WO2024242041A1 - 液晶組成物、光学異方性層、光学フィルム、偏光板および画像表示装置 - Google Patents
液晶組成物、光学異方性層、光学フィルム、偏光板および画像表示装置 Download PDFInfo
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- WO2024242041A1 WO2024242041A1 PCT/JP2024/018281 JP2024018281W WO2024242041A1 WO 2024242041 A1 WO2024242041 A1 WO 2024242041A1 JP 2024018281 W JP2024018281 W JP 2024018281W WO 2024242041 A1 WO2024242041 A1 WO 2024242041A1
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- C08F234/00—Copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain and having one or more carbon-to-carbon double bonds in a heterocyclic ring
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- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
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Definitions
- the present invention relates to a liquid crystal composition, an optically anisotropic layer, an optical film, a polarizing plate, and an image display device.
- a circular polarizing plate consisting of a ⁇ /4 plate and a linear polarizing plate has been used in a display device.
- An example of the display device is an organic electroluminescence (EL) display device.
- EL organic electroluminescence
- the circular polarizing plate as described in Patent Document 1, an embodiment using an optically anisotropic layer with reverse wavelength dispersion is disclosed.
- a method of using a polymerizable compound exhibiting reverse wavelength dispersion to prepare an optically anisotropic layer with reverse wavelength dispersion is widely used because it has features such as enabling accurate conversion of light wavelengths over a wide wavelength range and enabling the optically anisotropic layer to be thinned due to its high refractive index.
- a change in the thickness of the optically anisotropic layer is accompanied by a change in retardation, and when the optically anisotropic layer is used as a circular polarizing plate in a display device, the change in the color of the reflected light occurs. Therefore, the optically anisotropic layer is required to have a uniform thickness in the plane. In order to achieve such a uniform thickness, it is necessary to uniformly coat the reverse dispersion liquid crystal composition on the substrate. In order to uniformly coat the substrate, it is known to use a liquid crystal composition containing a surfactant containing a polyfluoro group [-(CF 2 ) n -, n is an integer of 1 or more].
- Patent Document 2 describes an embodiment in which a liquid crystal composition containing a reverse dispersion liquid crystal compound, a polymer surfactant having a repeating unit containing a polyfluoro group, and a solvent is used.
- Patent Document 3 describes an embodiment that uses a liquid crystal composition that contains a reverse dispersion liquid crystal compound, a polyacrylate-based surfactant, and a solvent.
- the inventors have investigated the liquid crystal composition and liquid crystal cured layer (optically anisotropic layer) described in Patent Document 3 and other documents, and have found that, depending on the structure of the surfactant contained in the liquid crystal composition, repelling and wind unevenness may occur during the formation of the optically anisotropic layer.
- the present invention aims to provide a liquid crystal composition, an optically anisotropic layer, an optical film, a polarizing plate, and an image display device that can form an optically anisotropic layer in which repelling and wind unevenness are suppressed when forming a reverse dispersion liquid crystal cured layer, without using a compound having a polyfluoro group.
- the present inventors have found that by blending a specific surfactant in a liquid crystal composition for forming a reverse-dispersion cured liquid crystal layer, an optically anisotropic layer in which repelling and wind unevenness are suppressed during the formation of the reverse-dispersion cured liquid crystal layer can be formed, and have completed the present invention. That is, it has been found that the above object can be achieved by the following configuration.
- An optically anisotropic layer comprising a liquid crystal cured layer obtained by fixing an alignment state of a liquid crystal composition containing a reverse dispersion compound (I) represented by formula (1) described later, at least one liquid crystal compound, and a surfactant (II) having a structure represented by formula (2) described later in the molecule, wherein the optically anisotropic layer satisfies the relationship of formula (3) described later.
- a reverse dispersion compound (I) represented by formula (1) described later
- at least one liquid crystal compound at least one liquid crystal compound
- a surfactant (II) having a structure represented by formula (2) described later in the molecule wherein the optically anisotropic layer satisfies the relationship of formula (3) described later.
- the optically anisotropic layer according to [1] wherein the reverse dispersion compound (I) is a liquid crystal compound.
- the surfactant (II) is a surfactant that, when a solution containing 0.08% by mass of the surfactant (II) and cyclopentanone and methyl ethyl ketone in a mass ratio of 4:1 is prepared, the surface tension of the solution is 22 mN/m or more.
- the optically anisotropic layer according to any one of [1] to [9], wherein, when the solubility parameter of the liquid crystal mixture is defined as a weighted average value obtained by multiplying the solubility parameters of all liquid crystal compounds contained in the liquid crystal composition by the content of each liquid crystal compound, the relative energy difference of the surfactant (II) with respect to the liquid crystal mixture in the solubility parameters is from 6 to 12.
- the relative energy difference means the distance between the solubility parameter of the surfactant (II) and the solubility parameter of the liquid crystal mixture.
- the relative energy difference means the distance between the solubility parameter of the monomer of the repeating unit B and the solubility parameter of the liquid crystal mixture.
- the liquid crystal composition further contains a solvent, The solvent contains a high-boiling point solvent having a boiling point of 130° C. or higher, The optically anisotropic layer according to any one of [1] to [22], wherein the content of the high boiling point solvent is 150 parts by mass or more based on 100 parts by mass of the liquid crystal compound.
- the liquid crystal composition further contains a solvent,
- the solvent contains a high-boiling point solvent having a boiling point of 130° C. or higher
- the optically anisotropic layer according to [11] wherein the content of the high boiling point solvent is 150 parts by mass or more based on 100 parts by mass of the liquid crystal compound.
- 100 parts by mass of the liquid crystal compound which is the standard for the content of the high boiling point solvent, is 100 parts by mass of the total amount of the liquid crystal compound including the reverse dispersion compound (I) when the reverse dispersion compound (I) is a liquid crystal compound.
- An optical film having the optically anisotropic layer according to any one of [1] to [24].
- a polarizing plate comprising the optically anisotropic layer according to any one of [1] to [24] and a polarizer.
- the polarizing plate according to [26] further comprising a positive C plate.
- An image display device having the optically anisotropic layer according to any one of [1] to [24].
- a liquid crystal composition comprising a reverse dispersion compound (I) represented by formula (1) described later, at least one liquid crystal compound, and a surfactant (II) having a structure represented by formula (2) described later in the molecule.
- 100 parts by mass of the liquid crystal compound, which is the basis for the content of the surfactant (II) is 100 parts by mass of the total amount of the liquid crystal compound including the reverse dispersion compound (I) when the reverse dispersion compound (I) is a liquid crystal compound.
- liquid crystal composition according to any one of items [29] to [32], wherein the content of the high-boiling point solvent is 150 parts by mass or more based on 100 parts by mass of the liquid crystal compound.
- 100 parts by mass of the liquid crystal compound which is the standard for the content of the high boiling point solvent, is 100 parts by mass of the total amount of the liquid crystal compound including the reverse dispersion compound (I) when the reverse dispersion compound (I) is a liquid crystal compound.
- the present invention provides a liquid crystal composition, an optically anisotropic layer, an optical film, a polarizing plate, and an image display device that can form an optically anisotropic layer in which repelling and wind unevenness are suppressed when forming a reverse dispersion liquid crystal cured layer.
- FIG. 1 is a schematic cross-sectional view showing an example of an optical film.
- a numerical range expressed using "to” means a range that includes the numerical values before and after "to" as the lower and upper limits.
- the upper or lower limit value of a certain numerical range in a stepwise described numerical range may be replaced with the upper or lower limit value of another stepwise described numerical range.
- the upper or lower limit value of a certain numerical range in a numerical range described in the present specification may be replaced with a value shown in the examples.
- each component may be used alone or in combination of two or more substances corresponding to each component.
- the content of the component refers to the total content of the substances used in combination, unless otherwise specified.
- “(meth)acrylate” is a notation representing “acrylate” or “methacrylate”
- “(meth)acrylic” is a notation representing “acrylic” or “methacrylic”
- “(meth)acryloyl” is a notation representing "acryloyl” or “methacryloyl”.
- the bonding direction of a divalent group (e.g., -O-CO-) represented in this specification is not particularly limited.
- L2 when L2 is -O-CO- in the bond of " L1 - L2 - L3 ", when the position bonded to L1 side is *1 and the position bonded to L3 side is *2, L2 may be *1-O-CO-*2 or *1-CO-O-*2.
- Re( ⁇ ) and Rth( ⁇ ) respectively represent the in-plane retardation and the retardation in the thickness direction at a wavelength ⁇ , which is set to 550 nm unless otherwise specified.
- examples of the substituent include the substituents described in the following Substituent Group A.
- the phrase "optionally substituted” includes embodiments having one or more substituents as well as embodiments having no substituents.
- substituents include: Halogen atoms (e.g., fluorine, chlorine, bromine atoms); Alkyl groups (preferably linear, branched or cyclic alkyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as linear alkyl groups having 1 to 6 carbon atoms (e.g., methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl), branched alkyl groups having 3 to 6 carbon atoms (e.g., isopropyl, isobutyl, tert-butyl, sec-butyl, neopentyl, isohexyl, 3-methylpentyl), and cyclic alkyl groups having 3 to 12 carbon atoms (e.g., cyclopropyl, cyclopentyl)
- the liquid crystal composition is a composition in which the coating layer exhibits a liquid crystal phase in a specified temperature range.
- the liquid crystal composition of the present invention contains a reverse dispersion compound (I) represented by formula (1) described later, at least one liquid crystal compound, and a surfactant (II) (hereinafter also referred to as a "specific surfactant”) having a structure represented by formula (2) described later in the molecule.
- the reverse dispersion compound (I) may or may not exhibit liquid crystallinity.
- the reverse dispersion compound (I) when the reverse dispersion compound (I) exhibits liquid crystallinity, the reverse dispersion compound (I) and the liquid crystal compound may be the same compound, but in order to expand the temperature range in which the liquid crystal phase is exhibited, it is preferable that the compound further contains a liquid crystal compound that does not exhibit reverse dispersion.
- the liquid crystal composition of the present invention is suitably used as a liquid crystal composition for forming a liquid crystal cured layer constituting the optically anisotropic layer of the present invention described below.
- the present invention by blending a specific surfactant into the liquid crystal composition that forms the liquid crystal cured layer, repelling and wind unevenness are suppressed when forming the liquid crystal cured layer, and an optically anisotropic layer with reverse dispersion properties and sufficient film thickness uniformity for application to display devices can be formed.
- the liquid crystal compound contained in the liquid crystal composition of the present invention is not particularly limited.
- the type of liquid crystal compound contained in the liquid crystal composition is not particularly limited.
- liquid crystal compounds can be classified into rod-shaped and disk-shaped types based on their shape. Each of these can be further divided into low molecular weight and high molecular weight types.
- High molecular weight generally refers to a compound with a degree of polymerization of 100 or more (Polymer Physics: Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992).
- reverse dispersion liquid crystal compounds containing mesogen groups as a branched structure are also known.
- any liquid crystal compound can be used, but it is preferable to use a rod-shaped liquid crystal compound or a reverse dispersion liquid crystal compound. It is more preferable to use two or more liquid crystal compounds selected from the group consisting of rod-shaped liquid crystal compounds and reverse dispersion liquid crystal compounds.
- the liquid crystal compound is preferably a polymerizable liquid crystal compound having a polymerizable group.
- the polymerizable liquid crystal compound is preferably at least one type of polymerizable liquid crystal compound selected from the group consisting of polymerizable rod-like liquid crystal compounds and polymerizable reverse dispersion liquid crystal compounds.
- the polymerizable group include an acryloyl group, a methacryloyl group, an epoxy group, and a vinyl group.
- the alignment of the liquid crystal compound having such a polymerizable group can be fixed by polymerizing the liquid crystal compound in an aligned state. After the liquid crystal compound is fixed by polymerization, it is no longer necessary for the liquid crystal compound to exhibit liquid crystallinity.
- the reverse dispersion compound (I) contained in the liquid crystal composition of the present invention is a reverse dispersion compound (I) represented by the following formula (1), and is preferably a liquid crystal compound.
- the reverse dispersion property means "reverse wavelength dispersion property”
- a reverse dispersion compound is a compound that has a retardation film produced using the compound, and has a retardation in a plane at a specific wavelength (visible light range). This refers to a case in which, when the (Re) value is measured, the Re value remains the same or increases as the measurement wavelength increases.
- D 1 , D 2 , D 3 and D 4 each independently represent a single bond, or -CO-, -O-, -S-, -C( ⁇ S)-, -CR 1 R 2 -, -CR 3 ⁇ CR 4 -, -NR 5 -, or a divalent linking group consisting of a combination of two or more of these, and R 1 to R 5 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.
- G1 represents AG or SPG .
- a 1 , A 2 and A G each independently represent an aromatic hydrocarbon ring which may have a substituent, an aromatic heterocycle which may have a substituent, or a divalent alicyclic hydrocarbon group which may have a substituent, provided that one or more of the -CH 2 - constituting the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-.
- SP 1 , SP 2 and SP G each independently represent a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that one or more of the -CH 2 - constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-.
- Q represents a substituent.
- L1 and L2 each independently represent a monovalent organic group, and at least one of L1 and L2 represents a polymerizable group, provided that when at least one of Ar1 and Ar2 is an aromatic ring represented by the following formula (Ar-4), at least one of L1 and L2 and L3 and L4 in the following formula (Ar-4) represents a polymerizable group.
- m represents an integer of 0 to 2. When m is 2, each of the multiple G 1s may be the same or different, and each of the multiple D 1s may be the same or different.
- l and n each independently represent 0 or an integer of 1 or more, and when l is an integer of 2 or more, a plurality of A 1 may be the same or different, and a plurality of D 3 may be the same or different. When n is an integer of 2 or more, a plurality of D 4 may be the same or different, and a plurality of A 2 may be the same or different. Also, p represents 0 or an integer of 1 or more. When p is an integer of 2 or more, the multiple Ar 1s may be the same or different, and the multiple D 2s may be the same or different.
- the multiple G 1s may be the same or different, and the multiple D 1s may be the same or different.
- G 1 , D 1 and D 2 all represent a single bond, and an embodiment in which D 2 represents a single bond and m represents 0.
- examples of the divalent linking group represented by one embodiment of D 1 , D 2 , D 3 and D 4 include, for example, -CO-, -O-, -CO-O-, -C( ⁇ S)O-, -CR 1 R 2 -, -CR 1 R 2 -CR 1 R 2 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-CR 1 R 2 -, -CO-O-CR 1 R 2 -, -O-CO-CR 1 R 2 -, -CR 1 R 2 -O-CO-CR 1 R 2 -, -CR 1 R 2 -O-CO-CR 1 R 2 -, -NR 5 -CR 1 R 2 - and -CO-NR 5 R 1 , R 2 and R 5 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.
- D 1 , D 2 , D 3 and D 4 are preferably
- examples of the aromatic hydrocarbon ring represented by one embodiment of A 1 , A 2 and A G include aromatic hydrocarbon rings having 6 to 20 carbon atoms, and specific examples thereof include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring.
- Examples of the aromatic heterocycle represented by one embodiment of A 1 , A 2 and A G include aromatic heterocycles having 5 to 20 carbon atoms, specifically, a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, a benzothiazole ring, etc.
- the divalent alicyclic hydrocarbon group represented by one embodiment of A 1 , A 2 and A G is preferably a 5-membered or 6-membered ring.
- the divalent alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a divalent saturated alicyclic hydrocarbon group.
- divalent alicyclic hydrocarbon groups may be substituted with -O-, -S- or -NH-.
- divalent alicyclic hydrocarbon groups include divalent alicyclic hydrocarbon groups having 5 to 12 carbon atoms, and specific examples thereof include monocyclic hydrocarbon groups and bridged cyclic hydrocarbon groups, and more specific examples thereof include those represented by the following formulae (g-1) to (g-10).
- examples of the substituent that the aromatic hydrocarbon ring, aromatic heterocycle or divalent alicyclic hydrocarbon group may have include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group or a halogen atom is preferable.
- examples of the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by one embodiment of SP 1 , SP 2 , and SP G include linear alkylene groups having 1 to 20 carbon atoms or branched alkylene groups having 3 to 20 carbon atoms, linear alkenylene groups having 1 to 20 carbon atoms or branched alkenylene groups having 3 to 20 carbon atoms, and linear alkynylene groups having 1 to 20 carbon atoms or branched alkynylene groups having 3 to 20 carbon atoms.
- an alkylene group having 1 to 12 carbon atoms is preferable, and an alkylene group having 1 to 10 carbon atoms is more preferable.
- Suitable examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group.
- linear alkenylene group having 1 to 20 carbon atoms or the branched alkenylene group having 3 to 20 carbon atoms an alkenylene group having 2 to 10 carbon atoms is preferable, and an alkenylene group having 2 to 4 carbon atoms is more preferable, and a suitable example thereof is an ethenylene group.
- linear alkynylene group having 1 to 20 carbon atoms or the branched alkynylene group having 3 to 20 carbon atoms an alkynylene group having 2 to 10 carbon atoms is preferable, and an alkynylene group having 2 to 4 carbon atoms is more preferable, and a suitable example thereof is an ethynylene group.
- one or more of the -CH 2 - constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-.
- substituent represented by Q include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group or a halogen atom is preferable.
- G1 in the above formula (1) is preferably AG among the above-mentioned AG and SPG .
- G 1 in the above formula (1) preferably represents a cycloalkane ring or a cycloalkene ring.
- the cycloalkane ring include a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclododecane ring, and a cyclodocosane ring.
- cycloalkene ring examples include a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring, a cyclopentadiene ring, and a cyclohexadiene ring.
- examples of the monovalent organic group represented by L 1 and L 2 include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a cyano group, and a carboxy group.
- the alkyl group may be linear, branched, or cyclic, but is preferably linear.
- the number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 10.
- the aryl group may be monocyclic or polycyclic, but is preferably monocyclic.
- the number of carbon atoms in the aryl group is preferably 6 to 25, and more preferably 6 to 10.
- the heteroaryl group may be monocyclic or polycyclic.
- the number of heteroatoms constituting the heteroaryl group is preferably 1 to 3.
- the heteroatoms constituting the heteroaryl group are preferably nitrogen atoms, sulfur atoms, and oxygen atoms.
- the number of carbon atoms in the heteroaryl group is preferably 6 to 18, and more preferably 6 to 12.
- the alkyl group, aryl group, and heteroaryl group may be unsubstituted or may have a substituent. Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
- the polymerizable group represented by at least one of L 1 and L 2 is not particularly limited, but is preferably a polymerizable group capable of radical polymerization or cation polymerization.
- a known radical polymerizable group can be used, and a suitable one can be an acryloyloxy group or a methacryloyloxy group.
- the polymerization rate of the acryloyloxy group is generally fast, and from the viewpoint of improving productivity, the acryloyloxy group is preferred, but the methacryloyloxy group can also be used as the polymerizable group.
- a known cationic polymerizable group can be used, and specific examples thereof include an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiro orthoester group, and a vinyloxy group.
- an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is particularly preferable.
- Particularly preferred examples of the polymerizable group include those represented by any one of the following formulae (P-1) to (P-20): In the following formulae, Me represents a methyl group, and Et represents an ethyl group.
- L1 and L2 in the above formula (1) are both polymerizable groups, and more preferably an acryloyloxy group or a methacryloyloxy group.
- m represents an integer of 0 to 2
- l and n each independently represent an integer of 0 or 1 or more
- p represents an integer of 0 or 1 or more.
- m is preferably 0 or 1, and more preferably 1 from the viewpoint of synthesis.
- l and n it is preferable that they are integers of 0 to 2 from the viewpoints of solubility and compatibility with other liquid crystal compounds.
- p an integer of 0 to 2 is preferable, and 0 or 1 is more preferable.
- l and n in the above formula (1) each represent 1, and A1 and A2 each represent a benzene ring, because liquid crystallinity is easily exhibited in a wide temperature range including room temperature and birefringence ( ⁇ n) is also large.
- Ar 1 and Ar 2 each independently represent any aromatic ring selected from the group consisting of groups represented by the following formulae (Ar-1) to (Ar-8).
- *1 represents the bonding position with D 3 or D 4
- *2 represents the bonding position with D 1 or D 2.
- the bonding position with D 3 represents the bonding position with SP 1
- *2 represents the bonding position with D 2
- the bonding position with D 4 represents the bonding position with SP 2 .
- Q 1 represents N or CH
- Q 2 represents -S-, -O-, or -N(R 6 )-
- R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
- Y 1 represents a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, a monovalent aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or a monovalent alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and one or more of the -CH 2 - constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-.
- alkyl group having 1 to 6 carbon atoms represented by one embodiment of R 6 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.
- Examples of the monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms represented by one embodiment of Y1 include aryl groups such as a phenyl group, a 2,6-diethylphenyl group, and a naphthyl group.
- Examples of the monovalent aromatic heterocyclic group having 3 to 12 carbon atoms represented by one embodiment of Y 1 include heteroaryl groups such as a thienyl group, a thiazolyl group, a furyl group, and a pyridyl group, as well as groups obtained by removing one hydrogen atom from any of an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzothiazole ring, and a benzoxazole ring.
- heteroaryl groups such as a thienyl group, a thiazolyl group, a furyl group, and a pyridyl group, as well as groups obtained by removing one hydrogen atom from any of an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzothiazole ring, and a be
- the aromatic heterocyclic group having 3 to 12 carbon atoms represented by Y 1 is preferably a group obtained by removing one hydrogen atom from a benzofuran ring or a benzothiazole ring.
- Examples of the monovalent alicyclic hydrocarbon group having 6 to 20 carbon atoms represented by one embodiment of Y 1 include a cyclohexyl group, a cyclopentyl group, a norbornyl group, and an adamantyl group.
- Examples of the substituent that Y 1 may have include the substituents described in the above-mentioned Substituent Group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
- Z 1 , Z 2 and Z 3 each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 or -COR 12 , R 7 to R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 may be bonded to each other to form an aromatic ring.
- an alkyl group having 1 to 15 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, specifically, a methyl group, an ethyl group, an isopropyl group, a tert-pentyl group (1,1-dimethylpropyl group), a tert-butyl group, or a 1,1-dimethyl-3,3-dimethyl-butyl group is further preferable, and a methyl group, an ethyl group, or a tert-butyl group is particularly preferable.
- Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include monocyclic saturated hydrocarbon groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, a methylcyclohexyl group, and an ethylcyclohexyl group; monocyclic unsaturated hydrocarbon groups such as a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, a cyclodecenyl group, a cyclopentadienyl group, a cyclohexadienyl group, a cyclooctadienyl group,
- the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, and a biphenyl group, and an aryl group having 6 to 12 carbon atoms (particularly a phenyl group) is preferred.
- Specific examples of the monovalent aromatic heterocyclic group having 6 to 20 carbon atoms include a 4-pyridyl group, a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group.
- halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among these, a fluorine atom, a chlorine atom, and a bromine atom are preferred.
- specific examples of the alkyl group having 1 to 6 carbon atoms represented by R 7 to R 12 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.
- Z 1 and Z 2 may be bonded to each other to form an aromatic ring.
- an example of a structure in which Z 1 and Z 2 in the above formula (Ar-1) are bonded to each other to form an aromatic ring is a group represented by the following formula (Ar-1a).
- *1 represents the bonding position with D 3 or D 4 in the above formula (1)
- *2 represents the bonding position with D 1 or D 2 in the above formula (1).
- the bonding position with D 3 represents the bonding position with SP 1
- *2 represents the bonding position with D 2
- n the bonding position with D 4 represents the bonding position with SP 2 .
- Q 1 , Q 2 and Y 1 are the same as those explained in the above formula (Ar-1).
- either one of Z 1 and Z 2 in the above formulae (Ar-1) to (Ar-8) represents a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms (particularly a tert- butyl group), for the reasons that liquid crystallinity is easily expressed, solubility is improved, and durability of the optically anisotropic film to be formed is improved.
- Z 1 in the above formulas (Ar-1) to (Ar-8) represents a hydrogen atom and Z 2 represents a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms (particularly a tert-butyl group).
- A3 and A4 each independently represent a group selected from the group consisting of -O-, -N( R13 )-, -S-, and -CO-, and R13 represents a hydrogen atom or a substituent.
- R 13 represents a hydrogen atom or a substituent.
- substituents represented by one embodiment of R 13 include the substituents described in the above-mentioned Substituent Group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
- X represents a nonmetallic atom of Groups 14 to 16.
- the nonmetallic atom may have a hydrogen atom or a substituent bonded thereto.
- Examples of the non-metallic atom of Groups 14 to 16 represented by X include an oxygen atom, a sulfur atom, a nitrogen atom bonded to a hydrogen atom or a substituent [ ⁇ N—R N1 , R N1 represents a hydrogen atom or a substituent], and a carbon atom bonded to a hydrogen atom or a substituent [ ⁇ C(R C1 ) 2 , R C1 represents a hydrogen atom or a substituent].
- substituents described in the above-mentioned substituent group A include the substituents described in the above-mentioned substituent group A.
- preferred examples include an alkyl group, an alkoxy group, an alkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (for example, a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, an alkylcarbonyl group, a sulfo group, and a hydroxyl group.
- examples of the divalent linking group include the same groups as those explained in relation to D 1 , D 2 , D 3 and D 4 in the above formula (1).
- SP 3 and SP 4 each independently represent a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms.
- one or more of the -CH 2 - constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-.
- Q represents a substituent.
- the substituent represented by Q include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group or a halogen atom is preferable.
- examples of the divalent aliphatic hydrocarbon group include the same groups as those explained in relation to SP 1 , SP 2 and SP G in the above formula (1).
- L 3 and L 4 each independently represent a monovalent organic group, and at least one of L 3 and L 4 and L 1 and L 2 in the above formula (1) represents a polymerizable group.
- examples of the monovalent organic group include the same ones as those explained in relation to L1 and L2 in the above formula (1).
- examples of the polymerizable group include the same groups as those explained for L 1 and L 2 in the above formula (1).
- Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.
- Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.
- the aromatic rings in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring.
- Q3 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms.
- Ax and Ay include those described in paragraphs [0039] to [0095] of WO 2014/010325.
- Specific examples of the alkyl group having 1 to 20 carbon atoms represented by Q3 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.
- substituents described in the above-mentioned Substituent group A examples include the substituents described in the above-mentioned Substituent group A. Among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
- Ar 1 and Ar 2 in the above formula (1) represent any one of aromatic rings selected from the group consisting of groups represented by the above formulas (Ar-1), (Ar-2), and (Ar-4) to (Ar-8).
- the reverse dispersion compound (I) represented by the above formula (1) includes, for example, compounds in which p in the above formula (1) is 0, such as compounds represented by general formula (1) described in JP 2010-084032 A (particularly, the compounds described in paragraphs [0067] to [0073]), compounds represented by general formula (II) described in JP 2016-053709 A (particularly, the compounds described in paragraphs [0036] to [0043]), compounds represented by general formula (1) described in JP 2016-081035 A (particularly, the compounds described in paragraphs [0043] to [0055]), and compounds described in paragraphs [0025] to [0056] of WO 2021/060427 A.
- compounds in which p in the above formula (1) is 1 include compounds represented by the following formulas (I) to (XII).
- compounds having the groups shown in Tables 1 to 8 below as D 1 , G 1 , D 2 and K in the following formulas (I) to (VI) respectively include compounds having the groups shown in Tables 1 to 8 below as D 1 , G 1 , G 1 , D 2 and K in the following formulas (VII) to (XII) respectively include compounds having the groups shown in Table 9 below as D 1 , G 1 , G 1 , D 2 and K in the following formulas (VII) to (XII) respectively.
- the group adjacent to the acryloyloxy group represents a propylene group (a group in which a methyl group is substituted with an ethylene group), and represents a mixture of positional isomers in which the position of the methyl group is different.
- the surfactant (II) (specific surfactant) contained in the liquid crystal composition of the present invention is a compound having a structure represented by the following formula (2). Moreover, the surfactant (II) preferably has three or more structures represented by the following formula (2), and more preferably has three to six of them.
- R 21 , R 22 and R 23 each independently represent an alkyl group, an alkenyl group, an aryl group or an alkylenearyl group.
- the alkyl group include linear alkyl groups having 1 to 18 carbon atoms, and branched or cyclic alkyl groups having 3 to 18 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group.
- Examples of the alkenyl group include alkenyl groups having 2 to 12 carbon atoms.
- the aryl group may, for example, be an aryl group having a carbon number of 6 to 12. Specific examples include a phenyl group, an ⁇ -methylphenyl group, and a naphthyl group.
- the alkylenearyl group may, for example, be an alkylenearyl group having 7 to 30 carbon atoms.
- R 21 , R 22 and R 23 in the above formula (2) are all alkyl groups, because the surface tension of the liquid crystal composition is reduced and wind unevenness can be further suppressed when the liquid crystal cured layer is formed.
- the surfactant (II) is preferably a compound having a structure represented by the following formula (4), because the surface tension of the liquid crystal composition is reduced and wind unevenness can be further suppressed during the formation of a cured liquid crystal layer.
- R 31 to R 39 each independently represent an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. Specific examples of these groups are the same as those described for R 21 , R 22 , and R 23 in the above formula (2).
- the surfactant (II) is also preferably a compound having a structure represented by the following formula (5), because the surface tension of the liquid crystal composition is reduced and wind unevenness can be further suppressed during the formation of the cured liquid crystal layer.
- R 41 to R 45 each independently represent an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. Specific examples of these groups are the same as those described for R 21 , R 22 , and R 23 in the above formula (2).
- ns represents an integer of 1 to 15. When ns is an integer of 2 to 15, the multiple R 41 may be the same or different, and the multiple R 42 may be the same or different.
- the compatibility of the surfactant (II) with the above-mentioned liquid crystal compound and the solvent described below can be controlled, and wind unevenness and repelling can be further suppressed.
- the compatibility can be appropriately adjusted by using the solubility parameter (HSP) obtained by the Hansen sphere method. That is, the solubility parameters ( ⁇ D, ⁇ P, ⁇ H) of the solvent, liquid crystal compound, and surfactant are calculated using commercially available software (HSPiP-Hansen Solubility Parameters in Practice), and the relative energy difference ⁇ HSP (compound 1, compound 2) between any compound 1 and compound 2 is calculated as shown in the following formula (H1).
- the relative energy difference between the liquid crystal mixture and the surfactant (II) is preferably 6 to 12, more preferably 6 to 11, further preferably 6 to 9, and particularly preferably 7 to 9.
- the relative energy difference of the surfactant (II) with respect to the liquid crystal mixture means the distance between the solubility parameter of the surfactant (II) and the solubility parameter of the liquid crystal mixture, that is, the above-mentioned relative energy difference ⁇ HSP.
- the surfactant (II) is preferably a polymer containing a repeating unit A having the structure of the above formula (2) (hereinafter, also referred to as "specific polymer"), because the surface tension of the liquid crystal composition is reduced and wind unevenness can be further suppressed during the formation of a cured liquid crystal layer.
- the repeating unit A is preferably a repeating unit containing a structure represented by the following formula (6), and it is more preferable that both the repeating unit A and a repeating unit B described later are repeating units containing a structure represented by the following formula (6).
- R 51 and R 52 each independently represent a hydrogen atom or an alkyl group.
- R 53 represents a hydrogen atom or a substituent.
- L5 represents -O- or -NR Z -, where R Z represents a hydrogen atom or a substituent.
- examples of the alkyl group represented by one embodiment of R 51 and R 52 include linear alkyl groups having 1 to 18 carbon atoms and branched or cyclic alkyl groups having 3 to 18 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group.
- R 51 and R 52 are preferably hydrogen atoms.
- examples of the substituent represented by R 53 include an alkyl group, an alkenyl group, an aryl group, or a substituent having a linking group and a structure represented by the above formula (2) at the end.
- L 1 represents -O- or -NR Z -.
- R 11 , R 12 and R 13 each independently represent an alkyl group, an alkenyl group, an aryl group or an alkylenearyl group.
- m represents an integer of 2 or more.
- L 2 represents a linking group having a valence of m+1.
- R 53 is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
- R 53 is preferably a hydrogen atom or a methyl group.
- the substituent which is an embodiment of R Z is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
- L5 is preferably -O- or -NH-, and more preferably -O-.
- the repeating unit A is a repeating unit represented by the following formula (6-1), because this reduces the surface tension of the liquid crystal composition while maintaining compatibility with the liquid crystal compound, and wind unevenness can be further suppressed when forming the cured liquid crystal layer.
- R 51 , R 52 , R 53 and L 5 are the same as those explained in the above formula (6).
- R 21 , R 22 and R 23 are the same as those described in the above formula (2), except that multiple R 21 may be the same or different, multiple R 22 may be the same or different, and multiple R 23 may be the same or different.
- ms represents an integer of 2 or more.
- L6 represents an ms+1 valent linking group.
- ms is preferably an integer of 3 or more, more preferably an integer of 3 to 6, and even more preferably an integer of 3 to 5.
- preferred examples of the ms+1 valent linking group represented by L6 include ms+1 valent hydrocarbon groups having 1 to 10 carbon atoms which may have a substituent, in which some of the carbon atoms constituting the hydrocarbon group may be substituted with heteroatoms.
- the substituent that the hydrocarbon group may have is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
- the heteroatom include a silicon atom, an oxygen atom, and a nitrogen atom.
- repeating unit A examples include repeating units corresponding to the monomers represented by the following formulae K-1 to K-34, in which Bu represents a butyl group.
- the monomer represented by the following formula K-1 will be referred to as "monomer K-1.”
- the monomer represented by the following formula K-29 is a mixture of monomers having different numbers of -(O-Si(CH 3 ) 2 )-, it is expressed as an average value with n ⁇ 10. The same applies to the monomer represented by the following formula K-30.
- the content of the repeating unit A in the specific polymer is preferably 40% by mass or more and 90% by mass or less, and more preferably 50% by mass or more and 80% by mass or less, based on the mass of the specific polymer.
- the content of the repeating unit A is 40% by mass or more, wind unevenness is further suppressed when the cured liquid crystal layer is formed, and when the content of the repeating unit A is 90% by mass or less, repelling is further suppressed when the cured liquid crystal layer is formed, and the orientation of the cured liquid crystal layer becomes better.
- the surfactant (II) is a polymer having repeating units A with two or more different structures, since this inhibits aggregation of the surfactant (II) and suppresses repelling.
- the surfactant (II) is preferably a polymer (hereinafter also abbreviated as "specific copolymer") having, in addition to the repeating unit A, one or more repeating units B not containing the structure of the above formula (2), in order to control the compatibility with the above liquid crystal compound and the solvent described later and to adjust the surface tension in the process from coating to drying.
- the surfactant (II) when it is a specific copolymer, it may be a random copolymer or a block copolymer, but from the viewpoint of compatibility with other components in the liquid crystal composition, it is preferably a random copolymer.
- the surfactant (II) (specific surfactant) used in the examples described below is a random copolymer unless otherwise specified.
- the structure of the main chain of the repeating unit B is not particularly limited, and examples thereof include known structures.
- a skeleton selected from the group consisting of (meth)acrylic, (meth)acrylamide, styrene, siloxane, cycloolefin, methylpentene, and aromatic ester is preferred.
- a skeleton selected from the group consisting of a (meth)acrylic, (meth)acrylamide, siloxane, and cycloolefin skeleton is more preferred, and a (meth)acrylic skeleton or a (meth)acrylamide skeleton is even more preferred.
- the relative energy difference of the monomer of the repeating unit B with respect to the liquid crystal mixture is preferably 1-8, more preferably 3-7, and even more preferably 4-7.
- the relative energy difference of the monomer of repeating unit B with respect to the liquid crystal mixture means the distance between the solubility parameter of the monomer of repeating unit B and the solubility parameter of the liquid crystal mixture, that is, the above-mentioned relative energy difference ⁇ HSP.
- the repeating unit B is preferably a repeating unit containing a functional group that reacts with light or heat to form a crosslink.
- the functional group may be a radically polymerizable group or a cationic polymerizable group, preferably a radically polymerizable group, or may be a functional group capable of forming a covalent complex with a hydroxyl group.
- radical polymerizable group known radical polymerizable groups can be used, such as vinyl group, allyl group, vinyloxy group, maleimide group, allyloxy group, (meth)acryloyl group, (meth)acryloyloxy group, and (meth)acrylamide group.
- (meth)acryloyl group or (meth)acryloyloxy group is preferred.
- a known cationic polymerizable group can be used, for example, an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiro orthoester group, and a vinyloxy group.
- an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is more preferable.
- a boronic acid group (-B(OH) 2 ) and a boronic ester group (-B(OR B1 ) 2 ) are preferred.
- Each R independently represents a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group, and is preferably a hydrogen atom or an optionally substituted alkyl group.
- the alkyl group preferably has 1 to 10 carbon atoms, and more preferably has 1 to 5 carbon atoms.
- the number of carbon atoms in the aryl group is preferably from 4 to 20, and more preferably from 6 to 12.
- aryl group is a phenyl group.
- the number of carbon atoms in the heteroaryl group is particularly preferably 3 to 10, and more preferably 3 to 5.
- Examples of the heteroatom contained in the heteroaryl group include an oxygen atom, a nitrogen atom, and a sulfur atom.
- R B1 may be bonded to each other to form a ring.
- the number of ring members of the ring formed by bonding with each other of R B1 is preferably 4 to 8, and more preferably 5 to 6.
- the number of the functional groups contained in the repeating unit B is preferably 1 or more, more preferably 1 to 3, and even more preferably 1 or 2.
- repeating unit B having the above functional group the repeating unit represented by the following formula (b1) is preferred because it has better compatibility with liquid crystal compounds.
- R 51 , R 52 , R 53 and L 5 are the same as those explained in formula (6-1) above.
- L7 represents a single bond or a divalent linking group.
- the divalent linking group includes a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
- the aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferably an alkylene group having 1 to 15 carbon atoms, and more preferably an alkylene group having 2 to 8 carbon atoms.
- One or more of the -CH 2 - constituting the divalent aliphatic hydrocarbon group may be independently substituted with a group selected from -O-, -S-, -CO-, and -N(Q)-. Two or more -CH 2 - may be substituted as long as the same group is not adjacent.
- L 7 is preferably an alkylene group having 2 to 8 carbon atoms which may have a substituent, or *-(L 71 -O) n7 -*. * represents a bonding position.
- n7 represents an integer of 1 to 8.
- Each L 71 independently represents an alkylene group having 1 to 6 carbon atoms which may have a substituent, and is preferably an alkylene group having 2 to 4 carbon atoms which may have a substituent.
- the divalent linking group represented by L7 may be a group containing a mesogen group. As the group containing a mesogen group, *-SP 1 -M 1 -* is preferable. * represents a bonding position. SP 1 represents a spacer group, and M 1 represents a mesogen group.
- the spacer group is not particularly limited as long as it is a divalent linking group that does not contain a ring structure, and examples thereof include divalent chain aliphatic hydrocarbon groups having 1 to 20 carbon atoms.
- the divalent chain-like aliphatic hydrocarbon group having 1 to 20 carbon atoms is preferably an alkylene group having 1 to 15 carbon atoms, and more preferably an alkylene group having 1 to 8 carbon atoms.
- Specific preferred examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group, and a heptylene group.
- One or more of the -CH 2 - constituting the divalent chain aliphatic hydrocarbon group may be each independently substituted with a group selected from -O-, -S-, -CO-, and -N(Q)-. Two or more -CH 2 - may be substituted as long as the same group is not adjacent.
- Q represents a hydrogen atom or a substituent.
- the substituent represented by Q is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.
- the spacer group is preferably *-(CH 2 -CH 2 -O) n1 -*, *-(CH 2 ) n2 -O-*, or *-(CH 2 ) n2 -O-CO-*.
- * represents a bonding position.
- n1 represents an integer of 1 to 4.
- Each n2 independently represents an integer of 1 to 6, preferably an integer of 2 to 4.
- mesogenic group known mesogenic groups can be used. For example, reference can be made to the description in “Flussige Kristalle in Tabellen II” (VEB Manual Verlag fur Grundstoff Industrie, Leipzig, published in 1984), particularly pages 7 to 16, and to the description in "Liquid Crystal Handbook” edited by the Liquid Crystal Handbook Editorial Committee (Maruzen, published in 2000), particularly Chapter 3.
- the mesogenic group is preferably a group having at least one cyclic structure selected from the group consisting of an aromatic hydrocarbon group, a heterocyclic group, and an alicyclic group.
- the mesogenic group is preferably a group having an aromatic hydrocarbon group or a group having an alicyclic group, which may have a substituent, more preferably a group having 2 to 4 aromatic hydrocarbon groups, which may have a substituent, and even more preferably a group having 3 aromatic hydrocarbon groups, which may have a substituent, in order to improve the degree of alignment of the liquid crystal compound.
- a substituent an alkyl group, an alkoxy group, an alkyl ester group, or an acetyl group is preferable, and a methyl group, a tert-butyl group, a methoxy group, or a methyl ester group is more preferable.
- Examples of the substituents that the divalent linking group may have include a hydroxy group, a halogen atom, an amino group, an alkyl group, an alkoxy group, an acyl group, an aryl group, a nitro group, a cyano group, an alkylcarbonyl group, and a sulfonyl group.
- P1 represents a radically polymerizable group or a cationic polymerizable group.
- Preferred embodiments of the radically polymerizable group or the cationic polymerizable group are as described above.
- repeating units having a polymerizable group include the repeating units shown below.
- n represents an integer of 1 or more (typically an integer of 1 to 6).
- the repeating unit B is preferably a repeating unit containing a structure represented by the following formula (7), since it is easy to synthesize and has excellent controllability of the solubility parameter by adjusting np and nq below.
- R 61 represents a hydrogen atom or a methyl group. Furthermore, R 62 represents a hydrogen atom or an alkyl group having 1 to 18 carbon atoms. In addition, np represents an integer of 1 to 4, and nq represents an integer of 1 to 100.
- the repeating unit B is preferably a repeating unit having any one of a hydroxy group, a boronic acid group, a boronic acid ester group, a boronic acid amide group, an epoxy group, an oxetane group, a vinyl group, a styryl group, a (meth)acryloyl group (including a (meth)acrylamide group), a maleimide group, a naphthyl group, and a mesogen group.
- Specific examples of the repeating unit B having a mesogenic group include compounds described in WO2023/54164.
- the content of repeating unit B in the specific copolymer is preferably 0 to 50% by mass, and more preferably 10 to 50% by mass, relative to the mass of the specific copolymer.
- the surfactant (II) is preferably a surfactant that inhibits aggregation of the surfactant (II) in the composition, suppresses repelling, and when a solution containing ethyl ketone in a mass ratio of 4:1 is prepared, the surface tension of the solution is preferably 22 mN/m or more. Furthermore, since the surfactant (II) stabilizes the surface tension of the composition and suppresses wind unevenness, it is preferable that the surfactant be one that causes the surface tension of the solution to be 30 mN/m or less, and it is more preferable that the surfactant be one that causes the surface tension of the solution to be 27 mN/m or less.
- the surface tension of the solution is measured twice using a static surface tensiometer (model: CBVP-Z) manufactured by Kyowa Interface Science Co., Ltd., and the measured value is adopted.
- the liquid crystal composition of the present invention preferably contains surfactants (II) having two or more different structures, since this inhibits aggregation of surfactants (II) and suppresses repelling.
- the content of the surfactant (II) is preferably 0.01 to 10 mass %, more preferably 0.02 to 1 mass %, and even more preferably 0.04 to 0.5 mass %, relative to the total solid content (100 mass %) of the liquid crystal composition, in order to obtain better effects of the present invention.
- the content of the surfactant (II) is preferably 0.1 parts by mass or less per 100 parts by mass of the liquid crystal compound, since this inhibits aggregation of the surfactant (II) and suppresses repelling and wind unevenness.
- the 100 parts by mass of the liquid crystal compound which is the basis for the content of the surfactant (II), is 100 parts by mass of the total amount of the liquid crystal compound including the reverse dispersion compound (I) when the reverse dispersion compound (I) is a liquid crystal compound.
- the weight average molecular weight (Mw) of the surfactant (II) is preferably from 7,000 to 40,000, more preferably from 7,000 to 30,000, and even more preferably from 7,000 to 15,000.
- Mw weight average molecular weight
- the weight average molecular weight in the present invention is a value measured by gel permeation chromatography (GPC).
- Solvent Tetrahydrofuran
- Apparatus name EcoSEC HLC-8320GPC (manufactured by Tosoh Corporation)
- the liquid crystal composition of the present invention preferably contains a solvent.
- the solvent include ketones (e.g., acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone), ethers (e.g., dioxane, tetrahydrofuran, tetrahydropyran, dioxolane, tetrahydrofurfuryl alcohol, and cyclopentyl methyl ether), aliphatic hydrocarbons (e.g., hexane), alicyclic hydrocarbons (e.g., cyclohexane), aromatic hydrocarbons (e.g., benzene, toluene, xylene, and trimethylbenzene), halogenated carbons (e.g., dichloromethane, trichloromethane (chloro
- organic solvent examples include organic solvents such as ethyl acetate, ethyl acetate, ethyl propionate, butyl acetate, and diethyl carbonate, esters (e.g., methyl acetate, ethyl acetate, ethyl propionate, butyl acetate, and diethyl carbonate), alcohols (e.g., ethanol, isopropanol, butanol, and cyclohexanol), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, and 1,2-dimethoxyethane), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide), amides (e.g., dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, 1,3-dimethyl-2-imidazolidinone
- solvents it is preferable to use organic solvents, and it is more preferable to use ketones and/or esters, because this will result in a better alignment of the liquid crystal cured layer that is formed and will have improved heat resistance.
- the solvent preferably contains a high boiling point solvent having a boiling point of 130° C. or higher, because this improves the alignment property of the liquid crystal composition.
- the content of the high boiling point solvent is preferably 150 parts by mass or more, and more preferably 150 to 1000 parts by mass, relative to 100 parts by mass of the liquid crystal compound.
- 100 parts by mass of the liquid crystal compound which is the standard for the content of the high boiling point solvent, refers to 100 parts by mass of the total amount of the liquid crystal compound including the reverse dispersion compound (I) when the reverse dispersion compound (I) is a liquid crystal compound.
- the liquid crystal composition of the present invention may contain a polymerization initiator.
- the polymerization initiator is not particularly limited, but is preferably a compound having photosensitivity, that is, a photopolymerization initiator.
- a photopolymerization initiator various compounds can be used without particular limitation.
- photopolymerization initiator examples include ⁇ -carbonyl compounds, acyloin ethers, ⁇ -hydrocarbon substituted aromatic acyloin compounds, polynuclear quinone compounds, combinations of triaryl imidazole dimers and p-aminophenyl ketones, acridines, phenazine compounds, oxadiazole compounds, o-acyloxime compounds, and acylphosphine oxide compounds.
- photopolymerization initiator As such a photopolymerization initiator, commercially available products can be used, such as Irgacure-184, Irgacure-907, Irgacure-369, Irgacure-651, Irgacure-819, Irgacure-OXE-01, and Irgacure-OXE-02, all of which are manufactured by BASF.
- the content of the polymerization initiator is preferably 0.01 to 30 mass % relative to the total solid content (100 mass %) of the liquid crystal composition, and more preferably 0.1 to 10 mass %.
- optically anisotropic layer of the present invention is an optically anisotropic layer comprising a cured liquid crystal layer obtained by fixing the alignment state of the above-mentioned liquid crystal composition of the present invention.
- the orientation state of the liquid crystal compound in the liquid crystal cured layer of the present invention is preferably horizontal orientation.
- horizontal orientation means that the main surface of the liquid crystal cured layer (or, when the liquid crystal cured layer is formed on a member such as a support or an alignment film, the surface of the member) and the long axis direction of the liquid crystal compound are parallel. However, it is not required that they be strictly parallel, and in this specification, it means an orientation in which the angle between the long axis direction of the liquid crystal compound and the main surface of the liquid crystal cured layer is less than 10°.
- the optically anisotropic layer of the present invention is preferably a positive A plate.
- the positive A plate is defined as follows.
- the positive A plate satisfies the relationship of the following formula (A1):
- the positive A plate has a positive Rth value.
- the positive A plate is preferably used in combination with a positive C plate. That is, the positive C plate satisfies the relationship of the following formula (C1), where nx is the refractive index in the slow axis direction in the film plane (the direction in which the refractive index in the plane is maximum), ny is the refractive index in the direction perpendicular to the slow axis in the plane, and nz is the refractive index in the thickness direction.
- C1 the refractive index in the slow axis direction in the film plane (the direction in which the refractive index in the plane is maximum)
- ny is the refractive index in the direction perpendicular to the slow axis in the plane
- nz
- Re(550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, further preferably 130 to 150 nm, and particularly preferably 135 to 145 nm.
- ⁇ /4 plate refers to a plate having a ⁇ /4 function, specifically, a plate having the function of converting linearly polarized light of a certain wavelength into circularly polarized light (or circularly polarized light into linearly polarized light).
- the thickness of the optically anisotropic layer is preferably 0.1 to 10 ⁇ m, and more preferably 0.5 to 5 ⁇ m.
- the optically anisotropic layer of the present invention satisfies the following formula (3).
- Re(450) represents the in-plane retardation of the optically anisotropic layer at a wavelength of 450 nm
- Re(550) represents the in-plane retardation of the optically anisotropic layer at a wavelength of 550 nm.
- the optically anisotropic layer of the present invention preferably has a surface free energy of 35 mN/m or less in order to prevent wind unevenness.
- the surface free energy is preferably 24 mN/m or more.
- the surface free energy can be measured by the Kölbl-Wu method.
- the optical film of the present invention is an optical film having the optically anisotropic layer of the present invention described above.
- the structure of the optical film will be described with reference to Fig. 1.
- Fig. 1 is a schematic cross-sectional view showing an example of the optical film. It should be noted that FIG. 1 is a schematic diagram, and the thickness and positional relationships of the layers do not necessarily correspond to the actual ones, and the support and alignment film shown in FIG. 1 are both optional components.
- An optical film 10 shown in FIG. 1 comprises, in this order, a support 16, an alignment film 14, and an optically anisotropic layer 12 made of a cured liquid crystal layer obtained by fixing the alignment state of the liquid crystal composition of the present invention.
- the optically anisotropic layer 12 may be a laminate of two or more different liquid crystal cured layers.
- the optically anisotropic layer 12 is preferably a laminate of a positive A plate and a positive C plate.
- the optically anisotropic layer may be peeled off from the support and used alone as an optical film.
- the optical film may have a support as a base material for forming an optically anisotropic layer.
- a support is preferably transparent. Specifically, it is preferable that the light transmittance of the support is 80% or more.
- Such supports include, for example, glass substrates and polymer films.
- materials for polymer films include cellulose-based polymers; acrylic-based polymers having acrylic acid ester polymers such as polymethyl methacrylate and lactone ring-containing polymers; thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene-based polymers such as polystyrene and acrylonitrile-styrene copolymers (AS resins); polyolefin-based polymers such as polyethylene, polypropylene, and ethylene-propylene copolymers; vinyl chloride-based polymers; amide-based polymers such as nylon and aromatic polyamides; imide-based polymers; sulfone-based polymers; polyethersulfone-based polymers; polyetheretherketone-based polymers; polyphenylene sulfide-based polymers; vinylidene chloride-
- the thickness of the support is not particularly limited, but is preferably 5 to 100 ⁇ m, and more preferably 5 to 50 ⁇ m.
- the support may be peelable from the optical film.
- the optically anisotropic layer is preferably formed on the surface of the alignment film.
- the alignment film may be sandwiched between the support and the optically anisotropic layer.
- the above-mentioned support may also serve as the alignment film.
- the alignment film may be peelable from the optical film.
- the alignment film may have optical anisotropy, and a positive C plate having an alignment function on its surface as shown in WO2021/166619 may be used as the alignment film.
- the alignment film may be any film that has the function of aligning the polymerizable liquid crystal compound contained in the composition.
- Alignment layers are generally made mainly of polymers. Polymer materials for alignment layers are described in many publications and many commercial products are available.
- the polymer material for the alignment film is preferably polyvinyl alcohol, polyimide, or any of their derivatives, and more preferably modified or unmodified polyvinyl alcohol.
- the photo-alignment film is not particularly limited, and examples that can be used include an alignment film formed from a polymer material such as a polyamide compound and a polyimide compound described in paragraphs [0024] to [0043] of International Publication No. 2005/096041; a liquid crystal alignment film formed from a liquid crystal alignment agent having a cinnamoyl group described in JP-A-2012-155308; and a product name LPP-JP265CP manufactured by Rolic Technologies.
- the thickness of the alignment film is not particularly limited, but from the viewpoint of mitigating surface irregularities that may exist on the support and forming a liquid crystal cured layer with a uniform thickness, the thickness is preferably 0.01 to 10 ⁇ m, more preferably 0.01 to 1 ⁇ m, and even more preferably 0.01 to 0.5 ⁇ m.
- the optically anisotropic layer of the present invention may be formed on the surface of another liquid crystal cured layer, or another liquid crystal cured layer may be formed on the surface of the optically anisotropic layer of the present invention.
- the liquid crystal cured layer include a liquid crystal cured layer obtained by fixing the above-mentioned liquid crystal composition of the present invention in a desired alignment state, and a liquid crystal cured layer (light absorption anisotropic film) obtained by fixing the alignment state of a composition containing the above-mentioned liquid crystal compound, a polymerization initiator, a dichroic material, a surfactant, a solvent, etc.
- the optical film may contain an ultraviolet (UV) absorbing agent in consideration of the influence of external light (particularly ultraviolet light).
- the ultraviolet absorbing agent may be contained in the optically anisotropic layer, or may be contained in a member other than the optically anisotropic layer constituting the optical film.
- a suitable example of the member other than the optically anisotropic layer is the support.
- Any conventionally known ultraviolet absorbent capable of expressing ultraviolet absorbing properties can be used as the ultraviolet absorbing agent.
- benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorbing agents are preferred from the viewpoint of obtaining ultraviolet absorbing ability (ultraviolet absorbing ability) that is high and is used in image display devices.
- Ultraviolet absorbing agents that can be used include Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, and Tinuvin 1577 (all manufactured by BASF).
- the polarizing plate of the present invention has the above-mentioned optically anisotropic layer or optical film of the present invention and a polarizer.
- the polarizing plate of the present invention preferably further has a positive C plate, and more preferably has a positive C plate formed by fixing the alignment state of a liquid crystal composition containing a surfactant (II) having a structure represented by the above-mentioned formula (2).
- the angle between the slow axis of the positive A plate and the absorption axis of a polarizer described later is preferably 30 to 60°, more preferably 40 to 50°, even more preferably 42 to 48°, and particularly preferably 45°.
- the “slow axis” refers to the direction in the plane of the cured liquid crystal layer in which the refractive index is maximum
- the “absorption axis" of the polarizer refers to the direction in which the absorbance is highest.
- the absolute value of the angle between the in-plane slow axis of the second region in which the orientation state of the homogeneously oriented liquid crystal compound is fixed and the absorption axis of the polarizer is preferably 5 to 25°, and more preferably 10 to 20°, in terms of enabling the optically anisotropic layer A to be suitably applied to a circular polarizing plate or the like.
- the polarizing plate can also be used as an optical compensation film in an IPS or FFS liquid crystal display device.
- the above-mentioned optically anisotropic layer is at least one plate of a laminate of a positive A plate and a positive C plate, and the angle between the slow axis of the positive A plate layer and the absorption axis of a polarizer described later is perpendicular or parallel, and more preferably, the angle between the slow axis of the positive A plate layer and the absorption axis of a polarizer described later is 0 to 5° or 85 to 95°.
- the angle between the slow axis of the cured liquid crystal layer and the absorption axis of the polarizer described later is preferably parallel or perpendicular.
- parallel does not require that they be strictly parallel, but means that the angle between one and the other is less than 10°.
- orthogonal does not require that they be strictly orthogonal, but means that the angle between one and the other is more than 80° and less than 100°.
- the polarizer is not particularly limited as long as it is a member having a function of converting light into a specific linearly polarized light, and a conventionally known absorptive polarizer and reflective polarizer, or a coating type polarizer can be used.
- absorption-type polarizers include iodine-based polarizers, dye-based polarizers using a dichroic dye, and polyene-based polarizers.
- Iodine-based polarizers and dye-based polarizers include coating-type polarizers and stretching-type polarizers, and either can be used, but a polarizer produced by adsorbing iodine or a dichroic dye to polyvinyl alcohol and stretching it is preferable.
- coating-type polarizers include polarizers containing a cured product of a liquid crystal compound and a dichroic dye.
- the reflective polarizer a polarizer in which thin films with different birefringence are laminated, a wire grid type polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection region is combined with a quarter-wave plate, and the like are used.
- the thickness of the polarizer is not particularly limited, but is preferably 3 to 60 ⁇ m, more preferably 3 to 30 ⁇ m, and even more preferably 3 to 10 ⁇ m.
- a pressure-sensitive adhesive layer may be disposed between the optically anisotropic layer in the optical film and the polarizer.
- pressure-sensitive adhesives include, but are not limited to, polyvinyl alcohol-based pressure-sensitive adhesives.
- an adhesive layer may be disposed between the optically anisotropic layer and the polarizer in the optical film.
- the adhesive layer used for laminating the cured product and the polarizer is preferably a curable adhesive composition that is cured by irradiation with active energy rays or by heating.
- the curable adhesive composition include a curable adhesive composition containing a cationically polymerizable compound, and a curable adhesive composition containing a radically polymerizable compound.
- the thickness of the adhesive layer is preferably 0.01 to 20 ⁇ m, more preferably 0.01 to 10 ⁇ m, and even more preferably 0.05 to 5 ⁇ m.
- the thickness of the adhesive layer is within this range, no lifting or peeling occurs between the laminated protective layer or liquid crystal cured layer and the polarizer, and adhesive strength that is practically problem-free is obtained.
- the thickness of the adhesive layer is preferably 0.4 ⁇ m or more.
- the polarizing plate of the present invention may have an easy-adhesion layer disposed between the optically anisotropic layer and the polarizer in the optical film.
- the easy-adhesion layer preferably has a storage modulus of 1.0 ⁇ 10 6 Pa to 1.0 ⁇ 10 7 Pa at 85° C.
- Constituent materials for the easy-adhesion layer include polyolefin-based components and polyvinyl alcohol-based components.
- the thickness of the easy-adhesion layer is preferably 500 nm to 1 ⁇ m.
- paragraphs [0048] to [0053] of JP2018-36345A can be referred to, the contents of which are incorporated herein by reference.
- the image display device of the present invention is an image display device having the optical film of the present invention or the polarizing plate of the present invention.
- the display element used in the image display device is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as "EL (Electro Luminescence)”) display panel, and a plasma display panel. Among these, a liquid crystal cell and an organic EL display panel are preferred.
- a liquid crystal display device which is an example of an image display device, is a liquid crystal display device having the above-mentioned polarizing plate and a liquid crystal cell.
- the polarizing plates provided on both sides of the liquid crystal cell, it is preferable to use the above-mentioned polarizing plate as the front-side polarizing plate, and it is more preferable to use the above-mentioned polarizing plate as the front-side and rear-side polarizing plates.
- the liquid crystal cell used in the liquid crystal display device is preferably in VA (Vertical Alignment) mode, OCB (Optically Compensated Bend) mode, IPS (In-Plane-Switching) mode, FFS (Fringe-Field-Switching) mode, or TN (Twisted Nematic) mode, but is not limited to these.
- VA Vertical Alignment
- OCB Optically Compensated Bend
- IPS In-Plane-Switching
- FFS Ringe-Field-Switching
- TN Transmission Nematic
- An organic EL display device which is an example of an image display device, may include, from the viewing side, a polarizer, a ⁇ /4 plate made of the above-mentioned liquid crystal cured layer (optically anisotropic layer), and an organic EL display panel.
- the embodiments may have the above order.
- An organic EL display panel is a display panel configured using organic EL elements in which an organic light-emitting layer (organic electroluminescence layer) is sandwiched between electrodes (cathode and anode).
- the configuration is not particularly limited, and a known configuration may be adopted.
- the dope prepared above was cast using a drum film-forming machine.
- the dope was cast from a die onto a metal support cooled to 0° C., and then the resulting web (film) was peeled off from the drum.
- the drum was made of SUS (stainless steel).
- the web (film) obtained by casting was peeled off from the drum, and then dried for 20 minutes in a tenter apparatus, which clipped both ends of the web with clips while transporting the film at 30 to 40° C.
- the web was then post-dried by zone heating while being transported with rolls.
- the web obtained was knurled and then wound up to obtain cellulose acylate film A1.
- the obtained cellulose acylate film A1 had a thickness of 40 ⁇ m, an in-plane retardation Re(550) at a wavelength of 550 nm of 1 nm, and a retardation in the thickness direction Rth(550) at a wavelength of 550 nm of 25 nm.
- the coating solution E1 for forming a photo-alignment film having the following composition was continuously applied onto the above-mentioned cellulose acylate film A1 using a wire bar.
- the cellulose acylate film A1 on which the coating film was formed was dried with hot air at 140° C. for 120 seconds, and then the coating film was irradiated with polarized ultraviolet light (10 mJ/cm 2 , using an ultra-high pressure mercury lamp) to form a photo-alignment film E1 with a thickness of 0.7 ⁇ m, thereby obtaining a TAC film with a photo-alignment film.
- Coating liquid E1 for forming photo-alignment film ⁇ Polymer PA-2 (listed below) 100.00 parts by weight Thermal cationic polymerization initiator PAG-1 (listed below) 5.00 parts by weight Acid generator CPI-110TF (listed below) 0.005 parts by weight Isopropyl alcohol 16.50 parts by weight Acetic acid Butyl 1,072.00 parts by mass, methyl ethyl ketone 268.00 parts by mass
- Polymer PA-2 (Weight average molecular weight: 45,000. In the following formula, the numerical value for each repeating unit indicates the content (mass%) of each repeating unit relative to the total repeating units.)
- Composition F1-1 having the following composition was applied onto the photo-alignment film E1 using a bar coater.
- the coating film formed on the photo-alignment film E1 was heated to 120°C with hot air, and then cooled to 60°C.
- the coating film was then irradiated with 100 mJ/ cm2 ultraviolet light at a wavelength of 365 nm using a high-pressure mercury lamp under a nitrogen atmosphere, and then irradiated with 500 mJ/ cm2 ultraviolet light while heating to 120°C, thereby fixing the alignment of the liquid crystal compound, and producing an optical film F1-1 having an optically anisotropic layer F1-1.
- the optically anisotropic layer F1-1 had a thickness of 2.9 ⁇ m and an Re(550) of 142 nm.
- the optically anisotropic layer F1-1 satisfied the relationship Re(450) ⁇ Re(550) ⁇ Re(650). Re(450)/Re(550) was 0.82.
- the optically anisotropic layer corresponds to a so-called ⁇ /4 plate.
- the mixture of reverse dispersion compounds LA-1 to LA-3 and polymerizable liquid crystal compounds LC-1 to LC-4 contained in the following composition F1-1 is referred to as liquid crystal mixture A.
- composition F1-1 ⁇ 30.00 parts by mass of the following reverse dispersion compound LA-1 30.00 parts by mass of the following reverse dispersion compound LA-2 27.00 parts by mass of the following reverse dispersion compound LA-3 27.00 parts by mass of the following polymerizable liquid crystal compound LC- 1 6.64 parts by weight of the following polymerizable liquid crystal compound LC-2 1.20 parts by weight of the following polymerizable liquid crystal compound LC-3 0.16 parts by weight of the following polymerizable liquid crystal compound LC-4 5.00 parts by weight of the following Polymerization initiator PI-1 0.50 parts by mass; surfactant mainly composed of polyacrylate compound (BYK-361N, manufactured by BYK Japan) 0.09 parts by mass; cyclopentanone 181.00 parts by mass; methyl ethyl ketone 54 .00 parts by mass---------------------------------------------------------------------------------------------------------------------------------------------
- Reverse dispersion compound LA-1 (tBu represents a tertiary butyl group)
- a coating solution FC-1 for forming a positive C plate having the following composition was applied onto the above-mentioned cellulose acylate film A1, and the resulting coating film was aged at 60° C. for 60 seconds. Thereafter, the coating film was irradiated with ultraviolet light at 1000 mJ/cm 2 using an air-cooled metal halide lamp (manufactured by Eye Graphics Co., Ltd.) at 70 mW/cm 2 under air to fix the alignment state, thereby vertically aligning the liquid crystal compound, and thus a positive C plate FC-1 having a thickness of 0.5 ⁇ m was produced.
- the Rth(550) of the obtained positive C plate was ⁇ 60 nm.
- Polymer M (weight average molecular weight: 60,000, the value in each repeating unit indicates the content relative to the total repeating units)
- a roll-shaped polyvinyl alcohol film was stretched in a machine direction (MD) in an aqueous iodine solution and dried to obtain a polarizer 1 having a thickness of 14 ⁇ m.
- the above polarizer protective films were attached to both surfaces of the above polarizer 1 with a PVA adhesive to prepare a polarizer 1 with protective films.
- UV adhesive 1 having the following composition was prepared.
- ⁇ UV adhesive 1 ⁇ ⁇ CEL2021P manufactured by Daicel Corporation 70 parts by mass ⁇ 1,4-butanediol diglycidyl ether 20 parts by mass ⁇ 2-ethylhexyl glycidyl ether 10 parts by mass ⁇ CPI-100P 2.25 parts by mass ⁇
- Adhesive Sheet N1 95 parts by mass of butyl acrylate and 5 parts by mass of acrylic acid were polymerized by a solution polymerization method to obtain an acrylic copolymer 1 having an average molecular weight of 2,000,000 and a molecular weight distribution (Mw/Mn) of 3.0.
- a solution (adhesive composition N1) was prepared by mixing 100 parts by mass of the solid content of acrylic copolymer 1 with 10 parts by mass of a polyfunctional acrylate monomer (Aronix M-315, manufactured by Toa Gosei Co., Ltd.), 1 part by mass of a photopolymerization initiator (Irgacure 500, manufactured by BASF Corporation), 1 part by mass of trimethylolpropane tolylene diisocyanate (Coronate L, manufactured by Nippon Polyurethane Industry Co., Ltd.), and 0.2 parts by mass of a silane coupling agent (KBM-403, manufactured by Shin-Etsu Chemical Co., Ltd.).
- a polyfunctional acrylate monomer (Aronix M-315, manufactured by Toa Gosei Co., Ltd.)
- a photopolymerization initiator Irgacure 500, manufactured by BASF Corporation
- Trimethylolpropane tolylene diisocyanate Coreonate L, manufactured by
- the prepared adhesive composition N1 was applied onto a silicone resin-coated PET film (release film), dried at 90° C. to remove the solvent, and irradiated with ultraviolet (UV) rays under the following conditions to prepare an adhesive sheet N1 having an adhesive layer N1 with a thickness of 20 ⁇ m.
- the storage modulus of the adhesive layer N1 was 0.6 MPa.
- the UV illuminance and light quantity were measured using "UVPF-36" manufactured by Eye Graphics.
- the above-prepared polarizer with protective film 1 was bonded to the optically anisotropic layer (positive A plate) side of the above-mentioned optically anisotropic layer-attached film 1 using the above-mentioned adhesive sheet N1, and the cellulose acylate film A1 on the positive C plate side was removed to complete a circular polarizing plate.
- the polarizer was attached so that the absorption axis of the polarizer included in the polarizer with protective film 1 and the slow axis of the positive A plate F1-1 included in the film with optically anisotropic layer 1 formed an angle of 45°.
- a SAMSUNG GALAXY S4 equipped with an organic EL panel (organic EL display element) was disassembled, a touch panel with a circular polarizer was peeled off from the organic EL display device, and the circular polarizer was peeled off from the touch panel to isolate the organic EL display element, the touch panel, and the circular polarizer.
- the isolated touch panel was then bonded again to the organic EL display element, and the above-prepared circular polarizer was bonded to the touch panel via an adhesive SK2057 (manufactured by Soken Chemical Industries, Ltd.) so that the optically anisotropic layer side (positive C plate side) was on the panel side, thereby preparing an organic EL display device.
- Optical films F1-2 to F1-20 were produced in the same manner as in Comparative Example 1-1, except that the amount of surfactant BYK-361N (manufactured by BYK Japan) (i.e., a surfactant not corresponding to surfactant (II)) used in the production of optical film F1-1 in Comparative Example 1-1 was changed as shown in Table 11 below, or the surfactant BYK-361N was replaced with specific surfactants SA-1 to SA-14 corresponding to surfactant (II) shown in Table 11 below.
- BYK-361N manufactured by BYK Japan
- Examples 3-1 to 3-3 Circularly polarizing plates and organic EL display devices of Examples 3-1 to 3-3, which are also shown in Table 13 below, were produced in the same manner as in Comparative Example 1-1, except that optical films F3-1 to F3-3 produced by the following methods were used instead of the optical film F1-1.
- An optical film F3-1 having an optically anisotropic layer F3-1 was prepared in the same manner as for the optical film F1-1, except that the composition F1-1 used in the preparation of the optical film F-1 was changed to the following composition F3-1.
- a mixture of reverse dispersion compounds LA-1 and LA-4 to LA-7 and polymerizable liquid crystal compound LC-4 shown in the following composition F3-1 is designated as liquid crystal mixture C.
- composition F3-1 The reverse dispersion compound LA-1 above: 26.0 parts by mass
- the reverse dispersion compound LA- 6 5.0 parts by mass; the following reverse dispersion compound LA-7 12.0 parts by mass; the above polymerizable liquid crystal compound LC-4 13.0 parts by mass; the following polymerization initiator PI-1 0.5 parts by mass; Activator SA-1 0.06 parts by mass, tetrahydrofuran 240.0 parts by mass, cyclopentanone 60.0 parts by mass ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------
- Example 4-1 to 4-11 Circularly polarizing plates and organic EL display devices of Examples 4-1 to 4-11 were produced in the same manner as in Comparative Example 1-1, except that optical films F4-1 to F4-11 produced by the following method were used instead of the optical film F1-1.
- An optical film F4-1 having an optically anisotropic layer F4-1 was prepared in the same manner as for the optical film F1-1, except that the composition F1-1 used in the preparation of the optical film F-1 was changed to the following composition F4-1.
- a mixture of reverse dispersion compounds LA-8 and LA-9, and polymerizable liquid crystal compound LC-5 shown in the following composition F4-1 is designated as liquid crystal mixture F.
- Optical films F4-2 to F4-9 were produced in the same manner as for optical film F4-1, except that the specific surfactant SA-7 was changed to the type of surfactant shown in Table 15 below.
- An optical film F4-10 was produced in the same manner as in the optical film F4-1, except that the composition F4-1 was changed to the following composition F4-10.
- a mixture of reverse dispersion compounds LA-8 and LA-9 and polymerizable liquid crystal compound LC-5 shown in the following composition F4-10 is designated as liquid crystal mixture F, similarly to the above composition F4-1.
- An optical film F4-11 was produced in the same manner as in the optical film F4-1, except that the composition F4-1 was changed to the following composition F4-11.
- a mixture of reverse dispersion compounds LA-10 and LA-11 shown in the following composition F4-11 is designated as liquid crystal mixture G.
- composition F4-11 ⁇ 99.97 parts by mass of the reverse dispersion compound LA-10 shown below 0.03 parts by mass of the reverse dispersion compound LA-11 shown below 0.50 parts by mass of the polymerization initiator PI-1 shown above 0.50 parts by mass of the surfactant SA-7 shown above .06 parts by mass, cyclopentanone 181.00 parts by mass, methyl ethyl ketone 54.00 parts by mass ⁇
- an optical film having an optically anisotropic layer obtained by fixing the alignment state of a liquid crystal composition containing a reverse dispersion compound having a group (aromatic ring) represented by the above formula (Ar-3) has poor alignment properties. This is presumably because the group (aromatic ring) represented by the above formula (Ar-3) has strong interactions such as ⁇ - ⁇ interactions, resulting in low liquid crystal fluidity and slow alignment.
- Optical film 12 Liquid crystal cured layer (optically anisotropic layer) 14 Orientation film 16 Support
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| CN202480029980.XA CN121057967A (zh) | 2023-05-19 | 2024-05-17 | 液晶组合物、光学各向异性层、光学膜、偏振片及图像显示装置 |
| US19/370,840 US20260049245A1 (en) | 2023-05-19 | 2025-10-28 | Liquid crystal composition, optically anisotropic layer, optical film, polarizing plate, and image display device |
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| WO2025143020A1 (ja) * | 2023-12-27 | 2025-07-03 | 富士フイルム株式会社 | 液晶組成物、光吸収異方性膜、積層体及び画像表示装置 |
| WO2026071208A1 (ja) * | 2024-09-30 | 2026-04-02 | 積水化学工業株式会社 | 共重合体ポリマー |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007033712A (ja) * | 2005-07-25 | 2007-02-08 | Fujifilm Corp | 光学フィルムおよびこれを用いた偏光板、液晶表示装置 |
| WO2016114047A1 (ja) * | 2015-01-13 | 2016-07-21 | Dic株式会社 | 重合性液晶組成物及び該組成物を用いて作製した光学異方体、位相差膜、反射防止膜、液晶表示素子 |
| WO2017057020A1 (ja) * | 2015-09-30 | 2017-04-06 | Dic株式会社 | 重合性組成物及びそれを用いた光学異方体 |
| WO2018003653A1 (ja) * | 2016-06-27 | 2018-01-04 | Dic株式会社 | 重合性液晶組成物、それを用いた光学異方体及び液晶表示素子 |
| WO2020218104A1 (ja) * | 2019-04-26 | 2020-10-29 | 住友化学株式会社 | 液晶硬化膜形成用組成物及びその用途 |
| WO2023276611A1 (ja) * | 2021-06-28 | 2023-01-05 | 富士フイルム株式会社 | 偏光板の製造方法、有機エレクトロルミネッセンス表示装置の製造方法、偏光板、有機エレクトロルミネッセンス表示装置、液晶表示装置 |
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| JP6427340B2 (ja) | 2013-09-11 | 2018-11-21 | 富士フイルム株式会社 | 光学異方性層とその製造方法、積層体とその製造方法、偏光板、液晶表示装置及び有機el表示装置 |
| JP7033043B2 (ja) | 2018-09-28 | 2022-03-09 | 富士フイルム株式会社 | 光学積層体、液晶表示装置および有機電界発光装置 |
| JP2021152641A (ja) | 2020-03-19 | 2021-09-30 | 住友化学株式会社 | 円偏光板及び光学積層体 |
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007033712A (ja) * | 2005-07-25 | 2007-02-08 | Fujifilm Corp | 光学フィルムおよびこれを用いた偏光板、液晶表示装置 |
| WO2016114047A1 (ja) * | 2015-01-13 | 2016-07-21 | Dic株式会社 | 重合性液晶組成物及び該組成物を用いて作製した光学異方体、位相差膜、反射防止膜、液晶表示素子 |
| WO2017057020A1 (ja) * | 2015-09-30 | 2017-04-06 | Dic株式会社 | 重合性組成物及びそれを用いた光学異方体 |
| WO2018003653A1 (ja) * | 2016-06-27 | 2018-01-04 | Dic株式会社 | 重合性液晶組成物、それを用いた光学異方体及び液晶表示素子 |
| WO2020218104A1 (ja) * | 2019-04-26 | 2020-10-29 | 住友化学株式会社 | 液晶硬化膜形成用組成物及びその用途 |
| WO2023276611A1 (ja) * | 2021-06-28 | 2023-01-05 | 富士フイルム株式会社 | 偏光板の製造方法、有機エレクトロルミネッセンス表示装置の製造方法、偏光板、有機エレクトロルミネッセンス表示装置、液晶表示装置 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2025143020A1 (ja) * | 2023-12-27 | 2025-07-03 | 富士フイルム株式会社 | 液晶組成物、光吸収異方性膜、積層体及び画像表示装置 |
| WO2026071208A1 (ja) * | 2024-09-30 | 2026-04-02 | 積水化学工業株式会社 | 共重合体ポリマー |
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| CN121057967A (zh) | 2025-12-02 |
| JPWO2024242041A1 (https=) | 2024-11-28 |
| KR20250168388A (ko) | 2025-12-02 |
| US20260049245A1 (en) | 2026-02-19 |
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