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WO2020054459A1 - Composition de cristaux liquides polymérisable, couche optiquement anisotrope, plaque de polarisation, dispositif d'affichage à cristaux liquides et dispositif électroluminescent organique - Google Patents

Composition de cristaux liquides polymérisable, couche optiquement anisotrope, plaque de polarisation, dispositif d'affichage à cristaux liquides et dispositif électroluminescent organique Download PDF

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WO2020054459A1
WO2020054459A1 PCT/JP2019/034088 JP2019034088W WO2020054459A1 WO 2020054459 A1 WO2020054459 A1 WO 2020054459A1 JP 2019034088 W JP2019034088 W JP 2019034088W WO 2020054459 A1 WO2020054459 A1 WO 2020054459A1
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liquid crystal
carbon atoms
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plate
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慶介 吉政
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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
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • 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
    • 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
    • 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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/8791—Arrangements for improving contrast, e.g. preventing reflection of ambient light

Definitions

  • the present invention relates to a polymerizable liquid crystal composition, an optically anisotropic layer, a polarizing plate, a liquid crystal display device, and an organic electroluminescent device.
  • a polarizing plate having an optically anisotropic layer and a polarizer has been used for a liquid crystal display device, an organic electroluminescent device, and the like for the purpose of optical compensation and antireflection.
  • a polarizer (so-called broadband polarizer) has been developed which can provide similar effects to white light, which is a composite wave in which light rays in the visible light range are mixed, corresponding to light rays of all wavelengths.
  • the thickness of the optically anisotropic layer included in the polarizing plate is also required to be reduced.
  • Patent Documents 1 and 2 propose the use of a polymerizable liquid crystal compound having reverse wavelength dispersion as a polymerizable compound used for forming an optically anisotropic layer.
  • the present inventor studied a polarizing plate having an optically anisotropic layer obtained by polymerizing a polymerizable liquid crystal composition containing a compound (polymerizable liquid crystal compound) described in Patent Documents 1 and 2,
  • a practical mode for example, a circularly polarizing plate for preventing reflection of an organic electroluminescent smartphone
  • reddish unevenness occurs in the center of the plane.
  • the reverse wavelength dispersive polymerizable liquid crystal compound is inferior in durability in a high-temperature and high-humidity environment, but as described above, an environment sandwiched by glass, that is, a dry environment in which moisture is not supplied.
  • an environment sandwiched by glass that is, a dry environment in which moisture is not supplied.
  • the occurrence of redness unevenness under high temperature conditions in the above is an unexpected problem.
  • an object of the present invention is to provide a polymerizable liquid crystal composition, an optically anisotropic layer, a polarizing plate, a liquid crystal display device, and an organic electroluminescent device that can produce a polarizing plate having excellent heat durability.
  • the present inventors have conducted intensive studies on the above problems, and as a result, by using a polymerizable liquid crystal composition containing a compound having an oxetane structure together with a specific polymerizable liquid crystal compound, a polarizing plate excellent in heat durability can be produced. And found the present invention. That is, the present inventor has found that the above problem can be solved by the following configuration.
  • the polymerizable liquid crystal composition according to [1], wherein the compound having an oxetane structure has a molecular weight of 300 or less.
  • a polarizing plate comprising the optically anisotropic layer according to any one of [5] to [10] and a polarizer.
  • a liquid crystal display device having the polarizing plate according to [11].
  • An organic electroluminescent device comprising the polarizing plate according to [11].
  • a polymerizable liquid crystal composition an optically anisotropic layer, a polarizing plate, a liquid crystal display device, and an organic electroluminescent device capable of producing a polarizing plate having excellent heat durability.
  • each component may use a substance corresponding to each component alone or in combination of two or more.
  • the content of that component refers to the total content of the substances used in combination unless otherwise specified.
  • the bonding direction of a divalent group is not particularly limited except for a case where a bonding position is specified, and for example, a compound represented by the following formula ( In the case where D 1 in II) is —CO—O—, when the position bonding to the G 1 side is * 1 and the position bonding to the Ar side is * 2, D 1 is * 1- It may be CO-O- * 2 or * 1-O-CO- * 2.
  • (meth) acrylate is a notation representing “acrylate” or “methacrylate”
  • “(meth) acryl” is a notation representing “acryl” or “methacryl”
  • “(Meth) acryloyl” is a notation representing “acryloyl” or “methacryloyl”.
  • “orthogonal” and “parallel” with respect to an angle mean a range of an exact angle ⁇ 10 °, and “identical” and “different” with respect to an angle have a difference of less than 5 ° Can be determined based on whether or not.
  • “visible light” means 380 to 780 nm. In this specification, the measurement wavelength is 550 nm unless otherwise specified.
  • water content means the initial weight of the cut sample and the weight obtained by converting the change in dry weight after drying at 120 ° C. for 2 hours into a unit area.
  • slow axis means a direction in which the refractive index becomes maximum in a plane.
  • the slow axis of the optically anisotropic layer means the slow axis of the entire optically anisotropic layer.
  • Re ( ⁇ ) and Rth ( ⁇ ) represent an in-plane retardation and a retardation in a thickness direction at a wavelength ⁇ , respectively.
  • the values of the in-plane retardation and the retardation in the thickness direction refer to values measured using AxoScan OPMF-1 (manufactured by Optoscience) using light of a measurement wavelength.
  • the polymerizable liquid crystal composition of the present invention includes a compound having an oxetane structure (hereinafter, also simply referred to as “oxetane compound”) and a polymerizable liquid crystal compound represented by the following formula (II) (hereinafter, simply referred to as “specific liquid crystal compound”). "Is also abbreviated.). L 1 -G 1 -D 1- (Ar-D 2 ) p -G 2 -L 2 (II)
  • the present inventors speculate as follows.
  • the polymerizable liquid crystal compound is easily susceptible to decomposition by water, and this problem tends to be significant when a polymerizable liquid crystal compound having reverse wavelength dispersion is used among the polymerizable liquid crystal compounds.
  • the present inventor has found that when an optically anisotropic layer manufactured using a specific liquid crystal compound is exposed to a high-temperature and high-humidity condition, the specific anisotropic layer contained in the optically anisotropic layer is passed through a certain induction period. It has been found that the decomposition of the liquid crystal compound occurs rapidly and the in-plane retardation value fluctuates greatly. This reason is presumed to be due to the following phenomenon.
  • the specific liquid crystal compound reverse wavelength dispersive
  • the specific liquid crystal compound has an electron-withdrawing property, which increases the positive polarization of carbon atoms constituting the specific liquid crystal compound.
  • it becomes susceptible to attack by nucleophiles (estimated as water).
  • the present inventor questioned whether or not the cause of the generation of redness unevenness under high-temperature conditions in a dry environment is really a hydrolysis reaction in which the nucleophilic species is water as described above. Therefore, the present inventor further studied and found that the supply source of water was a trace amount of water contained in the polarizing plate (mainly, polyvinyl alcohol of the polarizer). In other words, at the end of the polarizing plate, the amount of water supplied to the optically anisotropic layer also decreases due to the consumption and diffusion of the water in the supply source in the in-plane direction before the hydrolysis reaction occurs.
  • the polarizing plate mainly, polyvinyl alcohol of the polarizer
  • the hydrolysis reaction occurs earlier than the water in the supply source diffuses in the in-plane direction and is consumed, and the in-plane retardation value fluctuates. It is estimated that it has brought. Therefore, in the present invention, it is considered that the hydrolysis reaction was suppressed by the reaction of the oxetane compound with water, and an improvement effect was obtained.
  • the oxetane compound does not have a reaction rate with water that is not too fast or too slow, and has an appropriate reaction rate. Can be inferred.
  • each component of the polymerizable liquid crystal composition of the present invention will be described in detail.
  • the polymerizable liquid crystal composition of the present invention contains an oxetane compound.
  • the oxetane compound is not particularly limited as long as it has an oxetane structure in the molecule.
  • those containing a plurality of oxetane rings in the molecule include 1,4-bis [(3-ethyl-3-oxetanyl) methoxymethyl] benzene and di [(3-ethyl-3-oxetanyl) methyl] Ether and xylylenebisoxetane. These may be used alone or in combination of two or more.
  • oxetane compounds can be easily obtained as commercial products, and as the commercially available products, "Aron Oxetane (registered trademark) @ OXT-121” is a product name sold by Toagosei Co., Ltd. "," Alonoxetane (registered trademark) @ OXT-211 ",” Alonoxetane (registered trademark) @ OXT-221 ",” Alonoxetane (registered trademark) @ OXT-212 "and the like.
  • the above oxetane compound is, from the viewpoint of the oxetane structure remaining even by radical polymerization of the specific liquid crystal compound, It is preferably a non-liquid crystalline compound.
  • the oxetane compound is preferably a compound having a plurality of oxetane structures (oxetane rings) in the molecule, because the hydrolysis reaction is further suppressed and the improvement effect becomes larger.
  • the molecular weight of the oxetane compound is preferably 300 or less from the viewpoint of maintaining the orientation of the specific liquid crystal compound described later.
  • the content of the oxetane compound is determined based on the viewpoint of the orientation of the specific liquid crystal compound described below and the reason that the heat durability of the polarizing plate having the optically anisotropic layer to be formed is further improved.
  • the amount is preferably from 0.5 to 10 parts by mass, more preferably from 0.8 to 8.0 parts by mass, even more preferably from 1.0 to 6.0 parts by mass with respect to parts by mass. .
  • the specific liquid crystal compound contained in the polymerizable liquid crystal composition of the present invention is a polymerizable liquid crystal compound represented by the following formula (II), and is a compound having “reverse wavelength dispersion”.
  • a compound exhibiting “reverse wavelength dispersibility” refers to an in-plane retardation (Re) value at a specific wavelength (visible light range) of an optically anisotropic layer manufactured using the compound.
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
  • R 1 , R 2 , R 3 and R 4 When a plurality of each of R 1 , R 2 , R 3 and R 4 are present, a plurality of R 1 , a plurality of R 2 , a plurality of R 3 and a plurality of R 4 may be the same or different from each other. Good.
  • G 1 and G 2 each independently represent a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms which may have a substituent, or an aromatic hydrocarbon which may have a substituent; Represents a hydrogen group, and one or more of —CH 2 — constituting the alicyclic hydrocarbon group may be substituted with —O—, —S—, or —NH—.
  • L 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 and L 2 represents a monovalent group having a polymerizable group.
  • Ar is a divalent aromatic represented by the following formula (II-1), (II-2), (II-3), (II-4), (II-5) or (II-6) Represents a ring group.
  • Ar preferably represents a divalent aromatic ring group represented by the following formula (II-1), (II-2), (II-3) or (II-4). More preferably, it represents a divalent aromatic ring group represented by (II-1) or (II-2).
  • p represents 1 or 2, and when p is 2, a plurality of Ar may be the same or different, and a plurality of D 2 may be the same or different, respectively. . Note that p is preferably 1.
  • * represents the bonding position to D 1 or D 2.
  • Q 1 represents N or CH, and preferably represents N.
  • Q 2 is, -S -, - O-, or -NR 11 - represents a.
  • R 11 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent.
  • Z 1 , Z 2 and Z 3 each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and a monovalent carbon atom having 6 to 20 carbon atoms.
  • Z 1 and Z 2 may combine with each other to form an aromatic ring or an aromatic heterocyclic ring, and R 12 and R 13 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, and is preferably an aromatic hydrocarbon ring group; Heterocyclic group; an alkyl group having 3 to 20 carbon atoms having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle; a group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle An alkenyl group having 3 to 20 carbon atoms having at least one aromatic ring selected from the group consisting of: an alkenyl group having 3 to 20 carbon atoms having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
  • An alkenyl group; Ay is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or a carbon atom having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
  • the aromatic rings in Ax and Ay may each have a substituent, and Ax and Ay may combine 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.
  • substituents examples include a halogen atom, an alkyl group, a halogenated alkyl group, an alkenyl group, an aryl group, a cyano group, an amino group, a nitro group, a nitroso group, a carboxy group, an alkylsulfinyl group having 1 to 6 carbon atoms, An alkylsulfonyl group having 1 to 6 carbon atoms, a fluoroalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylsulfanyl group having 1 to 6 carbon atoms, an N-alkylamino group having 1 to 6 carbon atoms, An N, N-dialkylamino group having 2 to 12 carbon atoms, an N-alkylsulfamoyl group having 1 to 6 carbon atoms, an N, N-dialkylsulfamoyl group having 2 to 12 carbon atoms, or a
  • D 1 , D 2 , G 1 , and G relating to the compound (A) described in JP-A-2012-21068 are described.
  • 2 , L 1 , L 2 , R 4 , R 5 , R 6 , R 7 , X 1 , Y 1 , Q 1 , Q 2 are described as D 1 , D 2 , G 1 , G 2 , L 1 , respectively.
  • L 2 , R 1 , R 2 , R 3 , R 4 , Q 1 , Y 1 , Z 1 , and Z 2 can be referred to and represented by the general formula (I) described in JP-A-2008-107767.
  • a 1 for compound, a 2, and the description of X respectively a 1, a 2, and can refer to the X
  • Z 3 can refer to the description for Q 1 relates to compounds (A) described in JP-A-2012-21068.
  • the organic groups represented by L 1 and L 2 are each particularly preferably a group represented by —D 3 —G 3 —Sp—P 3 .
  • D 3 has the same meaning as D 1 .
  • G 3 represents a single bond, a divalent aromatic or heterocyclic group having 6 to 12 carbon atoms, or a divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms, and the above alicyclic hydrocarbon group May be substituted with —O—, —S— or —NR 7 —, wherein R 7 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • n represents an integer of 2 to 12
  • m represents an integer of 2 to 6
  • R 8 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • the hydrogen atom of —CH 2 — in each of the above groups may be substituted with a methyl group.
  • P 3 represents a polymerizable group.
  • the polymerizable group is not particularly limited, but a polymerizable group capable of radical polymerization or cationic polymerization is preferable.
  • examples of the radical polymerizable group include known radical polymerizable groups, and an acryloyl group or a methacryloyl group is preferable. It is known that an acryloyl group generally has a high polymerization rate, and an acryloyl group is preferable from the viewpoint of improving productivity. However, a methacryloyl group can be similarly used as a polymerizable group of a highly birefringent liquid crystal.
  • Examples of the cationic polymerizable group include known cationic polymerizable groups, and examples thereof include an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiro ortho ester group, and a vinyloxy group. Among them, an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is more preferable. Examples of particularly preferred polymerizable groups include the following.
  • alkyl group may be any of linear, branched and cyclic, and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl Group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, 1,1-dimethylpropyl group, n-hexyl group, isohexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, and And a cyclohexyl group.
  • the group adjacent to the acryloyloxy group in the above formulas II-2-8 and II-2-9 represents a propylene group (a group in which a methyl group is replaced by an ethylene group), and the methyl group is located at different positions. Represents a mixture of bodies.
  • K side chain structure
  • K includes a compound having a side chain structure shown in Tables 1 and 2 below.
  • “*” shown in the side chain structure of K indicates a bonding position with an aromatic ring.
  • a group adjacent to an acryloyloxy group and a methacryloyl group is a propylene group (a methyl group is an ethylene group). Substituted group), and represents a mixture of positional isomers having different methyl groups.
  • the content of the specific liquid crystal compound is not particularly limited, but is preferably from 50 to 100% by mass, more preferably from 70 to 99% by mass, based on the total solid content in the composition.
  • the solid content means other components except for the solvent in the composition, and is calculated as a solid content even if its properties are liquid.
  • the polymerizable liquid crystal composition of the present invention may contain a polymerizable rod-shaped compound in addition to the above-described specific liquid crystal compound from the viewpoint of controlling the liquid crystal alignment.
  • the polymerizable rod-like compound may or may not have liquid crystallinity.
  • the above polymerizable rod-shaped compound is a compound partially having a cyclohexane ring in which one hydrogen atom is substituted with a linear alkyl group (hereinafter, referred to as “alkylcyclohexane ring”).
  • cyclohexane ring in which one hydrogen atom is substituted with a linear alkyl group means, for example, as shown in the following formula (2), when two cyclohexane rings are present, Refers to a cyclohexane ring in which one hydrogen atom of the cyclohexane ring present is substituted with one linear alkyl group.
  • alkylcyclohexane ring-containing compound examples include compounds having a structure represented by the following formula (2). Among them, from the viewpoint of imparting wet heat resistance of the optically anisotropic layer, a (meth) acryloyl group is preferably used. It is preferably a compound represented by the following formula (3).
  • * represents a bonding position.
  • R 2 represents an alkyl group having 1 to 10 carbon atoms
  • n represents 1 or 2
  • W 1 and W 2 represent an alkyl group, an alkoxy group or a halogen atom, respectively.
  • W 1 and W 2 may be bonded to each other to form a ring structure which may have a substituent.
  • Z represents —COC— or —OCO—
  • L represents an alkylene group having 1 to 6 carbon atoms
  • R 3 represents a hydrogen atom or a methyl group.
  • alkylcyclohexane ring-containing compound examples include compounds represented by the following formulas A-1 to A-5.
  • R 4 represents an ethyl group or a butyl group.
  • the content of the polymerizable rod-shaped compound is preferably 1 to 30% by mass based on the total mass of the above-mentioned specific liquid crystal compound and the polymerizable rod-shaped compound. More preferably, it is 2020% by mass.
  • the polymerizable liquid crystal composition of the present invention may contain a polymerizable liquid crystal compound other than the specific liquid crystal compound and the polymerizable rod compound described above (hereinafter, also abbreviated as “other polymerizable liquid crystal compound”).
  • the polymerizable group of the other polymerizable liquid crystal compound is not particularly limited, and examples thereof include a (meth) acryloyl group, a vinyl group, a styryl group, and an allyl group. Especially, it is preferable to have a (meth) acryloyl group.
  • the other polymerizable liquid crystal compound is preferably a polymerizable compound having 2 to 4 polymerizable groups, for example, because the durability of the optically anisotropic layer is improved. More preferably, it is a polymerizable compound having two.
  • Such other polymerizable liquid crystal compounds are represented by, for example, formulas (M1), (M2), and (M3) described in paragraphs [0030] to [0033] of JP-A-2014-077068. And specific examples described in paragraphs [0046] to [0055] of the publication.
  • the other polymerizable liquid crystal compounds may be used alone or in combination of two or more.
  • the content of the other polymerizable liquid crystal compound is from 1 to 40 mass% based on the total mass of the above-described specific liquid crystal compound, polymerizable rod-shaped compound and other polymerizable liquid crystal compound. %, More preferably 1 to 10% by mass.
  • the polymerizable liquid crystal composition of the present invention preferably contains a non-liquid crystalline polyfunctional polymerizable compound because the heat durability of the polarizing plate having the optically anisotropic layer formed is further improved. . This is because the increase in the crosslinking point density suppresses the movement of the compound that is a catalyst for the hydrolysis reaction (estimated as a liquid crystal decomposed product). It is presumed that the spread of the gas is progressing.
  • a compound having a low acrylic equivalent is preferable from the viewpoint of the orientation of the specific liquid crystal compound described above. Specifically, a compound having an acrylic equivalent of 120 or less is preferred, a compound having an acrylic equivalent of 100 or less is more preferred, and a compound having an acrylic equivalent of 90 or less is still more preferred.
  • the acrylic equivalent is obtained by dividing the molecular weight by the number of acrylic functional groups.
  • non-liquid crystalline polyfunctional polymerizable compounds include esters of polyhydric alcohol and (meth) acrylic acid (eg, ethylene glycol di (meth) acrylate, 1,4-cyclohexane diacrylate, pentaerythritol tetra ( (Meth) acrylate, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipenta Erythritol hexa (meth) acrylate, 1,2,3-cyclohexanetetramethacrylate, polyurethane polyacrylate, polyester polyacrylate), vinylbenzene and derivatives thereof (eg, 1 4- divinylbenzene, 4-vinylbenzoic acid-2-
  • the content of the non-liquid crystalline polyfunctional polymerizable compound is from 0.1 to 0.1 in terms of the solid concentration of the polymerizable liquid crystal composition from the viewpoint of the occurrence of retardation of the formed optically anisotropic layer.
  • the amount is preferably 20% by mass, more preferably 0.1 to 10% by mass, even more preferably 1 to 6% 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 ultraviolet irradiation.
  • Examples of the photopolymerization initiator include ⁇ -carbonyl compounds (described in US Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (described in US Pat. No. 2,448,828), and ⁇ -hydrocarbon-substituted aromatics Group acyloin compounds (described in US Pat. No. 2,722,512), polynuclear quinone compounds (described in US Pat. Nos.
  • the polymerization initiator is preferably an oxime-type polymerization initiator because the durability of the optically anisotropic layer becomes better, and specifically, it is represented by the following formula (III). More preferably, the polymerization initiator is
  • X represents a hydrogen atom or a halogen atom
  • Y represents a monovalent organic group
  • Ar 3 represents a divalent aromatic group
  • L 6 represents a divalent organic group having 1 to 12 carbon atoms
  • R 10 represents an alkyl group having 1 to 12 carbon atoms.
  • examples of the halogen atom represented by X include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a chlorine atom is preferable.
  • the divalent aromatic group represented by Ar 3 is selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring exemplified as Ar 2 in the formula (II). Examples thereof include a divalent group having at least one aromatic ring.
  • examples of the divalent organic group having 1 to 12 carbon atoms represented by L 6 include a linear or branched alkylene group having 1 to 12 carbon atoms.
  • the alkyl group having 1 to 12 carbon atoms represented by R 10 specifically, for example, a methyl group, an ethyl group, a propyl group and the like are suitably mentioned.
  • examples of the monovalent organic group represented by Y include a functional group containing a benzophenone skeleton ((C 6 H 5 ) 2 CO).
  • a functional group containing a benzophenone skeleton in which a terminal benzene ring is unsubstituted or monosubstituted such as groups represented by the following formulas (2a) and (2b), is preferable.
  • * represents a bonding position, that is, a bonding position with a carbon atom of the carbonyl group in the formula (III).
  • Examples of the oxime-type polymerization initiator represented by the above formula (III) include a compound represented by the following formula S-1 and a compound represented by the following formula S-2.
  • the content of the polymerization initiator is not particularly limited, the content of the polymerization initiator is 0.5 parts with respect to 100 parts by mass of the specific liquid crystal compound contained in the polymerizable liquid crystal composition of the present invention.
  • the amount is preferably from 10 to 10 parts by mass, more preferably from 1 to 5 parts by mass.
  • the polymerizable liquid crystal composition of the present invention can contain an alignment controlling agent, if necessary.
  • an alignment controlling agent for example, a low molecular alignment controlling agent or a high molecular alignment controlling agent can be used.
  • Examples of the low-molecular alignment controlling agent include paragraphs 0009 to 0083 of JP-A-2002-20363, paragraphs 0111 to 0120 of JP-A-2006-106662, and paragraphs 0021-0029 of JP-A-2012-211306. The description can be taken into consideration, and the contents are incorporated in the present specification.
  • the polymer orientation controlling agent for example, the description in paragraphs 0021 to 0057 of JP-A-2004-198511 and the paragraphs 0121 to 0167 of JP-A-2006-106662 can be referred to. Is incorporated herein.
  • the amount of the alignment controlling agent to be used is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass of the solid content of the liquid crystal composition of the present invention in the polymerizable composition. .
  • the alignment controlling agent for example, a homogeneous alignment state in which the liquid crystal compound of the present invention is aligned in parallel with the surface of the layer can be obtained.
  • the polymerizable liquid crystal composition of the present invention preferably contains an organic solvent from the viewpoint of workability for forming an optically anisotropic layer and the like.
  • organic solvent include ketones (eg, acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, etc.), ethers (eg, dioxane, tetrahydrofuran, etc.), aliphatics Hydrocarbons (eg, hexane, etc.), alicyclic hydrocarbons (eg, cyclohexane, etc.), aromatic hydrocarbons (eg, toluene, xylene, trimethylbenzene, etc.), halogenated carbons (eg, dichloromethane, dichloroethane, etc.) , Dichlorobenzene, chlorotoluene, etc.), esters (eg, acetone, 2-butanone
  • Cellosolve, ethyl cellosolve, etc. may be used alone. More than one species may be used in combination.
  • the polymerizable liquid crystal composition of the present invention may contain components other than the above-described components.
  • a liquid crystal compound other than the above-described polymerizable liquid crystal compound a surfactant, a tilt angle controlling agent, an alignment assistant, and a plasticizer Agents and crosslinking agents.
  • the optically anisotropic layer according to the first embodiment of the present invention is an optically anisotropic layer obtained by polymerizing the above-mentioned polymerizable liquid crystal composition of the present invention.
  • Examples of the method for forming the optically anisotropic layer include a method in which the above-mentioned polymerizable liquid crystal composition of the present invention is brought into a desired alignment state, and then fixed 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 from 10 mJ / cm 2 to 50 J / cm 2 , more preferably from 20 mJ / cm 2 to 5 J / cm 2 , even more preferably from 30 mJ / cm 2 to 3 J / cm 2. , 50 to 1000 mJ / cm 2 .
  • the reaction may be carried out under heating conditions.
  • the optically anisotropic layer can be formed on an arbitrary support or a polarizer in the polarizing plate of the present invention described later.
  • the optically anisotropic layer according to the second aspect of the present invention is an optically anisotropic layer containing a compound having an oxetane structure and a polymer having a partial structure represented by the following formula (I). .
  • the compound having an oxetane structure is the same as the oxetane compound described in the polymerizable liquid crystal composition of the present invention described above. * -D 1- (Ar-D 2 ) p- * (I)
  • At least one of D 1 and D 2 in the above formula (I) is —O— or —CO— because the effect of improving the thermal durability of the polarizing plate becomes apparent.
  • it represents O-.
  • polymer having the partial structure represented by the above formula (I) for example, a polymer obtained by polymerizing the above-mentioned specific liquid crystal compound can be mentioned.
  • the thickness of the optically anisotropic layer according to the first and second aspects of the present invention is particularly limited. However, the thickness is preferably 1 to 5 ⁇ m, more preferably 1 to 4 ⁇ m, and still more preferably 1 to 3 ⁇ m.
  • the optically anisotropic layer of the present invention has an in-plane retardation value Re (450) measured at a wavelength of 450 nm, an in-plane retardation value Re (550) measured at a wavelength of 550 nm, and a wavelength of 650 nm. It is preferable that Re (650), which is the value of the in-plane retardation, has a relationship of Re (450) ⁇ Re (550) ⁇ Re (650). That is, this relationship can be said to represent the above-described inverse wavelength dispersion.
  • the method of measuring the in-plane retardation value at each wavelength is as described above.
  • 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 (positive A plate) has a refractive index in the slow axis direction in the film plane (direction in which the in-plane refractive index is maximized) nx, and is orthogonal to the in-plane slow axis in the plane.
  • the refractive index in the direction is ny and the refractive index in the thickness direction is nz
  • Rth of the positive A plate indicates a positive value.
  • a positive A plate can be obtained by horizontally aligning a rod-shaped polymerizable liquid crystal compound such as the above polymerizable liquid crystal composition.
  • a rod-shaped polymerizable liquid crystal compound such as the above polymerizable liquid crystal composition.
  • the positive A plate preferably functions as a ⁇ / 4 plate.
  • the ⁇ / 4 plate is a plate having a function of converting linearly polarized light of a specific wavelength into circularly polarized light (or circularly polarized light into linearly polarized light), and has an in-plane retardation Re ( ⁇ ) at a specific wavelength ⁇ nm.
  • a plate that satisfies Re ( ⁇ ) ⁇ / 4. This formula only needs to be achieved at any wavelength in the visible light range (for example, 550 nm), and the in-plane retardation Re (550) at the wavelength of 550 nm has a relationship of 110 nm ⁇ Re (550) ⁇ 160 nm. It is more preferable that the thickness satisfies 110 nm ⁇ Re (550) ⁇ 150 nm.
  • the optically anisotropic layer can be a positive C plate.
  • the positive C plate is defined as follows.
  • the positive C plate (positive C plate) has a refractive index in the slow axis direction in the film plane (direction in which the refractive index in the plane becomes maximum) nx, and is orthogonal to the slow axis in the plane in the plane.
  • the refractive index in the direction is ny and the refractive index in the thickness direction is nz
  • the relationship of the formula (A1) is satisfied.
  • Rth indicates a negative value.
  • nx ⁇ ny ⁇ nz Note that the above “ ⁇ ” includes not only a case where both are completely the same but also a case where both are substantially the same. “Substantially the same” means, for example, “nx (ny” also when (nx ⁇ ny) ⁇ d (where d is the thickness of the film) is ⁇ 10 to 10 nm, preferably ⁇ 5 to 5 nm. include. In the positive C plate, Re ⁇ ⁇ ⁇ ⁇ 0 according to the above definition.
  • a positive C plate can be obtained by vertically aligning a rod-shaped polymerizable liquid crystal compound.
  • descriptions in JP-A-2017-187732, JP-A-2016-53709, and JP-A-2015-200861 can be referred to.
  • the polarizing plate of the present invention has the above-described optically anisotropic layer of the present invention and a polarizer.
  • FIG. 1A, FIG. 1B, FIG. 1C, and FIG. 1D are schematic sectional views showing an example of the polarizing plate of the present invention.
  • the polarizing plate 10 shown in FIG. 1A is a polarizing plate having a layer configuration including a polarizer protective film 11, a polyvinyl alcohol polarizer film 12, a polarizer protective film 13, and a positive A plate 14 in this order.
  • the polarizing plate 30 shown in FIG. 1C is a polarizing plate having a layer structure including a polarizer protective film 11, a polyvinyl alcohol polarizer film 12, a positive A plate 14, and a positive C plate 15 in this order.
  • 1D has a layer configuration including a polarizer protective film 11, a polyvinyl alcohol polarizer film 12, a polarizer protective film 13, a photo-alignment film 16, a positive A plate 14, and a positive C plate 15 in this order. Is a polarizing plate.
  • the polarizer of the polarizing plate of the present invention is a so-called linear polarizer having a function of converting light into specific linearly polarized light.
  • the polarizer is not particularly limited, but an absorption polarizer can be used.
  • a commonly used polarizer containing polyvinyl alcohol as a main component can be used. For example, it is produced by adsorbing iodine or a dichroic dye on polyvinyl alcohol and stretching.
  • Mainly containing polyvinyl alcohol means that the solid content is 50% or more by weight percent.
  • polyvinyl alcohol is very hydrophilic and has high water absorption, and has a very large contribution to the water content of the entire polarizing plate. It is possible to adjust the water content by changing the drying conditions during the production of the polarizer or reducing the thickness of the polarizer. Further, as described in JP-A-2015-129826, a 4 ⁇ m-thick polyvinyl alcohol layer is obtained by dyeing and stretching a laminate obtained by forming a 9 ⁇ m-thick polyvinyl alcohol layer on a non-liquid crystal PET substrate. And it is also preferable to use such a method.
  • a liquid crystal compound and a dichroic azo dye are used as a polarizer without using polyvinyl alcohol as a binder.
  • a coating type polarizer produced by coating or the like using a dichroic azo dye used for the light-absorbing anisotropic film described in Japanese Patent Application Laid-Open (JP-A) No. 2002-222, is preferable.
  • the thickness of the polarizer is not particularly limited, it is preferably 5 to 20 ⁇ m, more preferably 3 to 15 ⁇ m, and further preferably 2 to 10 ⁇ m. By reducing the thickness of the polarizer, not only the thickness of the display device can be reduced, but also the water content can be further reduced, and the heat durability can be further improved.
  • the polarizing plate of the present invention may have a support for supporting the optically anisotropic layer.
  • a support layer is preferably transparent, and specifically, preferably has a light transmittance of 80% or more.
  • Examples of such a support include a glass substrate and a polymer film.
  • Examples of the material of the polymer film include a cellulose-based polymer and an acrylic-based polymer having an acrylate polymer such as polymethyl methacrylate and a lactone ring-containing polymer.
  • thermoplastic norbornene-based polymer polycarbonate-based polymer; polyester-based polymer such as polyethylene terephthalate and polyethylene naphthalate; styrene-based polymer such as polystyrene, acrylonitrile-styrene copolymer (AS resin); polyethylene, polypropylene, ethylene-propylene Polyolefin polymers such as polymers; vinyl chloride polymers; amide polymers such as nylon and aromatic polyamide; imide polymers; sulfone polymers; Polyether ether ketone polymer; polyphenylene sulfide polymer; vinylidene chloride polymer; vinyl alcohol polymer; vinyl butyral polymer; arylate polymer; polyoxymethylene polymer; epoxy polymer; Mixed polymers are included. Further, an embodiment in which the above-described polarizer also serves as such a support may be adopted.
  • the thickness of the support is not particularly limited, but is preferably 5 to 80 ⁇ m, more preferably 10 to 40 ⁇ m.
  • the polarizing plate of the present invention has any of the above-mentioned supports, it is preferable that the polarizing plate has an alignment film between the support and the optically anisotropic layer. Note that the above-described support may also function as an alignment film.
  • a technique for bringing molecules of a liquid crystal compound into a desired alignment state is used.
  • a liquid crystal compound is formed using an alignment film.
  • a technique for orienting in a desired direction is general.
  • LB Liuir-Blodgett
  • an alignment film or the like that generates an alignment function by light irradiation may be used.
  • the alignment film a film formed by rubbing the surface of a layer containing an organic compound such as a polymer (polymer layer) can be preferably used.
  • the rubbing treatment is performed by rubbing the surface of the polymer layer several times with paper or cloth in a certain direction (preferably, the longitudinal direction of the support).
  • the polymer used for forming the alignment film include polyimide, polyvinyl alcohol, modified polyvinyl alcohol described in paragraphs [0071] to [0095] of Japanese Patent No. 3907735, and polymerization described in JP-A-9-152509. It is preferable to use a polymer having a functional group.
  • the thickness of the alignment film is not particularly limited as long as it can exhibit the alignment function, but is preferably 0.01 to 5 ⁇ m, and more preferably 0.05 to 2 ⁇ m.
  • the alignment film it is also a preferable embodiment to use a so-called photo-alignment film (photo-alignment layer) as the alignment film, in which a photo-alignable material is irradiated with polarized or unpolarized light to form an alignment layer.
  • the optical alignment film is provided with an alignment regulating force by a step of irradiating polarized light from a vertical or oblique direction or a step of irradiating non-polarized light from an oblique direction.
  • the positive A plate formed using the photo-alignment film is particularly useful for optical compensation in a liquid crystal display device that does not require a pre-tilt angle of a driving liquid crystal as in an IPS (In-Place-Switching) mode liquid crystal display device. It is.
  • photo-alignment material used for the photo-alignment film for example, JP-A-2006-285197, JP-A-2007-76839, JP-A-2007-138138, JP-A-2007-94071, and JP-A-2007-94071 Azo compounds described in 121172, JP-A-2007-140465, JP-A-2007-156439, JP-A-2007-133184, JP-A-2009-109831, JP-A-3883848, and JP-A-4151746 Aromatic ester compounds described in JP-A-2002-229039, maleimide and / or alkenyl-substituted nadimide compounds having photo-alignable units described in JP-A-2002-265541 and JP-A-2002-317013, No.
  • the thickness of the alignment film is not particularly limited, but from the viewpoint of relaxing the surface unevenness that may be present on the support to form an optically anisotropic film having a uniform thickness, from 0.01 to 0.01. It is preferably 10 ⁇ m, more preferably 0.01 to 1 ⁇ m, and even more preferably 0.01 to 0.5 ⁇ m.
  • a polarizer protective film may be disposed on the surface of the polarizer.
  • the polarizer protective film may be disposed only on one surface of the polarizer (on the surface opposite to the optically anisotropic layer side), or may be disposed on both surfaces of the polarizer.
  • the structure of the polarizer protective film is not particularly limited, and may be, for example, a transparent support or a hard coat layer, or a laminate of the transparent support and the hard coat layer.
  • the hard coat layer a known layer can be used, and for example, a layer obtained by polymerizing and curing a polyfunctional monomer may be used.
  • a known transparent support can be used as the transparent support.
  • a cellulose-based polymer represented by triacetyl cellulose hereinafter, referred to as “cellulose acylate”) "
  • Thermoplastic norbornene-based resins ZEONEX, ZEONOR, manufactured by Nippon Zeon Co., Ltd., ARTON, manufactured by JSR Corporation
  • acrylic resins polyester-based resins
  • polystyrene-based resins a cellulose-based polymer represented by triacetyl cellulose (hereinafter, referred to as “cellulose acylate”) "), Thermoplastic norbornene-based resins (ZEONEX, ZEONOR, manufactured by Nippon Zeon Co., Ltd., ARTON, manufactured by JSR Corporation), acrylic resins, polyester-based resins, and polystyrene-based resins.
  • Resin which does not easily contain water, such as thermoplastic norbornene resin and polystyrene resin is preferable for suppressing the total water content of the
  • An adhesive layer or an adhesive layer may be arranged between the layers to ensure the adhesion between the layers. Further, a transparent support may be arranged between the layers.
  • the polarizing plate of the present invention preferably has a water content of 5.0 g / m 2 or less, more preferably 3.0 g / m 2 or less, still more preferably 1.5 g / m 2 or less, and 0.8 g / m 2 or less. Particularly preferred.
  • the polarizing plate can be preferably used for an organic electroluminescent device (preferably, an organic EL (electroluminescence) display device) or a liquid crystal display device.
  • the liquid crystal display device of the present invention is an example of an image display device, and includes the above-described 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 front polarizing plate, and the polarizing plate of the present invention as the front and rear polarizing plates. It is more preferable to use Further, it is preferable that the optically anisotropic layer included in the polarizing plate is disposed on the liquid crystal cell side. That is, the optically anisotropic layer of the present invention can be suitably used as an optical compensation film.
  • the liquid crystal cell constituting the liquid crystal display device will be described in detail.
  • the liquid crystal cell used in the liquid crystal display device is preferably a VA (Vertical Alignment) mode, an OCB (Optical Compensated Bend) mode, an IPS (In-Place-Switching) mode, or a TN (Twisted Nematic).
  • VA Vertical Alignment
  • OCB Optical Compensated Bend
  • IPS In-Place-Switching
  • TN Transmission Nematic
  • the present invention is not limited to this.
  • the rod-like liquid crystalline molecules are substantially horizontally aligned when no voltage is applied, and further twist-aligned at 60 to 120 °.
  • TN mode liquid crystal cells are most frequently used as color TFT liquid crystal display devices, and are described in many documents.
  • VA mode liquid crystal cell rod-like liquid crystalline molecules are substantially vertically aligned when no voltage is applied.
  • the VA mode liquid crystal cell includes (1) a VA mode liquid crystal cell in a narrow sense in which rod-like liquid crystal molecules are aligned substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied. 176625), (2) a liquid crystal cell (SID97, Digest of tech. Papers (preliminary collection) 28 (1997) 845) in which the VA mode is multi-domain (for MVA mode) in order to enlarge the viewing angle.
  • n-ASM mode liquid crystal cell in which rod-like liquid crystal molecules are substantially vertically aligned when no voltage is applied, and twisted multi-domain alignment when voltage is applied (Preprints 58 to 59 of the Japanese Liquid Crystal Symposium) (1998)) and (4) SURVIVAL mode liquid crystal cell (presented at LCD International 98).
  • PVA Powerned Vertical Alignment
  • Optical Alignment Optical Alignment
  • PSA Polymer-Sustained Alignment
  • IPS mode liquid crystal cell rod-shaped liquid crystal molecules are oriented substantially parallel to the substrate, and the liquid crystal molecules respond planarly when an electric field parallel to the substrate surface is applied.
  • black display is performed when no electric field is applied, and the absorption axes of a pair of upper and lower polarizing plates are orthogonal to each other.
  • Japanese Patent Application Laid-Open Nos. H10-54982 and H11-202323 disclose a method of using an optical compensation sheet (optical compensation film) to reduce leakage light at the time of black display in an oblique direction and improve the viewing angle. It is disclosed in JP-A-9-292522, JP-A-11-133408, JP-A-11-305217, JP-A-10-307291, and the like.
  • Organic EL display As an organic EL display device which is an example of the organic electroluminescent device of the present invention, for example, an embodiment having the polarizing plate of the present invention and the organic EL display panel in this order from the viewing side is preferable.
  • the optically anisotropic layer included in the polarizing plate is preferably arranged on the organic EL display panel side. That is, the optically anisotropic layer of the present invention is used as a so-called antireflection film.
  • the organic EL display panel is a display panel configured using an organic EL element having an organic light-emitting layer (organic electroluminescent layer) sandwiched 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 employed.
  • a roll-shaped polyvinyl alcohol film having a thickness of 60 ⁇ m was continuously stretched 5 times in an MD (Machine Direction) direction in an aqueous iodine solution and dried to obtain a 12 ⁇ m-thick polarizer (polarizing film).
  • a linear polarizing plate 1 was prepared by laminating a cellulose triacetate film TJ25 as a polarizer protective film which had been subjected to the alkali saponification treatment on both surfaces of the above polarizer.
  • the film was further dried by being conveyed between rolls of a heat treatment apparatus to produce a cellulose acylate film 1 having a thickness of 40 ⁇ m.
  • the core layer in the cellulose acylate film 1 had a thickness of 36 ⁇ m, and the outer layers disposed on both sides of the core layer each had a thickness of 2 ⁇ m.
  • the in-plane retardation of the obtained cellulose acylate film 1 was 0 nm.
  • the produced photo-alignment film 1 was irradiated with ultraviolet light using an ultra-high pressure mercury lamp in the atmosphere.
  • a wire grid polarizer (ProFlux PPL02, manufactured by Moxtek) was set so as to be parallel to the surface of the photo-alignment film 1 and exposed to perform photo-alignment treatment.
  • the illuminance of the ultraviolet light used at this time was 10 mJ / cm 2 in the UV-A region (ultraviolet A wave, integration of wavelength 380 nm to 320 nm).
  • a coating solution A-1 for forming a positive A plate A-1 was applied on the surface of the photo-alignment film 1 having been subjected to the photo-alignment treatment using a bar coater. After aging by heating at a film surface temperature of 100 ° C. for 20 seconds and cooling to 90 ° C., the film was irradiated with ultraviolet rays of 300 mJ / cm 2 using an air-cooled metal halide lamp (manufactured by Eye Graphics Co., Ltd.) in air to obtain nematic. The optically anisotropic layer 1 (positive A plate A1) was formed by fixing the alignment state.
  • the formed positive A plate A1 had a thickness of 2.5 ⁇ m and the slow axis direction was orthogonal to the absorption axis of the polarizing plate (that is, the specific liquid crystal compound was orthogonal to the absorption axis of the polarizing plate). Orientation).
  • the dependency of Re on the light incident angle and the tilt angle of the optical axis were measured using an automatic birefringence meter (KOBRA-21ADH, manufactured by Oji Scientific Instruments).
  • Re is 145 nm
  • Rth is 73 nm
  • Re (550) / Re (450) is 1.12
  • Re (650) / Re (550) is 1.01
  • the tilt angle of the optical axis is 0 °
  • the specific liquid crystal compound was a homogeneous orientation.
  • a plate coating solution A8 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A7, except that oxetane compound A-1 was not mixed in positive A plate forming coating solution A7.
  • the following specific liquid crystal compound L-9 was used in an amount of 100 parts by mass instead of the polymerizable liquid crystal compound X-1, the specific liquid crystal compound L-1, and the specific liquid crystal compound L-2. Except for the above, a coating solution A9 for forming a positive A plate was prepared in the same manner as the coating solution A1 for forming a positive A plate.
  • a plate coating solution A10 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A9, except that oxetane compound A-1 was not blended in positive A plate forming coating solution A9.
  • a coating solution A11 for forming a positive A plate having the following composition was prepared.
  • a plate coating solution A12 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A11, except that oxetane compound A-1 was not blended in positive A plate forming coating solution A11.
  • a coating solution A13 for forming a positive A plate having the following composition was prepared.
  • ⁇ Composition of the coating solution A13 for forming the positive A plate --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- -100.00 parts by mass of the following specific liquid crystal compound L-5-3.00 parts by mass of polymerization initiator Irgacure 369 (BASF Japan)-3.00 parts by mass of polymerization initiator OXE-03 (BASF Japan)-Adeka Cruz NCI-831 (ADEKA) 3.00 parts by mass. 4.00 parts by mass of the oxetane compound A-1.
  • Positive A plate coating solution A14 was prepared in the same manner as Positive A plate forming coating solution A13, except that oxetane compound A-1 was not blended in Positive A plate forming coating solution A13.
  • the positive A plate forming coating solution A13 was prepared in the same manner as the positive A plate forming coating solution A13 except that the following specific liquid crystal compound L-7 was used in place of the specific liquid crystal compound L-5 in the coating solution A13.
  • a coating solution A15 was prepared.
  • a coating solution A16 for a positive A plate was prepared in the same manner as the coating solution A15 for a positive A plate except that the oxetane compound A-1 was not added to the coating solution A15 for forming a positive A plate.
  • the positive A plate forming coating solution A13 was prepared in the same manner as the positive A plate forming coating solution A13 except that the following specific liquid crystal compound L-8 was used in place of the specific liquid crystal compound L-5 in the coating liquid A13 for forming a positive A plate.
  • Application liquid A17 was prepared.
  • a plate coating solution A18 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A17, except that oxetane compound A-1 was not mixed in positive A plate forming coating solution A17.
  • the positive A plate forming coating solution A13 was prepared in the same manner as the positive A plate forming coating solution A13, except that the following specific liquid crystal compound L-10 was used in place of the specific liquid crystal compound L-5.
  • a coating solution A19 was prepared.
  • a plate coating solution A20 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A19, except that oxetane compound A-1 was not added to positive A plate forming coating solution A19.
  • the positive A plate forming coating solution A13 was prepared in the same manner as the positive A plate forming coating solution A13 except that the following specific liquid crystal compound L-11 was used in place of the specific liquid crystal compound L-5.
  • Application liquid A21 was prepared.
  • a plate coating solution A22 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A21, except that oxetane compound A-1 was not blended in positive A plate forming coating solution A21.
  • the positive A plate forming coating solution A13 was prepared in the same manner as the positive A plate forming coating solution A13 except that the following specific liquid crystal compound L-12 was used in place of the specific liquid crystal compound L-5 in the positive A plate forming coating solution A13.
  • Application liquid A23 was prepared.
  • a plate coating solution A24 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A23, except that oxetane compound A-1 was not added to positive A plate forming coating solution A23.
  • the positive A plate forming coating solution A13 was prepared in the same manner as the positive A plate forming coating solution A13 except that the following specific liquid crystal compound L-13 was used in place of the specific liquid crystal compound L-5 in the coating liquid A13 for forming a positive A plate.
  • a coating solution A25 was prepared.
  • a plate coating solution A26 for forming positive A plate was prepared in the same manner as positive A plate forming coating solution A25, except that oxetane compound A-1 was not blended in positive A plate forming coating solution A25.
  • Polarizing plates 2 to 26 were prepared in the same manner as for polarizing plate 1, except that the coating solutions shown in Table 3 below were used instead of the coating solution A1 for forming a positive A plate.
  • the polarizing plate manufactured in each of the above-described manufacturing examples was sandwiched between glass plates using the adhesive 1 from both sides while maintaining the water content.
  • the retardation (Re) value at a wavelength of 550 nm was measured using Axo Scan (0 PMF-1, manufactured by Axometrics) and evaluated by the following index. The results are shown in Table 3 below. Specifically, the difference ( ⁇ Re) between the initial (immediately after production) Re value and the Re after being left for 400 hours in an environment of 80 ° C. was calculated.
  • Re improvement ratio [( ⁇ Re of comparative example not containing oxetane compound) ⁇ ( ⁇ Re of example containing oxetane compound)] / ( ⁇ Re of example containing oxetane compound)
  • a coating solution for forming an alignment layer having the following composition was continuously applied using a # 8 wire bar. Drying was performed with hot air at 60 ° C. for 60 seconds and further with hot air at 100 ° C. for 120 seconds to form an alignment layer.
  • Composition of coating liquid for forming alignment layer ⁇ -2.4 parts by mass of polyvinyl alcohol (Kuraray, PVA103)-1.6 parts by mass of isopropyl alcohol-36 parts by mass of methanol-60 parts by mass of water ⁇
  • the following coating solution C-1 for forming a positive C plate is coated on the cellulose acylate film 2 having an alignment layer formed as described above, and the coating solution is aged at 60 ° C. for 60 seconds, and then 70 mW / cm 2 in air.
  • the polymerizable rod-shaped liquid crystal compound is vertically aligned by irradiating an ultraviolet ray of 1000 mJ / cm 2 using an air-cooled metal halide lamp (manufactured by Eye Graphics Co., Ltd.) to vertically align the polymerizable rod-like liquid crystal compound. 1 was produced.
  • Rth was ⁇ 60 nm at a wavelength of 550 nm.
  • the isolated touch panel is pasted again to the organic EL display element, and the polarizing plates 27 to 40 produced above are pasted on the touch panel so that the positive C plate side becomes the panel side. Produced.
  • Polarizer protective film 10
  • Polarizer protective film 12
  • Polyvinyl alcohol polarizer 13
  • Polarizer protective film 14
  • a plate 15

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  • Polarising Elements (AREA)

Abstract

La présente invention aborde le problème de la fourniture d'une composition de cristaux liquides polymérisable par laquelle une plaque de polarisation ayant une excellente durabilité thermique peut être fabriquée, une couche optiquement anisotrope, une plaque de polarisation, un dispositif d'affichage à cristaux liquides et un dispositif électroluminescent organique. Cette composition de cristaux liquides polymérisable contient un composé ayant une structure oxétane, et un composé de cristaux liquides polymérisable représenté par la formule (II). (II) : L1-G1-D1-(Ar-D(2)p-G2-L2
PCT/JP2019/034088 2018-09-14 2019-08-30 Composition de cristaux liquides polymérisable, couche optiquement anisotrope, plaque de polarisation, dispositif d'affichage à cristaux liquides et dispositif électroluminescent organique Ceased WO2020054459A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003096066A (ja) * 2001-09-20 2003-04-03 Nippon Oil Corp 液晶性オキセタン化合物、重合性液晶性組成物、液晶フィルムの製造方法、光学フィルムおよび液晶表示装置
JP2014219659A (ja) * 2013-04-11 2014-11-20 Jnc株式会社 剥離防止剤を含有した重合性液晶組成物を用いたフィルム
JP2016053709A (ja) * 2014-03-31 2016-04-14 富士フイルム株式会社 光学フィルム、偏光板、および光学フィルムの製造方法
WO2018123832A1 (fr) * 2016-12-27 2018-07-05 富士フイルム株式会社 Film optique et procédé de fabrication associé

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003096066A (ja) * 2001-09-20 2003-04-03 Nippon Oil Corp 液晶性オキセタン化合物、重合性液晶性組成物、液晶フィルムの製造方法、光学フィルムおよび液晶表示装置
JP2014219659A (ja) * 2013-04-11 2014-11-20 Jnc株式会社 剥離防止剤を含有した重合性液晶組成物を用いたフィルム
JP2016053709A (ja) * 2014-03-31 2016-04-14 富士フイルム株式会社 光学フィルム、偏光板、および光学フィルムの製造方法
WO2018123832A1 (fr) * 2016-12-27 2018-07-05 富士フイルム株式会社 Film optique et procédé de fabrication associé

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