Polymer compounds, compositions, optical films, and optical laminates

Abstract

To provide a polymer compound that is blended with an adherend, thereby improving the adhesion between the adherend and a hydrophilic member and also provide a composition including the polymer compound, an optical film and an optical laminate.SOLUTION: A polymer compound includes a repeat unit including a structure represented by the formula (1) in a side chain.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a polymer compound, a composition, an optical film, and an optical laminate.

Background Art

[0002] As a material for improving the adhesiveness (adhesion) between a hydrophilic member (for example, a polarizer, an interlayer film for laminated glass, etc.) such as polyvinyl alcohol (PVA) and polyvinyl butyral (PVB), and an adherend member (for example, a polarizer protective film, an optically anisotropic layer, etc.), it is known to blend a compound having a boronic acid group into the adherend member. For example, Patent Document 1 describes a polymer compound having a repeating unit containing a boronic acid group in a side chain.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] When the present inventors examined the polymer compound described in Patent Document 1, it was revealed that there is room for improvement in the adhesiveness between the hydrophilic member and the adherend member.

[0005] Therefore, an object of the present invention is to provide a polymer compound capable of improving the adhesiveness between a hydrophilic member and an adherend member by blending it into the adherend member, as well as a composition, an optical film, and an optical laminate containing the polymer compound.

Means for Solving the Problems

[0006] As a result of diligent research to achieve the above objectives, the present inventors discovered that by using a polymer compound having repeating units containing a predetermined structure in its side chains as the material for forming the adherendable member, good adhesion between the formed adherendable member and the hydrophilic member is achieved, thus completing the present invention. In other words, we found that the above problem can be solved by the following configuration.

[0007] [1] A polymer compound having repeating units in which the structure represented by formula (1), described later, is included in the side chain. [2] The polymer compound described in [1], wherein the repeating unit having the structure represented by formula (1) described later in its side chain is the repeating unit represented by formula (2) described later. [3] A polymer compound as described in [1] or [2], wherein A in formula (1) described later represents a benzene ring. [4] X in equation (2) described later 2 The polymer compound according to [2], wherein the linking group is a single bond or at least one divalent linking group selected from the group consisting of -COO-, -OCO-, -CONH-, -O-, -CO-, and substituted or unsubstituted phenylene groups. [5] Furthermore, a polymer compound according to any of [1] to [4] having a repeating unit represented by formula (3) described later. [6] The polymer compound described in [5], wherein the repeating unit represented by formula (3) described later is the repeating unit represented by formula (4) described later. [7] R in equation (1) described later 3 However, fluorine atoms, chlorine atoms, bromine atoms, -OCOR 7 ,-COOR 8 , carboxyl group, and -COR 9 A polymer compound selected from the group consisting of [1] to [6], where R 7 , R 8 and R 9 Each of these independently represents a substituent. [8] A polymer compound according to any of [1] to [7], having a weight-average molecular weight of 5,000 to 100,000. [9] A polymer compound according to any one of [1] to [8], wherein the content of repeating units including the structure represented by formula (1) described later is 5 to 60% by mass.

[10] A polymer compound according to any one of [1] to [9], used as a member to be bonded to a hydrophilic member. A composition containing any of the polymer compounds described in [1] to

[10] .

[12] The composition according to

[11] further comprising a solvent.

[13] An optical film containing any of the polymer compounds described in [1] to

[10] .

[14] An optical film having a cured layer of the composition described in

[11] . An optical laminate in which the optical film described in

[15]

[13] and a hydrophilic member are bonded together via an adhesive layer. An optical laminate in which the optical film described in

[16]

[14] and a hydrophilic member are bonded together via an adhesive layer. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a polymer compound that can improve the adhesion between a hydrophilic member and a member to be bonded by being incorporated into the member to be bonded, as well as a composition containing the polymer compound, an optical film, and an optical laminate. [Modes for carrying out the invention]

[0009] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. In this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively.

[0010] Furthermore, in this specification, each component may be represented by a single substance or by a combination of two or more substances. When two or more substances are used in combination for each component, the content of that component refers to the total content of the combined substances unless otherwise specified.

[0011] Furthermore, in this specification, "(meth)acrylic" refers to "acrylic" or "methacrylic," and "(meth)acryloyl" refers to "acryloyl" or "methacryloyl."

[0012] Furthermore, in this specification, "substituted or unsubstituted" or "may have substituents" includes not only embodiments without substituents but also embodiments having one or more substituents. Examples of substituents include those listed in substituent group A below. <Substituent group A> Examples of substituents include, Halogen atoms (for example, fluorine atoms, chlorine atoms, bromine atoms, preferably chlorine atoms, fluorine atoms, more preferably fluorine atoms); Alkyl groups (preferably having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as linear, branched, or cyclic alkyl groups, for example, linear alkyl groups having 1 to 6 carbon atoms (e.g., methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group), branched alkyl groups having 3 to 6 carbon atoms (e.g., isopropyl group, isobutyl group, tert-butyl group, sec-butyl group, neopentyl group, isohexyl group, 3-methylpentyl group), and cyclic alkyl groups having 3 to 12 carbon atoms (e.g., cyclopropyl group, cyclopentyl group, cyclohexyl group, 1-norbornyl group, 1-adamantyl group)); Alkenyl groups (preferably alkenyl groups having 2 to 48 carbon atoms, more preferably alkenyl groups having 2 to 18 carbon atoms, such as vinyl groups, allyl groups, 1-butenyl groups, and 2-butenyl groups); Alkynyl group (preferably an alkynyl group having 2 to 6 carbon atoms, more preferably an alkynyl group having 2 to 4 carbon atoms, for example, an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group); Aryl groups (preferably aryl groups having 6 to 48 carbon atoms, more preferably aryl groups having 6 to 24 carbon atoms, for example, phenyl group, oligoaryl group (naphthyl group, anthryl group), phenanthrenyl group, fluorenyl group, pyrenyl group, triphenylenyl group, biphenyl group); Heteroaryl groups (preferably heterocyclic groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 2-thienyl group, 4-pyridyl group, 2-furyl group, 2-pyrimidinyl group, 1-pyridyl group, 2-benzothiazolyl group, 1-imidazolyl group, 1-pyrazolyl group, benzotriazole-1-yl group); Silyl groups (preferably silyl groups having 3 to 38 carbon atoms, more preferably silyl groups having 3 to 18 carbon atoms, for example, trimethylsilyl group, triethylsilyl group, tributylsilyl group, t-butyldimethylsilyl group, t-hexyldimethylsilyl group); Hydroxyl group; cyano group; nitro group; Alkoxy groups (preferably alkoxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methoxy group, ethoxy group, 1-butoxy group, 2-butoxy group, isopropoxy group, t-butoxy group, dodecyloxy group, cycloalkyloxy group (for example, cyclopentyloxy group, cyclohexyloxy group)); Aryloxy group (preferably an aryloxy group having 6 to 48 carbon atoms, more preferably an aryloxy group having 6 to 24 carbon atoms, for example, a phenoxy group or a 1-naphthoxy group); Alkenyloxy groups (preferably alkenyloxy groups having 2 to 6 carbon atoms, for example, vinyloxy group, 1-propenyloxy group, 2-n-propenyloxy group (allyloxy group), 1-n-butenyloxy group, prenyloxy group); Heterocyclic oxy groups (preferably heterocyclic oxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 1-phenyltetrazole-5-oxy group, 2-tetrahydropyranyloxy group); Silyloxy group (preferably a silyloxy group having 1 to 32 carbon atoms, more preferably a silyloxy group having 1 to 18 carbon atoms, for example, trimethylsilyloxy group, t-butyldimethylsilyloxy group, diphenylmethylsilyloxy group); Acyloxy group (preferably an acyloxy group having 2 to 48 carbon atoms, more preferably an acyloxy group having 2 to 24 carbon atoms, for example, an acetoxy group, a pivaloyloxy group, a benzoyloxy group, a dodecanoyloxy group, an acryloyloxy group, a methacryloyloxy group); Alkoxycarbonyloxy groups (preferably alkoxycarbonyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, ethoxycarbonyloxy groups, t-butoxycarbonyloxy groups, cycloalkyloxycarbonyloxy groups (for example, cyclohexyloxycarbonyloxy groups)); An aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonyloxy group); Carbamoyloxy group (preferably a carbamoyloxy group having 1 to 48 carbon atoms, more preferably a carbamoyloxy group having 1 to 24 carbon atoms, for example, N,N-dimethylcarbamoyloxy group, N-butylcarbamoyloxy group, N-phenylcarbamoyloxy group, N-ethyl-N-phenylcarbamoyloxy group); Sulfamoyloxy group (preferably a sulfamoyloxy group having 1 to 32 carbon atoms, more preferably a sulfamoyloxy group having 1 to 24 carbon atoms, for example, N,N-diethylsulfamoyloxy group, N-propylsulfamoyloxy group); Alkylsulfonyloxy groups (preferably alkylsulfonyloxy groups having 1 to 38 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylsulfonyloxy groups, hexadecylsulfonyloxy groups, cyclohexylsulfonyloxy groups); Aryl sulfonyloxy group (preferably an aryl sulfonyloxy group having 6 to 32 carbon atoms, more preferably an aryl sulfonyloxy group having 6 to 24 carbon atoms, for example, a phenyl sulfonyloxy group); Acyl group (preferably having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, formyl group, acetyl group, acryloyl group, methacryloyl group, pivaloyl group, benzoyl group, tetradecanoyl group, cyclohexanoyl group); Alkoxycarbonyl groups (preferably alkoxycarbonyl groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl group, octadecyloxycarbonyl group, cyclohexyloxycarbonyl group, 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl group); An aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonyl group); Carbamoyl group (preferably a carbamoyl group having 1 to 48 carbon atoms, more preferably a carbamoyl group having 1 to 24 carbon atoms, for example, carbamoyl group, N,N-diethylcarbamoyl group, N-ethyl-N-octylcarbamoyl group, N,N-dibutylcarbamoyl group, N-propylcarbamoyl group, N-phenylcarbamoyl group, N-methylN-phenylcarbamoyl group, N,N-dicyclohexylcarbamoyl group); Amino groups (preferably with 32 or fewer carbon atoms, more preferably with 24 or fewer carbon atoms, for example, amino, methylamino group, N,N-dibutylamino group, tetradecylamino group, 2-ethylhexylamino group, cyclohexylamino group); Anilino group (preferably anilino group having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, anilino group, N-methylanilino group); Heterocyclic amino group (preferably a heterocyclic amino group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, a 4-pyridylamino group); Carbonamide group (preferably a carbonamide group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetamide group, benzamide group, tetradecaneamide group, pivaloylamide group, cyclohexaneamide group); Ureido group (preferably a ureido group having 1 to 32 carbon atoms, more preferably a ureido group having 1 to 24 carbon atoms, for example, a ureido group, an N,N-dimethylureido group, or an N-phenylureido group); Imide group (preferably an imide group having 36 or fewer carbon atoms, more preferably an imide group having 24 or fewer carbon atoms, for example, N-succinimide group, N-phthalimide group); Alkoxycarbonylamino groups (preferably alkoxycarbonylamino groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, methoxycarbonylamino group, ethoxycarbonylamino group, t-butoxycarbonylamino group, octadecyloxycarbonylamino group, cyclohexyloxycarbonylamino group); Aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 32 carbon atoms, more preferably an aryloxycarbonylamino group having 7 to 24 carbon atoms, for example, a phenoxycarbonylamino group); Sulfonamide group (preferably a sulfonamide group having 1 to 48 carbon atoms, more preferably a sulfonamide group having 1 to 24 carbon atoms, for example, methanesulfonamide group, butanesulfonamide group, benzenesulfonamide group, hexadecanesulfonamide group, cyclohexanesulfonamide group); Sulfamoylamino group (preferably a sulfamoylamino group having 1 to 48 carbon atoms, more preferably a sulfamoylamino group having 1 to 24 carbon atoms, for example, N,N-dipropylsulfamoylamino group, N-ethyl-N-dodecylsulfamoylamino group); Azo group (preferably an azo group having 1 to 32 carbon atoms, more preferably an azo group having 1 to 24 carbon atoms, for example, a phenylazo group or a 3-pyrazolylazo group); Alkylthio groups (preferably alkylthio groups having 1 to 48 carbon atoms, more preferably alkylthio groups having 1 to 24 carbon atoms, for example, methylthio group, ethylthio group, octylthio group, cyclohexylthio group); An arylthio group (preferably with 6 to 48 carbon atoms, more preferably an arylthio group with 6 to 24 carbon atoms, for example, a phenylthio group); Heterocyclic thio groups (preferably heterocyclic thio groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 2-benzothiazolylthio group, 2-pyridylthio group, 1-phenyltetrazolylthio group); Alkyl sulfinyl group (preferably an alkyl sulfinyl group having 1 to 32 carbon atoms, more preferably an alkyl sulfinyl group having 1 to 24 carbon atoms, for example, a dodecane sulfinyl group); Aryl sulfinyl group (preferably an aryl sulfinyl group having 6 to 32 carbon atoms, more preferably an aryl sulfinyl group having 6 to 24 carbon atoms, for example, a phenyl sulfinyl group); Alkyl sulfonyl groups (preferably alkyl sulfonyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methyl sulfonyl group, ethyl sulfonyl group, propyl sulfonyl group, butyl sulfonyl group, isopropyl sulfonyl group, 2-ethylhexyl sulfonyl group, hexadecyl sulfonyl group, octyl sulfonyl group, cyclohexyl sulfonyl group); Arylsulfonyl groups (preferably arylsulfonyl groups having 6 to 48 carbon atoms, more preferably arylsulfonyl groups having 6 to 24 carbon atoms, for example, phenylsulfonyl groups and 1-naphthylsulfonyl groups); Sulfamoyl group (preferably a sulfamoyl group having 32 or fewer carbon atoms, more preferably a sulfamoyl group having 24 or fewer carbon atoms, for example, sulfamoyl group, N,N-dipropylsulfamoyl group, N-ethyl-N-dodecylsulfamoyl group, N-ethyl-N-phenylsulfamoyl, N-cyclohexylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group); A phosphonyl group (preferably having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a phenoxyphosphonyl group, an octyloxyphosphonyl group, or a phenylphosphonyl group); A phosphinoylamino group (preferably having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a diethoxyphosphinoylamino group or a dioctyloxyphosphinoylamino group); Epoxy group;-NHCOCH3;-SO2NHC2H4OCH3;-NHSO2CH3; These are some examples, and you may combine two or more of them. These substituents may be further substituted by these substituents. When there are two or more substituents, they may be the same or different. Also, when possible, they may be bonded to each other to form a ring.

[0013] [Polymer compound] The polymer compound of the present invention is a polymer having a repeating unit containing the structure represented by the following formula (1) in the side chain. In the present invention, as described above, by using a polymer compound having a repeating unit containing the structure represented by the following formula (1) in the side chain as a material for forming the adherend member, the adhesiveness between the formed adherend member and the hydrophilic member becomes good. Although the details are not clear, the present inventors presume as follows. That is, R in the following formula (1) 3 is a monovalent group in which the Hammett substituent constant σ value shows a positive value, so the acid dissociation constant pKa of the boronic acid moiety represented by -B(OR 1 )OR 2 decreases, and it is considered that the adhesiveness becomes good by interacting (for example, covalent bonding) with the surface (for example, hydroxyl group) of the hydrophilic member. Hereinafter, the polymer compound of the present invention will be described in detail.

[0014] The polymer compound of the present invention is a polymer having a repeating unit containing the structure represented by the following formula (1) in the side chain. [Chemical formula]

[0015] In the above formula (1), A represents a monocyclic or polycyclic aromatic carbon ring or a monocyclic or polycyclic aromatic heterocyclic ring, and n which is the number of ring members of A represents an integer of 3 or more. Here, examples of the aromatic carbon ring represented by one aspect of A include a benzene ring, a naphthalene ring, an anthracene ring, a triphenylene ring, a fluorene ring, and the like. Furthermore, examples of aromatic heterocycles represented by one aspect of A include furan rings, pyrrole rings, thiophene rings, pyridine rings, thiazole rings, benzothiazole rings, oxadiazole rings, thiazolothiazole rings, and phenanthroline rings. Furthermore, as mentioned above, the number of ring members of A, n, represents an integer of 3 or more, preferably an integer between 4 and 14, and more preferably an integer between 5 and 10.

[0016] In the present invention, it is preferable that A in formula (1) above represents a benzene ring, because the resulting polymer compound has good solubility and the adhesion between the formed bonded member and the hydrophilic member is better.

[0017] In the above equation (1), R 1 and R 2 Each of these independently represents a hydrogen atom, or a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R 1 and R 2 These may be linked to one another via alkylene linking groups, arylene linking groups, or linking groups consisting of a combination thereof.

[0018] Here, R 1 and R 2 Examples of substituted or unsubstituted aliphatic hydrocarbon groups represented by one embodiment include alkyl groups, alkenyl groups, or alkynyl groups, which may have substituents. Examples of alkyl groups include linear, branched, or cyclic alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, hexadecyl, octadecyl, eicosyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, 1-methylbutyl, isohexyl, 2-methylhexyl, cyclopentyl, cyclohexyl, 1-adamantyl, and 2-norbornyl. Examples of alkenyl groups include linear, branched, or cyclic alkenyl groups such as vinyl, 1-propenyl, 1-butenyl, 1-methyl-1-propenyl, 1-cyclopentenyl, and 1-cyclohexenyl groups. Examples of alkynyl groups include, for example, ethynyl, 1-propynyl, 1-butynyl, and 1-octynyl groups.

[0019] Also, R 1 and R 2 Examples of substituted or unsubstituted aryl groups represented by one aspect include those in which one to four benzene rings form a fused ring, and those in which a benzene ring and an unsaturated five-membered ring form a fused ring. Specifically, examples include phenyl group, naphthyl group, anthryl group, phenanthryl group, indenyl group, acenabutenyl group, fluorenyl group, pyrenyl group, and the like.

[0020] Also, R 1 and R 2 One embodiment of the heteroaryl group, whether substituted or unsubstituted, is, for example, a heteroaryl group obtained by removing one hydrogen atom from a heteroaromatic ring containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms. Examples of heteroaromatic rings containing one or more heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur atoms include pyrrole, furan, thiophene, pyrazole, imidazole, triazole, oxazole, isoxazole, oxadiazole, thiazole, thiadiazole, indole, carbazole, benzofuran, dibenzofuran, thiaphthene, dibenzothiophene, indazolebenzimidazole, anthranil, benzisoxazole, benzoxazole, benzothiazole, purine, pyridine, pyridazine, pyrimidine, pyrazine, triazine, quinoline, acridine, isoquinoline, phthalazine, quinazoline, quinoxaline, naphthyridine, phenanthroline, and pteridine.

[0021] R in equation (1) above1 and R 2 It is preferable that these are hydrogen atoms or are linked to each other by alkylene linking groups.

[0022] In the above equation (1), R 3 This represents a monovalent group whose Hammett substituent constant σ value is positive. Here, Hammett's rule is an empirical rule proposed by L.P. Hammett in 1935 to quantitatively discuss the effect of substituents on the reaction or equilibrium of benzene derivatives, and it is widely accepted today. In this invention, "a monovalent group whose Hammett substituent constant σ value is positive" refers to a monovalent group in which at least one of the σ values ​​at the meta position (σm value) and the σ value at the para position (σp value) is positive, as described in the document "A Survey of Hammett Substituent Constants and Resonance and Field Parameters" (Chem. Rev. 1991, 91, 165-195). For substituents not specifically described in the above document, the values ​​calculated according to the calculation method described in the above document shall be adopted.

[0023] In the present invention, R in formula (1) above 3 However, fluorine atoms, chlorine atoms, bromine atoms, -OCOR 7 ,-COOR 8 carboxyl group, -COR 9 Preferably selected from the group consisting of cyano groups, -CF3, formyl groups, and -NO2, and among these, fluorine atoms, chlorine atoms, bromine atoms, and -OCOR atoms are preferred because they result in better adhesion between the bonded member and the hydrophilic member. 7 ,-COOR 8 , carboxyl group, and -COR 9 Preferably selected from the group consisting of a fluorine atom, a chlorine atom, a carboxyl group, and -COR 9 It is more preferable that R 7 , R 8 and R 9 Each of these independently represents a substituent.

[0024] In formula (1) above, m represents an integer between 1 and (n-2), preferably an integer between 1 and 4, and more preferably 1 or 2. Also, if m represents an integer greater than or equal to 2, multiple R 3 These may be the same or different.

[0025] In the present invention, A in formula (1) above is R as described above. 3 In addition, the molecule may have a monovalent group (e.g., an alkyl group, an alkoxy group, an amino group, etc.) whose Hammett substituent constant σ value is negative. Here, "a monovalent group whose Hammett substituent constant σ value is negative" refers to a monovalent group in which both the meta-position σ value (σm value) and the para-position σ value (σp value) are negative, as described in the literature "A Survey of Hammett Substituent Constants and Resonance and Field Parameters" (Chem. Rev. 1991, 91, 165-195).

[0026] In the above formula (1), L 1 * represents a single bond or a divalent linking group, and * represents the bond position to the main chain. Here, L 1 Examples of divalent linking groups represented by one embodiment include optionally substituted divalent hydrocarbon groups, optionally substituted divalent heterocyclic groups, -O-, -S-, -N(Q)-, -CO-, or combinations thereof. Q represents a hydrogen atom or a substituent. Examples of divalent hydrocarbon groups include divalent aliphatic hydrocarbon groups such as alkylene groups having 1 to 10 carbon atoms, alkenylene groups having 1 to 10 carbon atoms, and alkylene groups having 1 to 10 carbon atoms, as well as divalent aromatic hydrocarbon groups such as arylene groups. Examples of divalent heterocyclic groups include divalent aromatic heterocyclic groups, specifically pyridylene groups (pyridine-diyl groups), pyridazine-diyl groups, imidazole-diyl groups, thienylene groups (thiophene-diyl groups), and quinolylene groups (quinoline-diyl groups). Furthermore, examples of groups that combine these include groups that combine at least two selected from the group consisting of a divalent hydrocarbon group which may have substituents, a divalent heterocyclic group which may have substituents, and -O-, -S-, -N(Q)-, and -CO-. Examples include -CO-O-, -CO-N(Q)-, -CO-O-divalent hydrocarbon group-, -CO-N(Q)-divalent hydrocarbon group-, -CO-O-divalent hydrocarbon group-CO-O-, -CO-O-divalent hydrocarbon group-N(Q)-CO-O-, and -CO-O-divalent hydrocarbon group-O-divalent hydrocarbon group-.

[0027] In the present invention, for reasons such as ease of synthesis, it is preferable that the repeating unit containing the structure represented by formula (1) in its side chain is a repeating unit represented by the following formula (2). [ka]

[0028] In equation (2) above, A, R 1 , R 2 , R 3 The definitions and specific examples of A and R in equation (1) above are given by A and R respectively. 1 , R 2 , R 3 This is the same as the definition and specific examples of m.

[0029] In equation (2) above, R 4 This represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. Here, R 4 Examples of C1-C20 alkyl groups represented by one embodiment include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups, with the methyl group being preferred among them. Note, R 4 A hydrogen atom or a methyl group is preferred as the element.

[0030] In equation (2) above, X 1 This represents at least one divalent linking group selected from the group consisting of substituted or unsubstituted phenylene groups, -COO-, -OCO-, -CONH-, -O-, -CO-, and -CH2-. Note that -COO- is R 4 The carbon bonded to the X is bonded to C=O, 2 This indicates that O is combined with R, and -OCO- represents R 4 The carbon bonded to the oxygen is bonded to X 2 This represents the bonding of C=O, and -CONH- is R 4 The carbon bonded to the X is bonded to C=O, 2 This indicates that -NH- is binding with -NH-. Of these, X 1 The phenylene group is preferably a substituted or unsubstituted phenylene group, -COO-, and -CONH-, and more preferably -COO- and -CONH-.

[0031] In equation (2) above, X 2 This represents a single bond or a divalent linking group. Here, X 2 One aspect of the divalent linking group represented is L 1 One example is a divalent linking group similar to the one represented by one aspect of the above.

[0032] In the present invention, X in formula (2) above is used because it improves the adhesion between the bonded member and the hydrophilic member. 2 However, it is preferable to represent a single bond or at least one divalent linking group selected from the group consisting of -COO-, -OCO-, -CONH-, -O-, -CO-, and substituted or unsubstituted phenylene groups.

[0033] When the polymer compound of the present invention is a copolymer having repeating units represented by formula (3) described later, the content of repeating units including the structure represented by formula (1) is preferably 3 to 80% by mass. In particular, the lower limit of the content of repeating units including the structure represented by formula (1) is preferably 5% by mass or more, and more preferably 7% by mass or more, for the reason that the adhesion between the adhered member and the hydrophilic member is better. On the other hand, the upper limit of the content of repeating units including the structure represented by formula (1) is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less, for the reason that the solubility of the obtained polymer compound is good and the surface quality of the adhered member formed is good.

[0034] The polymer compound of the present invention preferably has repeating units represented by the following formula (3) because it results in a good surface texture of the bonded member and improved adhesion between the bonded member and the hydrophilic member. [ka]

[0035] In equation (3) above, R 5 This represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. Here, R 5 Examples of C1-C20 alkyl groups represented by one embodiment include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups, with the methyl group being preferred among them. Note, R 5 A hydrogen atom or a methyl group is preferred as the element.

[0036] In the above formula (3), L 2 represents a divalent linking group selected from the group consisting of -O-, -COO-, -OCO-, -CONH-, a divalent aliphatic group, and combinations thereof. Note that -COO- is R 5 The carbon bonded to R is bonded to C=O, 6This indicates that O is combined with R, and -OCO- represents R 5 The carbon bonded to the oxygen is bonded to R 6 This represents the bonding of C=O. L 2 One embodiment of the divalent aliphatic group can be a divalent aliphatic chain group or an aliphatic cyclic group. A divalent aliphatic chain group is preferably an alkylene group having 1 to 20 carbon atoms, and more preferably an alkylene group having 1 to 10 carbon atoms. A divalent aliphatic cyclic group is preferably a cycloalkylene group having 3 to 20 carbon atoms, and more preferably a cycloalkylene group having 3 to 15 carbon atoms. Of these, L 2 -COO- or -OCO- is preferred, with -COO- being more preferred.

[0037] In equation (3) above, R 6 This includes alkyl groups having 4 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms in which at least one hydrogen atom is substituted with a fluorine atom (hereinafter also referred to as "fluoroalkyl groups"), or -Si(R a3 )(R a4 ) Represents a monovalent organic group containing O-, R a3 and R a4 Each of these independently represents an alkyl group, a haloalkyl group, or an aryl group.

[0038] In the present invention, from the viewpoint of adhesion between the member to be bonded and the hydrophilic member, R in formula (3) above 6 However, it is preferably a fluoroalkyl group having 1 to 20 carbon atoms, more preferably a fluoroalkyl group having 1 to 18 carbon atoms, and even more preferably a fluoroalkyl group having 2 to 15 carbon atoms. Furthermore, the number of fluorine atoms is preferably 1 to 25, more preferably 3 to 21, and most preferably 5 to 21.

[0039] Furthermore, in the present invention, it is preferable that the repeating unit represented by formula (3) above be the repeating unit represented by formula (4) below, in order to improve the surface quality of the bonded member formed and to further improve the adhesion between the bonded member and the hydrophilic member. [ka]

[0040] In the above equation (4), R 5 This is R in equation (3) above. 5 Similarly, it represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and the preferred embodiment is the same. Furthermore, in formula (4) above, ma and na each independently represent integers from 0 to 19. In particular, from the viewpoint of improving adhesion and raw material availability, ma is preferably an integer from 1 to 8, and more preferably an integer from 1 to 5. Also, na is preferably an integer from 1 to 15, more preferably an integer from 1 to 12, even more preferably an integer from 2 to 10, and most preferably an integer from 5 to 7. However, the sum of ma and na represents an integer from 0 to 19. Furthermore, in formula (4) above, X represents a hydrogen atom or a fluorine atom, and is preferably fluorine.

[0041] Specifically, monomers that form the repeating unit represented by formula (3) or (4) above include, for example, 2,2,2-trifluoroethyl (meth)acrylate, 2,2,3,3,3-pentafluoropropyl (meth)acrylate, 2-(perfluorobutyl)ethyl (meth)acrylate, 2-(perfluorohexyl)ethyl (meth)acrylate, 2-(perfluorooctyl)ethyl (meth)acrylate, 2-(perfluorodecyl)ethyl (meth)acrylate, 2-(perfluoro-3-methylbutyl)ethyl (meth)acrylate, 2-(perfluoro-5-methylhexyl)ethyl (meth)acrylate, 2-(perfluoro-7-methyloctyl)ethyl (meth)acrylate, 1H,1H,3H-tetrafluoropropyl (meth)acrylate, and 1H,1H,5H-octafluoropentyl (meth)acrylate. Examples include rilate, 1H,1H,7H-dodecafluoroheptyl (meth)acrylate, 1H,1H,9H-hexadecafluorononyl (meth)acrylate, 1H-1-(trifluoromethyl)trifluoroethyl (meth)acrylate, 1H,1H,3H-hexafluorobutyl (meth)acrylate, 3-perfluorobutyl-2-hydroxypropyl (meth)acrylate, 3-perfluorohexyl-2-hydroxypropyl (meth)acrylate, 3-perfluorooctyl-2-hydroxypropyl (meth)acrylate, 3-(perfluoro-3-methylbutyl)-2-hydroxypropyl (meth)acrylate, 3-(perfluoro-5-methylhexyl)-2-hydroxypropyl (meth)acrylate, and 3-(perfluoro-7-methyloctyl)-2-hydroxypropyl (meth)acrylate.

[0042] On the other hand, R in equation (3) above 6 This indicates -Si(R a3 )(R a4 The monovalent organic group containing )O- is preferably an organic group derived from a siloxane bond, and more preferably a structure obtained by polymerizing a compound represented by the following formula (5). [ka]

[0043] In the above equation (5), R a1 R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and R a5 represents an alkyl group having 1 to 12 carbon atoms, with alkyl groups having 1 to 4 carbon atoms being more preferred.

[0044] In the above equation (5), R a3 and R a4 Each of these independently represents an alkyl group, a haloalkyl group, or an aryl group. Preferably, the alkyl group has 1 to 10 carbon atoms, and examples include a methyl group, an ethyl group, and a hexyl group. As the haloalkyl group, a fluorinated alkyl group having 1 to 10 carbon atoms is preferred, and examples include a trifluoromethyl group and a pentafluoroethyl group. The aryl group is preferably one having 6 to 20 carbon atoms, and examples include the phenyl group and the naphthyl group. Of these, R a3 and R a4 The group is preferably a methyl group, a trifluoromethyl group, or a phenyl group, with a methyl group being particularly preferred.

[0045] In formula (5) above, m represents an integer between 10 and 1000, preferably between 20 and 500, and more preferably between 30 and 200.

[0046] Examples of compounds represented by formula (5) above include polysiloxane macromers containing a (meth)acryloyl group at one end, such as Cyraprene 0721, 0725 (trade names, manufactured by JNC Corporation), AK-5, AK-30, AK-32 (trade names, manufactured by Toagosei Co., Ltd.), KF-100T, X-22-169AS, KF-102, X-22-3701IE, X-22-164B, X-22-164C, X-22-5002, X-22-173B, X-22-174D, X-22-167B, X-22-161AS (trade names, manufactured by Shin-Etsu Chemical Co., Ltd.).

[0047] In the present invention, when the repeating units represented by formula (3) are present, the content is preferably 2 to 80% by mass, more preferably 5 to 70% by mass, and even more preferably 10 to 60% by mass, relative to the total repeating units.

[0048] In the case of the polymer compound of the present invention, it is preferable to have repeating units containing polymerizable groups in the side chains, because when the member to be bonded is a hydrophobic member, the adhesion between the hydrophobic member and the hydrophilic member is improved. Examples of repeating units containing polymerizable groups in their side chains are those described in paragraphs

[0021] to

[0031] of International Publication No. 2018 / 062077, which are incorporated herein by reference.

[0049] The polymer compounds of the present invention may have other repeating units in addition to the repeating units described above, as needed. Other repeating units are those described in paragraphs

[0062] to

[0073] of International Publication No. 2018 / 062077, which are incorporated herein by reference.

[0050] The weight-average molecular weight (Mw) of the polymer compound of the present invention is preferably 2,000 to 200,000, which results in a good surface texture of the bonded member and better adhesion between the bonded member and the hydrophilic member. More preferably, it is 5,000 to 100,000, and even more preferably 8,000 to 50,000. The weight-average molecular weight was measured by gel permeation chromatography (GPC) under the following conditions. <Measurement conditions> [Eluent] N-methyl-2-pyrrolidone (NMP) [Device Name] EcoSEC HLC-8320GPC (Manufactured by Tosoh Corporation) [Column] TSKgel SuperAWM-H (manufactured by Tosoh Corporation) [Column temperature] 40℃ [Flow rate] 0.50ml / min

[0051] Specific examples of polymer compounds of the present invention having each of the repeating units described above include compounds represented by the following formulas (P-1) to (P-23).

[0052] [ka] JPEG0007850020000007.jpg169155 JPEG0007850020000008.jpg228107 JPEG0007850020000009.jpg29163 JPEG0007850020000010.jpg178121 JPEG0007850020000011.jpg39118

[0053] [Application] The polymer compound of the present invention is useful for improving the adhesion between a hydrophilic member and a member to be bonded, that is, as an adhesion promoter, and is preferably used in the member to be bonded to the hydrophilic member. The composition forming such an adhesive member is not particularly limited as long as it contains the polymer compound of the present invention, but other components include, for example, liquid crystalline compounds, inks, paints, and binder resins, and among these, liquid crystalline compounds are preferred. On the other hand, hydrophilic materials include, for example, materials made of polyvinyl alcohol (PVA) film or polyvinyl butyral (PVB) film, and specifically, polarizers and laminated glass interlayers are preferred examples.

[0054] [Composition] The composition of the present invention is a composition containing the polymer compound of the present invention, and from the viewpoint of workability, it is preferable that the composition further contains a solvent. Furthermore, as described above, the composition of the present invention is preferably a composition for forming a member to be bonded to a hydrophilic member.

[0055] The content of the polymer compound of the present invention is preferably 0.0001 to 40% by mass, more preferably 0.001 to 20% by mass, and even more preferably 0.1 to 5% by mass, when the total solid content (all components excluding the solvent) of the composition of the present invention is taken as 100% by mass.

[0056] 〔solvent〕 The solvent can be appropriately selected from the viewpoints of being able to dissolve or disperse the polymer compound of the present invention described above, as well as other components (such as liquid crystalline compounds), easily forming a uniform surface in the coating and drying processes, ensuring liquid storage properties, and having an appropriate saturated vapor pressure. Examples of such solvents include dibutyl ether, dimethoxyethane, diethoxyethane, propylene oxide, 1,4-dioxane, 1,3-dioxolane, 1,3,5-trioxane, tetrahydrofuran, anisole, phenethole, dimethyl carbonate, methyl ethyl carbonate, diethyl carbonate, acetone, methyl ethyl ketone (MEK), diethyl ketone, dipropyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone, methylcyclohexanone, ethyl formate, propyl formate, pentyl formate, methyl acetate, ethyl acetate, propyl acetate, methyl propionate, ethyl propionate, γ-butylolactone, methyl 2-methoxyacetate, methyl 2-ethoxyacetate, ethyl 2-ethoxyacetate, ethyl 2-ethoxypropionate, ethyl 2-methoxyethanol, 2-propoxyethanol. Examples include 2-butoxyethanol, 1,2-diacetoxyacetone, acetylacetone, diacetone alcohol, methyl acetoacetate, ethyl acetoacetate, methyl alcohol, ethyl alcohol, isopropyl alcohol, n-butyl alcohol, cyclohexyl alcohol, isobutyl acetate, methyl isobutyl ketone (MIBK), 2-octanone, 2-pentanone, 2-hexanone, ethylene glycol ethyl ether, ethylene glycol isopropyl ether, ethylene glycol butyl ether, propylene glycol methyl ether, ethyl carbitol, butyl carbitol, hexane, heptane, octane, cyclohexane, methylcyclohexane, ethylcyclohexane, benzene, toluene, xylene, etc., which can be used individually or in combination of two or more.

[0057] Of the above solvents, it is preferable to use at least one of cyclohexanone, methyl acetate, ethyl acetate, methyl ethyl ketone, acetone, methyl alcohol, ethyl alcohol, and isopropyl alcohol.

[0058] In the present invention, when a solvent is used, the amount contained is preferably in an amount such that the concentration of the solid content of the composition is in the range of 5 to 80% by mass, more preferably in an amount such that it is in the range of 10 to 75% by mass, and even more preferably in an amount such that it is in the range of 15 to 70% by mass.

[0059] [Other ingredients] When forming an optically anisotropic layer as a bonded member, the composition of the present invention may contain, for example, a liquid crystalline compound, a boron compound, and a polymerization initiator, in addition to the polymer compound and solvent described above. These components include those described in paragraphs

[0085] to

[0112] of International Publication No. 2018 / 062068, which are incorporated herein by reference.

[0060] [Optical film] The optical film of the present invention is an optical film containing the polymer compound of the present invention described above, or an optical film having a cured layer of the composition of the present invention described above. Examples of the cured layer of the composition of the present invention described above include an optically anisotropic layer obtained by curing a liquid crystal composition containing a liquid crystal compound together with the polymer compound and solvent of the present invention described above.

[0061] [Support] The optical film of the present invention may have a support. Examples of the above-mentioned support include glass substrates and polymer films, and examples of polymer film materials include cellulose polymers, cycloolefin polymers, polyester polymers, olefin polymers, (meth)acrylic polymers, and polyamide polymers.

[0062] Of these, it is preferable to use a polymer film made of a cellulose polymer, particularly a polymer film made of a cellulose acylate polymer (cellulose acylate film), or a polymer film made of a cycloolefin polymer (cycloolefin film) as a support.

[0063] In the present invention, the thickness of the support is not particularly limited, but considering mechanical strength and the case where the optical film of the present invention is stored in a long roll form, it is preferably 5 to 100 μm, more preferably 10 to 75 μm, and even more preferably 15 to 55 μm.

[0064] [Optical laminate] The optical laminate of the present invention is an optical laminate in which the optical film of the present invention described above and a hydrophilic member are bonded together via an adhesive layer. Furthermore, the optical laminate of the present invention is preferably a polarizing plate having a polarizer described later as a hydrophilic member.

[0065] [Polarizer] The polarizer is not particularly limited as long as it is a material that has the function of converting light into a specific linear polarization, and conventionally known absorptural polarizers and reflective polarizers can be used. Absorbing polarizers include iodine-based polarizers, dye-based polarizers using dichroic dyes, and polyene-based polarizers. Iodine-based and dye-based polarizers include coated polarizers and stretched polarizers, both of which are applicable, but polarizers made by adsorbing iodine or a dichroic dye onto polyvinyl alcohol and then stretching it are preferred. Furthermore, as a method for obtaining a polarizer by stretching and dyeing a laminated film in which a polyvinyl alcohol layer is formed on a substrate, examples include those described in Japanese Patent Publication No. 5048120, Japanese Patent Publication No. 5143918, Japanese Patent Publication No. 4691205, Japanese Patent Publication No. 4751481, and Japanese Patent Publication No. 4751486, and these known technologies related to polarizers can also be preferably utilized. Examples of reflective polarizers include polarizers made by stacking thin films with different birefringences, wire grid polarizers, and polarizers that combine a cholesteric liquid crystal with a selective reflection range and a quarter-wave plate. In particular, polarizers containing polyvinyl alcohol-based resins (polymers containing -CH2-CHOH- as repeating units, especially at least one selected from the group consisting of polyvinyl alcohol and ethylene-vinyl alcohol copolymers) are preferred because they exhibit better adhesion.

[0066] In the present invention, the thickness of the polarizer is not particularly limited, but is preferably 1 μm to 50 μm, more preferably 2 μm to 30 μm, and even more preferably 3 μm to 20 μm.

[0067] [Adhesive layer] The adhesive layer of the optical laminate of the present invention may be formed from an adhesive. As adhesives, adhesives containing resins having hydroxyl groups are preferred. Examples include polyvinyl alcohol-based adhesives, epoxy-based active energy ray curing adhesives, such as those described in Japanese Patent Application Publication No. 2004-245925, which contain epoxy compounds that do not contain aromatic rings in their molecules and are cured by heating or irradiation with active energy rays, and active energy ray curing adhesives described in Japanese Patent Application Publication No. 2008-174667, which contain, in a total amount of 100 parts by mass of (meth)acrylic compounds, (a) a (meth)acrylic compound having two or more (meth)acryloyl groups in its molecule, (b) a (meth)acrylic compound having a hydroxyl group in its molecule and only one polymerizable double bond, and (c) a phenol ethylene oxide modified acrylate or a nonylphenol ethylene oxide modified acrylate. Among these, polyvinyl alcohol-based adhesives are the most preferred. Polyvinyl alcohol-based adhesives are adhesives containing modified or unmodified polyvinyl alcohol. In addition to modified or unmodified polyvinyl alcohol, polyvinyl alcohol-based adhesives may also contain crosslinking agents. Specific examples of adhesives include aqueous solutions of polyvinyl alcohol or polyvinyl acetal (e.g., polyvinyl butyral) and latex of vinyl polymers (e.g., polyvinyl chloride, polyvinyl acetate, polybutyl acrylate). Particularly preferred adhesives are aqueous solutions of polyvinyl alcohol. In this case, it is preferable that the polyvinyl alcohol is fully saponified. Furthermore, epoxy-based active energy ray curable adhesives undergo ring-opening of epoxy groups upon irradiation with active energy rays, generating hydroxyl groups, which allows them to be crosslinked with the copolymer according to the present invention. Therefore, in the present invention, epoxy-based active energy ray curable adhesives are also included as hydroxyl group-containing adhesives and can be used as appropriate.

[0068] [Image display device] The present invention is an image display device having the above-described optical film or optical laminate and an image display element.

[0069] [Image display element] The image display element used in the present invention is not particularly limited and includes, for example, liquid crystal cells, organic electroluminescent (hereinafter abbreviated as "EL") display panels, and plasma display panels. Of these, a liquid crystal cell or an organic EL display panel is preferred, and a liquid crystal cell is more preferred. In other words, the image display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as the image display element, and preferably an organic EL display device using an organic EL display panel as the image display element, and more preferably a liquid crystal display device.

[0070] <Liquid crystal cell> The liquid crystal cells used in liquid crystal display devices are preferably in VA (Vertical Alignment) mode, OCB (Optical Compensated Bend) mode, FFS or IPS (In-Plane-Switching) mode, or TN (Twisted Nematic) mode, but are not limited to these.

[0071] In TN mode liquid crystal cells, when no voltage is applied, the rod-shaped liquid crystal molecules are substantially horizontally oriented and further twisted to a 60-120° angle. TN mode liquid crystal cells are the most widely used in color TFT (Thin Film Transistor) liquid crystal display devices and are described in numerous publications.

[0072] In VA mode liquid crystal cells, rod-shaped liquid crystalline molecules are substantially oriented vertically when no voltage is applied. VA mode liquid crystal cells include (1) narrowly defined VA mode liquid crystal cells in which rod-shaped liquid crystalline molecules are substantially oriented vertically when no voltage is applied and substantially oriented horizontally when voltage is applied (described in Japanese Patent Publication No. 2-176625), (2) multi-domain liquid crystal cells (MVA mode) that expand the viewing angle (described in SID97, Digest of tech.Papers (Proceedings) 28 (1997) 845), (3) liquid crystal cells in a mode (n-ASM mode) in which rod-shaped liquid crystalline molecules are substantially oriented vertically when no voltage is applied and twisted multi-domain orientation when voltage is applied (described in the Proceedings of the Japan Liquid Crystal Symposium 58-59 (1998)), and (4) SURVIVAL mode liquid crystal cells (presented at LCD International 98). Furthermore, it may be any of the following types: PVA (Patterned Vertical Alignment), Optical Alignment, or PSA (Polymer-Sustained Alignment). Details of these modes are described in detail in Japanese Patent Publication No. 2006-215326 and Japanese Patent Publication No. 2008-538819.

[0073] In IPS mode liquid crystal cells, rod-shaped liquid crystal molecules are oriented substantially parallel to the substrate, and when an electric field parallel to the substrate surface is applied, the liquid crystal molecules respond in a planar manner. In IPS mode, black is displayed when no electric field is applied, and the absorption axes of the upper and lower polarizers are orthogonal. Methods for reducing light leakage when displaying black at an oblique angle and improving the viewing angle using an optical compensation sheet are disclosed in Japanese Patent Publication No. 10-54982, Japanese Patent Publication No. 11-202323, Japanese Patent Publication No. 9-292522, Japanese Patent Publication No. 11-133408, Japanese Patent Publication No. 11-305217, and Japanese Patent Publication No. 10-307291, among others.

[0074] <OLED display panel> The organic EL display panel used as an image display element in the present invention is a display panel constructed using an organic EL element in which an organic light-emitting layer (organic electroluminescent layer) is sandwiched between electrodes (between the cathode and the anode). The configuration of the organic EL display panel is not particularly limited, and known configurations can be adopted. [Examples]

[0075] The present invention will be described in more detail below based on the following examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the following examples.

[0076] [Synthesis Example 1] <Example of synthesis of polymer compound A-1> (Synthesis of monomer component M-1) In a 300 mL three-necked flask equipped with a condenser, thermometer, dropping funnel, and stirrer, 5.0 g (0.03 mol) of 4-amino-2-fluorophenylboronic acid, 4.2 g of triethylamine, and 100 mL of ethyl acetate were added and cooled to below 10°C. 3.8 g (0.04 mol) of acrylate chloride was carefully added dropwise. After the addition was complete, the mixture was stirred at room temperature for 2 hours. The resulting solution was separated with 0.1 mol / L hydrochloric acid, and the organic layer was separated. Further separation was performed with aqueous baking soda solution, and magnesium sulfate was added to the organic layer. After drying, the solvent was removed by distillation to obtain 6.4 g of monomer component M-1, represented by the following formula (M-1). [ka]

[0077] (Synthesis of polymer compound A-1) A 300 mL three-necked flask equipped with a condenser, thermometer, stirrer, and dropping pump was filled with 10 g of cyclohexanone and 10 g of isopropyl alcohol (IPA), and heated to 85°C under a nitrogen atmosphere. Next, a mixed solution of 5.4 g of monomer component M-1, 6.6 g of 2-(perfluorobutyl)ethyl acrylate, 2.7 g of 1,3-propanediol, 0.16 g of azo polymerization initiator (V-601, manufactured by Wako Pure Chemical Industries, Ltd.), 10 g of cyclohexanone, and 10 g of IPA was added dropwise over 3 hours. After aging for 1 hour, a solution of 0.16 g of V-601 and 1 g of cyclohexanone was added and aged for a further 3 hours to obtain a solution containing polymer compound A-1 represented by the following formula (A-1). The weight-average molecular weight of the obtained polymer compound A-1 was 12,000. [ka]

[0078] [Other synthesis examples] Except for changing the type or amount of monomer components, polymer compounds A-2 to A-20 and CA-1 to CA-5, represented by the following formulas (A-2) to (A-20) and (CA-1) to (CA-5), were obtained using the same method as for polymer compound A-1. For the synthesis of polymer compounds A-2, A-5, and A-6, the monomer components were not changed; instead, the amount of polymerization initiator was adjusted to achieve the weight-average molecular weight shown in Table 1. [ka] JPEG0007850020000015.jpg33115 JPEG0007850020000016.jpg31132 JPEG0007850020000017.jpg38116 JPEG0007850020000018.jpg38113 JPEG0007850020000019.jpg38113 JPEG0007850020000020.jpg38113 JPEG0007850020000021.jpg38113 JPEG0007850020000022.jpg41110 JPEG0007850020000023.jpg29163 JPEG0007850020000024.jpg28147 JPEG0007850020000025.jpg33123 JPEG0007850020000026.jpg33110 JPEG0007850020000027.jpg38121 JPEG0007850020000028.jpg26121 JPEG0007850020000029.jpg59115 JPEG0007850020000030.jpg3362 JPEG0007850020000031.jpg3979 JPEG0007850020000032.jpg6685 JPEG0007850020000033.jpg30114 JPEG0007850020000034.jpg33117 JPEG0007850020000035.jpg3484 JPEG0007850020000036.jpg31132 JPEG0007850020000037.jpg1689

[0079] [Examples 1-20 and Comparative Examples 1-5] [Production of optical films] Each synthesized polymer compound was mixed with the following liquid crystalline compounds to prepare a liquid crystal composition with the composition shown below. -------------------------------------------------- Liquid crystal composition -------------------------------------------------- • 100.0 parts by mass of the following liquid crystalline compound G1 • 1.0 parts by mass of the following orientation aid H1 • 4.5 parts by mass of the following boron compound J1 • The monomer K1 below: 8.0 parts by mass • Polymerization initiator L1: 5.0 parts by mass • 0.5 parts by mass of the polymer compounds shown in Table 1 below. • 357 parts by mass of the mixed solvent in the following mass ratio (Mass ratio: acetone / methyl acetate / methanol = 70 / 20 / 10) --------------------------------------------------

[0080] • Liquid crystalline compound G1: A mixture of the following liquid crystalline compounds (RA), (RB), and (RC) in a mass ratio of 83:15:2. [ka]

[0081] • Orientation aid H1 [ka]

[0082] • Boron compound J1 [ka]

[0083] • Monomer K1: Viscoat #360 (manufactured by Osaka Organic Chemical Industry Co., Ltd.) • Polymerization initiator L1: OXE-01 (manufactured by BASF)

[0084] Additionally, one side of a cyclolevhine polymer film (manufactured by JSR Corporation, product name: Arton Film, Re=95nm, Rth=100nm, film thickness 25μm) was discharged at a rate of 125W·min / m 2 We then performed a COVID-19 treatment. Subsequently, each prepared liquid crystal composition was applied to the corona-treated surface using a #2.6 wire bar. The compositions were heated with 70°C hot air for 90 seconds to dry the solvent and to allow the liquid crystal compounds to be oriented and matured. Next, under nitrogen purging, with an oxygen concentration of 100 ppm, UV irradiation (300 mJ / cm²) was performed at 40°C. 2 The orientation of the liquid crystalline compound was fixed by performing the following procedure, and an optical film was fabricated.

[0085] [Fabrication of polarizing plates] <Surface treatment of film> A cellulose acetate film (Fujifilm, Fujitac TD40UC) was immersed for 1 minute in a 1.5 mol / L sodium hydroxide aqueous solution (saponification solution) heated to 37°C. The film was then rinsed with water, immersed in a 0.05 mol / L sulfuric acid aqueous solution for 30 seconds, and then passed through a water rinsing bath. After draining the water three times using an air knife, the film was dried in a 70°C drying zone for 15 seconds to produce a saponified cellulose acetate film.

[0086] <Fabrication of polarizers> According to Example 1 of Japanese Patent Publication No. 2001-141926, a polarizer with a thickness of 12 μm was fabricated by applying a peripheral speed difference between two pairs of nip rolls and stretching in the longitudinal direction.

[0087] <Bonding> After sandwiching the fabricated polarizer between each of the fabricated optical films and the fabricated saponified cellulose acetate film, the films were laminated roll-to-roll using the adhesive described below, so that the absorption axis of the polarizer and the longitudinal direction of the film were parallel. Here, one side of the polarizer is configured such that the coated surface of the optical film faces the polarizer, and the other side of the polarizer is made of the cellulose acetate film. Polarizing plates were fabricated by curing the laminated material by drying at 70°C for 10 minutes. (glue) Polyvinyl alcohol (manufactured by Kuraray, PVA-117H) 3% aqueous solution

[0088] [evaluation] [Solubility] 1.0 g each of the synthesized polymer compounds A-1 to A-20 and CA-1 to CA-5 were added to 15.0 g of methyl ethyl ketone. The solutions were visually observed and evaluated according to the following criteria. The results are shown in Table 1 below. <Evaluation Criteria> 2: No turbidity observed. 1: Slightly cloudy

[0089] [Surface shape] The planar properties of the optical anisotropy layer of the fabricated optical film were observed when it was inserted between polarizing plates stacked in a crossed nicol configuration. The degree of unevenness was visually evaluated and assessed according to the following criteria. The results are shown in Table 1 below. <Evaluation Criteria> 5: No unevenness is visible at all. 4: Slight unevenness is visible, but it's not noticeable. 3: Some unevenness is visible, but it is not a practical problem. 4: Unevenness is visible and poses a practical problem. 5: The unevenness is very noticeable and is quite bothersome.

[0090] [Adhesiveness] Adhesion was evaluated using the cross-cut method described in JIS-K-5600-5-6-1. For the fabricated polarizing plates, 100 grid lines were made on the optical film surface at 1 mm intervals, and an adhesion test was performed using cellophane tape (manufactured by Nichiban Co., Ltd.). The process of applying and peeling off new cellophane tape was repeated three times, and the results were evaluated according to the following criteria. The results are shown in Table 1 below. The grid lines were created by making cuts from the cyclolevine polymer film (support) side of the optical film, reaching the surface of the polarizer. <Evaluation Criteria> 5: The squares within the grid do not peel off. 4: 70% to less than 100% of the boards have no peeling of the squares within the grid. 3: 50% to less than 70% of the boards have no peeling of the squares within the grid. 2: Between 20% and less than 50% of the boards have no peeling of the squares within the grid. 1: Less than 20% of the grid squares are free from peeling. In this case, evaluation results of 5, 4, and 3 are acceptable in practice, but an evaluation of 5 is preferable.

[0091] [Table 1]

[0092] The results shown in Table 1 indicate that when the polymer compound of the present invention is not incorporated, the adhesion between the hydrophilic polarizer and the optically anisotropic layer (the component to be bonded) is poor (Comparative Examples 1-5). In contrast, it was found that when the polymer compound of the present invention is incorporated, the adhesion between the hydrophilic polarizer and the optically anisotropic layer, which is the adherend, is good (Examples 1-20). In particular, a comparison of Examples 2, 16, and 17 revealed that when A in formula (1) represents a benzene ring, the resulting polymer compound exhibits good solubility, and the adhesion between the bonded member and the hydrophilic member is also improved. Also, from the comparison between Example 3 and Example 4, X in the above formula (2) 2 represents a single bond or at least one divalent linking group selected from the group consisting of -COO-, -OCO-, -CONH-, -O-, -CO-, and a substituted or unsubstituted phenylene group, it was found that the adhesiveness between the formed adherend member and the hydrophilic member becomes better. Also, from the comparison between Example 3 and Example 18, when the polymer compound of the present invention has a repeating unit represented by the above formula (3), the flatness of the formed adherend member is good, and also, it was found that the adhesiveness between the adherend member and the hydrophilic member becomes better. Also, from the comparison between Example 3, Example 12 and Example 13, when the repeating unit represented by the above formula (3) is the repeating unit represented by the above formula (4), the flatness of the formed adherend member becomes better, and also, it was found that the adhesiveness between the adherend member and the hydrophilic member becomes even better. Also, from the comparison between Example 3, Example 14 and Example 15, R in the above formula (1) 3 is selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, -OCOR 7 , -COOR 8 , a carboxy group, and an acetyl group, it was found that the adhesiveness between the formed adherend member and the hydrophilic member becomes better. Also, from the comparison between Example 2, Example 5 and Example 6, when the weight average molecular weight of the polymer compound of the present invention is 5000 to 100000, the flatness of the formed adherend member is good, and also, it was found that the adhesiveness between the adherend member and the hydrophilic member becomes better. Also, from the comparison between Example 2, Example 7 and Example 8, when the upper limit value of the content of the repeating unit containing the structure represented by the above formula (1) is 60% by mass or less, the solubility of the obtained polymer compound is good, and also, it was found that the flatness of the formed adherend member is good. From the comparison between Example 2 and Example 9, when the lower limit value of the content of the repeating unit containing the structure represented by the above formula (1) is 5% by mass or more, it was found that the adhesiveness between the adherend member and the hydrophilic member becomes better.

Claims

1. A polymer compound having a repeating unit containing the structure represented by the following formula (1) in its side chain, and further having a repeating unit represented by the following formula (3). 【Chemistry 1】 Here, in equation (1) above, A represents a monocyclic or polycyclic aromatic carbocyclic ring, or a monocyclic or polycyclic aromatic heterocyclic ring, and n, which is the number of members in A, represents an integer of 3 or more. R １ and R ２ Each of these independently represents a hydrogen atom, or a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R １ and R ２ These may be linked to one another via alkylene linking groups, arylene linking groups, or linking groups consisting of a combination thereof. R ３ R represents a monovalent group whose Hammett substituent constant σ value is positive, and m represents an integer between 1 and (n-2). When m represents an integer of 2 or greater, multiple R ３ These may be the same or different. L １ * represents a single bond or a divalent linking group, and * represents the bond position to the main chain. 【Chemistry 2】 Here, in equation (3) above, R5 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. R6 represents a C4-C20 alkyl group, a C1-C20 alkyl group in which at least one hydrogen atom is substituted with a fluorine atom, or a monovalent organic group containing -Si(Ra3)(Ra4)O-, and Ra3 and Ra4 each independently represent an alkyl group, a haloalkyl group, or an aryl group. L2 represents a divalent linking group selected from the group consisting of -O-, -COO-, -OCO-, -CONH-, a divalent aliphatic group, and combinations thereof.

2. The polymer compound according to claim 1, wherein the repeating unit having the structure represented by formula (1) in its side chain is the repeating unit represented by the following formula (2). 【Transformation 3】 Here, in equation (2) above, A, R １ R ２ R ３ The definitions of A, R １ R ２ R ３ and m are the same as the definitions of A, R R ４ This represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. X １ These are substituted or unsubstituted phenylene groups, -COO-, -OCO-, -CONH-, -O-, -CO-, and -CH ２ Represents at least one divalent linking group selected from the group consisting of -. X ２ This represents a single bond or a divalent linking group.

3. The polymer compound according to claim 1, wherein A in formula (1) represents a benzene ring.

4. In equation (2) above, X ２ The polymer compound according to claim 2, wherein the linking group represents a single bond or at least one divalent linking group selected from the group consisting of -COO-, -OCO-, -CONH-, -O-, -CO-, and substituted or unsubstituted phenylene groups.

5. The polymer compound according to claim 1, wherein the repeating unit represented by formula (3) is the repeating unit represented by the following formula (4). 【Chemistry 4】 Here, in equation (4), R ５ This represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. ma and na each independently represent integers between 0 and 19. However, ma and na together represent an integer between 0 and 19. X represents a hydrogen atom or a fluorine atom.

6. R in formula (1) ３ However, fluorine atom, chlorine atom, bromine atom, -OCOR ７ , -COOR ８ , carboxyl group, and -COR ９ A polymer compound according to claim 1, selected from the group consisting of R ７ , R ８ and R ９ Each of these independently represents a substituent.

7. The polymer compound according to claim 1, wherein the weight-average molecular weight is 5,000 to 100,000.

8. The polymer compound according to claim 1, wherein the content of repeating units including the structure represented by formula (1) is 5 to 60% by mass.

9. The polymer compound according to claim 1, used in a member to be bonded to a hydrophilic member.

10. A composition containing the polymer compound described in any one of claims 1 to 9.

11. Furthermore, the composition according to claim 10, further containing a solvent.

12. An optical film containing a polymer compound having a repeating unit in which the side chain contains a structure represented by the following formula (1). 【Transformation 5】 Here, in equation (1) above, A represents a monocyclic or polycyclic aromatic carbocyclic ring, or a monocyclic or polycyclic aromatic heterocyclic ring, and n, which is the number of members in A, represents an integer of 3 or more. R1 and R2 each independently represent a hydrogen atom, or a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R1 and R2 may be linked to each other via an alkylene linking group, an arylene linking group, or a linking group consisting of a combination thereof. R3 represents a monovalent group whose Hammett substituent constant σ value is positive, and m represents an integer between 1 and (n-2). When m represents an integer of 2 or greater, multiple R3s may be the same or different. L1 represents a single bond or a divalent linking group, and * represents the bond position to the main chain.

13. An optical film having a cured layer of a composition containing a polymer compound having a repeating unit in which the side chain contains a structure represented by the following formula (1). 【Transformation 6】 Here, in equation (1) above, A represents a monocyclic or polycyclic aromatic carbocyclic ring, or a monocyclic or polycyclic aromatic heterocyclic ring, and n, which is the number of members in A, represents an integer of 3 or more. R1 and R2 each independently represent a hydrogen atom, or a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and R1 and R2 may be linked to each other via an alkylene linking group, an arylene linking group, or a linking group consisting of a combination thereof. R3 represents a monovalent group whose Hammett substituent constant σ value is positive, and m represents an integer between 1 and (n-2). When m represents an integer of 2 or greater, multiple R3s may be the same or different. L1 represents a single bond or a divalent linking group, and * represents the bond position to the main chain.

14. An optical laminate in which the optical film described in claim 12 and a hydrophilic member are bonded together via an adhesive layer.

15. An optical laminate in which the optical film described in claim 13 and a hydrophilic member are bonded together via an adhesive layer.

Images