a direct bond, an alkylene group having 1 to 20 carbon atoms, or an oxyalkylene groups having 1 to 20 carbon atoms,
L5 is an alkylene group having 1 to 20 carbon atoms in which a substituent containing a carboxyl group at the terminal is introduced to a terminal end of the alkylene group, an oxyalkylene group having 1 to 20 carbon atoms in which a substituent containing a carboxy group at the terminal is introduced to a terminal end of the oxyalkylene group, a cycloalkylene group having 3 to 30 carbon atoms in which a substituent containing a carboxy group is introduced to a terminal end of the cycloalkylene group, or a polycyclic alkylene group having 7 to 30 carbon atoms in which a substituent containing a carboxyl group is introduced to a terminal end of the polycyclic alkylene group, and
R21 is the organic functional group including an alkenyl group.

### Claim 10 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein a molar ratio between the second (meth)acrylate repeating unit and the third (meth)acrylate repeating unit is 99:1 to 1:99.

### Claim 11 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein a molar ratio between the first (meth)acrylate repeating unit and the third (meth)acrylate repeating unit is 99:1 to 1:19.

### Claim 12 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein a molar ratio between the first (meth)acrylate repeating unit and the second (meth)acrylate repeating unit is 99:1 to 1:19.

### Claim 13 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, wherein an acid value of the copolymer is 20 KOH mg/g to 150 KOH mg/g.

### Claim 14 (depends on 1)

The alkali soluble, photo-curable and thermo-curable copolymer according to claim 1, further comprising one or more repeating units selected from the group consisting of:
a fourth (meth)acrylate repeating unit represented by Chemical Formula 8;
a maleimide repeating unit represented by Chemical Formula 9; and
one or more repeating units selected from the group consisting of vinyl repeating units represented by Chemical Formula 10,
in the Chemical Formulae 8 to 10,
R22 to R32 are each independently any one functional group selected from hydrogen; deuterium; a halogen group; an alkyl group having 1 to 20 carbon atoms; an alkoxy group having 1 to 20 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an alkenyl group having 2 to 20 carbon atoms; and a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, and
L6 is a direct bond, an alkylene group having 1 to 20 carbon atoms, or an oxyalkylene groups having 1 to 20 carbon atoms.

### Claim 15 (depends on 1)

A photosensitive resin composition comprising:
the alkali soluble, photo-curable and thermo-curable copolymer of claim 1;
a photopolymerizable monomer having two or more photocurable unsaturated functional groups; and
a photo-initiator.

### Claim 16 (depends on 15)

The photosensitive resin composition according to claim 15, further comprising a pigment.

### Claim 17 (depends on 15)

A photosensitive resin film comprising a cured product of the photosensitive resin composition of claim 15.

### Claim 18 (depends on 17)

A color filter comprising the photosensitive resin film of claim 17.