[go: up one dir, main page]

WO2022059470A1 - Composition de cristaux liquides, composé, film optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image - Google Patents

Composition de cristaux liquides, composé, film optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image Download PDF

Info

Publication number
WO2022059470A1
WO2022059470A1 PCT/JP2021/031726 JP2021031726W WO2022059470A1 WO 2022059470 A1 WO2022059470 A1 WO 2022059470A1 JP 2021031726 W JP2021031726 W JP 2021031726W WO 2022059470 A1 WO2022059470 A1 WO 2022059470A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
substituent
liquid crystal
hydrogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2021/031726
Other languages
English (en)
Japanese (ja)
Inventor
有次 吉田
徹 渡辺
愛子 吉田
淳 石山
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujifilm Corp
Original Assignee
Fujifilm Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fujifilm Corp filed Critical Fujifilm Corp
Priority to JP2022550441A priority Critical patent/JP7538237B2/ja
Priority to KR1020237008575A priority patent/KR102851512B1/ko
Priority to CN202180063766.2A priority patent/CN116249757B/zh
Publication of WO2022059470A1 publication Critical patent/WO2022059470A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D277/82—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
    • C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
    • C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
    • 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
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G02B5/3016—Polarising elements involving passive liquid crystal 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
    • G02F1/133528—Polarisers
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
    • 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

Definitions

  • the present invention relates to a liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device.
  • the polymerizable liquid crystal compound exhibiting reverse wavelength dispersibility is a thin film of a retardation film (optically anisotropic film) because it enables accurate conversion of light wavelength over a wide wavelength range and has a high refractive index. Since it has characteristics such as being able to be transformed, it is being actively researched. Further, as a polymerizable liquid crystal compound exhibiting reverse 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 long wavelength. Is required to be.
  • Patent Document 1 describes a polymerizable liquid crystal compound represented by the following formula (1) ([Claim 1]).
  • the present inventors have studied the polymerizable liquid crystal compound described in Patent Document 1, and found that an optically anisotropic film is formed depending on other components of the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound. It was clarified that an orientation defect may occur in the liquid crystal display.
  • the present inventors have formed an optically anisotropic film by using a liquid crystal composition containing a liquid crystal compound and a compound represented by the formula (II) described later.
  • the present invention has been completed by finding that it is possible to suppress the orientation defect of the liquid crystal display. That is, it was found that the above problem can be achieved by the following configuration.
  • a liquid crystal composition containing a liquid crystal compound and a compound represented by the formula (II) described later [2] The liquid crystal composition according to [1], wherein at least one M in the formula (II) described later represents an aromatic ring having a maximum absorption wavelength of 280 to 420 nm. [3] At least one M in the formula (II) described later represents any aromatic ring selected from the group consisting of the groups represented by the formulas (M-1) to (M-7) described later. , [1] or [2]. [4] The liquid crystal composition according to any one of [1] to [3], wherein T in the formula (II) described later represents a polymerizable group.
  • T in the formula (II) described later represents any polymerizable group selected from the group consisting of the groups represented by the formulas (P-1) to (P-20) described later.
  • [6] The liquid crystal composition according to any one of [1] to [5], wherein the liquid crystal compound has a reverse wavelength dispersibility.
  • the liquid crystal compound is a compound having any aromatic ring selected from the group consisting of groups represented by the formulas (Ar-1) to (Ar-7) described later, [1] to [6].
  • the liquid crystal composition according to any one of. [8] The liquid crystal composition according to any one of [1] to [7], wherein the liquid crystal compound has a polymerizable group.
  • the liquid crystal display according to [8], wherein the polymerizable group represents any polymerizable group selected from the group consisting of groups represented by the formulas (P-1) to (P-20) described later. Composition.
  • a compound represented by the formula (II) described later [11] The compound according to [10], wherein at least one M in the formula (II) described later represents an aromatic ring having a maximum absorption wavelength of 280 to 420 nm. [12] At least one M in the formula (II) described later represents any aromatic ring selected from the group consisting of the groups represented by the formulas (M-1) to (M-7) described later. , [10] or [11]. [13] The compound according to any one of [10] to [12], wherein T in the formula (II) described later represents a polymerizable group. [14] T in the formula (II) described later represents any polymerizable group selected from the group consisting of the groups represented by the formulas (P-1) to (P-20) described later. 10] The compound according to any one of [13].
  • [15] An optically anisotropic film obtained by polymerizing the liquid crystal composition according to any one of [1] to [9].
  • [16] The optically anisotropic film according to [15], which satisfies the formula (III) described later.
  • [17] An optical film having the optically anisotropic film according to [15] or [16].
  • [18] A polarizing plate having the optical film according to [17] and a polarizing element.
  • An image display device having the optical film according to [17] or the polarizing plate according to [18].
  • liquid crystal composition a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device capable of suppressing the occurrence of orientation defects in the optically anisotropic film.
  • 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 the representative embodiments of the present invention, but the present invention is not limited to such embodiments.
  • 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 described later (for example)
  • D 1 in I) is -CO-NR-
  • the position bonded to the G 1 side is * 1 and the position bonded to the Ar 1 side is * 2
  • D 1 is * 1.
  • -CO-NR- * 2 may be used, or * 1-NR-CO- * 2 may be used.
  • the liquid crystal composition of the present invention is a liquid crystal composition containing a liquid crystal compound and a compound represented by the formula (II) described later (hereinafter, also abbreviated as "specific compound").
  • the specific compound contained in the liquid crystal composition of the present invention is a compound represented by the following formula (II).
  • R 21 and R 22 each independently represent a hydrogen atom or an alkyl group.
  • R 23 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group.
  • SP 21 and SP 22 each independently represent a single bond or an alkylene group.
  • the hydrogen atom contained in the alkylene group 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 a carbon number of 1 to 20. It may be substituted with an alkyl group.
  • the -CH 2- constituting the alkylene group one or two or more -CH 2 -that are not adjacent to each other are -O-, -S-, -CO-, -COO-, -OCO-.
  • M represents an aromatic ring, an alicyclic ring, or a heterocycle which may have a substituent.
  • m represents an integer of 3 or more, and the plurality of Ms may be the same or different, and the plurality of D 22s may be the same or different. You may.
  • T represents a hydrogen atom, an alkyl group, or a polymerizable group.
  • substituent X include, for example, an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, and an alkylamino.
  • substituent X include a group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group, and an N-alkylcarbamate group, among which an alkyl group, an alkoxy group and an alkoxy group are used.
  • a carbonyl group, an alkylcarbonyloxy group, or a halogen atom 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).
  • -Butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group, etc.) are more preferable, an alkyl group having 1 to 4 carbon atoms is further preferable, and a methyl group or an ethyl group is particularly preferable.
  • 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 atom is preferable.
  • Alkoxy groups of -4 are more preferred, and methoxy or ethoxy groups are particularly preferred.
  • alkoxycarbonyl group examples 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, 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.
  • examples of the alkyl group represented by one aspect of R 21 and R 22 include the same alkyl groups as those exemplified for the above-mentioned substituent X. Further, as R 21 and R 22 , it is preferable to represent a methyl group.
  • R 23 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group as described above, but preferably represents a hydrogen atom.
  • examples of the alkylene group represented by one aspect of SP 21 and SP 22 include a linear or branched alkylene group having 1 to 12 carbon atoms, and specifically, a methylene group. , Ethylene group, propylene group, butylene group, pentylene group, hexylene group, methylhexylene group, heptylene group and the like.
  • the hydrogen atom contained in the alkylene group is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, or a cyano.
  • the alkylene group shown in one aspect of SP 21 and SP 22 includes one or two or more non-adjacent-CH 2- among the -CH 2- constituting the alkylene group.
  • the SP 21 and SP 22 are one or adjacent to a linear alkylene group having 2 to 10 carbon atoms or a linear alkylene group having 2 to 12 carbon atoms.
  • a divalent linking group in which two or more -CH 2- are substituted with -O-, -COO- or -OCO-, and a linear alkylene group having 2 to 8 carbon atoms is preferable.
  • R 1 , R 2 and R 5 independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. Further, as D 21 and D 22 , it is preferable to represent a single bond, -CO-, -O-, or -CO-O-.
  • examples of the aromatic ring represented by one aspect of M include an aromatic ring having 6 to 20 carbon atoms, and specifically, a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring.
  • Aromatic hydrocarbon rings such as: Fran ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, benzothiazole ring and other aromatic heterocycles; represented by the formulas (M-1) to (M-8) described later.
  • examples of the alicyclic ring shown by one aspect of M include a cycloalkane ring, and specific examples thereof include a cyclohexane ring, a cyclopeptane ring, a cyclooctane ring, a cyclododecane ring, and a cyclododecane ring.
  • examples of the heterocycle indicated by one aspect of M include heterocycles other than the above-mentioned aromatic heterocycle, and specifically, for example, a tetrahydrofuran ring, a tetrahydropyran ring, a pyrrolidine ring, a piperidine ring, and a tetrahydrothiophene ring. And so on.
  • At least one M in the above formula (II) represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm for the reason that the optical anisotropic film formed has better light resistance. Is preferable. In particular, when the number of Ms is an odd number (for example, 3 or 5), it is preferable that the M located at the center represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm.
  • At least one M in the above formula (II) is represented by the following formulas (M-1) to (M-7) for the reason that the compatibility with the liquid crystal compound is good. It preferably represents any aromatic ring selected from the group consisting of groups. In particular, when there are an odd number of Ms (for example, 3 or 5), the M located at the center is a group consisting of groups represented by the following formulas (M-1) to (M-7). It is preferable to represent any aromatic ring selected from.
  • Q 1 represents N or CH
  • Q 2 represents -S-, -O-, or -N (R 6 )-
  • R 6 is hydrogen.
  • Y1 is an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent and 3 to 12 carbon atoms which may have a substituent.
  • the alkyl group having 1 to 6 carbon atoms indicated by R 6 is specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and the like. Examples thereof include a tert-butyl group, an n-pentyl group, and an n-hexyl group.
  • Examples of the 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 alicyclic hydrocarbon group having 6 to 20 carbon atoms indicated by Y 1 include a cyclohexylene group, a cyclopentylene group, a norbornene group, and an adamantylene group.
  • Examples of the substituent that Y 1 may have include the same as the above-mentioned substituent X.
  • Z 1 , Z 2 and Z 3 are independently hydrogen atoms, monovalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and carbon.
  • Nitro group, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 or -COR 12 where R 7 to R 12 are independently hydrogen atoms or 1 to 6 carbon atoms, respectively. Representing an alkyl group, Z 1 and Z 2 may be bonded to each other to form an aromatic ring.
  • an alkyl group having 1 to 15 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and specifically, a methyl group.
  • 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, A tert-butyl group is 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 [5.2.2.10 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
  • Specific examples of the monovalent aromatic heterocyclic group having 6 to 20 carbon atoms include a 4-pyridyl group, a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group. Can be mentioned.
  • halogen atom examples 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 7 to R 10 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.
  • Groups, tert-butyl group, n-pentyl group, n-hexyl group and the like can be mentioned.
  • Z 1 and Z 2 may be bonded to each other to form an aromatic ring as described above.
  • Z 1 and Z 2 in the above formula (M-1) may be bonded to each other to form an aromatic ring.
  • Examples of the formed structure include a group represented by the following formula (M-1a). In the following formula (M-1a), * represents a bonding position, and Q 1 , Q 2 and Y 1 are the same as those described in the above formula (M-1).
  • a 3 and A 4 are independently derived from -O-, -N (R 13 )-, -S-, and -CO-, respectively.
  • R 13 represents a hydrogen atom or a substituent. Examples of the substituent indicated by R 13 include the same as the above-mentioned substituent X.
  • X represents a non-metal atom of Group 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 consisting of a combination of two or more of these, and R 1 to R 5 are independent hydrogen atoms, respectively. It represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
  • R 1 , R 2 and R 5 independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. Of these, any of -CO-, -O-, and -CO-O- is preferable.
  • SP 3 and SP 4 are independently single-bonded, a linear or branched alkylene group having 1 to 12 carbon atoms, or a direct group having 1 to 12 carbon atoms.
  • One or more of -CH 2- constituting a chain or branched alkylene group is substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-.
  • examples of the linear or branched alkylene group having 1 to 12 carbon atoms shown in one aspect of SP 3 and SP 4 include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group and a hexylene group. , Methylhexylene group, heptylene group and the like are preferable.
  • one or more of -CH 2- constituting a linear or branched alkylene group having 1 to 12 carbon atoms are -O-, -S-, and -NH. It may be a divalent linking group substituted with ⁇ , ⁇ N (Q) ⁇ or ⁇ CO—, and the substituent represented by Q is, for example, the same as the above-mentioned substituent X. Can be 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.
  • a nitrogen atom, a sulfur atom and an oxygen atom are preferable.
  • 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 may have a substituent. Examples of the substituent include the same as the above-mentioned substituent X.
  • 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 an 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.
  • Q3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
  • Ax and Ay include those described in paragraphs [0039] to [0995] of International Publication No. 2014/010325.
  • Specific examples of the alkyl group having 1 to 20 carbon atoms indicated by Q3 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert.
  • -Butyl group, n-pentyl group, n-hexyl group and the like can be mentioned, and examples of the substituent include the same as the above-mentioned substituent X.
  • At least one M in the above formula (II) represents a cyclohexane ring for the reason that the orientation of the liquid crystal is improved and the moisture resistance of the formed optically anisotropic film is also improved.
  • M located outside the center represents a cyclohexane ring.
  • m represents an integer of 3 or more, preferably represents an integer of 3 to 6, and more preferably represents an odd number among the integers of 3 to 6.
  • the plurality of Ms may be the same or different from each other, and the plurality of D 22s may be the same or different from each other.
  • examples of the alkyl group represented by one aspect of T include the same alkyl groups as those exemplified for the above-mentioned substituent X.
  • T in the above formula (II) represents a polymerizable group for the reason that the strength of the formed optically anisotropic film is improved.
  • 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.
  • the acryloyloxy group is generally faster in terms of the 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.
  • the cationically polymerizable group 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, acryloyloxy group or methacryloyloxy group is more preferable. In the following equations (P-1) to (P-20), * represents the bonding position with SP 22 .
  • Specific examples of the specific compound include compounds represented by the following formulas (2-1-1) to (2-1-12) and (2-1) to (2-5).
  • the content of the specific compound is preferably 0.05 to 20% by mass with respect to the total mass of the liquid crystal compound and the specific compound described later. It is more preferably 1 to 10% by mass, and even more preferably 0.2 to 5% by mass.
  • liquid crystal compound contained in the liquid crystal composition of the present invention is not particularly limited, and conventionally known liquid crystal compounds can be used.
  • liquid crystal compounds can be classified into rod-shaped type and disk-shaped type according to their shape.
  • a polymer generally refers to a molecule 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, and it is more preferable to use a rod-shaped liquid crystal compound.
  • the liquid crystal compound preferably has a polymerizable group from the viewpoint of immobilizing the orientation of the liquid crystal compound.
  • a polymerizable group capable of radical polymerization or cationic polymerization is preferable.
  • the radically polymerizable group a generally 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 the 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 generally 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 group and the like.
  • 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 above-mentioned formulas (P-1) to (P-20). Of these, acryloyloxy group or methacryloyloxy group is more preferable.
  • the liquid crystal compound is preferably a liquid crystal compound having reverse wavelength dispersibility because it enables accurate conversion of the light wavelength in a wide wavelength range.
  • the liquid crystal compound having "reverse wavelength dispersibility" in the present specification measures the in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced by using the liquid crystal compound. When the measurement wavelength is increased, the Re value becomes equal or higher.
  • the liquid crystal compound is selected from the group consisting of the groups represented by the following formulas (Ar-1) to (Ar-7) for the purpose of achieving both reverse wavelength dispersibility and light resistance. It is preferable that the compound has one of the aromatic rings.
  • the liquid crystal compound is preferably a compound represented by the following formula (I) because it has a high refractive index anisotropy and therefore the optically anisotropic film can be thinned.
  • Ar represents any aromatic ring selected from the group consisting of the groups represented by the above-mentioned formulas (Ar-1) to (Ar-7).
  • q1 in the following formula (I) is 2, the plurality of Ars may be the same or different.
  • G 5 independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. However, when q1 is 2 , the plurality of D2s may be the same or different. Further, in the above formula (I), G 1 and G 2 each independently have an aromatic ring having 6 to 20 carbon atoms which may have a substituent or a carbon which may have a substituent. Represents a divalent alicyclic hydrocarbon group of number 5 to 20, and one or more of -CH 2- constituting the alicyclic hydrocarbon group is substituted with -O-, -S- or -NH-. May be.
  • a 1 and A 2 each independently have an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a carbon which may have a substituent.
  • SP 1 and SP 2 are independently single-bonded, 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 1 and L 2 each independently represent a monovalent organic group, and at least one of L 1 and L 2 represents a polymerizable group.
  • Ar is an aromatic ring represented by the above-mentioned formula (Ar - 3 )
  • at least one of L1 and L2 and L3 and L4 in the above-mentioned formula (Ar-3) are polymerized. Represents a sex group.
  • a1, a2, g1 and g2 are all preferably 1. Further, in the above formula (I), q1 is preferably 1.
  • examples of the aromatic ring having 6 to 20 carbon atoms represented by one aspect of G 1 and G 2 include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring.
  • Aromatic heterocycles such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring; among them, a benzene ring (for example, a 1,4-phenyl group) is preferable.
  • the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one aspect of 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 the content thereof is incorporated in the present specification. ..
  • G 1 and G 2 in the above formula (I) are preferably cycloalkane rings.
  • the cycloalkane ring include a cyclohexane ring, a cyclopeptane ring, a cyclooctane ring, a cyclododecane ring, a cyclododecane ring, and the like.
  • the cyclohexane ring is preferred, the 1,4-cyclohexylene group is more preferred, and the trans-1,4-cyclohexylene group is even more preferred.
  • G 1 and G 2 may have a substituent having an aromatic ring having 6 to 20 carbon atoms or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms. Can be the same as the substituent that Y 1 in the above formula (Ar-1) may have.
  • the aromatic rings having 6 to 20 or more carbon atoms shown in one aspect of A 1 and A 2 are the same as those described in G 1 and G 2 in the above formula (I). Can be mentioned.
  • the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one aspect of A 1 and A 2 in G 1 and G 2 in the above formula (I). Examples are similar to those described.
  • the substituents that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms may have are, for example, the above-mentioned substitutions.
  • the same as the group X can be mentioned.
  • Examples of the monovalent organic group represented by L 1 and L 2 in the above formula (I) include those similar to those described in L 3 and L 4 in the above formula (M-3).
  • examples of the polymerizable group represented by at least one of L 1 and L 2 include the above-mentioned radical polymerization or cationically polymerizable polymerizable group.
  • examples of particularly preferable polymerizable groups include any polymerizable group selected from the group consisting of the groups represented by the above-mentioned formulas (P-1) to (P-20). Of these, acryloyloxy group or methacryloyloxy group is more preferable.
  • both L 1 and L 2 in the above formula (I) are polymerizable groups, and are acryloyloxy group or methacryloyloxy group, for the reason that the durability is good. Is more preferable.
  • Examples of the compound represented by the above formula (I) include the compounds represented by the general formula (1) described in JP-A-2010-084032 (particularly, those described in paragraph numbers [0067] to [0073].
  • K side chain structure
  • K-1-1-1 to K-8-9 compounds having a side chain structure represented by the following K-1-1 to K-8-9.
  • “*" shown in the side chain structure represented by the following K-1-1 to K-8-9 represents the bonding position with the aromatic ring.
  • the group adjacent to the acryloyloxy group and the methacryloyl group, respectively represents a propylene group (a group in which a methyl group is replaced with an ethylene group), and is a methyl group. Represents a mixture of positional isomers at different positions.
  • the liquid crystal composition of the present invention may contain other polymerizable compounds having one or more polymerizable groups in addition to the above-mentioned specific compound and liquid crystal compound.
  • 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.
  • 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-2014-077068. 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 structure of the same publication can be used.
  • ]-[0035], [0042]-[0050], [0056]-[0057] Specific examples described in paragraphs may be mentioned.
  • the content is preferably less than 50% by mass, more preferably 40% by mass or less, based on the mass of the above-mentioned liquid crystal compound, 2 to 2 to. It is more preferably 30% by mass.
  • the 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. Nos. 2,376,661 and 236,670), acidoin ethers (described in US Pat. No. 2,448,828), and ⁇ -hydrogen-substituted fragrances.
  • Group acidloin compounds described in US Pat. No. 2,725,512
  • polynuclear quinone compounds described in US Pat. Nos.
  • the polymerization initiator is 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 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.
  • halogenated carbon solvents eg dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.
  • ester solvents eg, methyl acetate, etc.
  • Ethyl acetate, butyl acetate, etc. water, alcohol solvent (eg, ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolve solvent (eg, methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetate solvent, sulfoxide solvent (eg, methyl cellosolve, ethyl cellosolve, etc.)
  • dimethylsulfoxide and the like chain amide-based solvents (for example, dimethylformamide, dimethylacetamide, etc.) and the like can be mentioned, and
  • the 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 a fluorine-based leveling agent or a silicon-based leveling agent is preferable because it has a high leveling effect on the amount of addition, and a fluorine-based leveling agent is 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 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.
  • orientation control agent that promotes homogenius orientation for example, a small molecule orientation control agent or a polymer orientation control agent can be used.
  • the small molecule 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 the Publication 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 a boronic acid compound and an onium salt compound, and 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 consideration, the contents of which are incorporated herein by reference.
  • the cholesteric orientation can be realized by adding a chiral agent to the liquid crystal composition of the present invention, and the turning direction of the cholesteric orientation can be controlled by the direction of the chiral property.
  • the pitch of the cholesteric orientation can be controlled according to the orientation restricting force of the chiral agent.
  • the content is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, based on the total solid content mass in the liquid crystal composition. ..
  • 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 a 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 liquid crystal composition of the present invention.
  • the 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, a plasticizer, and the like. And a cross-linking agent and the like.
  • the compound of the present invention is a compound represented by the above-mentioned formula (II), and is the same as that described as a specific compound in the above-mentioned liquid crystal composition of the present invention.
  • the optically anisotropic film of the present invention is an optically anisotropic film obtained by polymerizing the above-mentioned liquid crystal composition of the present invention.
  • the method for forming the optically anisotropic film include a method of using the liquid crystal composition of the present invention described above to obtain 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 . , 50-1000 mJ / cm 2 is particularly preferable. Further, in order to promote the polymerization reaction, it may be carried out under heating conditions.
  • the optically anisotropic film can be formed on an arbitrary support in the optical film of the present invention described later or on a polarizing element in the polarizing plate of the present invention described later.
  • the optically anisotropic membrane of the present invention preferably satisfies the following formula (III). 0.50 ⁇ Re (450) / Re (550) ⁇ 1.00 ... (III)
  • Re (450) represents an in-plane lettering of the optically anisotropic film at a wavelength of 450 nm
  • Re (550) represents an in-plane letter of the optically anisotropic film at a wavelength of 550 nm.
  • the optically anisotropic film 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 phase axial direction (the direction in which the refractive index in the plane is maximized) in the film plane 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 in a positive A plate, for example, (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) x d 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 linear polarization of a specific wavelength into circular polarization (or circular polarization into linear polarization). 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 (hereinafter, these drawings are abbreviated as "FIG. 1" when no particular distinction is required) are schematic cross-sectional views showing an example of the optical film of the present invention, respectively.
  • FIG. 1 is a schematic diagram, and the thickness relationship and positional relationship of each layer do not always match the actual ones, and the support, alignment film, and hardcoat 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 the 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.
  • thermoplastic norbornene polymers polycarbonate polymers; polyester polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene polymers such as polystyrene and acrylonitrile / styrene copolymers (AS resin); polyethylene, polypropylene, ethylene / propylene Polyolefin-based polymers such as polymers; Vinyl chloride-based polymers; Amido-based polymers such as nylon and aromatic polyamides; Imid-based polymers; Examples thereof include vinylidene chloride-based polymers; vinyl alcohol-based polymers; vinyl butyral-based polymers; allylate-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; or polymers in which these polymers are mixed. Further, the stator described later may also serve as such a support.
  • 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 is generally composed of 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, and its derivatives. Particularly modified or unmodified polyvinyl alcohol is preferable.
  • the alignment film that can be used in the present invention for example, the alignment film described in International Publication No. 01/88574, page 43, lines 24 to 49, line 8; paragraphs [0071] to [00905] of Patent No. 3907735.
  • 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 the alignment film is formed.
  • 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 Technologies, etc. 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 hardcoat layer in order to impart physical strength to the film.
  • the hardcourt 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 hardcourt layer on the opposite side (see FIG. 1C).
  • the hard coat layer those described in paragraphs [0190] to [0196] of JP-A-2009-98658 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 a rod-shaped type and a disk-shaped type according to their shapes.
  • a polymer generally refers to a molecule 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). 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 For the immobilization of the above-mentioned liquid crystal compound, it is more preferable to form a rod-shaped liquid crystal compound having a polymerizable group or a disk-shaped liquid crystal compound, and the liquid crystal compound may have two or more polymerizable groups in one molecule. More preferred. When 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 No. 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 JP-A-2007-108732 and paragraphs [0013] to [0108] of JP-A-2010-244038 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 light).
  • 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 agent 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 the compounds described in paragraphs [0258] to [0259] of JP2012-18395, paragraphs [0055] to [0105] of JP2007-72163. Examples thereof include the compounds described in.
  • Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, Tinuvin 1577 (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 polarizing element. Further, the polarizing plate of the present invention can be used as a circular polarizing plate when the optically anisotropic film of the present invention described above is a ⁇ / 4 plate (positive A plate). Further, in the polarizing plate of the present invention, when the above-mentioned optically anisotropic film of the present invention is a ⁇ / 4 plate (positive A plate), the slow axis of the ⁇ / 4 plate and the absorption axis of the substituent described later are used.
  • 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 substituent means the direction in which the absorbance is highest. do.
  • the polarizing plate 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 a specific linear polarization, and conventionally known absorption-type and reflection-type splitters can be used. ..
  • As the absorption type polarizing element an iodine-based polarizing element, a dye-based polarizing element using a dichroic dye, a polyene-based polarizing element, and the like are used.
  • Iodine-based splitters and dye-based splitters include coated and stretched splitters, both of which can be applied, but polarized light produced by adsorbing iodine or a dichroic dye on polyvinyl alcohol and stretching it.
  • Japanese Patent No. 5048120 Japanese Patent No. 5143918, Japanese Patent No. 4691205, and Patent No. 5048120
  • Patent No. Japanese Patent No. 4751481 and Japanese Patent No. 4751486 can be mentioned, and known techniques for these substituents can also be preferably used.
  • the reflective classifier a splitter in which thin films having different birefringences are laminated, a wire grid type splitter, a carboxylator in which a cholesteric liquid crystal having a selective reflection region and a 1/4 wave plate are combined, and the like are used.
  • At least one selected from the group consisting of a polyvinyl alcohol-based resin (a polymer containing -CH2 -CHOH- as a repeating unit, particularly a polyvinyl alcohol and an ethylene-vinyl alcohol copolymer) in that the adhesion is more excellent. It is preferable that the polymer contains one).
  • the thickness of the polarizing element 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 polarizing element.
  • 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, polyvinyl alcohol-based pressure-sensitive adhesives.
  • 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 Alignment) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, an FFS (Fringe-Field-Switching) mode, or a TN (Tw) mode.
  • VA Vertical Alignment
  • OCB Optically Compensated Bend
  • IPS In-Plane-Switching
  • FFS Feringe-Field-Switching
  • TN Tw
  • 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 (1) 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-).
  • a liquid crystal cell SID97, Digital of technique. Papers (Proceedings) 28 (1997) 845 in which the VA mode is multi-domainized for expanding the viewing angle).
  • 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-Stained 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.
  • the organic EL display device which is an example of the image display device of the present invention, includes, for example, a ⁇ / 4 plate (positive A plate) made of a polarizing element, an optically anisotropic film of the present invention, and an organic EL from the viewing side.
  • a mode having a display panel 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.
  • the compound (2-1-c) and the compound (2-1-d) used in the synthesis of the specific compound (2-1) are the compound (2--2-a) and the compound (2-2) shown in the above scheme.
  • the specific compound (2-2) was obtained by the same method as the synthesis of the specific compound (2-1) except that it was changed to ⁇ b).
  • the 1 H-NMR data of the obtained specific compound (2-2) is shown below.
  • 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 Industry Co., Ltd.) by spin coating.
  • the coating film was oriented at the temperatures shown in Table 1 below to form a liquid crystal layer.
  • the film was cooled to the exposure temperature shown in Table 1 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 produced.
  • Example 2 to 6 An optical film was produced in the same manner as in Example 1 except that the reverse wavelength dispersible liquid crystal compound or the specific compound was changed to the compound shown in Table 1 below.
  • the specific compound among the ring structures represented by M in the above formula (II), the maximum absorption wavelength of the aromatic ring represented by the central M is also shown in Table 1 below.
  • Example 1 An optical film was produced by the same method as in Example 1 except that the blending amount of the reverse wavelength dispersible liquid crystal compound was changed to the mass part shown in Table 1 below and the specific compound was not blended.
  • B 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.
  • ⁇ Orientation defect> The obtained optical film was cut into 10 cm squares, and the number of alignment defects on the screen was visually confirmed using a polarizing microscope (LEXT, manufactured by Olympus Corporation) and evaluated according to the following evaluation criteria. The results are shown in Table 1 below. (Evaluation criteria for orientation defects) A: No defects B: 1 to 10 C: 11 to 100 D: Orientation defects occur on the entire surface (> 100)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Mathematical Physics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polarising Elements (AREA)
  • Devices For Indicating Variable Information By Combining Individual Elements (AREA)
  • Liquid Crystal (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention aborde le problème consistant à fournir : une composition de cristaux liquides capable de supprimer l'apparition de défauts d'orientation dans un film optiquement anisotrope ; un composé ; un film optiquement anisotrope ; un film optique ; une plaque de polarisation ; et un dispositif d'affichage d'image. Une composition de cristaux liquides selon la présente invention contient un composé cristal liquide, et un composé représenté par la formule (II).
PCT/JP2021/031726 2020-09-18 2021-08-30 Composition de cristaux liquides, composé, film optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image Ceased WO2022059470A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2022550441A JP7538237B2 (ja) 2020-09-18 2021-08-30 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
KR1020237008575A KR102851512B1 (ko) 2020-09-18 2021-08-30 액정 조성물, 화합물, 광학 이방성막, 광학 필름, 편광판 및 화상 표시 장치
CN202180063766.2A CN116249757B (zh) 2020-09-18 2021-08-30 液晶组合物、化合物、光学各向异性膜、光学膜、偏振片及图像显示装置

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020-157416 2020-09-18
JP2020157416 2020-09-18

Publications (1)

Publication Number Publication Date
WO2022059470A1 true WO2022059470A1 (fr) 2022-03-24

Family

ID=80776163

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/031726 Ceased WO2022059470A1 (fr) 2020-09-18 2021-08-30 Composition de cristaux liquides, composé, film optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image

Country Status (4)

Country Link
JP (1) JP7538237B2 (fr)
KR (1) KR102851512B1 (fr)
CN (1) CN116249757B (fr)
WO (1) WO2022059470A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025070147A1 (fr) * 2023-09-29 2025-04-03 富士フイルム株式会社 Film durci, film optique et dispositif d'affichage d'image

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005002111A (ja) * 2003-05-27 2005-01-06 Samsung Electronics Co Ltd ベンゾフェノン系誘導体，耐光性インク組成物
JP2006233098A (ja) * 2005-02-25 2006-09-07 Fuji Photo Film Co Ltd セルロース誘導体組成物、セルロース誘導体フイルム、およびアルコキシ安息香酸誘導体化合物
JP2012207073A (ja) * 2011-03-29 2012-10-25 Fujifilm Corp 高分子フィルム用添加剤、高分子フィルム、位相差フィルム、偏光板、液晶表示装置、及びオリゴマー
WO2013089077A1 (fr) * 2011-12-16 2013-06-20 コニカミノルタ株式会社 Film optique, plaque polarisante l'utilisant, et dispositif d'affichage à cristaux liquides
JP2015194697A (ja) * 2014-03-24 2015-11-05 Jsr株式会社 液晶配向剤、液晶配向膜及びその製造方法、液晶表示素子、位相差フィルム及びその製造方法、重合体並びに化合物
WO2015198915A1 (fr) * 2014-06-23 2015-12-30 Dic株式会社 Composition de cristaux liquides polymérisable ainsi que corps optiquement anisotrope fabriqué à l'aide de celle-ci, film de déphasage, et film de production de motif de déphasage
WO2016129490A1 (fr) * 2015-02-09 2016-08-18 Jnc株式会社 Composé polaire polymérisable, composition de cristaux liquides, et élément d'affichage à cristaux liquides
WO2018025974A1 (fr) * 2016-08-03 2018-02-08 Jnc株式会社 Élément d'affichage et dispositif d'affichage à cristaux liquides
WO2019220673A1 (fr) * 2018-05-15 2019-11-21 Jnc株式会社 Composé, composition de cristaux liquides, et élément d'affichage à cristaux liquides
WO2020022429A1 (fr) * 2018-07-25 2020-01-30 富士フイルム株式会社 Composition de cristaux liquides, film optiquement anisotrope, film optique, plaque polarisante et dispositif d'affichage d'image
WO2020022422A1 (fr) * 2018-07-25 2020-01-30 富士フイルム株式会社 Composition de cristaux liquides polymérisable, film optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image
JP2020147749A (ja) * 2019-03-05 2020-09-17 富士フイルム株式会社 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102233332B1 (ko) * 2017-02-21 2021-03-26 후지필름 가부시키가이샤 중합성 액정 화합물, 중합성 액정 화합물의 제조 방법, 중합성 액정 조성물, 광학 이방성막, 광학 필름, 편광판 및 화상 표시 장치
CN110891945B (zh) * 2017-07-19 2023-01-24 富士胶片株式会社 聚合性液晶化合物、聚合性液晶组合物、光学各向异性膜、光学膜、偏振片及图像显示装置
KR102307920B1 (ko) * 2017-07-19 2021-09-30 후지필름 가부시키가이샤 중합성 액정 화합물, 중합성 액정 조성물, 광학 이방성막, 광학 필름, 편광판 및 화상 표시 장치
WO2019131976A1 (fr) * 2017-12-28 2019-07-04 富士フイルム株式会社 Film anisotrope absorbant la lumière, produit stratifié optique et dispositif d'affichage d'image

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005002111A (ja) * 2003-05-27 2005-01-06 Samsung Electronics Co Ltd ベンゾフェノン系誘導体，耐光性インク組成物
JP2006233098A (ja) * 2005-02-25 2006-09-07 Fuji Photo Film Co Ltd セルロース誘導体組成物、セルロース誘導体フイルム、およびアルコキシ安息香酸誘導体化合物
JP2012207073A (ja) * 2011-03-29 2012-10-25 Fujifilm Corp 高分子フィルム用添加剤、高分子フィルム、位相差フィルム、偏光板、液晶表示装置、及びオリゴマー
WO2013089077A1 (fr) * 2011-12-16 2013-06-20 コニカミノルタ株式会社 Film optique, plaque polarisante l'utilisant, et dispositif d'affichage à cristaux liquides
JP2015194697A (ja) * 2014-03-24 2015-11-05 Jsr株式会社 液晶配向剤、液晶配向膜及びその製造方法、液晶表示素子、位相差フィルム及びその製造方法、重合体並びに化合物
WO2015198915A1 (fr) * 2014-06-23 2015-12-30 Dic株式会社 Composition de cristaux liquides polymérisable ainsi que corps optiquement anisotrope fabriqué à l'aide de celle-ci, film de déphasage, et film de production de motif de déphasage
WO2016129490A1 (fr) * 2015-02-09 2016-08-18 Jnc株式会社 Composé polaire polymérisable, composition de cristaux liquides, et élément d'affichage à cristaux liquides
WO2018025974A1 (fr) * 2016-08-03 2018-02-08 Jnc株式会社 Élément d'affichage et dispositif d'affichage à cristaux liquides
WO2019220673A1 (fr) * 2018-05-15 2019-11-21 Jnc株式会社 Composé, composition de cristaux liquides, et élément d'affichage à cristaux liquides
WO2020022429A1 (fr) * 2018-07-25 2020-01-30 富士フイルム株式会社 Composition de cristaux liquides, film optiquement anisotrope, film optique, plaque polarisante et dispositif d'affichage d'image
WO2020022422A1 (fr) * 2018-07-25 2020-01-30 富士フイルム株式会社 Composition de cristaux liquides polymérisable, film optiquement anisotrope, film optique, plaque de polarisation et dispositif d'affichage d'image
JP2020147749A (ja) * 2019-03-05 2020-09-17 富士フイルム株式会社 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025070147A1 (fr) * 2023-09-29 2025-04-03 富士フイルム株式会社 Film durci, film optique et dispositif d'affichage d'image

Also Published As

Publication number Publication date
JP7538237B2 (ja) 2024-08-21
CN116249757B (zh) 2025-06-17
JPWO2022059470A1 (fr) 2022-03-24
KR102851512B1 (ko) 2025-08-28
CN116249757A (zh) 2023-06-09
KR20230051243A (ko) 2023-04-17

Similar Documents

Publication Publication Date Title
JP7500813B2 (ja) 重合性液晶組成物、重合性液晶組成物の製造方法、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP7033223B2 (ja) 重合性液晶化合物、重合性液晶化合物の製造方法、重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
WO2021060432A1 (fr) Composition de cristaux liquides, couche optiquement anisotrope, film optique, plaque polarisante et dispositif d'affichage d'image
WO2021060427A1 (fr) Composition de cristaux liquides polymérisable, produit durci, film optique, plaque de polarisation et dispositif d'affichage d'image
JP6823011B2 (ja) 重合性化合物、重合性化合物の製造方法、重合性組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP7118153B2 (ja) 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
CN114450330B (zh) 光学各向异性层、光学膜、偏振片、图像显示装置
JP7340617B2 (ja) 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
JP7523281B2 (ja) 重合体、重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP7285226B2 (ja) 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
JP7335856B2 (ja) 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP7538237B2 (ja) 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
JP7371110B2 (ja) 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP7285227B2 (ja) 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
JP6975308B2 (ja) 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP6944582B2 (ja) 混晶、重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP6910527B2 (ja) 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP7440647B2 (ja) 液晶組成物、液晶硬化層、光学フィルム、偏光板および画像表示装置
JP7012622B2 (ja) 化合物、組成物、硬化物、光学フィルム、偏光板および画像表示装置
JP7042761B2 (ja) 重合性液晶組成物、光学異方性膜、光学フィルム、偏光板および画像表示装置
JP7291651B2 (ja) 順波長分散性液晶化合物、重合性液晶組成物、硬化物、光学フィルム、偏光板および画像表示装置
WO2024176869A1 (fr) Composition de cristaux liquides polymérisable, film optiquement anisotrope, film optique, plaque de polarisation, dispositif d'affichage d'image et procédé de production d'une composition de cristaux liquides polymérisable

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21869157

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2022550441

Country of ref document: JP

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 20237008575

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21869157

Country of ref document: EP

Kind code of ref document: A1

WWG Wipo information: grant in national office

Ref document number: 202180063766.2

Country of ref document: CN