WO2021060428A1 - 重合性液晶組成物、化合物、光学異方性膜、光学フィルム、偏光板および画像表示装置 - Google Patents

重合性液晶組成物、化合物、光学異方性膜、光学フィルム、偏光板および画像表示装置 Download PDF

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WO2021060428A1
WO2021060428A1 PCT/JP2020/036159 JP2020036159W WO2021060428A1 WO 2021060428 A1 WO2021060428 A1 WO 2021060428A1 JP 2020036159 W JP2020036159 W JP 2020036159W WO 2021060428 A1 WO2021060428 A1 WO 2021060428A1
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group
carbon atoms
liquid crystal
atom
compound
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French (fr)
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有次 吉田
渡辺　徹
慶太 高橋
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Fujifilm Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
    • C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation

Definitions

  • the present invention relates to a polymerizable liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device.
  • a polymerizable liquid crystal compound exhibiting reverse wavelength dispersibility has features such as being able to accurately convert light wavelengths over a wide wavelength range and being able to thin a retardation film due to its high refractive index. Because it has, it is being actively researched. Further, as a polymerizable liquid crystal compound exhibiting inverse wavelength dispersibility, a T-type molecular design guideline is generally taken, the wavelength of the major axis of the molecule is shortened, and the wavelength of the minor axis located at the center of the molecule is the longer wavelength. Is required to be.
  • a hydrophilic nitrogen atom, oxygen atom, and sulfur atom are formed on the short axis skeleton (hereinafter, also referred to as “reverse wavelength dispersion expression part”). Is known to be introduced (see, for example, Patent Documents 1 to 3).
  • Patent Documents 1 to 3 As a result of examining Patent Documents 1 to 3, the present inventors have found that the birefringence index changes when the formed optically anisotropic film is exposed to high temperature and high humidity (hereinafter, "" It was clarified that there was a problem of "wet and heat durability”. Further, the present inventors have described in Patent Documents 1 to 3 that the optically anisotropic film formed has a durability in which the birefringence is changed by ammonia, which is a basic nucleophile (hereinafter, "" It was confirmed that there was a problem of "amine resistance”.
  • the present invention provides a polymerizable liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device used for forming an optically anisotropic film having excellent wet heat durability and amine resistance.
  • the task is to do.
  • the present inventors have formed a polymerizable liquid crystal composition by using a polymerizable liquid crystal composition containing a compound represented by the formula (I-1) described later together with the polymerizable liquid crystal compound.
  • the present invention has been completed by finding that the moist heat durability and amine resistance of the optically anisotropic film to be obtained are improved. That is, it was found that the above-mentioned problems can be achieved by the following configuration.
  • Ar 1 and Ar 2 in the formula (I-1) described later are any aromatics selected from the group consisting of the groups represented by the formulas (Ar-1) to (Ar-7) described later.
  • a polymerizable liquid crystal composition a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device used for forming an optically anisotropic film having excellent wet heat durability and amine resistance. can do.
  • FIG. 1A is a schematic cross-sectional view showing an example of the optical film of the present invention.
  • FIG. 1B is a schematic cross-sectional view showing an example of the optical film of the present invention.
  • FIG. 1C is a schematic cross-sectional view showing an example of the optical film of the present invention.
  • the present invention will be described in detail.
  • the description of the constituent elements described below may be based on a typical embodiment of the present invention, but the present invention is not limited to such an embodiment.
  • the numerical range represented by using "-" means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
  • a substance corresponding to each component may be used alone or in combination of two or more.
  • the content of the component means the total content of the substances used in combination unless otherwise specified.
  • the bonding direction of the divalent group (for example, -CO-NR-) described is not particularly limited unless the bonding position is specified, and for example, the formula (for example) described later will be used.
  • X 1 in I-1) is -CO-NR-, assuming that the position bonded to the L 1 side is * 1 and the position bonded to the Ar 1 side is * 2, X 1 is It may be * 1-CO-NR- * 2 or * 1-NR-CO- * 2.
  • the polymerizable liquid crystal composition of the present invention includes a polymerizable liquid crystal compound having reverse wavelength dispersibility (hereinafter, also abbreviated as “reverse wavelength dispersible liquid crystal compound”) and a compound represented by the formula (I-1) described later. (Hereinafter, also abbreviated as "specific compound”), which is a polymerizable liquid crystal composition.
  • reverse wavelength dispersible liquid crystal compound a polymerizable liquid crystal compound having reverse wavelength dispersibility
  • specific compound which is a polymerizable liquid crystal composition.
  • the optically anisotropic film formed has good moist heat durability and amine resistance.
  • the linking groups (X 1 and X 2 ) that bond with the aromatic rings (Ar 1 and Ar 2 ) having a maximum absorption wavelength at 280 to 420 nm are strong without an ester bond. It is considered that the hydrolysis resistance of the specific compound was improved due to the strong bond, and as a result, both the wet heat durability and the amine resistance were improved.
  • linking groups (L 1 and L 2 ) of the linking groups (X 1 and X 2 ) and the polymerizable group-containing groups (Mes 1 and Mes 2 ) in the formula (I-1) described later are repeated as predetermined. It is considered that the alkylene group having a number improves the compatibility between the specific compound and the inverse wavelength dispersible liquid crystal compound, and as a result, the effect of improving the wet heat durability and the amine resistance is easily exhibited.
  • each component of the polymerizable liquid crystal composition of the present invention will be described in detail.
  • the specific compound contained in the polymerizable liquid crystal composition of the present invention is a compound represented by the following formula (I-1).
  • Ar 1 and Ar 2 each independently represent an aromatic ring having a maximum absorption wavelength of 280 to 420 nm.
  • R 1 ⁇ R 5 are each independently a hydrogen atom, a fluorine atom or a carbon atoms Represents 1 to 4 alkyl groups.
  • p represents 0 or 1.
  • X 1 and X 2 independently represent -O-, -S-, -CO-, -CO-NR 6- , or a single bond
  • R 6 Independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • p represents 0 or 1 as described above, but it is 0, that is, D 1 and Ar 2 in the above formula (I-1) do not exist. Is preferable.
  • R 1 , R 2 and R 5 independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms. Of these, any of -CO-, -O-, and -CO-O- is preferable.
  • X 1 and X 2 are preferably —O— or —S— for the reason that the wet and heat durability of the optically anisotropic film to be formed becomes better. It is more preferably O-.
  • Ar 1 and Ar 2 represent an aromatic ring having a maximum absorption wavelength at 280 to 420 nm as described above, but the optical anisotropic film formed has better light resistance. For this reason, it is preferable to represent an aromatic ring having a maximum absorption wavelength of 300 to 400 nm.
  • the maximum absorption wavelength refers to the maximum absorption wavelength in the absorption spectrum measured by the following method using a compound in which the linking group (X 1 and X 2) with the aromatic ring is replaced with a methyl group. ⁇ Measurement method> The compound is dissolved in chloroform to prepare a solution having a concentration of 1% by mass.
  • the prepared solution is placed in a quartz cell (10 mm long square cell), and the absorbance in the wavelength range of 200 to 800 nm of the solution is measured using an ultraviolet visible infrared spectrophotometer U-3100PC (Shimadzu Seisakusho). .. Next, the maximum absorption wavelength is obtained in the obtained absorption spectrum.
  • Ar 1 and Ar 2 are represented by the following formulas (Ar-1) to (Ar-7) for the reason that the compatibility with the inverse wavelength dispersible liquid crystal compound is good. It preferably represents any aromatic ring selected from the group consisting of groups.
  • * represents the bonding position with X 1 or D 1 for Ar 1 , and the bonding position with D 1 or X 2 for Ar 2. However, when p is 0, it represents the bonding position with X 1 or X 2.
  • Q 1 represents N or CH
  • Q 2 represents -S-, -O-, or -N (R 7 )-
  • R 7 is a hydrogen atom or Representing an alkyl group having 1 to 6 carbon atoms
  • Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent. Represent.
  • alkyl group having 1 to 6 carbon atoms indicated by R 7 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl.
  • Examples include a group, an n-pentyl group, and an n-hexyl group.
  • aromatic hydrocarbon group having 6 to 12 carbon atoms indicated by Y 1 include an aryl group such as a phenyl group, a 2,6-diethylphenyl group and a naphthyl group.
  • Examples of the aromatic heterocyclic group having 3 to 12 carbon atoms indicated by Y 1 include heteroaryl groups such as a thienyl group, a thiazolyl group, a frill group and a pyridyl group.
  • Examples of the substituent that Y 1 may have include an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group and an alkenyl.
  • Examples thereof include a group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group, and an N-alkylcarbamate group.
  • Atomic is preferred.
  • the alkyl group is preferably a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, and an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group, n).
  • alkoxy group an alkoxy group having 1 to 18 carbon atoms is preferable, an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group, etc.) is more preferable, and an alkoxy group having 1 carbon number is preferable.
  • Alkoxy groups of ⁇ 4 are more preferable, and methoxy groups or ethoxy groups are particularly preferable.
  • the alkoxycarbonyl group include a group in which an oxycarbonyl group (—O—CO— group) is bonded to the alkyl group exemplified above, and among them, a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group or an isopropoxy.
  • a carbonyl group is preferred, and a methoxycarbonyl group is more preferred.
  • alkylcarbonyloxy group examples include a group in which a carbonyloxy group (-CO-O- group) is bonded to the alkyl group exemplified above, and among them, a methylcarbonyloxy group, an ethylcarbonyloxy group, and an n-propylcarbonyloxy group.
  • a group or an isopropylcarbonyloxy group is preferable, and a methylcarbonyloxy group is more preferable.
  • the halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a fluorine atom or a chlorine atom is preferable.
  • Z 1 , Z 2 and Z 3 are independently hydrogen atoms, monovalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and carbon.
  • a monovalent alicyclic hydrocarbon group of number 3 to 20, a monovalent aromatic hydrocarbon group of 6 to 20 carbons, a halogen atom, a cyano group, a nitro group, -OR 8 , -NR 9 R 10 , or , -SR 11 and R 8 to R 11 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. Good.
  • an alkyl group having 1 to 15 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and specifically, a methyl group and an ethyl group.
  • Isopropyl group, tert-pentyl group (1,1-dimethylpropyl group), tert-butyl group, 1,1-dimethyl-3,3-dimethyl-butyl group are more preferable, and methyl group, ethyl group, tert-butyl group. Groups are particularly preferred.
  • Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include 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.
  • Monocyclic saturated hydrocarbon groups such as groups; cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclodecenyl group, cyclopentadienyl group, cyclohexadienyl group, cyclooctadienyl group, cyclodeca Monocyclic unsaturated hydrocarbon groups such as diene; bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, tricyclo [5.2.1.0 2,6 ] decyl group, Tricyclo [3.3.1.1 3,7 ] decyl group, tetracyclo [6.2.1.1 3,6 .
  • Polycyclic saturated hydrocarbon groups such as dodecyl group and adamantyl group; and the like.
  • Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, a biphenyl group and the like, and have 6 to 12 carbon atoms.
  • Aryl groups (particularly phenyl groups) are preferred.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and among them, a fluorine atom, a chlorine atom and a bromine atom are preferable.
  • alkyl group having 1 to 6 carbon atoms indicated by R 8 to R 11 specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group and a sec-butyl group.
  • examples include groups, tert-butyl groups, n-pentyl groups, n-hexyl groups and the like.
  • a 1 and A 2 are independently derived from -O-, -N (R 12 )-, -S-, and -CO-, respectively.
  • R 12 represents a hydrogen atom or a substituent.
  • Examples of the substituent represented by R 12 include the same substituents that Y 1 in the above formula (Ar-1) may have.
  • X represents a non-metal atom of Groups 14 to 16 to which a hydrogen atom or a substituent may be bonded.
  • RC1 represents a hydrogen atom or a substituent. ] Can be mentioned.
  • substituents 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, and an alkyl group.
  • substituents include a carbonyl group, a sulfo group and a hydroxyl group.
  • R 2 -, - CR 3 CR 4 -, - NR 5 -, or a divalent linking group formed from these two or more thereof,
  • R 1 ⁇ R 5 are each independently a hydrogen atom, It represents a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
  • examples of the divalent linking group include those similar to those described in D 1 in the above formula (I-1).
  • SP 1 and SP 2 are independently single-bonded, linear or branched alkylene groups having 1 to 12 carbon atoms, or directly having 1 to 12 carbon atoms.
  • Examples of the substituent include the same substituents that Y 1 in the above formula (Ar-1) may have.
  • examples of the linear or branched alkylene group having 1 to 12 carbon atoms 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. Is preferably mentioned.
  • L 3 and L 4 each independently represent a monovalent organic group.
  • the monovalent organic group include an alkyl group, an aryl group, and a heteroaryl group.
  • the alkyl group may be linear, branched or cyclic, but linear is preferred.
  • the number of carbon atoms of 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 monocyclic is preferable.
  • the aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 10 carbon atoms.
  • the heteroaryl group may be monocyclic or polycyclic.
  • the number of heteroatoms constituting the heteroaryl group is preferably 1 to 3.
  • the hetero atom constituting the heteroaryl group is preferably a nitrogen atom, a sulfur atom, or an oxygen atom.
  • the heteroaryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms.
  • the alkyl group, the aryl group and the heteroaryl group may be unsubstituted or have a substituent. Examples of the substituent include the same substituents that Y 1 in the above formula (Ar-1) may have.
  • Ax has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle, and has 2 to 30 carbon atoms. Represents an organic group.
  • Ay is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon ring and aromatic. Represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of group heterocycles.
  • the aromatic ring in Ax and Ay may have a substituent, or Ax and Ay may be bonded to form a ring.
  • Q 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
  • Examples of Ax and Ay include those described in paragraphs [0039] to [0995] of Patent Document 2 (International Publication No. 2014/010325).
  • L 1 and L 2 independently represent an alkylene group represented by the following formula (I-2).
  • * represents the bonding position with Mes 1 or X 1 for L 1
  • m represents an integer of 3 to 20, preferably an integer of 3 to 15, and more preferably an integer of 3 to 10.
  • the hydrogen atom contained in the alkylene group represented by the above formula (I-2) is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, and the like. It may be substituted with a thioisocyano group or an alkyl group having 1 to 20 carbon atoms.
  • alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, a t-butyl group, an amyl group, and a 2-ethylhexyl group.
  • examples thereof include a nonyl group, a decanyl group, a lauryl group, a cetyl group, a stearyl group, and a cyclohexyl group.
  • one of -CH 2- which constitutes the alkylene group represented by the above formula (I-2) and is not directly bonded to X 1 or X 2 in the above formula (I-1).
  • two or more non-adjacent -CH 2- are -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O- It may be substituted with CO-O-, -CO-NH-, -NH-CO-, or -C ⁇ C-.
  • M is a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6.
  • the hydrogen atom contained in these groups is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or 1 to 20 carbon atoms. It may be substituted with an alkyl group of.
  • D 2 and D 3 are independently of -O-, -S-, -OCH 2- , -CH 2 CH 2- , -CO-, -COO-, respectively.
  • SP is a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkylene group having 1 to 12 carbon atoms.
  • -CH 2- constituting the above represents a divalent linking group substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-, where Q is , Represents a substituent.
  • the substituent include the same substituents that Y 1 in the above formula (Ar-1) may have.
  • examples of the linear or branched alkylene group having 1 to 12 carbon atoms 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. Is preferably mentioned.
  • P represents a polymerizable group.
  • a polymerizable group capable of radical polymerization or cationic polymerization is preferable.
  • a known radically polymerizable group can be used, and suitable examples thereof include an acryloyloxy group and a methacryloyloxy group. In this case, it is known that the acryloyloxy group is generally faster in terms of polymerization rate, and the acryloyloxy group is preferable from the viewpoint of improving productivity, but the methacryloyloxy group can also be used as the polymerizable group in the same manner.
  • a known cationically polymerizable group can be used, and specifically, an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiroorthoester group, and vinyloxy.
  • the group can be mentioned.
  • 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 preferable polymerizable groups include any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20). Of these, an acryloyloxy group or a methacryloyloxy group is more preferable. In the following formulas (P-1) to (P-20), * represents the bonding position with the SP.
  • n represents an integer of 2 or more, preferably an integer of 2 to 5, more preferably an integer of 2 to 4, and 2 or 3. Is more preferable.
  • the plurality of Ms may be the same or different, the plurality of D 2s may be the same or different, and the plurality of D 3s may be the same or different.
  • the plurality of SPs may be the same or different.
  • Specific examples of the specific compound include compounds represented by the following formulas (1) to (22), and specifically, K (specifically, K (1) to (22) in the following formulas (1) to (22).
  • Examples of the side chain structure) include compounds having the side chain structures shown in Tables 1 and 2 below. In Tables 1 and 2 below, "*" shown in the side chain structure of K represents the bonding position with the aromatic ring. Further, in the side chain structures represented by 1-9 in Table 1 below and 2-9 in Table 2 below, the groups adjacent to the acryloyloxy group and the methacryloyl group are propylene groups (methyl groups are ethylene groups, respectively). It represents a substituted group) and represents a mixture of positional isomers with different methyl group positions.
  • the content of the specific compound is set with respect to the total mass of the reverse wavelength dispersible liquid crystal compound and the specific compound, which will be described later, for the reason that the inverse wavelength dispersibility is easily exhibited in the formed optically anisotropic film. It is preferably 3 to 30% by mass, more preferably 5 to 20% by mass.
  • the reverse wavelength dispersible liquid crystal compound contained in the polymerizable liquid crystal composition of the present invention is not particularly limited as long as it is a polymerizable liquid crystal compound exhibiting reverse wavelength dispersibility.
  • the "polymerizable liquid crystal compound exhibiting inverse wavelength dispersibility” is an in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced using the same. When the measurement is performed, the Re value becomes equal or higher as the measurement wavelength becomes larger.
  • the reverse wavelength dispersible liquid crystal compound is preferably a compound represented by the following formula (II) because it is more excellent in reverse wavelength dispersibility.
  • a1, a2, g1 and g2 independently represent 0 or 1, respectively. However, at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1. Further, in the above formula (II), q represents 1 or 2. Further, in the above formula (II), D 6 , D 7 , D 8 , D 9 , D 10 and D 11 are independently single-bonded or -CO-, -O-, -S-,-, respectively.
  • R 1 ⁇ R 5 independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
  • a plurality of D 7 may each be the same or different.
  • G 1 and G 2 each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms which may have a substituent, and are alicyclic.
  • One or more of -CH 2- constituting the hydrocarbon group may be substituted with -O-, -S- or -NH-.
  • a 3 and A 4 are each independently, an aromatic ring or more carbon atoms 6 may have a substituent, or may have a substituent carbon atoms Represents 6 or more cycloalkane rings.
  • SP 3 and SP 4 are independently a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear chain having 1 to 12 carbon atoms.
  • Q represents a substituent.
  • L 5 and L 6 each independently represent a monovalent organic group, and at least one of L 1 and L 2 represents a polymerizable group.
  • Ar 3 is an aromatic ring represented by the above formula (Ar-3)
  • at least one of L 5 and L 6 and L 3 and L 4 in the above formula (Ar-3) are polymerized. Represents a sex group.
  • a1, a2, g1 and g2 are all preferably 1. Further, in the above formula (II), q is preferably 1.
  • the divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms represented by G 1 and G 2 is preferably a 5-membered ring or a 6-membered ring.
  • the alicyclic hydrocarbon group may be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferable.
  • the divalent alicyclic hydrocarbon group represented by G 1 and G 2 for example, the description in paragraph [0078] of JP2012-21068A can be referred to, and this content is incorporated in the present specification. ..
  • the A 3 and A 4 6 or more aromatic ring carbons indicated for example, a benzene ring, a naphthalene ring, an anthracene ring, an aromatic hydrocarbon ring such as phenanthroline ring; a furan ring, Aromatic heterocycles such as pyrrole ring, thiophene ring, pyridine ring, thiazole ring and benzothiazole ring; can be mentioned.
  • a benzene ring for example, a 1,4-phenyl group
  • a 1,4-phenyl group is preferable.
  • the cycloalkane ring having 6 or more carbon atoms A 3 and A 4 are shown, for example, cyclohexane ring, Shikuropeputan ring, cyclooctane ring, cyclododecane ring, etc. Shikurodokosan ring.
  • a cyclohexane ring for example, a 1,4-cyclohexylene group
  • a trans-1,4-cyclohexylene group is more preferable.
  • Y 1 in the above formula (Ar-1) is a substituent that may be contained in an aromatic ring having 6 or more carbon atoms or a cycloalkane ring having 6 or more carbon atoms. Examples thereof include the same substituents that may be possessed.
  • Examples of the monovalent organic group represented by L 5 and L 6 in the above formula (II) include an alkyl group, an aryl group, and a heteroaryl group.
  • the alkyl group may be linear, branched or cyclic, but linear is preferred.
  • the number of carbon atoms of 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 monocyclic is preferable.
  • the aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 10 carbon atoms.
  • the heteroaryl group may be monocyclic or polycyclic.
  • the number of heteroatoms constituting the heteroaryl group is preferably 1 to 3.
  • the hetero atom constituting the heteroaryl group is preferably a nitrogen atom, a sulfur atom, or an oxygen atom.
  • the heteroaryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms.
  • the alkyl group, the aryl group and the heteroaryl group may be unsubstituted or have a substituent. Examples of the substituent include the same substituents that Y 1 in the above-mentioned formula (Ar-1) may have.
  • Examples of the polymerizable group represented by at least one of L 5 and L 6 in the above formula (II) include those similar to those described in P in the above formula (I-3).
  • both L 5 and L 6 in the above formula (II) are polymerizable groups, and are acryloyloxy group or methacryloyloxy group. Is more preferable.
  • Ar 3 is represented by the following formulas (Ar-1) to (Ar-7), as in the preferred embodiment of Ar 1 and Ar 2 in the above formula (I-1). Represents any aromatic ring selected from the group consisting of groups. However, when q1 is 2, a plurality of Ar 3 may each be the same or different.
  • * represents the bonding position with D 5 or D 6 in the above formula (II).
  • Q 1, Q 2 and Y 1 for such each symbol Q 1, Q 2 and Y 1, as a preferred embodiment of Ar 1 and Ar 2 in the above formula (I-1) Similar to the one described.
  • inverse wavelength dispersible liquid crystal compound represented by the above formula (II) include compounds represented by the general formula (1) described in JP-A-2010-084032 (particularly, paragraph numbers). Compounds described in [0067] to [0073]), compounds represented by the general formula (II) described in JP-A-2016-053709 (particularly, compounds described in paragraph numbers [0036] to [0043]). , And the compound represented by the general formula (1) described in JP-A-2016-081035 (particularly, the compound described in paragraph numbers [0043] to [0055]) and the like.
  • a 3 and A 4 in the above formula (II) are independently cycloalkanes having 6 or more carbon atoms for the reason that the formed optically anisotropic film has better moist heat durability. It is preferably a polymerizable liquid crystal compound representing a ring, and A 3 and A 4 in the above formula (II) independently represent a cycloalkane ring having 6 or more carbon atoms, and in the above formula (II). It is more preferable that both D 7 and D 8 of the above are polymerizable liquid crystal compounds expressing a single bond.
  • Examples of such polymerizable liquid crystal compounds are preferably compounds represented by the following formulas (1) to (22), and specifically, K (specifically, K (1) to (22) in the following formulas (1) to (22)
  • Examples of the side chain structure) include compounds having the side chain structures shown in Tables 3 to 5 below.
  • "*" shown in the side chain structure of K represents the bonding position with the aromatic ring.
  • the groups adjacent to the acryloyloxy group and the methacryloyl group are propylene groups (methyl groups are ethylene groups, respectively). It represents a substituted group) and represents a mixture of positional isomers with different methyl group positions.
  • the polymerizable liquid crystal composition of the present invention may contain other polymerizable compounds having one or more polymerizable groups, in addition to the above-mentioned polymerizable liquid crystal compounds.
  • the polymerizable group of the other polymerizable compound is not particularly limited, and examples thereof include an acryloyl group, a methacryloyl group, a vinyl group, a styryl group, and an allyl group. Among them, it is preferable to have an acryloyl group and a methacryloyl group.
  • the other polymerizable compound is preferably another polymerizable compound having 1 to 4 polymerizable groups because the durability of the optically anisotropic film to be formed is improved, and the polymerizable group is used. More preferably, it is another polymerizable compound having two.
  • Examples of other polymerizable compounds include the compounds described in paragraphs [0073] to [0074] of JP-A-2016-053709.
  • Examples of other polymerizable compounds include compounds represented by the formulas (M1), (M2), and (M3) described in paragraphs [0030] to [0033] of JP-A-2014-0770668. More specifically, specific examples described in paragraphs [0046] to [0055] of the same publication can be mentioned.
  • those having the structures of the formulas (1) to (3) described in JP-A-2014-198814 can be preferably used, and more specifically, those having the structures of the same publication [0020 ] To [0035], [0042] to [0050], and [0056] to [0057].
  • the content is preferably less than 50% by mass, more preferably 40% by mass or less, based on the mass of the above-mentioned polymerizable liquid crystal compound. It is more preferably 2 to 30% by mass.
  • the polymerizable liquid crystal composition of the present invention preferably contains a polymerization initiator.
  • the polymerization initiator used is preferably a photopolymerization initiator capable of initiating a polymerization reaction by irradiation with ultraviolet rays.
  • Examples of the photopolymerization initiator include ⁇ -carbonyl compounds (described in US Pat. No. 2,376,661 and US Pat. No. 2,376,670), acidoin ethers (described in US Pat. No. 2,448,828), and ⁇ -hydrogen-substituted fragrances.
  • Group acidoine compounds described in US Pat. No. 2722512
  • polynuclear quinone compounds described in US Pat. Nos.
  • the polymerization initiator is preferably an oxime type polymerization initiator, and specific examples thereof are described in paragraphs [0049] to [0052] of International Publication No. 2017/170443. Agents are mentioned.
  • the polymerizable liquid crystal composition of the present invention preferably contains a solvent from the viewpoint of workability for forming an optically anisotropic film.
  • a solvent from the viewpoint of workability for forming an optically anisotropic film.
  • the solvent include a ketone solvent (for example, acetone, 2-butanone, methylisobutylketone, cyclohexanone, cyclopentanone, etc.), an ether solvent (for example, dioxane, tetrahydrofuran, etc.), and a cyclic amide solvent.
  • Solvents eg, N-methylpyrrolidone, N-ethylpyrrolidone, N, N'-dimethylimidazolidinone, etc.
  • aliphatic hydrocarbon solvents eg, hexane, etc.
  • alicyclic hydrocarbon solvents eg, cyclohexane
  • Aromatic hydrocarbon solvents eg toluene, xylene, trimethylbenzene, etc.
  • carbon halide solvents eg dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.
  • ester solvents eg methyl acetate, etc.
  • cellosolve solvents eg, methyl cellosolve, ethyl
  • At least one of the above-mentioned solvents selected from the group consisting of a ketone solvent, an ether solvent and a cyclic amide solvent for the reason that the effect of the present invention for suppressing an increase in filtration pressure becomes apparent. It is preferably a seed solvent.
  • the polymerizable liquid crystal composition of the present invention preferably contains a leveling agent from the viewpoint of keeping the surface of the optically anisotropic film smooth and facilitating orientation control.
  • a leveling agent is preferably a fluorine-based leveling agent or a silicon-based leveling agent because it has a high leveling effect on the amount of addition, and a fluorine-based leveling agent from the viewpoint of less likely to cause crying (bloom, bleed). Is more preferable.
  • Specific examples of the leveling agent include the compounds described in paragraphs [0079] to [0102] of JP-A-2007-069471, and the general formulas described in JP-A-2013-047204.
  • the polymerizable liquid crystal composition of the present invention may contain an orientation control agent, if necessary.
  • the orientation control agent can form various orientation states such as homeotropic orientation (vertical orientation), tilt orientation, hybrid orientation, and cholesteric orientation in addition to homogenius orientation, and can make a specific orientation state more uniform and more uniform. It can be realized by precise control.
  • a low-molecular-weight orientation control agent or a high-molecular-weight orientation control agent can be used as the orientation control agent that promotes homogenous orientation.
  • the low-molecular-weight orientation control agent include paragraphs [0009] to [0083] of JP-A-2002-20363, paragraphs [0111]-[0120] of JP-A-2006-106662, and JP-A-2012.
  • paragraphs [0021] to [0029] of Japanese Patent Application Laid-Open No. 211306 can be referred to, and this content is incorporated in the present specification.
  • orientation control agent for forming or promoting homeotropic orientation examples include boronic acid compounds and onium salt compounds. Specifically, paragraphs [0023] to [0032] of JP-A-2008-225281. , Paragraphs [0052] to [0058] of JP2012-208397A, paragraphs [0024] to [0055] of JP2008-026730, and [0043] to [0055] of JP2016-193869. The compounds described in paragraphs and the like can be taken into account, the contents of which are incorporated herein by reference.
  • the cholesteric orientation can be realized by adding a chiral agent to the polymerizable liquid crystal composition of the present invention, and the turning direction of the cholesteric orientation can be controlled by the direction of the chirality.
  • the pitch of cholesteric orientation can be controlled according to the orientation regulating force of the chiral agent.
  • the content is preferably 0.01 to 10% by mass and preferably 0.05 to 5% by mass with respect to the total solid content mass in the polymerizable liquid crystal composition. More preferred. When the content is in this range, it is possible to obtain a uniform and highly transparent optically anisotropic film without precipitation, phase separation, orientation defects, etc., while achieving the desired orientation state.
  • These orientation control agents can further impart a polymerizable functional group, particularly a polymerizable functional group that can be polymerized with the polymerizable liquid crystal compound constituting the polymerizable liquid crystal composition of the present invention.
  • the polymerizable liquid crystal composition of the present invention may contain a component other than the above-mentioned components, for example, a liquid crystal compound other than the above-mentioned polymerizable liquid crystal compound, a surfactant, a tilt angle control agent, an orientation aid, and a plasticizer. Agents, cross-linking agents and the like can be mentioned.
  • the compound of the present invention is a specific compound contained in the above-mentioned polymerizable liquid crystal composition of the present invention, and is a compound represented by the above-mentioned formula (I-1).
  • the optically anisotropic film of the present invention is an optically anisotropic film obtained by polymerizing the above-mentioned polymerizable liquid crystal composition of the present invention.
  • Examples of the method for forming the optically anisotropic film include a method of using the above-mentioned polymerizable liquid crystal composition of the present invention to achieve a desired orientation state and then immobilizing the film by polymerization.
  • the polymerization conditions are not particularly limited, but it is preferable to use ultraviolet rays in the polymerization by light irradiation.
  • the irradiation amount is preferably 10 mJ / cm 2 to 50 J / cm 2 , more preferably 20 mJ / cm 2 to 5 J / cm 2 , and even more preferably 30 mJ / cm 2 to 3 J / cm 2. , 50 to 1000 mJ / cm 2 is particularly preferable.
  • the optically anisotropic film can be formed on an arbitrary support in the optical film of the present invention described later or on a polarizer in the polarizing plate of the present invention described later.
  • the optically anisotropic film of the present invention preferably satisfies the following formula (III). 0.50 ⁇ Re (450) / Re (550) ⁇ 1.00 ... (III)
  • Re (450) represents the in-plane lettering of the optically anisotropic film at a wavelength of 450 nm
  • Re (550) represents the in-plane letter of the optically anisotropic film at a wavelength of 550 nm.
  • the optically anisotropic membrane of the present invention is preferably a positive A plate or a positive C plate, and more preferably a positive A plate.
  • the positive A plate (positive A plate) and the positive C plate (positive C plate) are defined as follows.
  • the refractive index in the slow axis direction in the film plane (the direction in which the refractive index in the plane is maximized) is nx
  • the refractive index in the direction orthogonal to the slow phase axis in the plane in the plane is ny
  • the refraction in the thickness direction is nz
  • the positive A plate satisfies the relation of the formula (A1)
  • the positive C plate satisfies the relation of the formula (C1).
  • the positive A plate shows a positive value for Rth
  • the positive C plate shows a negative value for Rth.
  • ⁇ includes not only the case where both are completely the same, but also the case where both are substantially the same. “Substantially the same” means that, for example, in the positive A plate, (ny-nz) ⁇ d (where d is the thickness of the film) is -10 to 10 nm, preferably -5 to 5 nm. It is included in “ny ⁇ nz”, and when (nx-nz) xd is -10 to 10 nm, preferably -5 to 5 nm, it is also included in "nx ⁇ nz”.
  • (nx ⁇ ny) ⁇ d (where d is the thickness of the film) is 0 to 10 nm, preferably 0 to 5 nm, it is also included in “nx ⁇ ny”.
  • Re (550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, from the viewpoint of functioning as a ⁇ / 4 plate. It is more preferably 130 to 150 nm, and particularly preferably 130 to 140 nm.
  • the " ⁇ / 4 plate” is a plate having a ⁇ / 4 function, and specifically, a function of converting linearly polarized light having a specific wavelength into circularly polarized light (or converting circularly polarized light into linearly polarized light). It is a plate having.
  • the optical film of the present invention is an optical film having the optically anisotropic film of the present invention.
  • 1A, 1B and 1C are schematic cross-sectional views showing an example of the optical film of the present invention, respectively.
  • FIG. 1 is a schematic view, and the thickness relationship and positional relationship of each layer do not always match the actual ones, and the support, alignment film, and hard coat layer shown in FIG. 1 all have an arbitrary configuration. It is a member.
  • the optical film 10 shown in FIG. 1 has a support 16, an alignment film 14, and an optically anisotropic film 12 in this order. Further, as shown in FIG.
  • the optical film 10 may have a hard coat layer 18 on the side opposite to the side where the alignment film 14 of the support 16 is provided, and as shown in FIG. 1C, the optical film 10 may have a hard coat layer 18.
  • the hard coat layer 18 may be provided on the side of the optically anisotropic film 12 opposite to the side on which the alignment film 14 is provided.
  • optically anisotropic film of the optical film of the present invention is the above-mentioned optically anisotropic film of the present invention.
  • the thickness of the optically anisotropic film is not particularly limited, but is preferably 0.1 to 10 ⁇ m, more preferably 0.5 to 5 ⁇ m.
  • the optical film of the present invention may have a support as a base material for forming an optically anisotropic film.
  • a support is preferably transparent, and specifically, the light transmittance is preferably 80% or more.
  • Examples of such a support include a glass substrate and a polymer film, and examples of the polymer film material include a cellulose-based polymer; an acrylic-based polymer having an acrylic acid ester polymer such as polymethylmethacrylate and a lactone ring-containing polymer.
  • the thickness of the support is not particularly limited, but is preferably 5 to 60 ⁇ m, more preferably 5 to 30 ⁇ m.
  • the optical film of the present invention has any of the above-mentioned supports, it is preferable that the optical film has an alignment film between the support and the optically anisotropic film.
  • the support described above may also serve as an alignment film.
  • the alignment film generally contains a polymer as a main component.
  • the polymer material for an alignment film has been described in a large number of documents, and a large number of commercially available products are available.
  • the polymer material used in the present invention is preferably polyvinyl alcohol or polyimide, or a derivative thereof. Particularly modified or unmodified polyvinyl alcohol is preferable.
  • the alignment film for example, the alignment film described in International Publication No. 01/88574, p. 43, p. 24 to p. 49, p. 8; ], And the like; a liquid crystal alignment film formed by the liquid crystal alignment agent described in Japanese Patent Application Laid-Open No. 2012-155308; and the like.
  • a photoalignment film as the alignment film because it is possible to prevent surface deterioration by not contacting the surface of the alignment film when forming the alignment film.
  • the photoalignment film is not particularly limited, but is a polymer material such as a polyamide compound or a polyimide compound described in paragraphs [0024] to [0043] of International Publication No. 2005/096041; A liquid crystal alignment film formed by a liquid crystal alignment agent having a photo-oriented group; a trade name LPP-JP265CP manufactured by Polyimide, Inc. can be used.
  • the thickness of the alignment film is not particularly limited, but from the viewpoint of alleviating the surface irregularities that may exist on the support and forming an optically anisotropic film having a uniform film thickness, 0. It is preferably 01 to 10 ⁇ m, more preferably 0.01 to 1 ⁇ m, and even more preferably 0.01 to 0.5 ⁇ m.
  • the optical film of the present invention preferably has a hard coat layer in order to impart the physical strength of the film.
  • the hard coat layer may be provided on the side opposite to the side where the alignment film of the support is provided (see FIG. 1B), and the side where the alignment film of the optically anisotropic film is provided. May have a hard coat layer on the opposite side (see FIG. 1C).
  • the hard coat layer those described in paragraphs [0190] to [0196] of JP2009-98658A can be used.
  • the optical film of the present invention may have another optically anisotropic film in addition to the optically anisotropic film of the present invention. That is, the optical film of the present invention may have a laminated structure of the optically anisotropic film of the present invention and another optically anisotropic film.
  • Such other optically anisotropic films are optically anisotropic obtained by using the above-mentioned inverse wavelength dispersible liquid crystal compound or other polymerizable compound (particularly, liquid crystal compound) without blending the above-mentioned specific compound. If it is a film, it is not particularly limited.
  • liquid crystal compounds can be classified into rod-shaped type and disk-shaped type according to their shapes.
  • a polymer generally refers to a polymer having a degree of polymerization of 100 or more (Polymer Physics / Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992).
  • any liquid crystal compound can be used, but it is preferable to use a rod-shaped liquid crystal compound or a discotic liquid crystal compound (disk-shaped liquid crystal compound).
  • a rod-shaped liquid crystal compound or a discotic liquid crystal compound disk-shaped liquid crystal compound.
  • Two or more kinds of rod-shaped liquid crystal compounds, two or more kinds of disk-shaped liquid crystal compounds, or a mixture of a rod-shaped liquid crystal compound and a disk-shaped liquid crystal compound may be used.
  • the liquid crystal compound may have two or more polymerizable groups in one molecule. More preferred.
  • the liquid crystal compound is a mixture of two or more kinds, it is preferable that at least one kind of liquid crystal compound has two or more polymerizable groups in one molecule.
  • the rod-shaped liquid crystal compound for example, those described in claim 1 of JP-A-11-513019 and paragraphs [0026] to [0098] of JP-A-2005-289980 can be preferably used, and discotics can be used.
  • liquid crystal compound for example, those described in paragraphs [0020] to [0067] of JP2007-108732 and paragraphs [0013] to [0108] of JP2010-244038 can be preferably used. However, it is not limited to these.
  • the optical film of the present invention preferably contains an ultraviolet (UV) absorber in consideration of the influence of external light (particularly ultraviolet rays).
  • the ultraviolet absorber may be contained in the optically anisotropic film of the present invention, or may be contained in a member other than the optically anisotropic film constituting the optical film of the present invention.
  • a support is preferably mentioned.
  • the ultraviolet absorber any conventionally known one capable of exhibiting ultraviolet absorption can be used.
  • a benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorber may be used from the viewpoint of obtaining the ultraviolet absorbing ability (ultraviolet blocking ability) used in an image display device because of its high ultraviolet absorbing ability. preferable.
  • two or more kinds of ultraviolet absorbers having different maximum absorption wavelengths can be used in combination.
  • Specific examples of the ultraviolet absorber include compounds described in paragraphs [0258] to [0259] of JP2012-18395, paragraphs [0055] to [0105] of JP2007-72163. Examples thereof include the compounds described in.
  • Tinuvin400, Tinuvin405, Tinuvin460, Tinuvin477, Tinuvin479, Tinuvin1577 (all manufactured by BASF) and the like can be used.
  • the polarizing plate of the present invention has the above-mentioned optical film of the present invention and a polarizer. Further, the polarizing plate of the present invention can be used as a circular polarizing plate when the above-mentioned optically anisotropic film of the present invention is a ⁇ / 4 plate (positive A plate). Further, when the optically anisotropic film of the present invention described above is a ⁇ / 4 plate (positive A plate), the polarizing plate of the present invention has a slow phase axis of the ⁇ / 4 plate and an absorption axis of a polarizer described later.
  • the angle formed by the light is preferably 30 to 60 °, more preferably 40 to 50 °, further preferably 42 to 48 °, and particularly preferably 45 °.
  • the "slow phase axis" of the ⁇ / 4 plate means the direction in which the refractive index becomes maximum in the plane of the ⁇ / 4 plate
  • the "absorption axis" of the polarizer means the direction in which the absorbance is highest. To do.
  • the polarizer of the polarizing plate of the present invention is not particularly limited as long as it is a member having a function of converting light into specific linearly polarized light, and conventionally known absorption type polarizers and reflection type polarizers can be used. ..
  • absorption type polarizer an iodine-based polarizer, a dye-based polarizer using a dichroic dye, a polyene-based polarizer, and the like are used. Iodine-based polarized light and dye-based polarized light include coated and stretched polarized light, and both can be applied.
  • the reflective polarizer a polarizer in which thin films having different birefringences are laminated, a wire grid type polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection region and a 1/4 wave plate are combined, and the like are used.
  • polyvinyl alcohol-based resin polymer containing as a repeating unit -CH 2 -CHOH-, in particular, polyvinyl alcohol and ethylene - at least one selected from the group consisting of vinyl alcohol copolymer It is preferable that the polymer contains one).
  • the thickness of the polarizer is not particularly limited, but is preferably 3 ⁇ m to 60 ⁇ m, more preferably 5 ⁇ m to 30 ⁇ m, and even more preferably 5 ⁇ m to 15 ⁇ m.
  • an adhesive layer may be arranged between the optically anisotropic film in the optical film of the present invention and the polarizer.
  • G "/ G') represents a substance having a value of 0.001 to 1.5, and includes so-called adhesives, substances that easily creep, and the like.
  • Examples of the pressure-sensitive adhesive that can be used in the present invention include, but are not limited to, a polyvinyl alcohol-based pressure-sensitive adhesive.
  • 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 of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as “EL”) display panel, and a plasma display panel.
  • EL organic electroluminescence
  • a liquid crystal cell and an organic EL display panel are preferable, and a liquid crystal cell is more preferable.
  • the image display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as a display element and an organic EL display device using an organic EL display panel as a display element, and the liquid crystal display device is preferable. More preferred.
  • the liquid crystal display device which is an example of the image display device of the present invention is a liquid crystal display device having the above-mentioned polarizing plate of the present invention and a liquid crystal cell.
  • the polarizing plate of the present invention among the polarizing plates provided on both sides of the liquid crystal cell, it is preferable to use the polarizing plate of the present invention as the polarizing plate on the front side, and the polarizing plate of the present invention as the polarizing plate on the front side and the rear side. Is more preferable to use.
  • the liquid crystal cells constituting the liquid crystal display device will be described in detail below.
  • the liquid crystal cell used in the liquid crystal display device is a VA (Vertical Element) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, an FFS (Fringe-Field-Switching) mode, or a TN (Twisted) mode.
  • VA Vertical Element
  • OCB Optically Compensated Bend
  • IPS In-Plane-Switching
  • FFS Feringe-Field-Switching
  • TN Transmission-Field-Switching
  • the Nematic mode is preferred, but is not limited to these.
  • the rod-shaped liquid crystal molecules are substantially horizontally oriented when no voltage is applied, and are further twisted to 60 to 120 °.
  • the TN mode liquid crystal cell is most often used as a color TFT liquid crystal display device, and has been described in many documents.
  • the rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied.
  • a VA mode liquid crystal cell in a narrow sense in which rod-shaped liquid crystal molecules are oriented substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied Japanese Patent Laid-Open No. 2-.
  • Liquid crystal cells in a mode in which rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied and twisted and multi-domain oriented when a voltage is applied. (1998)) and (4) SURVIVAL mode liquid crystal cells (announced at LCD International 98) are included. Further, it may be any of PVA (Patternized Vertical Alignment) type, optical alignment type (Optical Alignment), and PSA (Polymer-Sustained Alignment). Details of these modes are described in Japanese Patent Application Laid-Open No. 2006-215326 and Japanese Patent Application Laid-Open No. 2008-538819.
  • the rod-shaped liquid crystal molecules are oriented substantially parallel to the substrate, and the liquid crystal molecules respond in a plane by applying an electric field parallel to the substrate surface.
  • the display is black when no electric field is applied, and the absorption axes of the pair of upper and lower polarizing plates are orthogonal to each other.
  • Methods for reducing leakage light when displaying black in an oblique direction and improving the viewing angle by using an optical compensation sheet are described in JP-A-10-54982, JP-A-11-202323, and JP-A-9-292522. It is disclosed in JP-A-11-133408, JP-A-11-305217, JP-A-10-307291, and the like.
  • Organic EL display device examples include, from the visual side, a polarizer, a ⁇ / 4 plate (positive A plate) made of the optically anisotropic film of the present invention, and an organic EL.
  • a mode in which the display panel and the display panel are provided in this order is preferably mentioned.
  • the organic EL display panel is a display panel configured by using an organic EL element formed by sandwiching an organic light emitting layer (organic electroluminescence layer) between electrodes (between a cathode and an anode).
  • the configuration of the organic EL display panel is not particularly limited, and a known configuration is adopted.
  • a reverse wavelength dispersive liquid crystal compound (II-a) represented by the following formula (II-a) was synthesized according to the method described in paragraph [0122] (Example 4) of JP-A-2016-081035.
  • the group adjacent to the acryloyloxy group represents a propylene group (a group in which a methyl group is replaced with an ethylene group), and represents a mixture of positional isomers having different methyl group positions.
  • a reverse wavelength dispersible liquid crystal compound (II-c) represented by the following formula (II-c) was synthesized according to the methods described in paragraphs [0252] to [0257] of JP-A-2011-162678.
  • Example 1 Manufacturing of optical film
  • a polymerizable liquid crystal composition having the following composition was prepared and applied to a glass substrate with a rubbing-treated polyimide alignment film (SE-150 manufactured by Nissan Chemical Industries, Ltd.) by spin coating.
  • the coating film was oriented at the temperatures shown in Table 6 below to form a liquid crystal layer.
  • the film was cooled to the exposure temperature shown in Table 6 below , and the orientation was fixed by irradiation with ultraviolet rays of 1000 mJ / cm 2 , to form an optically anisotropic film, and an optical film was prepared.
  • Example 2 to 4 An optical film was produced in the same manner as in Example 1 except that the inverse wavelength dispersible liquid crystal compound or the specific compound was changed to the compound shown in Table 6 below.
  • ⁇ Light resistance> For the produced optical film, set the glass substrate on a xenon irradiator (SX75 manufactured by Suga Test Instruments Co., Ltd.) so that the coating film of the polymerizable liquid crystal composition serves as the irradiation surface, and use a # 275 filter for 200 hours. An irradiation test was conducted. The Re (550) of the optical film before the test and the Re (550) of the optical film after the test were measured, and the light resistance was evaluated according to the following criteria. The results are shown in Table 6 below. A: The amount of change in Re (550) after the test with respect to Re (550) before the test is less than 5% of Re (550) before the test.
  • Re (550) after the test with respect to Re (550) before the test The amount of change is 5% or more and less than 15% of Re (550) before the test
  • C The amount of change of Re (550) after the test with respect to Re (550) before the test is 15% or more of Re (550) before the test.

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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)
PCT/JP2020/036159 2019-09-27 2020-09-25 重合性液晶組成物、化合物、光学異方性膜、光学フィルム、偏光板および画像表示装置 Ceased WO2021060428A1 (ja)

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