Leveling agent, resist composition, and polarizing plate

Abstract

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

Description

Leveling agent, resist composition and polarizing plate

[0001] The present invention relates to a leveling agent, a resist composition, and a polarizing plate.

[0002] Leveling agents are added, for example, to smooth the coating film obtained by applying a resist composition. Leveling agents have a wide range of applications, including, for example, in color resist compositions used in the production of color filters for liquid crystal displays. The production of color filters generally involves applying a color resist composition to a glass substrate by a coating method such as spin coating or slit coating, exposing the dried coating film using a mask, and then developing it to form a colored pattern. During this process, if the coating film does not have good smoothness and has uneven thickness, or if there is coating unevenness or repelling, color unevenness in the pixels may occur. Adding a leveling agent to a color resist composition improves the smoothness of the resulting coating film, allowing the surfaces of the red (R), green (G), and blue (B) pixels and the black matrix (BM) formed between these pixels to exhibit high smoothness, resulting in a color filter with minimal color unevenness.

[0003] Fluorine-based leveling agents have been used up until now, but because fluorine-based compounds are suspected of environmental accumulation, there is an urgent need to replace them with non-fluorine-based leveling agents, such as silicone-based compounds (see, for example, Patent Document 1).

[0004] Japanese Patent Application Laid-Open No. 2002-179991

[0005] 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 resist composition and a polarizing plate that contain the same and are capable of forming a coating film with excellent smoothness.

[0006] That is, the present invention relates to a leveling agent, etc. 1. A leveling agent that is a silicone chain-containing polymer having as polymerization components at least a polymerizable monomer (a1) having a group containing a structure represented by the following general formula (A) and a polymerizable monomer (a2) having one or more 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 containing a polyoxyalkylene chain, and a group containing a polyester chain, wherein the proportion of the polymerizable monomer (a1) in the polymerization components is greater than 20 mass%. (In the formula (A), R １１ are each independently an alkyl group having 1 to 6 carbon atoms, and x represents the number of repetitions, the number average value of which is 20 or more. 2. The leveling agent according to 1, wherein the group including the structure represented by general formula (A) is a group represented by the following general formula (A1): (In the formula (A1), R １１ are each independently an alkyl group having 1 to 6 carbon atoms; R １２ are each independently an alkyl group having 1 to 6 carbon atoms; R １３ is an alkyl group having 1 to 6 carbon atoms, and x represents the number of repetitions, the number average value of which is 20 or more.) 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): (In the general formula (a1-1), R １１ are each independently an alkyl group having 1 to 6 carbon atoms; R １２ are each independently an alkyl group having 1 to 6 carbon atoms; R １３ is an alkyl group having 1 to 6 carbon atoms, x represents the number of repetitions, the number average value of which is 20 or more, R １５ is a hydrogen atom or a methyl group, and L １is a divalent organic group.) 4. The leveling agent according to any one of 1 to 3, wherein the polymerizable monomer (a2) is a polymerizable monomer having a group containing a polyoxyalkylene chain. 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 a compound represented by the following general formula (a2-1), a compound represented by the following general formula (a2-2), a compound represented by the following general formula (a2-3), and a compound represented by the following general formula (a2-4): (In the general formulae (a2-1), (a2-2), (a2-3) and (a2-4), R ２１ is a hydrogen atom or a methyl group, R ２２ is an alkyl group having 1 to 18 carbon atoms; R ２３ is a hydrogen atom or a methyl group, R ２４ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; R ２５ is a hydrogen atom or a methyl group, R ２６ 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, and R ２７ is a hydrogen atom or a methyl group, R ２８ 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 ２represents a divalent organic group or a single bond, n is an integer ranging from 1 to 4, m represents the number of repetitions, the number average value of m being in the range of 1 to 200, p is an integer ranging from 1 to 10, q represents the number of repetitions, the number average value of q being in the range of 1 to 100. 6. The leveling agent according to any one of 1 to 5, wherein the proportion of the polymerizable monomer (a1) in the polymerization components is in the range of 25 to 50 mass%. 7. The leveling agent according to any one of 1 to 6, wherein 80 mass% or more of the polymerization components are the polymerizable monomer (a1) and the polymerizable monomer (a2). 8. The leveling agent according to any one of 1 to 7, wherein the silicone chain-containing polymer does not contain a fluorine atom. 9. The leveling agent according to any one of 1 to 8, wherein the silicone chain-containing polymer has a weight average molecular weight of 15,000 or more. 10. A resist composition comprising the leveling agent according to any one of 1 to 9. 11. A polarizing plate comprising the leveling agent according to any one of 1 to 9.

[0007] According to the present invention, there are provided a leveling agent that can impart high smoothness to a coating film, as well as a resist composition and a polarizing plate that contain the same and that can form a coating film with excellent smoothness.

[0008] An embodiment of the present invention will be described below. The present invention is not limited to the following embodiment, and can be carried out by making appropriate modifications within the scope that does not impair the effects of the present invention. In this specification, "(meth)acrylic acid" means one or both of acrylic acid and methacrylic acid.

[0009] [Leveling Agent] The leveling agent of the present invention is a silicone chain-containing polymer having as polymerization components at least a polymerizable monomer (a1) having a group containing a structure represented by general formula (A) below, and a 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 containing a polyoxyalkylene chain, and a group containing a polyester chain, wherein the proportion of the polymerizable monomer (a1) in the polymerization components is greater than 20 mass%: (In the formula (A), R １１ are each independently an alkyl group having 1 to 6 carbon atoms, and x represents the number of repetitions, the number average value of which is 20 or more.

[0010] In the present invention, the term "polymerizable monomer" refers to a compound having a polymerizable unsaturated group, and examples of the polymerizable unsaturated group possessed by the polymerizable monomer (a1) and the polymerizable monomer (a2) include C=C-containing groups such as (meth)acryloyl, (meth)acryloyloxy, (meth)acryloylamino, vinyl ether, allyl, styryl, and maleimide groups. Among these, (meth)acryloyl and (meth)acryloyloxy groups are preferred because of their easy availability as raw materials and good polymerization reactivity. The number of polymerizable unsaturated groups possessed by the polymerizable monomer may be one or two or more.

[0011] In the present invention, the term "polymerizable monomer" refers to a compound having a polymerizable unsaturated group, and examples of the polymerizable unsaturated group possessed by the polymerizable monomer (a1) and the polymerizable monomer (a2) include C=C-containing groups such as a (meth)acryloyl group, a (meth)acryloyloxy group, a (meth)acryloylamino group, a vinyl ether group, an allyl group, a styryl group, and a maleimide group. Among these, a (meth)acryloyl group and a (meth)acryloyloxy group are preferred because of the ease of availability of raw materials and good polymerization reactivity.

[0012] The number of polymerizable unsaturated groups that the polymerizable monomer has may be one or two or more.

[0013] In the present invention, the term "polymerization component" means a component that constitutes a polymer, and does not include solvents, polymerization initiators, and the like that do not constitute a polymer.

[0014] The group containing the structure represented by the general formula (A) is preferably a group represented by the following general formula (A1). (In the formula (A1), R １１ are each independently an alkyl group having 1 to 6 carbon atoms; R １２ are each independently an alkyl group having 1 to 6 carbon atoms; R １３ is an alkyl group having 1 to 6 carbon atoms, and x represents the number of repetitions, the number average value of which is 20 or more.

[0015] In the general formulas (A) and (A1), R１１ , R １２ and R １３ is preferably a methyl group.

[0016] In the general formulas (A) and (A1), the number 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. In the present invention, the "number average value of x" means, for the polymerizable monomer (a1) constituting the polymer of the present invention, the average number of repeating units of siloxane bonds per polymerizable monomer. The number average value of x in the polymer of the present invention can be calculated from the number average molecular weight of the polymer of the present invention.

[0017] The polymerizable monomer (a1) is preferably a compound represented by the following general formula (a1-1):

[0018] (In the general formula (a1-1), R １１ , R １２ , R １３ and x are R in the general formulas (A) and (A1), respectively. １１ , R １２ , R １３ and x, R １５ is a hydrogen atom or a methyl group, and L １ is a divalent organic group.

[0019] L １ The divalent organic group is preferably a single bond, an alkylene group having 1 to 50 carbon atoms, or an alkyleneoxy group having 1 to 50 carbon atoms.

[0020] L １ Examples of the alkylene group having 1 to 50 carbon atoms include a methylene group, an ethylene group, an n-propylene group, an n-butylene group, an n-pentylene group, an n-hexylene group, an n-heptylene group, an n-octylene group, an n-nonylene group, an n-decylene group, an n-dodecylene group, an isopropylene group, a 2-methylpropylene group, a 2-methylhexylene group, and a tetramethylethylene group.

[0021] L １The 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 a methylene group, an ethylene group, an n-propylene group, or an isopropylene group.

[0022] L １ The alkyleneoxy group having 1 to 50 carbon atoms is, for example, one of the alkylene groups -CH ２ - is a group in which - is substituted with -O-. １ The alkyleneoxy group having 1 to 50 carbon atoms is preferably an alkyleneoxy group having 1 to 15 carbon atoms, more preferably an alkyleneoxy group having 1 to 8 carbon atoms, and even more preferably a methyleneoxy group, an ethyleneoxy group, a propyleneoxy group, an oxytrimethylene group, a butyleneoxy group, an oxytetramethylene group, a pentyleneoxy group, a heptyleneoxy group, or an octyleneoxy group.

[0023] L １ When the divalent organic group is an alkylene group having 1 to 50 carbon atoms or an alkyleneoxy group having 1 to 50 carbon atoms, these divalent organic groups are -CH ２ A part of the - may be replaced by a carbonyl group (-C(=O)-), a phenylene group, an amide bond or a urethane bond, and furthermore, a hydroxyl group or the like may be substituted on the carbon atom.

[0024] The polymerizable monomer (a1) can be produced by a known method, or a commercially available product may be used. Specific examples of the polymerizable monomer (a1) include α-(3-methacryloyloxy)propylpolydimethylsiloxane and 3-(methacryloyloxy)propyltris(trimethylsiloxy)silane.

[0025] The polymerizable monomer (a2) is a polymerizable monomer having one or more 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 containing a polyoxyalkylene chain, and a group containing a polyester chain.

[0026] The alkyl group having 1 to 18 carbon atoms contained in the polymerizable monomer (a2) may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, and specific examples thereof include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, a hexadecyl group, etc. The alkyl group having 1 to 18 carbon atoms contained in the polymerizable monomer (a2) is preferably an alkyl group having 1 to 6 carbon atoms.

[0027] Examples of the aromatic group having 6 to 18 carbon atoms contained in the polymerizable monomer (a2) include a phenyl group, a naphthyl group, an anthracen-1-yl group, and a phenanthrene-1-yl group.

[0028] The group containing a (poly)oxyalkylene chain contained in the polymerizable monomer (a2) is a monovalent group containing a repeating oxyalkylene moiety or a divalent linking group containing a repeating oxyalkylene moiety.

[0029] The group containing a polyester chain contained in the polymerizable monomer (a2) is a monovalent group containing a repeating ester bond moiety or a divalent linking group containing a repeating ester bond moiety.

[0030] Examples of the polymerizable monomer (a2) having an alkyl group having 1 to 18 carbon atoms and in which the polymerizable unsaturated group is a (meth)acryloyl group include methyl(meth)acrylate, ethyl(meth)acrylate, n-propyl(meth)acrylate, isopropyl(meth)acrylate, n-butyl(meth)acrylate, s-butyl(meth)acrylate, isobutyl(meth)acrylate, t-butyl(meth)acrylate, n-pentyl(meth)acrylate, n-hexyl(meth)acrylate, n-heptyl(meth)acrylate, n-octyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, decyl(meth)acrylate, and methyl(meth)acrylate. (meth)acrylic acid alkyl esters having 1 to 18 carbon atoms, such as dicyclopentanyloxylethyl (meth)acrylate, dodecyl (meth)acrylate, stearyl (meth)acrylate, and isostearyl (meth)acrylate; and (meth)acrylic acid bridged cyclic alkyl esters having 1 to 18 carbon atoms, such as dicyclopentanyloxylethyl (meth)acrylate, isobornyloxylethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, dimethyladamantyl (meth)acrylate, dicyclopentanyl (meth)acrylate, and dicyclopentenyl (meth)acrylate.

[0031] Examples of the polymerizable monomer (a2) having a phenylalkyl group having 7 to 18 carbon atoms or a phenoxyalkyl group having 7 to 18 carbon atoms and in which the polymerizable unsaturated group is a (meth)acryloyl group include benzyl (meth)acrylate, phenoxymethyl (meth)acrylate, and 2-phenoxyethyl (meth)acrylate.

[0032] Examples of the polymerizable monomer (a2) having an alkyl group having 1 to 18 carbon atoms and in which the polymerizable unsaturated group is a vinyl ether group include alkyl vinyl ethers such as 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, and cyclohexyl vinyl ether; and cycloalkyl vinyl ethers.

[0033] Examples of the polymerizable monomer (a2) having an aromatic group having 6 to 18 carbon atoms include styrene, α-methylstyrene, p-methylstyrene, and p-methoxystyrene.

[0034] Examples of the polymerizable monomer (a2) having an alkyl group having 1 to 18 carbon atoms and in which the polymerizable unsaturated group is a (meth)acryloylamino group include N,N-dimethylacrylamide, N,N-diethylacrylamide, N-isopropylacrylamide, diacetoneacrylamide, and acroylmorpholine.

[0035] Examples of the polymerizable monomer (a2) having an alkyl group having 1 to 18 carbon atoms and in which the polymerizable unsaturated group is a maleimide group include methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, and cyclohexylmaleimide.

[0036] Examples of the polymerizable monomer (a2) having a group containing a polyoxyalkylene chain and in which the polymerizable unsaturated group is a (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, polyethylene glycol.polytetramethylene glycol mono(meth)acrylate, poly(propylene glycol.tetramethylene glycol) mono(meth)acrylate, polypropylene glycol.polytetramethylene glycol mono(meth)acrylate, poly(propylene glycol.1,2-butylene glycol) mono(meth)acrylate, polypropylene glycol.poly1,2-butylene glycol mono(meth)acrylate, Poly(ethylene glycol·1,2-butylene glycol) mono(meth)acrylate, polyethylene glycol·poly 1,2-butylene glycol mono(meth)acrylate, poly(tetraethylene glycol·1,2-butylene glycol) mono(meth)acrylate, polytetraethylene glycol·poly 1,2-butylene glycol mono(meth)acrylate, poly 1,2-butylene glycol mono(meth)acrylate, poly(ethylene glycol·trimethylene glycol) mono(meth)acrylate, polyethylene Glycol / polytrimethylene glycol mono(meth)acrylate, poly(propylene glycol / trimethylene glycol) mono(meth)acrylate, polypropylene glycol / polytrimethylene glycol mono(meth)acrylate, poly(trimethylene glycol / tetramethylene glycol) mono(meth)acrylate, polytrimethylene glycol / polytetramethylene glycol mono(meth)acrylate, poly(1,2-butylene glycol / trimethylene glycol) mono(meth)acrylate, poly 1,Examples include 2-butylene glycol-polytrimethylene glycol mono(meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, poly(1,2-butylene glycol-tetramethylene glycol) mono(meth)acrylate, and poly(1,2-butylene glycol-polytetramethylene glycol mono(meth)acrylate). The above "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.

[0037] The polymerizable monomer (a2) is preferably at least one selected from the group consisting of compounds represented by the following general formula (a2-1), compounds represented by the following general formula (a2-2), compounds represented by the following general formula (a2-3), compounds represented by the following general formula (a2-4), and compounds represented by the following general formula (a2-5), and more preferably at least one selected from the group consisting of compounds represented by the following general formula (a2-1), compounds represented by the following general formula (a2-2), compounds represented by the following general formula (a2-3), and compounds represented by the following general formula (a2-4):

[0038] (In the general formulas (a2-1), (a2-2), (a2-3), (a2-4) and (a2-5), R ２１ is a hydrogen atom or a methyl group, R ２２ is an alkyl group having 1 to 18 carbon atoms; R ２３ is a hydrogen atom or a methyl group, R ２４ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; R ２５ is a hydrogen atom or a methyl group, R ２６ 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, and R ２７ is a hydrogen atom or a methyl group, R ２８is 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 is a divalent organic group or a single bond, R ２９ is a hydrogen atom or a methyl group, R ３０ are each independently an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, n is an integer ranging from 1 to 4, m is the number of repetitions, the number average value of m being in the range of 1 to 200, p is an integer ranging from 1 to 10, q is the number of repetitions, the number average value of q being in the range of 1 to 100, and 1 is an integer ranging from 0 to 5.

[0039] In the general formula (a2-2), the m n's in the parentheses may be the same or different from each other. In the general formula (a2-3), the q p's in the parentheses may be the same or different from each other. In the general formula (a2-4), the q p's in the parentheses may be the same or different from each other.

[0040] L in the general formulae (a2-3) and (a2-4) ２ The divalent organic group is L １ The divalent organic groups are the same as those mentioned above.

[0041] The polymerizable monomer (a2) preferably includes a polymerizable monomer having a group containing a polyoxyalkylene chain, and more preferably includes a compound represented by the general formula (a2-2). When the polymerizable monomer (a2) includes a polymerizable monomer having a group containing a polyoxyalkylene chain, high compatibility with the matrix resin can be expected.

[0042] The polymerizable monomer (a2) preferably contains one or more 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). When the polymerizable monomer (a2) contains one or more 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), it is preferable that 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 50 mass% or more relative to the total amount of the polymerizable monomer (a2).

[0043] The polymerizable monomer (a2) can be produced by a known method. Alternatively, a commercially available product may be used as the polymerizable monomer (a2). For example, commercially available products of the polymerizable monomer (a2) having a group containing a polyoxyalkylene chain and in which the polymerizable unsaturated group is a (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 Co., Ltd., and "BLEMMER PE-90", "BLEMMER PE-200", "BLEMMER PE-350", and "BLEMMER PME-100" manufactured by NOF Corporation. Examples of such polymers include "Blenmer PME-200," "Blenmer PME-400," "Blenmer PME-4000," "Blenmer PP-1000," "Blenmer PP-500," "Blenmer PP-800," "Blenmer 70PEP-350B," "Blenmer 55PET-800," "Blenmer 50POEP-800B," "Blenmer 10PPB-500B," "Blenmer NKH-5050," "Blenmer AP-400," "Blenmer AE-350," the Plaxel F series manufactured by Daicel Corporation, and the Viscoat series manufactured by Osaka Organic Chemical Industry Ltd.

[0044] The content of the polymerizable monomer (a1) in the polymerization components (polymerizable monomer (a1) / total amount of polymerization components) may be more than 20% by mass, preferably 22% by mass or more, and more preferably 25% by mass or more. When the content of the polymerizable monomer (a1) in the polymerization components is within this range, excellent leveling properties can be obtained. The upper limit of the content of the polymerizable monomer (a1) in the polymerization components is not particularly limited, but is, for example, 90% by mass or less, preferably 70% by mass or less, more preferably 50% by mass or less, even more preferably 40% by mass or less, and even more preferably less than 35% by mass. The content of the polymerizable monomer (a1) can be adjusted by the raw material charging ratio of the polymerizable monomer (a1) when producing the polymer of the present invention.

[0045] The mass ratio of the polymerizable monomer (a1) to the polymerizable monomer (a2) in the polymerization components is, for example, polymerizable monomer (a1):polymerizable monomer (a2)=21:79 to 80:20, preferably 22:78 to 60:40, and more preferably 25:75 to 50:50.

[0046] The content of the group represented by general formula (A) in the polymer of the present invention (total mass of groups represented by formula (A) / mass of silicone chain-containing polymer) is, for example, 21 to 80 mass%, preferably 22 to 60 mass%, more preferably 25 to 50 mass%, and even more preferably 25 to 40 mass%. The content of the group represented by general formula (A) can be adjusted by the raw material charging ratio of the polymerizable monomer (a1) used when producing the polymer of the present invention.

[0047] In addition to the polymerizable monomer (a1) and the polymerizable monomer (a2), the polymerization component preferably contains a polymerizable monomer (a3), which is a compound represented by the following general formula (a3-1): By imparting hydrophilicity to the leveling agent, it is possible to improve the developability and recoatability when the leveling agent is used as a resist composition, and it is also possible to improve the recoatability when the leveling agent is used in a polarizing plate.

[0048] (In the general formula (a3-1), R ３１ is a hydrogen atom or a methyl group, R ３２is a hydrogen atom or a hydroxyalkyl group having 1 to 18 carbon atoms.

[0049] 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. The alkyl group having 1 to 18 carbon atoms may be any of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, and specific examples include a methyl group, an ethyl group, a normal propyl group, an isopropyl group, an n-butyl group, a t-butyl group, an n-hexyl group, a cyclohexyl group, an n-octyl group, and a hexadecyl group. The hydroxyalkyl group having 1 to 18 carbon atoms is preferably a hydroxyalkyl group having 1 to 6 carbon atoms.

[0050] When the polymerizable monomer (a3) ​​is contained as a polymerization component, the content of the polymerizable monomer (a3) ​​in the polymer of the present invention is, for example, in the range of 1 to 50 mass %, preferably in the range of 1 to 20 mass %, more preferably in the range of 5 to 20 mass %, and even more preferably in the range of 5 to 15 mass %, of the total amount of the polymerization components.

[0051] The silicone chain-containing polymer (hereinafter sometimes simply referred to as "polymer of the present invention") that is the leveling agent of the present invention may be a polymer containing polymerizable monomer (a1), polymerizable monomer (a2), and any polymerizable monomer (a3) ​​as polymerization components, and the polymerization method is not particularly limited. The polymer of the present invention may be a random copolymer of polymerizable monomer (a1), polymerizable monomer (a2), and any polymerizable monomer (a3), or may be a block copolymer of polymerizable monomer (a1), polymerizable monomer (a2), and any polymerizable monomer (a3), and is preferably a block copolymer of polymerizable monomer (a1), polymerizable monomer (a2), and any polymerizable monomer (a3). For example, when the polymer of the present invention is a block copolymer of polymerizable monomer (a1) and polymerizable monomer (a2), the number and bonding order of the polymer blocks of polymerizable monomer (a1) and the polymer blocks of polymerizable monomer (a2) are not particularly limited, and the polymer may be, for example, a diblock copolymer in which a polymer block of polymerizable monomer (a1) and a polymer block of polymerizable monomer (a2) are bonded.

[0052] In the polymerization components, the polymerizable monomer (a1) may be a single polymerizable monomer (a1) or two or more polymerizable monomers (a1) having different structures. Similarly, in the polymerization components, the polymerizable monomer (a2) may be a single polymerizable monomer (a2) or two or more polymerizable monomers (a2) having different structures. Similarly, in the polymerization components, the polymerizable monomer (a3) ​​may be a single polymerizable monomer (a3) ​​or two or more polymerizable monomers (a3) ​​having different structures.

[0053] The polymerization components may contain the polymerizable monomer (a1), the polymerizable monomer (a2), and the optional polymerizable monomer (a3), and may consist essentially of the polymerizable monomer (a1), the polymerizable monomer (a2), and the optional polymerizable monomer (a3), or may consist solely of the polymerizable monomer (a1), the polymerizable monomer (a2), and the optional polymerizable monomer (a3). Here, "consisting essentially of" means that the total content of the polymerizable monomer (a1), the polymerizable monomer (a2), and the optional polymerizable monomer (a3) ​​in the polymerization components is, for example, 85% by mass or more, 90% by mass or more, 95% by mass or more, or 98% by mass or more.

[0054] The polymerization components do not include, for example, (meth)acrylic acid esters of alkyl monoalcohols and / or (meth)acrylic acid esters of cycloalkyl monoalcohols, where the alkyl monoalcohols have, for example, 1 to 22 carbon atoms and the cycloalkyl monoalcohols have, for example, 3 to 22 carbon atoms.

[0055] The polymer of the present invention preferably does not contain fluorine atoms. A fluorine-atom-free polymer has low environmental accumulation and can reduce the environmental load.

[0056] The polymer of the present invention preferably does not contain a reactive functional group. In the present invention, the "reactive functional group" refers to a functional group that can react with another functional group to form a crosslinked structure or the like, and examples of such a functional group include an isocyanate group, an epoxy group, a carboxyl group, a carboxylic acid halide group, and a carboxylic acid anhydride group.

[0057] 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. There are no particular limitations on the upper limit of the weight average molecular weight (Mw) of the polymer of the present invention, and the weight average molecular weight (Mw) is preferably 100,000 or less, 90,000 or less, 70,000 or less, and 50,000 or less, in that order. The weight average molecular weight (Mw) of the polymer of the present invention is measured by the method described in the Examples.

[0058] [Method for producing silicone chain-containing polymer] The method for producing the polymer of the present invention is not particularly limited, and it can be produced by known methods. The polymer of the present invention can be produced by solution polymerization, bulk polymerization, emulsion polymerization, etc. of the polymerization components based on polymerization mechanisms such as radical polymerization, cationic polymerization, and anionic polymerization. For example, in the case of radical polymerization, the polymer of the present invention can be produced by charging the polymerization components into an organic solvent and adding a general-purpose radical polymerization initiator. The polymer obtained above is a random copolymer.

[0059] As the polymerization initiator, various types can be used, for example, peroxides such as t-butylperoxy-2-ethylhexanoate, benzoyl peroxide, and diacyl peroxide, azo compounds such as azobisisobutyronitrile, dimethyl azobisisobutyrate, and phenylazotriphenylmethane, Mn(acac) ３ If necessary, a chain transfer agent such as lauryl mercaptan, 2-mercaptoethanol, ethyl thioglycolic acid, or octyl thioglycolic acid, or a thiol compound having a coupling group such as γ-mercaptopropyltrimethoxysilane may be used as an additive such as a chain transfer agent.

[0060] Examples of the organic solvent include alcohols such as ethanol, isopropyl alcohol, n-butanol, iso-butanol, and tert-butanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and methyl amyl ketone; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, and butyl lactate; monocarboxylic acid esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, butyl 2-oxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, and butyl 2-methoxypropionate; dimethylformamide, dimethyl sulfoxide, N-methyl Examples of the solvent include polar solvents such as pyrrolidone, ethers such as methyl cellosolve, cellosolve, butyl cellosolve, butyl carbitol, and ethyl cellosolve acetate, propylene glycols and esters thereof such as propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monobutyl ether acetate, halogenated solvents such as 1,1,1-trichloroethane and chloroform, ethers such as tetrahydrofuran and dioxane, aromatic solvents such as benzene, toluene, and xylene, and fluorinated inert liquids such as perfluorooctane and perfluorotri-n-butylamine. These solvents can be used alone or in combination of two or more.

[0061] Preferably, the polymer of the present invention is prepared by starting the addition of the polymerizable monomer (a1) to the reaction system, adding the polymerizable monomer (a2) and a polymerization initiator to the reaction system after the start of the addition of the polymerizable monomer (a1), and then completing the addition of the polymerizable monomer (a1) before the addition of the polymerizable monomer (a2) and the polymerization initiator. By polymerizing the polymer of the present invention in this manner, the amount of unreacted silicone chains can be minimized, thereby suppressing coating defects that may be caused by additives during coating.

[0062] The polymerizable monomer (a1) may contain impurities such as compounds having a cyclic siloxane structure, and the compounds having a cyclic siloxane structure may be removed by distilling the polymerizable monomer (a1) before adding it to the reaction system, or by distilling the polymer after the reaction, etc. Distillation can be carried out by a known method, for example, thin-film distillation.

[0063] The polymer of the present invention can also be produced by subjecting the polymerization components to living polymerization such as living radical polymerization or living anionic polymerization.

[0064] In living radical polymerization, a dormant species, whose active polymerization terminal is protected by an atom or atomic group, reversibly generates radicals and reacts with a monomer, thereby causing a propagation reaction. Even when a first monomer is consumed, the propagating terminal does not lose its activity and reacts with a second monomer that is successively added to produce a block polymer. Examples of such living radical polymerization include atom transfer radical polymerization (ATRP), reversible addition-fragmentation radical polymerization (RAFT), nitroxide-mediated radical polymerization (NMP), and organotellurium radical polymerization (TERP). While there are no particular restrictions on which of these methods is used, ATRP is preferred due to its ease of control. ATRP uses an organic halide or a sulfonyl halide compound as a polymerization initiator and a metal complex composed of a transition metal compound and a ligand as a catalyst.

[0065] Specific examples of polymerization initiators that can be used in ATRP include 1-phenylethyl chloride, 1-phenylethyl bromide, chloroform, carbon tetrachloride, 2-chloropropionitrile, α,α'-dichloroxylene, α,α'-dibromoxylene, hexakis(α-bromomethyl)benzene, and C1-6 alkyl esters of C2-halogenated carboxylic acids (e.g., 2-chloropropionic acid, 2-bromopropionic acid, 2-chloroisobutyric acid, 2-bromoisobutyric acid, etc.). More specific examples of C1-6 alkyl esters of C2-halogenated carboxylic acids include, for example, methyl 2-chloropropionate, ethyl 2-chloropropionate, methyl 2-bromopropionate, and ethyl 2-bromoisobutyrate.

[0066] The transition metal compounds that can be used in ATRP are M ｎ＋ X ｎ It is expressed as follows: M ｎ＋ X ｎ The transition metal M of the transition metal compound represented by ｎ＋ As the ＋ , 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 Ag２＋ M ｎ＋ X ｎ X in the transition metal compound represented by the formula (I) is a halogen atom, an alkoxyl group having 1 to 6 carbon atoms, (SO ４ ) １／２ , (PO ４ ) １／３ , (HPO ４ ) １／２ , (H ２ P.O. ４ ), triflate, hexafluorophosphate, methanesulfonate, arylsulfonate (preferably benzenesulfonate or toluenesulfonate), SeR １１ , CN and R １２ COO, where R １１ represents an aryl group or a linear or branched alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), R １２ represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms (preferably a methyl group) which may be substituted 1 to 5 times with halogen (preferably 1 to 3 times with fluorine or chlorine). ｎ＋ X ｎ In the transition metal compound represented by the formula (I), n represents the formal charge on the metal and is an integer of 0 to 7.

[0067] Examples of the ligand compound capable of forming a coordinate bond to the transition metal of the transition metal compound include a compound having a ligand containing one or more nitrogen atoms, oxygen atoms, phosphorus atoms, or sulfur atoms that can be coordinated to the transition metal via a σ bond, a compound having a ligand containing two or more carbon atoms that can be coordinated to the transition metal via a π bond, and a compound having a ligand that can be coordinated to the transition metal via a μ bond or an η bond.

[0068] The transition metal complex is not particularly limited, but preferred examples include complexes of transition metals of Groups 7, 8, 9, 10, and 11, and more preferred examples include complexes of zero-valent copper, monovalent copper, divalent ruthenium, divalent iron, or divalent nickel.

[0069] Specific examples of catalysts that can be used in ATRP include complexes with ligands such as 2,2'-bipyridyl and its derivatives, 1,10-phenanthroline and its derivatives, and polyamines such as tetramethylethylenediamine, pentamethyldiethylenetriamine, and hexamethyltris(2-aminoethyl)amine when the central metal is copper. Examples of divalent ruthenium complexes include dichlorotris(triphenylphosphine)ruthenium, dichlorotris(tributylphosphine)ruthenium, dichloro(cyclooctadiene)ruthenium, dichlorobenzeneruthenium, dichloro-p-cymeneruthenium, dichloro(norbornadiene)ruthenium, cis-dichlorobis(2,2'-bipyridine)ruthenium, dichlorotris(1,10-phenanthroline)ruthenium, and carbonylchlorohydridotris(triphenylphosphine)ruthenium. Examples of divalent iron complexes include bistriphenylphosphine complexes and triazacyclononane complexes.

[0070] In living radical polymerization, it is preferable to use a solvent. 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; halogenated 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. The above solvents may be used alone or in combination of two or more.

[0071] When the polymer of the present invention is produced by living polymerization, it can be produced, for example, by any of Methods 1 to 3 shown below. Method 1: A method in which polymerizable monomer (a1) and polymerizable monomer (a2) are subjected to living radical polymerization (preferably atom transfer radical polymerization) in the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of forming a coordinate bond with the transition metal, and a solvent. Method 2: A method in which polymerizable monomer (a1) is subjected to living radical polymerization (preferably atom transfer radical polymerization) in the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of forming a coordinate bond with the transition metal, and a solvent to obtain a polymer block of polymerizable monomer (a1), and then 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). Method 3: A method in which a polymerizable monomer (a2) is subjected to living radical polymerization (preferably atom transfer radical polymerization) in the presence of a polymerization initiator, a transition metal compound, a ligand compound capable of forming a coordinate bond with the transition metal, and a solvent to obtain a polymer block of the polymerizable monomer (a2), and then the polymerizable monomer (a1) is added to the reaction system to further subject the polymerizable monomer (a1) to living radical polymerization (preferably atom transfer radical polymerization) to the polymer block of the polymerizable monomer (a2).

[0072] The polymerization temperature during the living radical polymerization is preferably in the range of room temperature to 120°C.

[0073] When the polymer of the present invention is produced by living radical polymerization, metals resulting from the transition metal compound used in the polymerization may remain in the resulting polymer. The metals remaining in the resulting polymer may be removed using activated alumina or the like after the polymerization is completed.

[0074] [Resist Composition] The leveling agent of the present invention is suitable for use in resist compositions. Resist compositions (such as photoresist compositions and color resist compositions for color filters) require high leveling properties. Resist compositions are typically applied by spin coating to a thickness of approximately 1 to 2 μm on a silicon wafer or a glass substrate vapor-deposited with various metals. If the coating thickness fluctuates or coating unevenness occurs, the linearity and reproducibility of the pattern deteriorate, resulting in the failure to obtain a resist pattern with the desired precision. In addition to these problems, various leveling-related issues also exist, such as drop marks, overall unevenness, and a beading phenomenon in which the edge portion is thicker than the center portion. The resist composition of the present invention contains the leveling agent of the present invention, which exhibits high leveling properties and is capable of forming a uniform coating film (cured product), thereby resolving the above-mentioned problems. Furthermore, the leveling agent of the present invention can be a fluorine-atom-free leveling agent, which does not contain fluorine atoms and therefore has low environmental accumulation and low environmental impact.

[0075] The content of the leveling agent of the present invention in the resist composition of the present invention will vary depending on the type of base resin, the coating method, the desired film thickness, etc., but is preferably from 0.0001 to 10 parts by mass, more preferably from 0.001 to 5 parts by mass, and even more preferably from 0.01 to 2 parts by mass, per 100 parts by mass of the solids content of the resist composition (e.g., the base resin). When the content of the leveling agent of the present invention is within this range, the desired leveling properties can be obtained and problems such as foaming during coating can be suppressed.

[0076] When the resist composition of the present invention is used as a photoresist composition, the photoresist composition contains an alkali-soluble resin, a radiation-sensitive substance (photosensitive substance), a solvent, and the like in addition to the leveling agent of the present invention.

[0077] The alkali-soluble resin contained in the photoresist composition is a resin that is soluble in an alkaline solution, which is the developer used for patterning the resist. Examples of alkali-soluble resins include novolak resins obtained by condensing an aromatic hydroxy compound derivative such as phenol, cresol, xylenol, resorcinol, phloroglucinol, or hydroquinone with an aldehyde compound such as formaldehyde, acetaldehyde, or benzaldehyde; polymers or copolymers of vinylphenol compound derivatives such as o-vinylphenol, m-vinylphenol, p-vinylphenol, or α-methylvinylphenol; (meth)acrylic acid polymers or copolymers such as acrylic acid, methacrylic acid, or hydroxyethyl (meth)acrylate; polyvinyl alcohol; modified resins obtained by introducing radioactive ray-sensitive groups such as quinone diazide groups, naphthoquinone azide groups, aromatic azide groups, or aromatic cinnamoyl groups via some of the hydroxyl groups of these various resins; and urethane resins containing acidic groups such as carboxylic acid or sulfonic acid in the molecule. These alkali-soluble resins may be used alone or in combination of two or more.

[0078] The radiation-sensitive substance contained in the photoresist composition is a substance that changes the solubility of an alkali-soluble resin in a developer by irradiation with energy rays such as ultraviolet rays, far ultraviolet rays, excimer laser light, X-rays, electron beams, ion beams, molecular beams, gamma rays, etc. 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, poly(olefin sulfone) compounds, etc.

[0079] Examples of the quinone diazide compounds include 1,2-benzoquinone azide-4-sulfonic acid esters, 1,2-naphthoquinone diazide-4-sulfonic acid esters, 1,2-naphthoquinone diazide-5-sulfonic acid esters, 2,1-naphthoquinone diazide-4-sulfonic acid esters, 2,1-naphthoquinone diazide-5-sulfonic acid esters, and sulfonic acid chlorides of quinone diazide derivatives such as 1,2-benzoquinone azide-4-sulfonic acid chloride, 1,2-naphthoquinone diazide-4-sulfonic acid chloride, 1,2-naphthoquinone diazide-5-sulfonic acid chloride, 2,1-naphthoquinone diazide-4-sulfonic acid chloride, and 2,1-naphthoquinone diazide-5-sulfonic acid chloride.

[0080] Examples of the diazo compounds include salts of condensates of p-diazodiphenylamine with formaldehyde or acetaldehyde, inorganic diazo resin salts which are reaction products of the above condensates with hexafluorophosphates, tetrafluoroborates, perchlorates or periodates, and organic diazo resin salts which are reaction products of the above condensates with sulfonic acids, as described in U.S. Pat. No. 3,300,309.

[0081] Examples of the azide compounds include azidochalconic acid, diazidobenzalmethylcyclohexanones, azidocinnamylideneacetophenones, aromatic azide compounds, and aromatic diazide compounds.

[0082] Examples of the halogenated organic compound include halogen-containing oxadiazole compounds, halogen-containing triazine compounds, halogen-containing acetophenone compounds, halogen-containing benzophenone compounds, halogen-containing sulfoxide compounds, halogen-containing sulfone compounds, halogen-containing thiazole compounds, halogen-containing oxazole compounds, halogen-containing trizole compounds, halogen-containing 2-pyrone compounds, halogen-containing aliphatic hydrocarbon compounds, halogen-containing aromatic hydrocarbon compounds, halogen-containing heterocyclic compounds, and sulfenyl halide compounds. In addition to the above, compounds used as halogen-based flame retardants such as tris(2,3-dibromopropyl)phosphate, tris(2,3-dibromo-3-chloropropyl)phosphate, chlorotetrabromomethane, hexachlorobenzene, hexabromobenzene, hexabromocyclododecane, hexabromobiphenyl, tribromophenyl allyl 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, and compounds used as organic chloro-based pesticides such as dichlorophenyltrichloroethane are also exemplified as halogenated organic compounds.

[0083] Examples of the organic acid ester include carboxylic acid esters and sulfonic acid esters. Examples of the organic acid amide include carboxylic acid amides and sulfonic acid amides. Examples of the organic acid imide include carboxylic acid imides and sulfonic acid imides. The radiation-sensitive substance may be used alone or in combination of two or more.

[0084] In the photoresist composition, the content of the radiation-sensitive substance is preferably in the range of 10 to 200 parts by weight, and more preferably in the range of 50 to 150 parts by weight, per 100 parts by weight of the alkali-soluble resin.

[0085] Examples of solvents for photoresist compositions include ketones such as acetone, methyl ethyl ketone, cyclohexanone, cyclopentanone, cycloheptanone, 2-heptanone, methyl isobutyl ketone, and butyrolactone; alcohols such as methanol, ethanol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, tert-butyl alcohol, pentanol, heptanol, octanol, nonanol, and decanol; ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and dioxane; alcohol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, and propylene glycol monopropyl ether; ethyl formate, propyl formate, butyl formate, methyl acetate, ethyl acetate, butyl acetate, propyl acetate, methyl propionate, ethyl propionate, propyl propionate, butyl propionate, methyl butyrate, and butyl methyl butylate. esters such as ethyl butyrate, butyl butyrate, propyl butyrate, ethyl lactate, and butyl lactate; monocarboxylic acid esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, butyl 2-oxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, and butyl 2-methoxypropionate; cellosolve acetate, methyl cellosolve acetate, ethyl cellosolve acetate, propyl cellosolve acetate, and butyl cellosolve acetate. propylene glycols such as propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and propylene glycol monobutyl ether acetate; diethylene glycols such as diethyl glycol monomethyl ether, diethyl glycol monoethyl ether, diethyl glycol dimethyl ether, diethyl glycol diethyl ether, and diethyl glycol methyl ethyl ether;Examples of suitable solvents include halogenated hydrocarbons such as trichloroethylene, chlorofluorocarbon solvents, HCFCs, and HFCs; fully fluorinated solvents such as perfluorooctane; aromatic solvents such as toluene and xylene; and polar solvents such as dimethylacetiamide, dimethylformamide, N-methylacetamide, and N-methylpyrrolidone. These solvents may be used alone or in combination of two or more.

[0086] When the resist composition of the present invention is used as a color resist composition, the color resist composition contains an alkali-soluble resin, a polymerizable compound, a colorant, and the like in addition to the leveling agent of the present invention.

[0087] The alkali-soluble resin contained in the color resist can be the same as the alkali-soluble resin contained in the photoresist composition described above.

[0088] The polymerizable compound contained in the color resist composition is a compound having a photopolymerizable functional group that can polymerize or crosslink when exposed to active energy rays such as ultraviolet rays. Examples of the polymerizable compound 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 the above-mentioned aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds, polymerizable compounds having a urethane skeleton obtained by reacting a polyisocyanate compound with a (meth)acryloyl group-containing hydroxy compound, and polymerizable compounds having an acid group. The polymerizable compounds may be used alone or in combination of two or more.

[0089] Examples of the esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids include (meth)acrylic acid esters such as 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, and glycerol (meth)acrylate. Other examples include itaconic acid esters in which the (meth)acrylic acid portion of these acrylates is replaced with itaconic acid, crotonic acid esters in which the (meth)acrylic acid portion is replaced with crotonic acid, or maleic acid esters in which the (meth)acrylic acid portion is replaced with maleic acid.

[0090] Examples of the esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids include hydroquinone di(meth)acrylate, resorcinol di(meth)acrylate, and pyrogallol tri(meth)acrylate. The esters obtained by the esterification reaction of unsaturated carboxylic acids, polycarboxylic acids, and polyhydroxy compounds may be a single substance or a mixture. 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 glycerin.

[0091] Examples of the polymerizable compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a (meth)acryloyl group-containing hydroxy compound include reaction products of aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; alicyclic diisocyanates such as cyclohexane diisocyanate and isophorone diisocyanate; and aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate with a hydroxy compound having a (meth)acryloyl group, such as 2-hydroxyethyl(meth)acrylate and 3-hydroxy[1,1,1-tri(meth)acryloyloxymethyl]propane.

[0092] The polymerizable compound having an acid group is, for example, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and is preferably a polyfunctional polymerizable compound obtained by reacting a non-aromatic carboxylic acid anhydride with the unreacted hydroxyl groups of the aliphatic polyhydroxy compound to provide an acid group. The aliphatic polyhydroxy compound used to prepare the polyfunctional polymerizable compound is preferably pentaerythritol or dipentaerythritol. The acid value of the polyfunctional polymerizable compound is preferably in the range of 0.1 to 40, more preferably 5 to 30, because this improves developability, curability, and the like. When two or more polyfunctional polymerizable compounds having an acid group are used in combination, or when a polyfunctional polymerizable compound having an acid group and a polyfunctional polymerizable compound not having an acid group are used in combination, it is preferable that the acid value of the mixture of polymerizable compounds be within the above range.

[0093] Specific examples of the polymerizable compound having an acid group include a mixture containing dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and a succinate ester of dipentaerythritol pentaacrylate as main components, and this mixture is commercially available as Aronix TO-1382 (manufactured by Toagosei Co., Ltd.).

[0094] Other polymerizable compounds include (meth)acrylamides such as ethylenebis(meth)acrylamide; allyl esters such as diallyl phthalate; and compounds having a vinyl group such as divinyl phthalate.

[0095] In the color resist composition, the content of the polymerizable compound is preferably in the range of 5 to 80 mass % of the total solid content of the color resist composition, more preferably in the range of 10 to 70 mass %, and even more preferably in the range of 20 to 50 mass %.

[0096] The colorant for the color resist composition is not particularly limited as long as it is capable of coloring, and may be, for example, a pigment or a dye. The pigment may be either an organic or inorganic pigment. Examples of the organic pigment include red, green, blue, yellow, purple, orange, and brown pigments. Examples of the chemical structure of the organic pigment include azo, phthalocyanine, quinacridone, benzimidazolone, isoindolinone, dioxazine, indanthrene, and perylene. Examples of the inorganic pigment include barium sulfate, lead sulfate, titanium oxide, yellow lead, red iron oxide, and chromium oxide. The abbreviation "C.I." in the following text stands for Color Index.

[0097] Examples of the red pigment include C.I. 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, 53:3, 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, 16 6, 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, 232, 233, 234 5, 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, C.I. Pigment Red 48:1, 122, 168, 177, 202, 206, 207, 209, 224, 242 or 254 is preferred, and C.I. Pigment Red 177, 209, 224 or 254 is more preferred.

[0098] Examples of the green pigment include C.I. 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, C.I. Pigment Green 7, 36, or 58 is preferred.

[0099] Examples of the blue pigment include C.I. 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. Among these, C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, or 15:6 is preferred, and C.I. Pigment Blue 15:6 is more preferred.

[0100] Examples of the yellow pigment include C.I. 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, 1 38, 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, 191:1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208, etc. Among these, C.I. Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180 or 185 is preferred, and C.I. Pigment Yellow 83, 138, 139, 150 or 180 is more preferred.

[0101] Examples of the purple pigment include C.I. 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, C.I. Pigment Violet 19 or 23 is preferred, and C.I. Pigment Violet 23 is more preferred.

[0102] Examples of the orange pigment include C.I. 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, C.I. Pigment Orange 38 or 71 is preferred.

[0103] The three primary color pixels of color filters used in liquid crystal display devices and organic EL display devices are red (R), green (G), and blue (B). Therefore, the red pigment, green pigment, and blue pigment are used as main components, and organic pigments of colors such as yellow, purple, and orange may be used to adjust the hue in order to improve color reproducibility.

[0104] 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, in order to enhance the brightness of color liquid crystal displays and organic EL display devices. It is preferable to use the organic pigment after dispersing it so that the average particle size falls within these ranges. The average primary particle size of the organic pigment is preferably 100 nm or less, more preferably 50 nm or less, even more preferably 40 nm or less, and particularly preferably in the range of 10 to 30 nm. The average particle size of the organic pigment is measured using a dynamic light scattering particle size distribution analyzer, and can be measured using, for example, a Nanotrac particle size distribution analyzer "UPA-EX150" or "UPA-EX250" manufactured by Nikkiso Co., Ltd.

[0105] When the color resist composition is used to form a black matrix (BM), the colorant is not particularly limited as long as it is black, and examples thereof include carbon black, lamp black, acetylene black, bone black, thermal black, channel black, furnace black, graphite, iron black, and titanium black. Among these, carbon black and titanium black are preferred from the viewpoint of light-shielding rate and image characteristics. Furthermore, a combination of two or more organic pigments may be used to produce a black color by mixing them.

[0106] Commercially available carbon black products include, for example, 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, and # 3250, #3600, #3750, #3950, #4000, #4010, OIL7B, OIL9B, OIL11B, OIL30B, OIL31B, and the like manufactured by Evonik Degussa Japan Co., Ltd. are also suitable. A, Printex L, Printex G, Printex P, Printex U, Printex V, PrintexG, SpecialBlack550, SpecialBlack 350, SpecialBlack250, SpecialBlack100, SpecialBlack6, SpecialBlack5, SpecialBlack4, Color Black FW1, Color Black FW2, Color Black FW2V, Color Black FW18, Color Black FW18, Color Black FW200, Color Black S160, Color Black S170, and the like, and Monarch 120, Monarch 280, Monarch 460, Monarch 800, Monarch 880, Monarch 900, Monarch 1000, Monarch 1100, Monarch 1300, Monarch 1400, Monarch 4630, REGAL 99, REGAL 99R, REGAL 415, REGAL 415R, REGAL 250, REGAL 250R, REGAL 330, REGAL 400R, REGAL 55R0, REGAL 660R, and the like manufactured by Cabot Japan Co., Ltd.BLACK PEARLS480, PEARLS130, VULCAN XC72R, ELFTEX-8, etc., and RAVEN11, RAVEN14, RAVEN15, RAVEN16, RAVEN22, RAVEN30, RAVEN35, RAVEN40, RAVEN410, RAVEN420, RAVEN450, RAVEN500, RAVEN780, RAVEN850, RAVEN890H, ...2, RAVEN13, RAVEN14, RAVEN15, RAVEN16, RAVEN17, RAVEN18, RAVEN19, RAVEN20, RAVEN21, RAVEN222, RAVEN23, RAVEN24 1000, RAVEN 1020, RAVEN 1040, RAVEN 1060U, RAVEN 1080U, RAVEN 1170, RAVEN 1190U, RAVEN 1250, RAVEN 1500, RAVEN 2000, RAVEN 2500U, RAVEN 3500, RAVEN 5000, RAVEN 5250, RAVEN 5750, RAVEN 7000, and the like.

[0107] Among the above carbon blacks, resin-coated carbon black is preferred as it has the high optical density and high surface resistivity required for the black matrix of a color filter.

[0108] Examples of commercially available titanium black include titanium black 10S, 12S, 13R, 13M, and 13M-C manufactured by Mitsubishi Materials Corporation.

[0109] As a colorant used for forming a black matrix (BM), two or more organic pigments may be mixed to produce a black color, and examples thereof include a black pigment obtained by mixing three color pigments, i.e., red, green, and blue. Examples of colorants that can be mixed to prepare a black pigment include Victoria Pure Blue (C.I. 42595), Auramine O (C.I. 41000), Catilon Brilliant Flavin (Basic 13), Rhodamine 6 GCP (C.I. 45160), Rhodamine B (C.I. 45170), Safranin OK70:100 (C.I. 50240), Erioglaucine X (C.I. 42080), No. 120 / Lionol Yellow (C.I. 21090), Lionol Yellow GRO (C.I. 21090), Shimler Fast Yellow 8GF (C.I. 21105), Benzidine Yellow 4T-564D (C.I. 21095), Shimler First Red 4015 (C.I. 12355), Lionol Red 7B4401 (C.I. 15850), Firstgen Blue TGR-L (C.I. 74160), Lionol Blue SM (C.I. 26150), Lionol Blue ES (C.I. Pigment Blue 15:6), Lionogen Red GD (C.I. Pigment Red 168), Lionol Green 2YS (C.I. Pigment Green 36), and the like.

[0110] Other colorants that can be mixed and used to prepare a black pigment include, for example, C.I. Yellow Pigments 20, 24, 86, 93, 109, 110, 117, 125, 137, 138, 147, 148, 153, 154, 166, C.I. Orange Pigments 36, 43, 51, 55, 59, 61, C.I. Red Pigments 9, 97, 122, 123, 149, 168, 177, 180, 192, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, C.I. Violet Pigments 19, 23, 29, 30, 37, 40, 50, C.I. Examples of suitable pigments include C.I. blue pigments 15, 15:1, 15:4, 22, 60, and 64, C.I. green pigment 7, and C.I. brown pigments 23, 25, and 26.

[0111] When carbon black is used as the 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 in view of good developability.

[0112] Carbon black has a particle shape different from that of organic pigments and exists in a state called a structure in which primary particles are fused together, and fine pores may be formed on the particle surface by post-treatment. Therefore, to express the particle shape of carbon black, it is generally preferable to measure the DBP absorption (JIS K6221) and the specific surface area (JIS K6217) measured by the BET method in addition to the average particle size of the primary particles, which is determined by the same method as for the organic pigments, and use these as indicators of the structure and pore volume. The dibutyl phthalate (hereinafter abbreviated as "DBP") absorption of carbon black is 40 to 100 cm. ３ / 100g, and in view of good dispersibility and developability, the range of 50 to 80 cm ３ The specific surface area of ​​carbon black measured by the BET method is preferably in the range of 50 to 120 m ２ / g, and in view of good dispersion stability, a range of 60 to 95 m ２ / g is more preferred.

[0113] Examples of dyes that can be used as colorants in the color resist composition include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinoneimine dyes, quinoline dyes, nitro dyes, carbonyl dyes, and methine dyes.

[0114] Examples of the azo dyes include C.I. Acid Yellow 11, C.I. Acid Orange 7, C.I. Acid Red 37, C.I. Acid Red 180, C.I. Acid Blue 29, C.I. Direct Red 28, C.I. Direct Red 83, C.I. Direct Yellow 12, C.I. Direct Orange 26, C.I. Direct Green 28, C.I. Direct Green 59, C.I. Reactive Yellow 2, C.I. Reactive Red 17, C.I. Reactive Red 120, C.I. Reactive Black 5, C.I. Disperse Orange 5, C.I. Disperse Red 58, C.I. Disperse Blue 165, C.I. Basic Blue 41, C.I. Basic Red 18, C.I. Examples of suitable pigments include C.I. Mordant Red 7, C.I. Mordant Yellow 5, and C.I. Mordant Black 7.

[0115] Examples of the anthraquinone dye include C.I. Vat Blue 4, C.I. Acid Blue 40, C.I. Acid Green 25, C.I. Reactive Blue 19, C.I. Reactive Blue 49, C.I. Disperse Red 60, C.I. Disperse Blue 56, and C.I. Disperse Blue 60.

[0116] Examples of the phthalocyanine dyes include C.I. Pad Blue 5, examples of the quinoneimine dyes include C.I. Basic Blue 3 and C.I. Basic Blue 9, examples of the quinoline dyes include C.I. Solvent Yellow 33, C.I. Acid Yellow 3 and C.I. Disperse Yellow 64, and examples of the nitro dyes include C.I. Acid Yellow 1, C.I. Acid Orange 3 and C.I. Disperse Yellow 42.

[0117] It is preferable to use a pigment as the colorant for the color resist composition, since the resulting coating film will have excellent light resistance, weather resistance, and fastness. However, in order to adjust the hue, a dye may be used in combination with the pigment, if necessary.

[0118] In the color resist composition, the content of the colorant is preferably 1 mass % or more, more preferably in the range of 5 to 80 mass %, and even more preferably in the range of 5 to 70 mass %, of the total solid content of the color resist composition.

[0119] When the color resist composition is used to form red (R), green (G), and blue (B) pixels of a color filter, the content of the colorant in the color resist composition is preferably in the range of 5 to 60 mass % of the total solid content of the color resist composition, and more preferably in the range of 10 to 50 mass %.

[0120] When the color resist composition is used to form a black matrix of a color filter, the content of the colorant in the color resist composition is preferably in the range of 20 to 80 mass % of the total solid content of the color resist composition, and more preferably in the range of 30 to 70 mass %.

[0121] In the color resist composition, when the colorant is a pigment, it is preferable to use a pigment dispersion prepared by dispersing the pigment in an organic solvent using a dispersant. Examples of the dispersant 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, the nitrogen atoms have affinity for the pigment surface, and the portions other than the nitrogen atoms increase affinity for the medium, thereby improving dispersion stability. These dispersants may be used alone or in combination of two or more.

[0122] Commercially available dispersants include the "EFKA" series (such as "EFKA 46") manufactured by BASF; the "Disperbyk" series and the "BYK" series (such as "BYK-160", "BYK-161", and "BYK-2001") manufactured by BYK Japan K.K.; the "Solsperse" series manufactured by The Lubrizol Japan Co., Ltd.; the "KP" series manufactured by Shin-Etsu Chemical Co., Ltd.; the "Polyflow" series manufactured by Kyoeisha Chemical Co., Ltd.; the "Disparlon" series manufactured by Kusumoto Chemicals Co., Ltd.; and the "AJISPER" series (such as "AJISPER PB-814") manufactured by Ajinomoto Fine-Techno Co., Ltd.

[0123] Examples of organic solvents used in preparing the pigment dispersion include acetate-based solvents such as propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate; propionate-based solvents such as ethoxypropionate; aromatic solvents such as toluene, xylene, and methoxybenzene; ether-based solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, and diethylene glycol dimethyl ether; ketone-based solvents such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; aliphatic hydrocarbon-based solvents such as hexane; nitrogen compound-based solvents such as N,N-dimethylformamide, γ-butyrolactam, and N-methyl-2-pyrrolidone; lactone-based solvents such as γ-butyrolactone; carbamic acid esters, etc. These solvents may be used alone or in combination of two or more.

[0124] Methods for preparing the pigment dispersion include a method that includes a colorant kneading / dispersing step and a fine-dispersing step, and a method that includes only the fine-dispersing step. In the kneading / dispersing step, the colorant, a portion of the alkali-soluble resin, and, if necessary, the dispersant are mixed and kneaded. The colorant can be dispersed by dispersing while applying strong shear force using a kneader. Machines that can be used for kneading include two-roll mills, three-roll mills, ball mills, tron ​​mills, dispersers, kneaders, co-kneaders, homogenizers, blenders, and single- or twin-screw extruders. It is preferable to refine the particle size of the colorant by a salt milling method or the like before the above kneading.

[0125] In the fine dispersion step, a solvent is added to the composition containing the colorant obtained in the kneading and dispersion step, or a mixture of a colorant, an alkali-soluble resin, a solvent, and, if necessary, the dispersant is mixed and dispersed together with a dispersion medium such as fine particles of glass, zirconia, or ceramic using a disperser, thereby dispersing the colorant particles to a fine state close to primary particles.

[0126] From the viewpoint of improving the transmittance, contrast, etc. of the color filter, the average particle size of the primary particles of the colorant is preferably 10 to 100 nm, and more preferably 10 to 60 nm. The average particle size of the colorant is measured with a dynamic light scattering particle size distribution analyzer, and can be measured with, for example, Nanotrac particle size distribution analyzers "UPA-EX150" and "UPA-EX250" manufactured by Nikkiso Co., Ltd.

[0127] Although photoresist compositions and color resist compositions have been exemplified above as resist compositions, the present invention is not limited to these.

[0128] [Polarizing Plate] The leveling agent of the present invention can also be suitably used in polarizing plate applications. Polarizing plates generally have a structure in which a polarizing film (polarizing layer) is formed by dyeing and adsorbing a dichroic material such as iodine or a dichroic dye onto a substrate film made of a polyvinyl alcohol film, and then stretching and aligning the film, and the polarizing film is sandwiched between polarizing plate protective films (protective layers) such as triacetyl cellulose (TAC) film, polymethyl methacrylate (PMMA) film, polyethylene terephthalate (PET) film, and cycloolefin polymer (COP) film. The polarizing plate is further protected by a hard coat layer provided on the protective layer. The optical properties of the polarizing plate can be improved by including the leveling agent of the present invention in any of the layers constituting the polarizing plate, and the leveling agent of the present invention is preferably included in the hard coat layer.

[0129] The hard coat layer can be formed by curing an active energy curable resin composition, and the active energy curable composition contains an active energy ray curable resin and / or an active energy ray curable monomer.

[0130] Examples of the active energy ray-curable resin include urethane (meth)acrylate resin, unsaturated polyester resin, epoxy (meth)acrylate resin, polyester (meth)acrylate resin, acrylic (meth)acrylate resin, and resin having a maleimide group, and urethane (meth)acrylate resin is preferred from the viewpoints of transparency, low shrinkage, etc. The active energy ray-curable resin may be used alone or in combination of two or more thereof.

[0131] The urethane (meth)acrylate resin is preferably a resin having a urethane bond and a (meth)acryloyl group obtained by reacting an aliphatic polyisocyanate compound or an aromatic polyisocyanate compound with a (meth)acrylate compound having a hydroxyl group.

[0132] Examples of the aliphatic polyisocyanate compound and aromatic polyisocyanate compound include 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-methylpentamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4,4-trimethylhexamethylene diisocyanate. Examples of the aromatic polyisocyanate compounds include tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, xylylene diisocyanate, 1,5-naphthalene diisocyanate, tolidine diisocyanate, and p-phenylene diisocyanate.

[0133] Examples of the acrylate compound having a hydroxyl group include mono(meth)acrylates of dihydric alcohols such as 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, neopentyl glycol mono(meth)acrylate, and hydroxypivalic acid neopentyl glycol mono(meth)acrylate. mono- or di(meth)acrylates of trihydric alcohols such as trimethylolpropane di(meth)acrylate, ethoxylated trimethylolpropane di(meth)acrylate, propoxylated trimethylolpropane di(meth)acrylate, glycerin di(meth)acrylate, bis(2-(meth)acryloyloxyethyl)hydroxyethyl isocyanurate, or mono- and di(meth)acrylates having hydroxyl groups in which some of the alcoholic hydroxyl groups have been modified with ε-caprolactone; pentaerythritol tri(meth)acrylate Examples of the hydroxyl group-containing (meth)acrylate include compounds having a monofunctional hydroxyl group and a trifunctional or higher functional (meth)acryloyl group, such as ethylene glycol mono(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, and dipentaerythritol penta(meth)acrylate, or polyfunctional (meth)acrylates having a hydroxyl group obtained by further modifying such compounds with ε-caprolactone; (meth)acrylate compounds having an oxyalkylene chain, such as dipropylene glycol mono(meth)acrylate, diethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and polyethylene glycol mono(meth)acrylate; (meth)acrylate compounds having an oxyalkylene chain with a block structure, such as polyethylene glycol-polypropylene glycol mono(meth)acrylate and polyoxybutylene-polyoxypropylene mono(meth)acrylate; and (meth)acrylate compounds having an oxyalkylene chain with a random structure, such as poly(ethylene glycol-tetramethylene glycol) mono(meth)acrylate and poly(propylene glycol-tetramethylene glycol) mono(meth)acrylate.

[0134] The reaction of the aliphatic polyisocyanate compound or aromatic polyisocyanate compound with the hydroxyl group-containing acrylate compound can be carried out by a known method in the presence of a urethanization catalyst. Specific examples of the urethanization catalyst include amines such as pyridine, pyrrole, triethylamine, diethylamine, and dibutylamine, phophines such as triphenylphosphine and triethylphosphine, organic tin compounds such as dibutyltin dilaurate, octyltin trilaurate, octyltin diacetate, dibutyltin diacetate, and tin octylate, and organic metal compounds such as zinc octylate.

[0135] The unsaturated polyester resin is a curable resin obtained by polycondensation of one or more dibasic acids selected from the group consisting of α,β-unsaturated dibasic acids or acid anhydrides thereof, aromatic saturated dibasic acids or acid anhydrides thereof, and aliphatic or alicyclic saturated dibasic acids or acid anhydrides thereof, with glycols.

[0136] Examples of the α,β-unsaturated dibasic acids or acid anhydrides thereof include maleic acid, maleic anhydride, fumaric acid, itaconic acid, citraconic acid, chloromaleic acid, and esters thereof. Examples of the aromatic saturated dibasic acids or acid anhydrides thereof include phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid, nitrophthalic acid, tetrahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, halogenated phthalic anhydride, and esters thereof. Examples of the aliphatic or alicyclic saturated dibasic acids include oxalic acid, malonic acid, succinic acid, adipic acid, sebacic acid, azelaic acid, glutaric acid, hexahydrophthalic anhydride, and esters thereof. Examples of glycols 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-di-(4-hydroxypropoxydiphenyl)propane.

[0137] Examples of the epoxy vinyl ester resin include those obtained by reacting (meth)acrylic acid with the epoxy group of an epoxy resin such as a bisphenol A type epoxy resin, a bisphenol F type epoxy resin, a phenol novolac type epoxy resin, or a cresol novolac type epoxy resin.

[0138] Examples of the resin having a maleimide group include a bifunctional maleimide urethane compound obtained by urethanizing N-hydroxyethylmaleimide and isophorone diisocyanate, a bifunctional maleimide ester compound obtained by esterifying maleimide acetic acid and polytetramethylene glycol, a tetrafunctional maleimide ester compound obtained by esterifying maleimide caproic acid and a tetraethylene oxide adduct of pentaerythritol, and a polyfunctional maleimide ester compound obtained by esterifying maleimide acetic acid and a polyhydric alcohol compound.

[0139] Specific examples of the active energy ray-curable monomer include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate having 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 having a number average molecular weight in the range of 150 to 1000, neo Pentyl glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, hydroxypivalic 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, trimethylol dipentaerythritol penta(meth)acrylate, dicyclopentenyl(meth)acrylate, methyl(meth)acrylate, propyl(meth)acrylate, butyl(meth)acrylate, t-butyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, octyl(meth)acrylate, decyl(meth)acrylate, isodecyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, isostearyl(meth)acrylate, glycerol(meth)acrylate acrylate, 2-hydroxyethyl (meth)acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, glycidyl (meth)acrylate, allyl (meth)acrylate, 2-butoxyethyl (meth)acrylate, 2-(diethylamino)ethyl (meth)acrylate, 2-(dimethylamino)ethyl (meth)acrylate, γ-(meth)acryloxypropyltrimethoxysilane, 2-methoxyethyl (meth)acrylate, methoxydiethylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate,Nonylphenoxy polyethylene glycol (meth)acrylate, nonylphenoxy polypropylene glycol (meth)acrylate, phenoxyethyl (meth)acrylate, phenoxy dipropylene glycol (meth)acrylate, phenoxy polypropylene glycol (meth)acrylate, polybutadiene (meth)acrylate, polyethylene glycol-polypropylene glycol (meth)acrylate, polyethylene glycol-polybutylene glycol (meth)acrylate, polystyrylethyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, isobornyl (meth)acrylate , methoxylated cyclodecatriene (meth)acrylate, phenyl (meth)acrylate, maleimide, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-hexylmaleimide, N-octylmaleimide, N-dodecylmaleimide, N-stearylmaleimide, N-phenylmaleimide, N-cyclohexylmaleimide, 2-maleimidoethyl-ethyl carbonate, 2-maleimidoethyl-propyl carbonate, N-ethyl-(2-maleimidoethyl)carbamate, N,N-hexamethylenebismaleimide, polypropylene glycol-bis(3-maleimidopropyl)ether, bis(2-maleimidoethyl)carbonate, 1,4-dimaleimidocyclohexane, etc. The active energy ray-curable monomer may be used alone or in combination of two or more thereof.

[0140] The active energy ray-curable monomer is preferably a trifunctional or higher polyfunctional (meth)acrylate such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, or pentaerythritol tetra(meth)acrylate.

[0141] The content of the leveling agent of the present invention in the active energy ray-curable resin composition that forms the hard coat layer is preferably in the range of 0.01 to 20 parts by mass, more preferably in the range of 0.1 to 15 parts by mass, and even more preferably in the range of 0.5 to 10 parts by mass, relative to 100 parts by mass of the total of the active energy ray-curable resin and the active energy ray-curable monomer.

[0142] The active energy ray-curable resin composition can be cured by irradiation with active energy rays, and the active energy rays can be ionizing radiation such as ultraviolet rays, electron beams, α rays, β rays, and γ rays.

[0143] The active energy ray-curable resin composition may contain other additives. Examples of the other additives include a photopolymerization initiator, a photosensitizer, a polymerization inhibitor, an antistatic agent, an antifoaming agent, a viscosity modifier, a light resistance stabilizer, a weather resistance stabilizer, a heat resistance stabilizer, an antioxidant, a rust inhibitor, a slip agent, a wax, a gloss adjuster, a release agent, a compatibilizer, an electrical conductivity adjuster, a pigment, a dye, a dispersant, and a dispersion stabilizer.

[0144] There are polarizing plates of a type in which an antireflection layer is further provided on the hard coat layer, and the leveling agent of the present invention may be contained in the antireflection layer.

[0145] The antireflection layer is obtained by, for example, curing a composition obtained by further adding a low refractive index agent to the active energy ray-curable resin composition. Examples of the low refractive index agent include silica fine particles having voids, such as hollow silica fine particles and silica fine particles having a nanoporous structure, and metal fluoride fine particles, such as magnesium fluoride, aluminum fluoride, calcium fluoride, and lithium fluoride.

[0146] The thickness of the hard coat layer, or the total thickness of the hard coat layer and the anti-reflection layer, may be appropriately set depending on the purpose, and may be set, for example, in the range of 1 to 30 μm.

[0147] The present invention will be specifically described below with reference to examples and comparative examples, but the present invention is not limited to the following examples.

[0148] In the examples and comparative examples, the weight average molecular weight (Mw) and number average molecular weight (Mn) are values ​​calculated in terms of polystyrene based on gel permeation chromatography (GPC) measurements. The GPC measurement conditions are as follows:

[0149] [GPC measurement conditions] Measurement apparatus: High-speed GPC apparatus "HLC-8320GPC" manufactured by Tosoh Corporation Column: "TSK GUARDCOLUMN SuperHZ-L" manufactured by Tosoh Corporation + "TSK gel SuperHZM-N" manufactured by Tosoh Corporation + "TSK gel SuperHZM-N" manufactured by Tosoh Corporation + "TSK gel SuperHZM-N" manufactured by Tosoh Corporation + "TSK gel SuperHZM-N" manufactured by Tosoh Corporation Detector: RI (differential refractometer) Data processing: "EcoSEC Data Analysis Version 1.07" manufactured by Tosoh Corporation Column temperature: 40°C Developing solvent: tetrahydrofuran Flow rate: 0.35 mL / min Measurement sample: 7.5 mg of sample was dissolved in 10 ml of tetrahydrofuran, and the resulting solution was filtered through a microfilter to prepare the measurement sample. Sample injection amount: 20 μl Standard sample: The following monodisperse polystyrene with known molecular weight was used in accordance with the measurement manual for the "HLC-8320GPC".

[0150] (Monodisperse polystyrene) "A-300" manufactured by Tosoh Corporation "A-500" manufactured by Tosoh Corporation "A-1000" manufactured by Tosoh Corporation "A-2500" manufactured by Tosoh Corporation "A-5000" manufactured by Tosoh Corporation "F-1" manufactured by Tosoh Corporation "F-2" manufactured by Tosoh Corporation "F-4" manufactured by Tosoh Corporation "F-10" manufactured by Tosoh Corporation "F-20" manufactured by Tosoh Corporation "F-40" manufactured by Tosoh Corporation "F-80" manufactured by Tosoh Corporation "F-128" manufactured by Tosoh Corporation "F-288" manufactured by Tosoh Corporation

[0151] Synthesis Example 1 Synthesis of Silicone Chain-Containing Polymer (1) Mixed solution A1 was prepared by mixing 136.8 g of polypropylene glycol-polybutylene glycol-monomethacrylate (average repeat number of propylene glycol: 1, average repeat number of butylene glycol: 6) and 50.0 g of butyl acetate as a solvent, mixed solution B1 was prepared by mixing 3.0 g of t-butylperoxy-2-ethylhexanoate as an initiator and 20.0 g of butyl acetate as a solvent, and mixed solution C1 was prepared by mixing 63.2 g of a monomethacrylate compound having a polysiloxane bond represented by the following formula and 30.0 g of butyl acetate as a solvent.

[0152] (The average of x2 is 65)

[0153] A glass flask equipped with a stirrer, thermometer, condenser, and dropping device was charged with 200.0 g of butyl acetate as a solvent, and the temperature was raised to 90°C while stirring under a nitrogen stream. Dropwise addition of mixed solution A1 at 90°C was initiated into the flask, and 5 minutes after the start of dropwise addition of mixed solution A1, dropwise addition of mixed solutions B1 and C1 at 90°C was initiated. Dropwise addition of mixed solution C1 was completed 120 minutes after the start of dropwise addition, and dropwise addition of mixed solutions A1 and B1 was completed 10 minutes after the end of dropwise addition of mixed solution C1 (135 minutes after the start of dropwise addition of mixed solution A1). After completion of dropwise addition, the mixture was stirred at 90°C for 10 hours. After completion of the reaction, the solvent was distilled off to obtain a silicone chain-containing polymer (1).

[0154] The molecular weight of the resulting silicone chain-containing polymer (1) was measured by GPC, and the weight average molecular weight (Mw) was found to be 34,000. Furthermore, based on the raw material charging ratio, the content of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (1) was found to be 31.6% by mass.

[0155] (Synthesis Example 2: Synthesis of Silicone Chain-Containing Polymer (2)) A mixed solution A2 was prepared by mixing 136.8 g of propylene glycol-polybutylene glycol-monomethacrylate (average repeat number of propylene glycol: 1, average repeat number of butylene glycol: 6) and 102.8 g of butyl acetate as a solvent, a mixed solution B2 was prepared by mixing 3.0 g of t-butylperoxy-2-ethylhexanoate as an initiator and 100.0 g of butyl acetate as a solvent, and a mixed solution C2 was prepared by mixing 63.2 g of the same monomethacrylate compound having a polysiloxane bond as in Synthesis Example 1 and 63.2 g of butyl acetate as a solvent.

[0156] A glass flask equipped with a stirrer, thermometer, condenser, and dropping device was charged with 200.0 g of butyl acetate as a solvent, and the temperature was raised to 90°C while stirring under a nitrogen stream. Dropwise addition of mixed solution A2 at 90°C was initiated into the flask, and 5 minutes after the start of dropwise addition of mixed solution A2, dropwise addition of mixed solutions B2 and C2 at 90°C was initiated. Dropwise addition of mixed solution C2 was completed 120 minutes after the start of dropwise addition, and dropwise addition of mixed solutions A2 and B2 was completed 10 minutes after the end of dropwise addition of mixed solution C2 (135 minutes after the start of dropwise addition of mixed solution A2). After completion of dropwise addition, the mixture was stirred at 90°C for 10 hours. After completion of the reaction, the solvent was distilled off to obtain a silicone chain-containing polymer (2).

[0157] The molecular weight of the resulting silicone chain-containing polymer (2) was measured by GPC, and the weight average molecular weight (Mw) was found to be 14,000. Furthermore, based on the raw material charging ratio, the content of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (2) was found to be 31.6% by mass.

[0158] Comparative Synthesis Example 1: Synthesis of Silicone Chain-Containing Polymer (3) Mixed solution A3 was prepared by mixing 79.0 g of polypropylene glycol-polybutylene glycol-monoacrylate (average repeat number of propylene glycol: 1, average repeat 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; mixed solution B3 was prepared by mixing 1.0 g of t-butylperoxy-2-ethylhexanoate as an initiator and 30.0 g of PGMEA as a solvent; and mixed solution C3 was prepared by mixing 16.0 g of the same monomethacrylate compound having a polysiloxane bond as in Synthesis Example 1 and 20.0 g of PGMEA as a solvent.

[0159] A glass flask equipped with a stirrer, thermometer, condenser, and dropping device was charged with 100.0 g of PGMEA as a solvent and heated to 90°C while stirring under a nitrogen stream. Mixture A3 at 90°C was added dropwise to the flask, and 5 minutes after the start of the addition of mixture A3, mixture B3 and mixture C3 at 90°C were added dropwise. Mixture C3 was added 120 minutes after the start of the addition, and mixtures A3 and B3 were added 10 minutes after the end of the addition of mixture C3 (135 minutes after the start of the addition of mixture A8). 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 distilled off to obtain a silicone chain-containing polymer (3).

[0160] The molecular weight of the resulting silicone chain-containing polymer (3) was measured by GPC, and the weight average molecular weight (Mw) was found to be 26,000. Furthermore, based on the raw material charging ratio, the content of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (3) was found to be 16% by mass.

[0161] Comparative Synthesis Example 2: Synthesis of Silicone Chain-Containing Polymer (4) Mixed solution A4 was prepared by mixing 180.0 g of polypropylene glycol-polybutylene glycol-monoacrylate (average repeat number of propylene glycol: 1, average repeat number of butylene glycol: 6) and 50.0 g of propylene glycol monomethyl ether acetate (PGMEA) as a solvent; mixed solution B4 was prepared by mixing 2.0 g of t-butylperoxy-2-ethylhexanoate as an initiator and 30.0 g of PGMEA as a solvent; and mixed solution C4 was prepared by mixing 20.0 g of the same monomethacrylate compound having a polysiloxane bond as in Synthesis Example 1 and 20.0 g of propylene glycol monomethyl ether acetate (PGMEA) as a solvent.

[0162] A glass flask equipped with a stirrer, thermometer, condenser, and dropping device was charged with 200.0 g of PGMEA as a solvent and heated to 85°C while stirring under a nitrogen stream. Mixture A4 at 85°C was added dropwise to the flask, and 5 minutes after the start of the addition of mixture A4, mixture B4 and mixture C5 at 85°C were added dropwise. Mixture C4 was added 120 minutes after the start of the addition, and mixtures A4 and B4 were added 10 minutes after the end of 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 distilled off to obtain a silicone chain-containing polymer (4).

[0163] The molecular weight of the resulting silicone chain-containing polymer (4) was measured by GPC, and the weight average molecular weight (Mw) was found to be 21,000. Furthermore, based on the raw material charging ratio, the content of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (4) was found to be 10% by mass.

[0164] Comparative Synthesis Example 3: Synthesis of Silicone Chain-Containing Polymer (5) A glass flask equipped with a stirrer, thermometer, condenser, and dropping device was charged with 100.0 g of butyl acetate as a solvent, and the temperature was raised to 90°C while stirring under a nitrogen stream. Next, 33.0 g of 3-methacryloyloxypropyltris(trimethylsiloxy)silane, 67.0 g of propylene glycol-polybutylene glycol-monomethacrylate, and 70.0 g of butyl acetate as a solvent were mixed to prepare mixed solution A5. Furthermore, 3.0 g of t-butylperoxy-2-ethylhexanoate as an initiator and 63.3 g of butyl acetate as a solvent were mixed to prepare mixed solution B5. Mixtures A5 and B5 were added dropwise to the glass flask at 90°C over 120 minutes. After completion of the dropwise addition, the mixture was stirred at 90°C for 5 hours, then heated to 110°C and stirred for 1 hour. After the reaction was completed, the solvent was removed by distillation under reduced pressure to obtain a silicone chain-containing polymer (5), which was a random copolymer.

[0165] The molecular weight of the resulting silicone chain-containing polymer (5) was analyzed by GPC, and the Mw was found to be 17,000. Furthermore, based on the raw material charging ratio, the content of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (5) was found to be 67% by mass.

[0166] Comparative Synthesis Example 4: Synthesis of Silicone Chain-Containing Polymer (6) A glass flask equipped with a stirrer, thermometer, condenser, and dropping device was charged with 100.0 g of butyl acetate as a solvent, and the temperature was raised to 90°C while stirring under a nitrogen stream. Next, 33.0 g of 3-methacryloyloxypropyltris(trimethylsiloxy)silane, 67.0 g of propylene glycol-polybutylene glycol-monomethacrylate, and 70.0 g of butyl acetate as a solvent were mixed to prepare mixed solution A6. Furthermore, 3.0 g of t-butylperoxy-2-ethylhexanoate as an initiator and 63.3 g of butyl acetate as a solvent were mixed to prepare mixed solution B6. Mixtures A and B were added dropwise to the glass flask at 90°C over 120 minutes. After completion of the dropwise addition, the mixture was stirred at 90°C for 5 hours, then heated to 110°C and stirred for 1 hour. After the reaction was completed, the solvent was removed by distillation under reduced pressure to obtain a silicone chain-containing polymer (6), which was a random copolymer.

[0167] The molecular weight of the resulting silicone chain-containing polymer (5) was analyzed by GPC, and the Mw was found to be 17,000. Furthermore, based on the raw material charging ratio, the content of the polymerizable unsaturated monomer having a silicone chain in the silicone chain-containing polymer (6) was found to be 33 mass%.

[0168] Example 1: Formation of coating film and evaluation of smoothness A coating film was formed as follows using the silicone chain-containing polymer (1) produced in Synthesis Example 1. A resist composition was prepared by mixing 3.0 g of a 40 mass % resin solution of an alkali-soluble resin (ACRYDIC ZL-295, manufactured by DIC Corporation), 1.2 g of ARONIX M-402 (manufactured by Toagosei Chemical Industry Co., Ltd., a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate), 0.0024 g (in terms of solids content) of the silicone chain-containing polymer (1), and 6.23 g of propylene glycol monomethyl ether acetate (PGMEA). 3 ml of the obtained resist composition was dropped onto the center of a 10 cm × 10 cm chrome-plated glass substrate, and spin-coated at a rotation speed of 1000 rpm for 10 seconds. The substrate was then heated and dried on a hot plate at 100°C for 100 seconds to produce a laminate having a coating layer.

[0169] The coating layer of the prepared laminate was evaluated for smoothness and coating defects by the following methods. The results are shown in Table 1.

[0170] (Smoothness) The coating layer of the obtained laminate was visually observed, and the smoothness of the coating layer was evaluated according to the following criteria: ◯: Almost no coating unevenness was observed. Δ: Coating unevenness was observed in some areas. ×: Coating unevenness was observed throughout.

[0171] (Example 2 and Comparative Examples 1 to 4: Coating Film Formation and Smoothness Evaluation) The same evaluation as in Example 1 was carried out, except that the silicone chain-containing polymer (2) produced in Synthesis Example 2 and the silicone chain-containing polymers (3) to (6) produced in Synthesis Comparative Examples 1 to 4 were used instead of the silicone chain-containing polymer (1). The results are shown in Table 1.

[0172]

[0173] The results in Table 1 show that even when the leveling agent is a polymer using a specific monomer having a silicone chain, the desired effect is not obtained if the content does not satisfy the requirement of the present invention (more than 20% by mass).Furthermore, even when the proportion of the monomer having a silicone chain is more than 20% by mass, the desired effect is not obtained if the silicone chain structure does not satisfy the requirement of the present invention.

Claims

1. A leveling agent which is a silicone chain-containing polymer having as polymerization components at least a polymerizable monomer (a1) having a group containing a structure represented by the following general formula (A) and a polymerizable monomer (a2) having one or more 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 containing a polyoxyalkylene chain, and a group containing a polyester chain, wherein the proportion of the polymerizable monomer (a1) in the polymerization components is more than 20 mass%. (In the above formula (A), R １１ are each independently an alkyl group having 1 to 6 carbon atoms, and x represents the number of repetitions, the number average value being 20 or more.

2. The leveling agent according to claim 1, wherein the group containing the structure represented by general formula (A) is a group represented by the following general formula (A1): (In the above formula (A1), R １１ are each independently an alkyl group having 1 to 6 carbon atoms; R １２ are each independently an alkyl group having 1 to 6 carbon atoms; R １３ is an alkyl group having 1 to 6 carbon atoms, and x represents the number of repetitions, the number average value being 20 or more.

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 above general formula (a1-1), R １１ are each independently an alkyl group having 1 to 6 carbon atoms; R １２ are each independently an alkyl group having 1 to 6 carbon atoms; R １３ is an alkyl group having 1 to 6 carbon atoms, x represents the number of repetitions, the number average value of which is 20 or more, R １５ is a hydrogen atom or a methyl group; L １ is a divalent organic group.

4. The leveling agent according to claim 1 or 2, wherein the polymerizable monomer (a2) is 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 selected from the group consisting of a compound represented by the following general formula (a2-1), a compound represented by the following general formula (a2-2), a compound represented by the following general formula (a2-3), and a compound represented by the following general formula (a2-4): (In the above general formulae (a2-1), (a2-2), (a2-3) and (a2-4), R ２１ is a hydrogen atom or a methyl group, R ２２ is an alkyl group having 1 to 18 carbon atoms; R ２３ is a hydrogen atom or a methyl group, R ２４ is a hydrogen atom or an alkyl group having 1 to 18 carbon atoms; R ２５ is a hydrogen atom or a methyl group, R ２６ 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 is a hydrogen atom or a methyl group; R ２８ 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 is a divalent organic group or a single bond, n is an integer ranging from 1 to 4, m is the number of repetitions, the number average value of m is in the range of 1 to 200, p is an integer ranging from 1 to 10, q is the number of repetitions, and the number average value of q is in the range of 1 to 100.

6. The leveling agent according to claim 1 or 2, wherein the proportion of the polymerizable monomer (a1) in the polymerization components is in the range of 25 to 50 mass %.

7. The leveling agent according to claim 1 or 2, wherein 80 mass % or more of the polymerization components are the polymerizable monomer (a1) and the polymerizable monomer (a2).

8. The leveling agent according to claim 1 or 2, wherein the silicone chain-containing polymer does not contain a fluorine atom.

9. The leveling agent according to claim 1 or 2, wherein the weight average molecular weight of the silicone chain-containing polymer is 15,000 or more.

10. A resist composition comprising the leveling agent according to claim 1 or 2.

11. A polarizing plate comprising the leveling agent according to claim 1 or 2.

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