JP7844838B2 - Antistatic curable composition, cured product, laminate, polarizer protective film, and polarizer plate - Google Patents

Description

The present invention relates to a curable composition. More specifically, the present invention relates to a curable composition suitable as a high refractive index hard coat material for anti-reflective films.

Generally, displays are used in environments where ambient light, such as indoors or outdoors, is incident. This incident light is specularly reflected off the display surface, and the resulting reflected image mixes with the displayed image, degrading the screen display quality. Therefore, it is required to provide anti-reflective properties to the display surface.
Furthermore, the display surface is required to have antistatic properties to prevent contamination from dust and other particles, as well as to prevent static electricity on the display surface from affecting the inside of the display.

Generally, anti-reflective properties are achieved by forming a multilayer anti-reflective layer on a transparent substrate using a layered structure of alternating high-refractive-index and low-refractive-index layers made of metal oxides such as ITO, carbon, or thiophene-based conductive polymers. Furthermore, materials using metal oxides, carbon, or thiophene-based conductive polymers can also be given antistatic properties, allowing for the formation of an antistatic high-refractive-index layer. For example, Patent Document 1 describes the use of conductive particles in the high-refractive-index layer. However, this technique has the problem that transparency is compromised by the use of conductive particles.

Regarding coating materials for forming high refractive index layers, in recent years, organic coating materials mainly composed of high refractive index acrylic compounds having an aromatic ring structure have been proposed as an alternative to inorganic high refractive index coating materials such as ITO. With this acrylic coating material, it is possible to form a high refractive index hard coat layer that has a high refractive index, excellent transparency, and high surface hardness because it is acrylic. However, because acrylic materials have high insulating properties, this acrylic high refractive index hard coat layer has the disadvantage of being prone to static charge.

On the other hand, Patent Document 2 proposes an acrylic polymer having a quaternary ammonium base as an acrylic material that can impart antistatic properties, and it is disclosed that this acrylic polymer can provide both transparency and antistatic function.

Japanese Patent Publication No. 2010-217873 Japanese Patent Publication No. 2015-069058 Japanese Patent Publication No. 2016-088943

However, while the curable composition described in Patent Document 2 contains an acrylic monomer having a quaternary ammonium base effective in imparting antistatic properties, it is difficult to achieve both antistatic properties and a high refractive index when applying it to a coating material mainly composed of a commonly known high refractive index acrylic compound having an aromatic ring structure.
Furthermore, the acrylic polymer having a quaternary ammonium base described in Patent Document 3 had a problem in that, unless the Sp value of the acrylic polymer having the quaternary ammonium base was adjusted each time to match the high refractive index acrylic compound having an aromatic ring structure, the compatibility between the acrylic polymer having the quaternary ammonium base and the high refractive index acrylic compound having an aromatic ring structure was poor, resulting in a significant loss of transparency.

Accordingly, the present invention aims to provide a curable composition capable of forming a high refractive index hard coat layer with excellent antistatic properties and transparency, a polarizer protective film comprising a laminate having a hard coat layer made of a cured product of the curable composition on the surface of a base film, and a polarizer plate formed by laminating this polarizer protective film onto a polarizer.

The aforementioned problems are solved by the present invention. That is, the gist of the present invention is as follows: [1] to [13]
It is located in [ ].

[1] A curable composition characterized by containing two or more of the following components (A) and component (B).
[1] The curable composition according to [1], wherein component (A): a compound having at least an aromatic ring structure and a (meth)acryloyl group and having a refractive index of 1.50 to 1.70; component (B): a (meth)acrylic polymer containing an ionic group in its molecule [2], and at least one of component (A) has a structure selected from the group consisting of a diphenylmethane structure, a fluorene structure, a carbazole structure, and a biphenyl structure.
[3] The curable composition according to [1] or [2], wherein at least one of the components (A) is an acrylic acid adduct (A1) of bisphenol A diglycidyl ether.
[4] The curable composition according to [3], wherein the proportion of (A1) is 5 to 55% by weight with respect to the total mass of all constituent units that make up component (A).
[5] The curable composition according to any one of [1] to [4], wherein component (B) is a (meth)acrylic polymer containing a structural unit in its molecule derived from a compound represented by the following formula (1).
_CH2 =C( ^R1 )-C(O) ^-Q1- ( _CH2 ) _m -N ^{+ R2R3R4 ・ X-... (} 1)
(In formula (1), ^R1 represents a hydrogen atom or a methyl group, ^R2 and ^R3 each independently represent a hydrocarbon group having 1 to 24 carbon atoms, and ^R4 represents a hydrogen atom, a hydrocarbon group having 1 to 24 carbon atoms, or -C
_H₂ - ^CH (OH ^{) -CH₂ -} _N₁₁ ^{+ R₅ R₆ Rₙ ・ Y₁}
[6] The mass-average molecular weight of component (B) is 1,000 or more and 100,000 or less. [1] to [5]
A curable composition according to any one of the items in the ].
[7] The curable composition according to [5] or [6], wherein component (B) is a (meth)acrylic polymer containing 10 to 90% by weight of structural units derived from the compound represented by formula (1) in the molecule, based on the total mass of all structural units constituting component (B).
[8] The total amount of component (A) and component (B) is 1 to 99% by weight of component (B) [
A curable composition according to any one of items [1] to [7].
[9] A curable composition according to any one of [1] to [8], comprising a component (C) that does not contain an aromatic ring structure and has one or more (meth)acryloyl groups.
[10] A curable composition according to any one of [1] to [9], containing a polymerization initiator.
A laminate in which a hard coat layer made of a cured product of any one of the curable compositions described in [11] [1] to [10] is laminated on only one side of a substrate.
A polarizer protective film comprising the laminate described in [12] and [11].
A polarizing plate obtained by laminating the side of the polarizer protective film described in [13] and [12] that does not have a hard coat layer to a polarizer.

According to the present invention, it is possible to provide a curable composition that can form a high refractive index hard coat layer with excellent antistatic properties and transparency, a polarizer protective film made of a laminate having a hard coat layer made of a cured product of the curable composition on the surface of a base film, and a polarizer plate made by laminating the polarizer protective film onto a polarizer.

Embodiments of the present invention will be described in detail below, but the following description is merely one example of an embodiment of the present invention, and the present invention is not limited to the following description unless it exceeds the gist of the invention. In this specification, when the expression "~" is used, it is used to include the numerical value or physical property value before and after it. In this invention, when the expression "(meth)acrylic" is used, it means either or both "acrylic" and "methacrylic". The same meaning applies to "(meth)acryloyl" and "(meth)acrylate".

[Curable composition]
The curable composition of the present invention is characterized by containing two or more of the following components (A) and component (B).
Component (A): A compound having at least an aromatic ring structure and a (meth)acryloyl group, and having a refractive index of 1.50 to 1.70. Component (B): 10 to 90 structural units in the molecule derived from the compound represented by the following formula (1).
The (meth)acrylic polymer containing ⁽ weight %) _CH₂ = C( ^R₁ )-C(O) ^-Q₁- ( _CH₂ ) _m -N ^{+ R₂R₃R₄ · X-} …(1)
(In formula (1), ^R1 represents a hydrogen atom or a methyl group, ^R2 and ^R3 each independently represent a hydrocarbon group having 1 to 24 carbon atoms, and ^R4 represents a hydrogen atom, a hydrocarbon group having 1 to 24 carbon atoms, or -C
_H₂ - ^CH (OH ^{) -CH₂ -} _N₁₁ ^{+ R₅ R₆ Rₙ ・ Y₁}
This curable composition may further contain, if necessary, component (C), a polymerization initiator, and an organic solvent.
This curable composition may further contain other components not listed above, if necessary.

In the following, the compound represented by formula (1) above may be referred to as "compound (1)," and other compounds may be referred to as "compound (2)."
Furthermore, structural units derived from compound (1) are sometimes referred to as "structural unit (1)," and structural units derived from compound (2) are sometimes referred to as "structural unit (2)."

[Ingredient (A)]
Component (A) of the composition of the present invention is a compound having at least an aromatic ring structure and a (meth)acryloyl group, and having a refractive index of 1.50 to 1.70.

If the refractive index of compound (A) is lower than 1.50, the desired high refractive index cannot be obtained. From the viewpoint of high refractive index, the refractive index of compound (A) is preferably 1.51 or higher, and more preferably 1.52 or higher. From the viewpoint of high refractive index, a higher refractive index of compound (A) is preferable, but the upper limit of the refractive index as an organic compound is usually 1.7.
It is approximately 0.
The refractive index of component (A) of the present invention is the refractive index of the compound alone in its uncured state, and the refractive index of component (A) is as described in the Examples section below.

Component (A) may be any compound having an aromatic ring structure and a (meth)acryloyl group, and having a refractive index of 1.50 to 1.70, as described above, and may be a monomer or a polymer. Furthermore, the compound may have two or more aromatic ring structures, in which case the two or more aromatic ring structures may be identical or different. The (meth)acryloyl group may also be present as a single group or as two or more groups.

Component (A) has an aromatic ring structure as the structural part responsible for its high refractive index. There are no particular restrictions on the aromatic ring structure, but examples include the following structure. There are no particular restrictions on the type or number of substituted functional groups for the aromatic ring structures exemplified below. In the following, "Ph" represents a phenyl group.

Among these aromatic ring structures, the diphenylmethane structure, fluorene structure, and carbazole structure are particularly preferred from the viewpoint of high refractive index because they have high electron density and readily exhibit high refractive index, and the biphenyl structure is also preferred because it has high electron density and readily exhibits high refractive index. More preferred aromatic ring structures are the diphenylmethane structure, fluorene structure, and biphenyl structure.

<Acrylate adduct of bisphenol A diglycidyl ether (A1)>
In particular, the acrylic acid adduct (A1) of bisphenol A diglycidyl ether having a diphenylmethane structure has good compatibility with component (B) and contributes to the transparency of the cured layer; therefore, the curable composition of the present invention preferably contains at least (A1).
When all components other than (A1) in component (A) are designated as (A2), the proportion of (A1) in the total amount of these components is preferably 5 to 55% by weight, more preferably 10 to 50% by weight, and particularly preferably 20 to 40% by weight. A higher proportion tends to improve the transparency of the cured layer, while a lower proportion tends to improve the antistatic properties.

[Component (B)]
Component (B) of the composition of the present invention is a (meth)acrylic polymer containing ionic groups in its molecule, and contributes to the antistatic properties of the cured layer.

Component (B) is a (meth)acrylic polymer containing 10 to 90% by weight of structural units (1) derived from compound (1) represented by the following formula (1) in its molecule, relative to the total mass of all constituent units of component (B).
<Compound (1)>
Compound (1) is represented by the following formula (1) and is a component that contributes to antistatic properties.
_CH2 =C( ^R1 )-C(O) ^-Q1- ( _CH2 ) _m -N ^{+ R2R3R4 ・ X-... (} 1)
(In formula (1), ^R1 represents a hydrogen atom or a methyl group, ^R2 and ^R3 each independently represent a hydrocarbon group having 1 to 24 carbon atoms, and ^R4 represents a hydrogen atom, a hydrocarbon group having 1 to 24 carbon atoms, or -C
_H₂ - ^CH (OH ^{) -CH₂ -} _N₁₁ ^{+ R₅ R₆ Rₙ ・ Y₁}

In the above formula (1), ^R1 is a hydrogen atom or a methyl group, preferably a methyl group.
^R2 and ^R3 are each independently hydrocarbon groups having 1 to 24 carbon atoms. Examples of hydrocarbon groups include alkyl groups, cycloalkyl groups, aryl groups, and aralkyl groups.
^4. The same applies to the hydrocarbon groups ^R5 to ^R7 .
^R2 and ^R3 are each preferably a methyl group or an ethyl group, with a methyl group being more preferred.
^R4 is preferably a methyl group, an ethyl group, or a butyl group, with a methyl group being more preferred.
^R5 to ^R7 are each independently preferably methyl or ethyl groups, with methyl groups being more preferred.

The anions represented by ^X- and ^Y- are, independently, chloride ions and iodine ions,
Halide ions such as bromide ions, hexafluorophosphate ions ( ^PF6- ),
Tetrafluoroborate ions ( ^BF₄- ) or sulfate ions are preferred, and among these, halide ions are preferred due to their good antistatic properties, and chloride ions are more preferred due to the relative ease of obtaining raw materials and synthesis.
^Q1 is preferably O (oxygen atom), m is preferably an integer from 1 to 5, and more preferably 3.

Compound (1) specifically includes N,N-dimethylaminoethyl (meth)acrylate methyl chloride, N-(meth)acryloyloxyethyl-N,N,N-trimethylammonium chloride, N-(meth)acryloyloxypropyl-N,N,N-trimethylammonium chloride, N-(meth)acryloyloxyethyl-N-ethyl-N,N-dimethylammonium = monoethyl sulfate, N-(meth)athaliroyloxyethyl-N,N,N-triethylammonium = monoethyl sulfate, N-[3-{N,-
(meth)acryloyloxyethyl-N',N,-dimethylammonium}-2-hydroxypropyl]-N,N,N-trimethylammonium chloride, N-[3-{N'-
(meth)acryloyloxyethyl-N',N,-diethylammonium}-2-hydroxypropyl]-N,N,N-triethylammonium chloride and other cationic (meth)acrylic esters; N-(meth)acryloylaminopropyl-N,N,
N-trimethylammonium chloride, N-(meth)acryloylaminopropyl-N
, N-diethyl-N-methylammonium chloride, N-(meth)acryloylaminopropyl-N-ethyl-N,N-dimethylammonium chloride, N-(meth)acryloylaminopropyl-N,N,N-trimethylammonium monosulfate, N-(meth)acryloylaminopropyl-N,N-diethyl-N-methylammonium monosulfate, N-(meth)acryloylaminopropyl-N-ethyl-N,N-dimethylammonium monosulfate, N-[3-{N'-(meth)acryloylaminopropyl-N',N
Examples include (meth)acrylamides having cationic groups such as '-diethylammonium'-2-hydroxypropyl-N,N,N-trimethylammonium chloride.

Among these, N-(meth)acryloyloxyethyl-N,N,N-trimethylammonium chloride, N-(meth)acryloyloxypropyl-N,N,N-trimethylammonium chloride, and N-(meth)acryloylaminopropyl-N,N,N-trimethylammonium chloride are preferably used, with N-(meth)acryloyloxyethyl-N,N,N-trimethylammonium chloride and N-(meth)acryloylaminopropyl-N,N,N-trimethylammonium chloride being particularly preferred.

The (meth)acrylic polymer of component (B) may contain only one of the above structural units (1), or it may contain two or more.

<Compound (2)>
The (meth)acrylic polymer of component (B) contains, in addition to the structural unit (1) derived from compound (1) above, structural unit (2) derived from compound (2) in an amount of 10 to 90% by weight relative to the total mass of all structural units constituting component (B). Compound (2) is composed of component (A) and component (
This component enhances compatibility with B) and contributes to improving the transparency of the cured layer.

Examples of compound (2) include alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, and tridecyl (meth)acrylate; (meth)acrylic acid esters of the above amino alcohols; hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and hydroxybutyl (meth)acrylate; benzyl (meth)acrylate,
Cyclohexyl (meth)acrylate, Isobornyl (meth)acrylate, Dicyclopentenyl (meth)acrylate, Dicyclopentenyloxyethyl (meth)acrylate, Ethoxyethyl (meth)acrylate, Ethyl carbitol (meth)acrylate, Butoxyethyl (meth)acrylate, Cyanoethyl (meth)acrylate, Glycidyl (
Various (meth)acrylates such as meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, N,N-diethylaminopropyl (meth)acrylate, N,N-dimethyl (meth)acrylamide, N,N-diethyl (meth)acrylamide, N,N-dipropyl (meth)acrylamide, N,N-di-n-butyl (meth)acrylamide, N,N-diisobutyl (meth)acrylamide, N,N-di-t-butyl (meth)acrylamide, N,N-dipentyl (meth)acrylamide, N,N-dicyclohexyl (meth)acrylamide, N,N-di-2-ethylhexyl (meth)acrylamide, N,N-didodecyl (meth)acrylamide, N,N-ditridecyl (meth)
Acrylamide, N,N-dioctadecyl(meth)acrylamide, N-ethyl-N-methyl(meth)acrylamide, N-methyl-N-propyl(meth)acrylamide, N-
n-butyl-N-methyl(meth)acrylamide, N-methyl-N-octyl(meth)acrylamide, N-dodecyl-N-methyl(meth)acrylamide, N-methyl-N-octadecyl(meth)acrylamide, N-ethyl-N-propyl(meth)acrylamide, N,N-dimethylaminoethyl(meth)acrylamide, N,N-diethylaminoethyl(meth)acrylamide, N,N-dimethylaminopropyl(meth)acrylamide, N
Examples include various (meth)acrylamides such as N-diethylaminopropyl(meth)acrylamide, styrene, methylstyrene, etc. These may be used individually or in combination of two or more. Among these, polymerizable monomers having an amino group are component (A).
This is preferable because it can improve compatibility with component (B) and enhance the transparency of the cured layer.
Examples of polymerizable monomers having such amino groups include N,N-dimethylaminoethyl (meth)acrylate and N,N-diethylaminoethyl (meth)acrylate.
Furthermore, among these, polymerizable monomers having highly hydrophobic long-chain alkyl groups are component (B).
It is preferable because it can be segregated at the air interface of the cured layer to enhance the antistatic properties of the cured layer. Examples of polymerizable monomers having such long-chain alkyl groups include stearyl(meth)
Examples include acrylate, lauryl (meth)acrylate, and tridecyl (meth)acrylate.

The ratio of compound (1) in component (B) to the total mass of all constituent units of component (B) is preferably 10 to 90% by weight, more preferably 20 to 80% by weight, and even more preferably 30 to 70% by weight. A higher ratio tends to result in higher antistatic properties, while a lower ratio tends to improve the transparency of the cured layer.

The weight-average molecular weight (Mw) of the (meth)acrylic polymer in component (B) is 1,000 or more, from the viewpoint of suppressing bleed-out in the coating film and improving the durability of antistatic properties.
Preferably, it is 5,000 or more, and more preferably 10,000 or more. Furthermore, from the viewpoint of compatibility with other components, it is 100,000 or less, more preferably 80,000 or less, and even more preferably 60,000 or less.
In this invention, the weight-average molecular weight (Mw) of component (B) is a polystyrene-based value measured by gel permeation chromatography (GPC), and is specifically measured by the method described in the Examples section below.

Component (B) can be produced by a radical polymerization reaction using the above-mentioned raw material monomers. The radical polymerization reaction is preferably carried out in an organic solvent in the presence of a radical polymerization initiator.

Organic solvents used in radical polymerization reactions include, for example, ketone solvents such as acetone and methyl ethyl ketone (MEK); ethanol, methanol, and isopropyl alcohol (IP).
A) Examples include alcohol-based solvents such as isobutanol; ether-based solvents such as ethylene glycol dimethyl ether and propylene glycol monomethyl ether; ester-based solvents such as ethyl acetate, propylene glycol monomethyl ether acetate, and 2-ethoxyethyl acetate; and aromatic hydrocarbon solvents such as toluene. These organic solvents may be used individually or in combination of two or more.

Examples of radical polymerization initiators used in radical polymerization reactions include organic peroxides such as benzoyl peroxide and di-t-butyl peroxide; 2,2'-azobisbutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(
Examples include azo compounds such as 4-methoxy-2,4-dimethylvaleronitrile. These radical polymerization initiators may be used individually or in combination of two or more. It is preferable to use the radical polymerization initiator in an amount of 0.01 to 5 parts by weight per 100 parts by weight of the total raw material monomers.

Furthermore, during radical polymerization reactions, chain transfer agents can be used to control the weight-average molecular weight of component (B). Examples of chain transfer agents include butanethiol, octanthiol, decanethiol, dodecanethiol, hexadecanethiol, octadecanethiol, cyclohexyl mercaptan, thiophenol, octyl thioglycolate, and 2
- Octyl mercaptopropionate, 3-Octyl mercaptopropionate, 2-ethylhexyl mercaptopropionate, 2-ethylhexyl thioglycolate, butyl-3-mercaptopropionate, mercaptopropyltrimethoxysilane, methyl-
3-mercaptopropionate, 2,2-(ethylenedioxy)diethanethiol, ethanethiol, 4-methylbenzenethiol, 2-mercaptoethyl octanoate,
1,8-Dimercapto-3,6-Dioxaoctane, Decantrichol, Dodecylmercaptan, Diphenyl sulfoxide, Dibenzyl sulfide, 2,3-Dimethylcapto-
Examples include thiol compounds such as 1-propanol, mercaptoethanol, thiosalicylic acid, thioglycerol, thioglycolic acid, 3-mercaptopropionic acid, thiomalic acid, mercaptoacetic acid, mercaptosuccal acid, and 2-mercaptoethanesulfonic acid. These may be used individually or in combination of two or more.

The amount of chain transfer agent used is preferably 0.1 to 25 parts by weight, more preferably 0.5 to 20 parts by weight, and even more preferably 1.0 to 15 parts by weight, per 100 parts by weight of the total raw material monomers.

The reaction time for the radical polymerization reaction is preferably 1 to 20 hours, and more preferably 3 to 12 hours. The reaction temperature is preferably 40 to 120°C, and more preferably 50 to 100°C.

[Content ratio of ingredient (A) and ingredient (B)]
The curable composition of the present invention contains component (B) in an amount of 1 to 99% by weight relative to the total amount of component (A) and component (B). Component (B) functions as an additive for imparting antistatic properties, and good antistatic properties can be obtained by including component (B) in an amount of 1% by weight or more relative to the total amount of component (A) and component (B). From the viewpoint of antistatic properties, the curable composition of the present invention preferably contains component (B) in an amount of 2% by weight or more, more preferably 3% by weight or more, and even more preferably 5% by weight or more, relative to the total amount of component (A) and component (B).
On the other hand, by ensuring that the content of component (B) in the curable composition of the present invention is 99% by weight or less relative to the total amount of component (A) and component (B), it is possible to obtain a curable composition with a high refractive index by ensuring a sufficient content of component (A), which is a high refractive index compound. From the viewpoint of high refractive index, the curable composition of the present invention preferably contains component (B) at 80% by weight or less, more preferably at 60% by weight or less, and even more preferably at 40% by weight or less, relative to the total amount of component (A) and component (B).

[Component (C)]
In addition to components (A) and (B), the curable composition of the present invention preferably contains 1 to 99 parts by weight of component (C) described below, per 100 parts by weight of the total amount of components (A), (B), and (C), in addition to components (A) and (B), in terms of curability, hardness of the cured film, and scratch resistance.
Component (C): A compound that does not contain an aromatic ring structure and has one or more (meth)acryloyl groups.

Component (C) may be any compound having one or more (meth)acryloyl groups and not containing an aromatic ring structure, and may be a monofunctional (meth)acrylate compound or a bifunctional or polyfunctional (meth)acrylate compound.

Examples of monofunctional (meth)acrylate compounds include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, t-butyl (meth)acrylate, glycidyl (meth)acrylate, acryloylmorpholine, N-vinylpyrrolidone, tetrahydrofluryl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate,
Isobornyl (meth)acrylate, isodecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, cetyl (meth)acrylate, stearyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethyl carbitol (meth)acrylate, phosphate (meth)acrylate, ethylene oxide modified phosphate (meth)acrylate, methoxydiethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, Examples include toxypropylene glycol (meth)acrylate, dimethylaminoethyl (meth)acrylate, trifluoroethyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, hexafluoropropyl (meth)acrylate, octafluoropropyl (meth)acrylate, octafluoropropyl (meth)acrylate, adamantane derivative mono(meth)acrylate such as adamantyl acrylate having a monovalent mono(meth)acrylate derived from 2-adamantane and adamantanediol.

Examples of difunctional (meth)acrylate compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, butanediol di(meth)acrylate, hexanediol di(meth)acrylate, nonanediol di(meth)acrylate, ethoxylated hexanediol di(meth)acrylate, propoxylated hexanediol di(meth)acrylate, diethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, ethoxylated neopentyl glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, and hydroxypivalate neopentyl glycol di(meth)acrylate, among other di(meth)acrylates.

Examples of trifunctional or more (meth)acrylate compounds include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, tris-2-hydroxyethyl isocyanurate tri(meth)acrylate, glycerin tri(meth)acrylate, pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, succinic acid-modified pentaerythritol Trifunctional (meth)acrylate compounds such as tri(meth)acrylate, ditrimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, succinic acid-modified pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, ditrimethylolpropane penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate,
Ditrimethylolpropanehexa(meth)acrylate and other polyfunctional (meth) substances with three or more functions
Examples include acrylate compounds and polyfunctional (meth)acrylate compounds in which some of these (meth)acrylates are substituted with alkyl groups or ε-caprolactone; polyfunctional (meth)acrylates having nitrogen atom-containing heterocyclic structures such as isocyanurate structures; polyfunctional (meth)acrylates having highly branched resinous structures such as polyfunctional (meth)acrylates having dendrimer structures and polyfunctional (meth)acrylates having hyperbranched structures; and urethane (meth)acrylates in which hydroxyl-containing (meth)acrylates such as pentaerythritol tri(meth)acrylate, dipentaerythritol tri(meth)acrylate, and dipentaerythritol penta(meth)acrylate are added to isocyanates, triisocyanates, or isocyanurates.

Among these (meth)acrylate compounds, polyfunctional (meth)acrylate compounds are preferred because they allow for easy balancing of the physical properties of the resulting cured product, such as pentaerythritol tri(meth)acrylate and pentaerythritol tetra(
Meth)acrylate, pentaerythritol penta(meth)acrylate, pentaerythritol hexa(meth)acrylate, dipentaerythritol tri(meth)acrylate, dipentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, or acid-modified products thereof are preferred.

These components (C) may be used individually or in combination of two or more.

The curable composition of the present invention is, with respect to the total amount of component (A), component (B), and component (C),
The composition contains 1 to 99% by weight of component (C). By having a component (C) content of 1 part by weight or more per 100 parts by weight of the total of components (A), (B), and (C) in the curable composition of the present invention, the effects of improving curability, hardness of the cured film, scratch resistance, etc., due to the inclusion of component (C) can be effectively obtained. From these viewpoints, the curable composition of the present invention preferably contains 1 part by weight or more of component (C) per 100 parts by weight of the total of components (A), (B), and (C), and more preferably contains 2 parts by weight or more.
On the other hand, by having a content of component (C) of the curable composition of the present invention of 99 parts by weight or less per 100 parts by weight of the total amount of components (A), (B), and (C), high refractive index, antistatic properties, and transparency due to components (A) and (B) can be effectively obtained. From these viewpoints, the curable composition of the present invention preferably contains 85 parts by weight or less of component (C) per 100 parts by weight of the total amount of components (A), (B), and (C), and more preferably contains 70 parts by weight or less.

[Polymerization initiator]
The curable composition of the present invention preferably contains a polymerization initiator in order to improve curability by active energy rays.

As a polymerization initiator, a photopolymerization initiator is preferred, for example, 2-ethylanthraquinone.
Benzophenones consisting of 2,4-diethylthioxanthone, benzophenone and its derivatives, 1-hydroxycyclohexyl-phenyl-ketone [for example, trade name "Omni
rad(registered trademark) 184, manufactured by IGM, 2-hydroxy-1-{4-[4-(2-
Hydroxy-2-methyl-propionyl)-benzyl]phenyl}-2-methyl-propan-1-one [e.g., trade name "Omnirad® 127"], 2,2-dimethoxy-1,2-diphenylethane-1-one [e.g., trade name "Omnirad® 651", manufactured by IGM], 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide [e.g., trade name "Omnirad® TPO H", manufactured by IGM]
[Manufactured by IGM Inc.], bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide [e.g., trade name "Omnirad® 819", manufactured by IGM Inc.], 2-methyl-
1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one [for example,
Product name "Omnirad (registered trademark) 907", manufactured by IGM, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1 [For example, product name "Om
Examples include "nirad® 369" and 2-hydroxy-2-methyl-1-phenylpropan-1-one [for example, trade name "Omnirad® 1173," manufactured by IGM]. These polymerization initiators may be used individually or in combination of two or more. Among these, α-hydroxyketone compounds with excellent reactivity are preferred.
Examples of such compounds include 1-hydroxycyclohexylphenyl ketone [e.g., trade name "Omnirad® 184", manufactured by IGM].

From the viewpoint of enhancing curability, the content of the polymerization initiator is preferably 0.01 parts by weight or more, more preferably 0.05 parts by weight or more, and even more preferably 0.1 parts by weight or more, based on 100 parts by weight of the total of component (A), component (B), and component (C) used as needed. Furthermore, from the viewpoint of the stability of the curable composition, the content of the polymerization initiator is preferably 20
It is less than or equal to parts by weight, more preferably 10 parts by weight or less, and even more preferably 5 parts by weight or less.

[organic solvents]
The curable composition of the present invention typically contains an organic solvent and is prepared to a solid content concentration of approximately 5 to 95% by weight. A solid content concentration of 5% by weight or more is preferable from the viewpoint of preventing unintended curing reactions (such as gelation) of the curable composition, and a solid content concentration of 95% by weight or less is preferable from the viewpoint of coatability. From these viewpoints, the solid content concentration is more preferably 10% by weight or more.
More preferably, the solid content is 20% by weight or more, more preferably 90% by weight or less, even more preferably 85% by weight or less, and particularly preferably 80% by weight or less. In this invention, "solid content" refers to the components excluding the solvent, and includes not only solid components but also semi-solid and viscous liquid substances.

The organic solvent is not particularly limited, and the types of component (A), component (B), and component (C) used as needed, as well as the type of substrate used when forming the hard coat layer,
The appropriate choice can be made considering the method of application to the substrate, etc. Specific examples of organic solvents include:
For example, saturated hydrocarbon solvents such as n-hexane, n-heptane, n-octane, n-decane, n-dodecane, cyclohexane, and methylcyclohexane; aromatic solvents such as toluene and xylene; ketone solvents such as methyl ethyl ketone, acetone, methyl isobutyl ketone, and cyclohexanone; diethyl ether, isopropyl ether, tetrahydrofuran,
Dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether,
Examples include ether-based solvents such as propylene glycol monomethyl ether, anisole, and phenetol; ester-based solvents such as ethyl acetate, butyl acetate, isopropyl acetate, and ethylene glycol diacetate; amide-based solvents such as dimethylformamide, diethylformamide, and N-methylpyrrolidone; cellosolve-based solvents such as methyl cellosolve, ethyl cellosolve, and butyl cellosolve; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and butanol; and halogen-based solvents such as dichloromethane and chloroform.

These solvents may be used individually or in combination of two or more. Among these, ester solvents, ether solvents, alcohol solvents, and ketone solvents are preferred because they exhibit good compatibility with components (A) and (B).

[Other ingredients]
The curable composition of the present invention comprises components (A) and (B) to the extent that they do not impair the effects of the present invention.
The mixture may contain components other than component (C), polymerization initiators, and organic solvents. Examples of other components include ultraviolet absorbers, hindered amine light stabilizers, fillers, silane coupling agents, reactive diluents, antistatic agents other than component (B), organic pigments, slip agents, dispersants, thixotropy-imparting agents (thickeners), defoamers, antioxidants, leveling agents, inorganic particles, organic particles, photoacid generators, and the like.

[Method for producing a curable composition]
The method for producing the curable composition of the present invention is not particularly limited, but for example, components (A) and (B)
It can also be obtained by mixing component (C), polymerization initiator, organic solvent, and other components as needed. When mixing each component, it is preferable to mix them uniformly using a disperser, stirrer, or the like.

[Cured product/laminate]
A cured product of the present invention can be obtained by curing the curable composition of the present invention by irradiating it with active energy rays or the like. In particular, by applying the curable composition of the present invention onto a substrate or the like and curing it, a laminate can be formed on the substrate in which a cured layer made of the curable composition of the present invention is formed. Furthermore, by applying the curable composition of the present invention onto a substrate or the like in this way and curing it into a film, a hard coat film (high refractive index hard coat layer) can be obtained.
This can be obtained. Furthermore, by applying the curable composition of the present invention onto another resin film as a base material and curing it to form a hard coat film, a film laminate can be obtained in which a high refractive index hard coat film is laminated on another resin film. In this invention, the term "coating" is used to include what is generally called "coating process".

Examples of substrates used in the above-mentioned laminate include organic materials such as plastic substrates and inorganic materials such as metal substrates and glass substrates, but the cured product obtained by curing the curable composition of the present invention is
Because it has excellent transparency, it is preferable to apply it to a transparent substrate. As a plastic substrate, various synthetic resins, for example, acrylonitrile-butadiene-styrene copolymer (A
BS resin, polycarbonate (PC) resin, polyethylene terephthalate (PET) resin, polybutylene terephthalate (PBT) resin, polymethyl methacrylate (PMMA)
Examples include resins such as polystyrene (PS) resin, polyolefin resin, and cellulose resin. While there are no particular limitations on the metal substrate, examples include hot-rolled and cold-rolled steel sheets, hot-dip galvanized steel sheets, electro-galvanized steel sheets, tinplate, tin-free steel, various other platings, or alloy-plated steel sheets, stainless steel sheets, and aluminum sheets. Furthermore, these may be subjected to various surface treatments such as phosphate treatment, chromate treatment, organic phosphate treatment, organic chromate treatment, and heavy metal substitution treatments such as nickel. As the glass substrate, in addition to ordinary glass, various chemically treated glass (for example, Corning's Gorilla Glass® and AGC's DragonTrail®) or multi-component glass may be used. The curable composition of the present invention is a plastic substrate.
It is suitable for glass substrates, and particularly suitable for plastic substrates.

The hard coat layer (high refractive index layer) formed on the substrate can be formed, for example, by applying (coating) the curable composition of the present invention onto the substrate and irradiating it with active energy rays. Methods for applying (coating) the curable composition of the present invention onto the substrate include, for example, the reverse coat method, the gravure coat method, the rod coat method, the bar coat method, the Meyer bar coat method, and
Examples include die coating and spray coating methods. Furthermore, the form of the cured product of the present invention is not particularly limited, but typically, a cured product obtained by curing on a substrate by irradiation with active energy rays can be obtained as a cured film (cured coating) on at least one side of the substrate.

The active energy rays that can be used to cure the curable composition of the present invention include ultraviolet rays, electron beams, X-rays, infrared rays, and visible light. Of these active energy rays, ultraviolet rays and electron beams are preferred from the viewpoint of curability and prevention of resin degradation.

When curing the curable composition of the present invention by ultraviolet irradiation, various ultraviolet irradiation devices can be used, and as light sources, xenon lamps, high-pressure mercury lamps, metal halide lamps, LED-UV lamps, excimer lamps, etc., can be used. The amount of ultraviolet irradiation (unit: mJ/ ^cm² ) is usually 10 to 10,000 mJ/ ^{cm², and preferably 100 to 5,000 mJ/cm²} from the viewpoint of curability of the curable composition of the present invention and flexibility of the cured product (cured film).
The concentration is mJ/ ^cm² , and more preferably 200 to 3,000 mJ/ ^cm² .

Furthermore, when curing the curable composition of the present invention by electron beam irradiation, various electron beam irradiation devices can be used. The electron beam irradiation dose (Mrad) is typically 0.5 to 20 Mrad.
Therefore, from the viewpoint of curability of the curable composition of the present invention, flexibility of the cured product, and prevention of damage to the substrate, it is preferably 1 to 15 Mrad.

[Application]
The cured product obtained from the curable composition of the present invention has a high refractive index, excellent antistatic properties, and transparency, making it useful as a hard coat layer (high refractive index layer) for optical films such as anti-reflective films. While there are no particular restrictions on the thickness of the cured film made from the curable composition of the present invention when used as a high refractive index layer, it is typically about 1 to 20 μm, and preferably 1 to 10 μm.

The thickness of the substrate is arbitrary. If the substrate is in the form of a film, its thickness is preferably 5 μm or more and 3 mm or less, more preferably 10 μm or more and 2 mm or less, even more preferably 15 μm or more and 1 mm or less, and particularly preferably 20 μm or more and 250 μm or less.

Furthermore, the thickness of the laminate is also arbitrary. In the case of a film-like laminate, since each layer needs to fully perform its respective function, the thickness of the laminate is preferably 6 μm or more, more preferably 10 μm or more, and even more preferably 15 μm or more. Also, from the point of view of the need for thinner and lighter products to which the laminate is applied, the thickness of the laminate is preferably 3 mm or less, more preferably 2 mm or less, even more preferably 1 mm or less, and particularly preferably 300 μm or less.

A laminate in which the cured layer of the composition of the present invention is laminated on a substrate as a hard coat layer exhibits excellent adhesion between the substrate and the hard coat layer, as well as surface hardness. For this reason, the laminate is suitable for liquid crystal televisions,
It can be suitably used as a surface cover for a wide range of items, including optical display components for OLED TVs, electronic paper, touch panels, smartphones, etc.; automotive parts such as lamp-related items and window-related items (rear windows, side windows, skylights, etc.); and household goods such as housings for various electrical equipment, decorative panels, and furniture. Among these, it is particularly suitable as an optical display component, and especially suitable for use as a polarizer protective film and display protective film, which are bonded to polarizers in the manufacture of polarizing plates for displays.

[Polarizer protective film, polarizing plate]
The polarizer protective film of the present invention has a hard coat layer made of a cured product of the composition of the present invention,
The polarizer plate of the present invention consists of a laminate formed by laminating a plastic film on only one side. Furthermore, the polarizer plate of the present invention is formed by attaching the side of the polarizer protective film that does not have a hard coat layer to a polarizer. The polarizer protective film can be attached to one or both sides of the polarizer. Adhesives or other adhesives can be used for attachment.

Optical films such as anti-reflective films having a high refractive index hard coat layer made of the cured product of the present invention are suitable as optical films to be provided on the surface of displays such as liquid crystal displays. By providing an optical film having a high refractive index hard coat layer made of the cured product of the present invention on the surface of a display such as a liquid crystal display, a display surface with excellent visibility and resistance to dirt such as dust can be obtained due to its excellent transparency, antistatic properties, and anti-reflective function.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist of the invention. The various manufacturing conditions and evaluation result values in the following examples are intended to represent preferred upper or lower limits in embodiments of the present invention, and the preferred range may be defined by a combination of the aforementioned upper or lower limits and the values of the following examples or the values of the examples themselves.

[Evaluation Method]
In the following examples and comparative examples, the cured film was evaluated using the following method.

<Antistatic properties: Surface resistance value>
After the cured film was allowed to settle for 24 hours in a constant temperature room at 23°C and 50% RH, it was then subjected to a high-resistivity resistivity meter (Mitsubishi Chemical Analytec "High Resistar UP MCP-HT4") in the same constant temperature room.
The surface resistivity was measured after applying a voltage of 500V using a 50" material, and this was used as an indicator of antistatic properties. A smaller surface resistivity indicates better antistatic properties.

<Transparency: Haze>
For the cured film, a haze meter (manufactured by Nippon Denshoku Kogyo Co., Ltd.) is used in accordance with JIS K-7136.
The haze value was measured using a spectroscopic haze meter (SH7000).
The evaluation criteria were as follows, with ◎ to △ being considered acceptable.
◎: 2.0% or less ○: 2.1-10.0%
△: 10.1-20.0%
×: 20.1% or more

<Hardness: Pencil hardness>
For the hardened layer side of the laminate, a JIS-compliant pencil hardness tester was used to determine the hardness of the surface according to JIS K-540.
The pencil hardness was measured to determine the level at which no scratches occurred under a load of 500g, with 0 being the baseline. A pencil hardness of F or higher is preferable considering its use in various applications.

<Refractive index>
The refractive index of component (A) was measured by the following method.
Measurements were performed using an ATAGO DR-M2 multi-wavelength Abbe refractometer at a measurement temperature of 25°C. A refractive index of 1.55 or higher is preferable considering its use in various applications.

[Weight-average molecular weight (Mw) of component (B)]
The weight-average molecular weight (Mw) of an acrylic polymer (P) is determined by gel permeation chromatography (
The measurement was performed using GPC "HLC-8120" (manufactured by Tosoh Corporation). The column used was:
TSKgel G5000HXL*GMHXL-L (manufactured by Tosoh Corporation) was used. In addition, standard polystyrene F288/F80/F40/F10/F4/F1/A500 were used.
Calibration curves were created using 0/A1000/A500 (manufactured by Tosoh Corporation) and styrene.
The measurement was performed using a solution 10 in which the polymer was dissolved in tetrahydrofuran to a concentration of 0.4%.
The procedure was performed using 0 μl at a column oven temperature of 40°C. The weight-average molecular weight (Mw) was calculated on a standard polystyrene basis.

[Ingredient (A)]
The following commercially available product was used as component (A). The refractive index values were all referenced from the manufacturer's catalog. Note that (a-1) corresponds to (A1) mentioned above, and (a-2) and (a-3) correspond to (A2).

(a-1)
Miwon Miramer PE210
Bisphenol A epoxy diacrylate Refractive index: 1.558

(a-2)
Miwon Miramer M240
Ethoxylated bisphenol A diacrylate Refractive index: 1.537

(a-3)
・Manufactured by Shin Nakamura Chemical Co., Ltd. A-LEN-10T
Compounds having a biphenyl structure and an acryloyl group. Refractive index: 1.577

[Component (B)]
As component (B), an acrylic polymer was prepared as follows. The raw materials used and their abbreviations are as follows.
<Compound (1)>
DQ-100: Quaternary compound of N,N-dimethylaminoethyl methacrylate with methyl chloride (Kyoeisha Chemical Co., Ltd. "Light Ester (Registered Trademark) DQ-100")
<Compound (2)>
DMMA: N,N-dimethylaminoethyl methacrylate (manufactured by Mitsubishi Chemical Corporation as "Acryester® DM")
SLMA: A mixture of lauryl methacrylate and tridecyl methacrylate in a 45:55 (weight ratio) ratio (manufactured by Mitsubishi Chemical Corporation as "Acryester® SL").

(b-1)
In a reactor equipped with a stirrer, reflux condenser, and thermometer, add DQ100: 18 parts by weight, S
LMA: 7.5 parts by weight, DMMA: 4.5 parts by weight, Methyl ethyl ketone (MEK): 20
Parts by weight of isopropyl alcohol (IPA): 50 parts by weight were charged, and after stirring began, the system was purged with nitrogen and the temperature was raised to 55°C. Then, 0.6 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) (Wako Pure Chemical Industries, Ltd. "V-65") was added, the temperature of the system was raised to 65°C and stirred for 3 hours, and then another 0.6 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) was added and stirred at 65°C for 3 hours. The temperature of the system was raised to 80°C, and 2
After stirring for a specified time, the mixture was cooled to room temperature to obtain a solution of polymer b-1. The composition of the reaction solution was polymer b-1/MEK/IPA = 30/20/50 (by weight).
The weight-average molecular weight (Mw) of polymer b-1 was 45,200.

[Component (C)]
The following commercially available product was used as ingredient (C).

(c-1)
・Aronix (registered trademark) M-510 manufactured by Toagosei Co., Ltd.
succinic acid modified mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate

(c-2)
Kayarad (registered trademark) DPHA, manufactured by Nippon Kayaku Co., Ltd.
A mixture of dipentaerythritol tetraacrylate and dipentaerythritol hexaacrylate.

(c-3)
- Mitsubishi Chemical Corporation's Shiko (registered trademark) UV7600B
A mixture of isophorone diisocyanate, a condensate of pentaerythritol triacrylate, and pentaerythritol tetraacrylate.

[Example 1]
As component (A), 5% by weight of "a-1" and 85% by weight of "a-2"; as component (B), 6.6% by weight of "b-1"; as component (C), 3.4% by weight of "c-2" (where "by weight" for components (A) to (C) refers to the weight percentage of solids); and as a polymerization initiator,
1-Hydroxycyclohexylphenyl-ketone (Omnirad® 184, manufactured by IGM, Inc. (abbreviated as Omn184 in the table)) 4 parts by weight (Component (A) to (
A mixture of C) (based on 100 parts by weight of solids) was prepared and diluted with a mixed solvent of n-butanol and methyl ethyl ketone in a 50:50 (weight ratio) ratio to obtain a curable composition with a solids content of 30% by weight.

The obtained curable composition was applied to a polyethylene terephthalate (PET) film (Cosmoshine® A4100, manufactured by Toyobo Co., Ltd., thickness: 188 μm) using a bar coater #14 to achieve a dry film thickness of 5 μm, and then heated and dried at 80°C for 2 minutes. The coating film of the curable composition was then exposed to a high-pressure mercury lamp light source manufactured by Iwasaki Electric Co., Ltd., "US5-X04"
Using "01", a cured film (high refractive index hard coat film) was obtained by irradiating the film with ultraviolet light at a UV irradiance of 120 mW/cm2, with an integrated light amount of 300 mJ/cm2 per pass, in two passes. The transparency, antistatic properties, hardness, and refractive index of this cured film were evaluated as described above. The results are shown in Table 1.

[Examples 2-6 and Comparative Examples 1-7]
As shown in Tables 1 and 2, each curable composition was obtained in the same manner as in Example 1, except that the composition of the curable composition was changed, and then a cured film was obtained. For each cured film, the transparency described above,
The antistatic properties, hardness, and refractive index were evaluated. The results are shown in Tables 1 and 2.

[Evaluation Results]
As can be seen from Tables 1 and 2, all of Examples 1 to 6 exhibited good transparency, antistatic properties, hardness, and refractive index. While all of Examples 1 to 6 had a refractive index of 1.55 or higher,
Comparative Example 1, which did not contain component (A), had a low refractive index. Comparative Examples 2-4, which did not contain component (B), had poor antistatic properties. Furthermore, when the total amount of component (A) was considered to be 100% by weight, Comparative Example 5, in which the proportion of (A1) was greater than 55% by weight, had poor antistatic properties, and Comparative Examples 6-7, in which the proportion of (A1) was less than 5% by weight, had poor transparency.

Claims (12)

It contains two or more of the following ingredients (A) and the following ingredient (B) ,
A curable composition in which at least one of component (A) is an acrylic acid adduct (A1) of bisphenol A diglycidyl ether .
Component (A): A compound having at least an aromatic ring structure and a (meth)acryloyl group, and having a refractive index of 1.50 to 1.70. Component (B): A (meth)acrylic polymer containing an ionic group in its molecule. The curable composition according to claim 1, wherein at least one of component (A) has a structure selected from the group consisting of a diphenylmethane structure, a fluorene structure, a carbazole structure , and a biphenyl structure. The curable composition according to claim 1 or 2 , wherein the proportion of (A1) is 5 to 55% by weight with respect to the total mass of all constituent units that make up component (A). The curable composition according to any one of claims 1 to 3 , wherein the mass-average molecular weight of component (B) is 1,000 or more and 100,000 or less. The curable composition according to any one of claims 1 to 4, wherein component (B) is a (meth)acrylic polymer containing a structural unit derived from a compound represented by the following formula (1) in its molecule.
CH ₂ = C(R ¹ )-C(O)-Q ¹ -(CH ₂ ) _{I understand} -N ⁺ R ² R ³ R ⁴ ・X ^- …(1)
(In formula (1), R ¹ R represents a hydrogen atom or a methyl group. ² and R ³ Each of these independently represents a hydrocarbon group having 1 to 24 carbon atoms, R ⁴ This is a hydrogen atom, a hydrocarbon group having 1 to 24 carbon atoms, or -CH ₂ -CH(OH)-CH ₂ -N ⁺ R ⁵ R ⁶ R ⁷ ・Y ^- Represents R ⁵ ~R ⁷ Each of these independently represents a hydrocarbon group having 1 to 24 carbon atoms. Q ¹ is O or NH. ^- and Y ^- Each of these independently represents an anion. m is an integer between 1 and 10. The curable composition according to claim 5, wherein component (B) contains a (meth)acrylic polymer that contains 10 to 90% by weight of structural units derived from a compound represented by formula (1) in its molecule, relative to the total mass of all structural units constituting component ( B ). A curable composition according to any one of claims 1 to 6, comprising 1 to 99% by weight of component (B) relative to the total amount of component (A) and component (B). A curable composition according to any one of claims 1 to 7, further comprising a component (C) that does not contain an aromatic ring structure and has one or more (meth)acryloyl groups. A curable composition according to any one of claims 1 to 8, further comprising a polymerization initiator. A laminate in which a hard coat layer, made of a cured product of the curable composition described in any one of claims 1 to 9, is laminated on only one side of a substrate. A polarizer protective film comprising the laminate described in claim 10. A polarizing plate obtained by laminating the side of the polarizer protective film described in claim 11 that does not have a hard coat layer to a polarizer.