Leveling agent, resist composition and polarizing plate

Abstract

Provided is a leveling agent capable of imparting high smoothness to a coating film. A leveling agent which is a silicone chain-containing polymer having, as polymerization components, at least a polymerizable monomer (a1) having a structure represented by general formula (A) (x represents the number of repetitions, and the number mean value is 20 or more) and a polymerizable monomer (a2). The polymerizable monomer (a1) has at least one group selected from the group consisting of an alkyl group having 1-18 carbon atoms, an aromatic group having 6-18 carbon atoms, a group containing a polyoxyalkylene chain, and a group containing a polyester chain, and the proportion of the polymerizable monomer (a1) in the polymerizable component is more than 20 mass%.

Description

Technical Field

[0001] This invention relates to leveling agents, resist compositions, and polarizing plates. Background Technology

[0002] Leveling agents are added, for example, to smooth the coating obtained by coating a resist composition. Leveling agents have a variety of uses; for example, they can be used in the color resist composition used in the manufacture of color filters for liquid crystal displays. The manufacture of color filters typically includes the following steps: coating a color resist composition onto a glass substrate using coating methods such as spin coating or slot coating; exposing the dried coating using a mask; and then developing it to form a colored pattern. During this process, if the coating smoothness is poor, resulting in uneven film thickness, uneven coating, pinholes, etc., uneven pixel color may occur. By adding a leveling agent to the color resist composition, the smoothness of the resulting coating is improved, and the surfaces of the red (R), green (G), and blue (B) pixels and the black matrix (BM) formed between these pixels exhibit high smoothness, enabling the manufacture of color filters with less color unevenness.

[0003] Fluorinated leveling agents have been used to date, but due to the suspected environmental accumulation of fluorinated compounds, there is an urgent need for non-fluorinated leveling agents as alternatives. Organosilicon compounds have been proposed as non-fluorinated leveling agents (e.g., Patent Document 1).

[0004] Existing technical documents

[0005] Patent documents

[0006] Patent Document 1: Japanese Patent Application Publication No. 2002-179991 Summary of the Invention

[0007] The problem the invention aims to solve

[0008] The problem to be solved by the present invention is to provide a leveling agent that can impart high smoothness to a coating film, and a photoresist composition and a polarizing plate containing the leveling agent that can form a coating film with excellent smoothness.

[0009] Solution for solving the problem

[0010] That is, the present invention relates to leveling agents, etc.

[0011] 1. A leveling agent comprising a polymer containing an organosilicon chain, wherein at least a polymerizable monomer (a1) and a polymerizable monomer (a2) are polymerizable components, said polymerizable monomer (a1) having a group comprising a structure shown in general formula (A), and said polymerizable monomer (a2) having one or more groups selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aromatic group having 6 to 18 carbon atoms, a group comprising a polyoxyalkylene chain, and a group comprising a polyester chain.

[0012] The polymerizable monomer (a1) accounts for more than 20% by mass of the polymeric component.

[0013]

[0014] (In the aforementioned formula (A),

[0015] R 11 Each is an alkyl group having 1 to 6 carbon atoms.

[0016] x represents the number of repetitions, with a mean of 20 or higher.

[0017] 2. The leveling agent according to 1, wherein the group comprising the structure shown in general formula (A) is the group shown in general formula (A1).

[0018]

[0019] (In the aforementioned formula (A1),

[0020] R 11 Each is an alkyl group having 1 to 6 carbon atoms.

[0021] R 12 Each is an alkyl group having 1 to 6 carbon atoms.

[0022] R 13 It is an alkyl group having 1 to 6 carbon atoms.

[0023] x represents the number of repetitions, with a mean of 20 or higher.

[0024] 3. The leveling agent according to 1 or 2, wherein the polymerizable monomer (a1) is a compound represented by the following general formula (a1-1).

[0025]

[0026] (In the general formula (a1-1),

[0027] R 11 Each is an alkyl group having 1 to 6 carbon atoms.

[0028] R 12Each is an alkyl group having 1 to 6 carbon atoms.

[0029] R 13 It is an alkyl group having 1 to 6 carbon atoms.

[0030] x represents the number of repetitions, with a mean of 20 or higher.

[0031] R 15 It can be a hydrogen atom or a methyl group.

[0032] L 1 (It is a divalent organic group.)

[0033] 4. The leveling agent according to any one of 1 to 3, wherein the polymeric monomer (a2) comprises a polymeric monomer having a group containing a polyoxyalkylene chain.

[0034] 5. The leveling agent according to any one of 1 to 4, wherein the polymerizable monomer (a2) is one or more selected from the group consisting of the compound represented by the following general formula (a2-1), the compound represented by the following general formula (a2-2), the compound represented by the following general formula (a2-3), and the compound represented by the following general formula (a2-4).

[0035]

[0036] (In the general formulas (a2-1), (a2-2), (a2-3), and (a2-4),

[0037] R 21 It can be a hydrogen atom or a methyl group.

[0038] R 22 Alkyl groups having 1 to 18 carbon atoms

[0039] R 23 It can be a hydrogen atom or a methyl group.

[0040] R 24 It is an alkyl group having 1 to 18 hydrogen atoms or carbon atoms.

[0041] R 25 It can be a hydrogen atom or a methyl group.

[0042] R 26 It is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 18 carbon atoms and an ether bond.

[0043] R 27 It can be a hydrogen atom or a methyl group.

[0044] R 28 It is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 18 carbon atoms and an ether bond.

[0045] L 2 It is a divalent organic group or a single bond.

[0046] n is an integer in the range of 1 to 4, m represents the number of repetitions, and the average value of m is in the range of 1 to 200; p is an integer in the range of 1 to 10; q represents the number of repetitions, and the average value of q is in the range of 1 to 100.

[0047] 6. The leveling agent according to any one of 1 to 5, wherein the polymeric monomer (a1) accounts for a proportion of 25 to 50% by mass in the polymeric component.

[0048] 7. The leveling agent according to any one of 1 to 6, wherein 80% by mass of the polymeric component is the polymeric monomer (a1) and the polymeric monomer (a2).

[0049] 8. The leveling agent according to any one of 1 to 7, wherein the polymer containing the organosilicon chain is free of fluorine atoms.

[0050] 9. The leveling agent according to any one of 1 to 8, wherein the weight-average molecular weight of the polymer containing the organosilicon chain is 15,000 or more.

[0051] 10. A resist composition comprising any one of 1 to 9.

[0052] 11. A polarizing plate comprising any one of the leveling agents described in 1 to 9.

[0053] The effects of the invention

[0054] According to the present invention, a leveling agent capable of imparting high smoothness to a coating film, and a resist composition comprising the leveling agent capable of forming a coating film with excellent smoothness and a polarizing plate may be provided. Detailed Implementation

[0055] The following describes one embodiment of the present invention. The present invention is not limited to this embodiment, and can be implemented with appropriate modifications without impairing its effects.

[0056] In this application specification, "(meth)acrylic acid" means one or both of acrylic acid and methacrylic acid.

[0057] Leveling agent

[0058] The leveling agent of the present invention is a polymer containing an organosilicon chain, wherein at least a polymeric monomer (a1) and a polymeric monomer (a2) are polymeric components, wherein the polymeric monomer (a1) has a group comprising the structure shown in the following general formula (A), and the polymeric monomer (a2) has one or more groups selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aromatic group having 6 to 18 carbon atoms, a group comprising a polyoxyalkylene chain, and a group comprising a polyester chain, wherein the polymeric monomer (a1) accounts for more than 20% by mass of the polymeric component.

[0059]

[0060] (In the aforementioned formula (A),

[0061] R 11 Each is an alkyl group having 1 to 6 carbon atoms.

[0062] x represents the number of repetitions, with a mean of 20 or higher.

[0063] In this invention, "polymerizable monomer" refers to a compound having a polymerizable unsaturated group. Examples of polymerizable unsaturated groups in polymerizable monomers (a1) and (a2) include (meth)acryloyl, (meth)acryloyloxy, (meth)acrylamide, vinyl ether, allyl, styrene, and maleimide groups, which contain C=C. Among these, (meth)acryloyl and (meth)acryloyloxy are preferred from the perspectives of ease of obtaining raw materials and good polymerization reactivity.

[0064] In addition, the number of polymerizable unsaturated groups in a polymerizable monomer can be one or more.

[0065] In this invention, "polymerizable monomer" refers to a compound having a polymerizable unsaturated group. Examples of polymerizable unsaturated groups in polymerizable monomers (a1) and (a2) include (meth)acryloyl, (meth)acryloyloxy, (meth)acrylamide, vinyl ether, allyl, styrene, and maleimide groups, which contain C=C. Among these, (meth)acryloyl and (meth)acryloyloxy are preferred from the perspectives of ease of obtaining raw materials and good polymerization reactivity.

[0066] A polymerizable monomer may have one or more polymerizable unsaturated groups.

[0067] In this invention, "polymerization component" refers to the component that constitutes the polymer, excluding solvents, polymerization initiators, etc., that do not constitute the polymer.

[0068] The group comprising the structure shown in general formula (A) is preferably the group shown in general formula (A1) below.

[0069]

[0070] (In the aforementioned formula (A1),

[0071] R 11 Each is an alkyl group having 1 to 6 carbon atoms.

[0072] R 12 Each is an alkyl group having 1 to 6 carbon atoms.

[0073] R 13 It is an alkyl group having 1 to 6 carbon atoms.

[0074] x represents the number of repetitions, with a mean of 20 or higher.

[0075] In the general formulas (A) and (A1), R 11 R 12 and R 13 Methyl is preferred.

[0076] In the general formulas (A) and (A1), the average value of x in the polymer of the present invention is 20 or more, preferably in the range of 30 to 300, more preferably in the range of 40 to 200, even more preferably in the range of 50 to 150, and even more preferably in the range of 50 to 80.

[0077] It should be noted that, in this invention, "the numerical mean of x" refers to the average number of repeating units of the siloxane bond in each polymerizable monomer (a1) constituting the polymer of this invention.

[0078] The number mean value of x in the polymer of the present invention can be calculated from the number mean molecular weight of the polymer of the present invention.

[0079] The polymerizable monomer (a1) is preferably a compound represented by the following general formula (a1-1).

[0080]

[0081] (In the general formula (a1-1),

[0082] R 11 R 12 R 13 And x are respectively related to R of the general formulas (A) and (A1). 11 R 12 R 13 Same as x

[0083] R 15It can be a hydrogen atom or a methyl group.

[0084] L 1 (It is a divalent organic group.)

[0085] L 1 The divalent organic group is preferably a single bond, an alkylene group with 1 to 50 carbon atoms, or an alkylene oxide group with 1 to 50 carbon atoms.

[0086] As L 1 Alkylenes with 1 to 50 carbon atoms include methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene, n-octylene, n-nonylene, n-decylene, n-dodecylene, isopropylene, 2-methylpropylene, 2-methylhexylene, tetramethylethylene, etc.

[0087] L 1 The alkylene group having 1 to 50 carbon atoms is preferably an alkylene group having 1 to 15 carbon atoms, more preferably an alkylene group having 1 to 5 carbon atoms, and even more preferably methylene, ethylene, n-propylene, or isopropylene.

[0088] L 1 An alkylene oxide with 1 to 50 carbon atoms is, for example, a group in the alkylene oxide formed by replacing -CH2- with -O-.

[0089] L 1 The alkylene oxide with 1 to 50 carbon atoms is preferably an alkylene oxide with 1 to 15 carbon atoms, more preferably an alkylene oxide with 1 to 8 carbon atoms, and even more preferably a methylene oxide, ethylene oxide, propylene oxide, oxytrimethylene, butylene oxide, oxytetramethylene, pentylene oxide, heptylene oxide, or octylene oxide.

[0090] In L 1 When the divalent organic group is an alkylene group with 1 to 50 carbon atoms or an alkylene oxide group with 1 to 50 carbon atoms, part of the -CH2- of these divalent organic groups can be replaced by a carbonyl group (-C(=O)-), a phenylene group, an amide bond, or a carbamate bond, and a hydroxyl group can also be substituted on the carbon atom.

[0091] Polymerizable monomers (a1) can be manufactured by known methods or commercially available products can be used.

[0092] Specific examples of polymerizable monomers (a1) include α-(3-methacryloyloxy)propyl polydimethylsiloxane and 3-(methacryloyloxy)propyl tris(trimethylsiloxy)silane.

[0093] The polymerizable monomer (a2) is one or more polymerizable monomers selected from the group consisting of alkyl groups having 1 to 18 carbon atoms, aromatic groups having 6 to 18 carbon atoms, groups containing polyoxyalkylene chains, and groups containing polyester chains.

[0094] The polymerizable monomer (a2) may have an alkyl group having 1 to 18 carbon atoms, which may be any of straight-chain alkyl, branched alkyl, and cyclic alkyl. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-hexyl, cyclohexyl, n-octyl, hexadecyl, etc.

[0095] The alkyl group having 1 to 18 carbon atoms in the polymerizable monomer (a2) is preferably an alkyl group having 1 to 6 carbon atoms.

[0096] Examples of aromatic groups with 6 to 18 carbon atoms in polymerizable monomers (a2) include phenyl, naphthyl, anthracene-1-yl, phenanthrene-1-yl, etc.

[0097] The groups containing (poly)oxoalkylene chains in polymerizable monomers (a2) refer to monovalent groups containing repeating portions of oxoalkylene or divalent linking groups containing repeating portions of oxoalkylene.

[0098] The polymerizable monomer (a2) contains groups that include polyester chains, which are either monovalent groups containing repeating portions of ester bonds or divalent linking groups containing repeating portions of ester bonds.

[0099] Examples of polymerizable monomers (a2) that are alkyl groups having 1 to 18 carbon atoms and whose polymerizable unsaturated group is (meth)acryloyl group include, for example, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, n-pentyl methacrylate, n-hexyl methacrylate, n-heptyl methacrylate, n-octyl methacrylate, and 2-ethyl methacrylate. Alkyl esters of (meth)acrylic acid with 1 to 18 carbon atoms, such as hexyl ester, decyl ester, dodecyl ester, stearyl ester, and isostearyl ester; and bridged cyclic alkyl esters of (meth)acrylic acid with 1 to 18 carbon atoms, such as dicyclopentoxyethyl ester, isobornyloxyethyl ester, isobornyl ester, adamantane ester, dimethyladamantane ester, dicyclopentyl ester, and dicyclopentenyl ester.

[0100] Examples of polymerizable monomers (a2) that are phenylalkyl or phenoxyalkyl groups having 7 to 18 carbon atoms and whose polymerizable unsaturated group is (meth)acryloyl group include benzyl (meth)acrylate, phenoxymethyl (meth)acrylate, and 2-phenoxyethyl (meth)acrylate.

[0101] Examples of polymerizable monomers (a2) that are alkyl groups having 1 to 18 carbon atoms and whose polymerizable unsaturated group is a vinyl ether group include methyl vinyl ether, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, tert-butyl vinyl ether, n-pentyl vinyl ether, n-hexyl vinyl ether, n-octyl vinyl ether, n-dodecyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexyl vinyl ether, and other alkyl vinyl ethers; cycloalkyl vinyl ethers, etc.

[0102] Examples of polymerizable monomers (a2) having aromatic groups having 6 to 18 carbon atoms include styrene, α-methylstyrene, p-methylstyrene, and p-methoxystyrene.

[0103] Examples of polymerizable monomers (a2) that have an alkyl group having 1 to 18 carbon atoms and a polymerizable unsaturated group of (meth)acrylamide include N,N-dimethylacrylamide, N,N-diethylacrylamide, N-isopropylacrylamide, diacetoneacrylamide, and acryloylmorpholine.

[0104] Examples of polymerizable monomers (a2) that are alkyl groups having 1 to 18 carbon atoms and whose polymerizable unsaturated group is a maleimide group include methyl maleimide, ethyl maleimide, propyl maleimide, butyl maleimide, hexyl maleimide, octyl maleimide, dodecyl maleimide, stearyl maleimide, and cyclohexyl maleimide.

[0105] Examples of polymerizable monomers (a2) that have a group containing a polyoxyalkylene chain and a polymerizable unsaturated group of (meth)acryloyl group include polypropylene glycol mono(meth)acrylate, polyethylene glycol mono(meth)acrylate, polytrimethylene glycol mono(meth)acrylate, polytetramethylene glycol mono(meth)acrylate, poly(ethylene glycol·propylene glycol) mono(meth)acrylate, polyethylene glycol·polypropylene glycol mono(meth)acrylate, poly(ethylene glycol·tetramethylene glycol) mono(meth)acrylate, and poly(ethylene glycol·tetramethylene glycol) mono(meth)acrylate. Poly(propylene glycol) tetramethylene glycol mono(meth)acrylate, poly(propylene glycol) tetramethylene glycol mono(meth)acrylate, poly(propylene glycol) tetramethylene glycol mono(meth)acrylate, poly(propylene glycol) 1,2-butanediol mono(meth)acrylate, poly(propylene glycol) poly(1,2-butanediol) mono(meth)acrylate, poly(ethylene glycol) 1,2-butanediol mono(meth)acrylate, poly(ethylene glycol) poly(1,2-butanediol) mono(meth)acrylate, poly(tetraethylene glycol) 1,2-butanediol mono(meth)acrylate 1,2-Butanediol mono(meth)acrylate, poly(ethylene glycol·poly(1,2-butanediol)meth)acrylate, poly(ethylene glycol·trimethylenediol)mono(meth)acrylate, poly(ethylene glycol·polytrimethylenediol)mono(meth)acrylate, poly(propylene glycol·trimethylenediol)mono(meth)acrylate, poly(propylene glycol·polytrimethylenediol)mono(meth)acrylate, poly(trimethylenediol·tetramethylenediol)mono(meth)acrylate, polytrimethylenediol·poly(trimethylenediol)mono(meth)acrylate Methyl glycol mono(meth)acrylate, poly(1,2-butanediol·trimethylenediol) mono(meth)acrylate, poly(1,2-butanediol·polytrimethylenediol) mono(meth)acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, poly(1,2-butanediol·tetramethylenediol) mono(meth)acrylate, poly(1,2-butanediol·tetramethylenediol) mono(meth)acrylate, etc.

[0106] It should be noted that "poly(ethylene glycol·propylene glycol)" refers to a random copolymer of ethylene glycol and propylene glycol, and "polyethylene glycol·polypropylene glycol" refers to a block copolymer of ethylene glycol and propylene glycol.

[0107] The polymerizable monomer (a2) is preferably one or more selected from the group consisting of compounds represented by general formula (a2-1), general formula (a2-2), general formula (a2-3), general formula (a2-4), and general formula (a2-5), and more preferably one or more selected from the group consisting of compounds represented by general formula (a2-1), general formula (a2-2), general formula (a2-3), and general formula (a2-4).

[0108]

[0109] (In the general formulas (a2-1), (a2-2), (a2-3), (a2-4), and (a2-5),

[0110] R 21 It can be a hydrogen atom or a methyl group.

[0111] R 22 Alkyl groups having 1 to 18 carbon atoms

[0112] R 23 It can be a hydrogen atom or a methyl group.

[0113] R 24 It is an alkyl group having 1 to 18 hydrogen atoms or carbon atoms.

[0114] R 25 It can be a hydrogen atom or a methyl group.

[0115] R 26 It is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 18 carbon atoms and an ether bond.

[0116] R 27 It can be a hydrogen atom or a methyl group.

[0117] R 28 It is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 18 carbon atoms and an ether bond.

[0118] L 2 It is a divalent organic group or a single bond.

[0119] R 29 It can be a hydrogen atom or a methyl group.

[0120] R 30 Each is independently an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms.

[0121] n is an integer in the range of 1 to 4, m represents the number of repetitions, with the mean of m ranging from 1 to 200, p is an integer in the range of 1 to 10, q represents the number of repetitions, with the mean of q ranging from 1 to 100, and l is an integer in the range of 0 to 5.

[0122] In the general formula (a2-2), the m n's within the parentheses can be the same or different from each other.

[0123] In the general formula (a2-3), the q p's within the parentheses can be the same or different from each other.

[0124] In the general formula (a2-4), the q p's within the parentheses can be the same or different from each other.

[0125] The L in the general formulas (a2-3) and (a2-4) 2 divalent organic groups can be listed as those related to L 1 The same group as the divalent organic group.

[0126] The polymerizable monomer (a2) preferably comprises a polymerizable monomer having a group containing a polyoxyalkylene chain, and more preferably comprises a compound represented by the general formula (a2-2).

[0127] As a polymerizable monomer (a2), when a polymerizable monomer contains a group having a polyoxyalkylene chain, high compatibility with the matrix resin can be expected.

[0128] The polymerizable monomer (a2) preferably comprises one or more compounds selected from the group consisting of the compounds represented by the general formula (a2-2), the compounds represented by the general formula (a2-3), and the compounds represented by the general formula (a2-4).

[0129] When the polymerizable monomer (a2) comprises one or more compounds selected from the group consisting of the compound represented by the general formula (a2-2), the compound represented by the general formula (a2-3), and the compound represented by the general formula (a2-4), the total amount of the compound represented by the general formula (a2-2), the compound represented by the general formula (a2-3), and the compound represented by the general formula (a2-4) is preferably 50% by mass or more relative to the total amount of the polymerizable monomer (a2).

[0130] Polymerizable monomer (a2) can be manufactured by known methods.

[0131] Alternatively, commercially available polymerizable monomers (a2) can also be used. For example, commercially available products (a2) that are polymerizable monomers (a2) having a group containing a polyoxyalkylene chain and a polymerizable unsaturated group of (meth)acryloyl group include "NK ESTER M-20G", "NK ESTER M-40G", "NK ESTER M-90G", "NK ESTER M-230G", "NK ESTER AM-90G", "NK ESTER AMP-10G", "NK ESTER AMP-20G", and "NK ESTER AMP-60G" manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and "BLEMMER PE-90", "BLEMMER PE-200", "BLEMMER PE-350", "BLEMMER PME-100", "BLEMMER PME-200", "BLEMMER PME-400", "BLEMMER PME-4000", "BLEMMER PP-1000", "BLEMMER PP-500", and "BLEMMER PME-200", "BLEMMER PME-4000", "BLEMMER PME-4000", "BLEMMER PP-1000", and "BLEMMER PP-500". Products include: PP-800, BLEMMER 70PEP-350B, BLEMMER 55PET-800, BLEMMER 50POEP-800B, BLEMMER 10PPB-500B, BLEMMER NKH-5050, BLEMMER AP-400, BLEMMER AE-350, PLACEL F series manufactured by Daicel Corporation, and VISCOAT series manufactured by Osaka Organic Chemical Industry Co., Ltd.

[0132] The proportion of polymerizable monomer (a1) in the polymerizing component (polymerizable monomer (a1) / total amount of polymerizing component) only needs to be greater than 20% by mass, preferably 22% by mass or more, and more preferably 25% by mass or more. By keeping the proportion of polymerizable monomer (a1) in the polymerizing component within this range, excellent leveling properties can be obtained.

[0133] There is no particular limit to the upper limit of the proportion of polymerizable monomer (a1) in the polymeric component, for example, it is 90% by mass or less, preferably 70% by mass or less, more preferably 50% by mass or less, further preferably 40% by mass or less, and even more preferably less than 35% by mass.

[0134] The proportion of polymerizable monomer (a1) can be adjusted by the ratio of raw materials input of polymerizable monomer (a1) when manufacturing the polymer of the present invention.

[0135] The mass ratio of polymerizable monomer (a1) to polymerizable monomer (a2) in the polymeric component is, for example, polymerizable monomer (a1): polymerizable monomer (a2) = 21:79~80:20, preferably 22:78~60:40, and more preferably 25:75~50:50.

[0136] The proportion of the groups represented by the general formula (A) in the polymer of the present invention (the total mass of the groups represented by formula (A) / the mass of the polymer containing the organosilicon chain) is, for example, 21 to 80% by mass, preferably 22 to 60% by mass, more preferably 25 to 50% by mass, and even more preferably 25 to 40% by mass.

[0137] The proportion of the groups represented by the general formula (A) can be adjusted by the ratio of the raw material input of the polymeric monomer (a1) used in manufacturing the polymer of the present invention.

[0138] In addition to polymerizable monomers (a1) and (a2), the polymerizable component preferably includes polymerizable monomer (a3) ​​as a compound represented by the following general formula (a3-1). By imparting hydrophilicity to the leveling agent, it is possible to improve developability, recoatability, etc. when preparing a photoresist composition, and furthermore, it is possible to improve recoatability when used in a polarizing plate.

[0139]

[0140] (In the general formula (a3-1),

[0141] R 31 It can be a hydrogen atom or a methyl group.

[0142] R 32 It is a hydroxyalkyl group having 1 to 18 hydrogen atoms or carbon atoms.

[0143] In the general formula (a3-1), the hydroxyalkyl group having 1 to 18 carbon atoms is a group in which a hydroxyl group is substituted on an alkyl group having 1 to 18 carbon atoms.

[0144] The alkyl group having 1 to 18 carbon atoms can be any of the straight-chain alkyl, branched alkyl, and cyclic alkyl groups. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-hexyl, cyclohexyl, n-octyl, hexadecyl, etc.

[0145] The hydroxyalkyl group having 1 to 18 carbon atoms is preferably a hydroxyalkyl group having 1 to 6 carbon atoms.

[0146] When the polymeric monomer (a3) ​​is included as a polymerizing component, the polymeric monomer (a3) ​​in the polymer of the present invention is contained in a proportion of, for example, 1 to 50% by mass of the total amount of polymerizing component, preferably 1 to 20% by mass, more preferably 5 to 20% by mass, and even more preferably 5 to 15% by mass.

[0147] The polymer containing organosilicon chains that serves as the leveling agent of the present invention (hereinafter, sometimes simply referred to as "the polymer of the present invention") can be any polymer in which polymerizable monomers (a1), polymerizable monomers (a2) and any polymerizable monomer (a3) ​​are polymeric components, and its polymerization form is not particularly limited.

[0148] The polymer of the present invention can be a random copolymer of polymeric monomer (a1), polymeric monomer (a2) and any polymeric monomer (a3), or a block copolymer of polymeric monomer (a1), polymeric monomer (a2) and any polymeric monomer (a3), preferably a block copolymer of polymeric monomer (a1), polymeric monomer (a2) and any polymeric monomer (a3).

[0149] For example, in the case where the polymer of the present invention is a block copolymer of polymeric monomer (a1) and polymeric monomer (a2), the number and bonding order of the polymeric blocks of polymeric monomer (a1) and polymeric monomer (a2) are not particularly limited. For example, it can be a diblock copolymer formed by bonding the polymeric blocks of polymeric monomer (a1) and polymeric blocks of polymeric monomer (a2).

[0150] In the polymer component, the polymerizable monomer (a1) can be a single polymerizable monomer (a1) or two or more polymerizable monomers (a1) with different structures.

[0151] Similarly, in the polymeric component, the polymeric monomer (a2) can be a single polymeric monomer (a2) or two or more polymeric monomers (a2) with different structures.

[0152] Similarly, in the polymeric component, the polymeric monomer (a3) ​​can be a single polymeric monomer (a3) ​​or two or more polymeric monomers (a3) ​​with different structures.

[0153] The polymeric component only needs to contain polymeric monomers (a1), polymeric monomers (a2), and any polymeric monomers (a3). It can be substantially formed by polymeric monomers (a1), polymeric monomers (a2), and any polymeric monomers (a3), or it can be formed solely by polymeric monomers (a1), polymeric monomers (a2), and any polymeric monomers (a3).

[0154] Here, "substantially formed" means that the total content of the polymeric monomer (a1), polymeric monomer (a2), and any polymeric monomer (a3) ​​in the polymeric component is, for example, 85% by mass or more, 90% by mass or more, 95% by mass or more, or 98% by mass or more.

[0155] Polymer components include (meth)acrylates that do not contain alkyl monohydric alcohols and / or (meth)acrylates that do not contain cycloalkyl monohydric alcohols.

[0156] It should be noted that the alkyl monohydric alcohol has, for example, 1 to 22 carbon atoms, and the cycloalkyl monohydric alcohol has, for example, 3 to 22 carbon atoms.

[0157] The polymers of the present invention are preferably free of fluorine atoms. By being fluorine-free polymers, their environmental accumulation is reduced, thereby decreasing the environmental burden.

[0158] The polymers of the present invention preferably do not contain reactive functional groups.

[0159] In this invention, "reactive functional group" refers to a functional group that can react with other functional groups to form cross-linked structures, etc. Examples include isocyanate group, epoxy group, carboxyl group, carboxyl halogen group, carboxylic anhydride group, etc.

[0160] The weight-average molecular weight (Mw) of the polymer of the present invention is, for example, 10,000 or more, preferably 15,000 or more, more preferably 18,000 or more, and even more preferably 20,000 or more.

[0161] The upper limit of the weight-average molecular weight (Mw) of the polymer of the present invention is not particularly limited, but is preferably 100,000 or less, 90,000 or less, 70,000 or less, and 50,000 or less, respectively.

[0162] The weight-average molecular weight (Mw) of the polymers of the present invention was determined by the method described in the examples.

[0163] [Method for manufacturing polymers containing organosilicon chains]

[0164] The manufacturing method of the polymer of the present invention is not particularly limited and can be manufactured by known methods.

[0165] The polymers of this invention can be manufactured using polymerization mechanisms such as free radical polymerization, cationic polymerization, and anionic polymerization, through methods such as solution polymerization, bulk polymerization, and emulsion polymerization. For example, in the case of free radical polymerization, the polymers of this invention can be manufactured by adding the polymerizing components to an organic solvent and adding a common free radical polymerization initiator.

[0166] The polymer obtained above is a random copolymer.

[0167] Various polymerization initiators can be used as polymerization initiators, such as peroxides like tert-butyl peroxide-2-ethylhexanoate, benzoyl peroxide, and diacyl peroxide; azo compounds like azobisisobutyronitrile, dimethyl azobisisobutyrate, and phenylazotriphenylmethane; and metal chelates like Mn(acac)3.

[0168] Depending on the requirements, chain transfer agents such as lauryl thiol, 2-mercaptoethanol, ethyl mercaptoacetate, and octyl mercaptoacetate, as well as thiol compounds with coupling groups such as γ-mercaptopropyltrimethoxysilane, can also be used as chain transfer agents and other additives.

[0169] Examples of organic solvents include, for example, alcohols such as ethanol, isopropanol, n-butanol, isobutanol, and tert-butanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and methyl pentyl ketone; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, and butyl lactate; and monocarboxylic acid esters such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, propyl 2-hydroxypropionate, butyl 2-hydroxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, and butyl 2-methoxypropionate. Polar solvents such as methylformamide, dimethyl sulfoxide, and N-methylpyrrolidone; ethers such as methyl cellosolve, cellosolve, butyl cellosolve, butyl carbitol, and ethyl cellosolve acetate; propylene glycols and their esters such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and propylene glycol monobutyl ether acetate; halogen solvents such as 1,1,1-trichloroethane and chloroform; ethers such as tetrahydrofuran and dioxane; aromatics such as benzene, toluene, and xylene; and fluorinated inert liquids such as perfluorooctane and perfluorotri-n-butylamine.

[0170] These solvents can be used alone or in combination of two or more.

[0171] The polymer of the present invention preferably begins with the addition of a polymerizable monomer (a1) in the reaction system. After the addition of the polymerizable monomer (a1) begins, a polymerizable monomer (a2) and a polymerization initiator are added to the reaction system to initiate polymerization. The addition of the polymerizable monomer (a1) ends before the addition of the polymerizable monomer (a2) and the polymerization initiator.

[0172] This is because, by polymerizing the polymer of the present invention in this way, unreacted silicone chains can be minimized, thereby suppressing coating defects that are a concern due to additives during coating.

[0173] The polymerizable monomer (a1) sometimes contains impurities of compounds with cyclic siloxane structures. It is advisable to remove compounds with cyclic siloxane structures by distilling the polymerizable monomer (a1) before adding it to the reaction system, or by distilling the polymer after the reaction. Distillation can be carried out by known methods, such as thin-film distillation.

[0174] The polymer of the present invention can also be manufactured by subjecting the polymer components to living polymerization, such as living free radical polymerization or living anionic polymerization.

[0175] In the described living radical polymerization, dormant species protected by atoms or groups at the active polymerization end reversibly generate free radicals, which react with monomers to carry out a growth reaction. Even if the first monomer is consumed, the growth end does not lose its activity and can react with successively added second monomers to obtain a block polymer. Examples of such living radical polymerization include atom transfer radical polymerization (ATRP), reversible addition-fragmentation radical polymerization (RAFT), radical polymerization via nitroxide compounds (NMP), and radical polymerization using organotelluric acid (TERP). There are no particular restrictions on the method used, but ATRP is preferred for ease of control. ATRP uses organohalides or sulfonyl halides as polymerization initiators and metal complexes formed from transition metal compounds and ligands as catalysts for polymerization.

[0176] Specific examples of polymerization initiators that can be used in ATRP include (1-chloroethyl)benzene, (1-bromoethyl)benzene, chloroform, carbon tetrachloride, 2-chloropropionitrile, α,α'-dichloroxylene, α,α'-dibromoxylene, hexa(α-bromomethyl)benzene, and alkyl esters of 2-halocarboxylic acids (e.g., 2-chloropropionic acid, 2-bromopropionic acid, 2-chloroisobutyric acid, 2-bromoisobutyric acid, etc.) with 1 to 6 carbon atoms.

[0177] More specific examples of alkyl esters of 2-halocarboxylic acids having 1 to 6 carbon atoms include methyl 2-chloropropionate, ethyl 2-chloropropionate, methyl 2-bromopropionate, and ethyl 2-bromoisobutyrate.

[0178] The transition metal compounds that can be used in ATRP are from M n+ X n express.

[0179] As a result of M n+ X n The transition metal M represented by the transition metal compound n+ You can choose free Cu + Cu 2+ Fe 2+ Fe 3+ Ru 2+ Ru 3+ Cr 2+ Cr 3+ Mo 0 Mo + Mo 2+ Mo 3+ W 2+ W 3+ ,Rh 3+ ,Rh 4+ Co + Co 2+ Re 2+ Re 3+ Ni 0 Ni + Mn 3 + Mn 4+ V 2+ V 3+ Zn + Zn 2+ Au + Au 2+ Ag + and Ag 2+ A group that is formed.

[0180] By M n+ X n The X in the transition metal compound can be chosen from a halogen atom, an alkoxy group with 1 to 6 carbon atoms, or (SO4). 1 / 2 (PO4) 1 / 3 (HPO4) 1 / 2 (H2PO4), trifluoromethanesulfonate, hexafluorophosphate, methanesulfonate, arylsulfonate (preferably benzenesulfonate or toluenesulfonate), SeR 11 CN and R 12 A group consisting of COO. Here, R 11 R represents an aryl, linear, or branched alkyl group with 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms). 12 The alkyl group (preferably methyl) is a straight-chain or branched alkyl group with 1 to 6 carbon atoms that can be substituted 1 to 5 times with halogens (preferably substituted 1 to 3 times with fluorine or chlorine) and can be represented by a hydrogen atom.

[0181] By M n+ X n The 'n' in the transition metal compound represents the formal charge on the metal, and is an integer from 0 to 7.

[0182] Examples of ligand compounds capable of coordinating with the transition metal of the aforementioned transition metal compound include compounds having ligands containing one or more nitrogen, oxygen, phosphorus, or sulfur atoms that can coordinate with the transition metal via σ bonds, compounds having ligands containing two or more carbon atoms that can coordinate with the transition metal via π bonds, and compounds having ligands that can coordinate with the transition metal via μ or η bonds.

[0183] There are no particular limitations on the transition metal complexes mentioned above. Preferred complexes include transition metal complexes from groups 7, 8, 9, 10, and 11. Further preferred complexes include complexes of copper with a valence of 0, copper with a valence of 1, ruthenium with a valence of 2, iron with a valence of 2, or nickel with a valence of 2.

[0184] Specific examples of catalysts that can be used in ATRP, when the central metal is copper, include complexes with ligands such as 2,2'-bipyridine and its derivatives, 1,10-phenanthroline and its derivatives, tetramethylethylenediamine, pentamethyldiethylenetriamine, and hexamethyltris(2-aminoethyl)amine. Additionally, divalent ruthenium complexes include ruthenium trichlorotris(triphenylphosphine)ruthenium, ruthenium trichlorotris(tributylphosphine)ruthenium, ruthenium trichloro(cyclooctadiene)ruthenium, ruthenium dichlorobenzene, ruthenium dichloro-p-methylisopropylbenzene, ruthenium dichloro(norbornene)ruthenium, cis-dichlorobis(2,2'-bipyridine)ruthenium, ruthenium trichlorotris(1,10-phenanthroline)ruthenium, and ruthenium trichlorohydrocarbonyl(triphenylphosphine)ruthenium. Furthermore, divalent iron complexes include bis(triphenylphosphine) complexes and triazacyclononane complexes.

[0185] In living radical polymerization, solvents are preferred.

[0186] Examples of solvents used in living radical polymerization include ester solvents such as ethyl acetate, butyl acetate, and propylene glycol monomethyl ether acetate; ether solvents such as diisopropyl ether, dimethoxyethane, and diethylene glycol dimethyl ether; halogen solvents such as dichloromethane and dichloroethane; aromatic solvents such as toluene and xylene; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; alcohol solvents such as methanol, ethanol, and isopropanol; and aprotic polar solvents such as dimethylformamide and dimethyl sulfoxide.

[0187] The solvent can be used alone or in combination of two or more.

[0188] In the case of manufacturing the polymer of the present invention by living polymerization, it can be manufactured, for example, by any of the methods 1 to 3 shown below.

[0189] Method 1: A method for carrying out living radical polymerization (preferably atom transfer radical polymerization) of polymerizable monomers (a1) and (a2) in the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of coordinating with the transition metal, and a solvent.

[0190] Method 2: In the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of coordinating with the transition metal, and a solvent, a polymerizable monomer (a1) is subjected to living radical polymerization (preferably atom transfer radical polymerization) to obtain a polymer block of polymerizable monomer (a1). Then, a polymerizable monomer (a2) is added to the reaction system, and the polymerizable monomer (a2) is further subjected to living radical polymerization (preferably atom transfer radical polymerization) on the polymer block of polymerizable monomer (a1).

[0191] Method 3: In the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of coordinating with the transition metal, and a solvent, a polymerizable monomer (a2) is subjected to living radical polymerization (preferably atom transfer radical polymerization) to obtain a polymer block of polymerizable monomer (a2). Then, a polymerizable monomer (a1) is added to the reaction system, and the polymerizable monomer (a1) is further subjected to living radical polymerization (preferably atom transfer radical polymerization) on the polymer block of polymerizable monomer (a2).

[0192] The preferred polymerization temperature for the active free radical polymerization is in the range of room temperature to 120°C.

[0193] When the polymers of the present invention are produced by living radical polymerization, metals originating from the transition metal compounds used in the polymerization may sometimes remain in the resulting polymer. It is preferable to remove the residual metals in the resulting polymer using activated alumina or the like after polymerization.

[0194] [Resistant Composition]

[0195] The leveling agent of the present invention is suitable for use in corrosion resist compositions.

[0196] Photoresist compositions (photoresist compositions, colored photoresist compositions for color filters, etc.) require high leveling properties. Photoresist compositions are typically spin-coated onto silicon wafers or glass substrates deposited with various metals to a thickness of approximately 1-2 μm. If the coating thickness fluctuates or becomes uneven, the linearity and reproducibility of the pattern decrease, resulting in the inability to obtain a resist pattern with the desired precision. In addition to these problems, various leveling-related issues exist, such as drip marks, overall unevenness, and edge thickening (beading) where the film thickness is greater at the edges than at the center.

[0197] The resist composition of the present invention contains the leveling agent of the present invention, which can exhibit high leveling properties to form a uniform coating (cured product), thus solving the problems described above.

[0198] In addition, the leveling agent of the present invention can be made into a fluorine-free leveling agent that does not contain fluorine atoms, and therefore is a leveling agent with low environmental impact and low accumulation.

[0199] The content of the leveling agent of the present invention in the resist composition of the present invention varies depending on the type of base resin, coating method, target film thickness, etc., and is preferably 0.0001 to 10 parts by weight relative to 100 parts by weight of the solid component (e.g., base resin) of the resist composition, more preferably 0.001 to 5 parts by weight, and even more preferably 0.01 to 2 parts by weight. If the content of the leveling agent of the present invention is within this range, the target leveling property can be obtained, and the occurrence of adverse conditions such as bubbling during coating can be suppressed.

[0200] When the photoresist composition of the present invention is made into a photoresist composition, the photoresist composition contains, in addition to the leveling agent of the present invention, an alkali-soluble resin, a radiation-sensitive substance (photosensitive substance), a solvent, etc.

[0201] The alkali-soluble resin contained in the photoresist composition refers to a resin that is soluble in the developing solution, i.e., the alkaline solution, used during the patterning of the photoresist.

[0202] Examples of alkali-soluble resins include: phenolic varnish resins obtained by condensing aromatic hydroxyl compound derivatives such as phenol, cresol, xylenol, resorcinol, phloroglucinol, and hydroquinone with aldehyde compounds such as formaldehyde, acetaldehyde, and benzaldehyde; polymers or copolymers of vinylphenol compound derivatives such as o-vinylphenol, m-vinylphenol, p-vinylphenol, and α-methylvinylphenol; (meth)acrylic acid polymers or copolymers such as acrylic acid, methacrylic acid, and hydroxyethyl (meth)acrylate; polyvinyl alcohol; modified resins in which radiation-sensitive groups such as quinone diazido, naphthoquinone azido, aromatic azido, and aromatic cinnamoyl are introduced into a portion of the hydroxyl groups of these various resins; and urethane resins containing acidic groups such as carboxylic acid and sulfonic acid in their molecules.

[0203] These alkali-soluble resins can be used alone or in combination of two or more.

[0204] The radiation-sensitive substances contained in the photoresist composition refer to substances that change the solubility of alkali-soluble resins in the developer solution when exposed to energy rays such as ultraviolet rays, far ultraviolet rays, excimer lasers, X-rays, electron rays, ion rays, molecular rays, and gamma rays.

[0205] Examples of radiation-sensitive substances include quinone diazide compounds, diazo compounds, azide compounds, onium salt compounds, halogenated organic compounds, mixtures of halogenated organic compounds and organometallic compounds, organic acid ester compounds, organic acid amide compounds, organic acid imide compounds, and poly(olefin sulfone) compounds.

[0206] Examples of quinone diazide compounds include, for example, 1,2-benzoquinone azido-4-sulfonate, 1,2-naphthoquinone diazido-4-sulfonate, 1,2-naphthoquinone diazido-5-sulfonate, 2,1-naphthoquinone diazido-4-sulfonate, 2,1-naphthoquinone diazido-5-sulfonate, and sulfonyl chlorides of quinone diazide derivatives such as 1,2-benzoquinone azido-4-sulfonyl chloride, 1,2-naphthoquinone diazido-4-sulfonyl chloride, 1,2-naphthoquinone diazido-5-sulfonyl chloride, 2,1-naphthoquinone diazido-4-sulfonyl chloride, and 2,1-naphthoquinone diazido-5-sulfonyl chloride.

[0207] Examples of such diazo compounds include: salts of condensates of diazidophenylamine with formaldehyde or acetaldehyde; hexafluorophosphate, tetrafluoroborate, perchlorate or periodate reacting with the condensates to form diazo resin inorganic salts; and diazo resin organic salts reacting with sulfonic acids as described in USP3,300,309.

[0208] Examples of such azide compounds include azidochalcones, diazidobenzylidenemethylcyclohexanones, azidocinnamylacetophenones, aromatic azide compounds, and aromatic diazido compounds.

[0209] Examples of halogenated organic compounds include: halogenated oxadiazole compounds, halogenated triazine compounds, halogenated acetophenone compounds, halogenated benzophenone compounds, halogenated sulfoxide compounds, halogenated sulfone compounds, halogenated thiazole compounds, halogenated oxazole compounds, halogenated triazole compounds, halogenated 2-pyranone compounds, halogenated aliphatic hydrocarbon compounds, halogenated aromatic hydrocarbon compounds, halogenated heterocyclic compounds, and sulfenyl halide compounds.

[0210] In addition to the above, examples of compounds used as halogenated organic compounds include tris(2,3-dibromopropyl) phosphate, tris(2,3-dibromo-3-chloropropyl) phosphate, tetrabromochloromethane, hexachlorobenzene, hexabromobenzene, hexabromocyclododecane, hexabromobiphenyl, tribromophenylallyl ether, tetrachlorobisphenol A, tetrabromobisphenol A, bis(bromoethyl ether)tetrabromobisphenol A, bis(chloroethyl ether)tetrachlorobisphenol A, tris(2,3-dibromopropyl)isocyanurate, 2,2-bis(4-hydroxy-3,5-dibromophenyl)propane, and 2,2-bis(4-hydroxyethoxy-3,5-dibromophenyl)propane, etc., which are used as halogenated flame retardants, and dichlorophenyltrichloroethane, etc., which are used as organochlorine pesticides.

[0211] Examples of organic acid esters include carboxylic acid esters and sulfonate esters. Examples of organic acid amides include carboxylic acid amides and sulfonate amides. Furthermore, examples of organic acid imides include carboxylic acid imides and sulfonate imides.

[0212] Radiation-sensitive substances can be used alone or in combination of two or more.

[0213] In the photoresist composition, the content of the radiation-sensitive substance is preferably in the range of 10 to 200 parts by weight relative to 100 parts by weight of the alkali-soluble resin, and more preferably in the range of 50 to 150 parts by weight.

[0214] Solvents used in photoresist compositions include, for example, ketones such as acetone, methyl ethyl ketone, cyclohexanone, cyclopentanone, cycloheptanone, 2-heptanone, methyl isobutyl ketone, and butyrolactone; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, pentanol, heptanol, octanol, nonanol, and decanol; ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and dioxane; and ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, and ethylene glycol. Alcohol ethers such as monopropyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, and propylene glycol monopropyl ether; esters such as ethyl formate, propyl formate, butyl formate, methyl acetate, ethyl acetate, butyl acetate, propyl acetate, methyl propionate, ethyl propionate, propyl propionate, methyl butyrate, ethyl butyrate, butyl butyrate, propyl butyrate, ethyl lactate, and butyl lactate; methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, and propyl 2-hydroxypropionate. Monocarboxylic acid esters such as butyl 2-hydroxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, and butyl 2-methoxypropionate; cellosol esters such as methyl cellosol ester, ethyl cellosol ester, propyl cellosol ester, and butyl cellosol ester; and propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monobutyl ether. Propylene glycols such as acetates; diethylene glycols such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene glycol methyl ethyl ether; trichloroethylene, Freon solvents, HCFCs, HFCs, and other halogenated hydrocarbons; perfluorinated solvents such as perfluorooctane, toluene, xylene, and other aromatic solvents; polar solvents such as dimethylacetamide, dimethylformamide, N-methylacetamide, and N-methylpyrrolidone.

[0215] These solvents can be used alone or in combination of two or more.

[0216] When the resist composition of the present invention is made into a colored resist composition, the colored resist composition contains, in addition to the leveling agent of the present invention, an alkali-soluble resin, a polymeric compound, a colorant, etc.

[0217] The alkali-soluble resin contained in the color resist can be the same substance as the alkali-soluble resin contained in the photoresist composition.

[0218] The polymerizable compounds contained in the color resist composition refer to, for example, compounds with photopolymerizable functional groups that can undergo polymerization or cross-linking reactions when irradiated by active energy rays such as ultraviolet light.

[0219] Examples of such polymerizable compounds include: unsaturated carboxylic acids such as (meth)acrylic acid; esters of monohydroxy compounds and unsaturated carboxylic acids; esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids; esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids; esters obtained by esterification of unsaturated carboxylic acids with polycarboxylic acids, and polyhydroxy compounds such as aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds; polymerizable compounds having a carbamate skeleton obtained by reacting a polyisocyanate compound with a hydroxy compound containing a (meth)acryloyl group; and polymerizable compounds having acid groups.

[0220] Polymers can be used alone or in combination of two or more.

[0221] Examples of esters of the aforementioned aliphatic polyhydroxy compounds and unsaturated carboxylic acids include ethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, pentaerythritol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, glycerol (meth)acrylate, and other (meth)acrylates.

[0222] Alternatively, examples could be given of acrylates in which the (meth)acrylic acid portion of the acrylate is replaced with itaconic acid, crotonic acid, or maleic acid.

[0223] Examples of esters of the aromatic polyhydroxy compound and the unsaturated carboxylic acid include hydroquinone di(meth)acrylate, resorcinol di(meth)acrylate, and pyrogallol tri(meth)acrylate.

[0224] Esters obtained through the esterification reaction of unsaturated carboxylic acids, polycarboxylic acids, and polyhydroxy compounds can be single substances or mixtures. Examples of such esters include: esters obtained from (meth)acrylic acid, phthalic acid, and ethylene glycol; esters obtained from (meth)acrylic acid, maleic acid, and diethylene glycol; esters obtained from (meth)acrylic acid, terephthalic acid, and pentaerythritol; and esters obtained from (meth)acrylic acid, adipic acid, butanediol, and glycerol.

[0225] Examples of polymerizable compounds with a carbamate skeleton formed by reacting the polyisocyanate compound with a hydroxy compound containing a (meth)acryloyl group include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; alicyclic diisocyanates such as cyclohexane diisocyanate and isophorone diisocyanate; and aromatic diisocyanates such as toluene diisocyanate and diphenylmethane diisocyanate reacting with hydroxy compounds containing a (meth)acryloyl group such as 2-hydroxyethyl methacrylate and 3-hydroxy[1,1,1-tris(meth)acryloyloxymethyl]propane.

[0226] As the polymerizable compound having acid groups, for example, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, it is preferable to obtain a polyfunctional polymerizable compound having acid groups by reacting the unreacted hydroxyl groups of the aliphatic polyhydroxy compound with a non-aromatic carboxylic anhydride. The aliphatic polyhydroxy compound used in the preparation of this polyfunctional polymerizable compound is preferably pentaerythritol or dipentaerythritol.

[0227] From the perspective of improving developability and curability, the acid value of the polyfunctional polymeric compound is preferably in the range of 0.1 to 40, and more preferably in the range of 5 to 30. When using two or more polyfunctional polymeric compounds having acid groups in combination, or when using a combination of polyfunctional polymeric compounds having acid groups and polyfunctional polymeric compounds without acid groups, it is preferable that the acid value of the mixture of polymeric compounds is within the range described above.

[0228] As a specific example of the polymerizable compound having acid groups, a mixture mainly composed of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate and succinate of dipentaerythritol pentaacrylate is provided, which is commercially available in the form of ARONIX TO-1382 (manufactured by Toa Synthetic Co., Ltd.).

[0229] Examples of polymerizable compounds other than those mentioned above include methyl acrylamides such as ethylene bis(meth)acrylamide; allyl esters such as diallyl phthalate; and compounds containing vinyl groups such as divinyl phthalate.

[0230] In the color resist composition, the content of the polymeric compound is preferably in the range of 5 to 80% by mass of the total solids content of the color resist composition, more preferably in the range of 10 to 70% by mass, and even more preferably in the range of 20 to 50% by mass.

[0231] As a colorant in a colored resist composition, it can be anything that can color the material, without any particular limitation. For example, it can be a pigment or a dye.

[0232] The pigment can be either organic or inorganic. As organic pigments, various shades such as red, green, blue, yellow, purple, orange, and brown pigments can be used. Furthermore, examples of the chemical structures of organic pigments include azo, phthalocyanine, quinacridone, benzimidazolone, isoindolinone, dioxazine, indanthrene, and perylene-based pigments. Examples of inorganic pigments include barium sulfate, lead sulfate, titanium dioxide, yellow lead, iron oxide red, and chromium oxide.

[0233] It should be noted that "CI" in the following text refers to the Dye Index.

[0234] Examples of red pigments that can be cited include: CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 5 3:3, 57, 57:1, 57:2, 58:4, 60, 63, 63:1, 63:2, 64, 64:1, 68, 69, 81, 81:1, 81:2, 81:3, 81:4, 83, 88, 90:1, 101, 101:1, 104, 108, 108:1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 23 2, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, etc. Among these, CI Pigment Red 48 is preferred: 1, 122, 168, 177, 202, 206, 207, 209, 224, 242, or 254, and more preferably CI Pigment Red 177, 209, 224, or 254.

[0235] Examples of green pigments include CI pigment green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55, and 58. Among these, CI pigment green 7, 36, or 58 are preferred.

[0236] Examples of blue pigments include CI Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, and 79. Preferably, CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6, and more preferably CI Pigment Blue 15:6.

[0237] Examples of yellow pigments include: CI Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62:1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127:1, 128, 129, 133. 134, 136, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208, etc. The preferred pigments are CI pigment yellow 83, 117, 129, 138, 139, 150, 154, 155, 180 or 185, and more preferably CI pigment yellow 83, 138, 139, 150 or 180.

[0238] Examples of the purple pigments mentioned include CI Pigment Violet 1, 1:1, 2, 2:2, 3, 3:1, 3:3, 5, 5:1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, and 50. Among these, CI Pigment Violet 19 or 23 is preferred, and CI Pigment Violet 23 is more preferred.

[0239] Examples of orange pigments include CI Pigment Orange 1, 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, and 79. Among these, CI Pigment Orange 38 or 71 is preferred.

[0240] The pixels of the color filters used in liquid crystal display devices and organic EL display devices are red (R), green (G), and blue (B). Therefore, the red, green, and blue pigments are the main components. In order to improve color reproduction, organic pigments of colors such as yellow, purple, and orange can also be used for hue adjustment.

[0241] To improve the brightness of color liquid crystal display devices and organic EL display devices, the average particle size of the organic pigment is preferably 1 μm or less, more preferably 0.5 μm or less, and even more preferably 0.3 μm or less. It is preferable to disperse the organic pigment in such a way as these average particle sizes and then use it.

[0242] The average primary particle size of the organic pigment is preferably less than 100 nm, more preferably less than 50 nm, even more preferably less than 40 nm, and particularly preferably in the range of 10 to 30 nm.

[0243] It should be noted that the average particle size of the organic pigments is determined using a dynamic light scattering particle size analyzer, such as the Nanotrac particle size analyzer "UPA-EX150" or "UPA-EX250" manufactured by Nikkiso Corporation.

[0244] As a colorant used in the formation of a black matrix (BM) by a colored resist composition, there is no particular limitation as long as it is black, and examples include carbon black, lamp black, acetylene black, bone black, thermal cracking carbon black, channel black, furnace black, graphite, iron black, titanium black, etc. Among these, from the viewpoint of light blocking rate and image characteristics, carbon black and titanium black are preferred.

[0245] Alternatively, it can be a combination of two or more organic pigments mixed together to create black.

[0246] Commercially available carbon black products include, for example, those manufactured by Mitsubishi Chemical Corporation, such as MA7, MA8, MA11, MA100, MA100R, MA220, MA230, MA600, #5, #10, #20, #25, #30, #32, #33, #40, #44, #45, #47, #50, #52, #55, #650, #750, #850, #950, # 960, #970, #980, #990, #1000, #2200, #2300, #2350, #2400, #2600, #3050, #3150, #3250, #3600, #3750, #3950, #4000, #4010, OIL7B, OIL9B, OIL11B, OIL30B, OIL31B, etc., Evonik can be cited as an example. Printex3, Printex3OP, Printex30, Printex30OP, Printex40, Printex45, Printex55, Printex60, Printex75, Printex80, Printex85, Printex90, Printex A, Printex L, Printex G, Printex P, Printex U, Printex made by Japan Co., Ltd. V, PrintexG, SpecialBlack550, SpecialBlack 350, SpecialBlack250, SpecialBlack100, SpecialBlack6, SpecialBlack5, SpecialBlack4, Color Black FW1, Color Black FW2, Color Black FW2V, Color Black FW18, Color BlackFW18, Color Black FW200, Color Black S160, Color Black S170, etc., Cabot Corporation can be cited.Monarch120, Monarch280, Monarch460, Monarch800, Monarch880, Monarch900, Monarch1000, Monarch1100, Monarch1300, Monarch14 00, Monarch4630, REGAL99, REGAL99R, REGAL415, REGAL415R, REGAL250, REGAL250R, REGAL330, REGAL400R, REGAL55R0, REGAL660R, BLACK PEARLS480, PEARLS130, VULCAN XC72R, ELFTEX-8, etc., Columbia RAVEN11, RAVEN14, RAVEN15, RAVEN16, RAVEN22RAVEN30, RAVEN35, RAVEN40, RAVEN410, RAVEN420, RAVEN450, RAVEN500, RAVEN780, RAVEN850, RAVEN890H, RAVEN1000, RAVE made by Carbon Company N1020, RAVEN1040, RAVEN1060U, RAVEN1080U, RAVEN1170, RAVEN1190U, RAVEN1250, RAVEN1500, RAVEN2000, RAVEN2500U, RAVEN3500, RAVEN5000, RAVEN5250, RAVEN5750, RAVEN7000, etc. .

[0247] In the carbon black, the material with high optical concentration and high surface resistivity required for the black matrix of the color filter is preferably carbon black coated with resin.

[0248] Commercially available titanium black products include, for example, titanium black 10S, 12S, 13R, 13M, and 13M-C manufactured by Mitsubishi Materials Corporation.

[0249] As a colorant used to form a black matrix (BM), two or more organic pigments can be mixed to form black. For example, a black pigment obtained by mixing red, green and blue pigments can be used.

[0250] Examples of pigments that can be mixed for the preparation of black pigments include: Victoria Pure Blue (CI42595), Auramine O (CI41000), Catilon Brilliant Flavin (Basic 13), Rhodamine 6GCP (CI45160), Rhodamine B (CI45170), Safranin OK70:100 (CI50240), Erioglaucine X (CI42080), No.120 / LIONOLYELLOW (CI21090), LIONOL YELLOW GRO (CI21090), SYMULER FASTYellow 8GF (CI21105), Benzidine Yellow 4T-564D (CI21095), and SYMULER Fast Yellow (CI21105). FASTRed)4015 (CI12355), LIONOL RED 7B4401 (CI15850), Fastogen Blue TGR-L (CI74160), LIONOL BLUE SM (CI26150), LIONOL BLUE ES (CI Pigment Blue 15:6), LIONOGENRed GD (CI Pigment Red 168), LIONOL GREEN 2YS (CI Pigment Green 36), etc.

[0251] Other pigments that can be mixed for the preparation of black pigments include, for example: CI yellow pigments 20, 24, 86, 93, 109, 110, 117, 125, 137, 138, 147, 148, 153, 154, 166; CI orange pigments 36, 43, 51, 55, 59, 61; CI red pigments 9, 97, 122, 123, 149, 168, 177, 180, 192, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240; CI purple pigments 19, 23, 29, 30, 37, 40, 50; CI blue pigments 15, 15:1, 15:4, 22, 60, 64; CI green pigment 7; CI brown pigments 23, 25, 26, etc.

[0252] When carbon black is used as a black pigment, the average primary particle size of the carbon black is preferably in the range of 0.01 to 0.08 μm, and more preferably in the range of 0.02 to 0.05 μm from the perspective of good developability.

[0253] The particle shape of carbon black differs from that of organic pigments. Sometimes it exists as a structure formed by the fusion of primary particles, and other times, fine pores are formed on the particle surface through post-processing. Therefore, in order to represent the particle shape of carbon black, in addition to the average particle size of the primary particles determined by the same method as for organic pigments, it is generally preferable to measure the DBP absorbance (JIS K6221) and the specific surface area based on the BET method (JIS K6217) as indicators of structure and porosity.

[0254] The preferred absorbance of carbon black for dibutyl phthalate (DBP) is 40-100 cm⁻¹. 3 From the perspective of good dispersibility and developability, a range of 50-80 cm / 100g is more preferable. 3 The specific surface area of ​​carbon black based on the BET method is preferably 50~120 m² / 100g. 2 From the perspective of good dispersion stability, the range of / g is more preferably 60~95m. 2 The range of / g.

[0255] Dyes used as colorants in colored resist compositions include, for example, azo dyes, anthraquinone dyes, phthalocyanine dyes, quinone imine dyes, quinoline dyes, nitro dyes, carbonyl dyes, and methylene dyes.

[0256] Examples of azo dyes include: CI Acid Yellow 11, CI Acid Orange 7, CI Acid Red 37, CI Acid Red 180, CI Acid Blue 29, CI Direct Red 28, CI Direct Red 83, CI Direct Yellow 12, CI Direct Orange 26, CI Direct Green 28, CI Direct Green 59, CI Reactive Yellow 2, CI Reactive Red 17, CI Reactive Red 120, CI Reactive Black 5, CI Disperse Orange 5, CI Disperse Red 58, CI Disperse Blue 165, CI Basic Blue 41, CI Basic Red 18, CI Mordant Red 7, CI Mordant Yellow 5, CI Mordant Black 7, etc.

[0257] Examples of anthraquinone dyes include: CI Reduction Blue 4, CI Acid Blue 40, CI Acid Green 25, CI Reactive Blue 19, CI Reactive Blue 49, CI Disperse Red 60, CI Disperse Blue 56, CI Disperse Blue 60, etc.

[0258] Examples of phthalocyanine dyes include CI Vat Blue 5; examples of quinone imine dyes include CI Basic Blue 3 and CI Basic Blue 9; examples of quinoline dyes include CI Solvent Yellow 33, CI Acid Yellow 3, and CI Disperse Yellow 64; and examples of nitro dyes include CI Acid Yellow 1, CI Acid Orange 3, and CI Disperse Yellow 42.

[0259] In terms of the excellent lightfastness, weather resistance and fastness of the obtained coating film, the colorant of the colored resist composition is preferably a pigment, and dyes may also be used in combination with the pigment as needed to adjust the hue.

[0260] In the colored resist composition, the content of the colorant is preferably more than 1% by mass of the total solids of the colored resist composition, more preferably in the range of 5 to 80% by mass, and even more preferably in the range of 5 to 70% by mass.

[0261] When the color resist composition is used to form each pixel of the red (R), green (G), and blue (B) of a color filter, the content of the colorant in the color resist composition is preferably in the range of 5 to 60% by mass of the total solid content of the color resist composition, and more preferably in the range of 10 to 50% by mass.

[0262] When the colored resist composition is used to form the black matrix of a color filter, the content of the colorant in the colored resist composition is preferably in the range of 20 to 80% by mass of the total solids content of the colored resist composition, more preferably in the range of 30 to 70% by mass.

[0263] In colored resist compositions, when the colorant is a pigment, it is preferable to use it in the form of a pigment dispersion prepared by dispersing the pigment in an organic solvent using a dispersant.

[0264] Examples of dispersants include: surfactants; pigment intermediates or derivatives; dye intermediates or derivatives; and resin-type dispersants such as polyamide resins, polyurethane resins, polyester resins, and acrylic resins. Among these, graft copolymers containing nitrogen atoms, acrylic block copolymers containing nitrogen atoms, and urethane resin dispersants are preferred. Because these dispersants contain nitrogen atoms, which have an affinity for pigment surfaces, the portions other than the nitrogen atoms enhance their affinity for the medium, thereby improving dispersion stability.

[0265] These dispersants can be used alone or in combination of two or more.

[0266] Commercially available examples of such dispersants include: BASF's "EFKA" series ("EFKA 46", etc.); BYK Japan KK's "Disperbyk" series and "BYK" series ("BYK-160", "BYK-161", "BYK-2001", etc.); Lubrizol Japan Limited's "Solsperse" series; Shin-Etsu Chemical Industry Co., Ltd.'s "KP" series; Kyoeisha Chemical Co., Ltd.'s "POLYFLOW" series; Kusunoki Chemical Co., Ltd.'s "DISPARLON" series; and Ajinomoto Fine-Techno Co., Inc.'s "AJISPER" series ("AJISPER PB-814", etc.).

[0267] Examples of organic solvents used in preparing the pigment dispersion include: acetate solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; propionate solvents such as ethoxypropionate; aromatic solvents such as toluene, xylene, and methoxybenzene; ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, and diethylene glycol dimethyl ether; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aliphatic hydrocarbon solvents such as hexane; nitrogen compound solvents such as N,N-dimethylformamide, γ-butyrolactam, and N-methyl-2-pyrrolidone; lactone solvents such as γ-butyrolactone; and carbamates.

[0268] These solvents can be used alone or in combination of two or more.

[0269] Examples of methods for preparing the pigment dispersion include methods involving a mixing and dispersion step with a micro-dispersion step, and methods involving only a micro-dispersion step. In the mixing and dispersion step, the colorant, a portion of the alkali-soluble resin, and the desired dispersant are mixed and kneaded. The colorant can be dispersed by applying strong shear force while dispersing using a mixer.

[0270] Examples of machinery used in mixing include twin-roll mills, three-roll mills, ball mills, trommel screens, dispersers, kneaders, co-kneaders, homogenizers, mixers, and single- or twin-shaft extruders.

[0271] The colorant is preferably refined in particle size by means of salt milling or the like before the mixing process.

[0272] In the micro-dispersion process, the colorant particles can be dispersed to a state close to the size of primary particles by mixing and dispersing the substance obtained by adding a solvent to the composition containing the colorant obtained in the mixing and dispersing process, or by mixing and dispersing the substance containing the colorant, alkali-soluble resin, solvent, and the dispersant as needed with a dispersion medium for glass, zirconium oxide, or ceramic particles using a disperser.

[0273] From the viewpoint of improving the transmittance and contrast of the color filter, the average particle size of the primary particles of the colorant is preferably 10-100 nm, more preferably 10-60 nm. It should be noted that the average particle size of the colorant is measured using a dynamic light scattering particle size analyzer, such as the Nanotrac particle size analyzer "UPA-EX150" or "UPA-EX250" manufactured by Nikkiso Co., Ltd.

[0274] The above examples of photoresist compositions and color resist compositions are shown, but are not limited to these.

[0275] [Polarizing plate]

[0276] The leveling agent of the present invention is also suitable for use in polarizing plates.

[0277] A polarizing plate typically comprises the following structure: a polarizing film (polarizing layer) formed by dyeing a dichroic material such as iodine or dichroic dye onto a substrate film made of polyvinyl alcohol film and then stretching and oriented; sandwiched between a polarizing plate protective film (protective layer) such as triacetyl cellulose (TAC) film, polymethyl methacrylate (PMMA) film, polyethylene terephthalate (PET) film, or cyclic olefin polymer (COP) film. The polarizing plate is further protected by a hard coating layer applied to the protective layer.

[0278] By including the leveling agent of the present invention in any layer constituting the polarizing plate, the optical properties of the polarizing plate can be improved, and it is preferable to include the leveling agent of the present invention in the hard coating layer.

[0279] Hard coatings can be formed by curing an active energy curable resin composition containing an active energy ray curable resin and / or an active energy ray curable monomer.

[0280] Examples of active energy ray-curable resins include urethane (meth)acrylate resins, unsaturated polyester resins, epoxy (meth)acrylate resins, polyester (meth)acrylate resins, acrylic (meth)acrylate resins, and resins with maleimide groups. From the viewpoints of transparency and low shrinkage, urethane (meth)acrylate resins are preferred.

[0281] It should be noted that one type of active energy ray curable resin can be used alone, or two or more types can be used in combination.

[0282] The urethane (meth)acrylate resin is preferably a resin having urethane bonds and (meth)acryloyl groups, obtained by reacting an aliphatic polyisocyanate compound or an aromatic polyisocyanate compound with a (meth)acrylate compound having hydroxyl groups.

[0283] Examples of aliphatic and aromatic polyisocyanate compounds include, for instance, tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, heptamethylene diisocyanate, octamethylene diisocyanate, decamethylene diisocyanate, 2-methyl-1,5-pentane diisocyanate, 3-methyl-1,5-pentane diisocyanate, dodecamethylene diisocyanate, 2-methylpentane diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4,4-trimethylhexamethylene diisocyanate. Examples of polyisocyanates include methyl hexamethylene diisocyanate, isophorone diisocyanate, norbornene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated toluene diisocyanate, hydrogenated phenylmethylene diisocyanate, hydrogenated tetramethylphenylmethylene diisocyanate, and cyclohexyl diisocyanate. Additionally, aromatic polyisocyanate compounds include toluene diisocyanate, 4,4'-diphenylmethane diisocyanate, phenylmethylene diisocyanate, 1,5-naphthalene diisocyanate, benzyltoluidine diisocyanate, and terephthalic diisocyanate.

[0284] Examples of hydroxyl-containing acrylate compounds include: 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 1,5-pentanediol mono(meth)acrylate, 1,6-hexanediol mono(meth)acrylate, neopentanediol mono(meth)acrylate, neopentanediol mono(meth)acrylate with hydroxypentanoic acid, and other mono(meth)acrylates of diols; trimethylolpropane di(meth)acrylate, ethoxylated trimethylolpropane (meth)acrylate, propoxylated trimethylolpropane di(meth)acrylate, glycerol di(meth)acrylate, bis(2-(meth)acryloyloxyethyl)hydroxyethyl isocyanurate, and other mono(meth)acrylates or di(meth)acrylates of triols; or hydroxyl-containing mono(meth)acrylates and di(meth)acrylates obtained by modifying a portion of these alcoholic hydroxyl groups with ε-caprolactone. Compounds having a single functional hydroxyl group and three or more functional (meth)acryloyl groups, such as pentaerythritol tri(meth)acrylate, di(trimethylolpropane)tri(meth)acrylate, and dipentaerythritol penta(meth)acrylate, or hydroxyl-containing polyfunctional (meth)acrylates obtained by further modifying the compounds with ε-caprolactone; dipropylene glycol mono(meth)acrylate, diethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and polyethylene glycol mono(meth)acrylate. (Meth)acrylate compounds with oxyalkylene chains, such as (methyl)acrylate; (meth)acrylate compounds with block structures, such as polyethylene glycol-polypropylene glycol mono(meth)acrylate and polyoxybutylene-polyoxypropylene mono(meth)acrylate; and (meth)acrylate compounds with random structures, such as poly(ethylene glycol-tetramethylene glycol) mono(meth)acrylate and poly(propylene glycol-tetramethylene glycol) mono(meth)acrylate.

[0285] The reaction of the aliphatic or aromatic polyisocyanate compound with the acrylate compound having hydroxyl groups can be carried out by known methods in the presence of a carbamate catalyst.

[0286] Specific examples of the carbamate catalysts mentioned above include amines such as pyridine, pyrrole, triethylamine, diethylamine, and dibutylamine; phosphines such as triphenylphosphine and triethylphosphine; organotin compounds such as dibutyltin dilaurate, octyltin trilaurate, octyltin diacetate, and tin octoate; and organometallic compounds such as zinc octoate.

[0287] The unsaturated polyester resin is a curable resin obtained by polycondensation of one or more diacids and diols selected from the group consisting of α,β-unsaturated diacids or their anhydrides, aromatic saturated diacids or their anhydrides, and aliphatic or alicyclic saturated diacids or their anhydrides.

[0288] Examples of α,β-unsaturated dicarboxylic acids or their anhydrides include maleic acid, maleic anhydride, fumaric acid, itaconic acid, citraconic acid, chloromaleic acid, and their esters.

[0289] Examples of aromatic saturated dicarboxylic acids or their anhydrides include phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, nitrophthalic acid, tetrahydrophthalic anhydride, methylene tetrahydrophthalic anhydride, halophthalic anhydride, and their esters.

[0290] Examples of aliphatic or alicyclic saturated dicarboxylic acids include oxalic acid, malonic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, glutaric acid, hexahydrophthalic anhydride, and their esters. Examples of diols include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, 1,3-butanediol, 1,4-butanediol, 2-methylpropane-1,3-diol, neopentyl glycol, triethylene glycol, tetraethylene glycol, 1,5-pentanediol, 1,6-hexanediol, bisphenol A, hydrogenated bisphenol A, ethylene glycol carbonate, and 2,2-bis(4-hydroxypropoxydiphenyl)propane.

[0291] Examples of epoxy vinyl ester resins include resins obtained by reacting (meth)acrylic acid with epoxy groups of epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenolic varnish type epoxy resin, and cresol varnish type epoxy resin.

[0292] Examples of resins having maleimide groups include: difunctional maleimide carbamate compounds obtained by urethane esterification of N-hydroxyethyl maleimide with isophorone diisocyanate; difunctional maleimide ester compounds obtained by esterification of maleimide acetic acid with polytetramethylene glycol; tetrafunctional maleimide ester compounds obtained by esterification of maleimide hexanoic acid with a tetraethylene oxide adduct of pentaerythritol; and polyfunctional maleimide ester compounds obtained by esterification of maleimide acetic acid with a polyol compound.

[0293] Specific examples of monomers that can be cured by active energy rays include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate with a number average molecular weight in the range of 150 to 1000, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate with a number average molecular weight in the range of 150 to 1000, neopentyl glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-Hexanediol di(meth)acrylate, hydroxypentaenoic acid ester neopentyl glycol di(meth)acrylate, bisphenol A di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, pentaerythritol tetra(meth)acrylate, trimethylolpropane di(meth)acrylate, dipentaerythritol penta(meth)acrylate, dicyclopentenyl (meth)acrylate, methyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, decyl (meth)acrylate, (methyl) Isodecyl acrylate, lauryl acrylate, stearyl acrylate, isostearyl acrylate, glyceryl acrylate, 2-hydroxyethyl acrylate, 3-chloro-2-hydroxypropyl acrylate, glycidyl acrylate, allyl acrylate, 2-butoxyethyl acrylate, 2-(diethylamino)ethyl acrylate, 2-(dimethylamino)ethyl acrylate, γ-(methacryloyloxypropyltrimethoxysilane, 2-methoxyethyl acrylate, methoxydiethylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate, nonylbenzene Oxygenated polyethylene glycol (meth)acrylate, nonylphenoxy polypropylene glycol (meth)acrylate, phenoxyethyl methacrylate, phenoxy dipropylene glycol (meth)acrylate, phenoxy polypropylene glycol (meth)acrylate, polybutadiene (meth)acrylate, polyethylene glycol-polypropylene glycol (meth)acrylate, polyethylene glycol-polybutadiene glycol (meth)acrylate, polystyrene ethyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentyl (meth)acrylate, dicyclopentenyl (meth)acrylate, isobornyl (meth)acrylate, methoxylated cyclodectriene (meth)acrylate, phenyl (meth)acrylate, maleimide Amines, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-hexylmaleimide, N-octylmaleimide, N-dodecylmaleimide, N-stearylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, 2-maleimide-ethyl-ethyl carbonate, 2-maleimide-ethyl-propyl carbonate, N-ethyl-(2-maleimide-ethyl)carbamate, N,N-hexamethylenebismaleimide, polypropylene glycol-bis(3-maleimide-propyl) ether, bis(2-maleimide-ethyl) carbonate, 1,4-dimaleimide-cyclohexane, etc.

[0294] It should be noted that one of the active energy ray curing monomers can be used alone, or two or more can be used in combination.

[0295] The active energy-curable monomer is preferably a multifunctional (meth) acrylate with three or more functions, such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and pentaerythritol tetra(meth)acrylate.

[0296] The leveling agent of the present invention in the active energy ray curable resin composition forming the hard coating is preferably in the range of 0.01 to 20 parts by weight relative to 100 parts by weight of the active energy ray curable resin and the active energy ray curable monomer, more preferably in the range of 0.1 to 15 parts by weight, and even more preferably in the range of 0.5 to 10 parts by weight.

[0297] The curing of the active energy ray curable resin composition can be carried out by irradiation with active energy rays, such as ultraviolet rays, electron rays, alpha rays, beta rays, gamma rays, etc.

[0298] The active energy ray-curable resin composition may contain other additives, such as photopolymerization initiators, photosensitizers, polymerization inhibitors, antistatic agents, defoamers, viscosity modifiers, light stabilizers, weather stabilizers, heat stabilizers, antioxidants, rust inhibitors, slip agents, waxes, gloss modifiers, release agents, compatibilizers, conductivity modifiers, pigments, dyes, dispersants, and dispersion stabilizers.

[0299] Among polarizing plates, there are types of polarizing plates in which an anti-reflective layer is further provided on a hard coating, and the leveling agent of the present invention may be included in the anti-reflective layer.

[0300] The antireflective layer is, for example, a layer obtained by curing a composition in which a low refractive index agent is further added to the active energy ray curable resin composition.

[0301] Examples of low refractive index agents include: hollow silica microparticles, silica microparticles with nanoporous structures, and other silica microparticles with pores; and metal fluoride microparticles such as magnesium fluoride, aluminum fluoride, calcium fluoride, and lithium fluoride.

[0302] The thickness of the hard coating or the total thickness of the hard coating and the anti-reflective layer can be set appropriately according to the purpose, for example, it can be set in the range of 1~30μm.

[0303] Example

[0304] The present invention will now be described in detail through examples and comparative examples.

[0305] It should be noted that the present invention is not limited to the following embodiments.

[0306] In the examples and comparative examples, the weight-average molecular weight (Mw) and number-average molecular weight (Mn) are values ​​obtained by converting polystyrene based on gel permeation chromatography (GPC) determination.

[0307] The determination conditions for GPC are as follows.

[0308] [GPC Measurement Conditions]

[0309] Measurement apparatus: Tosoh Corporation's high-efficiency GPC device "HLC-8320GPC"

[0310] Column: "TSK GUARDCOLUMN SuperHZ-L" made by Tosoh Co., Ltd. + "TSK gelSuperHZM-N" made by Tosoh Co., Ltd. + "TSK gel SuperHZM-N" made by Tosoh Co., Ltd. + "TSK gelSuperHZM-N" made by Tosoh Co., Ltd. + "TSK gel SuperHZM-N" made by Tosoh Co., Ltd.

[0311] Detector: RI (Differential Refractometer)

[0312] Data processing: Tosoh Corporation, "EcoSEC Data Analysis Version 1.07"

[0313] Column temperature: 40℃

[0314] Elution solvent: tetrahydrofuran

[0315] Flow rate: 0.35 mL / min

[0316] Test sample: Dissolve 7.5 mg of the sample in 10 ml of tetrahydrofuran, filter the resulting solution through a microfilter, and use the resulting solution as the test sample.

[0317] Sample injection volume: 20 μl

[0318] Standard sample: According to the determination manual of “HLC-8320GPC”, use the following monodisperse polystyrene with a known molecular weight.

[0319] (Monodisperse polystyrene)

[0320] "A-300" manufactured by Tosoh Corporation

[0321] "A-500" manufactured by Tosoh Corporation

[0322] "A-1000" manufactured by Tosoh Corporation

[0323] "A-2500" manufactured by Tosoh Corporation

[0324] "A-5000" manufactured by Tosoh Corporation

[0325] "F-1" manufactured by Tosoh Corporation

[0326] "F-2" manufactured by Tosoh Corporation

[0327] "F-4" manufactured by Tosoh Corporation

[0328] "F-10" manufactured by Tosoh Corporation

[0329] "F-20" manufactured by Tosoh Corporation

[0330] "F-40" manufactured by Tosoh Corporation

[0331] "F-80" manufactured by Tosoh Corporation

[0332] "F-128" manufactured by Tosoh Corporation

[0333] "F-288" manufactured by Tosoh Corporation

[0334] (Synthetic Example 1: Synthesis of a polymer (1) containing organosilicon chains)

[0335] The following mixtures were prepared separately: a mixture A1 consisting of 136.8 g of polypropylene glycol-polybutylene glycol-monomethacrylate (average repetition number of 1 for propylene glycol and average repetition number of 6 for butylene glycol) and 50.0 g of butyl acetate as a solvent; a mixture B1 consisting of 3.0 g of tert-butyl peroxide-2-ethylhexanoate as an initiator and 20.0 g of butyl acetate as a solvent; and a mixture C1 consisting of 63.2 g of a monomethacrylate compound having polysiloxane bonds as shown in the following formula and 30.0 g of butyl acetate as a solvent.

[0336]

[0337] (The average of x2 is 65)

[0338] 200.0 g of butyl acetate as a solvent was added to a glass flask equipped with a stirring device, thermometer, cooling pipe and dropping device, and the mixture was heated to 90°C while being stirred under a nitrogen flow.

[0339] Mixture A1 at 90°C was added dropwise to the flask. Five minutes after the addition of mixture A1, mixtures B1 and C1 at 90°C were added dropwise. The addition of mixture C1 was stopped 120 minutes after the start of the addition, and the addition of mixtures A1 and B1 was stopped 10 minutes after the addition of mixture C1 (135 minutes after the start of the addition of mixture A1). After the addition was complete, the mixture was stirred at 90°C for 10 hours. After the reaction was complete, the solvent was removed by distillation to obtain a polymer (1) containing organosilicon chains.

[0340] The molecular weight of the polymer (1) containing organosilicon chains was determined by GPC, and the weight-average molecular weight was 34,000 (Mw).

[0341] In addition, according to the raw material input ratio, the polymer (1) containing organosilicon chains contains 31.6% by mass of polymeric unsaturated monomers with organosilicon chains.

[0342] (Synthetic Example 2: Synthesis of Polymer (2) Containing Organosilicon Chains)

[0343] The following mixtures were prepared separately: Mixture A2, which was prepared by mixing 136.8 g of polypropylene glycol-polybutylene glycol-monomethacrylate (average repetition number of propylene glycol 1, average repetition number of butylene glycol 6) and 102.8 g of butyl acetate as solvent; Mixture B2, which was prepared by mixing 3.0 g of tert-butyl peroxide-2-ethylhexanoate as initiator and 100.0 g of butyl acetate as solvent; and Mixture C2, which was prepared by mixing 63.2 g of a monomethacrylate compound with polysiloxane bonds, the same as in Synthesis Example 1, and 63.2 g of butyl acetate as solvent.

[0344] 200.0 g of butyl acetate as a solvent was added to a glass flask equipped with a stirring device, thermometer, cooling pipe and dropping device, and the mixture was heated to 90°C while being stirred under a nitrogen flow.

[0345] Mixture A2 at 90°C was added dropwise to the flask. Five minutes after the addition of mixture A2, mixtures B2 and C2 at 90°C were added dropwise. The addition of mixture C2 was stopped 120 minutes after the start of the addition, and the addition of mixtures A2 and B2 was stopped 10 minutes after the addition of mixture C2 (135 minutes after the start of the addition of mixture A2). After the addition was completed, the mixture was stirred at 90°C for 10 hours. After the reaction was completed, the solvent was removed by distillation to obtain a polymer (2) containing organosilicon chains.

[0346] The molecular weight of the obtained polymer (2) containing organosilicon chains was determined by GPC, and the weight-average molecular weight was 14,000 (Mw).

[0347] In addition, according to the raw material input ratio, the polymer (2) containing organosilicon chains contains 31.6% by mass of polymeric unsaturated monomers with organosilicon chains.

[0348] (Comparative Synthesis Example 1: Synthesis of Polymer (3) Containing Organosilicon Chains)

[0349] The following mixtures were prepared separately: Mixture A3, which was prepared by mixing 79.0 g of polypropylene glycol-polybutylene glycol monoacrylate (average repetition number of propylene glycol 1, average repetition number of butylene glycol 6), 5.0 g of methacrylic acid, and 35.71 g of propylene glycol monomethyl ether acetate (PGMEA) as a solvent; Mixture B3, which was prepared by mixing 1.0 g of tert-butyl peroxide-2-ethylhexanoate as an initiator and 30.0 g of PGMEA as a solvent; and Mixture C3, which was prepared by mixing 16.0 g of a monomethacrylate compound with polysiloxane bonds, the same as in Synthesis Example 1, and 20.0 g of PGMEA as a solvent.

[0350] 100.0g of PGMEA as a solvent was added to a glass flask equipped with a stirring device, thermometer, cooling tube and dropping device, and the temperature was raised to 90°C while stirring under a nitrogen flow.

[0351] Mixture A3 at 90°C was added dropwise to the flask. Five minutes after the addition of mixture A3, mixtures B3 and C3 at 90°C were added dropwise. The addition of mixture C3 was stopped 120 minutes after the start of the addition, and the addition of mixtures A3 and B3 was stopped 10 minutes after the addition of mixture C3 (135 minutes after the start of the addition of mixture A3). After the addition was complete, the mixture was stirred at 90°C for 5 hours, and then at 110°C for 1 hour. After the reaction was complete, the solvent was removed by distillation to obtain a polymer (3) containing organosilicon chains.

[0352] The molecular weight of the obtained polymer (3) containing organosilicon chains was determined by GPC, and the weight-average molecular weight was 26,000 (Mw).

[0353] In addition, according to the raw material input ratio, the polymer (3) containing organosilicon chains contains 16% by mass of polymeric unsaturated monomers with organosilicon chains.

[0354] (Comparative Example 2: Synthesis of a polymer (4) containing organosilicon chains)

[0355] The following mixtures were prepared separately: Mixture A4, which was prepared by mixing 180.0 g of polypropylene glycol-polybutylene glycol-monoacrylate (average repetition number of propylene glycol 1, average repetition number of butylene glycol 6) and 50.0 g of propylene glycol monomethyl ether acetate (PGMEA) as a solvent; Mixture B4, which was prepared by mixing 2.0 g of tert-butyl peroxide-2-ethylhexanoate as an initiator and 30.0 g of PGMEA as a solvent; Mixture C4, which was prepared by mixing 20.0 g of a monomethacrylate compound with polysiloxane bonds, the same as in Synthesis Example 1, and 20.0 g of propylene glycol monomethyl ether acetate (PGMEA) as a solvent.

[0356] 200.0 g of PGMEA as a solvent was added to a glass flask equipped with a stirring device, thermometer, cooling tube and dropping device, and the temperature was raised to 85°C while stirring under a nitrogen flow.

[0357] In the flask, mixture A4 at 85°C was added dropwise. Five minutes after the addition of mixture A4, mixtures B4 and C4 at 85°C were added dropwise. The addition of mixture C4 was stopped 120 minutes after the start of the addition, and the addition of mixtures A4 and B4 was stopped 10 minutes after the addition of mixture C4 (135 minutes after the start of the addition of mixture A4). After the addition was complete, the mixture was stirred at 85°C for 5 hours, and then at 110°C for 1 hour. After the reaction was complete, the solvent was removed by distillation to obtain a polymer (4) containing organosilicon chains.

[0358] The molecular weight of the polymer (4) containing organosilicon chains was determined by GPC, and the weight-average molecular weight was 21,000 (Mw).

[0359] In addition, according to the raw material input ratio, the polymer (4) containing organosilicon chains contains 10% by mass of polymeric unsaturated monomers with organosilicon chains.

[0360] (Comparative Example 3: Synthesis of a polymer (5) containing organosilicon chains)

[0361] 100.0 g of butyl acetate as a solvent was added to a glass flask equipped with a stirrer, thermometer, cooling tube, and dropping device, and the mixture was heated to 90°C under a nitrogen stream while stirring. Next, 33.0 g of 3-methacryloyloxypropyltris(trimethylsiloxy)silane, 67.0 g of polypropylene glycol-polybutylene glycol-monomethacrylate, and 70.0 g of butyl acetate as a solvent were mixed to prepare mixture A5. Separately, 3.0 g of tert-butyl peroxide-2-ethylhexanoate as an initiator and 63.3 g of butyl acetate as a solvent were mixed to prepare mixture B5.

[0362] Mixtures A5 and B5 were added dropwise to a glass flask at 90°C over 120 minutes. After the addition was complete, the mixture was stirred at 90°C for 5 hours, then heated to 110°C and stirred for 1 hour. After the reaction was complete, the solvent was removed by distillation to obtain a polymer (5) containing organosilicon chains as a random copolymer.

[0363] The molecular weight of the polymer (5) containing organosilicon chains was analyzed by GPC, and the result was Mw was 17,000. In addition, according to the raw material input ratio, the polymer (5) containing organosilicon chains contained polymeric unsaturated monomers with organosilicon chains had a content of 67% by mass.

[0364] (Comparative Example 4: Synthesis of a polymer (6) containing organosilicon chains)

[0365] 100.0 g of butyl acetate as a solvent was added to a glass flask equipped with a stirrer, thermometer, cooling tube, and dropping device, and the mixture was heated to 90°C under a nitrogen stream while stirring. Next, 33.0 g of 3-methacryloyloxypropyltris(trimethylsiloxy)silane, 67.0 g of polypropylene glycol-polybutylene glycol-monomethacrylate, and 70.0 g of butyl acetate as a solvent were mixed to prepare mixture A6. Separately, 3.0 g of tert-butyl peroxide-2-ethylhexanoate as an initiator and 63.3 g of butyl acetate as a solvent were mixed to prepare mixture B6.

[0366] Mixtures A6 and B6 were added dropwise to a glass flask at 90°C over 120 minutes. After the addition was complete, the mixture was stirred at 90°C for 5 hours, then heated to 110°C and stirred for 1 hour. After the reaction was complete, the solvent was removed by distillation to obtain a polymer (6) containing organosilicon chains as a random copolymer.

[0367] The molecular weight of the polymer (5) containing organosilicon chains was analyzed by GPC, and the result was Mw was 17,000. In addition, according to the raw material input ratio, the polymer (6) containing organosilicon chains contained polymeric unsaturated monomers with organosilicon chains had a content of 33% by mass.

[0368] (Example 1: Evaluation of film formation and smoothness of coating)

[0369] The polymer (1) containing organosilicon chains, manufactured in Synthesis Example 1, was used to form a coating film in the following manner.

[0370] A photoresist composition was prepared by mixing 3.0 g of 40% by weight alkali-soluble resin solution (ACRYDIC ZL-295, manufactured by DIC Corporation), 1.2 g of ARONIX M-402 (manufactured by Toa Synthetic Chemicals Co., Ltd., a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate), 0.0024 g of polymer (1) containing organosilicon chains (in solids form), and 6.23 g of propylene glycol monomethyl ether acetate (PGMEA).

[0371] 3 ml of the obtained resist composition was dropped onto the central part of a 10 cm × 10 cm chrome-plated glass substrate. After spin coating at 1000 rpm for 10 seconds, the substrate was heated and dried at 100°C for 100 seconds to produce a laminate with a coating layer.

[0372] The smoothness and coating defects of the fabricated laminate were evaluated using the following methods. The results are shown in Table 1.

[0373] (Smoothness)

[0374] The smoothness of the coating layer of the laminate obtained by visual observation is evaluated according to the following criteria.

[0375] 〇: Almost no coating unevenness was observed.

[0376] △: Uneven coating was observed in some areas.

[0377] ×: Uneven coating was observed overall.

[0378] (Example 2 and Comparative Examples 1-4: Evaluation of film formation and smoothness of coatings)

[0379] Polymer (1) containing organosilicon chains was replaced with polymer (2) containing organosilicon chains prepared in Synthesis Example 2 and polymers (3) to (6) containing organosilicon chains prepared in Comparative Examples 1-4, respectively. Otherwise, the same evaluation as in Example 1 was performed. The results are shown in Table 1.

[0380] [Table 1]

[0381]

[0382] As shown in Table 1, even leveling agents using polymers with monomers having specific organosilicon chains cannot achieve the desired effect if their content does not meet the characteristics of this invention (exceeding 20% ​​by mass). Furthermore, it can be seen that even polymers with a monomer content exceeding 20% ​​by mass cannot achieve the desired effect if the structure of the organosilicon chain does not meet the characteristics of this invention.

Claims

1. A leveling agent comprising a polymer containing an organosilicon chain, wherein at least a polymerizable monomer (a1) and a polymerizable monomer (a2) are polymerizable components, said polymerizable monomer (a1) having a group comprising a structure shown in general formula (A), and said polymerizable monomer (a2) having one or more groups selected from the group consisting of an alkyl group having 1 to 18 carbon atoms, an aromatic group having 6 to 18 carbon atoms, a group comprising a polyoxyalkylene chain, and a group comprising a polyester chain. The polymerizable monomer (a1) accounts for more than 20% by mass in the polymeric component. In the aforementioned formula (A), R 11 Each is an alkyl group having 1 to 6 carbon atoms. x represents the number of repetitions, with a mean of 20 or higher.

2. The leveling agent according to claim 1, wherein, The group containing the structure shown in general formula (A) is the group shown in general formula (A1) below. In the aforementioned formula (A1), R 11 Each is an alkyl group having 1 to 6 carbon atoms. R 12 Each is an alkyl group having 1 to 6 carbon atoms. R 13 Alkyl groups having 1 to 6 carbon atoms x represents the number of repetitions, with a mean of 20 or higher.

3. The leveling agent according to claim 1 or 2, wherein, The polymerizable monomer (a1) is a compound represented by the following general formula (a1-1). In the general formula (a1-1), R 11 Each is an alkyl group having 1 to 6 carbon atoms. R 12 Each is an alkyl group having 1 to 6 carbon atoms. R 13 Alkyl groups having 1 to 6 carbon atoms x represents the number of repetitions, with a mean of 20 or higher. R 15 It can be a hydrogen atom or a methyl group. L 1 It is a divalent organic group.

4. The leveling agent according to claim 1 or 2, wherein, The polymerizable monomer (a2) comprises a polymerizable monomer having a group containing a polyoxyalkylene chain.

5. The leveling agent according to claim 1 or 2, wherein, The polymerizable monomer (a2) is one or more compounds selected from the group consisting of compounds represented by general formula (a2-1), general formula (a2-2), general formula (a2-3), and general formula (a2-4). In the general formulas (a2-1), (a2-2), (a2-3), and (a2-4), R 21 It can be a hydrogen atom or a methyl group. R 22 Alkyl groups having 1 to 18 carbon atoms R 23 It can be a hydrogen atom or a methyl group. R 24 It is an alkyl group having 1 to 18 hydrogen atoms or carbon atoms. R 25 It can be a hydrogen atom or a methyl group. R 26 It is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 18 carbon atoms and an ether bond. R 27 It can be a hydrogen atom or a methyl group. R 28 It is a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, or an alkyl group having 1 to 18 carbon atoms and an ether bond. L 2 It is a divalent organic group or a single bond. n is an integer in the range of 1 to 4, m represents the number of repetitions, and the average value of m is in the range of 1 to 200. p is an integer in the range of 1 to 10, and q represents the number of repetitions, and the average value of q is in the range of 1 to 100.

6. The leveling agent according to claim 1 or 2, wherein, The polymerizable monomer (a1) accounts for 25 to 50% by mass in the polymeric component.

7. The leveling agent according to claim 1 or 2, wherein, The polymeric component comprises more than 80% by mass of the polymeric monomer (a1) and the polymeric monomer (a2).

8. The leveling agent according to claim 1 or 2, wherein, The polymer containing organosilicon chains does not contain fluorine atoms.

9. The leveling agent according to claim 1 or 2, wherein, The polymer containing organosilicon chains has a weight-average molecular weight of 15,000 or more.

10. A corrosion resist composition comprising the leveling agent as described in claim 1 or 2.

11. A polarizing plate comprising the leveling agent as described in claim 1 or 2.

Images