Liquid crystal composition, monofunctional monomer, liquid crystal cured layer, optical film, polarizing plate, and image display device

Abstract

The present invention addresses the problem of providing a liquid crystal composition, a monofunctional monomer, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device which are suppressed in precipitation and excellent in alignment. This liquid crystal composition contains a compound represented by formula (A) and a liquid crystal compound. .

Description

Technical Field

[0001] This invention relates to a liquid crystal composition, a monofunctional monomer, a liquid crystal curing layer, an optical film, a polarizer, and an image display device. Background Technology

[0002] To eliminate image tinting and expand the viewing angle, optical films such as optical compensation sheets or phase retardation films are used in various image display devices.

[0003] Stretched birefringent films have been used as optical films, but in recent years, it has been proposed to use optical films with optical anisotropy layers composed of liquid crystal compounds as alternatives to stretched birefringent films.

[0004] As such optical films, optical films having a cured liquid crystal composition containing a compound represented by a prescribed formula and a polymerizable liquid crystal compound are known (for example, see Patent Document 1).

[0005] Previous technical documents Patent documents Patent Document 1: Japanese Patent Application Publication No. 2018-077465 Summary of the Invention

[0006] The technical problem to be solved by the invention The inventors studied the liquid crystal composition described in Patent Document 1 and found that it has an inhibitory effect on precipitation, but there is room for improvement in orientation.

[0007] Therefore, the objective of this invention is to provide a liquid crystal composition, a monofunctional monomer, a liquid crystal curing layer, an optical film, a polarizer, and an image display device that exhibit both excellent anti-exudation and orientation properties.

[0008] means for solving technical problems As a result of in-depth research conducted by the inventors to solve the above-mentioned problems, they discovered that if a liquid crystal composition containing a compound represented by formula (A) and a liquid crystal compound is used, the precipitation is suppressed and the orientation becomes good, thus completing the present invention.

[0009] That is, the inventors have discovered that the above-mentioned problems can be solved by the following configuration.

[0010] [1] A liquid crystal composition comprising a compound represented by the formula (A) described below and a liquid crystal compound.

[0011] [2] The liquid crystal composition according to [1], wherein the liquid crystal compound is a compound represented by formula (B) described later.

[0012] [3] The liquid crystal composition according to [1] or [2], wherein the content of the compound represented by the following formula (A) is 18% by mass or less relative to the total mass of the compound represented by the following formula (A) and the liquid crystal compound.

[0013] [4] The liquid crystal composition according to any one of [1] to [3], wherein Ar in formula (A) described later 1 It is an aromatic ring represented by formula (Ar-1) or (Ar-2) as described later.

[0014] [5] The liquid crystal composition according to any one of [2] to [4], wherein Ar in formula (A) described later 1 Ar in equation (B) described later 2 They have the same structure.

[0015] [6] The liquid crystal composition according to any one of [2] to [5], wherein G in formula (A) described later 11 With G in equation (B) described later 1 For the same structure, A in equation (A) described later 11 With A in equation (B) described later 1 They have the same structure.

[0016] [7] A monofunctional monomer, which is represented by formula (A) described later.

[0017] [8] A liquid crystal curing layer is formed by fixing the orientation state of the liquid crystal composition described in any one of [1] to [6].

[0018] [9] An optical film having the liquid crystal curing layer described in [8].

[0019]

[10] A polarizer having the optical film and polarizer described in [9].

[0020]

[11] An image display device having the optical film described in [9].

[0021] Invention Effects According to the present invention, a liquid crystal composition that suppresses precipitation and has excellent orientation can be provided, a monofunctional monomer, a liquid crystal curing layer, an optical film, a polarizer, and an image display device. Attached Figure Description

[0022] Figure 1 This is a schematic cross-sectional view showing an example of an optical film. Detailed Implementation

[0023] The present invention will now be described in detail.

[0024] The description of the constituent elements described below is sometimes made according to representative embodiments of the present invention, but the present invention is not limited to such embodiments.

[0025] In addition, in this specification, the numerical range indicated by “~” represents the range including the values ​​recorded before and after “~” as the lower limit and upper limit values.

[0026] Furthermore, in this specification, the upper or lower limit value of a numerical range recorded in a certain numerical range can be replaced with the upper or lower limit value of other numerical ranges recorded in a certain period. Also, the upper or lower limit value of a numerical range recorded in this specification can be replaced with the value shown in the embodiment.

[0027] Furthermore, in this specification, each component may be used alone as one of its own substances, or two or more substances may be used together. Where two or more substances are used simultaneously for each component, the content of that component, unless otherwise stated, refers to the total content of the substances used simultaneously.

[0028] Furthermore, in this specification, "(meth)acrylate" is the expression for "acrylate" or "methacrylate", "(meth)acrylate group" is the expression for "acrylate group" or "methacrylate group", and "(meth)acryloyl group" is the expression for "acryloyl group" or "methacryloyl group".

[0029] Furthermore, the bonding direction of the divalent groups (e.g., -O-CO-) described in this specification is not particularly limited; for example, in "L 1 -L 2 -L 3 In the bonding of ", in L 2 In the case of -O-CO-, if the bond is placed on L 1 The side position is set as 1. Bonded to L 3 The side position is set as 2, then L 2 It can be 1-O-CO- 2, can also be 1-CO-O- 2.

[0030] Furthermore, in this specification, Re(λ) and Rth(λ) represent the in-plane delay and the thickness direction delay at wavelength λ, respectively. Unless otherwise specified, wavelength λ is set to 550 nm.

[0031] In this invention, Re(λ) and Rth(λ) are values ​​obtained by measurement at wavelength λ using an AxoScan (manufactured by Axometrics). The following values ​​are calculated by inputting the average refractive index ((nx+ny+nz) / 3) and film thickness (d(μm)) into the AxoScan: Slow axis direction (°); Re(λ) = R0(λ); and Rth(λ)=((nx+ny) / 2-nz)×d.

[0032] Additionally, R0(λ) is displayed as a value calculated by AxoScan, but refers to Re(λ).

[0033] Furthermore, in this specification, as a substituent (a monovalent substituent), for example, the substituent described in substituent group A described below can be cited.

[0034] Furthermore, in this specification, "may have substituents" includes not only the form without substituents, but also the form with one or more substituents.

[0035] <Substituent group A> As a substituent, for example, can be cited as follows: Halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, preferably chlorine atom, fluorine atom, more preferably fluorine atom); Alkyl groups (preferably straight-chain, branched, or cyclic alkyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and especially preferably 1 to 8 carbon atoms, for example, straight-chain alkyl groups having 1 to 6 carbon atoms (e.g., methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl), branched alkyl groups having 3 to 6 carbon atoms (e.g., isopropyl, isobutyl, tert-butyl, sec-butyl, neopentyl, isohexyl, 3-methylpentyl), and cyclic alkyl groups having 3 to 12 carbon atoms (e.g., cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, 1-adamantyl)). Alkenyl (preferably alkenyl with 2 to 48 carbon atoms, more preferably alkenyl with 2 to 18 carbon atoms, for example, vinyl, allyl, 1-butenyl, 2-butenyl); Alkynyl (preferably an alkynyl group with 2 to 6 carbon atoms, more preferably an alkynyl group with 2 to 4 carbon atoms, for example, ethynyl, 1-propynyl, propynyl, 1-butynyl, 2-butynyl); Aryl (preferably aryl with 6 to 48 carbon atoms, more preferably aryl with 6 to 24 carbon atoms, for example, phenyl, oligoaryl (naphthyl, anthracene), phenanthrene, fluorene, pyrene, triphenylene, biphenyl); Heteroaryl groups (preferably heterocyclic groups with 1 to 32 carbon atoms, more preferably heterocyclic groups with 1 to 18 carbon atoms, for example, 2-thienyl, 4-pyridyl, 2-furanyl, 2-pyrimidinyl, 1-pyridyl, 2-benzothiazolyl, 1-imidazolyl, 1-pyrazolyl, benzotriazol-1-yl); Aryl alkyl group (preferably an aryl alkyl group having 7 to 15 carbon atoms, for example, benzyl, phenethyl, methylbenzyl, phenylpropyl, 1-methylphenylethyl, phenylbutyl, 2-methylphenylpropyl, tetrahydronaphthyl, naphthylmethyl, naphthylethyl, indene, fluorenyl, anthrylmethyl, phenanthrylmethyl)); Silyl group (preferably silyl group with 3 to 38 carbon atoms, more preferably silyl group with 3 to 18 carbon atoms, for example, trimethylsilyl, triethylsilyl, tributylsilyl, tert-butyldimethylsilyl, tert-hexyldimethylsilyl); Hydroxyl; cyano; nitro; morpholino; Alkoxy groups (preferably alkoxy groups with 1 to 48 carbon atoms, more preferably alkoxy groups with 1 to 24 carbon atoms, such as methoxy, ethoxy, 1-butoxy, 2-butoxy, isopropoxy, tert-butoxy, dodecyloxy, cycloalkoxy (e.g., cyclopentoxy, cyclohexyloxy)). Aryloxy group (preferably an aryloxy group with 6 to 48 carbon atoms, more preferably an aryloxy group with 6 to 24 carbon atoms, for example, phenoxy group, 1-naphthoxy group); Alkenyloxy group (preferably an alkenyloxy group having 2 to 6 carbon atoms, for example, ethyleneoxy, 1-propenoxy, 2-n-propenoxy (allyloxy), 1-n-butenoxy, isopreneoxy). Heterocyclic groups (preferably heterocyclic groups with 1 to 32 carbon atoms, more preferably heterocyclic groups with 1 to 18 carbon atoms, for example, 1-phenyltetrazole-5-oxy, 2-tetrahydropyranoxy); Silyoxy group (preferably siloxy group with 1 to 32 carbon atoms, more preferably siloxy group with 1 to 18 carbon atoms, for example, trimethylsiloxy group, tert-butyldimethylsiloxy group, diphenylmethylsiloxy group). Acyloxy group (preferably an acyloxy group with 2 to 48 carbon atoms, more preferably an acyloxy group with 2 to 24 carbon atoms, for example, acetoxy, neopentyloxy, benzoyloxy, dodecyloxy, acryloyloxy, methacryloyloxy). Hydroxyalkoxide (preferably a hydroxyalkoxide with 2 to 10 carbon atoms, for example, hydroxyethoxy); Alkoxycarbonyloxy (preferably alkoxycarbonyloxy with 2 to 48 carbon atoms, more preferably alkoxycarbonyloxy with 2 to 24 carbon atoms, for example, ethoxycarbonyloxy, tert-butoxycarbonyloxy, cycloalkoxycarbonyloxy (for example, cyclohexyloxycarbonyloxy)); Aryloxycarbonyloxy (preferably aryloxycarbonyloxy with 7 to 32 carbon atoms, more preferably aryloxycarbonyloxy with 7 to 24 carbon atoms, for example, phenoxycarbonyloxy); Carbamoyloxy (preferably carbamoyloxy with 1 to 48 carbon atoms, more preferably with 1 to 24 carbon atoms, for example, N,N-dimethylcarbamoyloxy, N-butylcarbamoyloxy, N-phenylcarbamoyloxy, N-ethyl-N-phenylcarbamoyloxy). Aminosulfonyloxy (preferably an aminosulfonyloxy with 1 to 32 carbon atoms, more preferably an aminosulfonyloxy with 1 to 24 carbon atoms, for example, N,N-diethylaminosulfonyloxy, N-propylaminosulfonyloxy). Alkylsulfonyloxy (preferably alkylsulfonyloxy with 1 to 38 carbon atoms, more preferably alkylsulfonyloxy with 1 to 24 carbon atoms, for example, methylsulfonyloxy, hexadecylsulfonyloxy, cyclohexylsulfonyloxy); Arylsulfonyloxy group (preferably arylsulfonyloxy group with 6 to 32 carbon atoms, more preferably arylsulfonyloxy group with 6 to 24 carbon atoms, for example, phenylsulfonyloxy group); Acyl group (preferably an acyl group with 1 to 48 carbon atoms, more preferably an acyl group with 1 to 24 carbon atoms, for example, formyl, acetyl, acryloyl, methacryloyl, neopentyl, benzoyl, tetradecanoyl, cyclohexyl); Alkoxycarbonyl (preferably an alkoxycarbonyl with 2 to 48 carbon atoms, more preferably an alkoxycarbonyl with 2 to 24 carbon atoms, for example, methoxycarbonyl, ethoxycarbonyl, octadecyloxycarbonyl, cyclohexyloxycarbonyl, 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl); Aryloxycarbonyl (preferably an aryloxycarbonyl with 7 to 32 carbon atoms, more preferably an aryloxycarbonyl with 7 to 24 carbon atoms, for example, phenoxycarbonyl); Carbamoyl group (preferably a carbamoyl group with 1 to 48 carbon atoms, more preferably a carbamoyl group with 1 to 24 carbon atoms, for example, carbamoyl group, N,N-diethylcarbamoyl group, N-ethyl-N-octylcarbamoyl group, N,N-dibutylcarbamoyl group, N-propylcarbamoyl group, N-phenylcarbamoyl group, N-methyl-N-phenylcarbamoyl group, N,N-dicyclohexylcarbamoyl group); Amino group (preferably an amino group with 32 or fewer carbon atoms, more preferably an amino group with 24 or fewer carbon atoms, for example, amino, methylamino, N,N-dibutylamino, tetradecylamino, 2-ethylhexylamino, cyclohexylamino). Aniline (preferably aniline with 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, aniline or N-methylaniline); Heterocyclic amino group (preferably a heterocyclic amino group with 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 4-pyridylamino group); Carboxylamide group (preferably a carboxylamide group with 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetamide group, benzamide group, tetradecanoamide group, neopentanoylamide group, cyclohexaneamide group); Urea group (preferably a urea group with 1 to 32 carbon atoms, more preferably a urea group with 1 to 24 carbon atoms, for example, urea group, N,N-dimethylurea group, N-phenylurea group); Imide group (preferably an imide group with 36 or fewer carbon atoms, more preferably an imide group with 24 or fewer carbon atoms, for example, N-succinimide group, N-phthalimide group); Alkoxycarbonylamino (preferably alkoxycarbonylamino with 2 to 48 carbon atoms, more preferably alkoxycarbonylamino with 2 to 24 carbon atoms, for example, methoxycarbonylamino, ethoxycarbonylamino, tert-butoxycarbonylamino, octadecyloxycarbonylamino, cyclohexyloxycarbonylamino). Aryloxycarbonylamino (preferably aryloxycarbonylamino with 7 to 32 carbon atoms, more preferably aryloxycarbonylamino with 7 to 24 carbon atoms, for example, phenoxycarbonylamino); Sulfonamide group (preferably a sulfonamide group with 1 to 48 carbon atoms, more preferably a sulfonamide group with 1 to 24 carbon atoms, for example, methanesulfonamide group, butanesulfonamide group, benzenesulfonamide group, hexadecanesulfonamide group, cyclohexanesulfonamide group); Aminosulfonylamino (preferably an aminosulfonylamino with 1 to 48 carbon atoms, more preferably an aminosulfonylamino with 1 to 24 carbon atoms, for example, N,N-dipropylaminosulfonylamino, N-ethyl-N-dodecylaminosulfonylamino). Azo group (preferably an azo group with 1 to 32 carbon atoms, more preferably an azo group with 1 to 24 carbon atoms, for example, phenyl azo group, 3-pyrazolyl azo group); Alkylthio (preferably alkylthio with 1 to 48 carbon atoms, more preferably alkylthio with 1 to 24 carbon atoms, for example, methylthio, ethylthio, octylthio, cyclohexylthio); Arylthio (preferably arylthio with 6 to 48 carbon atoms, more preferably arylthio with 6 to 24 carbon atoms, for example, phenylthio); Heterocyclic thio groups (preferably heterocyclic thio groups with 1 to 32 carbon atoms, more preferably heterocyclic thio groups with 1 to 18 carbon atoms, for example, 2-benzothiazolyl thio group, 2-pyridyl thio group, 1-phenyltetrazole thio group); Alkyl sulfinyl group (preferably an alkyl sulfinyl group with 1 to 32 carbon atoms, more preferably an alkyl sulfinyl group with 1 to 24 carbon atoms, for example, dodecane sulfinyl group); Arylsulfinyl group (preferably arylsulfinyl group with 6 to 32 carbon atoms, more preferably arylsulfinyl group with 6 to 24 carbon atoms, for example, phenylsulfinyl group); Alkyl sulfonyl group (preferably an alkyl sulfonyl group with 1 to 48 carbon atoms, more preferably an alkyl sulfonyl group with 1 to 24 carbon atoms, for example, methyl sulfonyl, ethyl sulfonyl, propyl sulfonyl, butyl sulfonyl, isopropyl sulfonyl, 2-ethylhexyl sulfonyl, hexadecyl sulfonyl, octyl sulfonyl, cyclohexyl sulfonyl). Arylsulfonyl group (preferably arylsulfonyl group with 6 to 48 carbon atoms, more preferably arylsulfonyl group with 6 to 24 carbon atoms, for example, phenylsulfonyl group, 1-naphthylsulfonyl group); Aminosulfonyl group (preferably an aminosulfonyl group with 32 or fewer carbon atoms, more preferably an aminosulfonyl group with 24 or fewer carbon atoms, for example, aminosulfonyl group, N,N-dipropylaminosulfonyl group, N-ethyl-N-dodecylaminosulfonyl group, N-ethyl-N-phenylaminosulfonyl group, N-cyclohexylaminosulfonyl group, N-(2-ethylhexyl)aminosulfonyl group); Phosphonoyl group (preferably a phosphonoyl group with 1 to 32 carbon atoms, more preferably a phosphonoyl group with 1 to 24 carbon atoms, for example, phenoxyphosphonoyl group, octoxyphosphonoyl group, phenylphosphonoyl group); Oxyphosphinoamino (preferably oxyphosphinoamino with 1 to 32 carbon atoms, more preferably oxyphosphinoamino with 1 to 24 carbon atoms, for example, ethoxyphosphinoamino, dioctyloxyphosphinoamino). Epoxy groups; -NHCOCH3; -SO2NHC2H4OCH3; -NHSO2CH3; These can be combined in two or more ways.

[0036] These substituents can also be replaced by these substituents. Furthermore, when there are two or more substituents, they can be the same or different. And, where possible, they can bond together to form a ring.

[0037] [Liquid Crystal Composition] The liquid crystal composition of the present invention is a liquid crystal composition containing a compound represented by the formula (A) described below (hereinafter also simply referred to as "specific compound A") and a liquid crystal compound.

[0038] In this invention, as described above, if a liquid crystal composition containing a specific compound A and a liquid crystal compound is used, precipitation is suppressed and orientation becomes good.

[0039] Although its details are not yet clear, the inventors speculate as follows.

[0040] That is, it is speculated that the X in formula (A) described below is derived from the fact that a specific compound A has a defined functional group such as an alkoxy group. 1 Compared to cases with functional groups containing active hydrogen (e.g., hydroxyl groups), it can suppress precipitation (e.g., crystallization of liquid crystal compounds) without hindering the orientation of the liquid crystal compound.

[0041] Hereinafter, a specific compound A and the liquid crystal compound contained in the liquid crystal composition of the present invention will be described in detail.

[0042] [Specific compound A] A specific compound A is a compound represented by the following formula (A).

[0043] [Chemical Formula 1] In the above formula (A), P 1 It indicates a polymerizable group.

[0044] Here, there is no particular limitation on the polymerizable group, but it is preferred to be a polymerizable group that can be polymerized by free radical or cationic polymerization.

[0045] As a free radical polymerizable group, known free radical polymerizable groups can be used, and acryloyloxy or methacryloyloxy are examples of preferred free radical polymerizable groups. It is known that in this case, acryloyloxy generally polymerizes faster, and from the viewpoint of improving productivity, acryloyloxy is preferred. Methacryloxy can also be used as a polymerizable group in the same way.

[0046] As the cationic polymerizable group, known cationic polymerizable groups can be used. Specifically, examples include alicyclic ether groups, cyclic acetal groups, cyclic lactone groups, cyclic thioether groups, spirocyclic orthoester groups, and ethyleneoxy groups. Among these, alicyclic ether groups or ethyleneoxy groups are preferred, and epoxy groups, oxetyl groups, or ethyleneoxy groups are particularly preferred.

[0047] As a particularly preferred example of a polymeric group, one can cite a polymeric group represented by any one of the following formulas (P-1) to (P-20).

[0048] [Chemical Formula 2] In the above formula (A), F 1 Indicates a spacer group.

[0049] Here, as a spacer group, examples include divalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms. In this case, one or more of the -CH2- atoms constituting the aliphatic hydrocarbon group can be replaced by -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent. Furthermore, the hydrogen atoms contained in the aliphatic hydrocarbon group can be independently replaced by halogen atoms, alkyl groups, or alkoxy groups.

[0050] Furthermore, examples of divalent aliphatic hydrocarbon groups with 1 to 20 carbon atoms include linear or branched alkylene groups with 1 to 20 carbon atoms, alkenyl groups with 1 to 20 carbon atoms, and alkyne groups with 1 to 20 carbon atoms.

[0051] As a straight-chain or branched alkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 12 carbon atoms is preferred, and an alkylene group having 1 to 10 carbon atoms is more preferred. Examples of preferred alkylene groups include methylene, ethylene, propylene, butylene, pentylene, and hexylene.

[0052] As a straight-chain or branched alkenyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 10 carbon atoms is preferred, and an alkenyl group with 2 to 4 carbon atoms is more preferred, for example, vinylidene.

[0053] As a straight-chain or branched ynyl group with 1 to 20 carbon atoms, an ynyl group with 2 to 10 carbon atoms is preferred, and an ynyl group with 2 to 4 carbon atoms is more preferred, for example, an ethynyl group.

[0054] In addition, as described above, one or more of the -CH2- constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO- as a substituent represented by Q. Examples of substituents described in substituent group A above are examples, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy or halogen atoms are preferred.

[0055] In the above formula (A), B 1 E 1 and D 11 Each can be represented independently as a single bond or a divalent linker.

[0056] Here, examples of divalent linking groups include -CO-, -O-, -S-, -C(=S)-, and -CR-. 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linking group composed of two or more of these, etc. Additionally, R 1 ~R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0057] Divalent linking groups, specifically, for example, include -CO-, -O-, -CO-O-, -C(=S)O-, and -CR. 1 R 2 -、-CR 1 R 2 -CR1 R 2 -、-O-CR 1 R 2 -、-CR 1 R 2 -O-CR 1 R 2 -、-CO-O-CR 1 R 2 -、-O-CO-CR 1 R 2 -、-CR 1 R 2 -O-CO-CR 1 R 2 -、-CR 1 R 2 -CO-O-CR 1 R 2 -、-NR 5 -CR 1 R 2 -and-CO-NR 5 - etc. R 1 R 2 and R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0058] Among these, the preferred choice is any one of -CO-, -O-, and -CO-O-.

[0059] In the above formula (A), A 11 and G 11 Each can be independently represented as a divalent aromatic hydrocarbon group with 6 to 20 carbon atoms or a divalent alicyclic hydrocarbon group with 3 to 16 carbon atoms.

[0060] Here, the number of carbon atoms in the divalent aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 16, even more preferably 6 to 10, and particularly preferably 6.

[0061] Furthermore, the number of carbon atoms in the divalent alicyclic hydrocarbon group is preferably 4 to 15, more preferably 5 to 10, and even more preferably 5 or 6.

[0062] The hydrogen atoms contained in a divalent aromatic hydrocarbon group or a divalent alicyclic hydrocarbon group can be independently replaced by halogen atoms (e.g., fluorine, chlorine, bromine, and iodine atoms), -R L1 -OR L1 Cyano or nitro substitution. Additionally, R L1 An alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atoms contained in the alkyl group can be independently replaced by fluorine atoms.

[0063] Here, as RL1 Alkyl groups having 1 to 4 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, etc., are preferred, alkyl groups having 1 to 3 carbon atoms are more preferred, alkyl groups having 1 or 2 carbon atoms are even more preferred, and methyl is even more preferred.

[0064] Furthermore, as -OR L1 The alkoxy group having 1 to 4 carbon atoms includes, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, etc., preferably an alkoxy group having 1 to 3 carbon atoms, more preferably an alkoxy group having 1 or 2 carbon atoms, and even more preferably a methoxy group.

[0065] In divalent aromatic hydrocarbon groups and divalent alicyclic hydrocarbon groups, the carbon atoms can be independently replaced by oxygen, sulfur, or nitrogen atoms. One carbon atom can be replaced by an oxygen, sulfur, or nitrogen atom, or two or more carbon atoms can be replaced by two or more atoms selected from the group consisting of oxygen, sulfur, and nitrogen atoms. For example, the -CH= group in a divalent aromatic hydrocarbon group can be replaced by -N=. Furthermore, the -CH2- (methylene) group in a divalent alicyclic hydrocarbon group can be independently replaced by -O-, -S-, -NH-, or -NR. L1 - Substitution: The -CH(-)- group contained in the alicyclic hydrocarbon group can be independently substituted by -N(-). Here, R L1 The meaning is the same as above.

[0066] Examples of divalent aromatic hydrocarbon groups include those represented by formulas (a-1) to (a-8). A 1,4-phenylene group is preferred as the divalent aromatic hydrocarbon group.

[0067] [Chemical Formula 3] Examples of divalent alicyclic hydrocarbon groups include those represented by formulas (g-1) to (g-4). The -CH2- group contained in the alicyclic hydrocarbon group is replaced by -O-, -S-, -NH-, or -NR. L1 Examples of divalent alicyclic hydrocarbon groups with -substituted -CH(-)-substituted with -N(-)-substituted in the alicyclic hydrocarbon group include groups represented by formulas (g-9) and (g-10). These are preferably 5-membered or 6-membered alicyclic hydrocarbon groups.

[0068] [Chemical Formula 4] From the viewpoint of manufacturing the compounds of the present invention, the divalent alicyclic hydrocarbon group is preferably a cycloalkyldiyl group represented by formula (g-1), more preferably a cyclohexane-1,4-diyl group, and even more preferably a trans-cyclohexane-1,4-diyl group.

[0069] In this invention, from the viewpoint of manufacturing a specific compound A, A 11 Preferably, it is a divalent aromatic hydrocarbon group.

[0070] Furthermore, from the viewpoint of compatibility with liquid crystal compounds, G 11 Preferably, it is a divalent alicyclic hydrocarbon group, more preferably cyclohexane-1,4-diyl, and even more preferably trans-cyclohexane-1,4-diyl.

[0071] In equation (A) above, m1 and n1 independently represent integers from 0 to 3. When m1 is 2 or 3, multiple B... 1 Multiple A's can be the same or different. 11 They can be the same or different. When n1 is 2 or 3, multiple E... 1 They can be the same or different, multiple Gs 11 They can be the same or different.

[0072] Here, both m1 and n1 can be 0, but if either one is 0, it is preferable for the other to represent an integer of 2 or 3.

[0073] Furthermore, m1 and n1 are both preferably 1 or 2, and more preferably 1.

[0074] In the above formula (A), X 1 Indicates -OR L2 -O-(C=O)-R L3 -O-(C=O)-OR L4 -O-(C=O)-NH-R L5 -O-(C=O)-NR L6 -R L7 Or -O-(C=S)-R L8 .

[0075] Additionally, R L2 R represents an alkyl, acryloyl, or methacryloyl group having 1 to 4 carbon atoms. L3 R represents an alkyl group having 1 to 4 carbon atoms. L4 ~R L8 Each can be independently represented as an acyclic alkyl group, a monovalent aromatic group, or a monovalent alicyclic group.

[0076] Here, alkyl groups having 1 to 4 carbon atoms are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, etc., preferably alkyl groups having 1 to 3 carbon atoms, more preferably alkyl groups having 1 or 2 carbon atoms, and even more preferably methyl.

[0077] Furthermore, acyclic alkyl groups can be categorized in terms of the number of carbon atoms from 1 to 6, specifically including methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl. Additionally, acyclic alkyl groups preferably do not have substituents.

[0078] Examples of monovalent aromatic groups include, for instance, aromatic hydrocarbon groups with 6 to 12 carbon atoms; aromatic heterocyclic groups with 3 to 12 carbon atoms; and more specifically, aryl groups such as phenyl, 2,6-diethylphenyl, and naphthyl; and heteroaryl groups such as thienyl, thiazolyl, furanyl, and pyridyl; etc. Furthermore, the monovalent aromatic group preferably does not have substituents.

[0079] Examples of monovalent alicyclic groups include alicyclic hydrocarbon groups with 6 to 20 carbon atoms, specifically cyclohexylene, cyclopentylene, norbornylene, and adamantylene. Furthermore, the monovalent alicyclic group preferably does not have substituents.

[0080] In this invention, considering the reasons of further suppressing precipitation and improving orientation, X 1 Preferred option: -OR L2 Or -O-(C=O)-R L3 More preferably, it is methoxy (-OCH3), ethoxy (-OCH2CH3), butoxy (-OCH2CH2CH2CH3) or acetoxy (-OC(=O)-CH3).

[0081] In the above formula (A), Ar 1 This represents any aromatic ring selected from the group consisting of the groups represented by formulas (Ar-1) to (Ar-3) below. Furthermore, in formulas (Ar-1) to (Ar-3) below, This indicates that D in equation (A) above... 11 or X 1 The bonding positions.

[0082] [Chemical Formula 5] In the above equation (Ar-1), Q 1 Represents N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Y represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms.1 It indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- constituting the alicyclic hydrocarbon group can be replaced by -O-, -S- or -NH-.

[0083] Among them, as R 6 The alkyl group having 1 to 6 carbon atoms is represented in one manner. Specifically, examples include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.

[0084] As Y 1 The aromatic hydrocarbon group with 6 to 12 carbon atoms is represented in one way, for example, aryl groups such as phenyl, 2,6-diethylphenyl, and naphthyl.

[0085] As Y 1 The aromatic heterocyclic group with 3 to 12 carbon atoms, represented in one manner, includes, for example, heteroaryl groups such as thienyl, thiazolyl, furanyl, and pyridyl, as well as groups formed by removing one hydrogen atom from any one of the indole ring, benzofuran ring, benzothiophene ring, benzimidazole ring, benzothiazole ring, and benzoxazole ring. Among these, Y... 1 The aromatic heterocyclic group represented by carbon atoms with 3 to 12 is preferably a group formed by removing one hydrogen atom from the benzofuran ring or the benzothiazole ring.

[0086] As Y 1 The alicyclic hydrocarbon group with 6 to 20 carbon atoms can be represented in one way, for example, cyclohexylene, cyclopentylene, norbornylene, adamantylene, etc.

[0087] And, as Y 1 The substituents that may be present include those described in substituent group A above, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, nitro, cyano or halogen atoms are preferred.

[0088] Furthermore, in the above equations (Ar-1) to (Ar-3), Z 1 and Z 2 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings.

[0089] As a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 15 carbon atoms is preferred, an alkyl group having 1 to 8 carbon atoms is more preferred, and specifically, methyl, ethyl, isopropyl, tert-amyl (1,1-dimethylpropyl), tert-butyl, 1,1-dimethyl-3,3-dimethyl-butyl is even more preferred, and methyl, ethyl, and tert-butyl are particularly preferred.

[0090] Examples of monocyclic alicyclic hydrocarbon groups with 3 to 20 carbon atoms include monocyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, methylcyclohexyl, and ethylcyclohexyl; monocyclic unsaturated hydrocarbon groups such as cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, cyclopentadienyl, cyclohexadienyl, cyclooctadienyl, and cyclodecadienyl; and bicyclic [2.2.1]heptyl, bicyclic [2.2.2]octyl, and tricyclic [5.2.1.0]heptyl. 2,6 ] decyl, tricyclic [3.3.1.1] 3,7 ] decyl, tetracyclic [6.2.1.1 3,6 .0 2,7 Polycyclic saturated hydrocarbon groups such as dodecyl and adamantyl; etc.

[0091] The aromatic hydrocarbon group with a carbon number of 6 to 20 is a monovalent aromatic hydrocarbon group. Specifically, examples include phenyl, 2,6-diethylphenyl, naphthyl, biphenyl, etc., and preferably an aryl group with a carbon number of 6 to 12 (especially phenyl).

[0092] As a monovalent aromatic heterocyclic group with 6 to 20 carbon atoms, examples include 4-pyridyl, 2-furanyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, etc.

[0093] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms, with fluorine, chlorine, and bromine atoms being preferred.

[0094] On the other hand, as R 7 ~R 10 The alkyl group represented by carbon atoms is 1 to 6. Specifically, examples include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.

[0095] As mentioned above, Z 1 and Z2 They can bond with each other to form aromatic rings, for example, as Z in the above formula (Ar-1). 1 and Z 2 The structure in which groups bond together to form an aromatic ring can be exemplified by groups represented by the following formula (Ar-1a). Furthermore, in the following formula (Ar-1a), This indicates that D in equation (A) above... 11 or X 1 The bonding positions.

[0096] [Chemical Formula 6] In the above formula (Ar-1a), Q 1 Q 2 and Y 1 Groups that are the same as those described in the above formula (Ar-1) can be cited.

[0097] Furthermore, in the above equations (Ar-2) and (Ar-3), A 3 and A 4 Represent the selection independently of -O- and -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 It represents a hydrogen atom or a substituent.

[0098] As R 13 The substituents represented in one manner may be those described in the substituent group A above, wherein preferably alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy or halogen atoms.

[0099] Furthermore, in the above formula (Ar-2), X represents a nonmetallic atom from groups 14 to 16. This nonmetallic atom may be bonded with hydrogen atoms or substituents.

[0100] Furthermore, examples of nonmetallic atoms in groups 14-16 represented by X include, for example, oxygen atoms, sulfur atoms, and nitrogen atoms bonded with hydrogen atoms or substituents [=NR]. N1 R N1 Represents a hydrogen atom or substituent. A carbon atom bonded with a hydrogen atom or substituent [=C-(R] C1 )2,R C1 This represents a hydrogen atom or a substituent.

[0101] Examples of substituents can be found in the substituent group A described above, with alkyl, alkoxy, alkyl-substituted alkoxy, cyclic alkyl, aryl (e.g., phenyl, naphthyl, etc.), cyano, amino, nitro, alkyl carbonyl, sulfonyl, hydroxyl, etc. being preferred.

[0102] Furthermore, in the above equation (Ar-3), D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linker consisting of two or more of them, R 1 ~R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0103] Here, as a divalent linking group, one can exemplify the relationship between B and B in the above formula (A). 1 E 1 and D 11 The same group as the group described in the text.

[0104] Furthermore, in the above formula (Ar-3), SP 3 and SP 4 Each of these groups independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. One or more of the -CH2- groups constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent. Examples of substituents represented by Q are those described in substituent group A above, preferably alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms.

[0105] Here, as a divalent aliphatic hydrocarbon group, examples can be given that it is related to F in the above formula (A). 1 The same group as the group described in the text.

[0106] Furthermore, in the above equation (Ar-3), L 3 and L 4 Each of these represents a monovalent organic group independently.

[0107] Here, as a monovalent organic group, examples include the substituents described in the substituent group A above, among which alkyl, aryl, heteroaryl, alkoxy, cyano and carboxyl groups are preferred.

[0108] The alkyl group can be straight-chain, branched, or cyclic, but is preferably straight-chain. The alkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 10.

[0109] Furthermore, the aryl group can be either monocyclic or polycyclic, but is preferably monocyclic. The number of carbon atoms in the aryl group is preferably 6 to 25, more preferably 6 to 10.

[0110] Furthermore, the heteroaryl group can be monocyclic or polycyclic. The number of heteroatoms constituting the heteroaryl group is preferably 1 to 3. The heteroatoms constituting the heteroaryl group are preferably nitrogen, sulfur, or oxygen atoms. The number of carbon atoms in the heteroaryl group is preferably 6 to 18, more preferably 6 to 12.

[0111] Furthermore, the alkyl, aryl, and heteroaryl groups may be unsubstituted or may have substituents. Examples of substituents include those described in substituent group A above, with alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms being preferred.

[0112] Furthermore, the monovalent organic group can be a polymerizable group, for example, preferably a polymerizable group represented by any one of the above formulas (P-1) to (P-20).

[0113] In this invention, from the viewpoint of satisfying the desired optical properties, Ar in the above formula (A) 1 Preferably, it is an aromatic ring represented by the above formula (Ar-1) or (Ar-2).

[0114] As a specific compound A, it is preferable to cite compounds represented by the following formulas (1) to (17). Specifically, as K (side chain structure) in the following formulas (1) to (17), compounds having the side chain structures shown in Tables 1 to 3 and X in the following formulas (1) to (17) can be cited. 1 Compounds represented by methoxy (-OCH3), ethoxy (-OCH2CH3), butoxy (-OCH2CH2CH2CH3), or acetoxy (-OC(=O)-CH3), or K and X in formulas (2), (3), (5) to (8), (11), (13) to (17) below. 1 Interchangeable compounds, etc.

[0115] Additionally, in Tables 1 to 3 below, the side chain structure of K is shown as " "" indicates the bonding position with the aromatic ring.

[0116] Furthermore, in the side chain structures represented by 2-2 in Table 2 and 3-2 in Table 3 below, the groups adjacent to the acryloxy and methacryloyl groups respectively represent propylene groups (groups in which the methyl group is replaced by an ethyl group), and represent a mixture of positional isomers with different methyl positions.

[0117] [Chemical Formula 7] [Table 1] [Table 2] [Table 3] Among these, the preferred specific compound A is the specific compound (A-1) to (A-24) represented by the following formula.

[0118] [Chemical Formula 8] [Liquid Crystal Compounds] The 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.

[0119] Liquid crystal compounds are generally classified into rod-shaped and disk-shaped types based on their shape. In addition, they are classified into low-molecular-weight and high-molecular-weight types. High-molecular-weight compounds typically refer to those with a degree of polymerization of 100 or higher (Polymer Physics and Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992).

[0120] In this invention, any liquid crystal compound can be used, but rod-shaped liquid crystal compounds or disc-shaped liquid crystal compounds (disc-shaped liquid crystal compounds) are preferred. Two or more rod-shaped liquid crystal compounds, two or more disc-shaped liquid crystal compounds, or mixtures of rod-shaped and disc-shaped liquid crystal compounds can also be used.

[0121] As a rod-shaped liquid crystal compound, for example, the compound described in Japanese Patent Application Publication No. 11-513019 or in paragraphs

[0026] to

[0098] of Japanese Patent Application Publication No. 2005-289980 can be preferred. As a disc-shaped liquid crystal compound, for example, the compound described in paragraphs

[0020] to

[0067] of Japanese Patent Application Publication No. 2007-108732 or in paragraphs

[0013] to

[0108] of Japanese Patent Application Publication No. 2010-244038 can be preferred, but it is not limited to these.

[0122] In this invention, from the perspective of improving the durability of the liquid crystal curing layer, the liquid crystal compound preferably has polymerizable groups, and more preferably has two or more polymerizable groups.

[0123] Here, as a polymerizable group, it is preferable to exemplify a polymerizable group represented by any one of the above formulas (P-1) to (P-20).

[0124] Furthermore, in this invention, from the perspective of improving orientation, the liquid crystal compound is preferably a compound represented by the following formula (B).

[0125] L 1 -SP 1 -D 5 -(A 1 ) a1 -D 3 -(G 1 ) g1 -D 1 -Ar 2 -D 2 -(G 2 ) g2 -D 4 -(A 2 ) a2 -D 6 -SP 2 -L 2 (B) In equation (B) above, a1, a2, g1, and g2 independently represent 0 or 1. Among them, at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1.

[0126] Furthermore, D 1 D 2 D 3 D 4 D 5 and D 6 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0127] Furthermore, G 1 and G 2 Each can independently represent an aromatic ring with 6 to 20 carbon atoms that may have substituents or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- constituting the alicyclic hydrocarbon group can be substituted by -O-, -S- or -NH-.

[0128] And, A 1 and A 2Each can independently represent an aromatic ring with 6 to 20 carbon atoms that may have substituents or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- constituting the alicyclic hydrocarbon group can be substituted by -O-, -S- or -NH-.

[0129] Furthermore, SP 1 and SP 2 Each of these groups independently represents a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent.

[0130] Furthermore, L 1 and L 2 Each of the L groups independently represents a monovalent organic group. 1 and L 2 At least one of them represents a polymerizable group. Specifically, in Ar... 2 In the case of an aromatic ring represented by the following formula (Ar-3), L 1 and L 2 and L in the following formula (Ar-3) 3 and L 4 At least one of them represents a polymerizable group.

[0131] Furthermore, Ar 2 It represents any aromatic ring selected from the group consisting of the groups represented by the formulas (Ar-1) to (Ar-7) described below.

[0132] In the above formula (B), considering that the liquid crystal composition of the present invention can easily display a smectic liquid crystal state, a1, a2, g1 and g2 are preferably all 1.

[0133] Furthermore, considering that the durability of the liquid crystal curing layer is improved, it is preferable that a1 and a2 are both 0 and g1 and g2 are both 1.

[0134] In the above formula (B), as D 1 D 2 D 3 D 4 D 5 and D 6 The divalent linking group represented in one manner, for example, can be exemplified by B in the above formula (A). 1 E 1 and D 11 The same group as the group described in the text.

[0135] In the above formula (B), as G 1 and G 2The aromatic ring with 6 to 20 carbon atoms represented in one manner can include, for example, aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, and 1,10-phenanthroline ring; and aromatic heterocycles such as furan ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, and benzothiazole ring. Among these, a benzene ring (e.g., 1,4-phenyl ring) is preferred.

[0136] In the above formula (B), as G 1 and G 2 The alicyclic hydrocarbon group with 5 to 20 carbon atoms, represented by one of the methods, is preferably a 5-membered or 6-membered ring. Furthermore, the alicyclic hydrocarbon group can be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferred. As G... 1 and G 2 The divalent alicyclic hydrocarbon group represented can be referred to, for example, the description in paragraph

[0078] of Japanese Patent Application Publication No. 2012-21068, the contents of which are incorporated herein by reference.

[0137] In this invention, considering the improved durability of the manufactured liquid crystal curing layer, G in the above formula (B) is... 1 and G 2 Preferably, it is a cycloalkane ring.

[0138] As cycloalkane rings, examples include cyclohexane rings, cycloheptane rings, cyclooctane rings, cyclododecane rings, and cyclododecane rings.

[0139] Among these, cyclohexane ring is preferred, 1,4-cyclohexene ring is more preferred, and trans-1,4-cyclohexene ring is even more preferred.

[0140] Furthermore, in equation (B) above, regarding G... 1 and G 2 The substituents that can be present as aromatic rings with 6 to 20 carbon atoms or divalent alicyclic hydrocarbon groups with 5 to 20 carbon atoms are examples of substituents described in substituent group A above, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy or halogen atoms are preferred.

[0141] In the above formula (B), as A 1 and A 2 Aromatic rings with 6 to 20 or more carbon atoms, as shown in one manner, can be exemplified by G in formula (B) above. 1 and G 2 The same groups as the aromatic rings described in the text.

[0142] Furthermore, in the above formula (B), as A 1 and A 2 One way to show a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms is to exemplify the G group in formula (B) above. 1 and G2 The same group as the alicyclic hydrocarbon group described in the text.

[0143] In addition, regarding A 1 and A 2 Substituents that can be present in an aromatic ring with 6 to 20 carbon atoms or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms include those corresponding to G in formula (B) above. 1 and G 2 It can have the same substituents as the group.

[0144] In the above formula (B), as SP 1 and SP 2 The aliphatic hydrocarbon group with 1 to 20 carbon atoms represented in one manner, for example, can be exemplified by F in the above formula (A). 1 The same group as the group described in the text.

[0145] In the above formula (B), L is used as 1 and L 2 The monovalent organic group represented can be exemplified by Ar in the above formula (A). 1 The L in the above formula (Ar-3) is represented in one way. 3 and L 4 The same group as the group described in the text.

[0146] Furthermore, as L 1 and L 2 The polymeric group represented by at least one of the above formulas is preferably a polymeric group represented by any one of the above formulas (P-1) to (P-20).

[0147] In equation (B) above, as described above, Ar 2 This represents any aromatic ring selected from the group consisting of the groups represented by formulas (Ar-1) to (Ar-7) below. Furthermore, in formulas (Ar-1) to (Ar-7) below, This indicates that D in equation (B) above... 1 Or D 2 The bonding positions.

[0148] [Chemical Formula 9] Here, each symbol in the above equations (Ar-1) to (Ar-3) is respectively associated with Ar in the above equation (A). 1 The symbols in the above expressions (Ar-1) to (Ar-3) are the same.

[0149] Furthermore, Z in the above equations (Ar-4) to (Ar-7) 1 Z 2 and Z3 With Z in the above equations (Ar-1) to (Ar-3) 1 and Z 2 The same as described in the text.

[0150] Furthermore, in the above formulas (Ar-4) to (Ar-7), Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.

[0151] Furthermore, in the above formulas (Ar-4) to (Ar-7), Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms of at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.

[0152] Among them, the aromatic rings in Ax and Ay can have substituents, or Ax and Ay can be bonded to form a ring.

[0153] And Q 3 It represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms that may have substituents.

[0154] As for Ax and Ay, examples can be found in paragraphs

[0039] to

[0095] of International Publication No. 2014 / 010325.

[0155] And, as Q 3 The alkyl group representing 1 to 6 carbon atoms can specifically include, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl. As a substituent, the substituents described in the substituent group A above can be included, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms are preferred.

[0156] Examples of liquid crystal compounds include, for instance, compounds represented by general formula (1) as described in Japanese Patent Application Publication No. 2010-084032 (especially the compounds described in paragraphs

[0067] to

[0073] ), compounds represented by general formula (II) as described in Japanese Patent Application Publication No. 2016-053709 (especially the compounds described in paragraphs

[0036] to

[0043] ), compounds represented by general formula (1) as described in Japanese Patent Application Publication No. 2016-081035 (especially the compounds described in paragraphs

[0043] to

[0055] ), and compounds described in paragraphs

[0025] to

[0056] of International Publication No. 2021 / 060427.

[0157] Among these, liquid crystal compounds are preferably liquid crystal compounds represented by the following formulas (B-1) to (B-13).

[0158] [Chemical Formula 10] In this invention, considering the reason that the orientation becomes better, the content of the compound represented by the above formula (A) is preferably 18% by mass or less, more preferably 5 to 18% by mass, relative to the total mass of the compound represented by the above formula (A) and the above liquid crystal compound (especially the compound represented by the above formula (B)).

[0159] In this invention, considering the reason that the orientation is improved, regarding the structure of the compound represented by formula (A) above (specific compound A) and the compound represented by formula (B) above (liquid crystal compound), Ar in formula (A) above is preferred. 1 Ar in equation (B) above 2 They have the same structure.

[0160] In this invention, considering the reason that the orientation is improved, regarding the structure of the compound represented by formula (A) above (specific compound A) and the compound represented by formula (B) above (liquid crystal compound), G in formula (A) above is preferred. 11 G in equation (B) above 1 For the same structure, A in the above equation (A) 11 A in the above formula (B) 1 They have the same structure.

[0161] Furthermore, in this invention, considering the reason that the orientation is improved, regarding the structure of the compound represented by formula (A) above (specific compound A) and the compound represented by formula (B) above (liquid crystal compound), D in formula (A) above is preferred. 11 With D in the above formula (B) 1 For the same structure, E in equation (A) above 1 With D in the above formula (B) 3 They have the same structure.

[0162] [Other polymeric compounds] From the viewpoint of orientation temperature and solubility, the liquid crystal composition of the present invention preferably contains other polymeric compounds having one or more polymeric groups, in addition to the specific compound A and the liquid crystal compound described above.

[0163] Here, there is no particular limitation on the polymerizable groups of other polymerizable compounds, but preferably, any polymerizable group represented by any one of the above formulas (P-1) to (P-20) is mentioned.

[0164] From the perspective of further improving the durability of the formed liquid crystal cured layer, other polymeric compounds having 2 to 4 polymeric groups are preferred as other polymeric compounds, and other polymeric compounds having 2 polymeric groups are more preferred.

[0165] As other polymerizable compounds, examples can be given of compounds represented by formulas (M1), (M2), and (M3) as described in paragraphs

[0030] to

[0033] of Japanese Patent Application Publication No. 2014-077068, and more specifically, examples can be given of specific examples described in paragraphs

[0046] to

[0055] of Japanese Patent Application Publication No. 2014-077068.

[0166] [Polymerization initiator] Preferably, the liquid crystal composition of the present invention contains a polymerization initiator.

[0167] Preferably, the polymerization initiator used is a photopolymerization initiator that can initiate a polymerization reaction by ultraviolet irradiation.

[0168] Examples of photopolymerization initiators include, for example, α-carbonyl compounds (described in U.S. Patent Nos. 2,367,661 and 2,367,670), azobin ethers (described in U.S. Patent No. 2,448,828), α-hydrocarbon-substituted aromatic azobin compounds (described in U.S. Patent No. 2,722,512), polynuclear quinone compounds (described in U.S. Patent Nos. 3,046,127 and 2,951,758), triarylimidazolium dimers, and p-aminophenyl ketone. Combinations of these compounds (described in U.S. Patent No. 3,549,367), acridine and phenazine compounds (described in Japanese Patent Application Publication No. 60-105,667 and U.S. Patent No. 4,239,850), oxadiazole compounds (described in U.S. Patent No. 4,212,970), acylphosphine oxide compounds (described in Japanese Patent Application Publication No. 63-40,799, Japanese Patent Application Publication No. 5-29,234, Japanese Patent Application Publication No. 10-95,788 and Japanese Patent Application Publication No. 10-29,997), etc.

[0169] Furthermore, in this invention, the polymerization initiator is preferably an oxime-type polymerization initiator. As a specific example, the initiator described in paragraphs

[0049] to

[0052] of International Publication No. 2017 / 170443 can be cited.

[0170] [Solvent] From the viewpoint of operability in forming a liquid crystal cured layer, the liquid crystal composition of the present invention preferably contains a solvent.

[0171] As solvents, specifically, examples 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 acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosols (e.g., methyl cellosol, ethyl cellosol, etc.), cellosol acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), and amides (e.g., dimethylformamide, dimethylacetamide, etc.). One of these solvents can be used alone, or two or more can be used simultaneously.

[0172] [Leveling agent] From the viewpoint of easy orientation control, the liquid crystal composition of the present invention preferably contains a leveling agent.

[0173] As such leveling agents, fluorinated or silicone leveling agents are preferred for their high leveling effect relative to the amount added, and fluorinated leveling agents are more preferred from the viewpoint that they are less likely to cause exudation (frost, leakage).

[0174] As leveling agents, specifically, examples include, for instance, the compounds described in paragraphs

[0079] to

[0102] of Japanese Patent Application Publication No. 2007-069471, the compounds represented by general formula (I) described in Japanese Patent Application Publication No. 2013-047204 (especially, the compounds described in paragraphs

[0020] to

[0032] ), and the compounds represented by general formula (I) described in Japanese Patent Application Publication No. 2012-211306 (especially, the compounds described in paragraphs

[0022] to

[0032] ). The compounds described in paragraph 029), liquid crystal alignment promoters represented by general formula (I) as described in Japanese Patent Application Publication No. 2002-129162 (especially the compounds described in paragraphs

[0076] to

[0078] and

[0082] to

[0084] ), and compounds represented by general formulas (I), (II) and (III) as described in Japanese Patent Application Publication No. 2005-099248 (especially the compounds described in paragraphs

[0092] to

[0096] ), etc. Furthermore, they can also function as alignment control agents as described later.

[0175] [Orientation control agent] Depending on the requirements, the liquid crystal composition of the present invention may contain an orientation control agent.

[0176] Orientation control agents can be used to form various orientation states, including vertical orientation, tilted orientation, mixed orientation, and cholesterol orientation, in addition to uniform orientation. Furthermore, specific orientation states can be controlled and achieved more uniformly and precisely.

[0177] As orientation control agents that promote uniform orientation, for example, low-molecular-weight or high-molecular-weight orientation control agents can be used.

[0178] As a low-molecular-weight orientation control agent, reference can be made to paragraphs

[0009] to

[0083] of Japanese Patent Application Publication No. 2002-20363, paragraphs

[0111] to

[0120] of Japanese Patent Application Publication No. 2006-106662, and paragraphs

[0021] to

[0029] of Japanese Patent Application Publication No. 2012-211306, the contents of which are incorporated herein by reference.

[0179] Furthermore, as an orientation control agent for polymers, reference can be made to paragraphs

[0021] to

[0057] of Japanese Patent Application Publication No. 2004-198511 and paragraphs

[0121] to

[0167] of Japanese Patent Application Publication No. 2006-106662, the contents of which are incorporated herein by reference.

[0180] Furthermore, as orientation control agents that form or promote vertical orientation, examples include boric acid compounds and onium salt compounds. Specifically, reference can be made to compounds described in Japanese Patent Application Publication No. 2008-225281, paragraphs

[0023] to

[0032] , Japanese Patent Application Publication No. 2012-208397, paragraphs

[0052] to

[0058] , Japanese Patent Application Publication No. 2008-026730, paragraphs

[0024] to

[0055] , and Japanese Patent Application Publication No. 2016-193869, paragraphs

[0043] to

[0055] , which are incorporated herein by reference.

[0181] On the other hand, regarding cholesterol orientation, it can be achieved by adding a chiral agent to the polymerizable liquid crystal composition of the present invention, and the rotation direction of cholesterol orientation can be controlled according to the chiral direction.

[0182] In addition, the spacing of cholesterol orientation can be controlled based on the orientation constraint force of the chiral reagent.

[0183] The content of the orientation control agent is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, relative to the total solid content in the composition. If the content is within this range, a uniform and highly transparent cured product can be obtained that achieves the desired orientation state and is free from precipitation, phase separation, orientation defects, etc.

[0184] [Other ingredients] The liquid crystal composition of the present invention may also contain components other than those described above, such as surfactants, tilt angle control agents, orientation aids, plasticizers, and crosslinking agents.

[0185] [Monofunctional Monomer] The monofunctional monomer of the present invention is a compound represented by the above formula (A) (specific compound A).

[0186] [Liquid Crystal Curing Layer] The liquid crystal curing layer of the present invention is a liquid crystal curing layer formed by fixing the orientation state of the liquid crystal composition of the present invention as described above.

[0187] As a method for forming a liquid crystal curable layer, for example, a method in which the liquid crystal composition of the present invention described above is used to form a desired orientation state, and then the mixture is immobilized by polymerization.

[0188] Here, the polymerization conditions are not particularly limited, but in polymerization utilizing light irradiation, ultraviolet light is preferred. The irradiation dose is preferably 10 mJ / cm². 2 ~50J / cm 2 More preferably 20 mJ / cm 2 ~5J / cm 2 Further preferred is 30 mJ / cm 2 ~3J / cm 2 Especially preferred is 50mJ / cm 2 ~1000mJ / cm 2 Furthermore, to promote the polymerization reaction, it can be carried out under heating conditions.

[0189] In addition, the liquid crystal curing layer can be formed on any support or alignment film in the optical film described later, or on the polarizer in the polarizer described later.

[0190] The orientation state of the liquid crystal compound in the liquid crystal curing layer of the present invention can be any of the following states: horizontal orientation, vertical orientation, tilted orientation, and twisted orientation. It is preferred to fix it in a state of horizontal orientation relative to the main surface of the liquid crystal curing layer.

[0191] In this specification, "horizontal alignment" means that the main surface of the liquid crystal curing layer (or, in the case where the liquid crystal curing layer is formed on a support or alignment film, the surface of that component) is parallel to the long axis of the liquid crystal compound. However, strict parallelism is not required; in this specification, it refers to an alignment where the angle between the long axis of the liquid crystal compound and the main surface of the liquid crystal curing layer is less than 10°.

[0192] In the liquid crystal curing layer, the angle between the long axis of the liquid crystal compound and the main surface of the liquid crystal curing layer is preferably 0 to 5°, more preferably 0 to 3°, and even more preferably 0 to 2°.

[0193] The liquid crystal curing 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.

[0194] The positive A plate and the positive C plate are defined as follows.

[0195] When the refractive index along the slow axis (the direction with the highest refractive index in the plane) is set as nx, the refractive index along the direction orthogonal to the slow axis in the plane is set as ny, and the refractive index along the thickness direction is set as nz, the positive A plate satisfies equation (A1), and the positive C plate satisfies equation (C1). Furthermore, the positive A plate represents a positive Rth value, and the positive C plate represents a negative Rth value.

[0196] Equation (A1) nx>ny≈nz Equation (C1) nz>nx≈ny Furthermore, the above "≈" includes not only cases where the two are exactly the same, but also cases where the two are substantially the same.

[0197] Regarding the phrase "substantially identical," in the positive A-plate, for example, the case where (ny-nz)×d (where d is the film thickness) is -10 to 10 nm, preferably -5 to 5 nm, is also included in "ny≈nz," and the case where (nx-nz)×d is -10 to 10 nm, preferably -5 to 5 nm, is also included in "nx≈nz." Furthermore, in the positive C-plate, for example, the case where (nx-ny)×d (where d is the film thickness) is 0 to 10 nm, preferably 0 to 5 nm, is also included in "nx≈ny."

[0198] When the liquid crystal curing layer of the present invention is a positive A plate, from the viewpoint of functioning as a λ / 4 plate, Re (550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, even more preferably 130 to 150 nm, and especially preferably 130 to 145 nm.

[0199] The term "λ / 4 plate" refers to a plate with λ / 4 functionality, specifically a plate that can convert linearly polarized light of a specific wavelength into circularly polarized light (or vice versa).

[0200] In the case where the liquid crystal composition of the present invention contains a dichroic substance, the liquid crystal cured layer of the present invention can be used as a polarizer (light-absorbing anisotropic film).

[0201] [Optical film] The optical film of the present invention is an optical film having the liquid crystal curing layer of the present invention.

[0202] refer to Figure 1 The structure of the optical film is explained. Figure 1 This is a schematic cross-sectional view showing an example of an optical film.

[0203] in addition, Figure 1 For illustrative purposes only; the thickness and positional relationships of the layers may not necessarily match reality. Figure 1 The support and orientation film shown are arbitrary components.

[0204] Figure 1 The optical film 10 shown has a support 16, an alignment film 14 and a cured liquid crystal composition of the present invention, namely a liquid crystal cured layer 12.

[0205] Furthermore, the liquid crystal curing layer 12 can be a stack of two or more different liquid crystal curing layers. For example, when the polarizer of the present invention described later is used as a circular polarizer, or when the optical film of the present invention is used as an optical compensation film for a liquid crystal display device using IPS (In-Plane-Switching) or FFS (Fringe-Field-Switching) technology, a stack of positive A plate and positive C plate is preferred.

[0206] Furthermore, the liquid crystal curing layer can be peeled off from the support and used separately as an optical film.

[0207] The following is a detailed description of the various components used in optical films.

[0208] [Liquid crystal curing layer] The liquid crystal curing layer of the optical film of the present invention is the liquid crystal curing layer of the present invention described above.

[0209] In the optical film, the thickness of the liquid crystal curing layer is not particularly limited, but is preferably 0.1 to 10 μm, more preferably 0.5 to 5 μm.

[0210] [Support] As described above, the optical film may have a support as a substrate for forming the liquid crystal curing layer.

[0211] This support is preferably transparent. Specifically, the light transmittance is preferably 80% or higher.

[0212] Examples of such supports include glass substrates and polymer films. Examples of polymer film materials include cellulose-based polymers; acrylic polymers such as polymethyl methacrylate and polymers containing lactone rings; thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene-based polymers such as polystyrene and acrylonitrile-styrene copolymers (AS resins); polyolefin-based polymers such as polyethylene, polypropylene, and ethylene-propylene copolymers; vinyl chloride-based polymers; amide-based polymers such as nylon and aromatic polyamides; imide-based polymers; sulfone-based polymers; polyethersulfone-based polymers; polyetheretherketone-based polymers; polyphenylene sulfide-based polymers; vinylidene chloride-based polymers; vinyl alcohol-based polymers; vinyl butyral-based polymers; aromatic ester-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; and polymers composed of mixtures of these polymers.

[0213] Furthermore, it can also serve as a support for the deflector described later.

[0214] There is no particular limitation on the thickness of the aforementioned support, but it is preferred to be 5 to 60 μm, and more preferably 5 to 40 μm.

[0215] [Orientation film] In optical films, the liquid crystal curing layer is preferably formed on the surface of the alignment film (especially the photoalignment film described later). When the optical film has any of the aforementioned supports, the alignment film can be sandwiched between the support and the liquid crystal curing layer. Furthermore, the aforementioned support can also serve as the alignment film.

[0216] The alignment film can be any film as long as it has the function of horizontally aligning the polymeric liquid crystal compound contained in the composition.

[0217] Alignment films typically use polymers as the main component. Polymer materials for alignment films are documented in numerous publications, and many commercially available products are readily available.

[0218] Polyvinyl alcohol, polyimide, or any derivative thereof are preferred as polymer materials for orientation films, and modified or unmodified polyvinyl alcohol is more preferred.

[0219] As an optical film, an alignment film can be described, for example, the alignment film described on page 43, line 24 to page 49, line 8 of International Publication No. 01 / 88574; the alignment film made of modified polyvinyl alcohol described in paragraphs

[0071] to

[0095] of Japanese Patent No. 3907735; and the liquid crystal alignment film formed by a liquid crystal alignment agent described in Japanese Patent Application Publication No. 2012-155308.

[0220] Since the object does not come into contact with the surface of the alignment film during the formation of the alignment film, the surface condition can be prevented from deteriorating. Therefore, photoalignment film is preferred as the alignment film.

[0221] There are no particular restrictions on the photoalignment film, but alignment films formed by polymers such as polyamide compounds and polyimide compounds as described in paragraphs

[0024] to

[0043] of International Publication No. 2005 / 096041, liquid crystal alignment films formed by liquid crystal alignment agents having photoalignment groups as described in Japanese Patent Application Publication No. 2012-155308, and products manufactured by Rolic Technologies under the trade name LPP-JP265CP, are all acceptable.

[0222] The thickness of the alignment film is not particularly limited, but from the viewpoint of forming a liquid crystal curing layer with uniform film thickness by mitigating the surface irregularities that may exist on the support, it is preferred to be 0.01 to 10 μm, more preferably 0.01 to 1 μm, and even more preferably 0.01 to 0.5 μm.

[0223] [Other liquid crystal curing layers] In optical films, the liquid crystal curing layer is preferably formed on the surface of other liquid crystal curing layers.

[0224] Here, as other liquid crystal curable layers, examples include liquid crystal curable layers formed by immobilizing the orientation state of a composition obtained by removing a specific compound A from the liquid crystal composition of the present invention described above. Specifically, examples include liquid crystal curable layers formed by immobilizing the orientation state of a composition containing the above-described liquid crystal compound, polymerization initiator, leveling agent, and solvent.

[0225] [Ultraviolet absorber] Considering the influence of external light (especially ultraviolet light), the optical film preferably contains an ultraviolet (UV) absorber.

[0226] The ultraviolet absorber can be contained in the liquid crystal curing layer or in components other than the liquid crystal curing layer constituting the optical film. For example, a support is a preferred component other than the liquid crystal curing layer.

[0227] As a UV absorber, any existing known UV absorber capable of exhibiting UV absorption properties can be used. Among such UV absorbers, benzotriazole or hydroxyphenyltriazine UV absorbers are preferred from the viewpoint of high UV absorption and obtaining UV absorption capacity (UV cutoff capacity) used in image display devices.

[0228] Furthermore, in order to expand the absorption range of ultraviolet rays, it is preferable to use two or more ultraviolet absorbers with different maximum absorption wavelengths.

[0229] As ultraviolet absorbers, examples include compounds described in paragraphs

[0258] to

[0259] of Japanese Patent Application Publication No. 2012-18395 and compounds described in paragraphs

[0055] to

[0105] of Japanese Patent Application Publication No. 2007-72163.

[0230] Furthermore, as a commercially available product, it can be used with Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479 and Tinuvin 1577 (all manufactured by BASF).

[0231] [Polarizing filter] The polarizer of the present invention has the optical film and polarizer described above.

[0232] Furthermore, when the liquid crystal curing layer of the present invention is a λ / 4 plate (positive A plate), the polarizer of the present invention can be used as a circular polarizer.

[0233] Furthermore, when the liquid crystal curing layer of the present invention is a λ / 4 plate (positive A plate), the angle between the slow axis of the λ / 4 plate and the absorption axis of the polarizer described later is preferably 30 to 60°, more preferably 40 to 50°, even more preferably 42 to 48°, and particularly preferably 45°.

[0234] Among them, the "slow axis" of the λ / 4 plate indicates the direction in which the in-plane refractive index of the λ / 4 plate is the largest, and the "absorption axis" of the polarizer indicates the direction in which the absorbance is the highest.

[0235] Furthermore, the polarizer of the present invention can also be used as an optical compensation film for liquid crystal display devices of IPS or FFS types.

[0236] When the polarizer of the present invention is used as an optical compensation film in an IPS or FFS liquid crystal display device, the liquid crystal curing layer of the present invention can be used as at least one of the positive A plate and the positive C plate in a laminate, preferably the positive A plate. In this case, it is preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer (described later) is orthogonal or parallel, and more preferably, the angle between the slow axis of the positive A plate and the absorption axis of the polarizer (described later) is 0 to 5° or 85 to 95°.

[0237] Furthermore, when the polarizer, positive C plate and positive A plate are stacked sequentially in the polarizer of the present invention, it is even more preferable that the slow axis of the positive A plate is parallel to the absorption axis of the polarizer.

[0238] Similarly, when the polarizer, positive A plate and positive C plate are stacked sequentially in the polarizer of the present invention, it is even more preferable that the slow axis of the positive A plate is orthogonal to the absorption axis of the polarizer.

[0239] When the polarizer of the present invention is used in the liquid crystal display device described later, it is preferable that the angle between the slow axis of the liquid crystal curing layer and the absorption axis of the polarizer described later is parallel or orthogonal.

[0240] Furthermore, in this specification, "parallel" means not strictly parallel and the angle between one of them and the other is less than 10°. Also, in this specification, "orthogonal" means not strictly orthogonal and the angle between one of them and the other is greater than 80° but less than 100°.

[0241] [Polarizer] Regarding the polarizer of the polarizer of the present invention, it is not particularly limited as long as it is a component that has the function of converting light into specific linearly polarized light, and conventionally known absorption polarizers and reflection polarizers can be used.

[0242] As an absorption-type polarizer, iodine-based polarizers, dye-based polarizers utilizing dichroic dyes, and polyene-based polarizers can be used. Iodine-based polarizers and dye-based polarizers include coated polarizers and stretched polarizers. Although both can be used, polarizers made by adsorbing iodine or dichroic dyes onto polyvinyl alcohol and then stretching it are preferred.

[0243] Furthermore, as a method for obtaining a polarizer by stretching and dyeing a laminated film in which a polyvinyl alcohol layer is formed on a substrate, examples include Japanese Patent No. 5048120, Japanese Patent No. 5143918, Japanese Patent No. 4691205, Japanese Patent No. 4751481, and Japanese Patent No. 4751486, and known technologies related to these polarizers can be preferred.

[0244] As a reflective polarizer, polarizers can be obtained by stacking thin films with different birefringence, wire grid polarizers, polarizers obtained by combining cholesteric liquid crystal with selective reflection region and quarter wave plate, etc.

[0245] In terms of superior adhesion, a polarizer comprising a polyvinyl alcohol-based resin (a polymer containing -CH2-CHOH- as repeating units, particularly selected from at least one of the groups consisting of polyvinyl alcohol and ethylene-vinyl alcohol copolymers) is preferred.

[0246] In this invention, the thickness of the polarizer is not particularly limited, but it is preferably 3μm to 60μm, more preferably 5μm to 30μm, and even more preferably 5μm to 15μm.

[0247] [Adhesive layer] The polarizer of the present invention may have an adhesive layer disposed between the liquid crystal curing layer and the polarizer in the optical film of the present invention.

[0248] As an adhesive layer used for laminating liquid crystal curing layers and polarizers, it may contain, for example, a substance that represents a ratio (tanδ=G” / G’) of 0.001 to 1.5 of the storage elastic modulus G’ measured using a dynamic viscoelasticity measuring device, such as an adhesive or a substance prone to creep. Examples of adhesives that can be used in this invention include, for example, polyvinyl alcohol-based adhesives, but are not limited thereto.

[0249] [Image display device] The image display device of the present invention is an image display device having the optical film or polarizer of the present invention.

[0250] There are no particular limitations on the display elements used in the image display device. Examples include liquid crystal cells, organic electroluminescent (hereinafter referred to as "EL (Electro Luminescence)") display panels, and plasma display panels. Among these, liquid crystal cells and organic EL display panels are preferred, and liquid crystal cells are more preferred.

[0251] That is, as an image display device, a liquid crystal display device that uses a liquid crystal cell as a display element or an organic EL display device that uses an organic EL display panel as a display element is preferred, and a liquid crystal display device is more preferred.

[0252] [Liquid Crystal Display Device] As an example of an image display device, a liquid crystal display device is a liquid crystal display device having the aforementioned polarizer and liquid crystal unit.

[0253] Furthermore, among the polarizers disposed on both sides of the liquid crystal cell, it is preferable to use the aforementioned polarizer as the front polarizer, and more preferably to use the aforementioned polarizer as both the front and rear polarizers.

[0254] The liquid crystal unit constituting a liquid crystal display device will now be described in detail.

[0255] <Liquid Crystal Unit> The liquid crystal cells used in the liquid crystal display device are 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 are not limited to these.

[0256] In TN-mode liquid crystal cells, the rod-shaped liquid crystal molecules are essentially horizontally oriented when no voltage is applied, and then twisted to an orientation of 60–120°. TN-mode liquid crystal cells are most commonly used in color TFT liquid crystal display devices, and are documented in several publications.

[0257] In a VA-mode liquid crystal cell, the rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied. In a VA-mode liquid crystal cell, in addition to the narrow definition of a VA-mode liquid crystal cell which has rod-shaped liquid crystal molecules substantially vertically oriented when no voltage is applied and substantially horizontally oriented when a voltage is applied (as described in Japanese Patent Application Publication No. 2-176625), there are also (2) a liquid crystal cell in which the VA mode is multi-domainized (MVA mode) in order to expand the viewing angle (as described in SID97, Digest of Tech. Papers 28 (1997) 845), (3) a liquid crystal cell in which rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied and twisted into multi-domain orientation when a voltage is applied (n-ASM mode) (as described in the proceedings of the Japan Liquid Crystal Conference 58-59 (1998)), and (4) a SURVIVAL mode liquid crystal cell (published in LCD International 98). Furthermore, the VA-mode heated liquid crystal cell can be any of PVA (Patterned Vertical Alignment), Optical Alignment, or PSA (Polymer-Sustained Alignment). Detailed information regarding these modes can be found in Japanese Patent Application Publication Nos. 2006-215326 and 2008-538819.

[0258] Regarding the IPS mode liquid crystal cell, the rod-shaped liquid crystal molecules are substantially parallel to the substrate, and the liquid crystal molecules respond planarly by applying an electric field parallel to the substrate surface. In the IPS mode, black is displayed when no electric field is applied, and the absorption axes of the upper and lower polarizers are orthogonal to each other. Methods for reducing light leakage and improving viewing angle when displaying black in the tilt direction using optical compensation sheets are disclosed in Japanese Patent Application Publications Nos. 10-54982, 11-202323, 9-292522, 11-133408, 11-305217, and 10-307291.

[0259] [Organic EL display device] Regarding an organic EL display device as an example of an image display device, for example, a configuration in which a polarizer, a λ / 4 plate (positive A plate) composed of the aforementioned liquid crystal curing layer and an organic EL display panel are sequentially arranged from the visual recognition side.

[0260] Furthermore, an organic EL display panel is a display panel made of organic EL elements formed by sandwiching an organic light-emitting layer (organic electroluminescent layer) between electrodes (between the cathode and the anode). There are no particular restrictions on the structure of an organic EL display panel, and a known structure can be used.

[0261] Example The present invention will now be described in further detail with reference to embodiments. The materials, amounts, proportions, processing contents, and processing steps shown in the following embodiments can be appropriately modified without departing from the spirit of the invention. Therefore, the scope of the present invention should not be interpreted as limited by the embodiments shown below.

[0262] [Synthesis of a specific compound (A-1)] [Compound (A-1-0)] The compound (A-1-0) was synthesized according to the synthetic method described in Japanese Patent Application Publication No. 2012-97078 by the following scheme.

[0263] [Chemical Formula 11] Next, a specific compound (A-1) was synthesized using the following scheme.

[0264] [Chemical Formula 12] Specifically, in a 1L three-necked flask, 62.5 g (0.16 mol) of carboxylic acid of formula (P-1) synthesized according to Japanese Patent Application Publication No. 2010-31223, 49.8 g (0.16 mol) of previously synthesized A-1-0, and 700 mL of chloroform (manufactured by FUJIFILM Wako PureChemical Corporation) were mixed, and 62.5 g of EDCI·HCl (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise, and the reaction was carried out at room temperature for 5 hours. After the reaction, the product was purified by silica gel column chromatography using ethyl acetate and hexane to obtain 5.0 g of A-1-0-1.

[0265] Next, 5 g (0.007 mol) of A-1-0-1, 50 mL of DMF (manufactured by FUJIFILM Wako Pure Chemical Corporation), and 6.8 g (0.021 mol) of cesium carbonate (manufactured by FUJIFILM Wako Pure Chemical Corporation) were mixed in a 100 mL three-necked flask and stirred at room temperature. Then, 2 g of iodomethane (manufactured by FUJIFILM Wako Pure Chemical Corporation) was added dropwise, and the mixture was reacted at room temperature for 24 hours. The mixture was then filtered under reduced pressure, and the filtrate was purified by silica gel column chromatography using ethyl acetate and hexane to obtain 1.5 g of the specific compound (A-1).

[0266] The following shows the results of mass spectrometry (MS) analysis of the specific compound (A-1) obtained.

[0267] m / z:725.27 (100.0%), 726.27 (46.0%), 727.27 (12.1%), 727.26 (4.5%), 728.27 (3.0%), 728.28 (1.4%) [Other specific ether compounds] Furthermore, regarding X in the above formula (A) 1 By -OR L1 The specific compound indicated was synthesized by changing the starting materials and using a synthetic method similar to that of the specific compound (A-1).

[0268] [Synthesis of a specific compound (A-3)] The following scheme was used to synthesize a specific compound (A-3).

[0269] [Chemical Formula 13] Specifically, 5 g (0.007 mol) of A-1-0-1 synthesized during the synthesis of the specific compound (A-1), 0.85 g (0.0084 mol) of triethylamine (manufactured by FUJIFILM Wako Pure Chemical Corporation), and 30 mL of tetrahydrofuran (THF) (manufactured by FUJIFILM Wako Pure Chemical Corporation) were mixed in a 200 mL three-necked flask and stirred at room temperature. Then, 0.66 g (0.0084 mol) of acetyl chloride (manufactured by FUJIFILM Wako Pure Chemical Corporation) was added dropwise, and the mixture was reacted at room temperature for 3 hours. The mixture was then separated by ethyl acetate and water, and the resulting organic layer was removed by vacuum distillation. The crude product was dissolved in 3 g of dichloromethane and purified by silica gel column chromatography using ethyl acetate and hexane to obtain 2.5 g of the specific compound (A-3).

[0270] The following shows the mass spectrometry analysis results of the specific compound (A-3).

[0271] m / z:753.26 (100.0%), 754.26 (47.0%), 755.27 (12.5%), 755.26 (5.1%), 756.27 (2.6%), 756.26 (2.2%) [Other specific ester compounds] Furthermore, regarding X in the above formula (A) 1 From -O-(C=O)-R L2 The specific compound indicated was synthesized by changing the starting materials and using a synthetic method similar to that of the specific compound (A-3).

[0272] [Example 1] A liquid crystal composition 1 with the following composition was prepared.

[0273] ------------------------------------------------------------ Liquid crystal composition 1 ------------------------------------------------------------ • 222.5 parts by weight of the following liquid crystal compound (B-1) • 47.0 parts by weight of the following specific compound (A-1) • 3.0 parts by weight of the following polymeric compound (D-1) • 1.5 parts by weight of the following polymerization initiator S1 • 0.1 parts by weight of the following leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Liquid crystal compound (B-1) [Chemical Formula 14] Specific compound (A-1) [Chemical Formula 15] Polymerizable compound (D-1) [Chemical Formula 16] Polymerization initiator S1 [Chemical Formula 17] Leveling agent P1 [In the following, a, b, and c represent the content (mass%) of each repeating unit relative to all repeating units, respectively, meaning a=44.8, b=50.3, and c=4.9.] [Chemical Formula 18] [Example 2] A liquid crystal composition 2 with the following composition was prepared.

[0274] ------------------------------------------------------------ Liquid crystal composition 2 ------------------------------------------------------------ • 222.5 parts by weight of the following liquid crystal compound (B-5) • 47.0 parts by weight of the following specific compound (A-23) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Liquid crystal compound (B-5) [Chemical Formula 19] Specific compound (A-23) [Chemical Formula 20] [Example 3] A liquid crystal composition 3 with the following composition was prepared.

[0275] ------------------------------------------------------------ Liquid crystal composition 3 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-1) • 47.0 parts by weight of the following specific compound (A-3) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-3) [Chemical Formula 21] [Example 4] A liquid crystal composition 4 with the following composition was prepared.

[0276] ------------------------------------------------------------ Liquid crystal composition 4 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-1) • 47.0 parts by weight of the following specific compound (A-2) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-2) [Chemical Formula 22] [Example 5] A liquid crystal composition 5 with the following composition was prepared.

[0277] ------------------------------------------------------------ Liquid crystal composition 5 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-1) • 47.0 parts by weight of the following specific compound (A-6) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-6) [Chemical Formula 23] [Example 6] A liquid crystal composition 6 with the following composition was prepared.

[0278] ------------------------------------------------------------ Liquid crystal composition 1 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-1) • 55.6 parts by weight of the specific compound (A-1) mentioned above • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ [Example 7] A liquid crystal composition 7 with the following composition was prepared.

[0279] ------------------------------------------------------------ Liquid crystal composition 7 ------------------------------------------------------------ • 222.5 parts by weight of the following liquid crystal compound (B-5) • 47.0 parts by weight of the specific compound (A-1) mentioned above • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Liquid crystal compound (B-5) [Chemical Formula 24] [Example 8] A liquid crystal composition 8 with the following composition was prepared.

[0280] ------------------------------------------------------------ Liquid crystal composition 8 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-1) • 47.0 parts by weight of the specific compound (A-23) mentioned above. • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ [Example 9] A liquid crystal composition 9 with the following composition was prepared.

[0281] ------------------------------------------------------------ Liquid crystal composition 9 ------------------------------------------------------------ • 222.5 parts by weight of the following liquid crystal compound (B-2) • 47.0 parts by weight of the following specific compound (A-7) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Liquid crystal compound (B-2) [Chemical Formula 25] Specific compound (A-7) [Chemical Formula 26] [Example 10] A liquid crystal composition 10 with the following composition was prepared.

[0282] ------------------------------------------------------------ Liquid crystal composition 10 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-2) • 47.0 parts by weight of the following specific compound (A-8) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-8) [Chemical Formula 27] [Example 11] A liquid crystal composition 11 with the following composition was prepared.

[0283] ------------------------------------------------------------ Liquid crystal composition 11 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-2) • 47.0 parts by weight of the following specific compound (A-9) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-9) [Chemical Formula 28] [Example 12] A liquid crystal composition 12 with the following composition was prepared.

[0284] ------------------------------------------------------------ Liquid crystal composition 12 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-2) • 47.0 parts by weight of the following specific compound (A-10) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-10) [Chemical Formula 29] [Example 13] A liquid crystal composition 13 with the following composition was prepared.

[0285] ------------------------------------------------------------ Liquid crystal composition 13 ------------------------------------------------------------ • 222.5 parts by weight of the following liquid crystal compound (B-3) • 47.0 parts by weight of the following specific compound (A-11) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Liquid crystal compound (B-3) [Chemical Formula 30] Specific compound (A-11) [Chemical Formula 31] [Example 14] A liquid crystal composition 14 with the following composition was prepared.

[0286] ------------------------------------------------------------ Liquid crystal composition 14 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-3) • 47.0 parts by weight of the following specific compound (A-12) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-12) [Chemical Formula 32] [Example 15] A liquid crystal composition 15 with the following composition was prepared.

[0287] ------------------------------------------------------------ Liquid crystal composition 15 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-3) • 47.0 parts by weight of the following specific compound (A-13) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-13) [Chemical Formula 33] [Example 16] A liquid crystal composition 16 with the following composition was prepared.

[0288] ------------------------------------------------------------ Liquid crystal composition 16 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-3) • 47.0 parts by weight of the following specific compound (A-14) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-14) [Chemical Formula 34] [Example 17] A liquid crystal composition 17 with the following composition was prepared.

[0289] ------------------------------------------------------------ Liquid crystal composition 17 ------------------------------------------------------------ • 222.5 parts by weight of the following liquid crystal compound (B-4) • 47.0 parts by weight of the following specific compound (A-16) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Liquid crystal compound (B-4) [Chemical Formula 35] Specific compound (A-16) [Chemical Formula 36] [Example 18] A liquid crystal composition 18 with the following composition was prepared.

[0290] ------------------------------------------------------------ Liquid crystal composition 18 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-4) • 47.0 parts by weight of the following specific compound (A-17) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-17) [Chemical Formula 37] [Example 19] A liquid crystal composition 19 with the following composition was prepared.

[0291] ------------------------------------------------------------ Liquid crystal composition 19 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-4) • 47.0 parts by weight of the following specific compound (A-18) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-18) [Chemical Formula 38] [Example 20] A liquid crystal composition 20 with the following composition was prepared.

[0292] ------------------------------------------------------------ Liquid crystal composition 20 ------------------------------------------------------------ • 222.5 parts by mass of the above-mentioned liquid crystal compound (B-4) • 47.0 parts by weight of the following specific compound (A-19) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Specific compound (A-19) [Chemical Formula 39] [Comparative Example 1] A liquid crystal composition C-1 with the following composition was prepared.

[0293] ------------------------------------------------------------ Liquid crystal composition C-1 ------------------------------------------------------------ • 269.5 parts by mass of the above-mentioned liquid crystal compound (B-1) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ [Comparative Example 2] A liquid crystal composition C-2 with the following composition was prepared.

[0294] ------------------------------------------------------------ Liquid crystal composition C-2 ------------------------------------------------------------ • 22.5 parts by mass of the above-mentioned liquid crystal compound (B-1) • 47.0 parts by weight of the following compound (CA-1) • 3.0 parts by weight of the above polymeric compound (D-1) • 1.5 parts by weight of the above polymerization initiator S1 • 0.1 parts by weight of the above leveling agent P1 92.5 parts by weight of cyclopentanone 64.2 parts by weight of methyl ethyl ketone ------------------------------------------------------------ Compound (CA-1) [Chemical Formula 40] [Fabrication of Optical Films] The liquid crystal composition 1 prepared in Example 1 was coated onto a glass substrate with a rub-treated polyimide alignment film (Nissan Chemical Corporation SE-150) using a spin-coating method. The coating was then aligned at 200°C to form a liquid crystal layer. The substrate was then cooled to 135°C and subjected to a process based on 1000 mJ / cm². 2 An optical film 1 for wavelength dispersion measurement was fabricated by fixing the orientation of the film by ultraviolet irradiation to form a liquid crystal curing layer.

[0295] The phase difference of optical film 1 was measured and confirmed to be Re(450) / Re(550) = 0.88.

[0296] Using the same method, liquid crystal curing layers were also formed on the liquid crystal compositions prepared in Examples 2-20 and Comparative Examples 1 and 2, and optical films were fabricated.

[0297] [Analysis] 20 μL of the prepared liquid crystal compositions 1-20, C-1, and C-2 were dropped onto a glass plate and placed at 25°C for 1 hour. The precipitation of the solid film was then observed with the naked eye. Specifically, the area of ​​the turbid portion (whitened portion) was estimated relative to the area of ​​the solid film, and the precipitation performance was judged using an index of 1-3 according to the following criteria. The results are shown in Table 4 below.

[0298] <Extraction Indicators> Extraction 1: 75% or more but less than 100% is considered whitening. Extraction 2: 25% or more but less than 75% is considered whitening. Extraction property 3: Less than 25% indicates whitening. [Orientation Evaluation] For the determination of orientation, an LED (Light Emitting Diode) light source, a lower polarizer, a liquid crystal curing layer (an optical film made of various liquid crystal compositions), and an upper polarizer were arranged sequentially on a table with all surfaces horizontal. The sample and the upper polarizer were designed to be rotatable. The brightness of the light emitted from the light source and sequentially transmitted through the lower polarizer, the sample, and the upper polarizer was measured from a vertical direction using a luminance meter (BM-5A (manufactured by TOPCON CORPORATION)).

[0299] During measurement, first, with no sample, the upper polarizer is rotated to align with the darkest position (orthogonal Nicol settings). The sample, with the protective film removed, is inserted between the polarizers, and the sample is rotated under orthogonal Nicol settings to measure the minimum brightness. Next, the upper and lower polarizers are aligned with parallel Nicol settings, the sample is rotated, and the maximum brightness is measured.

[0300] To eliminate the effect of brightness leakage caused by the upper and lower polarizers, the values ​​obtained by the following formula were evaluated according to the following evaluation criteria. The results are shown in Table 4 below.

[0301] Orientation = 1 / (Minimum brightness under orthogonal Nicol with sample set) / (Maximum brightness under parallel Nicol with sample set) - (Minimum brightness under orthogonal Nicol without sample) / (Maximum brightness under parallel Nicol without sample) (Evaluation criteria) A: The aforementioned orientation score is above 200,000. B: The aforementioned orientation score is between 100,000 and 200,000. C: The above orientation is less than 100,000 [Table 4]

[0302] As shown in Table 4 above, it can be seen that without the coordination of specific compound A, precipitation cannot be suppressed (Comparative Example 1).

[0303] Furthermore, it can be seen that when a compound that does not correspond to the compound represented by the above formula (A) is used, although precipitation is suppressed, orientation is poor (Comparative Example 2).

[0304] In contrast, it can be seen that the precipitation of liquid crystal compositions containing specific compound A and liquid crystal compounds is suppressed and the orientation becomes good (Examples 1-20).

[0305] In particular, a comparison between Example 1 and Example 6 shows that if the content of specific compound A is 18% by mass or less relative to the total mass of the specific compound and the liquid crystal compound, the orientation becomes better.

[0306] Furthermore, a comparison between Example 1 and Example 7, and between Example 2 and Example 8, reveals that regarding the structures of the compound represented by formula (A) (specific compound A) and the compound represented by formula (B) (liquid crystal compound), if Ar in formula (A) 1 Ar in equation (B) above 2 For the same structure, G in equation (A) above11 G in equation (B) above 1 For the same structure, A in the above equation (A) 11 A in the above formula (B) 1 If the structure is the same, the orientation becomes better.

[0307] Symbol Explanation 10-Optical film, 12-Liquid crystal curing layer, 14-Orientation film, 16-Support.

Claims

1. A liquid crystal composition comprising a compound represented by the following formula (A) and a liquid crystal compound, in, In the aforementioned formula (A), P 1 Indicates a polymerizable group. F 1 Indicates a spacer group, B 1 E 1 and D 11 Each can independently represent a single bond or a divalent linker. A 11 and G 11 Each of the above can independently represent a divalent aromatic hydrocarbon group with 6 to 20 carbon atoms or a divalent alicyclic hydrocarbon group with 3 to 16 carbon atoms, wherein the hydrogen atoms contained in the aromatic hydrocarbon group or the alicyclic hydrocarbon group can be independently converted by halogen atoms, -R L1 -OR L1 Cyano or nitro substitution, R L1 The alkyl group represents an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atoms contained in the alkyl group may be independently replaced by fluorine atoms, and the carbon atoms contained in the aromatic hydrocarbon group or the alicyclic hydrocarbon group may be independently replaced by oxygen atoms, sulfur atoms or nitrogen atoms. m1 and n1 independently represent integers from 0 to 3. When m1 is 2 or 3, multiple B 1 Multiple A's can be the same or different. 11 They can be the same or different. When n1 is 2 or 3, multiple E 1 They can be the same or different, multiple Gs 11 They can be the same or different. X 1 Indicates -OR L2 -O-(C=O)-R L3 -O-(C=O)-OR L4 -O-(C=O)-NH-R L5 -O-(C=O)-NR L6 -R L7 Or -O-(C=S)-R L8 R L2 R represents an alkyl, acryloyl, or methacryloyl group having 1 to 4 carbon atoms. L3 R represents an alkyl group having 1 to 4 carbon atoms. L4 ~R L8 Each can be independently represented as an acyclic alkyl group, a monovalent aromatic group, or a monovalent alicyclic group. Ar 1 This represents any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-3). Among them, in the formulas (Ar-1) to (Ar-3), Indicates D 11 or X 1 The bonding position, Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 and Z 2 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Represent the selection independently of -O- and -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, wherein the nonmetallic atom may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of these represents a monovalent organic group independently.

2. The liquid crystal composition according to claim 1, wherein, The liquid crystal compound is a compound represented by the following formula (B). L 1 -SP 1 -D 5 -(A 1 ) a1 -D 3 -(G 1 ) g1 -D 1 -Ar 2 -D 2 -(G 2 ) g2 -D 4 -(A 2 ) a2 -D 6 -SP 2 -L 2 (B) In equation (B), a1, a2, g1, and g2 each independently represent 0 or 1, wherein 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 can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. G 1 and G 2 Each of these groups independently represents an aromatic ring with 6 to 20 carbon atoms that may have substituents, or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-. A 1 and A 2 Each of these groups independently represents an aromatic ring with 6 to 20 carbon atoms that may have substituents, or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-. SP 1 and SP 2 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 1 and L 2 Each of the L groups independently represents a monovalent organic group. 1 and L 2 At least one of them represents a polymerizable group, wherein, in Ar 2 In the case of an aromatic ring represented by the following formula (Ar-3), L 1 and L 2 and L in the following formula (Ar-3) 3 and L 4 At least one of them represents a polymerizable group. Ar 2 This represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (Ar-1) to (Ar-7). Among them, in the formulas (Ar-1) to (Ar-7), Indicates D 1 Or D 2 The bonding position, Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 Z 2 and Z 3 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Represent the selection independently of -O- and -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, wherein the nonmetallic atom may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of the L groups independently represents a monovalent organic group. 3 and L 4 and L in equation (B) 1 and L 2 At least one of them represents a polymerizable group. Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms of at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic rings in Ax and Ay can have substituents, or Ax and Ay can be bonded together to form a ring. Q 3 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms that may have substituents.

3. The liquid crystal composition according to claim 2, wherein, The content of the compound represented by formula (A) is 18% by mass or less relative to the total mass of the compound represented by formula (A) and the liquid crystal compound.

4. The liquid crystal composition according to any one of claims 1 to 3, wherein, Ar in formula (A) 1 It is an aromatic ring represented by the formula (Ar-1) or (Ar-2).

5. The liquid crystal composition according to claim 2 or 3, wherein, Ar in formula (A) 1 Ar in equation (B) 2 They have the same structure.

6. The liquid crystal composition according to claim 2 or 3, wherein, G in equation (A) 11 With G in equation (B) 1 For the same structure, In the formula (A) 11 With A in the above formula (B) 1 They have the same structure.

7. A monofunctional monomer, represented by the following formula (A), in, In the aforementioned formula (A), P 1 Indicates a polymerizable group. F 1 Indicates a spacer group, B 1 E 1 and D 11 Each can independently represent a single bond or a divalent linker. A 11 and G 11 Each of the above can independently represent a divalent aromatic hydrocarbon group with 6 to 20 carbon atoms or a divalent alicyclic hydrocarbon group with 3 to 16 carbon atoms, wherein the hydrogen atoms contained in the aromatic hydrocarbon group or the alicyclic hydrocarbon group can be independently converted by halogen atoms, -R L1 -OR L1 Cyano or nitro substitution, R L1 The alkyl group represents an alkyl group having 1 to 4 carbon atoms, wherein the hydrogen atoms contained in the alkyl group may be independently replaced by fluorine atoms, and the carbon atoms contained in the aromatic hydrocarbon group or the alicyclic hydrocarbon group may be independently replaced by oxygen atoms, sulfur atoms or nitrogen atoms. m1 and n1 independently represent integers from 0 to 3. When m1 is 2 or 3, multiple B 1 Multiple A's can be the same or different. 11 They can be the same or different. When n1 is 2 or 3, multiple E 1 They can be the same or different, multiple Gs 11 They can be the same or different. X 1 Indicates -OR L2 -O-(C=O)-R L3 -O-(C=O)-OR L4 -O-(C=O)-NH-R L5 -O-(C=O)-NR L6 -R L7 Or -O-(C=S)-R L8 R L2 R represents an alkyl, acryloyl, or methacryloyl group having 1 to 4 carbon atoms. L3 R represents an alkyl group having 1 to 4 carbon atoms. L4 ~R L8 Each can be independently represented as an acyclic alkyl group, a monovalent aromatic group, or a monovalent alicyclic group. Ar 1 This represents any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-3). Among them, in the formulas (Ar-1) to (Ar-7), Indicates D 11 or X 1 The bonding position, Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 Z 2 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Represent the selection independently of -O- and -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, wherein the nonmetallic atom may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of these represents a monovalent organic group independently.

8. A liquid crystal curing layer formed by immobilizing the orientation state of the liquid crystal composition according to any one of claims 1 to 3.

9. An optical film having the liquid crystal curing layer of claim 8.

10. A polarizer having the optical film and polarizer of claim 9.

11. An image display device having the optical film of claim 9.

Images