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  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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  • 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
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  • G02B5/00—Optical elements other than lenses
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  • 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
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  • C09K2219/00—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used
  • C09K2219/11—Aspects relating to the form of the liquid crystal [LC] material, or by the technical area in which LC material are used used in the High Frequency technical field

Definitions

• the present invention relates to a liquid crystal composition, a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device.
• Optical films such as optical compensation sheets and retardation films are used in various image display devices to eliminate image coloration or expand the viewing angle.
• Stretched birefringent films have been used as optical films, but in recent years, it has been proposed to use optical films having an optically anisotropic layer made of a liquid crystal compound in place of stretched birefringent films.
• an optical film formed using a liquid crystal composition containing a compound represented by a specific formula and a liquid crystal compound is known (see, for example, Patent Document 1).
• the present invention aims to provide a liquid crystal composition, a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device that can produce a liquid crystal cured layer that has both good alignment and light resistance.
• a liquid crystal cured layer having both good alignment properties and good light resistance can be prepared by using a liquid crystal composition containing a compound represented by formula (A) and a liquid crystal compound, and have completed the present invention. That is, the present inventors have found that the above problems can be solved by the following configuration.
• a liquid crystal composition containing a compound represented by formula (A) described later and a liquid crystal compound [2] The liquid crystal composition according to [1], wherein the liquid crystal compound is a compound represented by formula (B) described later. [3] The liquid crystal composition according to [1] or [2], wherein the content of the compound represented by formula (A) described later is 18 mass % or less based on the total mass of the compound represented by formula (A) described later and the liquid crystal compound. [4] The liquid crystal composition according to any one of [1] to [3], wherein Ar 1 in formula (A) described later is an aromatic ring represented by formula (BQ-1) or (BQ-2) described later.
• the present invention provides a liquid crystal composition, a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device that can produce a liquid crystal cured layer that has both good alignment and light resistance.
• FIG. 1 is a schematic cross-sectional view showing an example of an optical film.
• a numerical range expressed using "to” means a range that includes the numerical values before and after "to" as the lower and upper limits.
• the upper or lower limit value of a certain numerical range in a stepwise described numerical range may be replaced with the upper or lower limit value of another stepwise described numerical range.
• the upper or lower limit value of a certain numerical range in the present specification may be replaced with a value shown in the examples.
• each component may be used alone or in combination of two or more substances corresponding to each component.
• the content of the component refers to the total content of the substances used in combination, unless otherwise specified.
• “(meth)acrylate” is a notation representing “acrylate” or “methacrylate”
• “(meth)acrylic” is a notation representing “acrylic” or “methacrylic”
• “(meth)acryloyl” is a notation representing "acryloyl” or “methacryloyl”.
• the bonding direction of a divalent group (e.g., -O-CO-) represented in this specification is not particularly limited.
• L2 when L2 is -O-CO- in the bond of " L1 - L2 - L3 ", when the position bonded to L1 side is *1 and the position bonded to L3 side is *2, L2 may be *1-O-CO-*2 or *1-CO-O-*2.
• Re( ⁇ ) and Rth( ⁇ ) respectively represent the in-plane retardation and the retardation in the thickness direction at a wavelength ⁇ , which is set to 550 nm unless otherwise specified.
• Re( ⁇ ) and Rth( ⁇ ) are values measured at a wavelength ⁇ using an AxoScan (manufactured by Axometrics).
• AxoScan manufactured by Axometrics.
• Re( ⁇ ) R0( ⁇ )
• examples of the substituent include the substituents described in the following Substituent Group A.
• the phrase "optionally substituted” includes embodiments having one or more substituents as well as embodiments having no substituents.
• substituents include: A halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, preferably a chlorine atom, a fluorine atom, more preferably a fluorine atom); Alkyl groups (preferably linear, branched or cyclic alkyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as linear alkyl groups having 1 to 6 carbon atoms (e.g., methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl), branched alkyl groups having 3 to 6 carbon atoms (e.g., isopropyl, isobutyl, tert-butyl, sec-butyl, neopentyl, isohexyl, 3-methylpenty
• a halogen atom e.
• the liquid crystal composition of the present invention contains a compound represented by formula (A) described below (hereinafter also abbreviated as "specific compound A”) and a liquid crystal compound.
• a liquid crystal cured layer having good alignment properties and light resistance can be prepared.
• the specific compound A has a specific aromatic ring, and therefore has good compatibility with the liquid crystal compound, and can maintain excellent alignment of the liquid crystal compound.
• the specific compound A is a quinone compound, it is affected by ultraviolet light earlier than the liquid crystal compound, and can also function as an ultraviolet absorber, and therefore the light resistance of the produced liquid crystal cured layer is considered to be good.
• the specific compound A and the liquid crystal compound contained in the liquid crystal composition of the present invention will be described in detail below.
• the specific compound A is a compound represented by the following formula (A).
• Ar 1 represents any aromatic ring selected from the group consisting of groups represented by the following formulae (BQ-1) to (BQ-5): In the following formulae (BQ-1) to (BQ-5), * represents the bonding position with the oxygen atom in the above formula (A).
• Q1 represents N or CH
• Q2 represents -S-, -O-, or -N( R6 )-
• R6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
• Y1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and one or more of the -CH2- constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-.
• alkyl group having 1 to 6 carbon atoms represented by one embodiment of R 6 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.
• aromatic hydrocarbon group having 6 to 12 carbon atoms represented by one embodiment of Y1 include aryl groups such as a phenyl group, a 2,6-diethylphenyl group, and a naphthyl group.
• Examples of the aromatic heterocyclic group having 3 to 12 carbon atoms represented by one embodiment of Y 1 include heteroaryl groups such as a thienyl group, a thiazolyl group, a furyl group, and a pyridyl group, as well as groups obtained by removing one hydrogen atom from any of an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzothiazole ring, and a benzoxazole ring.
• heteroaryl groups such as a thienyl group, a thiazolyl group, a furyl group, and a pyridyl group, as well as groups obtained by removing one hydrogen atom from any of an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzothiazole ring, and a benzox
• the aromatic heterocyclic group having 3 to 12 carbon atoms represented by Y 1 is preferably a group obtained by removing one hydrogen atom from a benzofuran ring or a benzothiazole ring.
• Examples of the alicyclic hydrocarbon group having 6 to 20 carbon atoms represented by one embodiment of Y 1 include a cyclohexylene group, a cyclopentylene group, a norbornylene group, and an adamantylene group.
• Examples of the substituent that Y1 may have include the substituents described in the above-mentioned Substituent Group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a nitro group, a cyano group, or a halogen atom is preferable.
• Z 1 , Z 2 and Z 3 each independently represent a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 or -COR 12 , R 7 to R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 may be bonded to each other to form an aromatic ring.
• an alkyl group having 1 to 15 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, specifically, a methyl group, an ethyl group, an isopropyl group, a tert-pentyl group (1,1-dimethylpropyl group), a tert-butyl group, or a 1,1-dimethyl-3,3-dimethyl-butyl group is further preferable, and a methyl group, an ethyl group, or a tert-butyl group is particularly preferable.
• Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include monocyclic saturated hydrocarbon groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, a methylcyclohexyl group, and an ethylcyclohexyl group; monocyclic unsaturated hydrocarbon groups such as a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, a cyclodecenyl group, a cyclopentadienyl group, a cyclohexadienyl group, a cyclooctadienyl group,
• the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, and a biphenyl group, and an aryl group having 6 to 12 carbon atoms (particularly a phenyl group) is preferred.
• Specific examples of the monovalent aromatic heterocyclic group having 6 to 20 carbon atoms include a 4-pyridyl group, a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group.
• halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among these, a fluorine atom, a chlorine atom, and a bromine atom are preferred.
• specific examples of the alkyl group having 1 to 6 carbon atoms represented by R 7 to R 10 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.
• Z1 and Z2 may be bonded to each other to form an aromatic ring
• an example of a structure in which Z1 and Z2 in the above formula (BQ-1) are bonded to each other to form an aromatic ring is a group represented by the following formula (BQ-1a).
• * represents the bonding position with the oxygen atom in the above formula (A).
• Q 1 , Q 2 and Y 1 are the same as those explained in the above formula (BQ-1).
• A3 and A4 each independently represent a group selected from the group consisting of -O-, -N( R13 )-, -S-, and -CO-, and R13 represents a hydrogen atom or a substituent.
• R 13 represents a hydrogen atom or a substituent.
• substituents represented by one embodiment of R 13 include the substituents described in the above-mentioned Substituent Group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
• X represents a nonmetallic atom of Groups 14 to 16.
• the nonmetallic atom may have a hydrogen atom or a substituent bonded thereto.
• Examples of the non-metallic atom of Groups 14 to 16 represented by X include an oxygen atom, a sulfur atom, a nitrogen atom bonded to a hydrogen atom or a substituent [ ⁇ N—R N1 , R N1 represents a hydrogen atom or a substituent], and a carbon atom bonded to a hydrogen atom or a substituent [ ⁇ C—(R C1 ) 2 , R C1 represents a hydrogen atom or a substituent].
• substituents described in the above-mentioned substituent group A include the substituents described in the above-mentioned substituent group A.
• preferred examples include an alkyl group, an alkoxy group, an alkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (for example, a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, an alkylcarbonyl group, a sulfo group, and a hydroxyl group.
• R 1 , R 2 and R 5 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. Among these, any one of --CO--, --O-- and --CO--O-- is preferable.
• SP 3 and SP 4 each independently represent a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms.
• one or more of the -CH 2 - constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-.
• Q represents a substituent.
• the substituent represented by Q include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
• Examples of the divalent aliphatic hydrocarbon group include linear or branched alkylene groups having 1 to 20 carbon atoms, linear or branched alkenylene groups having 1 to 20 carbon atoms, and linear or branched alkynylene groups having 1 to 20 carbon atoms.
• As the linear or branched alkylene group having 1 to 20 carbon atoms an alkylene group having 1 to 12 carbon atoms is preferable, and an alkylene group having 1 to 10 carbon atoms is more preferable.
• Suitable examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group.
• linear or branched alkenylene group having 1 to 20 carbon atoms an alkenylene group having 2 to 10 carbon atoms is preferable, and an alkenylene group having 2 to 4 carbon atoms is more preferable, and a suitable example thereof is an ethenylene group.
• an alkynylene group having 2 to 10 carbon atoms is preferable, and an alkynylene group having 2 to 4 carbon atoms is more preferable, and a suitable example thereof is an ethynylene group.
• L3 and L4 each independently represent a monovalent organic group.
• the monovalent organic group include the substituents described in the above-mentioned Substituent group A, and among them, preferred examples include an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a cyano group, and a carboxy group.
• the alkyl group may be linear, branched or cyclic, but is preferably linear.
• the number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 10.
• the aryl group may be either a monocyclic or polycyclic group, but is preferably a monocyclic group.
• the aryl group preferably has 6 to 25 carbon atoms, and more preferably has 6 to 10 carbon atoms.
• the heteroaryl group may be a monocyclic or polycyclic ring.
• the number of heteroatoms constituting the heteroaryl group is preferably 1 to 3.
• the heteroatoms constituting the heteroaryl group are preferably a nitrogen atom, a sulfur atom, or an oxygen atom.
• the number of carbon atoms in the heteroaryl group is preferably 6 to 18, and more preferably 6 to 12.
• the alkyl group, the aryl group and the heteroaryl group may be unsubstituted or may have a substituent.
• substituents examples include those described in the above-mentioned Substituent Group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
• At least one of L 3 and L 4 may be a polymerizable group.
• the polymerizable group is not particularly limited, but is preferably a polymerizable group capable of radical polymerization or cationic polymerization.
• the radical polymerizable group a known radical polymerizable group can be used, and a suitable one can be an acryloyloxy group or a methacryloyloxy group. In this case, it is known that the polymerization rate of the acryloyloxy group is generally fast, and from the viewpoint of improving productivity, the acryloyloxy group is preferred, but the methacryloyloxy group can also be used as the polymerizable group.
• a known cationic polymerizable group can be used, and specific examples thereof include an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiro orthoester group, and a vinyloxy group.
• an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is particularly preferable.
• Particularly preferred examples of the polymerizable group include those represented by any of the following formulae (P-1) to (P-20).
• Q3 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 6 carbon atoms.
• Ax and Ay include those described in paragraphs [0039] to [0095] of WO 2014/010325.
• Specific examples of the alkyl group having 1 to 6 carbon atoms represented by Q3 include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.
• substituents described in the above-mentioned Substituent group A examples include the substituents described in the above-mentioned Substituent group A. Among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
• Ar 1 in the above formula (A) is preferably an aromatic ring represented by the above formula (BQ-1) or (BQ-2).
• Suitable examples of the specific compound A include specific compounds (A-1) to (A-12) represented by the following formulae:
• liquid crystal compound contained in the liquid crystal composition of the present invention is not particularly limited, and any conventionally known liquid crystal compound can be used.
• liquid crystal compounds can be classified into rod-shaped and disk-shaped types based on their shape. Each type can be further divided into low molecular weight and high molecular weight types.
• High molecular weight generally refers to a compound with a degree of polymerization of 100 or more (Polymer Physics: Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992).
• 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 (discotic liquid crystal compound).
• rod-shaped liquid crystal compounds Two or more rod-shaped liquid crystal compounds, two or more discotic liquid crystal compounds, or a mixture of a rod-shaped liquid crystal compound and a discotic liquid crystal compound may also be used.
• the rod-shaped liquid crystal compound for example, those described in claim 1 of JP-T-11-513019 and paragraphs [0026] to [0098] of JP-A-2005-289980 can be preferably used
• the discotic 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, but are not limited thereto.
• the liquid crystal compound preferably has a polymerizable group, more preferably has two or more polymerizable groups, for the reason that the durability of the cured liquid crystal layer is improved.
• Suitable examples of the polymerizable group include those represented by any of the above formulas (P-1) to (P-20).
• the liquid crystal compound is preferably a compound represented by the following formula (B) because the alignment property of the cured liquid crystal layer is improved.
• a1, a2, g1, and g2 each independently represent 0 or 1, provided that at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1.
• D 1 , D 2 , D 3 , D 4 , D 5 and D 6 each independently represent a single bond, -CO-, -O-, -S-, -C( ⁇ S)-, -CR 1 R 2 -, -CR 3 ⁇ CR 4 -, -NR 5 -, or a divalent linking group consisting of a combination of two or more of these, and R 1 to R 5 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.
• G1 and G2 each independently represent an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have a substituent, and one or more of the -CH2- constituting the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-.
• A1 and A2 each independently represent an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have a substituent, and one or more of the -CH2- constituting the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-.
• SP 1 and SP 2 each independently represent a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that one or more of the -CH 2 - groups constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-.
• L1 and L2 each independently represent a monovalent organic group, and at least one of L1 and L2 represents a polymerizable group, provided that when Ar2 is an aromatic ring represented by the following formula (Ar-3), at least one of L1 and L2 and L3 and L4 in the following formula (Ar- 3 ) represents a polymerizable group.
• Ar2 represents any aromatic ring selected from the group consisting of groups represented by formulas (Ar-1) to (Ar-7) described later.
• a1, a2, g1 and g2 are all preferably 1 because this makes the liquid crystal composition of the present invention more likely to exhibit a smectic liquid crystal state.
• a1 and a2 are both 0 and g1 and g2 are both 1, because this improves the durability of the produced cured liquid crystal layer.
• examples of the divalent linking group represented by one embodiment of D 1 , D 2 , D 3 , D 4 , D 5 and D 6 include the same as those described in the above formula (BQ-3) represented by one embodiment of Ar 1 in the above formula (A) as D 7 and D 8 .
• examples of the aromatic ring having 6 to 20 carbon atoms represented by one embodiment of G1 and G2 include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring, and aromatic heterocycles such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring.
• 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.
• a benzene ring for example,
• the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one embodiment of G 1 and G 2 is preferably a 5-membered or 6-membered ring.
• the alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a saturated alicyclic hydrocarbon group.
• the description in paragraph [0078] of JP 2012-21068 A can be referred to, and the contents of this document are incorporated herein by reference.
• G 1 and G 2 in the above formula (B) are preferably cycloalkane rings, because the durability of the produced cured liquid crystal layer is improved.
• the cycloalkane ring include a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclododecane ring, and a cyclodocosane ring.
• a cyclohexane ring is preferred, a 1,4-cyclohexylene group is more preferred, and a trans-1,4-cyclohexylene group is even more preferred.
• examples of the substituent that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms may have include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.
• examples of the aromatic ring having 6 to 20 carbon atoms represented by one embodiment of A 1 and A 2 include the same as those explained in relation to G 1 and G 2 in the above formula (B).
• examples of the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one embodiment of A1 and A2 include the same groups as those described for G1 and G2 in the above formula (B).
• examples of the substituent that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms may have include the same as the substituents that G1 and G2 in the above formula (B) may have.
• examples of the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by one embodiment of SP 1 and SP 2 include linear or branched alkylene groups having 1 to 20 carbon atoms, linear or branched alkenylene groups having 1 to 20 carbon atoms, and linear or branched alkynylene groups having 1 to 20 carbon atoms.
• linear or branched alkylene group having 1 to 20 carbon atoms an alkylene group having 1 to 12 carbon atoms is preferable, and an alkylene group having 1 to 10 carbon atoms is more preferable.
• Suitable examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group.
• a linear or branched alkenylene group having 1 to 20 carbon atoms an alkenylene group having 2 to 10 carbon atoms is preferable, and an alkenylene group having 2 to 4 carbon atoms is more preferable, and a suitable example thereof is an ethenylene group.
• linear or branched alkynylene group having 1 to 20 carbon atoms an alkynylene group having 2 to 10 carbon atoms is preferable, and an alkynylene group having 2 to 4 carbon atoms is more preferable, and a suitable example thereof is an ethynylene group.
• one or more of the -CH 2 - groups constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-.
• Examples of the substituent represented by Q include the substituents described in the above-mentioned substituent group A, and among these, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group or a halogen atom is preferable.
• examples of the monovalent organic groups represented by L1 and L2 include the same as those described for L3 and L4 in the above formula (BQ-3) represented by one embodiment of Ar1 in the above formula (A).
• the polymerizable group represented by at least one of L 1 and L 2 the polymerizable group represented by any one of the above formulae (P-1) to (P-20) is preferably mentioned.
• Ar2 represents any aromatic ring selected from the group consisting of groups represented by the following formulae (Ar-1) to (Ar-7), as described above.
• formulae (Ar-1) to (Ar-7) * represents the bonding position with D1 or D2 in the above formula (B).
• each symbol in the above formulae (Ar-1) to (Ar-7) is the same as each symbol in the above formulae (BQ-1) to (BQ-5) represented by Ar 1 in the above formula (A).
• liquid crystal compound examples include the compounds represented by general formula (1) described in JP 2010-084032 A (particularly, the compounds described in paragraphs [0067] to [0073]), the compounds represented by general formula (II) described in JP 2016-053709 A (particularly, the compounds described in paragraphs [0036] to [0043]), and the compounds represented by general formula (1) described in JP 2016-081035 A (particularly, the compounds described in paragraphs [0043] to [0055]), and the compounds described in paragraphs [0025] to [0056] of WO 2021/060427 A.
• liquid crystal compounds include the liquid crystal compounds (B-1) to (B-14) represented by the following formulas:
• the content of the compound represented by the above formula (A) is preferably 18% by mass or less, and more preferably 5 to 18% by mass, based on the total mass of the compound represented by the above formula (A) and the above liquid crystal compound (particularly the compound represented by the above formula (B)), in order to obtain better alignment of the liquid crystal cured layer.
• Ar 1 in the above formula (A) and Ar 2 in the above formula (B) have the same structure.
• the liquid crystal composition of the present invention preferably contains, in addition to the specific compound A and the liquid crystal compound described above, another polymerizable compound having one or more polymerizable groups.
• the polymerizable group possessed by the other polymerizable compound is not particularly limited, and suitable examples thereof include the polymerizable groups represented by any of the above-mentioned formulae (P-1) to (P-20).
• the other polymerizable compound is preferably another polymerizable compound having 2 to 4 polymerizable groups, and more preferably another polymerizable compound having 2 polymerizable groups, because this further improves the durability of the liquid crystal cured layer that is formed.
• Such other polymerizable compounds include compounds represented by formulas (M1), (M2), and (M3) described in paragraphs [0030] to [0033] of JP2014-077068A, and more specifically, specific examples described in paragraphs [0046] to [0055] of the same publication.
• 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 light.
• Examples of the photopolymerization initiator include ⁇ -carbonyl compounds (described in U.S. Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (described in U.S. Pat. No. 2,448,828), ⁇ -hydrocarbon-substituted aromatic acyloin compounds (described in U.S. Pat. No. 2,722,512), polynuclear quinone compounds (described in U.S. Pat.
• the polymerization initiator is also preferably an oxime-type polymerization initiator, and specific examples thereof include the initiators described in paragraphs [0049] to [0052] of WO 2017/170443.
• the liquid crystal composition of the present invention preferably contains a solvent from the viewpoint of workability in forming a cured liquid crystal layer.
• the solvent include ketones (e.g., acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, etc.), ethers (e.g., dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g., hexane, etc.), alicyclic hydrocarbons (e.g., cyclohexane, etc.), aromatic hydrocarbons (e.g., toluene, xylene, trimethylbenzene, etc.), halogenated carbons (e.g., dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.), esters (e.g., methyl
• the liquid crystal composition of the present invention preferably contains a leveling agent from the viewpoint of facilitating alignment control.
• a leveling agent a fluorine-based leveling agent or a silicon-based leveling agent is preferable because it has a high leveling effect relative to the amount added, and a fluorine-based leveling agent is more preferable because it is less likely to cause bleeding (bloom, bleed).
• leveling agent examples include compounds described in JP-A-2007-069471, paragraphs [0079] to [0102], compounds represented by general formula (I) described in JP-A-2013-047204 (particularly, compounds described in paragraphs [0020] to [0032]), and compounds represented by general formula (I) described in JP-A-2012-211306 (particularly, compounds represented by paragraphs [0022] to [0029]).
• Examples of the compound include compounds described in the paragraphs 2002-129162, liquid crystal alignment promoters represented by general formula (I) described in JP-A-2002-129162 (particularly compounds described in paragraphs [0076] to [0078] and [0082] to [0084]), and compounds represented by general formulas (I), (II) and (III) described in JP-A-2005-099248 (particularly compounds described in paragraphs [0092] to [0096]).
• the compound may also function as an alignment control agent, which will be described later.
• the liquid crystal composition of the present invention may contain an alignment control agent, if necessary.
• the alignment control agent can form various alignment states, such as homogeneous alignment, homeotropic alignment (vertical alignment), tilted alignment, hybrid alignment, and cholesteric alignment, and can also realize specific alignment states more uniformly and with more precise control.
• a low molecular weight alignment control agent or a polymeric alignment control agent can be used.
• low molecular weight orientation control agents reference can be made to, for example, paragraphs [0009] to [0083] of JP 2002-20363 A, paragraphs [0111] to [0120] of JP 2006-106662 A, and paragraphs [0021] to [0029] of JP 2012-211306 A, the contents of which are incorporated herein by reference.
• the compounds described in JP2008-225281A, paragraphs [0023] to [0032], JP2012-208397A, paragraphs [0052] to [0058], JP2008-026730A, paragraphs [0024] to [0055], and JP2016-193869A, paragraphs [0043] to [0055], etc. can be referred to, the contents of which are incorporated herein by reference.
• cholesteric alignment can be realized by adding a chiral agent to the polymerizable liquid crystal composition of the present invention, and the direction of rotation of the cholesteric alignment can be controlled by the direction of the chirality.
• the pitch of the cholesteric alignment can be controlled according to the alignment control force of the chiral agent.
• an orientation control agent When an orientation control agent is included, its content is preferably 0.01 to 10 mass % relative to the total solid mass in the composition, and more preferably 0.05 to 5 mass %. When the content is within this range, it is possible to obtain a uniform and highly transparent cured product without precipitation, phase separation, orientation defects, etc., while achieving the desired orientation state.
• the liquid crystal composition of the present invention may contain components other than the above-mentioned components, and examples of such components include a surfactant, a tilt angle control agent, an alignment aid, a plasticizer, and a crosslinking agent.
• the benzoquinone derivative of the present invention is a compound represented by the above formula (A) (specific compound A).
• the cured liquid crystal layer of the present invention is a cured liquid crystal layer obtained by fixing the alignment state of the above-mentioned liquid crystal composition of the present invention.
• a method for forming the liquid crystal cured layer for example, a method in which the above-mentioned liquid crystal composition of the present invention is used to obtain a desired alignment state, and then the liquid crystal composition is fixed by polymerization, etc. can be mentioned.
• the polymerization conditions are not particularly limited, but in the polymerization by light irradiation, it is preferable to use ultraviolet light.
• 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 , further preferably 30 mJ/cm 2 to 3 J/cm 2 , and particularly preferably 50 mJ/cm 2 to 1000 mJ/cm 2.
• the polymerization may be carried out under heating conditions.
• the liquid crystal cured layer can be formed on any support or alignment film in an optical film described later, or on a polarizer in a polarizing plate described later.
• the orientation state of the liquid crystal compound in the liquid crystal cured layer of the present invention may be any of horizontal orientation, vertical orientation, tilt orientation, and twist orientation, and it is preferable that the liquid crystal compound is fixed in a horizontal orientation state with respect to the main surface of the liquid crystal cured layer.
• horizontal alignment refers to a state in which the major surface of the cured liquid crystal layer (or, when the cured liquid crystal layer is formed on a member such as a support or an alignment film, the surface of the member) is parallel to the long axis direction of the liquid crystal compound.
• the angle between the major surface of the cured liquid crystal layer and the long axis direction of the liquid crystal compound is less than 10°.
• the angle between the major axis direction of the liquid crystal compound and the main surface of the cured liquid crystal layer is preferably 0 to 5°, more preferably 0 to 3°, and even more preferably 0 to 2°.
• the liquid crystal cured layer of the present invention is preferably an optically anisotropic layer, more preferably a positive A plate or a positive C plate, and even more preferably a positive A plate.
• the positive A plate and the positive C plate are defined as follows.
• the refractive index in the slow axis direction the direction in which the in-plane refractive index is maximum
• the refractive index in the direction perpendicular to the in-plane slow axis is ny
• the refractive index in the thickness direction is nz
• the positive A plate satisfies the relationship of formula (A1)
• the positive C plate satisfies the relationship of formula (C1).
• the positive A plate has a positive Rth value
• the positive C plate has a negative Rth value.
• Re(550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, further preferably 130 to 150 nm, and particularly preferably 130 to 145 nm.
• ⁇ /4 plate refers to a plate having a ⁇ /4 function, specifically, a plate having the function of converting linearly polarized light of a certain wavelength into circularly polarized light (or circularly polarized light into linearly polarized light).
• the liquid crystal cured layer of the present invention can be used as a polarizer (light absorbing anisotropic film) when the above-mentioned liquid crystal composition of the present invention contains a dichroic material.
• the optical film of the present invention is an optical film having the liquid crystal cured layer of the present invention.
• the structure of the optical film will be described with reference to Fig. 1.
• Fig. 1 is a schematic cross-sectional view showing an example of the optical film. It should be noted that FIG. 1 is a schematic diagram, and the thickness and positional relationships of the layers do not necessarily correspond to the actual ones, and the support and alignment film shown in FIG. 1 are both optional components.
• An optical film 10 shown in FIG. 1 comprises, in this order, a support 16, an alignment film 14, and a liquid crystal cured layer 12 which is a cured product of the liquid crystal composition of the present invention.
• the liquid crystal cured layer 12 may be a laminate of two or more different liquid crystal cured layers.
• the polarizing plate of the present invention described later is used as a circular polarizing plate, or when the optical film of the present invention is used as an optical compensation film for an IPS (In-Plane-Switching) type or FFS (Fringe-Field-Switching) type liquid crystal display device, it is preferably a laminate of a positive A plate and a positive C plate.
• the liquid crystal cured layer may be peeled off from the support and used alone as an optical film.
• IPS In-Plane-Switching
• FFS Frringe-Field-Switching
• the liquid crystal cured layer in the optical film of the present invention is the above-mentioned liquid crystal cured layer of the present invention.
• the thickness of the cured liquid crystal layer is not particularly limited, but is preferably 0.1 to 10 ⁇ m, and more preferably 0.5 to 5 ⁇ m.
• the optical film may have a support as a substrate for forming the liquid crystal cured layer.
• a support is preferably transparent, and more specifically, preferably has a light transmittance of 80% or more.
• Such supports include glass substrates and polymer films.
• Methods of the polymer film include cellulose-based polymers, acrylic polymers having acrylic acid ester polymers such as polymethyl methacrylate and lactone ring-containing polymers, thermoplastic norbornene-based polymers, polycarbonate-based polymers, polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate, styrene-based polymers such as polystyrene and acrylonitrile-styrene copolymers (AS resins), polyolefin-based polymers such as polyethylene, polypropylene, and ethylene-propylene copolymers, vinyl chloride-based polymers, amide-based polymers such as nylon and aromatic polyamide, imide-based polymers, sulfone-based polymers, polyethersulfone-based polymers, polyetheretherketone-based polymers, polyphenylene sulfide-based polymers, vinylidene chloride-based polymers,
• the thickness of the support is not particularly limited, but is preferably 5 to 60 ⁇ m, and more preferably 5 to 40 ⁇ m.
• the liquid crystal cured layer is preferably formed on the surface of an alignment film (particularly, a photo-alignment film described later).
• the alignment film may be sandwiched between the support and the liquid crystal cured layer.
• the above-mentioned support may also serve as the alignment film.
• the alignment film may be any film that has the function of horizontally aligning the polymerizable liquid crystal compound contained in the composition.
• Alignment layers are generally made mainly of polymers. Polymer materials for alignment layers are described in many publications and many commercial products are available.
• the polymer material for the alignment film is preferably polyvinyl alcohol, polyimide, or any of their derivatives, and more preferably modified or unmodified polyvinyl alcohol.
• Examples of the alignment film that the optical film may have include the alignment film described in WO 01/88574, page 43, line 24 to page 49, line 8; the alignment film made of modified polyvinyl alcohol described in Japanese Patent No. 3907735, paragraphs [0071] to [0095]; and the liquid crystal alignment film formed from a liquid crystal alignment agent described in JP 2012-155308 A.
• the photo-alignment film is not particularly limited, and examples that can be used include alignment films formed from polymer materials such as polyamide compounds and polyimide compounds described in paragraphs [0024] to [0043] of International Publication No. 2005/096041; liquid crystal alignment films formed from liquid crystal alignment agents having photo-alignable groups described in JP-A-2012-155308; and LPP-JP265CP, a product of Rolic Technologies, Inc.
• the thickness of the alignment film is not particularly limited, but from the viewpoint of mitigating surface irregularities that may exist on the support and forming a liquid crystal cured layer with a uniform thickness, the thickness is preferably 0.01 to 10 ⁇ m, more preferably 0.01 to 1 ⁇ m, and even more preferably 0.01 to 0.5 ⁇ m.
• the cured liquid crystal layer is preferably formed on the surface of another cured liquid crystal layer.
• other liquid crystal cured layers include a liquid crystal cured layer obtained by fixing the alignment state of a composition obtained by removing the specific compound A from the above-mentioned liquid crystal composition of the present invention.
• Specific examples include a liquid crystal cured layer obtained by fixing the alignment state of a composition containing the above-mentioned liquid crystal compound, a polymerization initiator, a leveling agent, a solvent, and the like.
• the optical film preferably contains an ultraviolet (UV) absorbing agent.
• the ultraviolet absorbing agent may be contained in the liquid crystal cured layer, or may be contained in a member other than the liquid crystal cured layer constituting the optical film.
• a suitable example of the member other than the liquid crystal cured layer is the support.
• Any conventionally known ultraviolet absorbent capable of expressing ultraviolet absorbing properties can be used as the ultraviolet absorbent.
• benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorbents are preferred from the viewpoint of obtaining ultraviolet absorbing ability (ultraviolet ray blocking ability) that is high in ultraviolet absorbing properties and is used in image display devices.
• Examples of the ultraviolet absorber include the compounds described in JP-A-2012-18395, paragraphs [0258] to [0259] and the compounds described in JP-A-2007-72163, paragraphs [0055] to [0105].
• Commercially available products that can be used include Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, and Tinuvin 1577 (all manufactured by BASF).
• the polarizing plate of the present invention comprises the above-mentioned optical film of the present invention and a polarizer. Furthermore, when the above-mentioned liquid crystal cured layer of the present invention is a ⁇ /4 plate (positive A plate), the polarizing plate of the present invention can be used as a circular polarizing plate. In addition, in the polarizing plate of the present invention, when the above-mentioned liquid crystal cured layer of the present invention is a ⁇ /4 plate (positive A plate), the angle between the slow axis of the ⁇ /4 plate and the absorption axis of the polarizer described later is preferably 30 to 60°, more preferably 40 to 50°, further preferably 42 to 48°, and particularly preferably 45°.
• the "slow axis" of the ⁇ /4 plate means the direction in the plane of the ⁇ /4 plate in which the refractive index is maximum
• the "absorption axis" of the polarizer means the direction in which the absorbance is highest.
• the polarizing plate of the present invention can also be used as an optical compensation film for an IPS-type or FFS-type liquid crystal display device.
• the above-mentioned liquid crystal cured layer of the present invention can be at least one plate of a laminate of a positive A plate and a positive C plate, and is preferably a positive A plate.
• the angle between the slow axis of the positive A plate and the absorption axis of a polarizer described later is perpendicular or parallel, and more preferably, the angle between the slow axis of the positive A plate and the absorption axis of a polarizer described later is 0 to 5° or 85 to 95°.
• the polarizing plate of the present invention has a polarizer, a positive C plate, and a positive A plate laminated in this order, it is more preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer is parallel.
• the angle between the slow axis of the positive A plate and the absorption axis of the polarizer is perpendicular to each other.
• the angle between the slow axis of the cured liquid crystal layer and the absorption axis of the polarizer described later is preferably parallel or perpendicular.
• parallel does not require that they be strictly parallel, but means that the angle between one and the other is less than 10°.
• orthogonal does not require that they be strictly orthogonal, but means that the angle between one and the other is more than 80° and less than 100°.
• the polarizer in 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 linearly polarized light, and a conventionally known absorptive polarizer and reflective polarizer can be used.
• absorption-type polarizers include iodine-based polarizers, dye-based polarizers using dichroic dyes, polyene-based polarizers, etc.
• Iodine-based polarizers and dye-based polarizers include coating-type polarizers and stretching-type polarizers, and either can be used, but polarizers made by adsorbing iodine or a dichroic dye to polyvinyl alcohol and stretching it are preferred.
• methods of obtaining a polarizer by stretching and dyeing a laminated film in which a polyvinyl alcohol layer is formed on a substrate can be described in Japanese Patent No. 5,048,120, Japanese Patent No. 5,143,918, Japanese Patent No. 4,691,205, Japanese Patent No. 4,751,481, and Japanese Patent No. 4,751,486. These known techniques related to polarizers can also be preferably used.
• a polarizer in which thin films with different birefringence are laminated a wire grid type polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection region is combined with a quarter-wave plate, or the like is used.
• a polarizer containing a polyvinyl alcohol resin a polymer containing --CH 2 --CHOH-- as a repeating unit, in particular at least one selected from the group consisting of polyvinyl alcohol and an ethylene-vinyl alcohol copolymer is preferred in terms of superior adhesion.
• the thickness of the polarizer is not particularly limited, but is preferably 3 ⁇ m to 60 ⁇ m, more preferably 5 ⁇ m to 30 ⁇ m, and even more preferably 5 ⁇ m to 15 ⁇ m.
• the polarizing plate of the present invention may have a pressure-sensitive adhesive layer disposed between the cured liquid crystal layer in the optical film of the present invention and the polarizer.
• Adhesives that can be used in the present invention include, but are not limited to, polyvinyl alcohol-based 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 is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as "EL (Electro Luminescence)”) display panel, and a plasma display panel.
• EL Electro Luminescence
• a liquid crystal cell and an organic EL display panel are preferred, and a liquid crystal cell is more preferred.
• the image display device is preferably a liquid crystal display device using a liquid crystal cell as a display element, or an organic EL display device using an organic EL display panel as a display element, and more preferably a liquid crystal display device.
• a liquid crystal display device which is an example of an image display device, is a liquid crystal display device having the above-mentioned polarizing plate and a liquid crystal cell.
• the polarizing plates provided on both sides of the liquid crystal cell, it is preferable to use the above-mentioned polarizing plate as the front-side polarizing plate, and it is more preferable to use the above-mentioned polarizing plate as the front-side and rear-side polarizing plates.
• the liquid crystal cell constituting the liquid crystal display device will be described in detail below.
• the liquid crystal cell used in the liquid crystal display device is preferably in VA (Vertical Alignment) mode, OCB (Optically Compensated Bend) mode, IPS (In-Plane-Switching) mode, FFS (Fringe-Field-Switching) mode, or TN (Twisted Nematic) mode, but is not limited to these.
• VA Vertical Alignment
• OCB Optically Compensated Bend
• IPS In-Plane-Switching
• FFS Feringe-Field-Switching
• TN Transmission Nematic
• rod-shaped liquid crystal molecules are aligned substantially horizontally when no voltage is applied, and further aligned in a twisted manner at an angle of 60 to 120°.
• TN mode liquid crystal cells are most commonly used as color TFT liquid crystal display devices, and are described in many publications.
• VA mode liquid crystal cells In a VA mode liquid crystal cell, rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied.
• VA mode liquid crystal cells include (1) a narrow-sense VA mode liquid crystal cell (described in JP-A-2-176625) in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied and substantially horizontally when voltage is applied, (2) a VA mode (MVA mode) liquid crystal cell in which the VA mode is multi-domained to widen the viewing angle (described in SID97, Digest of tech.
• n-ASM mode liquid crystal cell in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied and are aligned in a twisted multi-domain manner when voltage is applied (described in Preprints 58-59 of the Japan Liquid Crystal Discussion Society (1998)), and (4) a SURVIVAL mode liquid crystal cell (announced at LCD International 98).
• the liquid crystal cell of the VA mode may be any of a PVA (Patterned Vertical Alignment) type, an optical alignment type, and a PSA (Polymer-Sustained Alignment) type.
• JP-A-10-54982 JP-A-11-202323, JP-A-9-292522, JP-A-11-133408, JP-A-11-305217, JP-A-10-307291, and the like.
• An organic EL display device which is an example of an image display device, may include, for example, a polarizer, a ⁇ /4 plate (positive A plate) made of the above-mentioned liquid crystal cured layer, and an organic EL display panel, which are arranged in this order from the viewing side.
• An example of the embodiment is as follows.
• An organic EL display panel is a display panel configured using organic EL elements in which an organic light-emitting layer (organic electroluminescence layer) is sandwiched between electrodes (cathode and anode).
• the configuration is not particularly limited, and a known configuration may be adopted.
• the filtered solid was washed with water and heptane, and crystallized from toluene to obtain a yellow solid (A-1-1).
• 2.45 g of aluminum chloride and 25 mL of toluene were added to a 100 mL three-neck flask and stirred under nitrogen.
• 2.5 g of the yellow solid (A-1-1) was added thereto and stirred at room temperature for 3 hours, and then further stirred at 60° C. for 5 hours. After that, it was allowed to cool to room temperature, 1N hydrochloric acid was added, and stirred for 30 minutes.
• the precipitated solid [mixture of (A-1) and (A-1-O)] was suction filtered, suspended and washed with 1N hydrochloric acid, and further washed with 25 mL of pure water.
• the obtained solid was oxidized with silver oxide by a general method (Tetrahedron letters 46.26 (2005): 4449-4451.), and 1.1 g of specific compound (A-1) was obtained.
• MS mass spectrometry
• Example 1 A liquid crystal composition 1 having the following composition was prepared. ⁇ Liquid crystal composition 1 ⁇ - 222.5 parts by mass of liquid crystal compound (B-1) below - 47.0 parts by mass of specific compound (A-1) below - 3.0 parts by mass of polymerizable compound (D-1) below - 1.5 parts by mass of polymerization initiator S1 below - 0.1 part by mass of leveling agent P1 below - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone
• Example 2 A liquid crystal composition 2 having the following composition was prepared.
• ⁇ Liquid crystal composition 2 ⁇ 222.5 parts by mass of the following liquid crystal compound (B-2) 47.0 parts by mass of the following specific compound (A-2) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 part by mass of the above leveling agent P1 92.5 parts by mass of cyclopentanone 64.2 parts by mass of methyl ethyl ketone
• Example 3 A liquid crystal composition 3 having the following composition was prepared.
• ⁇ Liquid crystal composition 3 ⁇ 222.5 parts by mass of the following liquid crystal compound (B-3) 47.0 parts by mass of the following specific compound (A-3) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 part by mass of the above leveling agent P1 92.5 parts by mass of cyclopentanone 64.2 parts by mass of methyl ethyl ketone
• Example 4 A liquid crystal composition 4 having the following composition was prepared. ⁇ Liquid crystal composition 4 ⁇ the liquid crystal compound (B-1) 222.5 parts by mass the specific compound (A-1) 55.6 parts by mass the polymerizable compound (D-1) 3.0 parts by mass the polymerization initiator S1 1.5 parts by mass the leveling agent P1 0.1 part by mass cyclopentanone 92.5 parts by mass methyl ethyl ketone 64.2 parts by mass
• Example 6 A liquid crystal composition 6 having the following composition was prepared. ⁇ Liquid crystal composition 6 ⁇ the liquid crystal compound (B-1) 222.5 parts by mass the specific compound (A-2) 47.0 parts by mass the polymerizable compound (D-1) 3.0 parts by mass the polymerization initiator S1 1.5 parts by mass the leveling agent P1 0.1 part by mass cyclopentanone 92.5 parts by mass methyl ethyl ketone 64.2 parts by mass
• Example 7 A liquid crystal composition 7 having the following composition was prepared. ⁇ Liquid crystal composition 7 ⁇ - 222.5 parts by mass of the following liquid crystal compound (B-5) - 47.0 parts by mass of the following specific compound (A-5) - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 part by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone
• Example 8 A liquid crystal composition 8 having the following composition was prepared.
• ⁇ Liquid crystal composition 8 ⁇ 222.5 parts by mass of the following liquid crystal compound (B-6) 47.0 parts by mass of the following specific compound (A-6) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 part by mass of the above leveling agent P1 92.5 parts by mass of cyclopentanone 64.2 parts by mass of methyl ethyl ketone
• Example 9 A liquid crystal composition 9 having the following composition was prepared.
• ⁇ Liquid crystal composition 9 ⁇ 222.5 parts by mass of the following liquid crystal compound (B-7) 47.0 parts by mass of the following specific compound (A-7) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 part by mass of the above leveling agent P1 92.5 parts by mass of cyclopentanone 64.2 parts by mass of methyl ethyl ketone
• a liquid crystal composition 10 having the following composition was prepared.
• ⁇ Liquid crystal composition 10 ⁇ - 222.5 parts by mass of the following liquid crystal compound (B-8) - 47.0 parts by mass of the following specific compound (A-8) - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 part by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone
• Example 11 A liquid crystal composition 11 having the following composition was prepared. ⁇ Liquid crystal composition 11 ⁇ - 222.5 parts by mass of the following liquid crystal compound (B-9) - 47.0 parts by mass of the following specific compound (A-9) - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 part by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone
• a liquid crystal composition C1 having the following composition was prepared.
• ⁇ Liquid crystal composition C1 ⁇ 269.5 parts by mass of the liquid crystal compound (B-1) 3.0 parts by mass of the polymerizable compound (D-1) 1.5 parts by mass of the polymerization initiator S1 0.1 part by mass of the leveling agent P1 92.5 parts by mass of cyclopentanone 64.2 parts by mass of methyl ethyl ketone
• a liquid crystal composition C2 having the following composition was prepared.
• ⁇ Liquid crystal composition C2 ⁇ ⁇ 222.5 parts by mass of the above liquid crystal compound (B-1) ⁇ 47.0 parts by mass of ADK STAB LA-29 ⁇ 3.0 parts by mass of the above polymerizable compound (D-1) ⁇ 1.5 parts by mass of the above polymerization initiator S1 ⁇ 0.1 part by mass of the above leveling agent P1 ⁇ 92.5 parts by mass of cyclopentanone ⁇ 64.2 parts by mass of methyl ethyl ketone
• the alignment was measured by placing an LED (Light Emitting Diode) light source, a lower polarizing plate, a liquid crystal cured layer (an optical film made from each liquid crystal composition), and an upper polarizing plate on a table from the bottom, so that each surface was horizontal. At this time, the sample and the upper polarizing plate were made rotatable. The luminance of the light emitted from the light source and transmitted through the lower polarizing plate, the sample, and the upper polarizing plate in this order was measured from the vertical direction using a luminance meter (BM-5A (manufactured by TOPCON)).
• BM-5A luminance meter
• the measurement was performed by first rotating the upper polarizing plate without a sample to the position where the luminance is the darkest (crossed Nicols state). The sample peeled off from the protective film was inserted between the polarizing plates, and the sample was rotated under crossed Nicols to measure the minimum luminance. Next, the upper and lower polarizing plates were placed in a parallel Nicols position, and the sample was rotated to measure the maximum luminance. In order to eliminate the contribution of luminance leakage due to the upper and lower polarizing plates, the value calculated by the following formula was evaluated according to the following evaluation criteria. The results are shown in Table 1 below.
• Orientation 1/((minimum luminance under crossed Nicols with a sample installed)/(maximum luminance under parallel Nicols with a sample installed)-(minimum luminance under crossed Nicols without a sample)/(maximum luminance under parallel Nicols without a sample)) ⁇ Evaluation criteria>
• Example 1 From the results shown in Table 1 above, it was found that when specific compound A was not blended, the light resistance was poor (Comparative Example 1). Moreover, when a compound other than the compound represented by the above formula (A) was blended, it was found that although the light resistance was improved, the alignment was inferior (Comparative Example 2). In contrast, it was found that when a liquid crystal composition containing specific compound A and a liquid crystal compound was used, a liquid crystal cured layer having good alignment properties and light resistance could be prepared (Examples 1 to 11). In particular, comparison between Example 1 and Example 4 revealed that the alignment was better when the content of specific compound A was 18 mass % or less with respect to the total mass of the specific compound and the liquid crystal compound.
• Example 1 In addition, from a comparison between Example 1 and Example 5, and a comparison between Example 2 and Example 6, it was found that, with respect to the structures of the compound represented by the above formula (A) (specific compound A) and the compound represented by the above formula (B) (liquid crystal compound), when Ar 1 in the above formula (A) and Ar 2 in the above formula (B) have the same structure, the alignment property becomes better.

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