Compound, composition, optically anisotropic body, and optical element

Abstract

This compound is represented by formula (I). Z1-Rsp1-S-(T1-L1)m-A-(L2-T2)n-L3-Rsp2-Z2 (Each symbol in general formula (I) is as described in the specification.)

Description

Compound, composition, optically anisotropic body, and optical element

[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.

[0002] Compounds having liquid crystallinity (hereinafter also referred to as "liquid crystal compounds") and compositions having liquid crystallinity (hereinafter also referred to as "liquid crystal compositions") 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 suitable for the production of a liquid crystal composition, and as a compound having a phase width large enough 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 a variety of applications. Furthermore, even if a compound having a high refractive index anisotropy Δn does not itself have liquid crystallinity, it can be mixed with another compound having liquid crystallinity to form a liquid crystal composition having a high refractive index anisotropy Δn, which is useful for a variety of applications.

[0003] JP 2008-544954 A JP 2023-3351 A

[0004] However, the compounds having a 2,6-naphthyl group specifically described in Patent Document 1 have problems such as insufficient refractive index anisotropy Δn (hereinafter also simply referred to as "Δn") and a high phase transition temperature. The tolan compounds described in Patent Document 2 have problems of deterioration and coloration 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 lightfastness test conducted under oxygen-blocked conditions showed good lightfastness, but in practical use, lightfastness 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 lamination process with other optically anisotropic layers, the substrate peeling process after transfer to other optically anisotropic layers, and during processing. Thus, there is a trade-off between high refractive index anisotropy and flexibility. Cured films of liquid crystal compositions containing a compound having a 2,6-naphthyl group, as specifically described in Patent Document 1, and cured films of liquid crystal compositions containing a tolane compound, as described in Patent Document 2, tend to be 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.

[0008] The present inventors have conducted extensive research and found that the above-mentioned 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] (In general formula (I), Z １ and Z ２ R 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. ｓｐ１ and R ｓｐ２ each independently represents one —CH ２ - or two or more non-adjacent -CH ２Each "-" independently represents an alkylene group having 1 to 20 carbon atoms which may 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 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 there are multiple R's, they may be the same or different. １ , and T ２each 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 of the following formulas (A-1) to (A-4), which 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, provided that the above groups described as substituent E are not —CH ２ When the group has -, -CH contained in the above group ２ Substituent E also includes groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above groups described as substituent E have a hydrogen atom, substituent E also includes 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. 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] (In formulas (A-1) to (A-4), W １ ~W １６ are each independently, CR １ or N, R １represents a hydrogen atom or the substituent E. １ ~Y ２ are each independently NR ２ , O or S, R ２ represents a hydrogen atom or the substituent E. * represents L １ , L ２ , L ３ , or represents 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) is optionally 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] (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 [1] to [3], which is represented by the following general formula (I-2):

[0014] (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, k2 represents an integer of 0 to 4, 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.

[0015] [5] The compound according to any one of [1] to [4] above, which has liquid crystallinity. [6] A composition comprising the compound according to any one of [1] to [5] above. [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 body in which the compound represented by general formula (I) in the composition according to any one of [6] to [8] above is aligned.

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

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

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

[0016] In order to achieve the second object, the second present disclosure includes the following aspect:

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

[0017] (In general formula (Ia), the 2,6-naphthyl group may be substituted by one or more substituents E, and k1 represents an integer of 0 to 6. Each substituent E 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 the substituents E are not —CH ２ When the group has -, -CH contained in the above group ２ Substituent E also includes groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above groups described as substituent E have a hydrogen atom, substituent E also includes 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. ** represents the bonding position to another atom.

[0018]

[15] The optically anisotropic body according to the above

[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 above general formula (Ia).

[16] ATR method Fourier transform infrared spectrophotometer (FT-IR) measured 1205 cm －１ ~1225cm －１ The peak intensity of the S-C bond (P1) located at 1600 cm －１ ~1650cm －１The optical anisotropic body according to any one of

[14] to

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

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

[14] to

[16] as an optically anisotropic layer.

[18] An optical element having the optical anisotropic body according to any one of

[14] to

[16] as an optically anisotropic layer, wherein the optical anisotropic layer has an alignment pattern, and the alignment pattern is an alignment pattern in which the direction of the optical axis derived from the compound having liquid crystallinity contained in the composition is continuously rotated along at least one direction in the plane.

[0019] According to a 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 a second embodiment of the present disclosure, it is possible to provide an optically anisotropic body and an optical element having improved refractive index anisotropy Δn and suppressed crack generation.

[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 following exemplary embodiments and examples. Furthermore, for clarity of explanation, the drawings may schematically depict the width, thickness, shape, etc. of each part compared to the actual form. However, 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 previously described with reference to the previous drawings may be denoted by the same reference numerals, and detailed descriptions may be omitted as appropriate. For convenience of explanation, the terms "above" and "below" 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 member or region, is described as being "above (or below)" another component, such as another member or region, unless otherwise specified, this includes not only the case where the component is directly above (or below) the other component, but also the case where the component is above (or below) the other component, i.e., the case where another component is present above (or below) the other component.

[0021] In the present disclosure, the alignment restraining 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. In addition, in this specification, the terms "plate," "sheet," and "film" are not distinguished from each other solely based on the difference 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 viewed overall and from a global perspective. In addition, in the present disclosure, the term "to" indicating a numerical range is used to mean that the numerical values ​​written before and after it are included as the lower and upper limits.

[0022] In this 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 perpendicular to the X-axis along the plane of the layer 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 using the following formula: In-plane retardation (Re) = (Nx - Ny) x d. In this specification, unless otherwise specified, measurement of the in-plane retardation and other measurements and evaluations are performed in an atmosphere with a temperature of 23°C ± 5°C and a humidity of 40% to 65%. Furthermore, before measurement and evaluation, the sample is exposed to this atmosphere for 30 minutes or more.

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

[0024] (In general formula (I), Z １ and Z ２ R 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. ｓｐ１ and R ｓｐ２ each independently represents one —CH ２ - or two or more non-adjacent -CH ２Each "-" independently represents an alkylene group having 1 to 20 carbon atoms which may 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 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 there are multiple R's, they may be the same or different. １ , and T ２each 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 of the following formulas (A-1) to (A-4), which 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, provided that the above groups described as substituent E are not —CH ２ When - is contained in the above group, -CH ２ Substituent E also includes groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above groups described as substituent E have a hydrogen atom, substituent E also includes 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. 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] (In formulas (A-1) to (A-4), W １ ~W １６ are each independently, CR １ or N, R １represents a hydrogen atom or the substituent E. １ ~Y ２ are each independently NR ２ , O or S, R ２ represents a hydrogen atom or the substituent E. * represents L １ , L ２ , L ３ , or represents the bonding position with S.)

[0026] The compound represented by general formula (I) of the present disclosure contains a group represented by any one of formulas (A-1) to (A-4) as a partial structure and contains -S- (sulfur atom) as a bonding moiety, thereby improving refractive index anisotropy Δn and lightfastness in an air atmosphere and lowering the phase transition temperature. The group represented by any one of 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 in the molecular structure, thereby improving refractive index anisotropy Δn, and it is presumed that the polarizability of the sulfur atom and the synergistic effect of S-S interactions improve refractive index anisotropy Δn. 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 interactions also improves refractive index anisotropy Δn. The group represented by any one of formulas (A-1) to (A-4) contained as a partial structure is a rigid moiety, which causes the 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. As a result, improved solubility and a lower phase transition temperature are achieved, thereby improving coatability. Furthermore, because the compound represented by general formula (I) of the present disclosure does not contain a triple bond, the coloring observed in tolan compounds such as those described in Patent Document 2 and degradation due to light in oxygen are suppressed. Therefore, the compound represented by general formula (I) of the present disclosure has improved light resistance in an air atmosphere.

[0027] The cholesteric liquid crystal phase formed using a compound having such a high refractive index anisotropy Δn has the advantage of widening the reflection band and improving the reflection efficiency. Furthermore, 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, a thin optical element with excellent light resistance can be produced. Furthermore, since the compound of the present disclosure has a reduced phase transition temperature, there is the advantage 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. 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 a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group, a t-butoxy group, and an n-pentoxy group. Examples of the alkoxy group having 1 to 10 carbon atoms include an alkoxy group having 1 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. Examples of the alkylthio group having 1 to 10 carbon atoms include linear or branched alkylthio groups, such as a methylthio group, an ethylthio group, an n-propylthio group, an i-propylthio group, an n-butylthio group, a t-butylthio group, and an n-pentylthio group. The alkylthio group having 1 to 10 carbon atoms may be an alkylthio group having 1 to 5 carbon atoms, or may be 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 In terms of superior reactivity, it is preferable that at least one of Z １ and Z ２ In terms of availability of raw materials and ease of synthesis, it is preferable that both Z １ and Z２ One 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, groups used in conventional polymerizable compounds can be used without any restrictions. Preferably, the polymerizable groups 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] (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 ultraviolet polymerization is used 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), and 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 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-, -NH-CO-, or -CH=CH-, or a single bond.

[0034] R ｓｐ１ and R ｓｐ２ are each independently one -CH ２ - or two or more non-adjacent -CH ２It is more preferable that each - independently represents an alkylene group having 1 to 12 carbon atoms which may be replaced by O-, -COO-, or -OCO-, or a single bond, it is even more preferable that each - independently represents an alkylene group having 1 to 12 carbon atoms or a single bond, it is even more preferable that each - independently represents an alkylene group having 1 to 10 carbon atoms or a single bond, and it is particularly preferable that each - independently represents an alkylene group having 1 to 6 carbon atoms or a single bond, and when there are multiple -, 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, ｓｐ１ and R ｓｐ２ are preferably each independently a single bond. １ and Z ２ each independently represents a polymerizable group, ｓｐ１ and R ｓｐ２ are preferably each independently the alkylene group.

[0035] L １ , 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 Rs are present, they may be the same or different. １ and L ２ When there are a plurality of R's, 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 ２ More specifically, from the viewpoints of liquid crystallinity, availability of raw materials, and ease of synthesis, —COO—, —OCO—, —OCH ２ -, -CH ２ O-, -CF ２ O-, -OCF ２ -, -CH ２ CH ２ -, -CF ２ CF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ --, --OCO-CH ２ CH ２ -, -CH ２ CH ２ -COO-, -CH ２ CH ２ It preferably represents —OCO—, —CH═CH—, —CF═CF—, or a single bond, and ２ -, -CH ２ O-, -CF ２ O-, -OCF ２ -, -CH ２CH ２ --, --COO-CH ２ CH ２ --, --OCO-CH ２ CH ２ -, -CH ２ CH ２ -COO-, -CH ２ CH ２ It is more preferable that it represents —OCO—, —CH═CH—, or a single bond, and is preferably —COO—, —OCO—, or —COO—CH ２ CH ２ --, --OCO-CH ２ CH ２ -, -CH ２ CH ２ -COO-, -CH ２ CH ２ More preferably, it represents —OCO—, —CH═CH—, or a single bond, and more preferably represents —COO—, —OCO—, or —COO—CH ２ CH ２ --, --OCO-CH ２ CH ２ -, -CH ２ CH ２ -COO-, -CH ２ CH ２ It is even more preferable that it represents —OCO— or a single bond, and it is particularly preferable that it represents —COO— or —OCO—.

[0037] L ３ In terms of availability of raw materials and ease of synthesis, -O-, -S-, -OCH ２ -, -CH ２ It preferably represents O-, -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. ３ From the viewpoint of improving Δn, it is particularly preferable that R represents —S—. ｓｐ２ When represents a single bond, L ３ may be a single bond.

[0038] T １ , and T ２each independently 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, 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 together. Note that, T １ and T ２ When each of them independently appears plurally, they may be the same or different. When each of them independently appears plurally, 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 a cyclohexanediyl group; cycloheptanediyl groups such as a cycloheptane-1,2-diyl group, a cycloheptane-1,3-diyl group, and a cycloheptane-1,4-diyl group; cyclooctanediyl groups such as a cyclooctane-1,2-diyl group, a cyclooctane-1,3-diyl group, a cyclooctane-1,4-diyl group, and a cyclooctane-1,5-diyl group; and 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 decalindiyl groups such as decahydronaphthalene-2,5-diyl, decahydronaphthalene-2,6-diyl, and decahydronaphthalene-2,7-diyl; adamantanediyl groups such as adamantane-1,2-diyl and adamantane-1,3-diyl; 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; and the like. 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 which 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, provided that the above groups described as substituent E are not —CH ２ When - is contained in the above group, -CH ２Substituent E also includes a group in which at least one of - is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above group described as substituent E has a hydrogen atom, 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. The polymerizable group here is the same as Z １ and Z ２ The number of carbon atoms in the substituent E may be the same as that of the polymerizable group described above. Note that the number of carbon atoms in the substituent E also includes the number of carbon atoms in the carbonyl (C═O) in the alkanoyl group or alkyloxycarbonyl group, for example.

[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] (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. １１ ~Y １８ are each independently NR ２ , O or S, R ２ represents a hydrogen atom or the substituent E. 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. * represents L １ , L ２ , L ３ , or represents 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] (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] Examples of the groups represented by the 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). １ R in １ , and CR ３ R ４ R in ３ and R ４ are represented by hydrogen atoms, but each hydrogen atom may be replaced by the substituent E described above.

[0050]

[0051]

[0052]

[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 Y, they may be the same or different. １１ ~Y １８ are each independently NR ２ , O or S, and may represent O or S. ２ When there are a plurality of V, they may be the same or different. １ ~V ４ are each independently, CR ３ R ４ , N.R. ５ , O or S, CR ３ R ４In general formula (B-10), R 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 selected from the viewpoint of visible light transmittance. ２２ and W ２３ and preferably do not both represent N, and W ２５ and W ２６ and preferably do not both represent N, and W ２１ represents N, and W ２２ ~W ２６ is CR １ or W ２１ ~W ２６ All of this is CR １ and W ２１ ~W ２６ All of this is 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 and preferably do not both represent N, and W ２９ and W ３０ and preferably do not both represent N, and W ２７ represents N, and W ２８ ~W ３０ is CR １ or W ２７ ~W ３０ All of this is CR １ and W ２７ ~W ３０ All of this is 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 ３２Preferably, 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 viewpoints 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 and Y in the general formula (B-8) preferably 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 preferably ４１ and W ４２ and W ４３ and preferably do not both represent N, and W ４４ and W ４５ and W ４６ and preferably do not both represent N, and W ４６ represents N, and W ４１ ~W ４５ is CR １ or W４１ ~W ４６ All of this is CR １ and W ４１ ~W ４６ All of this is 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 V １ ~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 defined 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 the substituent E is contained in each formula, there are advantages such as improved solvent solubility and 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 represent a group represented by the above general formula (B-1), (B-2), (B-2-2), (B-3) or (B-4), more preferably represent 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] (In formulas (A-1) to (A-4), W １ ~W １６ are each independently, CR １ or N, R１ represents a hydrogen atom or the substituent E. １ ~Y ２ are each independently NR ２ , O or S, R ２ represents a hydrogen atom or the substituent E. * represents L １ , L ２ , L ３ , or represents 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 selected from the viewpoint of visible light transmittance. ２ and W ３ and preferably do not both represent N, and W ５ and W ６ and preferably do not both represent N, and W １ represents N, and W ２ ~W ６ is CR １ or W １ ~W ６ All of this is CR １ and W １ ~W ６ All of this is 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 and preferably do not both represent N, and W ９ and W １０ and preferably do not both represent N, and W １１ and W １２ and preferably do not both represent N, and W １３ and W １４ and preferably do not both represent N, and W １４ represents N, and W ７ ~W １３ is CR １ or W ７ ~W １４ All of this is CR １ and W ７ ~W １４ All of this is 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 R , they may be the same or different. 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. 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 this is CR １ and W １ ~W ６ All of this is 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 greater. 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, as this facilitates an improvement in Δn and lightfastness in air, and m may be 0.

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

[0073] In the case where m represents 0 and A represents a group represented by formula (A-1), the group represented by formula (A-1) may be substituted with one or more substituents E. In this case, the presence of a bond between the group represented by formula (A-1), such as a naphthyl group, and S (sulfur atom) is preferred, as this facilitates an improvement in Δn and lightfastness 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, the valence of the sulfur atom can assume a high valence state from divalent to tetravalent to hexavalent, and therefore 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), in particular, because it is easy to improve Δn and light resistance in air.

[0075] (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 ２When 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), in particular, because it is easy to improve Δn, it is easy to improve light fastness in air, and it has excellent solvent solubility.

[0078] (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, k2 represents an integer of 0 to 4, 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.

[0079] In the general formulas (I-1) and (I-2), k1 represents an integer of 0 to 6. From the viewpoints 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 may be 0 or 1, and may also 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, this is preferable from the viewpoint of orientation. In the general formulas (I-1) and (I-2), n' represents an integer of 0 to 2. From the viewpoints of solvent solubility and phase transition temperature, n' may be 1 or 2, and may also be 1.

[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 formula (I), and may be the same as above.

[0081] In the general formulas (I-1) and (I-2), Z is preferably used in order to fix the alignment state of the compound represented by the general formula (I) and improve the durability of the optically anisotropic medium. １ In particular, Z preferably represents a polymerizable group from the viewpoint of reactivity. 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 viewpoint 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 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. １ and Z ２ In the formula (Z-1), R ｚ is preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom. In the following chemical formulae, Me represents a methyl group.

[0085]

[0086]

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

[0088]

[0089]

[0090]

[0091]

[0092]

[0093] The compound represented by general formula (I) can be produced, for example, by the following production method. Examples of the production method include 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 "Methoden der Organischen Chemie," "Organic Reactions," "Organic Syntheses," "Comprehensive Organic Synthesis," "New Experimental Chemistry Lectures," etc.) that are appropriately combined depending on the structure of the compound. Specific examples of the synthesis of the compound represented by general formula (I) are shown in the examples described 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-type 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, when an optically anisotropic layer is prepared from a composition containing the compound represented by general formula (I), the compound represented by general formula (I) is easily aligned, and a desired alignment pattern can be easily prepared, which is preferable. 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 prepared.

[0096] The term "a compound has 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 100°C or lower, or even 90°C or lower, which broadens the range of substrates that can be used and allows for easier handling. If the liquid crystal compound is solid at room temperature, it will be excellent in the drying step in the manufacturing process, in weighing during ink preparation, and in storage stability. When the compound represented by general formula (I) has liquid crystallinity, the phase transition temperature is a solid-liquid crystal transition temperature, and when the compound represented by 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). Measurements are performed in accordance with JIS K7121-1987, Section 8. The phase transition temperature is the extrapolated melting initiation temperature (Tim) value according to JIS K7121-1987, Section 9.1(2). However, the heating and cooling program (heating rate, cooling rate, heating start temperature, end temperature) is performed as follows. 5 mg of the measurement sample is sealed in an aluminum sample pan and set in the DSC. Under a nitrogen atmosphere, the sample is cooled from 25°C to -10°C at a rate of -25°C / min and maintained at -10°C for 15 minutes. Thereafter, as the first heating run, the sample is heated from -10°C to 150°C at a rate of 10°C / min and maintained at 150°C for 1 minute. In the first cooling run, the sample 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 sample is heated from -10°C to 150°C at a rate of 10°C / min and maintained at 150°C for 1 minute. In the second cooling run, the sample is cooled from 150°C to 25°C at a rate of -10°C / min. The endothermic onset temperature detected in the second heating run, 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 line 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 both the present examples and comparative examples, the DSC measurements were performed with an upper limit temperature of 150°C. However, in the case of a compound that initiates polymerization by 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 using the following steps i) to iii) and the upper limit temperature during the DSC measurement is determined. i) The temperature reached during the first heating is set to 150°C. If no peak is detected or the peak area is significantly reduced during the second heating, a new DSC measurement is performed under conditions where the temperature reached during the first heating is lowered by 5°C. ii) If no peak is detected or the peak area is significantly reduced during the second heating even after lowering the temperature reached during the first heating by 5°C, a new DSC measurement is performed under conditions where the temperature reached during the first heating is further lowered by 5°C. iii) The above step ii) is repeated 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 of the DSC measurement (upper limit of the heating temperature).

[0100] The compound represented by the general formula (I) is a compound having 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 one solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone, 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, relative to the total mass of the solid content in the composition, or 100% by mass or less, or 99% by mass or less. The solid content refers to components other than the solvent in the composition (non-volatile content). Components other than the solvent are considered to be solids even if they are liquid in nature. The composition may use one compound represented by general formula (I) alone, or two or more compounds. When two or more compounds are used, it is preferable that the total content is within the above range.

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

[0104] The term "liquid crystallinity" used herein 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 components 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 a liquid crystal compound (also referred to as "other liquid crystal compounds") other than the compound represented by general formula (I). 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. In addition, the other liquid crystal compound 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 １ and Z ２ The number of polymerizable groups contained in the liquid crystal compound having a polymerizable group 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. In addition, by mixing the compound represented by general formula (I) with the other liquid crystal compound, the crystallization temperature as a whole can be significantly reduced.

[0111] Other examples of liquid crystal compounds include those 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-T-11-513019, JP-T-2001-505879, JP-T-2001-527570, JP-A-6-16616, JP-A-7-110469, JP-A-11-80081, and compounds described in JP-A-2001-328973 and the like can be mentioned. 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 WO 2019 / 074007, the liquid crystal compound represented by the general formula (II) of WO 2017 / 043438, Japanese Patent Nos. 5463666, 4186981, 5962760, and 5826759, 6568103, 6427340, JP-A 2016-166344, and 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] (In general formula (II), Z １ , Z ２ , R ｓｐ１ , and R ｓｐ２ Each independently represents the same as defined in the general formula (I). ４ and L ５ 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-, -SO２ -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-, -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 R's, they may be the same or different. ３ are 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 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 in the general formula (I) above. p is an integer of 2 to 6. L ４ and T ３ When a plurality of groups are present, they may be the same or different. When a plurality of substituents E or groups selected from the following general formula (D-1) are present, they may be the same or different.

[0114] (In general formula (D-1), G １ represents 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; １represents an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group, any carbon atom of which 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 is -O-, -S-, -COO-, -OCO-, -OCO-O-, -NQ ２ -, -N=CQ ２ --CO-NQ ２ --, --OCO-NQ ２ -or-O-NQ ２ represents -, and 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 The alkyl group, the cycloalkyl group, the cycloalkenyl group, and the 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 the cycloalkenyl group, and one —CH ２ - or two or more non-adjacent -CH ２ - each independently represents -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, or -SO ２ -, -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-, and one -CH in the cycloalkyl group or cycloalkenyl group may be replaced by ２ - or two or more non-adjacent -CH ２ Each - may be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O-; ６ , R ｓｐ２ , and Z ２ are the L ５ , Rｓｐ２ , and Z ２ Each of the above L ５ , R ｓｐ２ , and Z ２ 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. Furthermore, 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). ４ Among R ｓｐ１ L binds to ４ , and L ５ is preferably L in the general formula (I). ３ It may be the same as that described in . ｓｐ１ L not bound to ４ is preferably L in the general formula (I). １ and L ２ It may be the same as 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 of 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 ２In view of the ease of obtaining raw materials for the compound represented by general formula (II) and the ease of synthesis, ３ are each independently preferably a group represented by the above general formula (B-1), (B-2), (B-2-2), (B-3), (B-4) or (B-10), more preferably a group represented by the above general formula (B-1), (B-2), (B-2-2) or (B-10). p is preferably 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, relative to the total mass of the solid content 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, relative to the total mass of the solid content in the composition. The composition of the present disclosure may use one type of other liquid crystal compound alone, or two or more types. When two or more types are used, it is preferable that the total content is within the above range.

[0118] <Polymerization initiator> The composition of the present disclosure may contain 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 that can start a polymerization reaction by ultraviolet irradiation. In the present embodiment, the photopolymerization initiator can be appropriately selected from conventionally known photopolymerization initiators and used. Specific examples of such photopolymerization initiators include aromatic ketones including thioxanthone and the like, 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 allows the coating film to be cured to the inside and improves durability.

[0119] Examples of the acylphosphine oxide polymerization initiator include bis(2,4,6-trimethylbenzoyl)-phenyl-phosphine oxide (for example, trade name: Omnirad 819, manufactured by IGM RESINS B.V.), 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 B.V.).

[0120] Furthermore, examples of the α-aminoalkylphenone polymerization initiator include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (e.g., Omnirad 907, manufactured by IGM Resin's B.V.), 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (e.g., Omnirad 369, manufactured by IGM Resin's B.V.), and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone (Omnirad 379EG, manufactured by IGM Resin's B.V.).

[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 (e.g., trade name: Omnirad 127, manufactured by IGM Resins B.V.), 2-hydroxy-4′-hydroxyethoxy-2-methylpropiophenone (e.g., trade name: Omnirad 2959, manufactured by IGM Resins B.V.), 1-hydroxy-cyclohexyl-phenyl-ketone (e.g., trade name: Omnirad 184, manufactured by IGM Resins B.V.), oligo{2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone} (e.g., trade name: ESACURE ONE, manufactured by IGM Resins B.V.), Resins B.V., etc.).

[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 Agent> The composition of the present disclosure may contain a chiral agent. When the composition of the present disclosure contains a chiral agent, a cholesteric phase can be formed. 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 chiral agents include those described in JP-A-08-245960, EP 1816180, 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 type of chiral agent alone, or two or more types. When two or more types 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 types. 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 composition of the present disclosure may contain a surfactant that contributes to stable or rapid formation of a liquid crystal phase (e.g., a nematic phase, a cholesteric phase). Examples of the surfactant include fluorine-containing (meth)acrylate polymers, compounds represented by general formulas (X1) to (X3) described in WO 2011 / 162291, compounds represented by general formula (I) described in paragraphs

[0082] to

[0090] of JP-A 2014-119605, and compounds described in paragraphs

[0020] to

[0031] of JP-A 2013-47204. Examples of fluorine-containing (meth)acrylate polymers that can be used as surfactants include polymers described in paragraphs

[0018] to

[0043] of JP-A 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 type of surfactant alone, or two or more types. When two or more types 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. Optical Anisotropic Body The optical anisotropic body of the present disclosure is an optical anisotropic body in which the compound represented by general formula (I) in the composition of the present disclosure is aligned. The optical anisotropic body of the present disclosure may be an optical anisotropic body that is a cured product of a composition containing the polymerization initiator of the present disclosure. The optical anisotropic body of the present disclosure may also be an optical 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 optical anisotropic body may be a solidified product. The method for immobilizing 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 a 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 method 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 heat-treating the composition layer 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, thereby forming an optically anisotropic body (e.g., an optically anisotropic layer). Note that the term "optically anisotropic body" refers to a substance having optical anisotropy. Having optical anisotropy means having a property in which the refractive index varies depending on the polarization direction. For example, this can be confirmed by observing an optically anisotropic body placed between two polarizing plates in a crossed Nicol configuration and rotating it, whereby 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 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 of contacting the support with the composition is not particularly limited, and examples thereof include a method of applying the composition to the support. As described above, an alignment film is preferably provided on the support, and the alignment film can be provided by a conventionally known method. The application method may be selected appropriately as long as it can accurately form a film with the desired thickness. Examples include gravure coating, reverse coating, knife coating, dip coating, spray coating, air knife coating, spin coating, roll coating, printing, immersion and lifting, curtain coating, die coating, casting, bar coating, extrusion coating, and E-type application.

[0130] The orientation step is a step of subjecting the composition layer to a heat treatment to align the compound represented by general formula (I). The composition layer is heated to a temperature at which the compound represented by general formula (I) contained in the composition layer can be oriented. This heat treatment allows the compound represented by general formula (I) and, if necessary, other liquid crystal compounds to be oriented and dried, and the composition can be fixed while maintaining the orientation state. The temperature at which orientation is possible varies depending on the substances in the composition, and therefore needs to be adjusted appropriately. For example, the heating is preferably performed within a range of 60°C to 200°C, more preferably within a range of 60°C to 100°C. Known heating and drying methods can be appropriately selected and used as the heating means. The heating time may be appropriately selected, for example, within a 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 necessary. The curing method is not particularly limited, and examples thereof include photocuring and thermal curing. Among these, photoirradiation is preferred, and ultraviolet irradiation is more preferred. As the photoirradiation, ultraviolet irradiation is suitably 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, or the like 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. More specifically, for example, the state in which a cholesteric liquid crystal phase is "fixed" is the most typical and preferred state in which the orientation 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 orientation without causing changes in the orientation due to external fields or external forces, 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 (e.g., 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 an 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 component 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.

[0136] D. Optical Element The optical element of the present disclosure is an optical element having an optically anisotropic layer formed using the composition of the present disclosure. The optical element of the present disclosure may have an optically anisotropic layer formed using the composition of the present disclosure, the optically anisotropic layer having an alignment pattern, the alignment pattern being an alignment pattern in which the orientation of the optical axis derived from the liquid crystal compound contained in the composition undergoes continuous rotational change along at least one direction in the plane. The alignment pattern is preferably an alignment pattern in which the orientation of the optical axis derived from the compound represented by general formula (I) undergoes continuous rotational change along at least one direction in the plane, or an alignment pattern in which the orientations of the optical axes derived from the compound represented by general formula (I) and other liquid crystal compounds undergo continuous rotational change along at least one direction in the plane. The optical element of the present disclosure has an alignment pattern in which the orientation of the optical axis undergoes continuous rotational change along at least one direction in the plane, thereby enabling light incident on the optical element to be diffracted. The compound represented by general formula (I) has a high refractive index anisotropy Δn, and therefore can achieve high 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 alignment pattern, and the alignment pattern is an alignment pattern in which the orientation of the optical axis derived from the liquid crystal compound contained in the composition is continuously rotated along at least one direction in the plane. For details of the optical element, see, for example, paragraphs

[0067] to

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

[0035] to

[0072] of JP-A-2017-31379.

[0137] The optical element of the present disclosure can be applied as an optical member of an augmented reality (AR) image projection device, etc. 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 optically anisotropic body of the second present disclosure is a cured product of a polymerizable liquid crystal composition containing a partial structure represented by the following general formula (Ia):

[0139] (In general formula (Ia), the 2,6-naphthyl group may be substituted by one or more substituents E, and k1 represents an integer of 0 to 6. Each substituent E 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 the substituents E are not —CH ２ When - is contained in the above group, -CH ２ Substituent E also includes groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above groups described as substituent E have a hydrogen atom, substituent E also includes 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. ** represents the bonding position to another atom.

[0140] The optically anisotropic body of the second disclosure is a cured product of a polymerizable liquid crystal composition, and yet contains a partial structure of general formula (Ia), thereby exhibiting an improved refractive index anisotropy Δn and suppressing cracking. 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 a wider π-conjugated resonance. Since the optically anisotropic body of the second disclosure contains the partial structure of general formula (Ia), the -S-naphthalene-COO- structure expands π electrons toward the 2- and 6-positions of naphthalene, improving the refractive index toward the 2- and 6-positions of naphthalene, presumably resulting in an increase in refractive index anisotropy Δn. It is also presumed that the increase in refractive index anisotropy Δn is due to the synergistic effects of the large polarizability of sulfur atoms and intermolecular S-S interactions. Furthermore, when the partial structure of general formula (Ia) is included, the bond angle of -S- adjacent to naphthalene is greatly bent, and it is presumed that even when deformation is applied, this bond is elongated, thereby obtaining sufficient extensibility. Therefore, it is presumed that by including the partial structure of general formula (Ia), the optical anisotropic body of the second disclosure is less susceptible to cracking while having improved refractive index anisotropy Δn. The optical anisotropic body of the second disclosure has improved flex resistance, is less susceptible to cracking even when flexed, and is excellent in lamination properties and processability.

[0141] The optical anisotropic body of the second 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. 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 measurements taken at three locations is used as the measurement result. In addition, when the optical anisotropic body is laminated with a substrate having a retardation such as polyethylene terephthalate (PET), a measurement sample is prepared by transferring the optical anisotropic body to a glass plate with an adhesive layer (optical adhesive, Panaclean PD-S1 manufactured by Panac Corporation) that does not have a retardation, and the in-plane retardation Re is measured. (Re measurement conditions) Retardation measurement range: Rotating analyzer method Measurement spot diameter: φ5 mm Tilt angle range: 0° Measurement wavelength range: 400 nm to 800 nm (Layer thickness measurement) The layer thickness of the optically anisotropic body (optically anisotropic layer) is measured by photographing a cross section of the optically anisotropic body using a scanning transmission electron microscope (STEM) (Hitachi High-Technologies Corporation, S-4800), measuring the thickness of the optically anisotropic body at 10 locations in the image of the cross section, and calculating the arithmetic average value of the layer thicknesses at those 10 locations. A cross-sectional photograph of the optically anisotropic body is taken as follows. First, a sample cut to 1 mm x 10 mm is embedded in an embedding resin to prepare a block, and a uniform slice with a thickness of 70 nm to 100 nm without holes is cut from this block using a general slice preparation method. An ion milling device (Hitachi High-Technologies Corporation, IM-4000II) is used to prepare the slice. This uniform slice without holes or the like is used as the measurement sample. A cross-sectional photograph of the measurement sample is then taken using a scanning transmission electron microscope (STEM). When taking this cross-sectional photograph, STEM observation is 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 appropriately from 5,000x to 200,000x 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 present disclosure may be one that shows no cracks when a cylindrical mandrel method in accordance with JIS-K5600-5-1:1999 is used and the bent portion of the mandrel has a diameter of 3 mm is observed with a 10x magnifying glass.

[0143] The optically anisotropic body of the second 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 optically anisotropic body of the second 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 apparatus: TOF. SIMS manufactured by ION-TOF Inc. ５ Primary ion species: Bi ３ ＋＋ Primary ion acceleration voltage: 25 kV Primary ion current value: 0.2 pA Measurement area: 200 μm × 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. In terms 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 optical anisotropic body of the second present disclosure may be a cured product of a polymerizable liquid crystal composition containing a compound containing a partial structure of general formula (Ia). The compound containing the partial structure of general formula (Ia) does not have 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) contained 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 general formula (I-1) and the compound represented by general formula (I-2) may be the same as the compounds described in the first 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 their contents may be the same as those described in the composition of the first present disclosure. The other liquid crystal compounds may also be the same as those described in the composition of the first present disclosure. The compound represented by general formula (II) may be a compound represented by general formula (II) (however, different from the compound containing the partial structure of general formula (Ia)). The cured product of the polymerizable liquid crystal composition, which is the optical anisotropic body of the second present disclosure, may not contain a polymerization initiator, since some polymerization initiators decompose.

[0149] In the optical anisotropic body of the second disclosure, it is preferable that the compound having the partial structure of general formula (Ia) is contained in an amount of 4% by mass or more from the viewpoint of refractive index anisotropy and suppression of crack generation. In the optical anisotropic body of the second disclosure, the compound having 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 measured by the Fourier transform infrared spectrophotometer (FT-IR) by the ATR method －１ ~1225cm －１ The peak intensity of the S-C 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 1205 cm to the peak intensity of the C═C bond (P1) located at 1205 cm 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. －１ ~1225cm －１ The S-C bond peak located at 1600 cm represents the S-C 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 the surface hardness of the film. Furthermore, from the viewpoint of refractive index anisotropy and crack suppression, a peak at 1205 cm measured by a Fourier transform infrared spectrophotometer (FT-IR) using the ATR method is －１ ~1225cm －１ The peak intensity of the S-C bond (P1) located at 1700 cm －１ ~1750cm －１The ratio (P1 / P3) of the peak intensity of the C═O bond (P3) located at 1205 cm measured by a Fourier transform infrared spectrophotometer (FT-IR) using the ATR method may be 0.10 or more and 0.80 or less. The P1 / P3 ratio may be 0.30 or more, or 0.50 or more. Furthermore, from the viewpoint of refractive index anisotropy and suppression of crack generation, the ratio (P1 / P3) of the peak intensity of the C═O bond located at 1205 cm measured by a Fourier transform infrared spectrophotometer (FT-IR) using the ATR method may be 0.10 or more and 0.80 or less. －１ ~1225cm －１ The peak intensity (P1) of the S—C bond 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 at the position P1 to the sum of the peak intensities (P3) of the C═O bonds at the positions P2 and P3 may be 0.10 or more and 0.80 or less. The ratio P1 / (P2+P3) may be 0.15 or more, or 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 attached to the measurement device. (FT-IR measurement conditions) The surface of the optically anisotropic medium is measured using a Fourier transform infrared spectrophotometer (FT-IR) by the ATR method. If necessary, the surface of the optically anisotropic medium is exposed before measurement. Measurement device: Fourier transform infrared spectrophotometer (manufactured by JASCO Corporation, an FT-IR6100 equipped with an ATR-PRO470-H) Light source: High-intensity 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: φ1.5 mm Number of measurements: 32

[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. Note that these layers no longer need to exhibit liquid crystallinity. More specifically, for example, the state in which the cholesteric liquid crystal phase is "fixed" is the most typical and preferred embodiment in which the orientation of the compound containing the partial structure of general formula (Ia) that has become a cholesteric liquid crystal phase is maintained.

[0154] The thickness of the optically anisotropic body (e.g., the 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. Examples of 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 disclosure is an optical element having the optical anisotropic body of the second disclosure as an optically anisotropic layer. The optical element of the second disclosure may also be an optical element having the optical anisotropic body of the second disclosure as an optically anisotropic layer, the optically anisotropic layer having an alignment pattern, the alignment pattern being an alignment pattern in which the direction of the optical axis derived from the compound having liquid crystal properties contained in the composition is continuously rotated along at least one direction in the plane. The optical element of the second disclosure can be appropriately applied to conventionally known optical elements including the optically anisotropic layer. The optical element of the second disclosure may be similar to the optical element described in the first disclosure.

[0157] Each compound was analyzed using a Bruker AVANCE (400 MHz) spectrometer. １ The chemical structure was confirmed by H NMR measurement. In the present disclosure, the in-plane retardation Re and various parameters of FT-IR in the following evaluation items mean the average value of measured values ​​at three locations unless otherwise specified. The three measurement locations are the centers of measurement at the three intersections of a line dividing the vertical direction of a rectangular measurement sample into four equal parts and a line dividing the horizontal direction into two equal parts. The vertical direction of the rectangle is the long side direction. In addition, when 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 these shapes is drawn, and three locations of the rectangle are measured using the above method.

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

[0159]

[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 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 washed with water. The resulting solid was reslurried and purified in methanol to obtain 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). The yield was 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, potassium hydroxide (4.3 g, 85.8 mmol) in water (40 mL) was added, 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 obtain compound 3 (5.6 g, 27.3 mmol). The yield was 95.5%.

[0163] (4) Synthesis of Compound 4 Dimethylacetamide (DMAc) (200 mL) was added to 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). The resulting mixture was stirred at 80°C for 3 hours. A solution of sodium hydroxide (9.4 g, 235.0 mmol) (water 200 mL, methanol 50 mL) 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 in the resulting organic layer was evaporated under reduced pressure. The resulting solid was reslurried and purified in diisopropyl ether to obtain 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 thereto, followed by stirring 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 obtain 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 CH ２ Cl ２ (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto, followed by stirring 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-1 (3.7 g, 5.0 mmol). The yield was 99.5%. １H-NMR (CDCl ３ ): 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]

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

[0168]

[0169] (1) Synthesis of Compound 6 Compound 3 was synthesized in the same manner as in Production 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) (water 200 mL, methanol 50 mL) 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, followed by stirring 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 obtain 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 CH ２ Cl ２ (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto, followed by stirring 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-2 (4.2 g, 4.8 mmol). The yield was 96.5%. １ H-NMR (CDCl ３ ): 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 Production 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 CH ２ Cl ２(6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto, followed by stirring 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-3 (3.4 g, 4.5 mmol). The yield was 90.5%. １ H-NMR (CDCl ３ ): 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]

[0174] [Production Example 4: Production of Compound A-4] Compound 5 was synthesized in the same manner as in Production 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 CH ２ Cl ２ (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto, followed by stirring 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 (CDCl ３ ): 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]

[0176] [Production Example 5: Production of Compound A-5] Compound 5 was synthesized in the same manner as in Production 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 CH ２ Cl ２ (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15 mmol) was added dropwise thereto, followed by stirring 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 (CDCl ３ ): 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, 2H), 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]

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

[0179]

[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 the mixture was 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, and then N,N-diisopropylcarbodiimide (1.9 g, 15.0 mmol) was added dropwise, and the mixture was stirred at 15°C for 3 hours. To the resulting mixture, 35% hydrochloric acid (10 mL) was added, and the mixture was 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 obtain 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 Production 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 CH ２ Cl ２ (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.8 g, 6 mmol) was added dropwise thereto, followed by stirring 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 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 CH ２ Cl ２ (2 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.3 g, 2.0 mmol) was added dropwise thereto, followed by stirring at 15°C for 3 hours. Methanol (10 mL) was added to the resulting mixture, which was then filtered. The residue was washed with methanol to obtain compound A-6 (0.7 g, 0.9 mmol). The yield was 91.5%. １H-NMR (CDCl ３ ): 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), 7.20 (m, 5 H), 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 Production 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 CH ２ Cl ２ (2 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.3 g, 2.0 mmol) was added dropwise thereto, followed by stirring at 15°C for 3 hours. Methanol (10 mL) was added to the resulting mixture, which was then 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 (CDCl ３ ): 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]

[0185] [Production Example 8: Production of Compound A-8] Compound 9 was synthesized in the same manner as in Production 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 CH ２ Cl ２(2 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.3 g, 2.0 mmol) was added dropwise thereto, followed by stirring at 15°C for 3 hours. Methanol (10 mL) was added to the resulting mixture, and the residue obtained by filtration was washed with methanol to obtain compound A-8 (0.5 g, 0.9 mmol). The yield was 93%. １ H-NMR (CDCl ３ ): 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, 1 H), 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]

[0187] [Production Example 9: Production of Compound A-9] Compound 5 was synthesized in the same manner as in Production 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 CH ２ Cl ２ (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (0.8 g, 6.0 mmol) was added dropwise thereto, followed by stirring 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]

[0189] [Production Example 10: Production of Compound A-10] Compound A-10 was synthesized according to the following scheme. １ H-NMR (CDCl ３): 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]

[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 the mixture was 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 obtain 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 obtain Compound 11 (26.9 g, 97.5 mmol). The yield was 100%.

[0193] (3) Synthesis of Compound 12 Compound 11 (22.1 g, 80.0 mmol) was dissolved in methanol (250 mL). To the resulting solution, an aqueous solution of potassium hydroxide (13.5 g, 240.0 mmol) (120 mL of water) was added, 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 obtain 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 resulting mixture was stirred at 80°C for 3 hours. A solution of sodium hydroxide (14.0 g, 350.0 mmol) (water 70 mL, methanol 70 mL) 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 (700 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 obtain 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 thereto, followed by stirring 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 obtain 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 CH ２ Cl ２ (50 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (7.6 g, 60.0 mmol) was added dropwise thereto, followed by stirring 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 obtain compound A-10 (14.2 g, 18.9 mmol). The yield was 94.5%. １ H-NMR (CDCl ３): 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]

[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 obtain 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 obtain Compound 16 (8.5 g, 28.1 mmol). The yield was 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, potassium hydroxide (4.2 g, 75.0 mmol) in water (75 mL) was added, 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 obtain 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 in 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 thereto, followed by stirring 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 obtain 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 CH ２ Cl ２ (4 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.1 g, 9.0 mmol) was added dropwise thereto, followed by stirring 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 obtain compound A-11 (2.2 g, 2.7 mmol). The yield was 91.5%. １ H-NMR (CDCl ３): δ = 1.98 (m, 8H), 2.33 (s, 3H), 3.23 (t, 4H), 4.09 (t, 4H), 5.88 (dd, 2H), 6.4 1 (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]

[0207] (1) Synthesis of Compound 20 4-Amino-3-hydroxybenzoic acid (7.7 g, 50.0 mmol) and potassium ethylxanthate (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 in diisopropyl ether to obtain compound 21 (9.2 g, 28.7 mmol). The yield was 95.5%.

[0209] (3) Synthesis of Compound 22 Compound 21 (7.7, 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 thereto, followed by stirring 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 obtain 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 CH ２ Cl ２ (6 mL). The resulting solution was cooled to 15°C, and N,N-diisopropylcarbodiimide (1.9 g, 15.0 mmol) was added dropwise thereto, followed by stirring 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-12 (3.6 g, 4.9 mmol). The yield was 98.0%. １ H-NMR (CDCl ３ ): 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), 6.4 1 (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]

[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 evaporated 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 obtain 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 (PPh ３ ) (2.1g, 8.0mmol), Pd(PPh ３ ) ２ Cl ２ (2.8 g, 4.0 mmol), dibutylhydroxytoluene (BHT) (0.2 g, 1.0 mmol), Et ３ N (1000 mL) was 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, followed by stirring at room temperature for 18 hours. Water and ethyl acetate were added to the resulting mixture, which was then extracted with ethyl acetate, and the solvent in the organic layer was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to obtain 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), PPh ３ (2.0g, 7.6mmol), Pd(PPh ３ ) ２ Cl ２ (2.7 g, 3.8 mmol), BHT (0.2 g, 1.0 mmol) and Et ３N (950 mL) was 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, followed by stirring under heating to reflux for 3 hours. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate, and the solvent in the organic layer was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to obtain 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, followed by extraction with ethyl acetate. The solvent in the resulting organic layer was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to obtain 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), PPh ３ (1.1g, 4.0mmol), Pd(PPh ３ ) ２ Cl ２ (1.4 g, 2.0 mmol), BHT (0.2 g, 1.0 mmol) and Et ３ N (500 mL) was 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, followed by stirring at room temperature for 18 hours. Water and ethyl acetate were added to the resulting mixture, followed by extraction with ethyl acetate, and the solvent in the organic layer was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to obtain 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, followed by stirring 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 purified by flash column chromatography to obtain comparative compound RA-1 (17.6 g, 39.0 mmol). The yield was 97.5%. １ H-NMR (CDCl ３ ): 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 Production Example 2: Production of Comparative Compound RA-2 Comparative compound RA-2 was produced with reference to JP-A-2008-544954.

[0220]

[0221] Comparative Production Example 3: Production of comparative compound RA-3 Comparative compound RA-3 was produced with reference to JP-A-2008-544954.

[0222]

[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]

[0225] Comparative Preparation Example 5: Preparation of comparative compound RA-5 Comparative compound RA-5 was prepared with reference to Japanese Patent No. 5,962,760.

[0226]

[0227] [Example 1] Compound A-1 was used in Example 1 to perform the following evaluations. (1) Phase Transition Temperature Measurement 5 mg of Compound A-1 was placed in an aluminum sample pan as a measurement sample, and then set in a differential scanning calorimeter (DSC) (Shimadzu Corporation, DSC-60). The sample was cooled from 25°C to -10°C at a rate of -25°C / min under a nitrogen atmosphere and maintained at -10°C for 15 minutes. Thereafter, as a first temperature increase, 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, 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 temperature increase, 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. The second cooling was performed from 150°C to 25°C at a rate of -10°C / min. The endothermic onset temperature detected in the second temperature increase, 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 taken as the phase transition temperature. (Evaluation criteria for phase transition temperature) A: Phase transition temperature less than 90°C B: Phase transition temperature 90°C or higher but less than 110°C C: Phase transition temperature 110°C or higher The lower the phase transition temperature, the better the coatability.

[0228] (2) Production of composition and optically anisotropic body, and measurement of Δn (refractive index anisotropy) A composition containing a compound having the following composition was produced, and an optically anisotropic layer produced using this composition was used to calculate the Δn of Compound A-1. Since 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 Compound A-1. <Composition> Compound A-1 100 parts by mass Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad 907, manufactured by IGM RESINS B.V.) 5 parts by mass Methyl ethyl ketone 450 parts by mass

[0229] <Optical Anisotropic Body> 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] <Measurement of Δn (refractive index anisotropy)> The in-plane retardation Re and layer thickness (nm) of the manufactured optically anisotropic layer were measured, and Δn was calculated using the following formula: Δn = Re / layer thickness (nm) Re was measured at a wavelength of 550 nm using a retardation measurement device (RETS-100 manufactured by Otsuka Electronics Co., Ltd.) and a set temperature of 25°C. The average value of measurements taken at three locations was used as the measurement result. (Re measurement conditions) Retardation measurement range: Rotating analyzer method Measurement spot diameter: φ5 mm Tilt angle range: 0° Measurement wavelength range: 400 nm to 800 nm The thickness of the optically anisotropic layer was measured using a scanning transmission electron microscope (STEM) (S-4800 manufactured by Hitachi High-Technologies Corporation) by photographing a cross section of the optically anisotropic layer and measuring the thickness of the optically anisotropic layer at 10 locations on the image of the cross section, and the arithmetic average value of the layer thicknesses at those 10 locations was used. Cross-sectional photographs of the optically anisotropic layer were taken as follows. First, a sample cut to 1 mm x 10 mm was embedded in an embedding resin to prepare a block. From this block, uniform slices with a thickness of 70 nm to 100 nm and no holes were cut using a general slice preparation method. An ion milling device (IM-4000II, manufactured by Hitachi High-Technologies Corporation) was used to prepare the slices. These uniform slices without holes were used as measurement samples. Cross-sectional photographs of the measurement samples were then taken using a scanning transmission electron microscope (STEM). When taking these cross-sectional photographs, STEM observations were performed with the detector set to "TE," the acceleration voltage set to "30 kV," and the emission current set to "10 μA." The magnification was adjusted appropriately from 5,000x to 200,000x while adjusting the focus and observing the contrast and brightness to see if 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 lightfastness test was carried out.

[0232] <Laminate for light resistance test> (Preparation of ultraviolet absorbing layer) Referring 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. On one side of a triacetyl cellulose resin film (TAC) substrate (Fujifilm Corporation, TD80UL, thickness 80 μm), a coating solution for forming an ultraviolet absorbing layer was applied, which was prepared by adding 5 parts by mass of a photopolymerization initiator (Omnirad 907, manufactured by IGM Resins B.V.) 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 ), and 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 the refractive index anisotropy Δn using an optical pressure-sensitive adhesive. As the optical pressure-sensitive adhesive, an optical pressure-sensitive adhesive (trade name: Panaclean PD-S1, 25 μm, manufactured by Panac Corporation, acrylic pressure-sensitive adhesive) with a thickness of 25 μm was used.

[0233] <Light resistance test> The optically anisotropic layer of the prepared laminate for light resistance test 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 lightfastness test was carried out under the conditions of 1000 nm to 4800 nm irradiation time. The Re of the optically anisotropic layer was measured before and after the lightfastness 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 less than 10% B: Re change rate 10% or more and less than 15% C: Re change rate 15% or more The smaller the Re change rate, the more excellent the lightfastness.

[0234] [Example 2] The following evaluations were carried out using Compound A-2 in Example 2. (1) Measurement of Phase Transition Temperature 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 in Example 1.

[0235] (2) Production of Composition and Optically Anisotropic Element, and Measurement of Δn (Refractive Index Anisotropy) Since compound A-2 did not align on its own, compositions containing other liquid crystal compounds were produced according to the following formulations, and Δn was determined in the same manner as in Example 1 using optically anisotropic layers produced using these compositions. 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, which contained 20 parts by mass, 10 parts by mass, and 0 parts by mass of compound A-2, respectively. A simple linear regression analysis was performed from the obtained measured values ​​to determine the refractive index anisotropy Δn when the amount of compound A-2 was 100 parts by mass. The regression coefficients a and b of the following regression equation, where y is the refractive index anisotropy Δn and x is the parts by mass of compound A-2, were derived from the measured values ​​using the least squares method: y = ax + b Substituting x = 100 into the derived regression equation, 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: Omnirad 907, manufactured by IGM RESINS B.V.) 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 mass Photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: Omnirad 907, manufactured by IGM Resins B.V.) 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: Omnirad 907, manufactured by IGM Resins B.V.) 5 parts by mass Methyl ethyl ketone 450 parts by mass

[0236] (3) Lightfastness Evaluation The lightfastness evaluation was carried out 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 compositions and optically anisotropic layers, 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, 12, and Comparative Examples 1 and 3, the phase transition temperature measurement, the production of compositions and optically anisotropic layers, the measurement of Δn, 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]

[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 lightfastness in an air atmosphere, and reduced phase transition temperatures. In contrast, the compound of Comparative Example 1, which is a tolan compound, had poor lightfastness in an air atmosphere. The compound of Comparative Example 2, which corresponds to a compound having a 2,6-naphthyl group specifically described in Patent Document 1, had a high phase transition temperature, insufficient refractive index anisotropy Δn, and poor lightfastness. The compound of Comparative Example 3, which corresponds to a compound having a 2,6-naphthyl group specifically described in Patent Document 1 and had a specifically high refractive index anisotropy Δn, had a high phase transition temperature and poor lightfastness. 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—, was shown to have a lower phase transition temperature. Furthermore, the compound of Comparative Example 4, which is a compound having 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 element) A composition containing the compound A-1 of Example 1 was produced according to the following formulation, and an optical element was produced using the composition, including an optically anisotropic layer in which a cholesteric liquid crystal phase was fixed. <Composition> Compound A-1: ​​24.5 parts by mass Chiral agent (compound (Ch-1) below): 0.5 parts by mass Photopolymerization initiator (Omnirad 907, manufactured by IGM RESINS B.V.): 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 combining 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]

[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 photo-alignment film was applied by spin coating to one side of a PET substrate (manufactured by 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, polarized ultraviolet light containing a 313 nm emission line was applied to the surface of this cured coating film 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 Element> The composition was applied onto the formed alignment film so that the film thickness after curing would be about 4 μm, forming a film of a polymerizable liquid crystal composition. The film was then dried in an oven at 90° C. for 2 minutes, and then irradiated with ultraviolet (UV) rays at a dose of 400 mJ / cm using an H bulb manufactured by Fusion Corporation under a nitrogen atmosphere. ２An optically anisotropic layer was formed by irradiating the sample with light at a wavelength of 1000 nm to form an optically anisotropic layer, thereby producing an optical element. A cross-section of the optically anisotropic layer of the optical element was observed using a scanning transmission electron microscope (STEM). Observation of a repeated 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 ultrathin sections (80 nm thick) with smooth cross sections. The obtained ultrathin cross-sections were observed using STEM under the following measurement conditions (TE detector, accelerating voltage 30 kV, emission current 10 μA, magnification 5000x), and a cross-sectional image of the optically anisotropic layer of the optical element was obtained. A repeated structure of dark area-light area-dark area-light area, or light area-dark area-light area-dark area was confirmed in the cross-sectional image obtained using STEM.

[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 body 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: Omnirad 907, manufactured by IGM RESINS B.V.) 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 anisotropic body> The above composition was applied by a bar coating method to a 100 μm thick PET film (A4160: manufactured by Toyobo Co., Ltd.) that had been subjected to a rubbing treatment with nylon, so that the cured film thickness was 5 μm. The composition was heated to a temperature at which the composition exhibited a nematic phase, dried, and then irradiated with 240 mJ / cm 2 of a high-pressure mercury lamp. ２ The film was irradiated with ultraviolet light of 1000 kJ / cm to produce an optically anisotropic layer.

[0248] (1) Bending Resistance Test A test piece used in the bending resistance test was cut into a 50 mm x 20 mm square from near the center of the optically anisotropic body. The test piece was bent in the long side 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 when the bent portion of the optically anisotropic layer when the mandrel diameter was 3 mm was observed with a 10x magnifying glass. The fewer cracks there were, the better the bending resistance and the more excellent the lamination and processability. (Evaluation criteria for bending resistance) A: No cracks B: Cracks present

[0249] (2) Measurement of Δn (refractive index anisotropy) The composition was spin-coated onto the entire surface of a rubbed glass sheet (50 mm × 50 mm) with an alignment film. After heating the composition to a temperature at which it exhibited a nematic phase, Δn was measured at 244 mJ / cm ２ The optically anisotropic layer was then irradiated with ultraviolet light for 100 seconds to produce an optically anisotropic layer. Δn was calculated for the produced optically anisotropic layer 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 material for which the Δn measurement was performed 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: 1205 cm －１ ~1225cm －１ Peak intensity of S-C bond located at P2: 1600 cm －１ ~1650cm －１ Peak intensity of C═C bond located at P3: 1700 cm －１ ~1750cm －１FT-IR measurement was performed at three different positions on the sample. The average value of P1 at the three positions was taken as P1 for that sample. Similarly, the average values ​​of the measurements at the three positions 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 device: Fourier transform infrared spectrophotometer (manufactured by JASCO Corporation, an FT-IR6100 equipped with an ATR-PRO470-H) Light source: High-intensity 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: φ1.5 mm Number of integrations: 32 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: Omnirad 907, manufactured by IGM RESINS B.V.) 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] In Example II-6, a composition was prepared in the same manner as in Example II-5, except that compound A-4 was used instead of compound A-1 in Example II-5, and an optical anisotropic body was produced using the composition. In addition, 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.

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

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

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

[0258] As shown in Examples II-1 to II-8, optically anisotropic layers that are cured products of polymerizable liquid crystal compositions containing the partial structure represented by formula (Ia) of the present disclosure were 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 were poor in flex resistance.

Claims

1. A compound represented by the following general formula (I): (In general formula (I), Z １ and Z ２ R 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. 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-, -NH-CO-, or -CH=CH-, or a single bond. S represents a sulfur atom. L １ , 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 there are multiple R's, they may be the same or different. 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 of the following formulas (A-1) to (A-4), which 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, provided that the above groups described as substituent E are not —CH ２ When - is contained in the above group, -CH ２ Substituent E also includes groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above groups described as substituent E have a hydrogen atom, substituent E also includes 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. 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 of these, they may be the same or different. (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. １ ~Y ２ are each independently NR ２ , O or S, R ２ represents a hydrogen atom or the substituent E. * represents L １ , L ２ , L ３ , or represents the bonding position with S.) 2. The compound according to claim 1, wherein m in said general formula (I) represents 0, A represents a group represented by said formula (A-1), and said group represented by said formula (A-1) is optionally substituted with one or more substituents E.

3. The compound according to claim 1, represented by the following general formula (I-1): (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.) 4. The compound according to claim 1, represented by the following general formula (I-2): (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, k2 represents an integer of 0 to 4, 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.) 5. The compound according to any one of claims 1 to 4, which has liquid crystal properties.

6. A composition comprising a compound according to any one of claims 1 to 4.

7. The composition of claim 6, further comprising a polymerization initiator.

8. The composition of claim 6, further comprising a chiral agent.

9. An optically anisotropic medium in which the compound represented by formula (I) in the composition according to claim 6 is aligned.

10. An optically anisotropic body which is a cured product of the composition according to claim 7.

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

12. An optical element having an optically anisotropic layer formed using the composition according to claim 6.

13. An optical element having an optically anisotropic layer formed using the composition according to claim 6, wherein the optically anisotropic layer has an alignment pattern, and the alignment pattern is an alignment 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.

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): (In general formula (Ia), the 2,6-naphthyl group may be substituted by one or more substituents E, and k1 represents an integer of 0 to 6. Each substituent E 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 the substituents E are not —CH ２ When - is contained in the above group, -CH ２ Substituent E also includes groups in which at least one of - is replaced with -O-, -CO-, or -CH=CH-. In addition, when the above groups described as substituent E have a hydrogen atom, substituent E also includes 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. ** represents the bonding position to another atom.

15. The optically anisotropic body according to claim 14, 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).

16. 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 16. The optical anisotropic body according to claim 14, wherein the ratio (P1 / P2) of the peak intensity of the C=C bond located at the position (P1) to the peak intensity (P2) of the C=C bond located at the position (P1) is 0.30 or more and 1.80 or less.

17. An optical element having the optically anisotropic body according to claim 14 or 15 as an optically anisotropic layer.

18. An optical element having an optical anisotropic body according to claim 14 or 15 as an optically anisotropic layer, wherein the optically anisotropic layer has an alignment pattern, and the alignment pattern is an alignment 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.

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