Compound, composition, optically anisotropic body, and optical element

Abstract

A compound represented by the following general formula (I): [Formula 1] TIFF0007758260000055.tif20150 (The symbols in general formula (I) are as defined in the specification.)

Description

[Technical Field]

[0001] The present disclosure relates to a compound suitable for producing a liquid crystal composition, and a composition, an optically anisotropic body, and an optical element using the compound. [Background technology]

[0002] A compound having liquid crystallinity (hereinafter also referred to as a "liquid crystal compound") and a composition having liquid crystallinity (hereinafter also referred to as a "liquid crystal composition") can be used in a variety of applications. For example, Patent Document 1 describes a compound having a 2,6-naphthyl group as a compound having relatively high birefringence properties suitable for producing a liquid crystal composition, and as a compound having a sufficiently large phase width for processing, either by itself or in the form of such a composition. Furthermore, Patent Document 2 describes a tolan compound having a tolan skeleton (diphenylacetylene skeleton) and containing a sulfur atom, as a compound having a high refractive index anisotropy Δn. Liquid crystal compounds having a high refractive index anisotropy Δn are useful for various applications. Furthermore, even if a compound having a high refractive index anisotropy Δn itself does not have liquid crystal properties, it can be mixed with another compound having liquid crystal properties to form a liquid crystal composition having a high refractive index anisotropy Δn, which is useful for various applications. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Special Publication No. 2008-544954 [Patent Document 2] Japanese Patent Application Publication No. 2023-3351 Summary of the Invention [Problem to be solved by the invention]

[0004] However, the compound having a 2,6-naphthyl group specifically described in Patent Document 1 has problems such as insufficient refractive index anisotropy Δn (hereinafter also simply referred to as "Δn") and a high phase transition temperature. Tolan compounds such as those described in Patent Document 2 have problems with degradation and discoloration due to light due to the influence of the triple bond. There is a concern that the tolan skeleton containing the triple bond may be oxidatively decomposed in the presence of oxygen, such as tolan → diketone → carboxylic acid. Patent Document 2 describes that a light resistance test was conducted under oxygen-blocking conditions and found that the light resistance was good, but in practical use, light resistance in an air atmosphere (in the presence of oxygen) is required.

[0005] Furthermore, a problem has been that cured films of liquid crystal compositions having a high refractive index anisotropy Δn tend to be hard and brittle. Liquid crystal compositions having a high refractive index anisotropy Δn contain a large number of triple bonds and aromatic rings in the long axis direction of the molecules, and partial structures derived from the rigid molecular structure accumulate, which is thought to make the cured films thereof hard and brittle. Hard and brittle films have poor bending resistance, and are prone to cracking during the step of laminating to another optically anisotropic layer, the step of peeling off the substrate after transfer to another optically anisotropic layer, and during processing. Thus, there is a trade-off between high refractive index anisotropy and flexibility. A cured film of a liquid crystal composition containing a compound having a 2,6-naphthyl group, as specifically described in Patent Document 1, and a cured film of a liquid crystal composition containing a tolane compound, as described in Patent Document 2, were hard and brittle, and prone to cracking.

[0006] In view of the above-described circumstances, a first object of the embodiments of the present disclosure is to provide a compound having improved refractive index anisotropy Δn and light resistance in an air atmosphere, and a reduced phase transition temperature, a composition containing the compound, an optically anisotropic body, and an optical element.

[0007] In view of the above-described circumstances, a second object of the embodiments of the present disclosure is to provide an optical anisotropic body and an optical element that have an improved refractive index anisotropy Δn and that are suppressed from generating cracks. [Means for solving the problem]

[0008] The present inventors have conducted extensive research and have found that the above problems can be solved by the following means. That is, in order to achieve the first object, the first present disclosure includes the following aspects. [1] A compound represented by the following general formula (I):

[0009] [ka] (In general formula (I), Z 1 and Z 2 each independently represents a hydrogen atom, -CN, -NCS, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or a polymerizable group. R sp1 and R sp2 each independently represent an alkylene group having 1 to 20 carbon atoms in which one -CH2- or two or more non-adjacent -CH2- groups may each independently be replaced by O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, or -CH=CH-, or a single bond. S represents a sulfur atom. L 1 , L 2 , and L 3are each independently -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO2-CHRCHR-SO2-, -CH= represents CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CHRCHR-, -OCO-CHRCHR-, -CHRCHR-COO-, -CHRCHR-OCO-, -COO-CHR-, -OCO-CHR-, -CHR-COO-, -CHR-OCO-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=NN=CR-, -CF=CF-, or a single bond; R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and when there are multiple Rs, they may be the same or different. T 1 , and T 2 each independently represents a divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 20 carbon atoms which is unsubstituted or optionally substituted with one or more substituents E, and any carbon atom in the aromatic hydrocarbon group or alicyclic hydrocarbon group may be substituted with a heteroatom. A represents a group represented by any one of the following formulae (A-1) to (A-4), and may be substituted with one or more substituents E. Substituent E each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, or a polymerizable group. However, when the above groups described as substituent E have -CH2-, substituent E also includes groups in which at least one of the -CH2-s in the above groups is replaced with -O-, -CO-, or -CH=CH-. Furthermore, when the above group described as the substituent E has a hydrogen atom, the substituent E also includes a group in which at least one of the hydrogen atoms contained in the above group is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group. m and n each independently represent an integer of 0 to 3. m+n is an integer of 1 or more. L 1 , L 2 , T 1 , and T 2 When there are a plurality of each, they may be the same or different. When there are a plurality of E's, they may be the same or different.

[0010] [ka] (In formulas (A-1) to (A-4), W 1 ~W 16 are each independently, CR 1 or N, R 1 represents a hydrogen atom or the substituent E. Y 1 ~Y 2 are each independently, NR 2 , O or S, R 2 represents a hydrogen atom or the substituent E. *L 1 , L 2 , L 3 , or the bonding position with S.)

[0011] [2] The compound according to [1] above, wherein m in the general formula (I) represents 0, A represents a group represented by the formula (A-1), and the group represented by the formula (A-1) may be substituted with one or more substituents E. [3] The compound according to [1] or [2] above, which is represented by the following general formula (I-1):

[0012] [ka] (In general formula (I-1), Z 1 , Z 2 , R sp1 , R sp2 , S, L 2 , L 3 , T 2 and E each independently represent the same as defined in general formula (I). In general formula (I-1), the 2,6-naphthyl group may be substituted with one or more substituents E, k1 represents an integer of 0 to 6, and n' represents an integer of 0 to 2. L 2 and T 2 When there are a plurality of each, they may be the same or different. When there are a plurality of E's, they may be the same or different.

[0013] [4] The compound according to any one of the above items [1] to [3], which is represented by the following general formula (I-2):

[0014] [ka] (In general formula (I-2), Z 1 , Z 2 , R sp1 , R sp2 , S, L 2 , L 3 , T 2and E each independently represent the same as defined in general formula (I). In general formula (I-2), the 2,6-naphthyl group and the phenyl group may be substituted with one or more substituents E, k1 represents an integer of 0 to 6, and k2 represents an integer of 0 to 4. n' represents an integer of 0 to 2. 2 and T 2 When there are a plurality of each, they may be the same or different. When there are a plurality of E's, they may be the same or different.

[0015] [5] The compound according to any one of the above items [1] to [4], which has liquid crystal properties. [6] A composition comprising the compound according to any one of the above [1] to [5]. [7] The composition according to [6] above, further comprising a polymerization initiator. [8] The composition according to [6] or [7] above, further comprising a chiral agent. [9] An optically anisotropic medium in which the compound represented by the general formula (I) in the composition according to any one of the above items [6] to [8] is aligned.

[10] An optically anisotropic body which is a cured product of the composition described in [7] above.

[11] An optical element having an optically anisotropic layer formed using the composition according to any one of the above items [6] to [8].

[12] An optically anisotropic layer formed using the composition according to any one of [6] to [8] above, the optically anisotropic layer has an alignment pattern, The optical element, wherein the orientation pattern is an orientation pattern in which the direction of the optical axis derived from the liquid crystal compound contained in the composition is continuously rotated and changed along at least one direction in the plane.

[0016] In order to achieve the second object, the second present disclosure includes the following aspects.

[14] An optically anisotropic body which is a cured product of a polymerizable liquid crystal composition containing a partial structure of the following general formula (Ia):

[0017] [ka] (In general formula (Ia), the 2,6-naphthyl group may be substituted with one or more substituents E, and k1 represents an integer of 0 to 6. Substituent E each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, or a polymerizable group. However, when the above groups described as substituent E have -CH2-, substituent E also includes groups in which at least one of the -CH2-s in the above groups is replaced with -O-, -CO-, or -CH=CH-. Furthermore, when the above group described as the substituent E has a hydrogen atom, the substituent E also includes a group in which at least one of the hydrogen atoms contained in the above group is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group. ** indicates the bond position to other atoms.)

[0018]

[15] The optically anisotropic body according to

[14] , which is a cured product of a polymerizable liquid crystal composition containing 4% by mass or more of a compound having a partial structure of the general formula (Ia).

[16] 1205 cm measured by Fourier transform infrared spectrophotometer (FT-IR) using the ATR method -1 ~1225cm -1 The peak intensity of the SC bond (P1) located at 1600 cm -1 ~1650cm -1 The optically anisotropic body according to

[14] or

[15] , wherein the ratio (P1 / P2) of the peak intensity of the C=C bond located at (A) to the peak intensity (P2) of the C=C bond located at (B) is 0.30 or more and 1.80 or less.

[17] An optical element having the optically anisotropic body according to any one of the above items

[14] to

[16] as an optically anisotropic layer.

[18] An optically anisotropic layer comprising the optically anisotropic body according to any one of the above items

[14] to

[16] , the optically anisotropic layer has an alignment pattern, The optical element has an alignment pattern in which the direction of an optical axis derived from a compound having liquid crystal properties contained in the composition is continuously rotated and changed along at least one direction in a plane. [Effects of the Invention]

[0019] According to the first embodiment of the present disclosure, it is possible to provide a compound having improved refractive index anisotropy Δn and light resistance in an air atmosphere and a reduced phase transition temperature, a composition containing the compound, an optically anisotropic body, and an optical element. According to the second embodiment of the present disclosure, it is possible to provide an optical anisotropic body and an optical element that have an improved refractive index anisotropy Δn and are suppressed from generating cracks. DETAILED DESCRIPTION OF THE INVENTION

[0020] Hereinafter, embodiments and examples of the present disclosure will be described with reference to the drawings. However, the present disclosure can be implemented in many different forms, and should not be construed as being limited to the description of the embodiments and examples exemplified below. Furthermore, to clarify the explanation, the drawings may schematically depict the width, thickness, shape, etc. of each part compared to the actual form, but these are merely examples and do not limit the interpretation of the present disclosure. Furthermore, in this specification and each drawing, elements similar to those described above with reference to the previous drawings are given the same reference numerals, and detailed descriptions may be omitted as appropriate. Furthermore, for convenience of explanation, the terms "upper" and "lower" may be used in some cases, but the up-down direction may be reversed. "In this specification, when a certain component, such as a certain region, is said to be "on (or under)" another component, such as another component, or another region, unless otherwise specified, this includes not only the case where it is directly above (or directly below) the other component, but also the case where it is above (or below) the other component, i.e., the case where another component is included between the two components above (or below) the other component.

[0021] In the present disclosure, the alignment regulation force refers to the action of aligning the liquid crystal compound in the retardation layer in a specific direction. In the present disclosure, (meth)acrylic refers to either acrylic or methacrylic, and (meth)acrylate refers to either acrylate or methacrylate. Furthermore, in this specification, the terms "plate," "sheet," and "film" are not distinguished from one another solely on the basis of differences in name, and "film surface (plate surface, sheet surface)" refers to the surface that coincides with the planar direction of the target film-like (plate-like, sheet-like) member when the target film-like (plate-like, sheet-like) member is viewed overall and globally. In addition, in the present disclosure, the use of "to" indicating a numerical range means that the numerical values ​​before and after it are included as the lower limit and upper limit.

[0022] In the present disclosure, when the refractive index in the X-axis direction, which is the axial direction with the highest refractive index along the plane of the layer, is defined as Nx, the refractive index in the Y-axis direction along the plane of the layer and perpendicular to the X-axis is defined as Ny, and the refractive index in the thickness direction of the layer is defined as Nz, the in-plane retardation (Re) can be calculated from Nx, Ny, Nz, and the thickness d (nm) of the retardation layer by the following formula. In-plane phase difference (Re)=(Nx-Ny)×d In this specification, unless otherwise specified, the measurement of in-plane retardation and other measurements and evaluations are carried out in an atmosphere at a temperature of 23°C ± 5°C and a humidity of 40% to 65%. Furthermore, before measurement and evaluation, the sample is exposed to the above atmosphere for 30 minutes or more.

[0023] I. First Present Disclosure A. Compound The compound of the present disclosure is a compound represented by the following general formula (I):

[0024] [ka] (In general formula (I), Z 1 and Z 2 each independently represents a hydrogen atom, -CN, -NCS, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or a polymerizable group. R sp1 and R sp2 each independently represent an alkylene group having 1 to 20 carbon atoms in which one -CH2- or two or more non-adjacent -CH2- groups may each independently be replaced by O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, or -CH=CH-, or a single bond. S represents a sulfur atom. L 1 , L 2 , and L 3are each independently -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO2-CHRCHR-SO2-, -CH= represents CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CHRCHR-, -OCO-CHRCHR-, -CHRCHR-COO-, -CHRCHR-OCO-, -COO-CHR-, -OCO-CHR-, -CHR-COO-, -CHR-OCO-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=NN=CR-, -CF=CF-, or a single bond; R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and when there are multiple Rs, they may be the same or different. T 1 , and T 2 each independently represents a divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 20 carbon atoms which is unsubstituted or optionally substituted with one or more substituents E, and any carbon atom in the aromatic hydrocarbon group or alicyclic hydrocarbon group may be substituted with a heteroatom. A represents a group represented by any one of the following formulae (A-1) to (A-4), and may be substituted with one or more substituents E. Substituent E each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, or a polymerizable group. However, when the above groups described as substituent E have -CH2-, substituent E also includes groups in which at least one of the -CH2-s in the above groups is replaced with -O-, -CO-, or -CH=CH-. Furthermore, when the above group described as the substituent E has a hydrogen atom, the substituent E also includes a group in which at least one of the hydrogen atoms contained in the above group is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group. m and n each independently represent an integer of 0 to 3. m+n is an integer of 1 or more. L 1 , L 2 , T 1 , and T 2 When there are a plurality of each, they may be the same or different. When there are a plurality of E's, they may be the same or different.

[0025] [ka] (In formulas (A-1) to (A-4), W 1 ~W 16 are each independently, CR 1 or N, R 1 represents a hydrogen atom or the substituent E. Y 1 ~Y 2 are each independently, NR 2 , O or S, R 2 represents a hydrogen atom or the substituent E. *L 1 , L 2 , L 3 , or the bonding position with S.)

[0026] The compound represented by general formula (I) of the present disclosure contains, as a partial structure, a group represented by any one of formulas (A-1) to (A-4) and contains -S- (sulfur atom) as a bonding moiety, thereby improving refractive index anisotropy Δn and light resistance in an air atmosphere and decreasing the phase transition temperature. The group represented by any one of the formulas (A-1) to (A-4) contained as a partial structure is electron-rich and has an anisotropic molecular structure with a large difference in molecular length between the long axis direction and the short axis direction, and is therefore presumed to improve the refractive index anisotropy Δn, and also to improve the refractive index anisotropy Δn due to the synergistic effect of the polarizability of the sulfur atom and S-S interaction.Since the compound represented by general formula (I) of the present disclosure can have an oxygen atom in the molecule, it is thought that the improvement in orientational order due to S-O interaction also improves the refractive index anisotropy Δn. The group represented by any one of the formulas (A-1) to (A-4) contained as a partial structure is a rigid moiety, which poses a problem of easily increasing the phase transition temperature. In contrast, by including -S- (sulfur atom) as a bonding moiety within the molecule, the carbon-sulfur-carbon bond angle is significantly bent, suppressing packing due to intermolecular interactions and reducing crystallinity. This results in improved solubility and a lower phase transition temperature, improving coatability. Furthermore, the compound represented by general formula (I) of the present disclosure does not contain a triple bond, and therefore is inhibited from coloration and degradation due to light in oxygen, as seen in tolan compounds such as those described in Patent Document 2. Therefore, the compound represented by general formula (I) of the present disclosure has improved light resistance in an air atmosphere.

[0027] A cholesteric liquid crystal phase formed by using a compound having such a high refractive index anisotropy Δn has the advantage that the reflection band is widened and the reflection efficiency is improved. In addition, generally, if an optical anisotropic body is produced using a compound with a high refractive index anisotropy Δn, it can be made thin. In other words, if the compound of the present disclosure is used as an optical anisotropic body, it is possible to produce an optical element that is thin and has excellent light resistance. Furthermore, since the compound of the present disclosure has a reduced phase transition temperature, there is an advantage in that the options for the substrate on which the optical anisotropic body is provided are expanded.

[0028] Each symbol in general formula (I) will be explained in detail below. Z 1 and Z 2 each independently represents a hydrogen atom, -CN, -NCS, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or a polymerizable group. Examples of the alkoxy group having 1 to 10 carbon atoms include linear or branched alkoxy groups, such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, t-butoxy, n-pentoxy, etc. The alkoxy group having 1 to 10 carbon atoms may be an alkoxy group having 1 to 5 carbon atoms or may be an alkoxy group having 1 to 4 carbon atoms. The alkylthio group having 1 to 10 carbon atoms includes a linear or branched alkylthio group, such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, a t-butylthiooxy group, an n-pentylthio group, etc. The alkylthio group having 1 to 10 carbon atoms may be an alkylthio group having 1 to 5 carbon atoms or an alkylthio group having 1 to 4 carbon atoms.

[0029] When an optically anisotropic medium is produced from a composition containing the compound represented by general formula (I), the orientation state of the compound represented by general formula (I) can be fixed and the durability of the optically anisotropic medium can be improved. 1 and Z 2 It is preferable that at least one of Z represents a polymerizable group. 1 and Z 2 may both represent a polymerizable group. In terms of availability of raw materials and ease of synthesis, Z 1 and Z 2One of the groups may be a polymerizable group, and the other may be an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or a -CN (cyano group).

[0030] As the polymerizable group, any group used in a conventional polymerizable compound can be used without any limitation. The polymerizable groups preferably each independently represent a group selected from the following formulas (Z-1) to (Z-12): In the following formulas (Z-1) to (Z-12), * (asterisk) represents R sp1 or R sp2 The bond position is shown.

[0031] [ka] (In formulas (Z-1) to (Z-12), R z are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, or a trifluoromethyl group.

[0032] When using ultraviolet polymerization as the polymerization method, Z 1 is preferably the formula (Z-1), the formula (Z-2), the formula (Z-4), the formula (Z-6), or the formula (Z-9), more preferably the formula (Z-1), the formula (Z-4), or the formula (Z-9), and further preferably the formula (Z-1). In the formula (Z-1), R z It is particularly preferred that is a hydrogen atom, a methyl group or a trifluoromethyl group.

[0033] R sp1 and R sp2 each independently represent an alkylene group having 1 to 20 carbon atoms in which one -CH2- or two or more non-adjacent -CH2- groups may each independently be replaced by O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, or -CH=CH-, or a single bond.

[0034] R sp1 and R sp2From the viewpoint of availability of raw materials and ease of synthesis, it is more preferable that each independently represent an alkylene group having 1 to 12 carbon atoms, in which one -CH2- or two or more non-adjacent -CH2- groups may each independently be replaced by O-, -COO-, or -OCO-, or a single bond, it is even more preferable that each independently represent an alkylene group having 1 to 12 carbon atoms or a single bond, it is even more preferable that each independently represent an alkylene group having 1 to 10 carbon atoms or a single bond, and it is particularly preferable that each independently represent an alkylene group having 1 to 6 carbon atoms or a single bond, and when there are multiple groups, they may be the same or different. Z 1 and Z 2 are each independently a hydrogen atom, -CN, -NCS, an alkoxy group having 1 to 10 carbon atoms, or an alkylthio group having 1 to 10 carbon atoms, when the adjacent R sp1 and R sp2 are preferably each independently a single bond. 1 and Z 2 each independently represents a polymerizable group, the adjacent R sp1 and R sp2 are preferably each independently the alkylene group.

[0035] L 1 , L 2 , and L 3are each independently -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, - SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO2-CHRCHR-SO2-, -CH=C represents H-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CHRCHR-, -OCO-CHRCHR-, -CHRCHR-COO-, -CHRCHR-OCO-, -COO-CHR-, -OCO-CHR-, -CHR-COO-, -CHR-OCO-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=NN=CR-, -CF=CF-, or a single bond; R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and when there are multiple Rs, they may be the same or different. Also, L 1 and L 2 When there are a plurality of each of these, they may be the same or different. R preferably represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and even more preferably a hydrogen atom.

[0036] L 1 and L 2More specifically, in terms of liquid crystal properties, ease of raw material availability, and ease of synthesis, it is preferable that each independently represent -COO-, -OCO-, -OCH2-, -CHO-, -CF2O-, -OCF2-, -CH2CH2-, -CF2CF2-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -CH=CH-, -CF=CF-, or a single bond, and It is more preferable that it represents -, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -CH=CH-, or a single bond, it is even more preferable that it represents -COO-, -OCO-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -CH=CH-, or a single bond, it is even more preferable that it represents -COO-, -OCO-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, or a single bond, and it is particularly preferable that it represents -COO- or -OCO-.

[0037] L 3 From the viewpoint of availability of raw materials and ease of synthesis, preferably represents -O-, -S-, -OCH2-, -CHO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO- or a single bond, and more preferably represents -O-, -S-, -COO-, -OCO-, -O-CO-O- or a single bond. L 3 From the viewpoint of improving Δn, it is particularly preferable that represents —S—. R sp2 When represents a single bond, L 3 may be a single bond.

[0038] T 1 , and T 2are each independently a divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 20 carbon atoms, which may be unsubstituted or substituted with one or more substituents E, and any carbon atom in the aromatic hydrocarbon group or alicyclic hydrocarbon group may be substituted with a heteroatom, more specifically, any carbon atom in the aromatic hydrocarbon group or alicyclic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom. The aromatic hydrocarbon group may be an aromatic heterocyclic group, may have a fused ring structure, or may have a structure in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are fused. Note that T 1 and T 2 When each of them independently appears multiple times, they may be the same or different. When there are multiple E's, they may be the same or different.

[0039] Examples of the divalent aromatic hydrocarbon group which may be substituted with a heteroatom include a divalent aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted with a heteroatom. Examples of the aromatic hydrocarbon ring constituting the aromatic hydrocarbon group which may be substituted with a heteroatom include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring, and examples of the aromatic heterocycle include a furan ring, a pyridine ring, a pyrimidine ring, and a pyrazine ring.

[0040] Examples of the divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include a divalent cycloalkanediyl group having 3 to 20 carbon atoms and a divalent alicyclic fused ring group having 10 to 20 carbon atoms. Examples of the divalent cycloalkanediyl group having 3 to 20 carbon atoms include a cyclopropanediyl group; cyclobutanediyl groups such as a cyclobutane-1,2-diyl group and a cyclobutane-1,3-diyl group; cyclopentanediyl groups such as a cyclopentane-1,2-diyl group and a cyclopentane-1,3-diyl group; cyclohexane-1,2-diyl group, cyclohexane-1,3-diyl group, cyclohexane-1,4-diyl group, and the like. cyclohexanediyl groups such as cyclohexanediyl group; cycloheptanediyl groups such as cycloheptane-1,2-diyl group, cycloheptane-1,3-diyl group, and cycloheptane-1,4-diyl group; cyclooctanediyl groups such as cyclooctane-1,2-diyl group, cyclooctane-1,3-diyl group, cyclooctane-1,4-diyl group, and cyclooctane-1,5-diyl group; cyclodecane-1,2-diyl group cyclodecanediyl groups such as cyclodecane-1,3-diyl group, cyclodecane-1,4-diyl group, and cyclodecane-1,5-diyl group; cyclododecanediyl groups such as cyclododecane-1,2-diyl group, cyclododecane-1,3-diyl group, cyclododecane-1,4-diyl group, and cyclododecane-1,5-diyl group; cyclotetradecanediyl groups such as cyclotetradecane-1,2-diyl group, cyclotetradecane-1,3-diyl group, cyclotetradecane-1,4-diyl group, cyclotetradecane-1,5-diyl group, and cyclotetradecane-1,7-diyl group; cycloeicosanediyl groups such as cycloeicosane-1,2-diyl group and cycloeicosane-1,10-diyl group; and the like, and the cycloalkanediyl group may be unsubstituted or substituted with one or more substituents E. Any carbon atom of the cycloalkanediyl group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom, and examples thereof include a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, and a tetrahydrothiopyran-2,5-diyl group.

[0041] Examples of divalent alicyclic fused ring groups having 10 to 20 carbon atoms include decahydronaphthalene-2,5-diyl, decahydronaphthalene-2,6-diyl, and decahydronaphthalene-2,7-diyl groups such as decahydronaphthalene-2,5-diyl, decahydronaphthalene-2,6-diyl, and decahydronaphthalene-2,7-diyl groups; adamantanediyl groups such as adamantane-1,2-diyl and adamantane-1,3-diyl groups; and bicyclo[2.2.1]heptane-2,3-diyl, bicyclo[2.2.1]heptane-2,5-diyl, and bicyclo[2.2.1]heptane-2,6-diyl groups. The alicyclic fused ring groups may be unsubstituted or substituted with one or more substituents E. Furthermore, any carbon atom in the alicyclic fused ring group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom.

[0042] The divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 20 carbon atoms, which may be unsubstituted or substituted with one or more substituents E and may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom, may be a divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 18 carbon atoms, or may be a divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 12 carbon atoms.

[0043] Substituent E each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, or a polymerizable group. However, when the above groups described as substituent E have -CH2-, substituent E also includes groups in which at least one of the -CH2-s in the above groups is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above group described as the substituent E has a hydrogen atom, a group in which at least one of the hydrogen atoms contained in the above group is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group is also included in the substituent E. The polymerizable group here is the same as the above Z 1 and Z 2 The polymerizable group may be the same as that described above. The number of carbon atoms in the substituent E includes, for example, the number of carbon atoms in the carbonyl (C═O) in an alkanoyl group or an alkyloxycarbonyl group.

[0044] From the viewpoint of solvent solubility, the substituent E may be an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, a trifluoromethyl group, a hydroxy group, a carboxy group, a cyano group, a nitro group, or a halogen atom, or an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkanoyl group having 2 to 10 carbon atoms, an alkanoyloxy group having 2 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, a trifluoromethyl group, or a halogen atom. From the viewpoints of liquid crystallinity and visible light transmittance, the substituent E is preferably an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyl group having 2 to 6 carbon atoms, an alkanoyloxy group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, a trifluoromethyl group, a fluorine atom, or a chlorine atom.

[0045] Also, T 1 , and T 2 may each independently represent a group represented by any one of the following general formulae (B-1) to (B-10), or a group formed by linking two to three groups represented by any one of the following general formulae (B-1) to (B-10). 1 , and T 2 may be the same or different.

[0046] [ka] (In formulas (B-1) to (B-10), W 21 ~W 48 are each independently, CR 1 or N, R 1 represents a hydrogen atom or the substituent E. Y 11 ~Y 18 are each independently, NR 2 , O or S, R 2 represents a hydrogen atom or the substituent E. V 1 ~V 4 are each independently, CR 3 R 4 , N.R. 5 , O or S, R 3 ~R 5 each independently represents a hydrogen atom or the substituent E. *L 1 , L 2 , L 3 , or the bonding position with S.)

[0047] The group formed by linking two or more and three or less groups represented by any of the general formulae (B-1) to (B-10) may be a group formed by linking groups of the same structure, or may be a group formed by linking groups of different structures. For example, an example of a group formed by linking two groups represented by general formula (B-2) is a group represented by the following general formula (B-2-2).

[0048] [ka] (In formula (B-2-2), W 27 ~W 30 are each independently, CR 1 or N, R 1 represents a hydrogen atom or the substituent E; 27 ~W 30 may be the same or different. Adjacent substituents E may be bonded to each other to form a ring.

[0049] Furthermore, examples of the groups represented by general formulae (B-1) to (B-10) and (B-2-2) include groups represented by the following formulae (b-1-1) to (b-1-7), (b-2-1) to (b-2-7), (b-2-2-1) to (b-2-2-3), (b-3-1) to (b-3-6), (b-4-1) to (b-4-6), (b-5-1) to (b-5-6), (b-6-1) to (b-6-8), (b-7-1) to (b-7-6), (b-8-1) to (b-8-6), (b-9-1) to (b-9-4), and (b-10-1) to (b-10-8). In these formulas below, CR 1 R in 1 , and CR 3 R 4 R in 3 and R 4 is represented by a hydrogen atom, but each hydrogen atom may be replaced by the substituent E described above.

[0050] [ka]

[0051] [ka]

[0052] [ka]

[0053] In general formulas (B-1) to (B-10), W 21 ~W 48 are each independently, CR 1 or N, CR 1 In terms of availability of raw materials and ease of synthesis, it is preferable that R 1 When there are a plurality of, they may be the same or different. Y 11 ~Y 18 are each independently, NR 2 , O or S, and may represent O or S. R 2 When there are a plurality of, they may be the same or different. V 1 ~V 4 are each independently, CR 3 R 4 , N.R. 5 , O or S, CR 3 R 4 In general formula (B-10), R preferably represents 3 , R 4 , R 5 When there are a plurality of each, they may be the same or different.

[0054] In the group represented by the general formula (B-1), W in the general formula (B-1) is preferably 22 and W 23 Preferably, both do not represent N, and W 25 and W 26 Preferably, both do not represent N, and W 21 represents N, and W 22 ~W 26is CR 1 or W 21 ~W 26 All of these are CR 1 Preferably, W 21 ~W 26 All of these are CR 1 It is more preferable to represent

[0055] In the group represented by the general formula (B-2), W in the general formula (B-2) is preferably 27 and W 28 Preferably, both do not represent N, and W 29 and W 30 Preferably, both do not represent N, and W 27 represents N, and W 28 ~W 30 is CR 1 or W 27 ~W 30 All of these are CR 1 Preferably, W 27 ~W 30 All of these are CR 1 It is more preferable to represent

[0056] In the group represented by the general formula (B-3) or (B-4), Y in the general formula (B-3) and (B-4) is preferably selected from the viewpoints of availability of raw materials and ease of synthesis. 11 and Y 12 each independently represents O or S, W 31 and W 32 Preferably, each independently represents N.

[0057] In the group represented by the general formula (B-5) or (B-6), Y in the general formula (B-5) and (B-6) is preferably selected from the viewpoint of availability of raw materials and ease of synthesis. 13 and Y 14 each independently represents O or S, W 33 , W 34 , W 35 and W 36 are each independently, CR 1 It is preferred that

[0058] In the group represented by the general formula (B-7) or (B-8), Y in the general formula (B-7) is preferably 0 or 1 from the viewpoint of solvent solubility. 15 and Y 16 One of them is NR 2 And the other one represents O or S, or Y 15 and Y 16 Both are NR 2 represents W 37 , and W 38 are each independently, CR 1 It is preferable that Y in the general formula (B-8) represents 17 and Y 18 One of them is NR 2 And the other one represents O or S, or Y 17 and Y 18 Both are NR 2 represents W 39 , and W 40 are each independently, CR 1 It is preferred that

[0059] In the group represented by the general formula (B-9), W in the general formula (B-9) is 41 and W 42 and W 43 Preferably, both do not represent N, and W 44 and W 45 and W 46 Preferably, both do not represent N, and W 46 represents N, and W 41 ~W 45 is CR 1 or W 41 ~W 46 All of these are CR 1 Preferably, W 41 ~W 46 All of these are CR 1 It is more preferable to represent

[0060] In the group represented by the general formula (B-10), W 47 ~W 48 are each independently CR 1 and preferably represents V1 ~V 4 are each independently, CR 3 R 4 It is preferred that

[0061] In general formulas (B-1) to (B-10), R 1 ~R 6 each independently represents a hydrogen atom or the aforementioned substituent E. The substituent E may be the same as described above. In the general formulae (B-1) to (B-10), each formula preferably contains 0 to 2 substituents E, and more preferably 0 to 1 substituent E. In the general formulae (B-1) to (B-10), when a substituent E is contained in each formula, there are merits such as improved solvent solubility and improved orientation.

[0062] In view of the ease of obtaining raw materials for the compound represented by general formula (I) and the ease of synthesis, T 1 , and T 2 preferably each independently represents a group represented by the above general formula (B-1), (B-2), (B-2-2), (B-3) or (B-4), more preferably represents a group represented by the above general formula (B-1) or (B-2).

[0063] In the general formula (I), A represents a group represented by any one of the following formulae (A-1) to (A-4), and may be substituted with one or more substituents E.

[0064] [ka] (In formulas (A-1) to (A-4), W 1 ~W 16 are each independently, CR 1 or N, R 1 represents a hydrogen atom or the substituent E. Y 1 ~Y 2 are each independently, NR 2 , O or S, R 2represents a hydrogen atom or the substituent E. *L 1 , L 2 , L 3 , or the bonding position with S.)

[0065] In the group represented by the general formula (A-1), W in the general formula (A-1) is preferably 2 and W 3 Preferably, both do not represent N, and W 5 and W 6 Preferably, both do not represent N, and W 1 represents N, and W 2 ~W 6 is CR 1 or W 1 ~W 6 All of these are CR 1 Preferably, W 1 ~W 6 All of these are CR 1 It is more preferable to represent

[0066] In the group represented by the general formula (A-2), W in the general formula (A-2) is preferably 7 and W 8 Preferably, both do not represent N, and W 9 and W 10 Preferably, both do not represent N, and W 11 and W 12 Preferably, both do not represent N, and W 13 and W 14 Preferably, both do not represent N, and W 14 represents N, and W 7 ~W 13 is CR 1 or W 7 ~W 14 All of these are CR 1 Preferably, W 7 ~W 14 All of these are CR 1 It is more preferable to represent

[0067] In the group represented by the general formula (A-3) or (A-4), Y in the general formula (A-3) and (A-4) is preferably selected from the viewpoints of availability of raw materials and ease of synthesis. 1 and Y 2 each independently represents O or S, W 15 and W 16 Preferably, each independently represents N.

[0068] In formulas (A-1) to (A-4), R 1 When there are a plurality of, they may be the same or different. In general formulas (A-1) to (A-4), R 1 each independently represents a hydrogen atom or the aforementioned substituent E. The substituent E may be the same as described above. In the general formulae (A-1) to (A-4), each formula preferably contains 0 to 1 substituent E, and may contain 0 substituent E. In the general formulae (A-1) to (A-4), R 1 may all be hydrogen atoms.

[0069] A may be represented by the formula (A-1) in terms of more excellent refractive index anisotropy, and in the formula (A-1), W 1 represents N, and W 2 ~W 6 is CR 1 or W 1 ~W 6 All of these are CR 1 Preferably, W 1 ~W 6 All of these are CR 1 It is more preferable to represent

[0070] In order to improve the solvent solubility and orientation of the compound represented by general formula (I), T 1 , T 2 and A, at least one of which preferably has the substituent E.

[0071] m and n each independently represent an integer of 0 to 3. m+n is an integer of 1 or more. m+n is an integer of 6 or less, but may be an integer of 4 or less, or may be an integer of 2 or less. It is preferable that S and A are adjacent to each other, since this facilitates an improvement in Δn and also facilitates an improvement in light resistance in air.

[0072] A may be the formula (A-1) above, since the refractive index anisotropy is more excellent.

[0073] When m represents 0, A represents a group represented by formula (A-1), and the group represented by formula (A-1) may be substituted with one or more substituents E, the presence of a bond between the group represented by formula (A-1), such as a naphthyl group, and S (sulfur atom) is preferred, since it is easy to improve Δn and light resistance in air. When a sulfur atom is substituted on the group represented by formula (A-1), the interaction between the sulfur atom and the group represented by formula (A-1) is weaker than that of an oxygen atom, and the electron donating ability is weaker, which is thought to suppress oxidation of the group represented by formula (A-1).In addition, since the valence of the sulfur atom can take a high valence state from divalent to tetravalent to hexavalent, the sulfur atom is thought to trap oxidation by air, thereby protecting the group represented by formula (A-1), which is important for optical properties.

[0074] The compound represented by the general formula (I) may be a compound represented by the following general formula (I-1), since it is easy to improve Δn and light resistance in air.

[0075] [ka] (In general formula (I-1), Z 1 , Z 2 , R sp1 , R sp2 , S, L 2 , L 3 , T 2and E each independently represent the same as defined in general formula (I). In general formula (I-1), the 2,6-naphthyl group may be substituted with one or more substituents E, k1 represents an integer of 0 to 6, and n' represents an integer of 0 to 2. L 2 and T 2 When there are a plurality of each, they may be the same or different. When there are a plurality of E's, they may be the same or different.

[0076] In the general formula (I-1), T bonded to —COO— bonded to a naphthyl group 2 is preferably a group represented by any one of the general formulae (B-1) to (B-10) above, and more preferably a group represented by any one of the general formulae (B-1), (B-2), (B-2-2), (B-3) and (B-4) above, from the viewpoint of liquid crystal properties.

[0077] The compound represented by the general formula (I) may be a compound represented by the following general formula (I-2), which is particularly favorable in that it is easy to improve Δn, light resistance in air, and solvent solubility.

[0078] [ka] (In general formula (I-2), Z 1 , Z 2 , R sp1 , R sp2 , S, L 2 , L 3 , T 2 and E each independently represent the same as defined in general formula (I). In general formula (I-2), the 2,6-naphthyl group and the phenyl group may be substituted with one or more substituents E, k1 represents an integer of 0 to 6, and k2 represents an integer of 0 to 4. n' represents an integer of 0 to 2. 2 and T 2 When there are a plurality of each, they may be the same or different. When there are a plurality of E's, they may be the same or different.

[0079] In the general formulae (I-1) and (I-2), k1 represents an integer of 0 to 6. From the viewpoint of availability of raw materials and ease of synthesis, k1 may be an integer of 0 to 3, an integer of 0 to 2, or 0 or 1, or may be 0. In the general formula (I-2), k2 represents an integer of 0 to 4. From the viewpoints of availability of raw materials and ease of synthesis, k2 may be an integer of 0 to 2, or may be 0 or 1. When k2 is 1, it is preferable from the viewpoint of orientation. In the general formulae (I-1) and (I-2), n' represents an integer of 0 to 2. n' may be 1 or 2, or may be 1, from the viewpoint of solvent solubility and phase transition temperature.

[0080] In the general formulae (I-1) and (I-2), Z 1 , Z 2 , R sp1 , R sp2 , S, L 2 , L 3 , T 2 and E each independently represent the same as defined in general formula (I), and may be the same as above.

[0081] In the general formulas (I-1) and (I-2), Z is preferably used because it can fix the alignment state of the compound represented by general formula (I) and improve the durability of the optically anisotropic medium. 1 It is preferable that Z represents a polymerizable group. 1 is more preferably represented by formula (Z-1), and in formula (Z-1), R z It is particularly preferred that is a hydrogen atom, a methyl group or a trifluoromethyl group.

[0082] In the general formulas (I-1) and (I-2), from the viewpoint of availability of raw materials, R sp1 preferably represents an alkylene group having 1 to 6 carbon atoms, and more preferably represents an alkylene group having 2 to 6 carbon atoms.

[0083] In the general formulae (I-1) and (I-2), the substituent E may be the same as described above, but from the viewpoints of liquid crystallinity and visible light transmittance, it is preferably an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyl group having 2 to 6 carbon atoms, an alkanoyloxy group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, a trifluoromethyl group, a fluorine atom, or a chlorine atom, and more preferably an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyloxy group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, or a fluorine atom.

[0084] In the general formula (I-1), specific examples when k1 is 0 include compounds represented by the following Lc-1 to Lc-80. sp1 and R sp2 In the formula, n represents 1 to 20, but n is preferably 2 or more, more preferably 4 or more, and on the other hand, n is preferably 12 or less, more preferably 10 or less, and may be 6 or less. Also, Z 1 and Z 2 In the formula (Z-1), R z are each independently preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom. In the following chemical formulas, Me represents a methyl group.

[0085] [Table 1]

[0086] [Table 2]

[0087] Furthermore, representative structural formulas of the compounds represented by general formula (I) are shown below, but are not limited to these.

[0088] [ka]

[0089] [ka]

[0090] [ka]

[0091] [ka]

[0092] [ka]

[0093] The compound represented by general formula (I) can be produced, for example, by the following production method: The production method can be an appropriate combination of known organic synthesis reactions (e.g., condensation reaction, esterification reaction, Williamson reaction, Ullmann reaction, Wittig reaction, Schiff base formation reaction, benzylation reaction, Sonogashira reaction, Suzuki-Miyaura reaction, Negishi reaction, Kumada reaction, Hiyama reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, aldol reaction, Duff reaction, etc.) described in, for example, Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, New Experimental Chemistry Lectures, etc., depending on the structure of the compound. Specific examples of the synthesis of the compound represented by formula (I) will be shown in the examples below. Each intermediate used in the production may be a commercially available product or may be synthesized by a conventional method.

[0094] In the present disclosure, the structure of a compound can be analyzed by an appropriate combination of nuclear magnetic resonance spectroscopy (NMR), pyrolysis gas chromatography mass spectrometry (Py-GC-MS), matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOFMS), and the like.

[0095] The compound represented by general formula (I) may or may not have liquid crystallinity, but preferably has liquid crystallinity. When the compound represented by general formula (I) has liquid crystallinity, it is preferable that the compound represented by general formula (I) is easily aligned when an optically anisotropic layer is prepared from a composition containing the compound represented by general formula (I), and a desired alignment pattern can be easily prepared. However, even if the compound represented by general formula (I) itself does not have liquid crystallinity, it can be mixed with another compound having liquid crystallinity to form a liquid crystal composition, and a desired alignment pattern can be produced.

[0096] A compound having liquid crystallinity means that the compound has the property of exhibiting an intermediate phase between a crystalline phase (low temperature side) and an isotropic phase (high temperature side) when the temperature is changed. As a specific observation method, the optical anisotropy and fluidity derived from the liquid crystal phase can be confirmed by observing the compound under a polarizing microscope while heating or cooling it on a hot stage or the like.

[0097] The phase transition temperature of the compound represented by general formula (I) may be 40° C. or higher but lower than 110° C., or may be 100° C. or lower, or may be 90° C. or lower, so as to broaden the range of substrates that can be used and to facilitate handling. If the liquid crystal compound is solid at room temperature, it will be excellent in the drying step in the production process, in weighing during ink preparation, and in stability during storage. When the compound represented by the general formula (I) has liquid crystallinity, the phase transition temperature is a solid-liquid phase transition temperature, and when the compound represented by the general formula (I) does not have liquid crystallinity, the phase transition temperature is a solid-liquid phase transition temperature.

[0098] In the present disclosure, the phase transition temperature of the compound represented by general formula (I) is measured using a differential scanning calorimeter (DSC). The measurement is performed in accordance with JIS K7121-1987, Section 8. The phase transition temperature is the extrapolated melting onset temperature (Tim) according to JIS K7121-1987, Section 9.1(2). However, the heating and cooling program (heating rate, cooling rate, heating start temperature, and end temperature) is performed as follows. Five mg of the sample to be measured is sealed in an aluminum sample pan and set in the DSC. Under a nitrogen atmosphere, the pan is cooled from 25°C to -10°C at a rate of -25°C / min and maintained at -10°C for 15 minutes. Then, in the first heating run, the pan is heated from -10°C to 150°C at a rate of 10°C / min and maintained at 150°C for 1 minute. Then, in the first cooling run, the pan is cooled from 150°C to -10°C at a rate of -10°C / min and maintained at -10°C for 10 minutes. Then, in the second heating run, the pan is heated from -10°C to 150°C at a rate of 10°C / min and maintained at 150°C for 1 minute. Then, in the second cooling run, the pan is cooled from 150°C to 25°C at a rate of -10°C / min. The endothermic onset temperature detected during the second heating, i.e., the extrapolated melting onset temperature (Tim), which is the temperature at the intersection of a straight line extending the low-temperature baseline toward the high-temperature side and a tangent drawn at the point where the slope of the curve on the low-temperature side of the melting peak is maximum, is taken as the phase transition temperature.

[0099] In addition, the DSC measurements in both the present examples and comparative examples were carried out with the upper limit temperature set to 150° C. However, in the case of a compound that starts to polymerize at temperatures up to 150° C., the upper limit temperature of the DSC measurement is changed to be lower than the polymerization initiation temperature of the compound. In this case, whether or not the compound is polymerized is observed according to the following steps i) to iii) to determine the upper limit temperature for DSC measurement. i) The temperature reached in the first heating run is set to 150°C, and if no peak is detected in the second heating run or the peak area is significantly smaller, a new DSC measurement is performed under conditions in which the temperature reached in the first heating run is 5°C lower. ii) If no peak is detected in the second heating cycle even after lowering the temperature reached in the first heating cycle by 5°C, or if the peak area is significantly smaller, perform DSC measurement again under conditions where the temperature reached in the first heating cycle is further lowered by 5°C. iii) Repeat step ii) above until a peak is detected during the second heating. The temperature at which a peak can be detected during the second heating is set as the upper limit temperature for DSC measurement (upper limit of heating temperature).

[0100] The compound represented by the general formula (I) has an improved birefringence (Δn). When a composition is prepared, a cured film (optically anisotropic layer) is formed, and the refractive index anisotropy (Δn) is measured by the method described in the Examples below, the refractive index anisotropy (Δn) is preferably 0.25 or more.

[0101] Furthermore, the compound represented by the general formula (I) is preferably soluble in at least one solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone at a concentration of 10% by mass or more, and more preferably soluble in at least 20% by mass, in order to broaden the range of substrates that can be used.

[0102] B. Composition The composition of the present disclosure will be described as a composition containing a compound represented by the general formula (I) (hereinafter also referred to as "the composition of the present disclosure"). The content of the compound represented by general formula (I) in the composition of the present disclosure is not particularly limited, and may be 4% by mass or more, 9% by mass or more, 20% by mass or more, 30% by mass or more, or 40% by mass or more, or may be 100% by mass or less, or 99% by mass or less, relative to the total mass of the solid content in the composition. The solid content refers to the components (non-volatile components) in the composition other than the solvent. Components other than the solvent are considered to be solids even if they are in a liquid state. The composition may contain one compound represented by general formula (I) alone or two or more compounds. When two or more compounds are used, the total content thereof is preferably within the above range.

[0103] The composition of the present disclosure preferably has liquid crystal properties. When the composition of the present disclosure has liquid crystallinity, it is preferable that when an optically anisotropic layer is produced from the composition, the compounds in the composition can be easily aligned, and a desired alignment pattern can be easily produced.

[0104] The term "liquid crystallinity" means that the composition has the property of exhibiting an intermediate phase between a crystalline phase (low temperature side) and an isotropic phase (high temperature side) when the temperature is changed. As a specific observation method, the optical anisotropy and fluidity derived from the liquid crystal phase can be confirmed by observing the composition under a polarizing microscope while heating or cooling it on a hot stage or the like.

[0105] The composition of the present disclosure is preferably a composition for forming an optically anisotropic layer.

[0106] The composition of the present disclosure may contain other ingredients in addition to the compound represented by general formula (I). The other components will be described below.

[0107] <Other liquid crystal compounds> The composition of the present disclosure may contain liquid crystal compounds other than the compound represented by general formula (I) (also referred to as "other liquid crystal compounds"). The other liquid crystal compound may be a rod-shaped liquid crystal compound or a discotic liquid crystal compound, but is preferably a rod-shaped liquid crystal compound, and is preferably a liquid crystal compound having a polymerizable group (other polymerizable liquid crystal compound).

[0108] Examples of other liquid crystal compounds that are rod-shaped liquid crystal compounds include rod-shaped nematic liquid crystal compounds. As the rod-shaped nematic liquid crystal compounds, azomethines, azoxy compounds, cyanobiphenyls, cyanophenyl esters, benzoic acid esters, cyclohexanecarboxylic acid phenyl esters, cyanophenylcyclohexanes, cyano-substituted phenylpyrimidines, alkoxy-substituted phenylpyrimidines, phenyldioxanes, tolanes, or alkenylcyclohexylbenzonitriles are preferred. As other liquid crystal compounds, not only low-molecular-weight liquid crystal compounds but also high-molecular-weight liquid crystal compounds can be used.

[0109] A liquid crystal compound having a polymerizable group can be obtained by introducing a polymerizable group into a liquid crystal compound. Examples of the polymerizable group include Z in the general formula (I). 1 and Z 2 Examples of the polymerizable groups include those exemplified in The number of polymerizable groups that the liquid crystal compound has is preferably 1 to 6, more preferably 1 to 3, and even more preferably 1 or 2.

[0110] The other liquid crystal compound preferably has a high refractive index anisotropy Δn. Specifically, the refractive index anisotropy Δn of the other liquid crystal compound used in combination is preferably 0.15 or more, more preferably 0.18 or more, and even more preferably 0.22 or more. There is no particular upper limit to the refractive index anisotropy Δn, but it is often 0.60 or less. Furthermore, by using a mixture of the compound represented by general formula (I) and other liquid crystal compounds, the crystallization temperature as a whole can be significantly lowered.

[0111] Other examples of liquid crystal compounds include compounds described in Makromol.Chem., Vol. 192, p. 59 (1991), Makromol.Chem., Vol. 190, p. 2255 (1989), Advanced Materials, Vol. 5, p. 107 (1993), U.S. Pat. No. 4,683,327, U.S. Pat. No. 5,622,648, U.S. Pat. No. 5,770,107, JP-A-11-513019, JP-A-2001-505879, JP-A-2001-527570, JP-A-6-16616, JP-A-7-110469, JP-A-11-80081, and JP-A-2001-328973. In addition, a polymerizable liquid crystal compound exhibiting reverse dispersion may be used, and specific examples thereof include the polymerizable liquid crystal compound represented by the general formula (1) described in International Publication No. 2019 / 074007, the liquid crystal compound represented by the general formula (II) of International Publication No. 2017 / 043438, Japanese Patent Nos. 5463666, 4186981, 5962760, and 5826759, 6568103, 6427340, JP-A-2016-166344, and the polymerizable liquid crystal compounds described in Recueil des Travaux Chimiques des Pays-Bas (1996), 115 (6), 321-328.

[0112] Examples of other liquid crystal compounds include compounds represented by the following general formula (II), which are different from the compounds represented by the formula (I).

[0113] [ka] (In general formula (II), Z 1 , Z 2 , R sp1 , and R sp2 are each independently defined as in the general formula (I). L 4 and L 5are each independently -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -S O-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO2-CHRCHR-SO2-, -CH=CH- represents COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CHRCHR-, -OCO-CHRCHR-, -CHRCHR-COO-, -CHRCHR-OCO-, -COO-CHR-, -OCO-CHR-, -CHR-COO-, -CHR-OCO-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=NN=CR-, -CF=CF-, -C≡C-, or a single bond; R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and when there are multiple Rs, they may be the same or different. T 3 each independently represents a divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 20 carbon atoms, which is unsubstituted or optionally substituted with one or more substituents E or a group selected from the following general formula (D-1), and any carbon atom in the aromatic hydrocarbon group or alicyclic hydrocarbon group may be substituted with a heteroatom: The substituent E is as defined above in the general formula (I). p represents an integer of 2 to 6. 4 and T 3 When there are a plurality of each of the groups, they may be the same or different. When there are a plurality of substituents E or groups selected from the following general formula (D-1), they may be the same or different.

[0114] [ka] (In general formula (D-1), G 1represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group may be unsubstituted or substituted with one or more of the substituents E; Q 1 represents an organic group having 2 to 30 carbon atoms and having an aromatic hydrocarbon group, any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom, and the aromatic hydrocarbon group may be unsubstituted or substituted with one or more of the substituents E; J 1 -O-, -S-, -COO-, -OCO-, -OCO-O-, -NQ 2 -,-N=CQ 2 -, -CO-NQ 2 -, -OCO-NQ 2 -or-O-NQ 2 - represents Q 2 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom), or -L 6 -R sp2 -Z 2 wherein the alkyl group, cycloalkyl group, cycloalkenyl group, and aromatic hydrocarbon group may each be unsubstituted or substituted by one or more of the substituents E, the alkyl group may be substituted by the cycloalkyl group or cycloalkenyl group, and one -CH2- or two or more non-adjacent -CH2- in the alkyl group each independently represent -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO -CH-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, one -CH2- or two or more non-adjacent -CH2- in the cycloalkyl or cycloalkenyl group may each independently be replaced by -O-, -CO-, -COO-, -OCO- or -O-CO-O-; L 6 , Rsp2 , and Z 2 are the L 5 , R sp2 , and Z 2 Each of the above L 5 , R sp2 , and Z 2 It may be the same as or different from Q. 1 and Q 2 may be bonded to form a ring.)

[0115] For a detailed description of the group selected from general formula (D-1), the detailed description of the group selected from general formula (D-1) described in WO 2019 / 074007 can be incorporated into the present specification. In addition, for a polymerizable liquid crystal compound having a group selected from general formula (D-1) as a substituent, the detailed description of the polymerizable liquid crystal compound represented by general formula (1) described in WO 2019 / 074007 can be incorporated into the present specification.

[0116] In general formula (II), Z 1 , Z 2 , R sp1 , R sp2 and the substituent E may each independently be the same as those described in the general formula (I) above. L 4 R sp1 L binds to 4 , and L 5 is preferably L in the general formula (I). 3 It may be similar to that described in R sp1 L not bound to 4 is preferably L in the general formula (I). 1 and L 2 It may be similar to that described in T 3 represents a divalent aromatic hydrocarbon group or alicyclic hydrocarbon group having 3 to 20 carbon atoms which may be unsubstituted or substituted with one or more substituents E, and any carbon atom in the aromatic hydrocarbon group or alicyclic hydrocarbon group may be substituted with a heteroatom.3 represents T in the general formula (I). 1 and T 2 In view of the ease of obtaining raw materials for the compound represented by general formula (II) and the ease of synthesis, 3 preferably each independently represent a group represented by the above general formula (B-1), (B-2), (B-2-2), (B-3), (B-4) or (B-10), more preferably represent a group represented by the above general formula (B-1), (B-2), (B-2-2) or (B-10). Preferably, p is an integer of 3 or more, and may be an integer of 5 or less.

[0117] When the composition of the present disclosure contains other liquid crystal compounds, the content of the other liquid crystal compounds in the composition is not particularly limited, but may be 95% by mass or less, 90% by mass or less, 80% by mass or less, or 60% by mass or less, based on the total mass of the solid contents in the composition. The content of the other liquid crystal compounds in the composition may be 0% by mass or more, or 1% by mass or more, based on the total mass of the solid contents in the composition. In the composition of the present disclosure, the other liquid crystal compounds may be used alone or in combination of two or more. When two or more liquid crystal compounds are used, the total content thereof is preferably within the above range.

[0118] <Polymerization initiator> The compositions of the present disclosure may also include a polymerization initiator. The polymerization initiator can be appropriately selected depending on the polymerizable group contained in the composition. The polymerization initiator is preferably a photopolymerization initiator capable of initiating a polymerization reaction upon irradiation with ultraviolet light. In this embodiment, the photopolymerization initiator can be appropriately selected from conventionally known photopolymerization initiators. Specific examples of such photopolymerization initiators include aromatic ketones, such as thioxanthone, α-aminoalkylphenones, α-hydroxyketones, acylphosphine oxides, oxime esters, aromatic onium salts, organic peroxides, thio compounds, hexaarylbiimidazole compounds, ketoxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds. Among these, at least one selected from the group consisting of acylphosphine oxide-based polymerization initiators, α-aminoalkylphenone-based polymerization initiators, α-hydroxyketone-based polymerization initiators, and oxime ester-based polymerization initiators is preferred, as it hardens the coating film to its interior and improves durability.

[0119] Examples of the acylphosphine oxide polymerization initiator include bis(2,4,6-trimethylbenzoyl)-phenyl-phosphine oxide (e.g., trade name: Omnirad819, manufactured by IGM RESINS BV), bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphenylphosphine oxide, and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (trade name: Omnirad TPO H, manufactured by IGM RESINS BV).

[0120] Furthermore, examples of the α-aminoalkylphenone polymerization initiator include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (e.g., Omnirad907, manufactured by IGM RESINS BV), 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (e.g., Omnirad369, manufactured by IGM RESINS BV), and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone (Omnirad379EG, manufactured by IGM RESINS BV).

[0121] Examples of the α-hydroxyketone polymerization initiator include 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl}-2-methyl-propan-1-one (for example, trade name: Omnirad127, manufactured by IGM RESINS BV), 2-hydroxy-4'-hydroxyethoxy-2-methylpropiophenone (for example, trade name: Omnirad2959, manufactured by IGM RESINS BV), 1-hydroxy-cyclohexyl-phenyl-ketone (for example, trade name: Omnirad184, manufactured by IGM RESINS BV), and oligo{2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone} (for example, trade name: ESACURE ONE, manufactured by IGM RESINS BV).

[0122] Examples of the oxime ester polymerization initiator include 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (trade name: Irgacure OXE-01, manufactured by BASF), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(o-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF), and methanone, ethanone, 1-[9-ethyl-6-(1,3-dioxolane, 4-(2-methoxyphenoxy)-9H-carbazol-3-yl]-, 1-(o-acetyloxime) (trade name ADEKA OPT-N-1919, manufactured by ADEKA Corporation).

[0123] When the composition of the present disclosure contains a polymerization initiator, the content of the polymerization initiator in the composition is not particularly limited, but is preferably 0.1% by mass to 20% by mass, and more preferably 1% by mass to 8% by mass, relative to the total mass of the compound represented by general formula (I) (when the composition contains other liquid crystal compounds, relative to the total mass of the compound represented by general formula (I) and the other liquid crystal compounds). The composition of the present disclosure may use one type of polymerization initiator alone or two or more types. When two or more types are used, the total content thereof is preferably within the above range.

[0124] <Chiral Agents> The composition of the present disclosure may include a chiral agent. When the composition of the present disclosure includes a chiral agent, it can form a cholesteric phase. The type of chiral agent is not particularly limited. The chiral agent may be liquid crystalline or non-liquid crystalline. The chiral agent generally contains an asymmetric carbon atom. However, axially asymmetric compounds or planar asymmetric compounds that do not contain an asymmetric carbon atom can also be used as the chiral agent. Examples of axially asymmetric compounds or planar asymmetric compounds include binaphthyl, helicene, paracyclophane, and derivatives thereof. The chiral agent may have a polymerizable group. Specific examples of the chiral agent include those described in JP-A-08-245960, EP1816180, Japanese Patent No. 5284735, and Japanese Patent No. 4871139. When the composition of the present disclosure contains a chiral agent, the content of the chiral agent in the composition is not particularly limited, but is preferably 0.1% by mass to 15% by mass, and more preferably 1.0% by mass to 10% by mass, relative to the total mass of the compound represented by general formula (I) (when the composition contains other liquid crystal compounds, relative to the total mass of the compound represented by general formula (I) and the other liquid crystal compounds). The composition of the present disclosure may use one chiral agent alone or two or more chiral agents. When two or more chiral agents are used, the total content thereof is preferably within the above range.

[0125] <Solvent> The composition of the present disclosure may contain a solvent, if necessary, from the viewpoint of coatability. The solvent may be appropriately selected from conventionally known solvents capable of dissolving or dispersing the components contained in the polymerizable composition. Specific examples include hydrocarbon solvents such as hexane, cyclohexane, and toluene; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone; ether solvents such as tetrahydrofuran, 1,3-dioxolane, and propylene glycol monoethyl ether (PGME); alkyl halide solvents such as chloroform and dichloromethane; ester solvents such as ethyl acetate and propylene glycol monomethyl ether acetate; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and alcohol solvents such as methanol, ethanol, and propanol. In this embodiment, the solvent may be used alone or in combination as a mixed solvent of two or more solvents. When the composition of the present disclosure contains a solvent, the content of the solvent in the composition is preferably an amount that makes the solids concentration of the composition 0.5% by mass to 20% by mass, more preferably an amount that makes 1% by mass to 10% by mass. The composition of the present disclosure may use one solvent alone or two or more solvents. When two or more solvents are used, the total content thereof is preferably within the above range.

[0126] <Surfactant> The compositions of the present disclosure may include surfactants that contribute to the stable or rapid formation of a liquid crystal phase (e.g., nematic phase, cholesteric phase). Examples of surfactants include fluorine-containing (meth)acrylate polymers, compounds represented by general formulas (X1) to (X3) described in WO2011 / 162291, compounds represented by general formula (I) described in paragraphs 0082 to 0090 of JP-A No. 2014-119605, and compounds described in paragraphs 0020 to 0031 of JP-A No. 2013-47204. Examples of fluorine-containing (meth)acrylate polymers that can be used as surfactants include the polymers described in paragraphs 0018 to 0043 of JP-A No. 2007-272185. When the composition of the present disclosure contains a surfactant, the content of the surfactant is not particularly limited, but is preferably 0.001% by mass to 10% by mass, and more preferably 0.05% by mass to 3% by mass, relative to the total mass of the compound represented by general formula (I) (when the composition contains other liquid crystal compounds, relative to the total mass of the compound represented by general formula (I) and the other liquid crystal compounds). The composition of the present disclosure may use one surfactant alone or two or more surfactants. When two or more surfactants are used, the total content thereof is preferably within the above range.

[0127] In addition to the above, the composition of the present disclosure may contain other components such as an antioxidant, an ultraviolet absorber, a sensitizer, a stabilizer, a plasticizer, a chain transfer agent, a polymerization inhibitor, an antifoaming agent, a leveling agent, a thickener, a flame retardant, a surfactant, a dispersant, and a coloring material such as a dye or a pigment.

[0128] C. Optically anisotropic The optically anisotropic medium of the present disclosure is an optically anisotropic medium in which the compound represented by general formula (I) in the composition of the present disclosure is aligned. The optically anisotropic medium of the present disclosure may be an optically anisotropic medium that is a cured product of a composition containing the polymerization initiator of the present disclosure. The optically anisotropic body of the present disclosure may be an optically anisotropic body that is a composition containing the chiral agent of the present disclosure or a cured product thereof. The composition containing the chiral agent of the present disclosure as an optically anisotropic body may be a solidified product. The method for fixing the composition of the present disclosure is not particularly limited, and known methods can be used. For example, an embodiment may include a step of contacting a predetermined substrate with the composition to form a composition layer on the support (composition layer forming step), a step of subjecting the composition layer to a heat treatment to align the compound represented by general formula (I) (alignment step), and then a step of subjecting the composition layer to a curing treatment as needed (curing step). An alignment film is preferably provided on the support, and the steps may include a step of contacting the alignment film provided on the support with the composition to form a composition layer on the alignment film provided on the support (composition layer forming step), and a step of subjecting the composition layer to a heat treatment to align the compound represented by general formula (I) (alignment step). According to this embodiment, the compound represented by general formula (I) can be fixed in an aligned state, and an optically anisotropic body (for example, an optically anisotropic layer) can be formed. The term "optically anisotropic body" refers to a substance that has optical anisotropy. Having optical anisotropy means that the refractive index varies depending on the direction of polarization. For example, when an optically anisotropic body is placed between two polarizing plates in a crossed Nicol state and observed while rotating, incident light is transmitted at a specific angle and disappears at another angle.

[0129] The composition layer forming step is a step of contacting a predetermined support with a composition to form a composition layer on the support. The type of support to be used is not particularly limited, and examples thereof include known substrates (e.g., resin substrates, glass substrates, ceramic substrates, semiconductor substrates, and metal substrates). The method for bringing the support into contact with the composition is not particularly limited, and examples thereof include a method in which the composition is applied onto the support. As described above, it is preferable to provide an alignment film on the support, and the alignment film can be provided by a conventionally known method. The coating method may be appropriately selected as long as it can form a film with a desired thickness with high accuracy, and examples thereof include gravure coating, reverse coating, knife coating, dip coating, spray coating, air knife coating, spin coating, roll coating, printing, immersion and pulling up, curtain coating, die coating, casting, bar coating, extrusion coating, and E-type coating.

[0130] The orientation step is a step in which the composition layer is subjected to a heat treatment to orient the compound represented by general formula (I). The composition layer is heated at a temperature at which the compound represented by general formula (I) contained in the composition layer can be oriented. By this heat treatment, the compound represented by general formula (I) and, if necessary, other liquid crystal compounds further contained therein can be oriented and dried, and the oriented state can be maintained and fixed. The temperature at which orientation can be achieved varies depending on the substances in the composition and must be adjusted appropriately. For example, it is preferably performed within a range of 60°C or higher and 200°C or lower, and more preferably within a range of 60°C or higher and 100°C or lower. As the heating means, known heating and drying means can be appropriately selected and used. The heating time may be selected appropriately, for example, within the range of 10 seconds to 2 hours, preferably 20 seconds to 30 minutes.

[0131] By subjecting the composition layer to a heat treatment, the compound represented by general formula (I) is oriented, and a liquid crystal phase is formed. For example, when the composition layer contains a chiral agent, a cholesteric liquid crystal phase is formed.

[0132] After the orientation step, a curing step is carried out as needed. The method of curing treatment is not particularly limited, and examples thereof include photocuring treatment and heat curing treatment. Among these, photoirradiation treatment is preferred, and ultraviolet irradiation treatment is more preferred. As the light irradiation, ultraviolet irradiation is preferably used. For ultraviolet irradiation, ultraviolet rays emitted from light rays of an ultra-high pressure mercury lamp, a high pressure mercury lamp, a low pressure mercury lamp, a carbon arc, a xenon arc, a metal halide lamp, etc. can be used. The irradiation amount of the energy ray source may be appropriately selected, and the cumulative exposure amount at an ultraviolet wavelength of 365 nm is, for example, 10 mJ / cm. 2 More than 10000mJ / cm 2 It is preferable that the content is within the following range.

[0133] The cured product obtained by the above treatment corresponds to a layer in which a liquid crystal phase is fixed. In particular, when the composition contains a chiral agent, a layer in which a cholesteric liquid crystal phase is fixed is formed. It is not necessary for these layers to exhibit liquid crystallinity any more. More specifically, for example, the state in which the cholesteric liquid crystal phase is "fixed" is the most typical and preferred state in which the alignment of the compound represented by general formula (I) in the cholesteric liquid crystal phase is maintained. More specifically, it is preferable that the layer has no fluidity and can stably maintain the fixed alignment without causing any change in the alignment due to an external field or external force, usually within a temperature range of 0°C to 50°C, or under more severe conditions, within a temperature range of -30°C to 70°C.

[0134] The thickness of the optically anisotropic body (for example, the optically anisotropic layer) is not particularly limited and may be appropriately selected depending on the application. The thickness of the optically anisotropic layer may be, for example, 0.1 μm to 10 μm, 0.1 μm to 5 μm, or 0.5 μm to 3 μm.

[0135] The presence of the compound of the present disclosure contained in the composition of the present disclosure in the optical anisotropic body can be confirmed by collecting and analyzing a material from the optical anisotropic body. Analytical methods that can be used include HPLC, GPC, NMR, IR, pyrolysis GC-MS, LC-MS, TOF-MS, TOF-SIMS, and combinations of these. Furthermore, peaks and amounts of bonds and functional groups derived from the liquid crystal components contained in the optical anisotropic body can be confirmed using X-ray photoelectron spectroscopy (XPS), infrared spectroscopy (IR), and Raman spectroscopy. The structure of the components contained in the optical anisotropic body can be analyzed by combining the results of these analyses.

[0136] D. Optical Elements The optical element of the present disclosure is an optical element having an optically anisotropic layer formed using the composition of the present disclosure described above. The optical element of the present disclosure has an optically anisotropic layer formed using the composition of the present disclosure, the optically anisotropic layer has an alignment pattern, The optical element may be an optical element in which the orientation pattern is an orientation pattern in which the direction of the optical axis derived from the liquid crystal compound contained in the composition is continuously rotated and changed along at least one direction in the plane. The orientation pattern is preferably an orientation pattern in which the direction of the optical axis derived from the compound represented by general formula (I) is continuously rotated along at least one direction in the plane, or an orientation pattern in which the directions of the optical axes derived from the compound represented by general formula (I) and other liquid crystal compounds are continuously rotated along at least one direction in the plane. The optical element of the present disclosure has an orientation pattern in which the direction of the optical axis is continuously rotated along at least one direction in the plane, thereby enabling the diffracting of light incident on the optical element. The compound represented by general formula (I) is a compound having a high refractive index anisotropy Δn, and therefore can increase the diffraction efficiency. The optical element of the present disclosure can be appropriately applied to conventionally known optical elements that include the optically anisotropic layer. Furthermore, the optical element of the present disclosure can be appropriately applied to conventionally known optical elements, as long as the optically anisotropic layer has an orientation pattern in which the direction of the optical axis derived from the liquid crystal compound contained in the composition is continuously rotated and changed along at least one direction in the plane. For the optical element, reference can be made to, for example, the descriptions in paragraphs

[0067] to

[0107] of International Publication No. 2020 / 022496 and the descriptions in paragraphs

[0035] to

[0072] of Japanese Patent Application Laid-Open No. 2017-31379.

[0137] The optical element of the present disclosure can be applied as an optical member for an augmented reality (AR) image projection device or the like. The optical element of the present disclosure may also be used as a light guide element including the optical element and a light guide plate.

[0138] II. Second Present Disclosure The second optically anisotropic body of the present disclosure is a cured product of a polymerizable liquid crystal composition containing a partial structure of the following general formula (Ia).

[0139] [ka] (In general formula (Ia), the 2,6-naphthyl group may be substituted with one or more substituents E, and k1 represents an integer of 0 to 6. Substituent E each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, or a polymerizable group. However, when the above groups described as substituent E have -CH2-, substituent E also includes groups in which at least one of the -CH2-s in the above groups is replaced with -O-, -CO-, or -CH=CH-. Furthermore, when the above group described as the substituent E has a hydrogen atom, the substituent E also includes a group in which at least one of the hydrogen atoms contained in the above group is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group. ** indicates the bond position to other atoms.)

[0140] The second optically anisotropic body of the present disclosure is a cured product of a polymerizable liquid crystal composition, and by containing a partial structure of general formula (Ia), it has an improved refractive index anisotropy Δn and is suppressed from generating cracks. The partial structure of general formula (Ia) has an electron-withdrawing group, -COO-, at the 2-position of naphthalene and an electron-donating group, -S-, at the 6-position of naphthalene, resulting in a structure that allows for wider π-conjugated resonance. Since the optically anisotropic material of the second disclosure contains the partial structure of general formula (Ia), the -S-naphthalene-COO- structure expands the π electrons toward the 2- and 6-positions of naphthalene, improving the refractive index toward the 2- and 6-positions of naphthalene and increasing the refractive index anisotropy Δn. It is also presumed that the high polarizability of the sulfur atom and the synergistic effect of intermolecular SS interactions also increase the refractive index anisotropy Δn. Furthermore, since the partial structure of general formula (Ia) contains a large bending angle between the -S- bond adjacent to naphthalene, it is presumed that sufficient extensibility can be obtained by stretching this bond even when deformation is applied. Therefore, it is presumed that by including the partial structure of general formula (Ia), the optically anisotropic body of the second aspect of the present disclosure has improved refractive index anisotropy Δn and is less susceptible to cracking. The second optically anisotropic body of the present disclosure has improved flex resistance, is less susceptible to cracking even when flexed, and has excellent lamination properties and processability.

[0141] The optically anisotropic body of the second present disclosure may have an in-plane retardation Re and layer thickness (nm) measured by the method described below, and Δn calculated by the following formula, such that Δn is 0.25 or more. Δn=Re / layer thickness (nm) Re is measured at a wavelength of 550 nm using a retardation measurement device (RETS-100 manufactured by Otsuka Electronics Co., Ltd.) at a set temperature of 25°C. The average value of the measurements taken at three locations is used as the measurement result. When the optically anisotropic material is laminated with a substrate having retardation, such as polyethylene terephthalate (PET), a measurement sample is prepared by transferring the optically anisotropic material onto a glass plate with an adhesive layer (optical adhesive, Panaclean PD-S1 manufactured by Panac Corporation) that does not have retardation, and the in-plane retardation Re is measured. (Re measurement conditions) Retardation measurement range: Rotating analyzer method Measurement spot diameter: φ5mm Tilt angle range: 0° Measurement wavelength range: 400nm to 800nm (layer thickness measurement) The thickness of the optically anisotropic body (optically anisotropic layer) is determined by photographing a cross section of the optically anisotropic body using a scanning transmission electron microscope (STEM) (S-4800, manufactured by Hitachi High-Technologies Corporation), measuring the thickness of the optically anisotropic body at 10 points on the cross-sectional image, and calculating the arithmetic mean value of the layer thicknesses at those 10 points. Cross-sectional photographs of optically anisotropic bodies are taken as follows. First, a 1 mm x 10 mm sample is cut out and embedded in embedding resin to create a block. Then, uniform, hole-free slices with a thickness of 70 nm to 100 nm are cut from this block using a standard slice preparation method. An ion milling device (IM-4000II, manufactured by Hitachi High-Technologies Corporation) is used to prepare the slices. These uniform, hole-free slices are used as the measurement sample. Cross-sectional photographs of the measurement sample are then taken using a scanning transmission electron microscope (STEM). When taking these cross-sectional photographs, STEM observations are performed with the detector set to "TE," the acceleration voltage set to "30 kV," and the emission current set to "10 μA." The magnification is adjusted between 5,000x and 200,000x, as appropriate, while adjusting the focus and observing whether the contrast and brightness of each layer can be distinguished.

[0142] The optically anisotropic body of the second disclosure may be one that shows no cracks when observed with a 10x magnifying glass at the bent portion when the cylindrical mandrel method conforming to JIS-K5600-5-1:1999 is used and the mandrel has a diameter of 3 mm.

[0143] The second optically anisotropic body of the present disclosure is a cured product of a polymerizable liquid crystal composition containing the partial structure of general formula (Ia). The presence of the partial structure of general formula (Ia) in the second optical anisotropic body of the present disclosure can be analyzed by detecting fragment ions of the partial structure of general formula (Ia) or fragment ions of a structure containing the partial structure of general formula (Ia) by time-of-flight secondary ion mass spectrometry (TOF-SIMS). (TOF-SIMS measurement conditions) TOF-SIMS equipment: ION-TOF TOF.SIMS 5 Primary ion species: Bi3 ++ Primary ion accelerating voltage: 25 kV Primary ion current value: 0.2 pA Measurement area: 200 μm x 200 μm (using a neutralization gun for charge correction) Number of scans: 64 scans

[0144] In the partial structure of general formula (Ia), the substituent E may be the same as the substituent E described in the first present disclosure. Among these, from the viewpoints of liquid crystallinity and visible light transmittance, the substituent E is preferably an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyl group having 2 to 6 carbon atoms, an alkanoyloxy group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, a trifluoromethyl group, a fluorine atom, or a chlorine atom, and more preferably an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyloxy group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, or a fluorine atom.

[0145] In the partial structure of the general formula (Ia), k1 represents an integer of 0 to 6. From the viewpoint of availability of raw materials and ease of synthesis, k1 may be an integer of 0 to 3, an integer of 0 to 2, or 0 or 1, or may be 0.

[0146] The second optically anisotropic body of the present disclosure may be a cured product of a polymerizable liquid crystal composition containing a compound containing the partial structure of general formula (Ia). The compound containing the partial structure of the general formula (Ia) does not need to have liquid crystallinity, but may be a liquid crystal compound or a polymerizable liquid crystal compound. The compound containing the partial structure of general formula (Ia) included in the optical anisotropic body of the second present disclosure may be a compound represented by general formula (I-1) or a compound represented by general formula (I-2). The compound represented by the general formula (I-1) and the compound represented by the general formula (I-2) may be the same as the compounds described in the first aspect of the present disclosure.

[0147] In the second optical anisotropic body of the present disclosure, the polymerizable liquid crystal composition containing the partial structure of general formula (Ia) includes a compound containing the partial structure of general formula (Ia), and includes at least a polymerizable liquid crystal compound. If the compound containing the partial structure of general formula (Ia) is a polymerizable liquid crystal compound, it does not need to further contain other polymerizable liquid crystal compounds.

[0148] In the optical anisotropic body of the second present disclosure, the components that can be contained in the polymerizable liquid crystal composition containing the partial structure of general formula (Ia) and the contents thereof may be the same as the components and the contents thereof described in the composition of the first present disclosure. The other liquid crystal compounds may be the same as those described in the composition of the first present disclosure. The compound represented by the general formula (II) may be a compound represented by the general formula (II) (however, different from a compound containing the partial structure of the general formula (Ia)). The cured product of the polymerizable liquid crystal composition, which is the second optically anisotropic body of the present disclosure, may not contain a polymerization initiator, since some polymerization initiators are decomposed.

[0149] In the second optically anisotropic medium of the present disclosure, it is preferable that the compound containing the partial structure of general formula (Ia) be contained in an amount of 4% by mass or more from the viewpoints of refractive index anisotropy and suppression of crack generation. In the second optical anisotropic body of the present disclosure, the compound containing the partial structure of general formula (Ia) may be 9% by mass or more, 30% by mass or more, 50% by mass or more, or 70% by mass or more, or may be 100% by mass or less, 99% by mass or less, or 97% by mass or less.

[0150] In the second optical anisotropic body of the present disclosure, from the viewpoint of refractive index anisotropy and crack generation suppression, the 1205 cm -1 ~1225cm -1 The peak intensity of the SC bond (P1) located at 1600 cm -1 ~1650cm -1 The ratio (P1 / P2) of the peak intensity of the C=C bond (P2) located at the position of the carbon atom may be 0.30 or more and 1.8 or less. The P1 / P2 ratio may be 0.45 or more, 0.80 or more, or 1.00 or more. 1205cm -1 ~1225cm -1 The peak of the SC bond located at 1600 cm represents the SC bond with the aromatic ring. -1 ~1650cm -1 The peak of the C=C bond located at represents the C=C bond of the aromatic ring. Therefore, the peak intensity ratio P1 / P2 represents the relative amount of aromatic rings bonded to sulfur atoms, and a P1 / P2 ratio of 0.30 or more is preferable from the viewpoint of refractive index anisotropy and crack suppression. On the other hand, a P1 / P2 ratio of 1.80 or less is preferable from the viewpoint of surface hardness of the film. In addition, from the viewpoint of refractive index anisotropy and crack suppression, the 1205 cm -1 ~1225cm -1 The peak intensity of the SC bond (P1) located at 1700 cm -1 ~1750cm -1 The ratio (P1 / P3) of the peak intensity of the C=O bond (P3) located at the position of the carbon atom may be 0.10 or more and 0.80 or less. The P1 / P3 ratio may be 0.30 or more, or may be 0.50 or more. Furthermore, from the viewpoint of refractive index anisotropy and crack suppression, the 1205 cm -1 ~1225cm -1 The peak intensity of the SC bond (P1) located at 1600 cm -1 ~1650cm -1 The peak intensity of the C=C bond (P2) located at 1700 cm-1 ~1750cm -1 The ratio {P1 / (P2+P3)} of the peak intensity of the C=O bond (P3) located at the position of the carbon atom to the sum of the peak intensities of the C=O bonds located at the positions of the carbon atom may be 0.10 or more and 0.80 or less. The P1 / (P2+P3) may be 0.15 or more, or may be 0.30 or more.

[0151] The peak intensity measured by FT-IR is the absorbance (unitless) at the peak position. The peak intensity is determined by measuring the height from the background to the peak top in the obtained spectrum using the analysis software provided with the measuring device. (FT-IR measurement conditions) The surface of the optically anisotropic medium is measured by the ATR method using a Fourier transform infrared spectrophotometer (FT-IR). If necessary, the surface of the optically anisotropic medium is exposed before measurement. Measurement equipment: Fourier transform infrared spectrophotometer (JASCO Corporation, FT-IR6100 equipped with ATR-PRO470-H) Light source: High-brightness ceramic light source Detector: DLATGS Beam splitter: Ge / KBr Measurement mode: ATR method (diamond prism, incident angle 45°) Measurement wavenumber range: 4,000 cm -1 ~400cm -1 Resolution: 4cm -1 Measurement spot diameter: φ1.5mm Accumulation count: 32 times

[0152] The optical anisotropic body of the second disclosure can be produced by preparing a polymerizable liquid crystal composition containing the partial structure of general formula (Ia) and using the polymerizable liquid crystal composition in the same manner as described for the optical anisotropic body of the first disclosure.

[0153] In the second optically anisotropic body of the present disclosure, the cured product of the polymerizable liquid crystal composition containing the partial structure of general formula (Ia) corresponds to a layer formed by fixing a liquid crystal phase. In particular, when the composition contains a chiral agent, a layer formed by fixing a cholesteric liquid crystal phase is formed. It is not necessary for these layers to exhibit liquid crystallinity any more. More specifically, for example, the state in which the cholesteric liquid crystal phase is "fixed" is the most typical and preferred state in which the alignment of the compound containing the partial structure of general formula (Ia) in the cholesteric liquid crystal phase is maintained.

[0154] The thickness of the optically anisotropic body (e.g., optically anisotropic layer) of the second present disclosure is not particularly limited and may be appropriately selected depending on the application. The thickness of the optically anisotropic layer may be, for example, 0.1 μm to 10 μm, 0.1 μm to 5 μm, or 0.5 μm to 3 μm.

[0155] The molecular orientation of the optical anisotropic body of the second disclosure can be analyzed by X-ray diffraction analysis to determine whether the body is a cured product of a polymerizable liquid crystal composition. Furthermore, the components contained in the optical anisotropic body of the second disclosure can be confirmed by collecting and analyzing materials from the optical anisotropic body. Analytical methods that can be used include HPLC, GPC, NMR, IR, pyrolysis GC-MS, LC-MS, TOF-MS, TOF-SIMS, and combinations of these. Furthermore, peaks and amounts of bonds and functional groups derived from the liquid crystal components contained in the optical anisotropic body can be confirmed by X-ray photoelectron spectroscopy (XPS), infrared spectroscopy (IR), and Raman spectroscopy. The structure of the components contained in the optical anisotropic body can be analyzed by combining the results of these analyses.

[0156] The optical element of the second present disclosure is an optical element having the optical anisotropic body of the second present disclosure as an optically anisotropic layer. The optical element according to the second aspect of the disclosure includes the optically anisotropic body according to the second aspect of the disclosure as an optically anisotropic layer, the optically anisotropic layer has an alignment pattern, The optical element may be an optical element in which the orientation pattern is an orientation pattern in which the direction of the optical axis derived from the compound having liquid crystal properties contained in the composition is continuously rotated and changed along at least one direction in the plane. The optical element of the second aspect of the present disclosure can be appropriately applied to conventionally known optical elements that include the optically anisotropic layer. The optical element of the second present disclosure may be similar to the optical element described in the first present disclosure. [Example]

[0157] Each compound was analyzed using a Bruker AVANCE (400MHz) spectrometer. 1 The chemical structure was confirmed by 1 H NMR measurement. In this disclosure, the in-plane retardation Re and various FT-IR parameters in the following evaluation items refer to the average values ​​of measurements taken at three locations unless otherwise specified. The three measurement locations are the centers of measurement at the three intersections of a line dividing a rectangular measurement sample into four equal parts in the vertical direction and a line dividing the sample into two equal parts in the horizontal direction. The vertical direction of the rectangle is the long side direction. If the measurement sample has a shape other than a rectangle, such as a circle, ellipse, triangle, or pentagon, a rectangle with the largest area inscribed in the shape is drawn, and measurements are taken at three locations on the rectangle using the above method.

[0158] Example I Series: First Present Disclosure [Production Example 1: Production of Compound A-1] Compound A-1 was synthesized according to the following scheme.

[0159] [ka]

[0160] (1) Synthesis of Compound 1 6-Hydroxy-2-naphthoic acid (7.5 g, 39.9 mmol) and 1,4-diazabicyclo[2.2.2]octane (DABCO) (13.4 g, 119.6 mmol) were dissolved in dimethylformamide (DMF) (75 mL). N,N-dimethylthiocarbamoyl chloride (14.5 g, 119.6 mmol) was added to the resulting solution and stirred at 65 °C for 3 hours. The resulting solution was cooled to room temperature, and 1 M hydrochloric acid (150 mL) was added. The resulting mixture was filtered and washed with water. The resulting solid was reslurried and purified in methanol to give compound 1 (10.6 g, 38.5 mmol). The yield was 96.5%.

[0161] (2) Synthesis of Compound 2 Compound 1 (8.0 g, 29.1 mmol) was stirred at 230° C. for 3 hours. The resulting residue was purified by flash column chromatography to obtain Compound 2 (7.9 g, 28.6 mmol) in a yield of 98.5%.

[0162] (3) Synthesis of Compound 3 Compound 2 (7.9 g, 28.6 mmol) was dissolved in methanol (40 mL). To the resulting solution was added an aqueous solution of potassium hydroxide (4.3 g, 85.8 mmol) (water; 40 mL), and the mixture was stirred at 70°C for 3 hours. The resulting solution was cooled to room temperature, methanol was evaporated under reduced pressure, and 1 M hydrochloric acid (120 mL) was added to the resulting residue. The resulting mixture was filtered, and the residue was washed with water to give compound 3 (5.6 g, 27.3 mmol). The yield was 95.5%.

[0163] (4) Synthesis of Compound 4 Compound 3 (10 g, 47.0 mmol), 4-chlorobutyl acetate (21.2 g, 141.0 mmol), potassium carbonate (19.4 g, 141.0 mmol), and potassium iodide (0.8 g, 4.7 mmol) were mixed with dimethylacetamide (DMAc) (200 mL). The resulting mixture was stirred at 80°C for 3 hours. A solution of sodium hydroxide (9.4 g, 235.0 mmol) in 200 mL of water and 50 mL of methanol was added to the mixture, and the mixture was stirred at 80°C for 3 hours. The resulting mixture was cooled to room temperature, the methanol was evaporated under reduced pressure, and 1 M hydrochloric acid (500 mL) was added to the resulting residue. Water and ethyl acetate were added to the mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The resulting solid was reslurried and purified with diisopropyl ether to give compound 4 (12.4 g, 44.9 mmol). The yield was 95.5%.

[0164] (5) Synthesis of Compound 5 Compound 4 (10.0 g, 36.1 mmol) and N,N-dimethylaniline (6.6 g, 54.2 mmol) were dissolved in tetrahydrofuran (THF) (100 mL). The resulting solution was cooled to 10 °C, and acrylic acid chloride (4.9 g, 54.2 mmol) was added dropwise. The mixture was stirred at 10 °C for 1 hour. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The resulting residue was recrystallized using toluene to give compound 5 (11.8 g, 35.7 mmol). The yield was 98.0%.

[0165] (6) Synthesis of Compound A-1 Compound 5 (4.1 g, 12.5 mmol), methylhydroquinone (0.6 g, 5.0 mmol), and 4-dimethylaminopyridine (DMAP) (0.06 g, 0.5 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15 °C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise. The mixture was stirred at 15 °C for 3 hours. Methanol (120 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to give compound A-1 (3.7 g, 5.0 mmol). The yield was 99.5%. 1 H-NMR(CDCl3):δ=1.87(m,8H),2.31(s,3H),3.13(t,4H),4.21(t,4H),5.80(dd,2H),6.37(dd,2H),6.41(dd, 2H),7.24(m,5H),7.47(s,1H),7.49(s,1H),7.72(d,2H),7.85(d,2H),7.89(d,2H),8.20(m,2H),8.71(d,2H)

[0166] [ka]

[0167] [Production Example 2: Production of Compound A-2] Compound A-2 was synthesized according to the following scheme.

[0168] [ka]

[0169] (1) Synthesis of Compound 6 Compound 3 was synthesized in the same manner as in Preparation Example 1. DMAc (200 mL) was added to compound 3 (10 g, 47.0 mmol), 2-[2-(2-chloroethoxy)ethoxy]ethanol (7.9 g, 47.0 mmol), potassium carbonate (19.5 g, 141.0 mmol), and potassium iodide (0.8 g, 4.7 mmol). The resulting mixture was stirred at 80°C for 3 hours. A solution of sodium hydroxide (9.4 g, 235.0 mmol) in 200 mL of water and 50 mL of methanol was added to the resulting mixture, and the mixture was stirred at 80°C for 3 hours. The resulting mixture was cooled to room temperature, the methanol was evaporated under reduced pressure, and 1 M hydrochloric acid (500 mL) was added to the resulting residue. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent from the resulting organic layer was evaporated under reduced pressure. The obtained solid was purified by reslurrying in diisopropyl ether to obtain Compound 6 (14.6 g, 43.5 mmol) in a yield of 92.5%.

[0170] (2) Synthesis of Compound 7 Compound 6 (10 g, 29.7 mmol) and N,N-dimethylaniline (5.4 g, 44.6 mmol) were dissolved in THF (200 mL). The resulting solution was cooled to 10 °C, and acrylic acid chloride (4.0 g, 44.6 mmol) was added dropwise. The mixture was stirred at 10 °C for 1 hour. Water and ethyl acetate were added to the resulting mixture, and the reaction product was then extracted with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The resulting residue was recrystallized using toluene to give compound 7 (10.7 g, 24.5 mmol). The yield was 92.5%.

[0171] (8) Synthesis of Compound A-2 Compound 7 (4.9, 12.5 mmol), methylhydroquinone (0.6 g, 5.0 mmol), and DMAP (0.06 g, 0.5 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15 °C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise and stirred at 15 °C for 3 hours. Methanol (120 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to give compound A-2 (4.2 g, 4.8 mmol). The yield was 96.5%. 1 H-NMR(CDCl3):δ=3.09(t,4H),4.05(m,16H),4.19(t,4H),5.76(dd,2H),6.34(dd,2H),6.39(dd,2H),7 .22(m,5H),7.45(s,1H),7.47(s,1H),7.70(d,2H),7.83(d,2H),7.87(d,2H),8.18(m,2H),8.69(d,2H)

[0172] [Production Example 3: Production of Compound A-3] Compound 5 was synthesized in the same manner as in Preparation Example 1. Compound 5 (4.1 g, 12.5 mmol), 2-fluoro-1,4-benzenediol (0.6 g, 5.0 mmol), and DMAP (0.06 g, 0.5 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto. The mixture was stirred at 15°C for 3 hours. Methanol (120 mL) was added to the resulting mixture, and the mixture was filtered. The residue was washed with methanol to obtain Compound A-3 (3.4 g, 4.5 mmol). The yield was 90.5%. 1 H-NMR(CDCl3):δ=1.85(m,8H),3.12(t,4H),4.20(t,4H),5.81(dd,2H),6.34(dd,2H),6.42(dd,2H),7 .22(m,5H),7.40(s,1H),7.48(s,1H),7.72(d,2H),7.84(d,2H),7.88(d,2H),8.19(m,2H),8.70(d,2H)

[0173] [ka]

[0174] [Production Example 4: Production of Compound A-4] Compound 5 was synthesized in the same manner as in Preparation Example 1. Compound 5 (4.1 g, 12.5 mmol), methyl 2,5-dihydroxybenzoate (0.8 g, 5.0 mmol), and DMAP (0.06 g, 0.5 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto. The mixture was stirred at 15°C for 3 hours. Methanol (120 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to obtain Compound A-4 (3.6 g, 4.6 mmol). The yield was 91.5%. 1 H-NMR(CDCl3):δ=1.87(m,8H),3.13(t,4H),3.74(s,3H),4.21(t,4H),5.80(dd,2H),6.07(dd,2H),6.36(dd,2H),7 .36(d,1H),7.47(m,2H),7.55(m,1H),7.73(s,2H),7.83(d,2H),7.89(d,2H),8.01(d,1H),8.17(m,2H),8.73(m,2H)

[0175] [ka]

[0176] [Production Example 5: Production of Compound A-5] Compound 5 was synthesized in the same manner as in Preparation Example 1. Compound 5 (4.1 g, 12.5 mmol), 2-(4-hydroxyphenyl)ethanol (0.7 g, 5.0 mmol), and DMAP (0.06 g, 0.5 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto. The mixture was stirred at 15°C for 3 hours. Methanol (120 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to obtain Compound A-5 (3.5 g, 4.7 mmol). The yield was 93.0%. 1 H-NMR(CDCl3):δ=1.93(m,8H),3.16(t,2H),3.14(t,4H),4.26(t,4H),4.61(t,3H),5.84(dd,2H),6.11(dd,2H),6.40(dd,2 H),7.20(m,6H),7.38(d,2H),7.75(d,1H),7.80(m,1H),7.83(m,2H),8.00(dd,1H),8.18(dd,1H),8.51(s,1H),8.69(s,1H)

[0177] [ka]

[0178] [Production Example 6: Production of Compound A-6] Compound A-6 was synthesized according to the following scheme.

[0179] [ka]

[0180] (1) Synthesis of Compound 8 4-Hydroxybenzoic acid (1.4 g, 10 mmol) was dissolved in THF (14 mL) and cooled to 15 °C. To the resulting mixture, chloromethyl methyl ether (1.0 g, 12.0 mmol) and N,N-diisopropylethylamine (1.9 g, 15.0 mmol) were added and stirred at 15 °C for 1 hour. To the resulting mixture, 4-methylthiobenzoic acid (2.0 g, 12.0 mmol) and DMAP (0.1 g, 1.0 mmol) were added, followed by dropwise addition of N,N-diisopropylcarbodiimide (1.9 g, 15.0 mmol) and stirring at 15 °C for 3 hours. To the resulting mixture, 35% hydrochloric acid (10 mL) was added and stirred at 15 °C for 24 hours. Methanol (28 mL) was added to the resulting mixture, which was then filtered and washed with methanol. The resulting residue was recrystallized using DMF / methanol to give Compound 8 (2.6 g, 9.0 mmol) in a yield of 89.5%.

[0181] (2) Synthesis of Compound 9 Compound 5 was synthesized in the same manner as in Preparation Example 1. Compound 5 (1.8 g, 5.5 mmol), methylhydroquinone (0.6 g, 5.0 mmol), and DMAP (0.06 g, 0.5 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.8 g, 6 mmol) was added dropwise thereto. The mixture was stirred at 15°C for 3 hours. Methanol (120 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to give compound 9 (2.1 g, 4.9 mmol). The yield was 98.5%.

[0182] (3) Synthesis of Compound A-6 Compound 9 (0.4 g, 1.0 mmol), compound 8 (0.4 g, 1.5 mmol), and DMAP (0.01 g, 0.1 mmol) were dissolved in CHCl (2 mL). The resulting solution was cooled to 15 °C, and N,N-diisopropylcarbodiimide (0.3 g, 2.0 mmol) was added dropwise. The mixture was stirred at 15 °C for 3 hours. Methanol (10 mL) was added to the resulting mixture, and the mixture was filtered. The residue was washed with methanol to obtain compound A-6 (0.7 g, 0.9 mmol). The yield was 91.5%. 1 H-NMR(CDCl3):δ=1.96(m,4H),2.31(s,3H),2.65(s,3H),4.14(t,2H),4.27(t,2H),5.86(dd,1H),6.18(dd,1H),6.41(dd,1H),7.2 0(m,5H),7.34(dd,1H),7.42(dd,1H),7.58(dd,1H),7.79(d,1H),7.88(d,1H),7.95(d,1H),8.12(m,3H),8.20(d,2H),8.72(s,1H)

[0183] [Production Example 7: Production of Compound A-7] Compound 9 was synthesized in the same manner as in Preparation Example 6. Compound 9 (0.4 g, 1.0 mmol), 6-methoxy-2-naphthoic acid (0.3 g, 1.5 mmol), and DMAP (0.01 g, 0.1 mmol) were dissolved in CHCl (2 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.3 g, 2.0 mmol) was added dropwise thereto. The mixture was stirred at 15°C for 3 hours. Methanol (10 mL) was added to the resulting mixture, and the mixture was filtered. The residue was washed with methanol to obtain Compound A-7 (0.6 g, 1.0 mmol). The yield was 98.0%. 1 H-NMR(CDCl3):δ=1.86(m,4H),2.28(s,3H),3.12(t,2H),3.73(s,3H),4.23(t,2H),5.82(dd,1H),6.14(dd,1H),6.37(dd, 1H),7.23(m,2H),7.36(m,1H),7.48(m,2H),7.75(s,1H),7.88(m,4H),7.91(s,1H),8.20(d,2H),8.72(s,1H),8.81(s,1H)

[0184] [ka]

[0185] [Production Example 8: Production of Compound A-8] Compound 9 was synthesized in the same manner as in Preparation Example 6. Compound 9 (0.4 g, 1.0 mmol), 4-cyanobenzoic acid (0.2 g, 1.5 mmol), and DMAP (0.01 g, 0.1 mmol) were dissolved in CHCl (2 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.3 g, 2.0 mmol) was added dropwise thereto. The mixture was stirred at 15°C for 3 hours. Methanol (10 mL) was added to the resulting mixture, and the residue was filtered and washed with methanol to obtain Compound A-8 (0.5 g, 0.9 mmol). The yield was 93%. 1H-NMR (CDCl3): δ=1.89(m,4H),2.38(s,3H),3.23(t,2H),4.27(t,2H),5.81(dd,1H),6.11(dd,1H),6.41(dd,1H),7. 35(d,1H),7.36(dd,1H),7.42(dd,1H),7.79(s,1H),7.88(m,3H),7.98(s,1H),8.18(d,2H),8.35(d,2H),8.78(s,1H)

[0186] [ka]

[0187] [Production Example 9: Production of Compound A-9] Compound 5 was synthesized in the same manner as in Preparation Example 1. Compound 5 (1.5 g, 4.5 mmol), 4-cyano-4'-hydroxybiphenyl (0.6 g, 3.0 mmol), and DMAP (0.04 g, 0.3 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.8 g, 6.0 mmol) was added dropwise thereto. The mixture was stirred at 15°C for 3 hours. Methanol (120 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to obtain Compound A-9 (1.4 g, 2.7 mmol). The yield was 91.5%.

[0188] [ka]

[0189] [Production Example 10: Production of Compound A-10] Compound A-10 was synthesized according to the following scheme. 1 H-NMR(CDCl3):δ=1.87(m,4H),3.13(t,2H),4.21(t,2H),5.80(dd,1H),6.07(dd,1H),6.36(dd, 1H),7.38(t,2H),7.48(m,1H),7.66(m,7H),7.82(d,1H),7.88(d,1H),8.19(d,1H),8.73(s,1H)

[0190] [ka]

[0191] (1) Synthesis of Compound 10 6-Hydroxy-2-quinolinecarboxylic acid (18.9 g, 100.0 mmol) and DABCO (33.7 g, 300.0 mmol) were dissolved in DMF (200 mL). N,N-dimethylthiocarbamoyl chloride (37.1 g, 300.0 mmol) was added to the resulting solution and stirred at 65°C for 3 hours. The resulting solution was cooled to room temperature, and 1 M hydrochloric acid (450 mL) was added. The resulting mixture was filtered, and the residue was washed with water. The resulting solid was reslurried and purified in methanol to give compound 10 (26.9 g, 97.5 mmol). The yield was 97.5%.

[0192] (2) Synthesis of Compound 11 Compound 10 (26.9 g, 97.5 mmol) was stirred at 230° C. for 3 hours. The resulting residue was purified by flash column chromatography to give Compound 11 (26.9 g, 97.5 mmol) in a 100% yield.

[0193] (3) Synthesis of Compound 12 Compound 11 (22.1 g, 80.0 mmol) was dissolved in methanol (250 mL). To the resulting solution was added a potassium hydroxide (13.5 g, 240.0 mmol) aqueous solution (120 mL of water), and the mixture was stirred at 70°C for 3 hours. The resulting solution was cooled to room temperature, the methanol was evaporated under reduced pressure, and 1 M hydrochloric acid (300 mL) was added to the resulting residue. The resulting mixture was filtered, and the residue was washed with water to give compound 12 (15.8 g, 76.8 mmol). The yield was 96.0%.

[0194] (4) Synthesis of Compound 13 Compound 12 (14.4 g, 70.0 mmol), 4-chlorobutyl acetate (31.6 g, 210.0 mmol), potassium carbonate (29.0 g, 210.0 mmol), and potassium iodide (1.2 g, 7.0 mmol) were mixed with DMAc (150 mL). The mixture was stirred at 80°C for 3 hours. A solution of sodium hydroxide (14.0 g, 350.0 mmol) in 70 mL of water and 70 mL of methanol was added to the mixture, and the mixture was stirred at 80°C for 3 hours. The mixture was cooled to room temperature, the methanol was removed under reduced pressure, and 1 M hydrochloric acid (700 mL) was added to the residue. Water and ethyl acetate were added to the mixture, followed by extraction with ethyl acetate. The solvent in the organic layer was removed under reduced pressure. The solid was reslurried and purified with diisopropyl ether to give compound 13 (18.3 g, 66.1 mmol). The yield was 94.5%.

[0195] (5) Synthesis of Compound 14 Compound 13 (16.6 g, 60 mmol) and N,N-dimethylaniline (9.1 g, 75.0 mmol) were dissolved in THF (200 mL). The resulting solution was cooled to 10 °C, and acrylic acid chloride (6.8 g, 75.0 mmol) was added dropwise. The mixture was stirred at 10 °C for 1 hour. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The resulting residue was recrystallized from toluene to give compound 14 (19.5 g, 58.8 mmol). The yield was 98.0%.

[0196] (6) Synthesis of Compound A-10 Compound 14 (16.6 g, 50 mmol), methylhydroquinone (2.5 g, 20 mmol), and DMAP (2.4 g, 2.0 mmol) were dissolved in CHCl (50 mL). The resulting solution was cooled to 15 °C, and N,N-diisopropylcarbodiimide (7.6 g, 60.0 mmol) was added dropwise. The mixture was stirred at 15 °C for 3 hours. Methanol (1000 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to give compound A-10 (14.2 g, 18.9 mmol). The yield was 94.5%. 1H-NMR (CDCl3): δ=1.98(m,8H),2.45(s,3H),3.64(t,4H),4.78(t,4H),5.87(dd,2H),6.44(dd,2H),6. 48(dd,2H),7.53(m,5H),7.61(s,1H),7.63(s,1H),7.86(d,2H),7.97(d,2H),8.03(d,2H),8.33(m,2H)

[0197] [Production Example 11: Production of Compound A-11] Compound A-11 was synthesized according to the following scheme.

[0198] [ka]

[0199] (1) Synthesis of Compound 15 4-(4-Hydroxyphenyl)benzoic acid (6.4 g, 30.0 mmol) and DABCO (10.1 g, 90.0 mmol) were dissolved in DMF (300 mL). N,N-dimethylthiocarbamoyl chloride (11.1 g, 90 mmol) was added to the resulting solution, and the mixture was stirred at 65°C for 3 hours. The resulting solution was cooled to room temperature, and 1 M hydrochloric acid (150 mL) was added. The resulting mixture was filtered, and the residue was washed with water. The resulting solid was reslurried and purified in methanol to give compound 15 (8.7 g, 28.8 mmol). The yield was 96.0%.

[0200] (2) Synthesis of Compound 16 Compound 15 (8.7 g, 28.8 mmol) was stirred at 230° C. for 3 hours. The resulting residue was purified by flash column chromatography to give compound 16 (8.5 g, 28.1 mmol) in a yield of 97.5%.

[0201] (3) Synthesis of Compound 17 Compound 16 (7.5 g, 25.0 mmol) was dissolved in methanol (250 mL). To the resulting solution was added a potassium hydroxide (4.2 g, 75.0 mmol) aqueous solution (75 mL of water), and the mixture was stirred at 70°C for 3 hours. The resulting solution was cooled to room temperature, methanol was evaporated under reduced pressure, and 1 M hydrochloric acid (100 mL) was added to the resulting residue. The resulting mixture was filtered, and the residue was washed with water to give compound 17 (5.5 g, 18.9 mmol). The yield was 95.0%.

[0202] (4) Synthesis of Compound 18 Compound 17 (3.5 g, 15.0 mmol), 4-chlorobutyl acetate (6.8 g, 45.0 mmol), potassium carbonate (6.2 g, 45.0 mmol), and potassium iodide (0.2 g, 1.5 mmol) were mixed with DMAc (35 mL). The resulting mixture was stirred at 80°C for 3 hours. A solution of sodium hydroxide (3.0 g, 75.0 mmol) in 15 mL of water and 15 mL of methanol was added to the resulting mixture, and the mixture was stirred at 80°C for 3 hours. The resulting mixture was cooled to room temperature, the methanol was evaporated under reduced pressure, and 1 M hydrochloric acid (150 mL) was added to the resulting residue. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The resulting solid was reslurried and purified with diisopropyl ether to give compound 18 (4.1 g, 13.7 mmol). The yield was 91.0%.

[0203] (5) Synthesis of Compound 19 Compound 18 (3.6 g, 12.0 mmol) and N,N-dimethylaniline (1.8 g, 15.0 mmol) were dissolved in THF (35 mL). The resulting solution was cooled to 10 °C, and acrylic acid chloride (1.4 g, 15.0 mmol) was added dropwise. The mixture was stirred at 10 °C for 1 hour. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The residue was recrystallized from toluene to give compound 19 (4.0 g, 11.2 mmol). The yield was 93.0%.

[0204] (6) Synthesis of Compound A-11 Compound 19 (2.7 g, 7.5 mmol), methylhydroquinone (0.4 g, 3.0 mmol), and DMAP (0.04 g, 0.3 mmol) were dissolved in CHCl (4 mL). The resulting solution was cooled to 15 °C, and N,N-diisopropylcarbodiimide (1.1 g, 9.0 mmol) was added dropwise. The mixture was stirred at 15 °C for 3 hours. Methanol (40 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to give compound A-11 (2.2 g, 2.7 mmol). The yield was 91.5%. 1 H-NMR(CDCl3):δ=1.98(m,8H),2.33(s,3H),3.23(t,4H),4.09(t,4H),5.88(dd,2H) ),6.41(dd,2H),6.45(dd,2H),7.24(m,7H),7.58(m,4H),7.68(m,4H),8.18(m,4H)

[0205] [Production Example 12: Production of Compound A-12] Compound A-12 was synthesized according to the following scheme.

[0206] [ka]

[0207] (1) Synthesis of Compound 20 4-Amino-3-hydroxybenzoic acid (7.7 g, 50.0 mmol) and potassium ethyl xanthate (12.0 g, 75.0 mmol) were dissolved in ethanol (200 mL). The resulting solution was stirred under reflux for 3 hours. The resulting solution was cooled to room temperature, and the ethanol was evaporated under reduced pressure. 1 M hydrochloric acid and ethyl acetate were added to the resulting residue, followed by extraction with ethyl acetate. The resulting organic layer was evaporated to give compound 20 (12.2 g, 45.5 mmol). The yield was 91.0%.

[0208] (2) Synthesis of Compound 21 Compound 20 (8.0 g, 30.0 mmol), 4-chlorobutyl acetate (13.6 g, 90.0 mmol), potassium carbonate (12.4 g, 90.0 mmol), and potassium iodide (0.5 g, 3.0 mmol) were mixed with DMAc (80 mL). The resulting mixture was stirred at 80 °C for 3 hours. A solution of sodium hydroxide (6.0 g, 150.0 mmol) in 30 mL of water and 30 mL of methanol was added to the resulting mixture, and the mixture was stirred at 80 °C for 3 hours. The resulting mixture was cooled to room temperature, the methanol was evaporated under reduced pressure, and 1 M hydrochloric acid (300 mL) was added to the resulting residue. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The resulting solid was reslurried and purified with diisopropyl ether to give compound 21 (9.2 g, 28.7 mmol). The yield was 95.5%.

[0209] (3) Synthesis of Compound 22 Compound 21 (7.7 g, 24.0 mmol) and N,N-dimethylaniline (3.6 g, 30.0 mmol) were dissolved in THF (70 mL). The resulting solution was cooled to 10 °C, and acrylic acid chloride (2.7 g, 30.0 mmol) was added dropwise. The mixture was stirred at 10 °C for 1 hour. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The residue was recrystallized from toluene to give compound 22 (5.9 g, 22.2 mmol). The yield was 92.5%.

[0210] (4) Synthesis of Compound A-12 Compound 22 (3.3 g, 12.5 mmol), methylhydroquinone (0.6 g, 5.0 mmol), and DMAP (0.06 g, 0.5 mmol) were dissolved in CHCl (6 mL). The resulting solution was cooled to 15 °C, and N,N-diisopropylcarbodiimide (1.9 g, 15.0 mmol) was added dropwise. The mixture was stirred at 15 °C for 3 hours. Methanol (120 mL) was added to the resulting mixture, and the mixture was filtered. The residue was washed with methanol to obtain compound A-12 (3.6 g, 4.9 mmol). The yield was 98.0%. 1H-NMR(CDCl3):δ=1.89(m,4H),1.99(m,4H),2.43(s,3H),3.42(t,4H),4.23(t,4H),5.82(dd,2H),6.13(dd,2H) ),6.41(dd,2H),7.33(d,1H),7.41(d,1H),7.52(dd,1H),7.68(dd,1H),7.99(m,2H),8.27(d,1H),8.33(d,2H)

[0211] Comparative Preparation Example 1: Preparation of Comparative Compound RA-1 Comparative compound RA-1 was synthesized according to the following scheme.

[0212] [ka]

[0213] (1) Synthesis of Compound 23 DMAc (500 mL) was added to 4-iodophenol (22.0 g, 100.0 mmol), 3-chloro-1-propanol (14.2 g, 150.0 mmol), potassium carbonate (20.7 g, 150.0 mmol), and potassium iodide (1.7 g, 10.0 mmol). The resulting mixture was stirred at 100°C for 3 hours. The resulting mixture was cooled to room temperature, and the methanol was removed under reduced pressure. 1 M hydrochloric acid (200 mL) was added to the resulting residue. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The resulting residue was purified by flash column chromatography to give compound 23 (30.7 g, 95.5 mmol). The yield was 95.5%.

[0214] (2) Synthesis of Compound 24 Under an inert gas atmosphere, CuI (0.8 g, 4.0 mmol), triphenylphosphine (PPh3) (2.1 g, 8.0 mmol), Pd(PPh3)2Cl2 (2.8 g, 4.0 mmol), dibutylhydroxytoluene (BHT) (0.2 g, 1.0 mmol), and Et3N (1000 mL) were mixed. The resulting mixture was cooled to 0 °C, and 5-bromo-2-iodotoluene (29.7 g, 100.0 mmol) and 4-ethynylanisole (15.9 g, 120.0 mmol) were added. The mixture was stirred at room temperature for 18 hours. Water and ethyl acetate were added to the resulting mixture, which was then extracted with ethyl acetate. The organic layer was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to give compound 24 (27.3 g, 98.0 mmol). The yield was 98.0%.

[0215] (3) Synthesis of Compound 25 Under an inert gas atmosphere, CuI (0.7 g, 3.8 mmol), PPh3 (2.0 g, 7.6 mmol), Pd(PPh3)2Cl2 (2.7 g, 3.8 mmol), BHT (0.2 g, 1.0 mmol), and Et3N (950 mL) were mixed. The resulting mixture was cooled to 0 °C, and compound 24 (26.4 g, 95.5 mmol) and 2-methyl-3-butyn-2-ol (20.0 g, 237.5 mmol) were added. The mixture was heated to reflux and stirred for 3 hours. Water and ethyl acetate were added to the resulting mixture, which was then extracted with ethyl acetate. The organic layer was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to give compound 25 (26.5 g, 87.9 mmol). The yield was 92.5%.

[0216] (4) Synthesis of Compound 26 Compound 25 (15.1 g, 50.0 mmol) was dissolved in toluene (50 mL) and cooled to 0°C. Sodium hydroxide (3.0 g, 75.0 mmol) was added to the resulting solution. The resulting mixture was stirred under reflux for 3 hours. The resulting mixture was cooled to room temperature, and 1 M hydrochloric acid (100 mL) and ethyl acetate were added. The mixture was then extracted with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The residue was purified by flash column chromatography to give compound 26 (12.2 g, 49.5 mmol). The yield was 95.5%.

[0217] (5) Synthesis of Compound 27 Under an inert gas atmosphere, CuI (0.4 g, 2.0 mmol), PPh3 (1.1 g, 4.0 mmol), Pd(PPh3)2Cl2 (1.4 g, 2.0 mmol), BHT (0.2 g, 1.0 mmol), and Et3N (500 mL) were mixed. The resulting mixture was cooled to 0 °C, and compound 23 (13.6 g, 50.0 mmol) and compound 26 (14.8 g, 60 mmol) were added. The mixture was stirred at room temperature for 18 hours. Water and ethyl acetate were added to the resulting mixture, which was then extracted with ethyl acetate. The organic layer was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to give compound 27 (19.0 g, 48.0 mmol). The yield was 96.0%.

[0218] (6) Synthesis of comparative compound RA-1 Compound 27 (15.9 g, 40 mmol) and N,N-dimethylaniline (5.8 g, 48.0 mmol) were dissolved in THF (100 mL). The resulting solution was cooled to 10 °C, and acrylic acid chloride (4.3 g, 48.0 mmol) was added dropwise. The mixture was stirred at 10 °C for 1 hour. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The residue was purified by flash column chromatography to obtain comparative compound RA-1 (17.6 g, 39.0 mmol). The yield was 97.5%. 1H-NMR(CDCl3):δ=2.14(m,2H),2.49(s,3H),3.83(s,3H),4.07(t,2H),4.35(t,2H),5.82 (dd,1H),6.09(dd,1H),6.39(dd,1H),6.85(m,4H),7.28(d,1H),7.38(s,1H),7.42(m,5H)

[0219] Comparative Preparation Example 2: Preparation of Comparative Compound RA-2 Comparative compound RA-2 was prepared with reference to JP-A-2008-544954.

[0220] [ka]

[0221] Comparative Preparation Example 3: Preparation of Comparative Compound RA-3 Comparative compound RA-3 was prepared with reference to JP-A-2008-544954.

[0222] [ka]

[0223] Comparative Preparation Example 4: Preparation of Comparative Compound RA-4 Comparative compound RA-4 was prepared with reference to JP-A-2008-179654.

[0224] [ka]

[0225] Comparative Preparation Example 5: Preparation of Comparative Compound RA-5 Comparative compound RA-5 was prepared with reference to Japanese Patent No. 5962760.

[0226] [ka]

[0227] [Example 1] Using compound A-1 as Example 1, the following evaluations were carried out. (1) Phase transition temperature measurement As a measurement sample, 5 mg of compound A-1 was sealed in an aluminum sample pan and set in a differential scanning calorimeter (DSC) (Shimadzu Corporation, DSC-60). Under a nitrogen atmosphere, the sample was cooled from 25 ° C. to -10 ° C. at a rate of -25 ° C. / min and maintained at -10 ° C. for 15 minutes. Thereafter, as a first heating run, the sample was heated from -10 ° C. to 150 ° C. at a rate of 10 ° C. / min and maintained at 150 ° C. for 1 minute. As a first cooling run, the sample was cooled from 150 ° C. to -10 ° C. at a rate of -10 ° C. / min and maintained at -10 ° C. for 10 minutes. Thereafter, as a second heating run, the sample was heated from -10 ° C. to 150 ° C. at a rate of 10 ° C. / min and maintained at 150 ° C. for 1 minute. As a second cooling run, the sample was cooled from 150 ° C. to 25 ° C. at a rate of -10 ° C. / min. The endothermic onset temperature detected during the second heating, i.e., the extrapolated melting onset temperature (Tim), which is the temperature at the intersection of a straight line extending the low-temperature baseline toward the high-temperature side and a tangent drawn at the point where the slope of the curve on the low-temperature side of the melting peak is maximum, was determined as the phase transition temperature. (Evaluation criteria for phase transition temperature) A: Phase transition temperature is less than 90°C B: Phase transition temperature is 90℃ or higher and less than 110℃ C: Phase transition temperature is 110°C or higher The lower the phase transition temperature, the better the coatability.

[0228] (2) Production of compositions and optical anisotropic bodies, and measurement of Δn (refractive index anisotropy) A composition containing the compound A-1 was prepared according to the following formula, and an optically anisotropic layer was prepared using the composition, and the Δn of the compound A-1 was calculated using the composition. Since the compound A-1 was the only compound exhibiting optical anisotropy contained in the optically anisotropic layer, the Δn of the optically anisotropic layer was taken as the Δn of the compound A-1. <Composition> Compound A-1 100 parts by mass Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad907, manufactured by IGM RESINS BV) 5 parts by mass Methyl ethyl ketone 450 parts by mass

[0229] <Optical anisotropy> The composition was spin-coated onto the entire surface of a rubbed glass sheet (50 mm x 50 mm) with an alignment film. After heating the composition to a temperature at which it exhibited a nematic phase, a 244 mJ / cm 2 The film was irradiated with ultraviolet light for 100 seconds to produce an optically anisotropic layer.

[0230] <Δn (refractive index anisotropy) measurement> The in-plane retardation Re and layer thickness (nm) of the produced optically anisotropic layer were measured, and Δn was calculated by the following formula. Δn=Re / layer thickness (nm) Re was measured using a phase difference measurement device (RETS-100 manufactured by Otsuka Electronics Co., Ltd.) at a wavelength of 550 nm, and the set temperature was 25° C. The average value of the measurements at three locations was used as the measurement result. (Re measurement conditions) Retardation measurement range: Rotating analyzer method Measurement spot diameter: φ5mm Tilt angle range: 0° Measurement wavelength range: 400nm to 800nm The thickness of the optically anisotropic layer was determined by photographing a cross section of the optically anisotropic layer using a scanning transmission electron microscope (STEM) (S-4800, manufactured by Hitachi High-Technologies Corporation), measuring the thickness of the optically anisotropic layer at 10 points on the cross section image, and calculating the arithmetic mean value of the thicknesses at those 10 points. Cross-sectional photographs of the optically anisotropic layer were taken as follows. First, a 1 mm × 10 mm sample was embedded in an embedding resin to prepare a block. Hole-free, uniform slices with a thickness of 70 nm to 100 nm were cut from this block using a standard slice preparation method. An ion milling device (IM-4000II, manufactured by Hitachi High-Technologies Corporation) was used to prepare the slices. These hole-free, uniform slices were used as measurement samples. Cross-sectional photographs of the measurement samples were then taken using a scanning transmission electron microscope (STEM). STEM observations were performed using a detector set to "TE," an acceleration voltage of "30 kV," and an emission current of "10 μA." The magnification was adjusted from 5,000x to 200,000x, while adjusting the focus and observing the contrast and brightness to determine whether each layer could be distinguished. (Evaluation criteria for refractive index anisotropy) A: Δn is 0.25 or more B: Δn is less than 0.25

[0231] (3) Lightfastness evaluation An ultraviolet absorbing layer was laminated on the optically anisotropic layer prepared for measuring the refractive index anisotropy Δn, and a light resistance test was carried out.

[0232] <Laminate for light resistance test> (Preparation of UV absorbing layer) With reference to paragraph 0110 of JP 2021-189224 A, 2-[2-(6-hydroxybenzo[1,3]dioxol-5-yl)-2H-benzotriazol-5-yl]ethyl methacrylate was synthesized as an ultraviolet absorber. A coating solution for forming an ultraviolet absorbing layer was applied onto one side of a triacetyl cellulose resin film (TAC) substrate (FUJIFILM Corporation, TD80UL, thickness 80 μm), which was prepared by adding 5 parts by mass of a photopolymerization initiator (Omnirad907, manufactured by IGM Resins BV) and 5 parts by mass of the ultraviolet absorber to 100 parts by mass of pentaerythritol triacrylate (trade name: PET-30) manufactured by Nippon Kayaku Co., Ltd., to form a coating film. The formed coating film was irradiated with ultraviolet light (cumulative light amount: 150 mJ / cm ). 2), a 3 μm thick ultraviolet absorbing layer was formed. (Preparation of laminate for light resistance test) The TAC substrate side of the ultraviolet absorbing layer was attached to the optically anisotropic layer prepared for measuring refractive index anisotropy Δn using an optical adhesive (trade name: Panaclean PD-S1, 25 μm, manufactured by Panac Corporation, acrylic adhesive) with a thickness of 25 μm.

[0233] <Lightfastness test> The optically anisotropic layer of the prepared laminate for light resistance testing was irradiated with light from the ultraviolet absorbing layer side using an ultraviolet carbon arc light resistance tester (manufactured by Suga Test Instruments Co., Ltd., Fade Meter) in an air atmosphere at a chamber temperature of 42°C, a relative humidity of 50%, and an illuminance of 500 W / m 2 A light resistance test was carried out under the condition that the exposure time was 48 hours. The Re of the optically anisotropic layer was measured before and after the light resistance test in the same manner as above, and the Re change rate shown below was calculated. Re change rate (%) = [100 × {|(Re after test) - (Re before test)|} / (Re before test)] (Evaluation criteria) A: Re change rate is less than 10% B: Re change rate is 10% or more and less than 15% C: Re change rate is 15% or more The smaller the Re change rate, the better the light resistance.

[0234] [Example 2] Using compound A-2 as Example 2, the following evaluations were carried out. (1) Phase transition temperature measurement The phase transition temperature was measured in the same manner as in Example 1, except that compound A-2 was used instead of compound A-1.

[0235] (2) Production of compositions and optical anisotropic bodies, and measurement of Δn (refractive index anisotropy) Since compound A-2 did not align on its own, a composition containing another liquid crystal compound was prepared according to the following formulation, and an optically anisotropic layer was prepared using the composition, and Δn was determined in the same manner as in Example 1. Specifically, the refractive index anisotropy Δn was measured for optically anisotropic layers produced in the same manner as in Example 1 using the following compositions 2-a, 2-b, and 2-c, each containing 20 parts by mass, 10 parts by mass, and 0 parts by mass of compound A-2. A linear regression analysis was performed on the obtained measurements to determine the refractive index anisotropy Δn when the amount of compound A-2 was 100 parts by mass. When refractive index anisotropy Δn is y and the parts by mass of compound A-2 is x, regression coefficients a and b of the following regression equation were derived from measured values ​​using the least squares method. y=ax+b The derived regression equation was substituted with x=100, and the obtained value was taken as the extrapolated value of the refractive index anisotropy Δn of compound A-2. <Composition 2-a> Compound A-2 20 parts by mass Polymerizable liquid crystal compound (B-1) (manufactured by TCI, CAS RN: 132900-75-5, product code: D5936) 80 parts by mass Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad907, manufactured by IGM RESINS BV) 5 parts by mass Methyl ethyl ketone 450 parts by mass <Composition 2-b> Compound A-2 10 parts by mass Polymerizable liquid crystal compound (B-1) (manufactured by TCI, CAS RN: 132900-75-5, product code: D5936) 90 parts by weight Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad907, manufactured by IGM RESINS BV) 5 parts by mass Methyl ethyl ketone 450 parts by mass <Composition 2-c> Polymerizable liquid crystal compound (B-1) (manufactured by TCI, CAS RN: 132900-75-5, product code: D5936) 100 parts by mass Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad907, manufactured by IGM RESINS BV) 5 parts by mass Methyl ethyl ketone 450 parts by mass

[0236] (3) Lightfastness evaluation In the light resistance evaluation of Example 1, the light resistance evaluation was performed in the same manner as in Example 1, except that the optically anisotropic layer was changed to an optically anisotropic layer produced using the composition 2-a containing 20 parts by mass of compound A-2.

[0237] [Examples 3, 4, 6 to 10, Comparative Examples 2, 4, and 5] In Examples 3, 4, 6 to 10 and Comparative Examples 2, 4, and 5, the phase transition temperature measurement, the production of the composition and the optically anisotropic layer, the measurement of Δn, and the light resistance test were carried out in the same manner as in Example 1, except that the compounds shown in Table 3 were used instead of compound A-1 used in Example 1.

[0238] [Examples 5, 11, 12, Comparative Examples 1 and 3] In Examples 5, 11, and 12 and Comparative Examples 1 and 3, the phase transition temperature measurement, the production of the composition and the optically anisotropic layer, the Δn measurement, and the light resistance test were carried out in the same manner as in Example 2, except that the compounds shown in Table 3 were used instead of Compound A-2 in Example 2.

[0239] [Table 3]

[0240] As shown in Examples 1 to 12, the compounds represented by general formula (I) of the present disclosure were shown to be compounds with improved refractive index anisotropy Δn and light resistance in an air atmosphere, and reduced phase transition temperatures. In contrast, the compound of Comparative Example 1, which is a tolan compound, had poor light resistance in an air atmosphere. The compound of Comparative Example 2, which corresponds to the compound having a 2,6-naphthyl group specifically described in Patent Document 1, had a high phase transition temperature, an insufficient refractive index anisotropy Δn, and poor light resistance. Among the compounds having a 2,6-naphthyl group specifically described in Patent Document 1, the compound of Comparative Example 3, which corresponds to a compound having a specifically high refractive index anisotropy Δn, had a high phase transition temperature and poor light resistance. Compared to the compound of Comparative Example 3, the compound of Example 9, which has a structure in which the linking group -OCOO- adjacent to the naphthyl group is changed to -S-, shows a lower phase transition temperature. Furthermore, the compound of Comparative Example 4, which has a 2,6-naphthyl group and in which the linking group adjacent to the naphthyl group is -O-, had a high phase transition temperature, insufficient refractive index anisotropy Δn, and poor light resistance.

[0241] Example 13: Production of optical elements A composition containing the compound A-1 of Example 1 was prepared according to the following formulation, and an optical element including an optically anisotropic layer in which a cholesteric liquid crystal phase was fixed was produced using the composition. <Composition> Compound A-1 24.5 parts by mass Chiral agent (compound (Ch-1) below) 0.5 parts by mass Photopolymerization initiator (Omnirad907, manufactured by IGM RESINS BV) 1 part by mass Leveling agent (acrylic surfactant, Polyflow No. 75, manufactured by Kyoeisha Chemical Co., Ltd.) 0.01 parts by mass Methyl ethyl ketone (MEK) 24 parts by mass Methyl isobutyl ketone (MIBK) 50 parts by mass

[0242] The chiral agent (compound (Ch-1) below) was synthesized by a combination of the methods described in JP 2005-263778 A, U.S. Pat. No. 5,886,242, and British Patent Application Publication No. 2,298,202. The R-configuration of the binaphthalene moiety in compound (Ch-1) was used.

[0243] [ka]

[0244] <Formation of photo-alignment film> A composition for a photo-alignment film was prepared in the same manner as the photo-alignment film material in Example 1 of JP 2021-103225 A. The composition for a photoalignment film was applied by spin coating to one side of a PET substrate (Toyobo Co., Ltd., E5100, thickness 38 μm) so that the film thickness after curing would be 0.2 μm, and the composition was dried and thermally cured by heating in an oven at 90°C for 2 minutes to form a cured coating film. Thereafter, the surface of this cured coating film was exposed to polarized ultraviolet light containing a 313 nm emission line using an Hg-Xe lamp and a Glan-Taylor prism in a direction perpendicular to the substrate normal at an exposure dose of 100 mJ / cm. 2 An alignment film was formed by irradiating the liquid crystal with light.

[0245] <Fabrication of optical elements> The composition was applied onto the alignment film so that the film thickness after curing would be about 4 μm, forming a polymerizable liquid crystal composition film. The film was then dried in an oven at 90°C for 2 minutes, and then irradiated with ultraviolet (UV) light at a dose of 400 mJ / cm using an H bulb manufactured by Fusion under a nitrogen atmosphere. 2 An optically anisotropic layer was formed by irradiation with light of 1000 .mu.m. to prepare an optical element. A cross section of the optically anisotropic layer of the optical element was observed using a scanning transmission electron microscope (STEM), and the observation of a repeating structure of light and dark areas confirmed that the layer was composed of a fixed cholesteric liquid crystal layer. Specifically, the central portion of the optical element sample was cut into strips (2 mm x 5 mm), embedded in a thermosetting resin, and then cut with a microtome to produce smooth cross-sections to produce ultrathin sections (80 nm thick). The obtained ultrathin cross-sections were observed using STEM under the following measurement conditions (detector TE, acceleration voltage 30 kV, emission current 10 μA, magnification 5000x) to obtain cross-sectional images of the optically anisotropic layer of the optical element. In the cross-sectional images obtained using STEM, a repeating structure of dark area-light area-dark area-light area, or light area-dark area-light area-dark area was confirmed.

[0246] Example II Series: Second Present Disclosure In Example II series, Compound A-1, Compound A-4, Compound A-5, Compound A-7, Compound RA-1, Compound RA-2, Compound RA-4, and Compound RA-5 were each prepared in the same manner as in Example I series. [Example II-1] In Example II-1, an optically anisotropic medium was produced using Compound A-1 as a polymerizable liquid crystal compound containing a partial structure represented by formula (Ia). <Composition> Compound A-1 100 parts by mass Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad907, manufactured by IGM RESINS BV) 5 parts by mass Leveling agent (acrylic surfactant, Polyflow No. 75, manufactured by Kyoeisha Chemical Co., Ltd.) 0.01 parts by mass Methyl ethyl ketone 450 parts by mass

[0247] <Optical anisotropy> The composition was applied by bar coating to a 100 μm thick PET film (A4160: manufactured by Toyobo Co., Ltd.) that had been rubbed with nylon, so that the cured film thickness was 5 μm. After heating to a temperature at which the composition exhibited a nematic phase and drying, the composition was exposed to a high-pressure mercury lamp at 240 mJ / cm. 2 The film was irradiated with ultraviolet light of 1000 kJ / cm to produce an optically anisotropic layer.

[0248] (1) Bending resistance test The test specimen used for the flex resistance test was cut into a 50 mm x 20 mm square from near the center of the optically anisotropic medium. The test specimen was bent in the long direction using a cylindrical mandrel method in accordance with JIS-K5600-5-1:1999, with the optically anisotropic layer facing outward. The presence or absence of cracks was observed under a 10x magnifying glass at the bent portion of the optically anisotropic layer when the mandrel had a diameter of 3 mm. The fewer cracks, the better the flex resistance and the superior the lamination and processability. (Evaluation criteria for bending resistance) A: No cracks B: Cracks present

[0249] (2) Δn (refractive index anisotropy) measurement The composition was spin-coated onto the entire surface of a rubbed glass sheet (50 mm x 50 mm) with an alignment film. After heating the composition to a temperature at which it exhibited a nematic phase, a 244 mJ / cm 2 The film was irradiated with ultraviolet light for 100 seconds to produce an optically anisotropic layer. For the produced optically anisotropic layer, Δn was calculated in the same manner as in "Δn (refractive index anisotropy) measurement" described in Example 1 of the Example I series. (Evaluation criteria for refractive index anisotropy) A: Δn is 0.25 or more B: Δn is less than 0.25

[0250] (3) FT-IR measurement The infrared absorption spectrum of the optically anisotropic medium for which the Δn measurement was carried out was measured from the optically anisotropic layer side by the ATR method using a Fourier transform infrared spectrophotometer. The following predetermined peaks P1, P2, and P3 were detected in the peak detection mode of the analysis software. Using the analysis software, the height from the background to the peak top of each peak was determined as the peak intensity. P1;1205cm -1 ~1225cm -1 Peak intensity of SC bond located at P2; 1600cm -1 ~1650cm -1 Peak intensity of C=C bond located at P3; 1700cm -1 ~1750cm -1 Peak intensity of C=O bond located at FT-IR measurements were performed at three different locations on the sample. The average value of P1 measured at the three locations was taken as P1 for that sample. Similarly, the average values ​​of P2 and P3 measured at the three locations were taken as P2 and P3 for that sample. P1 / P2, P1 / P3, and P1 / (P2+P3) were calculated from the obtained P1, P2, and P3 values. (Measurement conditions) Measurement equipment: Fourier transform infrared spectrophotometer (JASCO Corporation, FT-IR6100 equipped with ATR-PRO470-H) Light source: High-brightness ceramic light source Detector: DLATGS Beam splitter: Ge / KBr Measurement mode: ATR method (diamond prism, incident angle 45°) Measurement wavenumber range: 4,000 cm -1 ~400cm -1 Resolution: 4cm -1 Measurement spot diameter: φ1.5mm Accumulation count: 32 times Analysis: Spectra Manager Version 2 Spectral Analysis Program

[0251] [Examples II-2 to II-4, Comparative Examples II-1 to II-4] In Examples II-2 to II-4 and Comparative Examples II-1 to II-4, compositions and optical anisotropic bodies were produced in the same manner as in Example II-1, except that instead of using Compound A-1 as the polymerizable liquid crystal compound containing the partial structure represented by formula (Ia) in Example II-1, compounds shown in Table 4 were used. Furthermore, a bending resistance test and Δn (refractive index anisotropy) measurement were carried out using the obtained optical anisotropic body in the same manner as in Example II-1. For Comparative Example II-1, FT-IR measurement was carried out using the obtained optical anisotropic body in the same manner as in Example II-1.

[0252] [Example II-5] A composition having the following composition was prepared using Compound A-1 as the polymerizable liquid crystal compound containing a partial structure represented by Formula (Ia) and further containing other polymerizable liquid crystal compounds shown in Table 4, and an optical anisotropic body was produced using the composition. Furthermore, a bending resistance test, Δn (refractive index anisotropy) measurement, and FT-IR measurement were performed using the obtained optical anisotropic body in the same manner as in Example II-1.

[0253] <Composition> Compound A-1 10 parts by mass Compound RA-2 90 parts by mass Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad907, manufactured by IGM RESINS BV) 5 parts by mass Leveling agent (acrylic surfactant, Polyflow No. 75, manufactured by Kyoeisha Chemical Co., Ltd.) 0.01 parts by mass Methyl ethyl ketone 450 parts by mass

[0254] [Example II-6] In Example II-6, except that compound A-4 was used instead of compound A-1 in Example II-5, a composition was prepared in the same manner as in Example II-5, and an optical anisotropic body was produced using this composition.Furthermore, in the same manner as in Example II-1, bending resistance test, Δn (refractive index anisotropy) measurement, and FT-IR measurement were carried out using the obtained optical anisotropic body.

[0255] [Example II-7] In Example II-7, except that compound RA-1 was used instead of compound RA-2 in Example II-5, a composition was prepared in the same manner as in Example II-5, and an optical anisotropic body was produced using this composition.Furthermore, in the same manner as in Example II-1, a bending resistance test and Δn (refractive index anisotropy) measurement were carried out using the obtained optical anisotropic body.

[0256] [Example II-8] In Example II-8, except that compound RA-5 was used instead of compound RA-2 in Example II-5, a composition was prepared in the same manner as in Example II-5, and an optical anisotropic body was produced using this composition.Furthermore, in the same manner as in Example II-1, a bending resistance test and Δn (refractive index anisotropy) measurement were carried out using the obtained optical anisotropic body.

[0257] [Table 4] In the table, "n / a" indicates that the measurement was not performed.

[0258] As shown in Examples II-1 to II-8, an optically anisotropic layer, which is a cured product of a polymerizable liquid crystal composition containing a partial structure represented by formula (Ia) of the present disclosure, was shown to have both improved refractive index anisotropy Δn and improved flex resistance. In contrast, the optically anisotropic layer of Comparative Example II-1 containing a tolan compound, the optically anisotropic layers of Comparative Examples II-2 and II-3 containing conventional compounds having a 2,6-naphthyl group, and the optically anisotropic layer of Comparative Example II-4 all formed hard and brittle films and had poor bending resistance.

Claims

1. A liquid crystal compound represented by the following general formula (I): 【Chemistry 1】 [In general formula (I), Z １ and Z ２ each independently represents a hydrogen atom, —CN, —NCS, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or a polymerizable group, and at least one of Z 1 and Z 2 represents a polymerizable group. The polymerizable group represents a group selected from the following formulas (Z-1) to (Z-12): R ｓｐ１ and R ｓｐ２ each independently represents one —CH ２ - or two or more non-adjacent -CH ２ Each "-" independently represents an alkylene group having 1 to 20 carbon atoms which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, or -NH-CO-, or a single bond. S represents a sulfur atom. L ２ , and L ３ are each independently —O—, —S—, —CHR—, —CHRCHR—, —OCHR—, —CHRO—, —SO—, or —SO ２ -, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO ２ -CHR-, -CHR-SO ２ -, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO ２ -CHRCHR-SO ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CHRCHR-, -OCO-CHRCHR-, -CHRCHR-COO-, -CHRCHR-OCO-, -COO-CHR-, -OCO-CHR-, -CHR-COO-, -CHR-OCO-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=N-N=CR-, -CF=CF-, or a single bond; R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and when a plurality of R's are present, they may be the same or different. A represents a group represented by any one of the following formulae (A-1) to (A-4), and may be substituted with one or more substituents E. T ２ each independently represents a group represented by the following formula (B-1), (B-2), (B-2-2), (B-3) or (B-4), which may be substituted by one or more substituents E: Substituent E each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, or a polymerizable group, provided that the above groups described as substituent E are not —CH ２ When the group has -, -CH contained in the above group ２ Groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH- are also included in the substituent E. Furthermore, when the above groups described as the substituent E have a hydrogen atom, groups in which at least one of the hydrogen atoms contained in the above groups is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group are also included in the substituent E. Each n independently represents an integer of 1 to 3. L ２ , and T ２ When there are a plurality of each of these, they may be the same or different. 【Chemistry 2】 (In formulas (Z-1) to (Z-12), each R z is independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, or a trifluoromethyl group. * indicates the bonding position with R sp1 or R sp2 .) 【Transformation 3】 (In formulas (A-1) to (A-4), W １ ~W １６ are each independently, CR １ or N, R １ represents a hydrogen atom or the substituent E. Y １ ~Y ２ are each independently NR ２ , O or S, R ２ represents a hydrogen atom or the substituent E. * indicates the bonding position with -COO- or S.) 【Chemistry 4】 (In formulas (B-1), (B-2), (B-2-2), (B-3), and (B-4), W 21 to W 32 each independently represent CR 1 or N, and R 1 represents a hydrogen atom or the substituent E described above. Y 11 and Y 12 each independently represent NR 2 , O or S, and R 2 represents a hydrogen atom or the substituent E described above. In formula (B-2-2), a plurality of W 27 to W 30 may be the same or different. Adjacent substituents E may be bonded to each other to form a ring. * represents the bonding position to L 2 , L 3 or O.)

2. The liquid crystal compound described in claim 1, wherein the substituent E represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyl group having 2 to 6 carbon atoms, an alkanoyloxy group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, a trifluoromethyl group, a fluorine atom, or a chlorine atom.

3. A liquid crystal compound described in claim 1, which satisfies at least one of the following requirements (i) or (ii): Requirement (i): Z 1 and Z 2 each independently represent -CN, -NCS, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or the polymerizable group, and each independently represent an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkanoyl group having 2 to 6 carbon atoms, an alkanoyloxy group having 2 to 6 carbon atoms, an alkyloxycarbonyl group having 2 to 6 carbon atoms, or a trifluoromethyl group. Requirement (ii): Z 1 and Z 2 each independently represent the polymerizable group.

4. L 2 and L 3 each independently represent -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO 2 -, -COO-, -OCO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO 2 -CHR-, -CHR-SO 2 -, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO 2 -CHRCHR-SO 2 2. The liquid crystal compound according to claim 1, wherein R represents -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CHRCHR-, -OCO-CHRCHR-, -CHRCHR-COO-, -CHRCHR-OCO-, -COO-CHR-, -OCO-CHR-, -CHR-COO-, -CHR-OCO-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=N-N=CR-, -CF=CF-, or a single bond; R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms; and when a plurality of Rs are present, they may be the same or different.

5. The liquid crystal compound according to claim 1, wherein, in the general formula (I), A represents a group represented by the formula (A-1), and the group represented by the formula (A-1) may be substituted with one or more substituents E.

6. The liquid crystal compound according to claim 1, which is represented by the following general formula (I-1): 【Transformation 5】 (In general formula (I-1), Z １ , Z ２ , R ｓｐ１ , R ｓｐ２ , S., L. ２ , L ３ , T ２ and E each independently represent the same as defined in the general formula (I). In the general formula (I-1), the 2,6-naphthyl group may be substituted with one or more substituents E, k1 represents an integer of 0 to 6, and n' represents an integer of 0 to 2. L ２ and T ２ When there are a plurality of each, they may be the same or different.)

7. The liquid crystal compound according to claim 1, which is represented by the following general formula (I-2): 【Transformation 6】 (In general formula (I-2), Z １ , Z ２ , R ｓｐ１ , R ｓｐ２ , S., L. ２ , L ３ , T ２ and E each independently represent the same as defined in the general formula (I). In the general formula (I-2), the 2,6-naphthyl group and the phenyl group may be substituted with one or more substituents E, k1 represents an integer of 0 to 6, and k2 represents an integer of 0 to 4. n' represents an integer of 0 to 2. ２ and T ２ When there are a plurality of each, they may be the same or different.)

8. A liquid crystal composition comprising the liquid crystal compound according to any one of claims 1 to 7.

9. The liquid crystal composition according to claim 8 , further comprising a polymerization initiator.

10. The liquid crystal composition according to claim 8 , further comprising a chiral agent.

11. 9. An optically anisotropic medium in which the compound represented by formula (I) in the liquid crystal composition according to claim 8 is aligned.

12. An optically anisotropic body which is a cured product of the liquid crystal composition according to claim 9 .

13. An optically anisotropic medium in which the compound represented by the general formula (I) in the liquid crystal composition according to claim 10 is aligned.

14. An optical element having an optically anisotropic layer formed using the liquid crystal composition according to claim 8.

15. an optically anisotropic layer formed using the liquid crystal composition according to claim 8; the optically anisotropic layer has an alignment pattern, The optical element, wherein the alignment pattern is an alignment pattern in which the direction of the optical axis derived from the liquid crystal compound contained in the liquid crystal composition is continuously rotated and changed along at least one direction in the plane.

16. An optically anisotropic body which is a cured product of a polymerizable liquid crystal composition containing a partial structure of the following general formula (Ia): 【Transformation 7】 (In general formula (Ia), the 2,6-naphthyl group may be substituted with one or more substituents E, and k1 represents an integer of 0 to 6. Substituent E each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, or a polymerizable group, provided that the above groups described as substituent E are not —CH ２ When the group has -, -CH contained in the above group ２ Groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH- are also included in the substituent E. Furthermore, when the above groups described as the substituent E have a hydrogen atom, groups in which at least one of the hydrogen atoms contained in the above groups is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group are also included in the substituent E. ** indicates the bonding position with other atoms.)

17. 17. The optically anisotropic body according to claim 16, which is a cured product of a polymerizable liquid crystal composition containing 4% by mass or more of a compound having the partial structure of general formula (Ia).

18. 1205 cm measured by Fourier transform infrared spectrophotometer (FT-IR) using the ATR method －１ ~1225cm －１ The peak intensity of the S-C bond (P1) located at 1600 cm －１ ~1650cm －１ 18. The optical anisotropic body according to claim 16, wherein the ratio (P1 / P2) of the peak intensity of the C=C bond located at the position (A) to the peak intensity (P2) of the C=C bond located at the position (B) is 0.30 or more and 1.80 or less.

19. An optical element comprising the optically anisotropic body according to claim 16 or 17 as an optically anisotropic layer.

20. The optically anisotropic layer comprises the optically anisotropic body according to claim 16 or 17, the optically anisotropic layer has an alignment pattern, The optical element has an alignment pattern in which the direction of an optical axis derived from a compound having liquid crystal properties contained in the composition is continuously rotated along at least one direction in a plane.

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