Liquid crystal composition, compound, optically anisotropic film, optical film, polarizing plate, and image display device
By using the liquid crystal compound with a specific compound, the specific compound contains an aromatic ring with a very absorbing wavelength in the range of 280 to 420 nm, solving the problem of optical anisotropic film orientation defects, and achieving the effect of improving the film's light resistance and stability.
Patent Information
- Application Number
- CN202180063766.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-09-18
- Filing Date
- 2021-08-30
- Publication Date
- 2025-06-17
- Estimated Expiration
- 2041-08-30
AI Technical Summary
The conventional polymerizable liquid crystal compositions are prone to orientation defects when forming an optically anisotropic film, which affects the performance of the film.
By using the liquid crystal compound with a specific compound, the specific compound contains an aromatic ring with a very absorbing wavelength in the range of 280 to 420 nm, which can suppress the orientation defect of the optical anisotropic film.
The orientation defects in the optical anisotropic film are effectively suppressed, and the light resistance and stability of the film are improved.
Smart Images

Figure CN116249757B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to a liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device. Background Art
[0002] Regarding polymerizable liquid crystal compounds exhibiting reverse wavelength dispersion, since they have characteristics such as being able to accurately convert the light wavelength over a wide wavelength range and being able to thin the retardation film (optically anisotropic film) to have a high refractive index, they have been actively studied.
[0003] Moreover, as polymerizable compounds exhibiting reverse wavelength dispersion, the T-type molecular design guidelines are generally adopted, requiring the wavelength of the molecular major axis to be shortened and the wavelength of the minor axis located at the center of the molecule to be lengthened.
[0004] For example, Patent Document 1 describes a polymerizable liquid crystal compound represented by the following formula (1) ([Claim 1]).
[0005]
[0006] Prior Art Documents
[0007] Patent Documents
[0008] Patent Document 1: International Publication No. 2019 / 017445 Summary of the Invention
[0009] Technical Problem to be Solved by the Invention
[0010] As a result of the present inventors' research on the polymerizable liquid crystal compound described in Patent Document 1, it was clarified that orientation defects sometimes occur in the optically anisotropic film formed according to the other components of the polymerizable liquid crystal composition containing the polymerizable liquid crystal compound.
[0011] Therefore, an object of the present invention is to provide a liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device capable of suppressing the generation of orientation defects in the optically anisotropic film.
[0012] Means for Solving the Technical Problem
[0013] As a result of the present inventors' intensive research to achieve the above object, it was found that when a liquid crystal composition containing a compound represented by the following formula (II) is used together with a liquid crystal compound, the orientation defects of the formed optically anisotropic film can be suppressed, and thus the present invention was completed.
[0014] That is, it was found that the above object can be achieved by the following configuration.
[0015] [1] A liquid crystal composition containing a liquid crystal compound and a compound represented by the following formula (II).
[0016] [2] The liquid crystal composition according to [1], wherein
[0017] at least one M in the following formula (II) represents an aromatic ring having a maximum absorption wavelength in the range of 280 to 420 nm.
[0018] [3] The liquid crystal composition according to [1] or [2], wherein
[0019] at least one M in the following formula (II) represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (M-1) to (M-7).
[0020] [4] The liquid crystal composition according to any one of [1] to [3], wherein
[0021] T in the following formula (II) represents a polymerizable group.
[0022] [5] The liquid crystal composition according to any one of [1] to [4], wherein
[0023] T in the following formula (II) represents any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20).
[0024] [6] The liquid crystal composition according to any one of [1] to [5], wherein
[0025] the liquid crystal compound has reverse wavelength dispersion.
[0026] [7] The liquid crystal composition according to any one of [1] to [6], wherein
[0027] the liquid crystal compound is a compound of any aromatic ring selected from the group consisting of the groups represented by the following formulas (Ar-1) to (Ar-7).
[0028] [8] The liquid crystal composition according to any one of [1] to [7], wherein
[0029] the liquid crystal compound has a polymerizable group.
[0030] [9] The liquid crystal composition according to [8], wherein
[0031] the polymerizable group represents any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20).
[0032]
[10] A compound represented by the following formula (II).
[0033]
[11] The compound according to
[10] , wherein
[0034] at least one M in the following formula (II) represents an aromatic ring having a maximum absorption wavelength in the range of 280 to 420 nm.
[0035]
[12] The compound according to
[10] or
[11] , wherein
[0036] at least one M in the following formula (II) represents an arbitrary aromatic ring selected from the group consisting of the groups represented by the following formulas (M-1) to (M-7).
[0037]
[13] The compound according to any one of
[10] to
[12] , wherein
[0038] T in the following formula (II) represents a polymerizable group.
[0039]
[14] The compound according to any one of
[10] to
[13] , wherein
[0040] T in the following formula (II) represents an arbitrary polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20).
[0041]
[15] An optically anisotropic film obtained by polymerizing the liquid crystal composition according to any one of [1] to [9].
[0042]
[16] The optically anisotropic film according to
[15] , which satisfies the following formula (III).
[0043]
[17] An optical film having the optically anisotropic film according to
[15] or
[16] .
[0044]
[18] A polarizing plate having the optical film according to
[17] and a polarizer.
[0045]
[19] An image display device having the optical film according to
[17] or the polarizing plate according to
[18] .
[0046] Advantages of the Invention
[0047] According to the present invention, it is possible to provide a liquid crystal composition, a compound, an optically anisotropic film, an optical film, a polarizing plate, and an image display device that can suppress the generation of alignment defects in the optically anisotropic film. Brief Description of the Drawings
[0048] Figure 1 A is a schematic cross-sectional view showing an example of the optical film of the present invention.
[0049] Figure 1B is a schematic cross-sectional view showing an example of the optical film of the present invention.
[0050] Figure 1 C is a schematic cross-sectional view showing an example of the optical film of the present invention. Detailed Description
[0051] Hereinafter, the present invention will be described in detail.
[0052] The description of the constituent elements described below is sometimes based on representative embodiments of the present invention, but the present invention is not limited to such embodiments.
[0053] In addition, in this specification, the numerical range represented by "~" means a range including the numerical values described before and after "~" as the lower limit value and the upper limit value.
[0054] Furthermore, in this specification, regarding each component, one substance corresponding to each component can be used alone, or two or more can be used simultaneously. Here, in the case of using two or more substances for each component, unless otherwise specified, the content of the component represents the total content of the substances used simultaneously.
[0055] Moreover, in this specification, unless the bonding position is specified, the bonding direction of the divalent group (for example, -CO-NR-) marked has no particular limitation. For example, in D in the following formula (I) 1 when it is -CO-NR-, if the position bonded to the G 1 side is set as *1, and the position bonded to the Ar 1 side is set as *2, then D 1 can be *1-CO-NR-*2 or *1-NR-CO-*2.
[0056] [Polymerizable Liquid Crystal Composition]
[0057] The liquid crystal composition of the present invention is a liquid crystal composition containing a liquid crystal compound and a compound represented by the following formula (II) (hereinafter, also simply referred to as "specific compound").
[0058] In the present invention, as described above, by using a liquid crystal composition in which a specific compound is blended with a liquid crystal compound, it is possible to suppress orientation defects in the formed optically anisotropic film.
[0059] Although the detailed content is not clear, the present inventors presume as follows.
[0060] That is, it is considered that due to the presence of amino groups contained in a specific compound, bonds (such as ester bonds) contained in the liquid crystal compound are cleaved, and the crystallinity of the liquid crystal compound is reduced, so that the generation of alignment defects caused by crystallization of the liquid crystal compound can be suppressed. Further, it is also considered that by incorporating a specific compound, the phase transition temperature of the liquid crystal composition is lowered, thereby suppressing the generation of alignment defects caused by crystallization of the liquid crystal compound.
[0061] Hereinafter, each component of the liquid crystal composition of the present invention will be described in detail.
[0062] 〔Specific compound〕
[0063] The specific compound contained in the liquid crystal composition of the present invention is a compound represented by the following formula (II).
[0064] [Chemical formula 1]
[0065]
[0066] In the above formula (II), R 21 and R 22 each independently represents a hydrogen atom or an alkyl group.
[0067] Further, in the above formula (II), R 23 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
[0068] Further, in the above formula (II), SP 21 and Sp 22 each independently represents a single bond or an alkylene group. Among them, the hydrogen atoms contained in the alkylene group may be substituted with a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothio group, a cyano group, a nitro group, an isocyano group, an isothiocyanato group or an alkyl group having 1 to 20 carbon atoms. Further, in -CH2- constituting the alkylene group, one or more non-adjacent -CH2- may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR 24 -, -NH-CO-, -NR 25 -CO-, -NH-, -NR 26 - or -C≡C-, and R 24 to R 26 represent substituents.
[0069] Further, in the above formula (II), D 21 and D 22 each independently represents a single bond, or -CO-, -O-, -S-, -C(=S)-, -CR 27 R 28 -, -CR29 =CR 30 -, -NH-, -NR 31 -, or a divalent linking group containing two or more of them in combination, R 27 ~R 31 represents a substituent.
[0070] And in the above formula (II), M represents an aromatic ring, an alicyclic ring or a heterocyclic ring which may have substituents.
[0071] And in the above formula (II), m represents an integer of 3 or more, and a plurality of Ms may be the same or different, and a plurality of Ds 22 may be the same or different.
[0072] And in the above formula (II), T represents a hydrogen atom, an alkyl group or a polymerizable group.
[0073] Here, as R 24 ~R 31 The substituents represented (hereinafter, also simply referred to as "substituent X".) include, for example, an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group, an alkenyl group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group and an N-alkylcarbamate group, etc. Among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group or a halogen atom is preferred.
[0074] As the alkyl group, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms is preferred, and an alkyl group having 1 to 8 carbon atoms is more preferred (for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and cyclohexyl, etc.), an alkyl group having 1 to 4 carbon atoms is further preferred, and methyl or ethyl is particularly preferred.
[0075] As the alkoxy group, an alkoxy group having 1 to 18 carbon atoms is preferred, and an alkoxy group having 1 to 8 carbon atoms is more preferred (for example, methoxy, ethoxy, n-butoxy and methoxyethoxy, etc.), an alkoxy group having 1 to 4 carbon atoms is further preferred, and methoxy or ethoxy is particularly preferred.
[0076] As the alkoxycarbonyl group, a group in which an oxycarbonyl (-O-CO-) group is bonded to the above-exemplified alkyl group can be mentioned. Among them, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl or isopropoxycarbonyl is preferred, and methoxycarbonyl is more preferred.
[0077] As the alkylcarbonyloxy group, a group in which a carbonyloxy (-CO-O-) group is bonded to the above-exemplified alkyl group can be mentioned. Among them, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy or isopropylcarbonyloxy is preferred, and methylcarbonyloxy is more preferred.
[0078] As the halogen atom, for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. may be mentioned, and among them, a fluorine atom or a chlorine atom is preferred.
[0079] In the above formula (II), as R 21 and R 22 The alkyl group shown as one of them may be, for example, the same group as the alkyl group exemplified in the above substituent X.
[0080] And, as R 21 and R 22 preferably represents a methyl group.
[0081] In the above formula (II), as described above, R 23 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group, but preferably represents a hydrogen atom.
[0082] In the above formula (II), as SP 21 and SP 22 The alkylene group shown as one of them may be, for example, a linear or branched alkylene group having 1 to 12 carbon atoms. Specifically, a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group, a heptylene group may be mentioned.
[0083] Here, regarding the alkylene group shown as one of SP 21 and SP 22 As described above, the hydrogen atom contained in the alkylene group may be substituted with a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorothioalkyl group, a cyano group, a nitro group, an isocyano group, an isothiocyanato group or an alkyl group having 1 to 20 carbon atoms.
[0084] And, regarding the alkylene group shown as one of SP 21 and Sp 22 As described above, in the -CH2- constituting the alkylene group, one or two or more non-adjacent -CH2- may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR 24 -, -NH-CO-, -NR 25 -CO-, -NH-, -NR 26 - or -C≡C-.
[0085] And, as SP 21 and SP 22, preferably represents a linear alkylene group having 2 to 10 carbon atoms or a divalent linking group in which one or more non-adjacent -CH2- groups constituting a linear alkylene group having 2 to 12 carbon atoms are replaced by -O-, -COO- or -OCO-, more preferably represents a linear alkylene group having 2 to 8 carbon atoms or a divalent linking group in which one or more non-adjacent -CH2- groups among the -CH2- groups constituting a linear alkylene group having 2 to 8 carbon atoms are replaced by -O-.
[0086] In the above formula (II), as D 21 and D 22 The divalent linking group represented by one of the modes, for example, can be -CO-, -O-, -CO-O-, -C(=S)O-, -CR 1 R 2 -, -CR 1 R 2 -CR 1 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 independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 12 carbon atoms.
[0087] And, as D 21 and D 22 , preferably represents a single bond, -CO-, -O- or -CO-O-.
[0088] In the above formula (II), as one form of M, the aromatic ring may be, for example, an aromatic ring having 6 to 20 carbon atoms. Specifically, examples include aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, and phenanthroline ring; aromatic heterocycles such as furan ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, and benzothiazole ring; and groups represented by the following formulas (M-1) to (M-8) described later.
[0089] Further, as one form of M, the alicyclic ring may be, for example, a cycloalkane ring. Specifically, examples include cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclododecane ring, cyclodocosane ring, and the like.
[0090] Further, as one form of M, the heterocyclic ring may be a heterocyclic ring other than the above aromatic heterocycles. Specifically, examples include tetrahydrofuran ring, tetrahydropyran ring, pyrrolidine ring, piperidine ring, tetrahydrothiophene ring, and the like.
[0091] Examples of the substituent that M may have include the same groups as the above substituent X.
[0092] In the present invention, in consideration of the better light resistance of the formed optically anisotropic film, at least one M in the above formula (II) preferably represents an aromatic ring having a maximum absorption wavelength in the range of 280 to 420 nm. In particular, when there are an odd number (for example, 3 or 5) of M, the central M preferably represents an aromatic ring having a maximum absorption wavelength in the range of 280 to 420 nm.
[0093] Further, in the present invention, in consideration of the good compatibility with the liquid crystal compound, at least one M in the above formula (II) preferably represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (M-1) to (M-7). In particular, when there are an odd number (for example, 3 or 5) of M, the central M preferably represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (M-1) to (M-7).
[0094] [Chemical formula 2]
[0095]
[0096] In the above formulas (M-1) to (M-7), * represents the bonding position to D 21 or D 22 .
[0097] Further, in the above formula (M-1), Q 1 represents N or CH, Q 2 represents -S-, -O- or -N(R 6 )-, R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Y1 Represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have substituents, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have substituents, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have substituents, and one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted by -O-, -S-, or -NH-.
[0098] Here, as R 6 The alkyl group having 1 to 6 carbon atoms represented, specifically, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl can be cited.
[0099] And, as Y 1 The aromatic hydrocarbon group having 6 to 12 carbon atoms represented, for example, aryl groups such as phenyl, 2,6-diethylphenyl, and naphthyl can be cited.
[0100] As Y 1 The aromatic heterocyclic group having 3 to 12 carbon atoms represented, for example, heteroaryl groups such as thiophenyl, thiazolyl, furyl, and pyridyl can be cited.
[0101] As Y 1 The alicyclic hydrocarbon group having 6 to 20 carbon atoms represented, for example, cyclohexylene, cyclopentylene, norbornenyl, adamantylene, etc. can be cited.
[0102] As Y 1 The substituents that can be had, for example, the same groups as the above-mentioned substituent X can be cited.
[0103] And, in the above formulas (M-1) to (M-7), Z 1 , Z 2 And Z 3 Each independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 , or -COR 12 , R 7 To R 12 Each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 And Z 2 May bond to each other to form an aromatic ring.
[0104] Here, as the monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 15 carbon atoms is preferred, and an alkyl group having 1 to 8 carbon atoms is more preferred. Specifically, methyl, ethyl, isopropyl, tert-pentyl (1,1-dimethylpropyl), tert-butyl, 1,1-dimethyl-3,3-dimethyl-butyl are further preferred, and methyl, ethyl, and tert-butyl are particularly preferred.
[0105] As the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, for example, monocyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, methylcyclohexyl, and ethylcyclohexyl can be mentioned; monocyclic unsaturated hydrocarbon groups such as cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, cyclopentadienyl, cyclohexadienyl, cyclooctadienyl, and cyclodecadienyl; bicyclic [2.2.1] heptyl, bicyclic [2.2.2] octyl, tricyclic [5.2.1.0 2,6 decyl, tricyclic [3.3.1.1 3,7 decyl, tetracyclic [6.2.1.1 3,6 .0 2,7 dodecyl, adamantyl and other polycyclic saturated hydrocarbon groups, etc.
[0106] As the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, specifically, for example, phenyl, 2,6-diethylphenyl, naphthyl, biphenyl, etc. can be mentioned, and an aryl group having 6 to 12 carbon atoms (especially, phenyl) is preferred.
[0107] As the monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, specifically, for example, 4-pyridyl, 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, etc. can be mentioned.
[0108] As the halogen atom, for example, fluorine atom, chlorine atom, bromine atom, iodine atom, etc. can be mentioned, and among them, fluorine atom, chlorine atom, bromine atom are preferred.
[0109] On the other hand, as the alkyl group having 1 to 6 carbon atoms represented by R 7 ~R 10 specifically, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, etc. can be mentioned.
[0110] And, as described above, Z 1 and Z 2 can be bonded to each other to form an aromatic ring. For example, as the structure when Z 1 and Z 2 in the above formula (M-1) are bonded to each other to form an aromatic ring, for example, the group represented by the following formula (M-1a) can be mentioned. In addition, in the following formula (M-1a), * represents the bonding position, and Q1 and Q 2 and Y 1 may be the same groups as those described in the above formula (M-1).
[0111] [Chemical formula 3]
[0112]
[0113] Moreover, in the above formulas (M-2) and (M-3), A 3 and A 4 each independently represent a group selected from the group consisting of -O-, -N(R 13 )-, -S-, and -CO-, and R 13 represents a hydrogen atom or a substituent.
[0114] As the substituent represented by R 13 , for example, the same groups as the above substituent X may be mentioned.
[0115] Moreover, in the above formula (M-2), X represents a hydrogen atom or a Group 14-16 non-metal atom to which a substituent can be bonded.
[0116] Moreover, as the Group 14-16 non-metal atom represented by X, for example, an oxygen atom, a sulfur atom, a nitrogen atom bonded to a hydrogen atom or a substituent, =N-R N1 , R N1 represents a hydrogen atom or a substituent. ], a carbon atom bonded to a hydrogen atom or a substituent, =C-(R C1 )2, R C1 represents a hydrogen atom or a substituent. ].
[0117] Specifically, as the substituent, for example, an alkyl group, an alkoxy group, an alkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (e.g., a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, an alkylcarbonyl group, a sulfo group, a hydroxyl group, etc. may be mentioned.
[0118] Moreover, in the above formula (M-3), D 7 and D 8 each independently represent a single bond or a divalent linking group of -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 - or a combination of two or more of them, and R 1 to R 5 each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 12 carbon atoms.
[0119] Here, as D7 and D 8 a divalent linking group represented by one of the following formulas, for example, -CO-, -O-, -CO-O-, -C(=S)O-, -CR 1 R 2 -, -CR 1 R 2 -CR 1 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 independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.
[0120] Among these, any one of -CO-, -O-, and -CO-O- is preferred.
[0121] And in the above formula (M-3), SP 3 and SP 4 each independently represents a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the linear or branched alkylene group having 1 to 12 carbon atoms are substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, and Q represents a substituent. As the substituent, for example, the same groups as the above substituent X can be mentioned.
[0122] Here, as SP 3 and SP 4The straight-chain or branched-chain alkylene group having 1 to 12 carbon atoms represented by one mode, for example, methylene, ethylene, propylene, butylene, pentylene, hexylene, methylhexylene, heptylene can be suitably cited. In addition, as described above, SP 1 and SP 2 may be a divalent linking group in which one or more of -CH2- constituting the straight-chain or branched-chain alkylene group having 1 to 12 carbon atoms are substituted with -O-, -S-, -NH-, -N(Q)- or -CO-. As the substituent represented by Q, for example, the same groups as the above-mentioned substituent X can be cited.
[0123] Further, in the above formula (M-3), L 3 and L 4 each independently represents a monovalent organic group.
[0124] As the monovalent organic group, for example, alkyl, aryl, heteroaryl, etc. can be cited.
[0125] The alkyl group may be straight-chain, branched-chain or cyclic, but is preferably straight-chain. The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 20, and further preferably 1 to 10.
[0126] Further, the aryl group may be monocyclic or polycyclic, but is preferably monocyclic. The number of carbon atoms of the aryl group is preferably 6 to 25, more preferably 6 to 10.
[0127] Further, the heteroaryl group may 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 atom, sulfur atom, oxygen atom. The number of carbon atoms of the heteroaryl group is preferably 6 to 18, more preferably 6 to 12.
[0128] Further, the alkyl group, aryl group and heteroaryl group may be unsubstituted or may have a substituent. As the substituent, for example, the same groups as the above-mentioned substituent X can be cited.
[0129] Further, in the above formulas (M-4) to (M-7), Ax represents an organic group having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles and having 2 to 30 carbon atoms.
[0130] Further, in the above formulas (M-4) to (M-7), Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms, and the organic group has at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.
[0131] Here, the aromatic rings in Ax and Ay may have substituents, or Ax and Ay may be bonded to form a ring.
[0132] And, Q 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have substituents.
[0133] As Ax and Ay, the groups described in paragraphs
[0039] to
[0095] of International Publication No. 2014 / 010325 can be cited.
[0134] And, as Q 3 The alkyl group having 1 to 20 carbon atoms represented, specifically, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, etc. can be cited. As substituents, for example, the same groups as the above-described substituent X can be cited.
[0135] Furthermore, in the present invention, for the reasons of improving the alignment property of the liquid crystal and the moisture resistance of the formed optically anisotropic film, at least one M in the above formula (II) preferably represents a cyclohexane ring, more preferably 1,4-cyclohexylene, and further preferably trans-1,4-cyclohexylene. In particular, when there are an odd number (for example, 3 or 5) of M, M located other than the center preferably represents a cyclohexane ring.
[0136] In the above formula (II), m represents an integer of 3 or more, preferably represents an integer of 3 to 6, and among the integers of 3 to 6, more preferably represents an odd number.
[0137] In addition, a plurality of Ms may be the same or different, and a plurality of Ds 22 may be the same or different.
[0138] Hereinafter, specific examples of the partial structure represented by -(M-D 22 ) m - in the above formula (II) are shown. In addition, in the specific examples shown below, * represents the bonding position, the benzene ring and the cyclohexane ring may be substituted with a fused ring or a substituent, and a part of carbon atoms may be substituted with a heteroatom.
[0139] [Chemical formula 4]
[0140]
[0141]
[0142] In the above formula (II), as the alkyl group shown as one mode of T, for example, the same groups as the alkyl groups exemplified in the above-described substituent X can be cited.
[0143] In the present invention, for the reason of improving the strength of the formed optically anisotropic film, T in the above formula (II) preferably represents a polymerizable group.
[0144] As the polymerizable group, a polymerizable group capable of radical polymerization or cationic polymerization is preferred.
[0145] As the radical polymerizable group, known radical polymerizable groups can be used. As the preferred radical polymerizable group, acryloyloxy or methacryloyloxy can be mentioned. In this case, it is known that the polymerization rate of acryloyloxy is generally fast. From the viewpoint of improving productivity, acryloyloxy is preferred, and methacryloyloxy can also be used as the polymerizable group in the same manner.
[0146] As the cationic polymerizable group, known cationic polymerizable groups can be used. Specifically, alicyclic ether groups, cyclic acetal groups, cyclic lactone groups, cyclic thioether groups, spiro orthoester groups, and vinyloxy groups can be mentioned. Among them, alicyclic ether groups or vinyloxy groups are preferred, and epoxy groups, oxetanyl groups, or vinyloxy groups are particularly preferred.
[0147] As an example of the particularly preferred polymerizable group, any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20) can be mentioned. Among them, acryloyloxy or methacryloyloxy is more preferred. In the following formulas (P-1) to (P-20), * represents the bonding position to SP 22 .
[0148] [Chemical formula 5]
[0149]
[0150] Hereinafter, specific examples of the partial structure represented by -SP 21 -D 21 - in the above formula (II) are shown. In the specific examples shown below, * represents the bonding position to M, and ** represents the bonding position to the oxygen atom.
[0151] [Chemical formula 6]
[0152]
[0153] Hereinafter, specific examples of the partial structure represented by -D 22 -SP 22 - in the above formula (II) are shown. In the specific examples shown below, * represents the bonding position to M, and ** represents the bonding position to T.
[0154] [Chemical formula 7]
[0155]
[0156] As specific compounds, specifically, for example, compounds represented by the following formulas (2-1-1) to (2-1-12) and (2-1) to (2-5) can be cited.
[0157] [Chemical formula 8]
[0158]
[0159]
[0160] In the present invention, from the viewpoint of preventing the hindrance of the alignment of the liquid crystal compound, the content of the specific compound is preferably 0.05 to 20% by mass, more preferably 0.1 to 10% by mass, and further preferably 0.2 to 5% by mass, based on the total mass of the liquid crystal compound and the specific compound described below.
[0161] [Liquid crystal compound]
[0162] 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.
[0163] Liquid crystal compounds can generally be classified into rod-like types and disc-like types according to their shapes. Moreover, they have low molecular and high molecular types respectively. High molecular usually refers to a polymer with a degree of polymerization of 100 or more (Physical Polymer Science and Phase Transition Kinetics, by Masao Doi, page 2, Iwanami Shoten, 1992).
[0164] In the present invention, any liquid crystal compound can be used, but a rod-like liquid crystalline compound or a disc-like liquid crystalline compound is preferably used, and a rod-like liquid crystalline compound is more preferably used.
[0165] From the viewpoint of fixing the alignment of the liquid crystal compound, the liquid crystal compound preferably has a polymerizable group.
[0166] As the polymerizable group, a polymerizable group capable of radical polymerization or cationic polymerization is preferred.
[0167] As the radical polymerizable group, well-known radical polymerizable groups can be used. As preferred radical polymerizable groups, acryloyloxy or methacryloyloxy can be cited. It is known that in this case, the polymerization rate of acryloyloxy is usually fast. From the viewpoint of improving productivity, acryloyloxy is preferred, and methacryloyloxy can also be used as a polymerizable group in the same manner.
[0168] As the cationic polymerizable group, well-known cationic polymerizable groups can be used. Specifically, alicyclic ether groups, cyclic acetal groups, cyclic lactone groups, cyclic thioether groups, spiro orthoester groups, and vinyloxy groups can be cited. Among them, alicyclic ether groups or vinyloxy groups are preferred, and epoxy groups, oxetanyl groups, or vinyloxy groups are particularly preferred.
[0169] As an example of a particularly preferred polymerizable group, any polymerizable group selected from the group including the groups represented by the above formulas (P-1) to (P-20) can be mentioned. Among them, acryloyloxy or methacryloyloxy is more preferred.
[0170] In the present invention, from the reason that accurate conversion of the light wavelength can be performed in a wide wavelength range, it is preferred that the liquid crystal compound has an inverse wavelength dispersion liquid crystal compound.
[0171] Here, in the present specification, a liquid crystal compound having "inverse wavelength dispersion" means a compound in which, when measuring the in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film made using the polymerizable liquid crystal compound, the Re value becomes equal to or higher as the measurement wavelength increases.
[0172] In addition, in the present invention, from the reason of taking both inverse wavelength dispersion and light resistance into consideration, the liquid crystal compound is preferably a compound having any aromatic ring selected from the group including the groups represented by the following formulas (Ar-1) to (Ar-7).
[0173] [Chemical formula 9]
[0174]
[0175] In the above formulas (Ar-1) to (Ar-7), * represents the bonding position to the part other than the above aromatic ring included in the liquid crystal compound, that is, the bonding position.
[0176] And Y in the above formulas (Ar-1) to (Ar-7) 1 , Q 1 , Q 2 , Q 3 , Z 1 , Z 2 , Z 3 , A 3 , A 4 , D 7 , D 8 , SP 3 , SP 4 , L 3 , L 4 , Ax and Ay are respectively the same as Y in the above formulas (M-1) to (M-7) described in the above specific compound 1 , Q 1 , Q 2 , Q 3 , Z 1 , Z 2 , Z 3 , A 3, A 4 , D 7 , D 8 , SP 3 , SP 4 , L 3 , L 4 , Ax and Ay are the same.
[0177] In the present invention, for the reason that the optical anisotropic film can be thinned in order to have a high refractive index anisotropy, the liquid crystal compound is preferably a compound represented by the following formula (I). Further, in the following formula (I), Ar represents any aromatic ring selected from the group consisting of the groups represented by the above formulas (Ar-1) to (Ar-7). Here, when q1 in the following formula (I) is 2, the plurality of Ars may be the same or different from each other.
[0178] L 1 -SP 1 -D 5 -(A 1 ) a1 -D 3 -(G 1 ) gi -D 1 -〔Ar-D 2 〕 q1 -(G 2 ) g2 -D 4 -(A 2 ) a2 -D 6 -Sp 2 -L 2 ……(I)
[0179] In the above formula (I), a1, a2, g1 and g2 each independently represent 0 or 1. Here, at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1.
[0180] And, in the above formula (I), q1 represents 1 or 2.
[0181] And, in the above formula (I), D 1 , D 2 , D 3 , D 4 , D 5 and D 6 each independently represents a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5- or a divalent linking group containing two or more of them in combination, R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 12 carbon atoms. Among them, when q1 is 2, a plurality of D 2 may be the same or different from each other.
[0182] Moreover, in the above formula (I), G 1 and G 2 each independently represents an aromatic ring having 6 to 20 carbon atoms which may have substituents or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have substituents, and one or more of -CH2- constituting the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-.
[0183] Moreover, in the above formula (I), A 1 and A 2 each independently represents an aromatic ring having 6 to 20 carbon atoms which may have substituents or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have substituents, and one or more of -CH2- constituting the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-.
[0184] Moreover, in the above formula (I), Sp 1 and Sp 2 each independently represents a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms or a divalent linking group in which one or more of -CH2- constituting the linear or branched alkylene group having 1 to 12 carbon atoms are substituted with -O-, -S-, -NH-, -N(Q)- or -CO-, and Q represents a substituent.
[0185] Moreover, in the above formula (I), L 1 and L 2 each independently represents a monovalent organic group, and at least one of L 1 and L 2 represents a polymerizable group. Among them, when Ar is the aromatic ring represented by the above formula (Ar-3), L 1 and L 2 and L 3 and L 4 in the above formula (Ar-3) each represent a polymerizable group.
[0186] In the above formula (I), a1, a2, g1 and g2 are all preferably 1.
[0187] Moreover, in the above formula (I), q1 is preferably 1.
[0188] In the above formula (I), as D 1 , D2 , D 3 , D 4 , D 5 and D 6 The divalent linking group shown in one mode of D in the above formula (M-3) may include D 7 and D 8 The same groups as those described in
[0189] Among these, any one of -CO-, -O- and -CO-O- is preferred.
[0190] In the above formula (I), as G 1 and G 2 The aromatic ring having 6 to 20 carbon atoms shown in one mode of, for example, may include: aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, phenanthroline ring; aromatic heterocycles such as furan ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, benzothiazole ring, among which, a benzene ring (for example, 1,4-phenyl, etc.) is preferred.
[0191] In the above formula (I), as G 1 and G 2 The divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms shown in one mode of is preferably a 5-membered ring or a 6-membered ring. And the alicyclic hydrocarbon group may be saturated or unsaturated, and a saturated alicyclic hydrocarbon group is preferred. As the divalent alicyclic hydrocarbon group represented by G 1 and G 2 For example, it can refer to the description in paragraph
[0078] of Japanese Patent Laid-Open No. 2012-21068, and this content is incorporated into the specification of this application.
[0192] In the present invention, G in the above formula (I) 1 and G 2 is preferably a cycloalkane ring.
[0193] As the cycloalkane ring, specifically, for example, it may include cyclohexane ring, cycloheptane ring, cyclooctane ring, cyclododecane ring, cyclodocosane ring, etc.
[0194] Among these, a cyclohexane ring is preferred, a 1,4-cyclohexylene is more preferred, and a trans-1,4-cyclohexylene is further preferred.
[0195] And in the above formula (I), regarding G 1 and G 2 , as the substituents that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms may have, the same substituents as those that Y in the above formula (Ar-1) 1 may have can be cited.
[0196] In the above formula (I), as A 1 and A 2 in one embodiment, the aromatic ring having 6 to 20 or more carbon atoms can be exemplified by the same group as the aromatic ring described in G 1 and G 2 in the above formula (I).
[0197] Furthermore, in the above formula (I), as A 1 and A 2 in one embodiment, the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms can be exemplified by the same group as the alicyclic hydrocarbon group described in G 1 and G 2 in the above formula (I).
[0198] In addition, regarding A 1 and A 2 , as the substituent that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms can have, for example, the same substituent as the above substituent X can be exemplified.
[0199] In the above formula (I), as SP 1 and SP 2 in one embodiment, the linear or branched alkylene group having 1 to 12 carbon atoms can be exemplified by the same group as the alkylene group described in SP 3 and SP 4 in the above formula (M-3).
[0200] In the above formula (I), as the monovalent organic group represented by L 1 and L 2 , the same group as the organic group described in L 3 and L 4 in the above formula (M-3) can be exemplified.
[0201] In the above formula (I), as the polymerizable group represented by at least one of L 1 and L 2 , the above polymerizable group capable of radical polymerization or cationic polymerization can be exemplified.
[0202] As an example of a particularly preferred polymerizable group, any polymerizable group selected from the group consisting of the groups represented by the above formulas (P-1) to (P-20) can be exemplified. Among them, acryloyloxy or methacryloyloxy is more preferred.
[0203] In the above formula (I), for the reason of good durability, both L 1 and L 2 in the above formula (I) are preferably polymerizable groups, and acryloyloxy or methacryloyloxy is more preferred.
[0204] Examples of the compound represented by the above formula (I) include the compound represented by the general formula (1) described in Japanese Patent Laid-Open No. 2010-084032 (especially the compounds described in paragraphs
[0067] to
[0073] ), the compound represented by the general formula (II) described in Japanese Patent Laid-Open No. 2016-053709 (especially the compounds described in paragraphs
[0036] to
[0043] ), and the compound represented by the general formula (1) described in Japanese Patent Laid-Open No. 2016-081035 (especially the compounds described in paragraphs
[0043] to
[0055] ).
[0205] In addition, examples of the compound represented by the above formula (I) include the compounds represented by the following formulas (1) to (22). Specifically, as K (side chain structure) in the following formulas (1) to (22), compounds having the side chain structures represented by the following K-1-1 to K-8-9 can be cited respectively.
[0206] In addition, the "*" shown in the side chain structures represented by the following K-1-1 to K-8-9 indicates the bonding position to the aromatic ring.
[0207] In addition, in the side chain structures represented by the following Table K-1-12 etc., the groups adjacent to acryloyloxy and methacryloyl respectively represent propylene group (a group obtained by substituting methyl for ethylidene), and represent a mixture of positional isomers with different methyl positions.
[0208] [Chemical formula 10]
[0209]
[0210] [Chemical formula 11]
[0211]
[0212]
[0213] [Chemical formula 12]
[0214]
[0215] [Chemical formula 13]
[0216]
[0217]
[0218] [Chemical formula 14]
[0219]
[0220] [Chemical Formula 15]
[0221]
[0222]
[0223] [Chemical Formula 16]
[0224]
[0225] [Chemical Formula 17]
[0226]
[0227] [Chemical Formula 18]
[0228]
[0229] [Other Polymerizable Compounds]
[0230] In addition to the above-mentioned specific compounds and liquid crystal compounds, the liquid crystal composition of the present invention may contain other polymerizable compounds having one or more polymerizable groups.
[0231] Here, the polymerizable groups possessed by other polymerizable compounds are not particularly limited. For example, acryloyl, methacryloyl, vinyl, styryl, allyl, etc. can be mentioned. Among them, acryloyl and methacryloyl are preferred.
[0232] As other polymerizable compounds, the compounds described in paragraphs
[0073] to
[0074] of JP-A-2016-053709 can be mentioned.
[0233] Moreover, as other polymerizable compounds, the compounds represented by formulas (M1), (M2), and (M3) described in paragraphs
[0030] to
[0033] of JP-A-2014-077068 can be mentioned. More specifically, the specific examples described in paragraphs
[0046] to
[0055] of the same publication can be mentioned.
[0234] Furthermore, as other polymerizable compounds, the polymerizable compounds having the structures of formulas (1) to (3) described in JP-A-2014-198814 can be preferably used. More specifically, the specific examples described in paragraphs
[0020] to
[0035] ,
[0042] to
[0050] , and
[0056] to
[0057] of the same publication can be mentioned.
[0235] When containing such other polymerizable compounds, the content is preferably less than 50% by mass, more preferably 40% by mass or less, and further preferably 2 to 30% by mass with respect to the mass of the above-mentioned liquid crystal compounds.
[0236] [Polymerization initiator]
[0237] Preferably, the liquid crystal composition of the present invention contains a polymerization initiator.
[0238] Preferably, the polymerization initiator used is a photoinitiator capable of initiating a polymerization reaction by ultraviolet irradiation.
[0239] As photoinitiators, for example, α-carbonyl compounds (described in the specifications of U.S. Patent No. 2367661 and U.S. Patent No. 2367670), acyloin ethers (described in the specification of U.S. Patent No. 2448828), α-hydrocarbon-substituted aromatic acyloin compounds (described in the specification of U.S. Patent No. 2722512), polynuclear quinone compounds (described in the specifications of U.S. Patent No. 3046127 and U.S. Patent No. 2951758), a combination of triaryl imidazole dimer and p-aminophenyl ketone (described in the specification of U.S. Patent No. 3549367), acridine and phenazine compounds (described in Japanese Patent Laid-Open No. 60-105667 and the specification of U.S. Patent No. 4239850), and oxadiazole compounds (described in the specification of U.S. Patent No. 4212970), acylphosphine oxides (described in Japanese Patent Publication No. 63-40799, Japanese Patent Publication No. 5-29234, Japanese Patent Laid-Open No. 10-95788, and Japanese Patent Laid-Open No. 10-29997), etc.
[0240] Moreover, in the present invention, the polymerization initiator is also preferably an oxime-based polymerization initiator, and specific examples thereof include the initiators described in paragraphs
[0049] to
[0052] of International Publication No. 2017 / 170443.
[0241] [Solvent]
[0242] From the viewpoint of the operability of forming an optically anisotropic film, etc., it is preferred that the liquid crystal composition of the present invention contains a solvent.
[0243] As the solvent, specifically, for example, ketone solvents (e.g., acetone, 2-butanone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, etc.), ether solvents (e.g., dioxane, tetrahydrofuran, etc.), cyclic amide solvents (e.g., N-methylpyrrolidone, N-ethylpyrrolidone, N,N'-dimethylimidazolidinone, etc.), aliphatic hydrocarbon solvents (e.g., hexane, etc.), alicyclic hydrocarbon solvents (e.g., cyclohexane, etc.), aromatic hydrocarbon solvents (e.g., toluene, xylene, trimethylbenzene, etc.), halogenated carbon solvents (e.g., dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.), ester solvents (e.g., methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohol solvents (e.g., ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolve solvents (e.g., methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetate solvents, sulfoxide solvents (e.g., dimethyl sulfoxide, etc.), chain amide solvents (e.g., dimethylformamide, dimethylacetamide, etc.) etc. can be mentioned. One of them can be used alone, or two or more of them can be used simultaneously.
[0244] In the present invention, among the above solvents, from the reason that the effect of the present invention for suppressing the increase in filtration pressure is remarkable, at least one solvent selected from the group including ketone solvents, ether solvents and cyclic amide solvents is preferred.
[0245] 〔Leveling agent〕
[0246] From the viewpoint of keeping the surface of the optically anisotropic film smooth and making the orientation control easier, it is preferred that the liquid crystal composition of the present invention contains a leveling agent.
[0247] As such a leveling agent, from the reason that the leveling effect is high with respect to the addition amount, a fluorine-based leveling agent or a silicon-based leveling agent is preferred, and from the viewpoint of being difficult to cause exudation (blooming, leakage), a fluorine-based leveling agent is more preferred.
[0248] As a leveling agent, specifically, for example, compounds described in paragraphs
[0079] to
[0102] of Japanese Patent Application Laid-Open No. 2007-069471, compounds represented by general formula (I) described in Japanese Patent Application Laid-Open No. 2013-047204 (particularly, compounds described in paragraphs
[0020] to
[0032] ), compounds represented by general formula (I) described in Japanese Patent Application Laid-Open No. 2012-211306 (particularly, compounds described in paragraphs
[0022] to
[0029] ), a liquid crystal alignment promoter represented by general formula (I) described in Japanese Patent Application Laid-Open No. 2002-129162 (particularly, compounds described in paragraphs
[0076] to
[0078] and
[0082] to
[0084] ), compounds represented by general formula (I), (II), and (III) described in Japanese Patent Application Laid-Open No. 2005-099248 (particularly, compounds described in paragraphs
[0092] to
[0096] ), etc. can be cited. In addition, it can also have the function of an alignment control agent described later.
[0249] [Alignment control agent]
[0250] If necessary, the liquid crystal composition of the present invention can contain an alignment control agent.
[0251] By using the alignment control agent, in addition to homogeneous alignment, various alignment states such as vertical alignment (Vertical alignment), tilted alignment, hybrid alignment, and cholesteric alignment can be formed, and a specific alignment state can be controlled and achieved more uniformly and precisely.
[0252] As an alignment control agent for promoting homogeneous alignment, for example, a low-molecular-weight alignment control agent or a high-molecular-weight alignment control agent can be used.
[0253] As a low-molecular-weight alignment control agent, for example, reference can be made to the descriptions in paragraphs
[0009] to
[0083] of Japanese Patent Application Laid-Open No. 2002-20363, paragraphs
[0111] to
[0120] of Japanese Patent Application Laid-Open No. 2006-106662, and paragraphs
[0021] to
[0029] of Japanese Patent Application Laid-Open No. 2012-211306, and the content is incorporated into the specification of the present application.
[0254] And, as a high-molecular-weight alignment control agent, for example, reference can be made to the descriptions in paragraphs
[0021] to
[0057] of Japanese Patent Application Laid-Open No. 2004-198511 and paragraphs
[0121] to
[0167] of Japanese Patent Application Laid-Open No. 2006-106662, and the content is incorporated into the specification of the present application.
[0255] Further, as an alignment control agent for forming or promoting vertical alignment, for example, a boric acid compound or an onium salt compound can be cited. Specifically, reference can be made to paragraphs
[0023] to
[0032] of Japanese Patent Application Laid-Open No. 2008-225281, paragraphs
[0052] to
[0058] of Japanese Patent Application Laid-Open No. 2012-208397, paragraphs
[0024] to
[0055] of Japanese Patent Application Laid-Open No. 2008-026730, paragraphs
[0043] to
[0055] of Japanese Patent Application Laid-Open No. 2016-193869, etc. The compounds described therein are incorporated into the specification of this application.
[0256] On the other hand, regarding cholesteric alignment, it can be achieved by adding a chiral agent to the liquid crystal composition of the present invention, and the helical direction of cholesteric alignment can be controlled according to its chiral direction. In addition, the pitch of cholesteric alignment can be controlled according to the alignment restricting force of the chiral agent.
[0257] With respect to the total solid content mass in the liquid crystal composition, the content when containing the alignment control agent is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass. If the content is within this range, an optically anisotropic film with a desired alignment state can be obtained, and there is no precipitation, phase separation, alignment defects, etc., and it is uniform and highly transparent.
[0258] These alignment control agents can also be imparted with polymerizable functional groups, and in particular, polymerizable functional groups capable of polymerizing with the polymerizable liquid crystal compounds constituting the liquid crystal composition of the present invention can be imparted.
[0259] 〔Other components〕
[0260] The polymerizable liquid crystal composition of the present invention may further contain components other than the above components. For example, liquid crystal compounds other than the above polymerizable liquid crystal compounds, surfactants, tilt angle control agents, alignment aids, plasticizers, crosslinking agents, etc. can be cited.
[0261] [Compound]
[0262] The compound of the present invention is the compound represented by the above formula (II), and is the same as the compound described as a specific compound in the liquid crystal composition of the present invention above.
[0263] [Optically anisotropic film]
[0264] The optically anisotropic film of the present invention is an optically anisotropic film obtained by polymerizing the liquid crystal composition of the present invention above.
[0265] As a method for forming an optically anisotropic film, for example, there can be mentioned a method in which the above-described liquid crystal composition of the present invention is used, and after setting it to a desired alignment state, it is fixed by polymerization. In particular, in the present invention, it is preferably in the following manner: after preparing the liquid crystal composition of the present invention, after passing through a storage step, an optically anisotropic film is formed.
[0266] Here, the polymerization conditions are not particularly limited, but in the polymerization by light irradiation, ultraviolet rays are preferably used. The irradiation amount is preferably 10 mJ / cm 2 ~50 J / cm 2 and more preferably 20 mJ / cm 2 ~5 J / cm 2 and further preferably 30 mJ / cm 2 ~3 J / cm 2 and particularly preferably 50 to 1000 mJ / cm 2 . And in order to promote the polymerization reaction, it can be carried out under heating conditions.
[0267] In addition, in the present invention, the optically anisotropic film can be formed on any support of the optical film of the present invention described later or on the polarizer of the polarizing plate of the present invention described later.
[0268] The optically anisotropic film of the present invention preferably satisfies the following formula (III).
[0269] 0.50 < Re(450) / Re(550) < 1.00... (III)
[0270] Here, in the above formula (III), Re(450) represents the in-plane retardation of the optically anisotropic film at a wavelength of 450 nm, and Re(550) represents the in-plane retardation of the optically anisotropic film at a wavelength of 550 nm. In addition, in the present specification, when the measurement wavelength of the retardation is not specified, the measurement wavelength is set to 550 nm.
[0271] And the in-plane retardation value refers to the value measured using AxoScan OPMF-1 (manufactured by Opto Science, Inc.) and using light of the measurement wavelength.
[0272] Specifically, it is calculated by inputting the average refractive index ((Nx + Ny + Nz) / 3) and the film thickness (d (μm)) using AxoScan OPMF-1 as follows:
[0273] Slow axis direction (°)
[0274] Re(λ) = R0(λ)
[0275] Rth(λ) = ((nx + ny) / 2 - nz) × d.
[0276] In addition, R0(λ) is shown as a value calculated using AxoScan OPMF-1, but refers to Re(λ).
[0277] The optically anisotropic film of the present invention is preferably a positive A-plate or a positive C-plate, more preferably a positive A-plate.
[0278] Here, the positive A-plate (positive A plate) and the positive C-plate (positive C plate) are defined as follows.
[0279] When the refractive index in the slow axis direction in the film plane (the direction with the maximum refractive index in the plane) is nx, the refractive index in the direction orthogonal to the slow axis in the plane is ny, and the refractive index in the thickness direction is nz, the positive A-plate satisfies the relationship of formula (A1), and the positive C-plate satisfies the relationship of formula (C1). In addition, the positive A-plate indicates that Rth is a positive value, and the positive C-plate indicates that Rth is a negative value.
[0280] Formula (A1) nx > ny ≈ nz
[0281] Formula (C1) nz > nx ≈ ny
[0282] In addition, the so-called "≈" includes not only the case where the two are exactly the same, but also the case where the two are substantially the same.
[0283] The so-called "substantially the same" means that in the positive A-plate, for example, even when (ny - nz) × d (where d is the thickness of the thin film) is -10 to 10 nm, preferably -5 to 5 nm, it is included in "ny ≈ nz", and even when (nx - nz) × d is -10 to 10 nm, preferably -5 to 5 nm, it is included in "nx ≈ nz". And in the positive C-plate, for example, even when (nx - ny) × d (where d is the thickness of the thin film) is 0 to 10 nm, preferably 0 to 5 nm, it is included in "nx ≈ ny".
[0284] When the optically anisotropic film 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, still more preferably 130 to 150 nm, and particularly preferably 130 to 140 nm.
[0285] Here, the "λ / 4 plate" refers to a plate having a λ / 4 function, specifically, a plate having a function of converting linearly polarized light of a certain specific wavelength into circularly polarized light (or converting circularly polarized light into linearly polarized light).
[0286] [Optical film]
[0287] The optical film of the present invention is an optical film having the optically anisotropic film of the present invention.
[0288] Figure 1 A, Figure 1 B, and Figure 1 C (hereinafter, when there is no need to particularly distinguish these drawings, simply referred to as " Figure 1 ".) are respectively schematic cross-sectional views showing an example of the optical film of the present invention.
[0289] In addition, Figure 1 being a schematic diagram, the relationship between the thicknesses of each layer, the positional relationship, etc. are not necessarily consistent with the actual situation, Figure 1 and the support, alignment film, and hard coat shown in
[0290] Figure 1 are all optional constituent components. The optical film 10 shown in
[0291] has a support 16, an alignment film 14, and an optically anisotropic film 12 in this order. Figure 1 And, as shown in Figure 1 B, the optical film 10 may have a hard coat 18 on the side of the support 16 opposite to the side where the alignment film 14 is provided, and as shown in
[0292] C, it may have a hard coat 18 on the side of the optically anisotropic film 12 opposite to the side where the alignment film 14 is provided.
[0293] 〔Optically Anisotropic Film〕
[0294] The optically anisotropic film included in the optical film of the present invention is the above-mentioned optically anisotropic film of the present invention.
[0295] In the optical film of the present invention, there is no particular limitation on the thickness of the above-mentioned optically anisotropic film, but it is preferably 0.1 to 10 μm, more preferably 0.5 to 5 μm.
[0296] 〔Support〕
[0297] As described above, the optical film of the present invention may have a support as a substrate for forming the optically anisotropic film.
[0298] Preferably, such a support is transparent. Specifically, the light transmittance is preferably 80% or more.
[0299] As such a support, for example, a glass substrate or a polymer film can be mentioned. As a material for the polymer film, a cellulose-based polymer can be mentioned; an acrylic polymer having an acrylate polymer such as polymethyl methacrylate or a polymer containing a lactone ring; a thermoplastic norbornene-based polymer; a polycarbonate-based polymer; a polyester-based polymer such as polyethylene terephthalate or polyethylene naphthalate; a styrene-based polymer such as polystyrene or acrylonitrile-styrene copolymer (AS resin); a polyolefin-based polymer such as polyethylene, polypropylene, or ethylene-propylene copolymer; a vinyl chloride-based polymer; an amide-based polymer such as nylon or aromatic polyamide; an imide-based polymer; a sulfone-based polymer; a polyethersulfone-based polymer; a polyetheretherketone-based polymer; a polyphenylene sulfide-based polymer; a vinylidene chloride-based polymer; a vinyl alcohol-based polymer; a vinyl butyral-based polymer; an aromatic ester-based polymer; a polyoxymethylene-based polymer; an epoxy-based polymer; or a polymer obtained by mixing these polymers.
[0300] Also, it may be a mode in which a polarizer described later also serves as such a support.
[0301] In the present invention, the thickness of the above-mentioned support is not particularly limited, but it is preferably 5 to 60 μm, more preferably 5 to 30 μm.
[0302] 〔Alignment film〕
[0303] When the optical film of the present invention has any of the above-mentioned supports, it is preferable to have an alignment film between the support and the optically anisotropic film. Alternatively, it may be a mode in which the above-mentioned support also serves as an alignment film.
[0304] The alignment film usually has a polymer as a main component. As a polymer material for the alignment film, it is described in many documents, and many commercially available products can be obtained.
[0305] The polymer material used in the present invention is preferably polyvinyl alcohol or polyimide and its derivatives. Particularly preferably, it is modified or unmodified polyvinyl alcohol.
[0306] Regarding the alignment film that can be used in the present invention, for example, the alignment film described in International Publication No. 01 / 88574, pages 43, line 24 to page 49, line 8; the modified polyvinyl alcohol described in paragraphs
[0071] to
[0095] of Japanese Patent No. 3907735; the liquid crystal alignment film formed by a liquid crystal aligning agent described in Japanese Patent Application Laid-Open No. 2012-155308, etc. can be mentioned.
[0307] In the present invention, from the reason that the surface morphology can be prevented from deteriorating by not contacting the surface of the alignment film when forming the alignment film, it is also preferable to use a photo-alignment film as the alignment film.
[0308] As the photo-alignment film, there is no particular limitation, but polymer materials such as polyamide compounds and polyimide compounds described in paragraphs
[0024] to
[0043] of International Publication No. 2005 / 096041 can be used; a liquid crystal alignment film formed by a liquid crystal aligning agent having a photo-alignment group described in Japanese Patent Application Laid-Open No. 2012-155308; products such as LPP-JP265CP manufactured by Rolic Technologies Co., Ltd.
[0309] Moreover, in the present invention, the thickness of the above-mentioned alignment film is not particularly limited, but from the viewpoint of alleviating surface irregularities that can exist on the support to form an optically anisotropic film with a uniform film thickness, it is preferably 0.01 to 10 μm, more preferably 0.01 to 1 μm, and still more preferably 0.01 to 0.5 μm.
[0310] 〔Hard coat〕
[0311] In order to impart physical strength to the thin film, it is preferable that the optical film of the present invention has a hard coat. Specifically, a hard coat can be provided on the side of the support opposite to the side where the alignment film is provided (refer to Figure 1 B), or a hard coat can be provided on the side of the optically anisotropic film opposite to the side where the alignment film is provided (refer to Figure 1 C).
[0312] As the hard coat, the hard coat described in paragraphs
[0190] to
[0196] of Japanese Patent Application Laid-Open No. 2009-98658 can be used.
[0313] 〔Other optically anisotropic films〕
[0314] The optical film of the present invention may further have other optically anisotropic films different from the optically anisotropic film of the present invention.
[0315] That is, the optical film of the present invention may have a laminated structure of the optically anisotropic film of the present invention and other optically anisotropic films.
[0316] Such other optically anisotropic films are not combined with the above-mentioned specific compounds, and as long as they are optically anisotropic films obtained by using the above-mentioned inverse wavelength dispersion liquid crystal compounds or other polymerizable compounds (especially, liquid crystal compounds), there is no particular limitation.
[0317] Here, generally, liquid crystal compounds can be classified into rod-shaped types and disc-shaped types according to their shapes. In addition, there are also low-molecular and high-molecular types. High polymers generally refer to high polymers with a degree of polymerization of 100 or more (Physical Polymer Science and Phase Transition Kinetics, written by Masao Doi, page 2, Iwanami Shoten, 1992). In the present invention, any liquid crystal compound can also be used, but rod-shaped liquid crystal compounds or disc-shaped liquid crystal compounds (disc-shaped liquid crystal compounds) are preferably used. Two or more kinds of rod-shaped liquid crystal compounds, two or more kinds of disc-shaped liquid crystal compounds, or a mixture of rod-shaped liquid crystal compounds and disc-shaped liquid crystal compounds can also be used. In order to fix the above-mentioned liquid crystal compounds, it is more preferable to use rod-shaped liquid crystal compounds or disc-shaped liquid crystal compounds having polymerizable groups to form them. Further preferably, the liquid crystal compound has two or more polymerizable groups in one molecule. When the liquid crystal compound is a mixture of two or more kinds, it is preferable that at least one liquid crystal compound has two or more polymerizable groups in one molecule.
[0318] As the rod-shaped liquid crystal compound, for example, the compounds described in Claim 1 of Japanese Patent Application Laid-Open No. 2009-513019 or paragraphs
[0026] to
[0098] of Japanese Patent Application Laid-Open No. 2005-289980 can be preferably used. As the disc-shaped liquid crystal compound, for example, the compounds described in paragraphs
[0020] to
[0067] of Japanese Patent Application Laid-Open No. 2007-108732 or paragraphs
[0013] to
[0108] of Japanese Patent Application Laid-Open No. 2010-244038 can be preferably used, but it is not limited to these.
[0319] 〔Ultraviolet Absorbent〕
[0320] Considering the influence of external light (especially ultraviolet light), the optical film of the present invention preferably contains an ultraviolet (UV) absorbent.
[0321] The ultraviolet absorbent can be contained in the optically anisotropic film of the present invention or in components other than the optically anisotropic film constituting the optical film of the present invention. As components other than the optically anisotropic film, for example, a support can be appropriately cited.
[0322] As the ultraviolet absorbent, any conventionally known ultraviolet absorbent capable of exhibiting ultraviolet absorbency can be used. Among such ultraviolet absorbents, from the viewpoint of obtaining high ultraviolet absorbency and ultraviolet absorbability (ultraviolet cut-off ability) that can be used in an image display device, benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorbents are preferably used.
[0323] Moreover, in order to broaden the absorption width of ultraviolet light, two or more ultraviolet absorbents having different maximum absorption wavelengths can be used simultaneously.
[0324] As an ultraviolet absorber, specifically, for example, compounds described in paragraphs
[0258] to
[0259] of Japanese Patent Application Laid-Open No. 2012-18395, compounds described in paragraphs
[0055] to
[0105] of Japanese Patent Application Laid-Open No. 2007-72163, etc. can be cited.
[0325] Moreover, as commercially available products, Tinuvin400, Tinuvin405, Tinuvin460, Tinuvin477, Tinuvin479, Tinuvin1577 (all manufactured by BASF Corporation), etc. can be used.
[0326] [Polarizing plate]
[0327] The polarizing plate of the present invention has the above-described optical film and polarizer of the present invention.
[0328] Moreover, when the above-described optical anisotropic film of the present invention is a λ / 4 plate (positive A plate), the polarizing plate of the present invention can be used as a circular polarizing plate.
[0329] Moreover, when the above-described optical anisotropic film of the present invention is a λ / 4 plate (positive A plate), in the polarizing plate of the present invention, the angle formed by 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°, further preferably 42 to 48°, and particularly preferably 45°.
[0330] Here, the "slow axis" of the λ / 4 plate represents the direction in which the refractive index in the plane of the λ / 4 plate becomes the maximum, and the "absorption axis" of the polarizer represents the direction in which the absorbance is the highest.
[0331] [Polarizer]
[0332] Regarding the polarizer included in the polarizing plate of the present invention, as long as it is a component having a function of converting light into specific linearly polarized light, there is no particular limitation, and conventionally known absorption-type polarizers and reflection-type polarizers can be used.
[0333] As the absorption-type polarizer, an iodine-based polarizer, a dye-based polarizer using a dichroic dye, a polyene-based polarizer, etc. can be used. The iodine-based polarizer and the dye-based polarizer include a coating-type polarizer and a stretched-type polarizer, and both can be applied, but a polarizer produced by adsorbing iodine or a dichroic dye on polyvinyl alcohol and stretching it is preferred.
[0334] Further, as a method for obtaining a polarizer by performing stretching and dyeing in a state of a laminated film having a polyvinyl alcohol layer formed on a substrate, Japanese Patent No. 5048120, Japanese Patent No. 5143918, Japanese Patent No. 4691205, Japanese Patent No. 4751481, and Japanese Patent No. 4751486 can be cited, and publicly known techniques related to these polarizers can also be preferably used.
[0335] As the reflective polarizer, a polarizer obtained by laminating films having different birefringences, a wire grid polarizer, a polarizer obtained by combining a cholesteric liquid crystal having a selective reflection region and a quarter-wave plate, etc. can be used.
[0336] Among them, from the viewpoint of more excellent adhesion, a polarizer containing a polyvinyl alcohol-based resin (a polymer containing -CH2-CHOH- as a repeating unit, particularly, at least one selected from the group including polyvinyl alcohol and ethylene-vinyl alcohol copolymer) is preferred.
[0337] In the present invention, the thickness of the polarizer is not particularly limited, but it is preferably 3 μm to 60 μm, more preferably 5 μm to 30 μm, and further preferably 5 μm to 15 μm.
[0338] [Adhesive layer]
[0339] The polarizing plate of the present invention may have an adhesive layer disposed between the optically anisotropic film and the polarizer in the optical film of the present invention.
[0340] As the adhesive layer for laminating the optically anisotropic film and the polarizer, for example, a substance having a ratio of storage modulus G' to loss modulus G'' (tanδ = G'' / G') measured by a dynamic viscoelasticity measuring device of 0.001 to 1.5 is represented, and includes so-called adhesives or substances that are prone to creep, etc. As the adhesive that can be used in the present invention, for example, a polyvinyl alcohol-based adhesive can be cited, but it is not limited thereto.
[0341] [Image display device]
[0342] The image display device of the present invention is an image display device having the optical film or the polarizing plate of the present invention.
[0343] The display element used in the image display device of the present invention is not particularly limited, and for example, a liquid crystal cell, an organic electroluminescence (hereinafter, simply referred to as "EL") display panel, a plasma display panel, etc. can be cited.
[0344] Among these, a liquid crystal cell and an organic EL display panel are preferred, and a liquid crystal cell is more preferred. That is, as the image display device of the present invention, a liquid crystal display device using a liquid crystal cell as a display element and an organic EL display device using an organic EL display panel as a display element are preferred, and a liquid crystal display device is more preferred.
[0345] [Liquid Crystal Display Device]
[0346] A liquid crystal display device as an example of the image display device of the present invention is a liquid crystal display device having the polarizing plate and liquid crystal cell of the present invention described above.
[0347] In addition, in the present invention, among the polarizing plates provided on both sides of the liquid crystal cell, it is preferred to use the polarizing plate of the present invention as the front polarizing plate, and it is more preferred to use the polarizing plate of the present invention as the front and rear polarizing plates.
[0348] Hereinafter, the liquid crystal cell constituting the liquid crystal display device will be described in detail.
[0349] <Liquid Crystal Cell>
[0350] The liquid crystal cell used in the liquid crystal display device is preferably a VA (Vertical Alignment) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, an FFS (Fringe-Field-Switching) mode, or a TN (Twisted Nematic) mode, but is not limited to these.
[0351] In the liquid crystal cell of the TN mode, when no voltage is applied, the rod-shaped liquid crystalline molecules are substantially horizontally oriented and then twisted and oriented by 60 to 120°. The liquid crystal cell of the TN mode is most commonly used as a color TFT liquid crystal display device and is described in a number of documents.
[0352] In a liquid crystal cell of the VA mode, rod-shaped liquid crystalline molecules are substantially vertically aligned when no voltage is applied. In a liquid crystal cell of the VA mode, in addition to a liquid crystal cell of a narrow sense VA mode (described in Japanese Patent Laid-Open No. 2-176625) which causes rod-shaped liquid crystalline molecules to be substantially vertically aligned when no voltage is applied and causes them to be substantially horizontally aligned when a voltage is applied, there are also included (2) a liquid crystal cell (MVA mode) in which the VA mode is multi-domainized for the purpose of expanding the viewing angle (described in SID97, Digest of tech.Papers 28(1997)845), (3) a liquid crystal cell of a mode (n-ASM mode) in which rod-shaped liquid crystalline molecules are substantially vertically aligned when no voltage is applied and are twisted multi-domain aligned when a voltage is applied (described in the proceedings of the Japanese Liquid Crystal Symposium 58-59(1998)), and (4) a liquid crystal cell of the SURVIVAL mode (published in LCD International 98). And it can be any one of PVA (Patterned Vertical Alignment), optical alignment type, and PSA (Polymer-Sustained Alignment). Details of these modes are described in detail in Japanese Patent Laid-Open No. 2006-215326 and Japanese Patent Publication No. 2008-538819.
[0353] Regarding a liquid crystal cell of the IPS mode, rod-shaped liquid crystal molecules are substantially parallel aligned with respect to the substrate, and the liquid crystal molecules respond in a plane by applying an electric field parallel to the substrate surface. Regarding the IPS mode, it becomes black display in a state where no electric field is applied, and the absorption axes of a pair of upper and lower polarizers are orthogonal. Methods of using an optical compensation film to reduce light leakage during black display in an oblique direction and improve the viewing angle are disclosed in Japanese Patent Laid-Open No. 10-54982, Japanese Patent Laid-Open No. 11-202323, Japanese Patent Laid-Open No. 9-292522, Japanese Patent Laid-Open No. 11-133408, Japanese Patent Laid-Open No. 11-305217, Japanese Patent Laid-Open No. 10-307291, etc.
[0354] 〔Organic EL display device〕
[0355] Regarding an organic EL display device as an example of the image display device of the present invention, for example, a mode having a polarizer, a λ / 4 plate (positive A plate) including the optical anisotropic film of the present invention, and an organic EL display panel in this order from the observation side can be suitably cited.
[0356] Further, the organic EL display panel is a display panel composed of organic EL elements in which an organic light-emitting layer (organic electroluminescent layer) is sandwiched between electrodes (a cathode and an anode). The configuration of the organic EL display panel is not particularly limited, and a known structure can be adopted.
[0357] Examples
[0358] Hereinafter, the present invention will be described in further detail based on examples. Regarding the materials, amounts used, ratios, processing contents, processing sequences, etc. shown in the following examples, appropriate changes can be made as long as the gist of the present invention is not deviated from. Therefore, the scope of the present invention should not be construed in a limiting manner by the examples shown below.
[0359] [Synthesis of Specific Compound (2-1)]
[0360] The specific compound (2-1) was synthesized according to the following scheme.
[0361] [Chemical Formula 19]
[0362]
[0363] <STEP1>
[0364] As shown in the above scheme, 60.0 g of compound (2-1-a: 4-hydroxybutyl acrylate), 49.3 g of triethylamine, and 0.9 g of BHT (dibutylhydroxytoluene) were mixed into 120.1 mL of DMAc (dimethylacetamide) and 114.1 mL of toluene.
[0365] Next, the internal temperature was cooled to 0°C, and 50.6 g of methanesulfonyl chloride was slowly added dropwise. After the addition was completed, the mixture was stirred at an internal temperature of 0°C for 1 hour. Then, it was returned to room temperature (23°C), separated by dilute hydrochloric acid, and subjected to a second separation with saturated brine to obtain compound (2-1-b).
[0366] The toluene solution of compound (2-1-b) obtained above, 91.40 g of 1,1'-dihexyl-4,4'-dicarboxylic acid, 72.73 g of triethylamine, and 0.8 g of dibutylhydroxytoluene were mixed into 274.2 mL of DMAc and 69.7 mL of toluene. Next, the internal temperature was heated to 90°C and reacted for 5 hours. Then, it was returned to room temperature, dilute hydrochloric acid was added, and the mixture was heated to 42°C for separation. Next, 0.5 g of TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl) and 164.5 mL of toluene were added, and then, it was subjected to two separations with an aqueous sodium bicarbonate solution. The obtained solution was dropped into hexane to precipitate a solid, and a white solid compound (2-1-c) was obtained.
[0367] <STEP2-1>
[0368] 10.0 g of the compound (2-1-c) obtained above and 0.6 g of 1-butyl-3-methylimidazolium tetrafluoroborate were mixed with 50 mL of water. Then, 5.2 g of dimethylamine was slowly added dropwise. After the addition was completed, the mixture was stirred at room temperature (23 °C) for 30 minutes. Then, 50 mL of acetonitrile was added, and water was removed by azeotropic concentration. The solid that had precipitated was removed to obtain the compound (2-1-d).
[0369] <STEP2-2>
[0370] 11.7 g of the compound (2-1-c) obtained above, 13.1 g of the compound (2-1-e), and 0.2 g of BHT (dibutylhydroxytoluene) were mixed in 150 mL of tetrahydrofuran and 50 mL of chloroform. Then, 7.6 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.6 g of N,N-dimethyl-4-aminopyridine were added, and the mixture was stirred at room temperature (23 °C) for 3 hours. Then, 60 mL of ethyl acetate and dilute hydrochloric acid were added, and liquid separation was performed. The solution of the obtained organic layer was concentrated and subjected to column purification to obtain the compound (2-1-f).
[0371] <STEP3>
[0372] 5.0 g of the compound (2-1-d) obtained above and 7.2 g of the compound (2-1-f) were mixed in 50 mL of chloroform. Then, 3.4 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 0.1 g of N,N-dimethyl-4-aminopyridine were added, and the mixture was stirred at room temperature (23 °C) for 3 hours. Then, the solid was removed by filtration and the obtained solution was subjected to column purification to obtain the specific compound (2-1).
[0373] The 1H-NMR (Nuclear Magnetic Resonance) data of the obtained compound (2-1) are shown below.
[0374] 1 H-NMR (CDC13) δ (ppm) = 0.92 (m, 8H), 1.21 - 1.29 (m, 12H), 1.61 (m, 8H), 1.74 (m, 8H), 2.21 (m, 4H), 2.50 (m, 2H), 2.76 (m, 8H), 2.86 (s, 6H), 3.88 - 4.17 (10H), 5.84 (d, 1H), 6.13 (q, 1H), 6.42 (d, 1H), 7.11 (s, 2H)
[0375] [Synthesis of the specific compound (2-2)]
[0376] A specific compound (2-2) was synthesized according to the following scheme.
[0377] [Chemical formula 20]
[0378]
[0379] Except that the compound (2-1-c) and the compound (2-1-d) used in the synthesis of the specific compound (2-1) were changed to the compound (2-2-a) and the compound (2-2-b) shown in the above scheme, the specific compound (2-2) was obtained in the same manner as the synthesis of the specific compound (2-1) as shown in the above scheme.
[0380] The 1 1H-NMR data of the obtained specific compound (2-2) are shown below.
[0381] 1 1H-NMR (CDCl3) δ (ppm) = 0.92 (m, 4H), 1.21 - 1.29 (m, 8H), 1.51 (m, 4H), 1.60 (m, 4H), 1.74 (m, 4H), 2.21 (m, 4H), 2.35 (s, 3H), 2.50 (m, 2H), 2.56 (s, 3H), 2.76 (m, 8H), 2.86 (s, 6H), 3.88 - 4.17 (14H), 5.84 (d, 1H), 6.13 (q, 1H), 6.42 (d, 1H), 6.88 (s, 4H), 7.12 - 7.20 (m, 5H)
[0382] (Synthesis of specific compound (2-3))
[0383] Except that the compound (2-3-c) shown below was used instead of the compound (2-2-c) used in the synthesis of the specific compound (2-2), the following specific compound (2R3) was obtained in the same manner as the synthesis of the specific compound (2-2).
[0384] [Chemical formula 21]
[0385]
[0386] 〔Synthesis of specific compound (2-4)〕
[0387] Except that the compound (2-4-e) shown below was used instead of the compound (2-1-e) used in the synthesis of the specific compound (2-1), the following specific compound (2-4) was obtained in the same manner as the synthesis of the specific compound (2-1).
[0388] [Chemical formula 22]
[0389]
[0390] [Synthesis of Specific Compound (2-5)]
[0391] The following specific compound (2-5) was obtained in the same manner as the synthesis of specific compound (2-1), except that compound (2-5-e) shown below was used instead of compound (2-1-e) used in the synthesis of specific compound (2-1).
[0392] [Chemical Formula 23]
[0393]
[0394]
[0395] [Synthesis of Specific Compound (2-1-7)]
[0396] The following specific compound (2-1-7) was obtained in the same manner as the synthesis of specific compound (2-1), except that compound (2-1-7-a) shown below was used instead of compound (2-1-d) used in the synthesis of specific compound (2-1) and compound (2-1-7-b) shown below was used instead of compound (2-1-f).
[0397] [Chemical Formula 24]
[0398]
[0399] [Synthesis of Specific Compound (2-1-10)]
[0400] The following specific compound (2-1-10) was obtained in the same manner as the synthesis of specific compound (2-1), except that compound (2-1-10-f) shown below was used instead of compound (2-1-f) used in the synthesis of specific compound (2-1).
[0401] [Chemical Formula 25]
[0402]
[0403] [Example 1]
[0404] [Production of Optical Film]
[0405] A polymerizable liquid crystal composition having the following composition was prepared, and a glass substrate with a rubbed polyimide alignment film (SE-150 manufactured by NISSAN CHEMICAL INDUSTRIES, LTD.) was coated by spin coating.
[0406] The coating film was subjected to an alignment treatment at the temperatures shown in Table 1 below to form a liquid crystal layer.
[0407] Then, it was cooled to the exposure temperature described in Table 1 below and alignment fixation was performed by ultraviolet irradiation of 1000 mJ / cm 2 to form an optically anisotropic film, and an optical film was produced.
[0408]
[0409] Inverse wavelength dispersion liquid crystal compound (1-1)
[0410] [Chemical formula 26]
[0411]
[0412] Specific compound (2-1)
[0413] [Chemical formula 27]
[0414]
[0415] Fluorine-containing compound A
[0416] [Chemical formula 28]
[0417]
[0418] [Examples 2 to 6]
[0419] An optical film was produced in the same manner as in Example 1, except that the inverse wavelength dispersion liquid crystal compound or the specific compound was changed to the compound shown in Table 1 below.
[0420] In addition, for the specific compound, in the ring structure represented by M in the above formula (II), the maximum absorption wavelength of the aromatic ring represented by the central M is also as shown in Table 1 below.
[0421] [Comparative Example 1]
[0422] An optical film was produced in the same manner as in Example 1, except that the blending amount of the inverse wavelength dispersion liquid crystal compound was changed to the mass parts shown in Table 1 below and the specific compound was not blended.
[0423] [Comparative Example 2]
[0424] An optical film was produced in the same manner as in Example 6, except that the blending amount of the inverse wavelength dispersion liquid crystal compound was changed to the mass parts shown in Table 1 below and the specific compound was not blended.
[0425] <Retardation>
[0426] Regarding the produced optical film, using Axo Scan (OPMF-1, manufactured by Opto Science, Inc.), the retardation value (Re(450)) at a wavelength of 450 nm and the retardation value (Re(550)) at a wavelength of 550 nm were measured, and Re(450) / Re(550) was calculated. These results are shown in Table 1 below.
[0427] <Light resistance>
[0428] Regarding the produced optical film, a glass substrate was set in a xenon irradiator (SX75, manufactured by Suga Test Instruments Co., Ltd.) so that the coating film of the polymerizable liquid crystal composition became the irradiation surface, and a test of irradiating for 200 hours was carried out using a #275 filter.
[0429] The Re(550) of the optical film before the test and the Re(550) of the optical film after the test were measured, and the light resistance was evaluated according to the following criteria. The results are shown in Table 1 below.
[0430] A: The change amount of Re(550) after the test relative to Re(550) before the test is less than 5% of Re(550) before the test
[0431] B: The change amount of Re(550) after the test relative to Re(550) before the test is 5% or more and less than 15% of Re(550) before the test
[0432] C: The change amount of Re(550) after the test relative to Re(550) before the test is 15% or more of Re(550) before the test
[0433] <Orientation defect>
[0434] A 10 cm square was cut out from the obtained optical film, and using a polarizing microscope (LEXT, manufactured by OLYMPUS CORPORATION), the number of orientation defects on the screen was visually confirmed and evaluated according to the following evaluation criteria. The results are shown in Table 1 below.
[0435] (Evaluation criteria for orientation defects)
[0436] A: No defect
[0437] B: 1 to 10
[0438] C: 11 to 100
[0439] D: Orientation defects occur over the entire surface (> 100)
[0440]
[0441] The structures of the inverse wavelength dispersion liquid crystal compounds and the like in Table 1 above are as described below.
[0442] Inverse wavelength dispersion liquid crystal compound (1-1)
[0443] [Chemical formula 29]
[0444]
[0445] Inverse wavelength dispersion liquid crystal compound (1-2)
[0446] [Chemical formula 30]
[0447]
[0448] Specific compound (2-1)
[0449] [Chemical formula 31]
[0450]
[0451] Specific compound (2-2)
[0452] [Chemical formula 32]
[0453]
[0454] Specific compound (2-3)
[0455] [Chemical formula 33]
[0456]
[0457] Specific compound (2-4)
[0458] [Chemical formula 34]
[0459]
[0460] Specific compound (2-5)
[0461] [Chemical formula 35]
[0462]
[0463] From the results shown in Table 1 above, it can be seen that in the case where no specific compound is incorporated, orientation defects occur in the formed optically anisotropic film (Comparative Examples 1 and 2).
[0464] In contrast, it is known that in the case where a specific compound is incorporated together with the liquid crystal compound, generation of orientation defects in the formed optically anisotropic film can be suppressed (Examples 1 to 6). Moreover, it is known that the formed optically anisotropic film also has good light resistance.
Claims
1. A liquid crystal composition comprising a liquid crystal compound and a compound represented by the following formula (II), Here, in the formula (II), R 21 and R 22 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R 23 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group, SP 21 and SP 22 each independently represents a single bond or an alkylene group, where, The hydrogen atoms contained in the alkylene group may be substituted with fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, pentafluorothioalkyl groups, cyano groups, nitro groups, isocyano groups, isothiocyanato groups or alkyl groups having 1 to 20 carbon atoms. In addition, in the -CH2- constituting the alkylene group, one or more non-adjacent -CH2- may be substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR 24 -, -NH-CO-, -NR 25 -CO-, -NH-, -NR 26 -, or -C≡C-. R 24 ~R 26 represents a substituent. D 21 and D 22 each independently represents a single bond or a divalent linking group selected from -CO-, -O-, -S-, -C(=S)-, -CR 27 R 28 -, -CR 29 =CR 30 -, -NH-, -NR 31 -, or a combination of two or more thereof, and R 27 ~R 31 represents a substituent M represents an aromatic ring, alicyclic ring or heterocyclic ring which may have substituents, and at least one M in the formula (II) represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm. m represents an integer of 3 or more, and multiple Ms may be the same or different respectively. Multiple Ds 22 may be the same or different respectively, T represents a polymerizable group. At least one M in the formula (II) represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (M-1) to (M-7). Here, in the formulas (M-1) to (M-7), * indicates the bonding position with D 21 or D 22 of the bonding position Q 1 represents N or CH, Q 2 represents -S-, -O- or -N(R 6 ), where R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have substituents, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have substituents, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have substituents, and one or more of -CH2- in the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-. Z 1 , Z 2 and Z 3 each independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -OR 7 、-NR 8 R 9 、-SR 10 、-COOR 11 or-COR 12 , R 7 ~R 12 Each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 Can bond with each other to form aromatic rings, A 3 and A 4 each independently represents a group selected from the group consisting of -O-, -N(R 13 ), -, -S- and -CO-, and R 13 represents a hydrogen atom or a substituent X represents a Group 14 to 16 non-metal atom which may be bonded to a hydrogen atom or a substituent. D 7 and D 8 each independently represents a single bond or a divalent linking group of -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 -, or a combination of two or more of them, and R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 12 carbon atoms SP 3 and SP 4 each independently represents a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the linear or branched alkylene group having 1 to 12 carbon atoms are replaced by -O-, -S-, -NH-, -N(Q)- or -CO-, and Q represents a substituent L 3 and L 4 each independently represents a monovalent organic group, Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have substituents, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings. The aromatic rings in Ax and Ay may have substituents, and Ax and Ay may be bonded to form a ring. Q 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have substituents The content of the compound represented by the formula (II) is 0.05 to 20% by mass based on the total mass of the liquid crystal compound and the compound represented by the formula (II).
2. The liquid crystal composition according to claim 1, wherein, T in the formula (II) represents any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20). Herein, in the formulas (P-1) to (P-20), * represents the bonding position with SP 22 3. The liquid crystal composition according to claim 1 or 2, wherein, The liquid crystal compound has inverse wavelength dispersion.
4. The liquid crystal composition according to claim 1 or 2, wherein, The liquid crystal compound is a compound having any aromatic ring selected from the group consisting of the groups represented by the following formulas (Ar-1) to (Ar-7). Here, in the formulas (Ar-1) to (Ar-7), * represents the bonding position. Q 1 represents N or CH, Q 2 represents -S-, -O- or -N(R 6 ), where R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have substituents, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have substituents, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have substituents, and one or more of -CH2- in the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-. Z 1 , Z 2 and Z 3 each independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -OR 7 、-NR 8 R 9 、-SR 10 、-COOR 11 or-COR 12 , R 7 ~R 12 Each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 Can bond with each other to form aromatic rings, A 3 and A 4 each independently represents a group selected from the group consisting of -O-, -N(R 13 ), -, -S- and -CO-, and R 13 represents a hydrogen atom or a substituent X represents a Group 14 to 16 non-metal atom which may be bonded to a hydrogen atom or a substituent. D 7 and D 8 each independently represents a single bond or a divalent linking group selected from the group consisting of -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 -, or a combination of two or more thereof, and R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 12 carbon atoms SP 3 and SP 4 each independently represents a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the linear or branched alkylene group having 1 to 12 carbon atoms are substituted with -O-, -S-, -NH-, -N(Q)- or -CO-, and Q represents a substituent L 3 and L 4 each independently represents a monovalent organic group, Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have substituents or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings. The aromatic rings in Ax and Ay may have substituents, and Ax and Ay may be bonded to form a ring. Q 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have substituents.
5. The liquid crystal composition according to claim 1 or 2, wherein, The liquid crystal compound has a polymerizable group.
6. The liquid crystal composition according to claim 5, wherein, The polymerizable group represents any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20). Here, in the formulas (P-1) to (P-20), * represents the bonding position.
7. A compound which is a compound represented by the following formula (II), Herein, in the formula (II), R 21 and R 22 each independently represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, R 23 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group, SP 21 and SP 22 each independently represents a single bond or an alkylene group, wherein, The hydrogen atoms contained in the alkylene group may be substituted by fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, pentafluorothioalkyl groups, cyano groups, nitro groups, isocyano groups, isothiocyanato groups or alkyl groups having 1 to 20 carbon atoms. Further, in the -CH2- constituting the alkylene group, one or more non-adjacent -CH2- groups may be substituted by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -CO-NR 24 -, -NH-CO-, -NR 25 -CO-, -NH-, -NR 26 -, or -C≡C-, where R 24 to R 26 represents a substituent. D 21 and D 22 each independently represents a single bond or a divalent linking group selected from -CO-, -O-, -S-, -C(=S)-, -CR 27 R 28 -, -CR 29 =CR 30 -, -NH-, -NR 31 -, or a combination of two or more thereof, and R 27 ~R 31 represents a substituent M represents an aromatic ring, alicyclic ring or heterocyclic ring which may have substituents, and at least one M in the formula (II) represents an aromatic ring having a maximum absorption wavelength at 280 to 420 nm. m represents an integer of 3 or more, and multiple Ms may be the same or different respectively. Multiple Ds 22 may be the same or different respectively, T represents a polymerizable group. At least one M in the formula (II) represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (M-1) to (M-7). Here, in the formulas (M-1) to (M-7), *Indicates the bonding position with D 21 or D 22 of the bonding position Q 1 represents N or CH, Q 2 represents -S-, -O- or -N(R 6 ), where R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have substituents, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have substituents, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have substituents, and one or more of -CH2- in the alicyclic hydrocarbon group may be substituted with -O-, -S- or -NH-. Z 1 、Z 2 and Z 3 each independently represents a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -OR 7 、-NR 8 R 9 、-SR 10 、-COOR 11 or -COR 12 ,R 7 ~R 12 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 may be bonded to each other to form an aromatic ring. A 3 and A 4 each independently represents a group selected from the group consisting of -O-, -N(R 13 ), -, -S- and -CO-, and R 13 represents a hydrogen atom or a substituent X represents a Group 14 to 16 non-metal atom which may be bonded to a hydrogen atom or a substituent. D 7 and D 8 each independently represents a single bond or a divalent linking group of -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 -, or a combination of two or more thereof, and R 1 ~R 5 each independently represents a hydrogen atom, a fluorine atom or an alkyl group having 1 to 12 carbon atoms SP 3 and SP 4 each independently represents a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a divalent linking group in which one or more of -CH2- constituting the linear or branched alkylene group having 1 to 12 carbon atoms are replaced by -O-, -S-, -NH-, -N(Q)- or -CO-, and Q represents a substituent L 3 and L 4 each independently represents a monovalent organic group, Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, The aromatic rings in Ax and Ay may have substituents, and Ax and Ay may be bonded to form a ring, Q 3 represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have substituents.
8. The compound according to claim 7, wherein T in the formula (II) represents any one polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20), Herein, in the formulas (P-1) to (P-20), * represents the bonding position to SP 22 of.
9. An optically anisotropic film obtained by polymerizing the liquid crystal composition according to any one of claims 1 to 6.
10. The optically anisotropic film according to claim 9, wherein The optically anisotropic film satisfies the following formula (III), 0.50 < Re(450) / Re(550) < 1.00 (III) Here, in formula (III), Re(450) represents the in-plane retardation of the optically anisotropic film at a wavelength of 450 nm, and Re(550) represents the in-plane retardation of the optically anisotropic film at a wavelength of 550 nm.
11. An optical film having the optically anisotropic film according to claim 9 or 10.
12. A polarizing plate having the optical film according to claim 11 and a polarizer.
13. An image display device having the optical film according to claim 11 or the polarizing plate according to claim 12.
Citation Information
Patent Citations
JP1975048120A
Irokeshitaibutsurenzu
JP1976043918A
Photosensitive compound containing trichloromethyl group, manufacture and photosensitive mixture
JP1985105667A
Acylphosphine oxide compound*its manufacture and its use
JP1988040799B2
Static elimination lamp
JP1989088574A