Compound, composition, cured product, optically anisotropic body, optical element, and light guide element

Abstract

Provided are a compound represented by general formula (I), a composition containing a compound represented by general formula (I), a cured product, an optically anisotropic body, an optical element, and a light guide element. P1 and P2 each independently represent a hydrogen atom, -CN, -NCS, or a polymerizable group. Sp1 and Sp2 each independently represent a single bond or a specific linking group. Z1 represents a specific linking group. At least two instances of Z1 represent -C≡C-. The two instances of Z bonded to A2 in -Z-A2-Z- in general formula (I) do not represent -C≡C-. A1 and A2 each independently represent a specific group. The plurality of A2 may be the same or different. n represents an integer from 3 to 7.

Description

[Technical Field]

[0001] The present invention relates to a compound, a composition, a cured product, an optically anisotropic body, an optical element, and a light guide element. [Background technology]

[0002] A compound having liquid crystallinity (hereinafter also referred to as a "liquid crystal compound") and a composition having liquid crystallinity (hereinafter also referred to as a "liquid crystal composition") can be used in a variety of applications. For example, Patent Document 1 describes that an optical element having an optically anisotropic layer made of a cured product of a composition containing a liquid crystal compound can provide diffracted light with a large diffraction angle and high diffraction efficiency. Patent Document 1 also describes that good diffraction efficiency can be obtained by using a liquid crystal compound having high refractive index anisotropy Δn (hereinafter also simply referred to as "Δn"). Patent Documents 2 and 3 describe liquid crystal compounds having a high Δn. Patent Document 2 describes a reflective film obtained by curing a composition containing a liquid crystal compound having a high Δn. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2020 / 022496 [Patent Document 2] International Publication No. 2018 / 034216 [Patent Document 3] Japanese Patent Publication No. 2005-15406 Summary of the Invention [Problem to be solved by the invention]

[0004] As described in Patent Documents 1 to 3, liquid crystal compounds having a high Δn are useful in various applications. Furthermore, even if a compound having a high 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 Δn, which is useful in various applications.

[0005] An object of the present invention is to provide a compound having a high refractive index anisotropy Δn, a composition containing the compound, a cured product, an optically anisotropic body, an optical element, and a light guide element. [Means for solving the problem]

[0006] The present inventors have conducted extensive research and have found that the above problems can be solved by the following means. 〔1〕 A compound represented by the following general formula (I): [ka] In general formula (I), P 1 and P 2 are each independently a hydrogen atom, —CN, —NCS, or a group represented by any one of the following general formulae (P-1) to (P-19): Representing a polymerizable group S, P 1 and P 2 At least one of them represents a polymerizable group represented by any one of the following general formulas (P-1) to (P-19): vinegar. In the following general formulae (P-1) to (P-19), * represents a bonding position, Me represents a methyl group, and Et represents an ethyl group. [ka] Sp 1 and Sp 2 each independently represents a single bond, an alkylene group, an alkenylene group, -O-, -S-, -CO-, -SO-, or -SO 2 -, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -N(R 1 )-, or a divalent linking group formed by combining a plurality of these. 1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, provided that Sp 1 and Sp 2 does not represent a divalent linking group having a group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. However, Sp 1 -P 1 and Sp 2-P 2 However, neither of them is a methyl group. Z 1 -O-, -S-, -CHRCHR-, -OCHR-, -CHRO-, -CO-, -SO-, -SO 2 -, -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 represents -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CHRCHR-, -OCO-CHRCHR-, -CHRCHR-COO-, -CHRCHR-OCO-, -COO-CHR-, -OCO-CHR-, -CHR-COO-, -CHR-OCO-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=NN=CR-, -CF=CF- or -C≡C-. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When multiple Rs are present, the multiple Rs may be the same or different. Multiple Zs present 1 may be the same or different. However, two or more Z 1 represents -C≡C-. -Z in the above general formula (I) 1 -A 2 -Z 1 -A in 2 Two Z's bonded to do not represent -C≡C-. A 1 and A 2 each independently represents an aromatic hydrocarbon ring group or an aliphatic hydrocarbon ring group, each of which may have a substituent L, or a group formed by linking two groups selected from the group consisting of aromatic hydrocarbon ring groups and aliphatic hydrocarbon ring groups, each of which may have a substituent L. However, A connected with a triple bond 1 and A 2 At least one of the A's represents a group represented by the following general formula (A-1) or (A-2). 2 may be the same or different.

change

change

[10] . 〔12〕 The composition according to

[11] , further comprising a polymerization initiator. 〔13〕 The composition according to

[11] or

[12] , further comprising a chiral agent. 〔14〕 The composition according to any one of

[11] to

[13] , which has liquid crystal properties. 〔15〕 The composition according to any one of items

[11] to

[14] , which is for forming an optically anisotropic layer. 〔16〕 A cured product obtained by curing the composition according to any one of

[11] to

[15] . 〔17〕 An optically anisotropic body obtained by curing the composition according to any one of

[11] to

[15] . 〔18〕 An optically anisotropic layer formed using the composition according to any one of

[11] to

[15] , the optically anisotropic layer has an alignment pattern, The optical element, wherein the alignment pattern is a liquid crystal alignment pattern in which the direction of the optical axis derived from the compound contained in the composition is continuously rotated and changed along at least one direction in the plane. 〔19〕 A light guide element comprising the optical element according to

[18] and a light guide plate. The present invention relates to the above items [1] to

[19] . However, other items (for example, the following items) are also included below. <1> ~ <18> It also describes:

[0007] <1> A compound represented by the following general formula (I):

[0008] [ka]

[0009] In general formula (I), P 1 and P 2 each independently represents a hydrogen atom, —CN, —NCS, or a polymerizable group. Sp 1 and Sp 2 each independently represents a single bond or a divalent linking group, provided that Sp 1 and Sp 2 does not represent a divalent linking group having a group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. However, Sp 1 -P 1 and Sp 2 -P 2 However, neither of them is a methyl group. Z 1-O-, -S-, -CHRCHR-, -OCHR-, -CHRO-, -CO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO R represents -, -SO2-CHRCHR-SO2-, -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=NN=CR-, -CF=CF- or -C≡C-. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When multiple Rs are present, the multiple Rs may be the same or different. Multiple Zs present 1 may be the same or different. However, two or more Z 1 represents -C≡C-. -Z in the above general formula (I) 1 -A 2 -Z 1 -A in 2 Two Z's bonded to do not represent -C≡C-. A 1 and A 2 each independently represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, or an aliphatic hydrocarbon ring group, each of which may have a substituent L, or a group formed by linking two groups selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group, each of which may have a substituent L. However, A connected with a triple bond 1 and A 2 At least one of the A's represents a group represented by the following general formula (A-1) or (A-2). 2may be the same or different.

[0010] [ka]

[0011] In general formulas (A-1) to (A-2), W 1 ~W 14 are each independently, CR 1 or N, R 1 represents a hydrogen atom or a substituent L. * indicates the bond position. The substituent L 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, an aldehyde group, or a polymerizable group. However, when the above group has -CH2-, at least one of the -CH2- contained in the above group may be replaced by -O-, -CO-, -CH=CH-, or -C≡C-. In addition, when the above group has a hydrogen atom, at least one of the hydrogen atoms contained in the above group may be substituted with at least one selected from the group consisting of a fluorine atom and a polymerizable group. n represents an integer of 3 to 7.

[0012] <2> In the above general formula (I), n represents 3. <1> The compound described in <3> P in the above general formula (I) 1 and P 2 At least one of represents a polymerizable group, <1> or <2> The compound described in

[0013] <4> A in the above general formula (I) 1 and A 2 each independently represents a group represented by the above general formula (A-1), a group represented by the above general formula (A-2), or a group represented by the following general formula (A-3): <1> ~ <3> The compound according to any one of claims 1 to 10.

[0014] [ka]

[0015] In general formula (A-3), W 15 ~W 18 are each independently, CR 1 or N, R 1 represents a hydrogen atom or a substituent L. * indicates the bond position.

[0016] <5> A in the above general formula (I) 1 and A 2 at least one of which has a substituent L; <1> ~ <4> The compound according to any one of claims 1 to 10. <6> Z in the above general formula (I) 1 represents -CH2CH2-, -OCH2-, -CH2O-, or -C≡C-; <1> ~ <5> The compound according to any one of claims 1 to 10. <7> In the above general formula (I), A linked to the triple bond 1 and A 2 At least one of them represents a group represented by the above general formula (A-2). <1> ~ <6> The compound according to any one of claims 1 to 10.

[0017] <8> Sp in the above general formula (I) 1 represents a group represented by the following general formula (II), Sp 2 represents a group represented by the following general formula (III): <1> ~ <7> 1. The compound according to any one of claims 1 to 9.

[0018] [ka]

[0019] In the general formula (II) and the general formula (III), W 21 and W 22 each independently represents an alkylene group having 1 to 15 carbon atoms, and one or more methylene groups contained in the alkylene group may each independently be replaced by -O-, -S-, or -C(=O)-. * indicates Sp 1 or Sp 2 A directly connected to 1 or A 2 ** indicates the bonding position of P 1 or P 2 represents the bonding position with

[0020] <9> having liquid crystallinity, <1> ~ <8> The compound according to any one of claims 1 to 10. <10> <1> ~ <9> A composition comprising the compound according to any one of claims 1 to 4. <11> Further, a polymerization initiator is contained. <10> The composition described in <12> Further, chiral agents, <10> or <11> The composition described in

[0021] <13> having liquid crystallinity, <10> ~ <12> The composition according to any one of the preceding claims. <14> For forming an optically anisotropic layer, <10> ~ <13> The composition according to any one of the preceding claims. <15> <10> ~ <13> 1. A cured product obtained by curing the composition according to any one of claims 1 to 9. <16> <10> ~ <13> 1. An optically anisotropic body obtained by curing the composition according to any one of claims 1 to 8.

[0022] <17> <10> ~ <13> an optically anisotropic layer formed using the composition according to any one of the preceding items, the optically anisotropic layer has an alignment pattern, The optical element, wherein the alignment pattern is a liquid crystal alignment pattern in which the direction of the optical axis derived from the compound contained in the composition is continuously rotated and changed along at least one direction in the plane. <18> <17> A light guide element comprising the optical element according to claim 1 and a light guide plate. [Effects of the Invention]

[0023] According to the present invention, it is possible to provide a compound having a high refractive index anisotropy Δn, a composition containing the compound, a cured product, an optically anisotropic body, an optical element, and a light guide element. DETAILED DESCRIPTION OF THE INVENTION

[0024] Hereinafter, embodiments for carrying out the present invention will be described in detail, but the present invention is not limited thereto. In this specification, when a numerical value represents a physical property value, characteristic value, etc., the expression "(numerical value 1) to (numerical value 2)" means "(numerical value 1) or more and (numerical value 2) or less." In addition, in this specification, the expression "(meth)acrylate" means "at least one of acrylate and methacrylate." The same applies to "(meth)acrylic acid," "(meth)acryloyl," "(meth)acrylamide," "(meth)acryloyloxy," etc.

[0025] [Compound represented by general formula (1)] The compound represented by the following general formula (I) will be explained.

[0026] [ka]

[0027] In general formula (I), P 1 and P 2each independently represents a hydrogen atom, —CN, —NCS, or a polymerizable group. Sp 1 and Sp 2 each independently represents a single bond or a divalent linking group, provided that Sp 1 and Sp 2 does not represent a divalent linking group having a group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. However, Sp 1 -P 1 and Sp 2 -P 2 However, neither of them is a methyl group. Z 1 -O-, -S-, -CHRCHR-, -OCHR-, -CHRO-, -CO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO R represents -, -SO2-CHRCHR-SO2-, -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=NN=CR-, -CF=CF- or -C≡C-. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When multiple Rs are present, the multiple Rs may be the same or different. Multiple Zs present 1 may be the same or different. However, two or more Z 1 represents -C≡C-. -ZA in the above general formula (I) 2 A in -Z- 2 Two Z's bonded to do not represent -C≡C-. A 1 and A 2 each independently represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, or an aliphatic hydrocarbon ring group, each of which may have a substituent L, or a group formed by linking two groups selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group, each of which may have a substituent L. However, A connected with a triple bond 1 and A 2 At least one of the A's represents a group represented by the following general formula (A-1) or (A-2). 2 may be the same or different.

[0028] [ka]

[0029] In general formulas (A-1) to (A-2), W 1 ~W 14 are each independently, CR 1 or N, R 1 represents a hydrogen atom or a substituent L. * indicates the bond position. The substituent L 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, an aldehyde group, or a polymerizable group. However, when the above group has -CH2-, at least one of the -CH2- contained in the above group may be replaced with -O-, -CO-, -CH=CH- or -C≡C-. Furthermore, when the above group has a hydrogen atom, at least one of the hydrogen atoms contained in the above group may be replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group. n represents an integer of 3 to 7.

[0030] P 1 and P 2 each independently represents a hydrogen atom, —CN, —NCS, or a polymerizable group. The type of polymerizable group is not particularly limited, and includes known polymerizable groups. From the viewpoint of reactivity, a functional group capable of addition polymerization reaction is preferred, and a polymerizable ethylenically unsaturated group or a ring-polymerizable group is more preferred. Examples of the polymerizable group include a (meth)acryloyloxy group, a vinyl group, a maleimide group, a styryl group, an allyl group, an epoxy group, an oxetane group, and groups containing these groups. In addition, the hydrogen atom in each of the above groups may be substituted with another substituent such as a halogen atom. Specific preferred examples of the polymerizable group include groups represented by the following general formulae (P-1) to (P-19): In the following formulae, * represents a bonding position, Me represents a methyl group, and Et represents an ethyl group. The polymerizable group is preferably a (meth)acryloyloxy group.

[0031] [ka]

[0032] P 1 and P 2 It is preferable that at least one of the groups represents a polymerizable group. This is preferable because it can further improve the durability of the compound represented by general formula (I). Among them, P is preferable because it has better reactivity. 1 and P 2 It is preferred that both of the groups are polymerizable groups.

[0033] Sp 1and Sp 2 each independently represents a single bond or a divalent linking group, provided that Sp 1 and Sp 2 does not represent a divalent linking group having a group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. However, Sp 1 -P 1 and Sp 2 -P 2 However, neither of them is a methyl group.

[0034] Sp 1 and Sp 2 When represents a divalent linking group, the divalent linking group is not particularly limited, but is preferably an alkylene group (preferably an alkylene group having 1 to 20 carbon atoms), an alkenylene group (preferably an alkylene group having 2 to 20 carbon atoms), -O-, -S-, -CO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -N(R1)-, or a divalent linking group formed by combining a plurality of these. R1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. Sp 1 and Sp 2 preferably each independently represents a single bond, an alkylene group having 1 to 10 carbon atoms, -O-, -S-, -CO-, -COO-, -OCO-, or a divalent linking group formed by combining a plurality of these. Sp 1 and Sp 2 more preferably each independently represents a single bond, an alkylene group having 1 to 6 carbon atoms, -S-, or a divalent linking group formed by combining a plurality of these, and even more preferably represents a single bond, an alkylene group having 1 to 4 carbon atoms, -S-, or a divalent linking group formed by combining a plurality of these.

[0035] Sp 1 and Sp 2 does not represent a divalent linking group having a group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. The aromatic hydrocarbon ring group may have a monocyclic structure or a polycyclic structure. The aromatic hydrocarbon group is not particularly limited, but may be a phenylene group. The aromatic heterocyclic group may have a monocyclic structure or a polycyclic structure. The aromatic heterocyclic group is not particularly limited, and examples thereof include a heteroarylene group. Examples of the heteroatom contained in the heteroarylene group include at least one atom selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom. The aliphatic hydrocarbon ring group may have a monocyclic structure or a polycyclic structure. The aliphatic hydrocarbon ring group is not particularly limited, but may include a cycloalkylene group.

[0036] Sp in the above general formula (I) 1 represents a group represented by the following general formula (II), Sp 2 represents a group represented by the following general formula (III): The group represented by the following general formula (II) and the group represented by the following general formula (III) contain a sulfur atom, which is preferable because they can improve the refractive index anisotropy Δn of the compound represented by the above general formula (I).

[0037] [ka]

[0038] In the general formula (II) and the general formula (III), W 21 and W 22 each independently represents an alkylene group having 1 to 15 carbon atoms, and one or more methylene groups contained in the alkylene group may each independently be replaced by -O-, -S-, or -C(=O)-. * indicates Sp 1 or Sp 2 A directly connected to 1 or A 2 ** indicates the bonding position of P 1 or P 2 represents the bonding position with W 21 and W 22The alkylene group having 1 to 15 carbon atoms as the alkylene group may be linear or branched, and is preferably a linear alkylene group having 1 to 10 carbon atoms, and more preferably a linear alkylene group having 1 to 5 carbon atoms.

[0039] Z in the above general formula (I) 1 -O-, -S-, -CHRCHR-, -OCHR-, -CHRO-, -CO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO represents -, -SO2-CHRCHR-SO2-, -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=NN=CR-, -CF=CF-, or -C≡C-. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When multiple Rs are present, the multiple Rs may be the same or different. Multiple Zs 1 may be the same or different. However, two or more Z 1 represents -C≡C-. 2 A in -Z- 2 Two Z's bonded to do not represent -C≡C-.

[0040] Z 1 is preferably —CHRCHR—, —OCHR—, —CHRO—, —COO—, —OCO—, —CO—NH—, —NH—CO—, or —C≡C—, and more preferably —CHRCHR—, —OCHR—, —CHRO—, or —C≡C—. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably 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. Z in the above general formula (I) 1 More preferably, represents -CH2CH2-, -OCH2-, -CH2O-, or -C≡C-. This is preferred because it can improve the light resistance of the compound represented by the general formula (I) above.

[0041] A 1 and A 2 each independently represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, or an aliphatic hydrocarbon ring group, each of which may have a substituent L, or a group formed by linking two groups selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group, each of which may have a substituent L. However, A connected with a triple bond 1 and A 2 At least one of the A's represents a group represented by the following general formula (A-1) or (A-2). 2 may be the same or different.

[0042] [ka]

[0043] In general formulas (A-1) to (A-2), W 1 ~W 14 are each independently, CR 1 or N, R 1 represents a hydrogen atom or a substituent L. * indicates the bond position.

[0044] The aromatic hydrocarbon ring group may have a monocyclic structure or a polycyclic structure. The aromatic hydrocarbon ring group is not particularly limited, but is preferably an arylene group, more preferably an arylene group having 6 to 20 carbon atoms, still more preferably an arylene group having 6 to 10 carbon atoms, and particularly preferably a phenylene group or a naphthyl group. The aromatic heterocyclic group may have a monocyclic structure or a polycyclic structure. The aromatic heterocyclic group is not particularly limited, but is preferably a heteroarylene group, more preferably a heteroarylene group having 3 to 20 carbon atoms, and even more preferably a heteroarylene group having 3 to 10 carbon atoms. The heteroatom contained in the heteroarylene group is preferably at least one selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom.

[0045] The aliphatic hydrocarbon ring group may have a monocyclic structure or a polycyclic structure. An example of the aliphatic hydrocarbon ring group is a cycloalkylene group. The cycloalkylene group is not particularly limited, but is preferably a cycloalkylene group having 3 to 20 carbon atoms, and more preferably a cycloalkylene group having 3 to 10 carbon atoms.

[0046] The aromatic hydrocarbon ring group, aromatic heterocyclic group, and aliphatic hydrocarbon ring group may have a substituent L. The substituent L will be described later. The substituent L may be further substituted with a substituent. The number of substituents L is not particularly limited, and the aromatic hydrocarbon ring group, aromatic heterocyclic group, and aliphatic hydrocarbon ring group may have one substituent L or multiple substituents L.

[0047] As mentioned above, A 1 and A 2 may each independently have a substituent L and may be a group formed by linking two groups selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. The group formed by linking two groups selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group is not particularly limited, and examples thereof include a group represented by the above general formula (A-1). Specific examples thereof include a biphenyl group, -benzene ring-pyridine ring- (i.e., a group formed by linking a benzene ring and a pyridine ring), and the like.

[0048] In general formula (A-1), when a plurality of substituents L are present, the plurality of substituents L may be the same or different. In general formula (A-2), when a plurality of substituents L are present, the plurality of substituents L may be the same or different. As mentioned above, A linked to a triple bond 1 and A 2 At least one of the triple bonds is a group represented by the general formula (A-1) or (A-2). 1 There are multiple triple bonds (-C≡C-) in 2 may be the same or different.

[0049] The substituent L 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, an aldehyde group, or a polymerizable group. However, when the above group as the substituent L has -CH2-, at least one of the -CH2- contained in the above group may be replaced with -O-, -CO-, -CH=CH- or -C≡C-. Furthermore, when the above group has a hydrogen atom, at least one of the hydrogen atoms contained in the above group may be replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group. The polymerizable group may be any of the above P 1 , P 2 The same groups as those described as the polymerizable group as the above can be mentioned, and the preferred ranges are also the same.

[0050] The polymerizable group of the substituent L is the above-mentioned P 1 , P 2 The same groups as those described as the polymerizable group as the above can be mentioned, and the preferred ranges are also the same. The substituent L is preferably 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 hydroxy group, a carboxy group, a cyano group, a nitro group, a trifluoromethyl group, or a halogen atom. The substituent L is more preferably 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. The substituent L is more 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, or a fluoro group.

[0051] A in the above general formula (I) 1 and A 2are preferably each independently a group represented by the above general formula (A-1), a group represented by the above general formula (A-2), or a group represented by the following general formula (A-3), which is preferred because it can improve the light resistance and solubility of the compound represented by the above general formula (I).

[0052] [ka]

[0053] In general formula (A-3), W 15 ~W 18 are each independently, CR 1 or N, R 1 represents a hydrogen atom or a substituent L. In general formula (A-3), when a plurality of substituents L are present, the plurality of substituents L may be the same or different.

[0054] A in the above general formula (I) 1 and A 2 At least one of these preferably has a substituent L. This is preferable because it can improve the solubility of the compound represented by the general formula (I) above. In addition, in the above general formula (I), A linked to the triple bond 1 and A 2 At least one of these preferably represents a group represented by the general formula (A-2) above, which is preferred because it can improve the solubility of the compound represented by the general formula (I) above.

[0055] In general formula (I), n represents an integer of 3 to 7. n preferably represents an integer of 3 to 5, more preferably 3 or 4, and even more preferably 3. This is preferable because it can improve the solubility and refractive index anisotropy Δn of the compound represented by the above general formula (I).

[0056] Specific examples of the compound represented by general formula (I) are shown below, but are not limited to these: In the following structural formula, Me represents a methyl group, Et represents an ethyl group, and t-Bu represents a t-butyl group.

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] [ka]

[0062] [ka]

[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] The compound represented by formula (I) can be synthesized by referring to known methods. Specific examples of the synthesis of the compound represented by formula (I) are shown in the examples below.

[0067] The compound represented by general formula (I) may or may not have liquid crystallinity, but preferably has liquid crystallinity. When the compound represented by general formula (I) has liquid crystallinity, it is preferable that the compound represented by general formula (I) is easily aligned when an optically anisotropic layer is produced from a composition containing the compound represented by general formula (I), and a desired alignment pattern can be easily produced. However, even if the compound represented by general formula (I) itself does not have liquid crystallinity, it can be made into a liquid crystal composition by, for example, mixing it with another compound having liquid crystallinity, and a desired alignment pattern can be created.

[0068] A compound having liquid crystallinity means that the compound has the property of exhibiting an intermediate phase between a crystalline phase (low temperature side) and an isotropic phase (high temperature side) when the temperature is changed. Specific observation methods include observing the compound under a polarizing microscope while heating or cooling it on a hot stage or the like, whereby the optical anisotropy and fluidity derived from the liquid crystal phase can be confirmed.

[0069] The optical element of the present invention, which will be described later, is preferably produced by dissolving a composition containing a compound represented by general formula (I) in a solvent and applying the solution. The concentration of the compound represented by general formula (I) in the solvent at 25°C is preferably 5% by mass or more.

[0070] [Composition containing a compound represented by general formula (I)] A composition containing a compound represented by general formula (I) (hereinafter also referred to as "the composition of the present invention") will be described. The content of the compound represented by general formula (I) in the composition of the present invention is not particularly limited, but is preferably 5 to 100 mass % relative to the total mass of the solid content in the composition, more preferably 20 to 99 mass %, even more preferably 30 to 99 mass %, and particularly preferably 40 to 99 mass %. The solid content refers to the components (non-volatile components) in the composition other than the solvent. Components other than the solvent are considered to be solids even if they are in a liquid state. The composition may contain one compound represented by general formula (I) alone or two or more compounds. When two or more compounds are used, the total content thereof is preferably within the above range.

[0071] The composition of the present invention may or may not have liquid crystallinity, but preferably has liquid crystallinity. When the composition of the present invention has liquid crystallinity, it is preferable that the compounds in the composition are easily aligned when an optically anisotropic layer is prepared from the composition, and a desired alignment pattern can be easily formed.

[0072] The term "a composition has liquid crystallinity" means that the composition has the property of exhibiting an intermediate phase between a crystalline phase (low temperature side) and an isotropic phase (high temperature side) when the temperature is changed. A specific observation method is to observe the composition under a polarizing microscope while heating or cooling it on a hot stage or the like, thereby confirming the optical anisotropy and fluidity derived from the liquid crystal phase.

[0073] The composition of the present invention is preferably a composition for forming an optically anisotropic layer.

[0074] The composition of the present invention may contain other components in addition to the compound represented by general formula (I). The other components will be described below.

[0075] <Other liquid crystal compounds> The composition of the present invention may contain liquid crystal compounds other than the compound represented by general formula (I) (also referred to as "other liquid crystal compounds"). The other liquid crystal compound may be a rod-shaped liquid crystal compound or a discotic liquid crystal compound, but is preferably a rod-shaped liquid crystal compound, and is preferably a liquid crystal compound having a polymerizable group (other polymerizable liquid crystal compound). 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.

[0076] 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 P 1 and P 2 Examples of the polymerizable groups include those exemplified in The liquid crystal compound having a polymerizable group preferably has 1 to 6 polymerizable groups, and more preferably 1 to 3 polymerizable groups. The other liquid crystal compounds preferably have a high refractive index anisotropy Δn, specifically, 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, but it is often 0.60 or less. Furthermore, by using a mixture of the compound represented by general formula (I) and other liquid crystal compounds, the crystallization temperature as a whole can be significantly lowered. Other examples of liquid crystal compounds include those described in Makromol.Chem., Vol. 190, p. 2255 (1989), Advanced Materials, Vol. 5, p. 107 (1993), U.S. Pat. Nos. 4,683,327, 4,983,479, 5,622,648, and 5,770,107, International Publication WO95 / 22586, WO95 / 24455, WO97 / 00600, WO98 / 23580, and WO98 / 52905, JP-A Nos. 1-272551, 1-16616, 1-110469, and 1-80081, and JP-A No. 2001-328973. When the composition of the present invention contains other liquid crystal compounds, the content of the other liquid crystal compounds in the composition is not particularly limited, but is preferably 95 mass % or less, more preferably 1 to 80 mass %, even more preferably 1 to 70 mass %, and particularly preferably 1 to 60 mass %, relative to the total mass of the solid content in the composition. The composition of the present invention may contain one or more other liquid crystal compounds. When two or more compounds are used, the total content thereof is preferably within the above range.

[0077] <Polymerization initiator> The composition of the present invention may contain a polymerization initiator. The polymerization initiator is preferably a photopolymerization initiator capable of initiating a polymerization reaction upon irradiation with ultraviolet light. Examples of photopolymerization initiators include α-carbonyl compounds, acyloin ethers, α-hydrocarbon-substituted aromatic acyloin compounds, polynuclear quinone compounds, phenazine compounds, and oxadiazole compounds. Compounds having an oxime ester structure are also preferred. When the composition of the present invention contains a polymerization initiator, the content of the polymerization initiator in the composition is not particularly limited, but is preferably 0.1 to 20 mass %, more preferably 1 to 8 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 invention 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.

[0078] <Surfactant> The composition of the present invention may contain a surfactant that contributes to the stable or rapid formation of a liquid crystal phase (eg, a nematic phase, a cholesteric phase). Examples of surfactants include fluorine-containing (meth)acrylate polymers, compounds represented by general formulas (X1) to (X3) described in WO2011 / 162291, compounds represented by general formula (I) described in paragraphs 0082 to 0090 of JP-A No. 2014-119605, and compounds described in paragraphs 0020 to 0031 of JP-A No. 2013-47204. Examples of fluorine-containing (meth)acrylate polymers that can be used as surfactants include the polymers described in paragraphs 0018 to 0043 of JP-A No. 2007-272185. When the composition of the present invention contains a surfactant, the content of the surfactant is not particularly limited, but is preferably 0.001 to 10 mass %, more preferably 0.05 to 3 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 invention may contain one surfactant alone or two or more surfactants. When two or more surfactants are used, the total content thereof is preferably within the above range.

[0079] <Chiral Agents> The composition of the present invention may contain a chiral agent. When the composition of the present invention contains a chiral agent, it can form a cholesteric phase. The type of chiral agent is not particularly limited. The chiral agent may be liquid crystalline or non-liquid crystalline. The chiral agent generally contains an asymmetric carbon atom. However, an axially asymmetric compound or a planar asymmetric compound that does not contain an asymmetric carbon atom can also be used as the chiral agent. Examples of the axially asymmetric compound or the planar asymmetric compound include binaphthyl, helicene, paracyclophane, and derivatives thereof. The chiral agent may have a polymerizable group. When the composition of the present invention contains a chiral agent, the content of the chiral agent in the composition is not particularly limited, but is preferably 0.1 to 15 mass %, more preferably 1.0 to 10 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 invention may use one chiral agent alone or two or more chiral agents. When two or more chiral agents are used, the total content thereof is preferably within the above range.

[0080] <Solvent> The composition of the present invention may contain a solvent. The solvent is preferably one that can dissolve each component of the composition of the present invention, and examples thereof include chloroform and methyl ethyl ketone. When the composition of the present invention 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 to 20 mass %, more preferably an amount that makes 1 to 10 mass %. The composition of the present invention 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.

[0081] In addition to the above, the composition of the present invention 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.

[0082] It is also preferable to provide the optically anisotropic layer with a substantially broadband wavelength for the wavelength of incident light by adding a twist component to the composition of the present invention or by laminating different retardation layers. For example, JP 2014-089476 A and the like disclose a method for realizing a broadband patterned λ / 2 plate by laminating two liquid crystal layers with different twist directions in an optically anisotropic layer, and this method can be preferably used in the optical element of the present disclosure.

[0083] [Cured product and optically anisotropic body] The cured product and optically anisotropic medium obtained by curing the composition of the present invention will now be described. The method for curing (polymerizing and curing) the composition of the present invention is not particularly limited, and known methods can be used. For example, an embodiment includes a step X of contacting a predetermined substrate with the composition to form a composition layer on the substrate, and a step Y of subjecting the composition layer to a heat treatment to align the compound represented by general formula (I), followed by a curing treatment. According to this embodiment, the compound represented by general formula (I) can be fixed in an aligned state, and an optically anisotropic body (e.g., an optically anisotropic layer) can be formed.

[0084] The procedures of steps X and Y will be described in detail below.

[0085] Step X is a step of contacting a predetermined substrate with the composition to form a composition layer on the substrate. The type of substrate to be used is not particularly limited, and examples thereof include known substrates (e.g., resin substrates, glass substrates, ceramic substrates, semiconductor substrates, and metal substrates). The method for bringing the substrate into contact with the composition is not particularly limited, and examples thereof include a method in which the composition is applied onto the substrate and a method in which the substrate is immersed in the composition. After the substrate and the composition are brought into contact with each other, a drying treatment may be carried out, if necessary, to remove the solvent from the composition layer on the substrate.

[0086] Step Y is a step of subjecting the composition layer to a heat treatment to align the compound represented by general formula (I), and then subjecting the layer to a curing treatment. 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. The conditions for the heat treatment are not particularly limited, and the optimum conditions are selected depending on the type of the compound represented by general formula (I).

[0087] The method of curing treatment is not particularly limited, and examples thereof include photocuring treatment and heat curing treatment. Among these, photoirradiation treatment is preferred, and ultraviolet irradiation treatment is more preferred. For ultraviolet irradiation, a light source such as an ultraviolet lamp is used.

[0088] 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 should be noted 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 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 preferred that the layer has no fluidity and can stably maintain the fixed orientation without causing any change in the orientation due to an external field or external force, usually within a temperature range of 0 to 50°C, or under more severe conditions, within a temperature range of -30 to 70°C.

[0089] [Optical elements] The optical element of the present invention has an optically anisotropic layer formed using the composition of the present invention, the optically anisotropic layer has an alignment pattern, The orientation pattern is an optical element in which the direction of the optical axis derived from the compound contained in the composition is continuously rotated and changed along at least one direction in the plane. The above-mentioned orientation pattern is preferably an orientation pattern in which the direction of the optical axis derived from the compound represented by general formula (I) is continuously rotated along at least one direction in the plane, or an orientation pattern in which the directions of the optical axes derived from the compound represented by general formula (I) and other liquid crystal compounds are continuously rotated along at least one direction in the plane. The optical element of the present invention has an orientation pattern in which the direction of the optical axis is continuously rotated along at least one direction in the plane, thereby enabling the diffracting of light incident on the optical element. The compound represented by general formula (I) is a compound having a high refractive index anisotropy Δn, and therefore can increase the diffraction efficiency. For the optical element, reference can be made to the descriptions of

[0067] to

[0107] in International Publication No. 2020 / 022496.

[0090] The optical element of the present invention can be used as an optical member for an augmented reality (AR) image projection device or the like.

[0091] [Light guide element] The light guide element of the present invention includes the above optical element and a light guide plate. [Example]

[0092] The present invention will be explained in more detail below with reference to examples and comparative examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. It should be noted that "Example 9" and "Example 10" should be read as "Reference Example 9" and "Reference Example 10".

[0093] The synthesis examples of the compounds A-1 to A-11 used in the examples are shown below.

[0094] [Synthesis of Compounds] <Synthesis Example 1: Synthesis of Compound A-1> Compound A-1 was synthesized according to the following scheme: Compound 1 was synthesized according to European Patent No. 2407502, and Compound 4 was synthesized according to International Publication No. 2019 / 182129. Ac represents an acetyl group, Ms represents a methanesulfonyl group (-SO2CH3), and TMS represents a trimethylsilyl group (-Si(CH3)3). Also, rt represents room temperature.

[0095] [ka]

[0096] (1) Synthesis of Compound 2 Compound 1 (1.10 g, 4.18 mmol) was dissolved in tetrahydrofuran (THF) (5 mL). The resulting solution was cooled to -10 °C, and methanesulfonyl chloride (MsCl) (0.50 g, 4.4 mmol) and triethylamine (0.47 g, 4.6 mmol) were added. The mixture was stirred at room temperature (25 °C) for 6 hours. The resulting solution was cooled in an ice-water bath, and ethyl acetate (10 mL) and water (10 mL) were added. The mixture was then extracted with ethyl acetate. The resulting organic layer was washed sequentially with water and brine and then dried over sodium sulfate. The organic layer was filtered, and the solvent was removed under reduced pressure. The resulting residue was reslurried and purified in hexane to give compound 2 (1.27 g, 3.72 mmol). The yield was 89.0%.

[0097] (2) Synthesis of Compound 3 Compound 2 (1.27 g, 3.72 mmol) and methyl 5-iodosalicylate (1.04 g, 3.72 mmol) were dissolved in dimethylacetamide (DMAc) (10 mL), potassium carbonate (0.62 g, 4.5 mmol) and potassium iodide (0.06 g, 0.4 mmol) were added, and the mixture was stirred at 85 °C for 3 hours. Water (50 mL) was added to the resulting solution, and the precipitate was filtered to obtain compound 3 (1.73 g, 3.31 mmol). The yield was 88.9%.

[0098] (3) Synthesis of Compound 5 Under a nitrogen atmosphere, compound 3 (3.00 g, 5.73 mmol) and compound 4 (1.84 g, 12.0 mmol) were dissolved in dimethylacetamide (DMAc) (30 mL) and triethylamine (5.80 g, 57.3 mmol) was added. After bubbling nitrogen through the resulting solution for 1 hour, Pd(PPh3)4 (331 mg, 0.286 mmol) and CuI (109 mg, 0.572 mmol) were added and the mixture was stirred at 80 °C for 8 hours. Ethyl acetate (30 mL) and 1N hydrochloric acid (50 mL) were added to the resulting solution, and the precipitate was filtered. The resulting solid was dissolved in THF, and MeOH was added for reprecipitation to give compound 5 (1.77 g, 2.92 mmol). The yield was 50.9%.

[0099] (4) Synthesis of Compound A-1 Compound 5 (1.77 g, 2.92 mmol) was dissolved in DMAc (10 mL). The resulting solution was cooled in an ice-water bath, and acryloyl chloride (1.28 g, 14.1 mmol) was added. The mixture was stirred at room temperature for 2 hours. The resulting solution was cooled in an ice-water bath, and ethyl acetate (30 mL) and 1N hydrochloric acid (30 mL) were added. The mixture was then extracted with ethyl acetate. The resulting organic layer was washed sequentially with aqueous sodium bicarbonate and brine, and then dried over magnesium sulfate. The organic layer was filtered, and the solvent was removed under reduced pressure. The resulting residue was purified by flash column chromatography to obtain compound A-1 (1.76 g, 2.46 mmol). The yield was 84.4%. 1 H-NMR (CDCl3): δ=3.01(m, 4H), 3.93(s, 3H), 4.39(m, 4H), 5.26(s, 2H), 5.82(d, 1H), 5.84(d, 1H), 6.12(dd, 2H), 6.38( d, 1H), 6.39(d, 1H), 7.02(d, 1H), 7.22(d, 2H), 7,24(d, 2H), 7.45(d, 2H), 7.46(d, 2H), 7.55-7.62(m, 7H), 7.64(d, 2H)

[0100] <Synthesis Example 2: Synthesis of Compound A-2> Compound A-2 was synthesized according to the following scheme: Compound 6 was synthesized according to International Publication No. 2011 / 050276, and Compound 10 was synthesized according to Chun, J.-H, et al. Org. Biomol. Chem. 11, 6300 (2013). TBSO represents a group in which the hydroxyl group is protected with a tert-butyldimethylsilyl group.

[0101] [ka]

[0102] (1) Synthesis of Compound 7 4-Bromothiophenol (28.0 g, 0.148 mol) and compound 6 (36.5 g, 0.148 mmol) were dissolved in acetonitrile (500 mL), potassium carbonate (40.9 g, 0.296 mol) was added, and the mixture was stirred under reflux for 2 hours. The resulting solution was cooled in an ice-water bath, and ethyl acetate (500 mL) and water (400 mL) were added. The resulting organic layer was then extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography to give compound 7 (52.2 g, 0.150 mol). The yield was 62.4%.

[0103] (2) Synthesis of Compound 8 Under a nitrogen atmosphere, compound 7 (32.0 g, 92.1 mmol) was dissolved in THF (320 mL) and triethylamine (92.8 g, 0.917 mol) was added. After bubbling nitrogen through the resulting solution for 1 hour, trimethylsilylacetylene (10.9 g, 0.110 mol), Pd(PPh3)4 (2.12 g, 1.83 mmol), and CuI (0.35 g, 1.8 mmol) were added and the mixture was stirred under reflux for 4 hours. The resulting solution was filtered and washed sequentially with water, 1N hydrochloric acid, aqueous sodium bicarbonate, and brine. The resulting organic layer was dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure, and the resulting residue was purified by flash column chromatography to give compound 8 (28.4 g, 77.9 mmol). The yield was 84.9%.

[0104] (3) Synthesis of Compound 9 Compound 8 (28.4 g, 77.9 mmol) was dissolved in a mixture of THF (140 mL) and MeOH (140 mL), and potassium carbonate (31.7 g, 0.229 mol) was added. The mixture was stirred at room temperature for 1 hour. Water was added to the resulting solution, followed by extraction with ethyl acetate. The resulting organic layer was washed with brine and then dried over magnesium sulfate. After filtering the organic layer, the solvent was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to give compound 9 (20.5 g, 70.1 mmol). The yield was 91.8%.

[0105] (4) Synthesis of Compound 11 Compound 10 (0.90 g, 3.17 mmol) was dissolved in THF (5 mL). The resulting solution was cooled to -10°C, and methanesulfonyl chloride (0.38 g, 3.3 mmol) and triethylamine (0.35 g, 3.5 mmol) were added. The mixture was stirred at room temperature for 3 hours. The resulting solution was cooled in an ice-water bath, and ethyl acetate (10 mL) and water (10 mL) were added. The mixture was then extracted with ethyl acetate. The resulting organic layer was washed sequentially with water and brine and then dried over sodium sulfate. The organic layer was filtered, and the solvent was removed under reduced pressure. The resulting residue was reslurried and purified in hexane to give compound 11 (1.07 g, 2.96 mmol). The yield was 93.3%.

[0106] (5) Synthesis of Compound 12 Compound 11 (1.00 g, 2.76 mmol) and methyl 5-iodosalicylate (0.77 g, 2.76 mmol) were dissolved in DMAc (10 mL), potassium carbonate (0.46 g, 3.3 mmol) and potassium iodide (0.05 g, 0.3 mmol) were added, and the mixture was stirred at 85 °C for 2 hours. Water (50 mL) was added to the resulting solution, and the precipitate was filtered to obtain compound 12 (1.50 g, 2.76 mmol). The yield was 99.8%.

[0107] (6) Synthesis of Compound 13 Under a nitrogen atmosphere, compound 12 (1.50 g, 2.76 mmol) and compound 9 (1.73 g, 5.79 mmol) were dissolved in dimethylacetamide (DMAc) (15 mL) and triethylamine (2.79 g, 27.6 mmol) was added. After bubbling nitrogen through the resulting solution for 1 hour, Pd(PPh3)2Cl2 (97 mg, 0.14 mmol) and CuI (53 mg, 0.28 mmol) were added and the mixture was stirred at room temperature for 3 hours. The resulting solution was cooled in an ice-water bath, and 1N hydrochloric acid (30 mL) and chloroform (30 mL) were added. The mixture was then extracted with chloroform. The resulting organic layer was washed sequentially with aqueous sodium bicarbonate and brine and then dried over sodium sulfate. The organic layer was filtered, the solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to give compound 13 (1.65 g, 1.89 mmol). The yield was 68.5%.

[0108] (7) Synthesis of Compound 14 Compound 13 (1.62 g, 1.85 mmol) was dissolved in THF (10 mL). The resulting solution was cooled in an ice-water bath, and a THF solution of tetra-n-butylammonium fluoride (TBAF) (1 mol / L, 3.9 mL, 3.9 mmol) was added and stirred at room temperature for 2 hours. The resulting solution was cooled in an ice-water bath, and ethyl acetate (20 mL) and 1N hydrochloric acid (20 mL) were added. The mixture was then extracted with ethyl acetate. The resulting organic layer was washed with brine, and hexane was added. The precipitate was filtered to give compound 14 (1.13 g, 1.75 mmol). The yield was 94.5%.

[0109] (8) Synthesis of Compound A-2 Compound 14 (1.10 g, 1.71 mmol) was dissolved in DMAc (5 mL). The resulting solution was cooled in an ice-water bath, and acryloyl chloride (0.83 g, 9.17 mmol) was added. The mixture was stirred at room temperature for 3 hours. The resulting solution was cooled in an ice-water bath, and ethyl acetate (20 mL), 1N hydrochloric acid (20 mL), and MeOH (20 mL) were added. The precipitate was filtered. The resulting solid was purified by flash column chromatography to obtain compound A-2 (0.96 g, 1.28 mmol). The yield was 74.7%. 1 H-NMR (CDCl3): δ=3.22(t, 2H), 3.24(t, 2H), 3.95(s, 3H), 4.35(t, 2H), 4.36(t , 2H), 5.37(s, 2H), 5.84(d, 1H), 5.85(d, 1H), 6.09(dd, 1H), 6.11(dd, 1H), 6.39 (d, 1H), 6.41(d, 1H), 7.34(d, 2H), 7.37(d, 2H), 7.43(d, 2H), 7.50(d, 2H), 7.56 -7.74(m, 3H), 7.83(d, 1H), 7.86(d, 1H), 7.94(s, 1H), 8.03(d, 1H), 8.05(s, 1H)

[0110] <Synthesis Example 3: Synthesis of Compound A-3> Compound A-3 was obtained in the same manner as in Synthesis Example 2, except that ethyl 5-iodosalicylate synthesized according to Narges, H.-E. et al. Bioorg., Med. Chem. Lett. 17, 6354 (2007) was used instead of methyl 5-iodosalicylate.

[0111] <Synthesis Example 4: Synthesis of Compound A-4> Compound A-4 was obtained according to the same procedure as in Synthesis Example 2, except that 4-iodo-2,6-dimethylphenol was used instead of methyl 5-iodosalicylate.

[0112] <Synthesis Example 5: Synthesis of Compound A-5> Compound A-5 was obtained in the same manner as in Synthesis Example 2, except that 4-iodobenzyl alcohol was used instead of compound 10, and methyl 7-bromo-3-hydroxy-2-naphthoate synthesized according to T. Aoyama, Chem. Pharm. Bull. 33, 1458 (1985) was used instead of methyl 5-iodosalicylate.

[0113] <Synthesis Example 6: Synthesis of Compound A-6> Compound A-6 was obtained in the same manner as in Synthesis Example 2, except that Compound 1 was used instead of Compound 10.

[0114] <Synthesis Example 7: Synthesis of Compound A-7> Compound A-6 was obtained according to the same procedure as in Synthesis Example 1, except that acetic anhydride was used instead of acryloyl chloride.

[0115] <Synthesis Example 8: Synthesis of Compound A-8> Compound A-8 was obtained according to the same procedure as in Synthesis Example 2, except that 4-iodophenol was used instead of methyl 5-iodosalicylate.

[0116] <Synthesis Example 9: Synthesis of Compound A-9> Compound A-9 was obtained in the same manner as in Synthesis Example 1, except that compound 10 was used instead of compound 1 and compound 15 synthesized according to WO 2018 / 034216 was used instead of compound 4.

[0117] [ka]

[0118] <Synthesis Example 10: Synthesis of Compound A-10> Compound A-10 was obtained in the same manner as in Synthesis Example 2, except that compound 16, which was obtained by esterifying methyl 5-iodosalicylate with 6-bromo-2-naphthoic acid, was used instead of compound 12.

[0119] [ka]

[0120] <Synthesis Example 11: Synthesis of Compound A-11> Compound A-11 was obtained in the same manner as in Synthesis Example 1, except that Compound 10 was used instead of Compound 1.

[0121] Comparative Example 1: Synthesis of Compound B-1 According to Patent Document 3, Compound B-1 was obtained as a comparative compound. Comparative Example 2: Synthesis of Compound B-2 According to Patent Document 2, Compound B-2 was obtained as a comparative compound.

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] [Examples 1 to 11, Comparative Examples 1 and 2] [evaluation] The above-mentioned compounds A-1 to A-11 and compounds B-1 and B-2 were used to carry out the evaluations described below. In Examples 1 to 11 and Comparative Examples 1 and 2, the compounds shown in Table 1 were used.

[0126] <Liquid crystallinity evaluation> Each compound (compounds A-1 to A-11 and compounds B-1 to B-2) was heated on a hot stage and observed under a polarizing microscope to measure the phase transition temperature and evaluate the presence or absence of liquid crystallinity. Cases with liquid crystallinity were evaluated as A, and cases without liquid crystallinity were evaluated as B. The results are shown in Table 1. Compound A-8 had a melting point of 200°C or higher and underwent a polymerization reaction during heating, so its liquid crystallinity could not be evaluated.

[0127] <Δn (refractive index anisotropy) measurement> The Δn of each compound (compounds A-1 to A-11 and compounds B-1 to B-2) to be measured was measured using a wedge-shaped liquid crystal cell as described on page 202 of Liquid Crystal Handbook (edited by the Liquid Crystal Handbook Editorial Committee, published by Maruzen Co., Ltd., 2000). Δn was measured at a wavelength of 550 nm at 30°C or at the lower limit temperature of the nematic phase +0 to 10°C. For compounds that easily crystallize or lack liquid crystallinity, evaluation was performed using a mixture with another liquid crystal compound, and Δn was estimated from the extrapolated value. The other liquid crystal compound used was L-1-1 below. The mixture was mixed so that the target compound / L-1-1 = 1 / 2 (mass ratio). When Δn was 0.40 or more, it was evaluated as A, when Δn was 0.35 or more and less than 0.40, it was evaluated as B, when Δn was 0.30 or more and less than 0.35, it was evaluated as C, and when it was less than 0.30, it was evaluated as D. The results are shown in Table 1.

[0128] [ka]

[0129] <Solubility evaluation> The solubility of each compound (compounds A-1 to A-11, and compounds B-1 to B-2) in cyclopentanone was evaluated. After preparing a solution in which the compound was dissolved by ultrasonication or heating, it was observed at room temperature (25°C) whether the compound precipitated. Solutions were prepared at various concentrations for each compound, and the concentration at which the compound precipitated was defined as the precipitation concentration. When the precipitation concentration was 5% by mass or more, the solubility was evaluated as A, and when the precipitation concentration was less than 5% by mass, the solubility was evaluated as B. The results are shown in Table 1.

[0130] <Lightfastness / durability evaluation> As shown below, the light resistance and durability of optically anisotropic layers prepared using compositions containing compounds A-1 to A-11, and compounds B-1 and B-2 were evaluated. (Preparation of optically anisotropic layer for light resistance / durability test) A coating solution having the following composition was prepared and spin-coated onto a rubbed glass substrate with an alignment film. Each composition was applied to a hot plate heated to a temperature at which it exhibited a nematic phase, and then irradiated with 300 mJ / cm 2 through a filter that cuts off light of 350 nm or less. 2 The film was then irradiated with ultraviolet light for 100 seconds to prepare an optically anisotropic layer for light resistance / durability testing. ---------------------------------------------------------------------------------- Coating liquid composition ---------------------------------------------------------------------------------- 25 parts by weight of the compound shown in Table 1 below 75 parts by weight of the following polymerizable liquid crystal compound L-1 Polymerization initiator (BASF, Irgacure® 907) 2 parts by mass 0.1 parts by weight of the following leveling agent T-1 Chloroform 1940 parts by mass ----------------------------------------------------------------------------------

[0131] The polymerizable liquid crystal compound L-1 is a mixture containing the following L-1-1 / L-1-2 / L-1-3 in a mass ratio of 84 / 14 / 2. [ka]

[0132] The leveling agent T-1 is a compound having the following structure: [ka]

[0133] (Lightfastness evaluation) The prepared optically anisotropic layer for light resistance / durability testing was irradiated with light using a Super Xenon Weather Meter SX75 manufactured by Suga Test Instruments Co., Ltd. A light resistance test was performed by irradiating the layer with 5 million lx of light for 50 hours under oxygen-blocking conditions using a KU-1000100 UV cut filter manufactured by King Manufacturing Co., Ltd. The temperature of the specimen (temperature inside the test apparatus) was set to 63°C. The relative humidity inside the test apparatus was set to 50%RH. The Re of the optically anisotropic layer was measured before and after the light resistance test, and when the Re change rate shown below was less than 10%, the light resistance was rated as A, and when the Re change rate was 10% or more, the light resistance was rated as B. The smaller the Re change rate, the better the light resistance. The results are shown in Table 1. Here, Re is the in-plane retardation. Re change rate (%) = [100 × {|(Re after test) - (Re before test)|} / (Re before test)] Re was measured using an Axoscan manufactured by Axometrix at a wavelength of 550 nm, and the measurement temperature was room temperature.

[0134] (Durability evaluation) The optically anisotropic layer thus produced was subjected to a humidity and heat durability test at 100°C and 95% humidity for 136 hours. The rate of change in Re before and after the durability test was evaluated, and durability was rated A when the rate of change in Re was less than 10%, and B when the rate of change in Re was 10% or more. The smaller the rate of change in Re, the better the durability. The results are shown in Table 1.

[0135] [Table 1]

[0136] From the results shown in Table 1 above, it was found that the compounds represented by general formula (I) have high refractive index anisotropy Δn (Examples 1 to 11). In addition, it was found that the compound represented by general formula (I) has high solubility. It has been found that an optically anisotropic layer obtained by curing a liquid crystal composition containing a compound represented by general formula (I) has high durability and high light resistance. On the other hand, it was found that the refractive index anisotropy Δn of the comparative compounds that are not compounds represented by general formula (I) was lower than that of the compound represented by general formula (I) (Comparative Examples 1 and 2).

[0137] [Example 12] As Example 12, an optical element was produced using compound A-3 as shown below.

[0138] [Fabrication of Optical Elements] <Support and Saponification Treatment of Support> A commercially available triacetyl cellulose film (Z-TAC, manufactured by Fujifilm Corporation) was prepared as a support. The support was passed through a dielectric heating roll at a temperature of 60°C to raise the surface temperature of the support to 40°C. Then, the alkaline solution described below was applied to one side of the support using a bar coater at a rate of 14 mL (liter) / m 2 The support was heated to 110° C. and then transported under a steam-type far-infrared heater (manufactured by Noritake Company Limited) for 10 seconds. Next, using the same bar coater, 3 mL / m of pure water was applied to the alkaline solution-coated surface of the support. 2 The substrate was then washed with water using a fountain coater and then dried using an air knife three times, and then transported through a drying zone at 70°C for 10 seconds to dry the substrate, thereby subjecting the surface of the substrate to alkaline saponification treatment.

[0139] ---------------------------------------------------------------------------------- alkaline solution ---------------------------------------------------------------------------------- 4.70 parts by mass of potassium hydroxide ·Water 15.80 parts by mass Isopropyl alcohol 63.70 parts by weight Surfactant SF-1: C 14 H 29 O(CH2CH2O)2OH 1.0 parts by mass Propylene glycol 14.8 parts by mass ----------------------------------------------------------------------------------

[0140] <Formation of undercoat layer> The following coating solution for forming an undercoat layer was continuously applied to the alkaline saponified surface of the support using a #8 wire bar. The support on which the coating film was formed was dried with hot air at 60°C for 60 seconds and then with hot air at 100°C for 120 seconds to form an undercoat layer.

[0141] ---------------------------------------------------------------------------------- Coating liquid for forming undercoat layer ---------------------------------------------------------------------------------- 2.40 parts by mass of the following modified polyvinyl alcohol Isopropyl alcohol 1.60 parts by weight Methanol 36.00 parts by mass ·Water 60.00 parts by mass ----------------------------------------------------------------------------------

[0142] Modified polyvinyl alcohol (the ratio of repeating units in the following structural formula is the mass ratio.)

[0143] [ka]

[0144] <Formation of alignment film> The following coating solution for forming an alignment film was continuously applied onto the support on which the undercoat layer had been formed using a wire bar #2. The support on which the coating film of the coating solution for forming an alignment film had been formed was dried on a hot plate at 60°C for 60 seconds to form an alignment film.

[0145] ---------------------------------------------------------------------------------- Coating liquid for forming alignment film ---------------------------------------------------------------------------------- ·Photoalignment material 1.00 parts by mass ·Water 16.00 parts by mass Butoxyethanol 42.00 parts by mass Propylene glycol monomethyl ether 42.00 parts by mass ----------------------------------------------------------------------------------

[0146] Photo alignment material D [ka]

[0147] <Exposing alignment film> The exposure film was exposed using the exposure apparatus shown in FIG. 5 of WO 2020 / 22496 to form an alignment film P-1 having an alignment pattern. The exposure device used was a laser that emitted laser light with a wavelength of 325 nm. The exposure dose by the interference light was 2000 mJ / cm. 2 The period of the alignment pattern formed by the interference of the two laser beams (the length required for the optical axis of the liquid crystal compound to rotate 180°) was controlled by changing the crossing angle (crossing angle β) of the two beams.

[0148] <Formation of Optically Anisotropic Layer> The following composition E-1 was prepared as a composition for forming an optically anisotropic layer.

[0149] ---------------------------------------------------------------------------------- Composition E-1 ---------------------------------------------------------------------------------- ·Compound A-3 50.00 parts by mass 50.00 parts by mass of the following polymerizable liquid crystal compound L-2 Polymerization initiator (BASF, Irgacure® 907) 3.00 parts by mass 0.08 parts by mass of the above leveling agent T-1 Methyl ethyl ketone 927.7 parts by mass ----------------------------------------------------------------------------------

[0150] Polymerizable liquid crystal compound L-2 [ka]

[0151] The optically anisotropic layer was formed by applying composition E-1 in multiple layers onto the alignment film P-1. Multilayer application refers to the process of first applying composition E-1 as a first layer onto the alignment film, heating, cooling, and then UV-curing to form a liquid crystal fixation layer, and then repeatedly applying layers from the second layer onwards to the liquid crystal fixation layer, heating, cooling, and UV-curing in the same manner. By applying multiple layers, the alignment direction of the alignment film is reflected from the bottom surface (the surface facing alignment film P-1) to the top surface of the liquid crystal layer, even when the liquid crystal layer is thick.

[0152] First, the first layer was formed by applying the above composition E-1 onto the alignment film P-1, heating the coating to 80°C on a hot plate, then cooling to 50°C, and then irradiating the coating with ultraviolet light of 365 nm wavelength at 300 mJ / cm using a high-pressure mercury lamp in a nitrogen atmosphere. 2 The alignment of the liquid crystal compound was fixed by irradiating the coating film with an irradiation amount of 10 ...

[0153] The second and subsequent layers were coated on top of the liquid crystal layer, heated and cooled under the same conditions as above, and then cured with ultraviolet light to form a liquid crystal immobilization layer (cured layer). In this way, the coating was repeated until the in-plane retardation (Re) reached 325 nm, forming an optically anisotropic layer, and optical element G-1 was produced.

[0154] The optically anisotropic layer of this example was confirmed using a polarizing microscope to have a periodic alignment surface as shown in Figure 3 of WO 2020 / 22496. In the liquid crystal alignment pattern of this optically anisotropic layer, the period Λ, in which the optical axis derived from liquid crystal compound A-3 rotates 180°, was 1.0 μm. The period Λ was determined by measuring the period of the light-dark pattern observed under crossed Nicol conditions using a polarizing microscope.

[0155] <Measurement of diffraction efficiency> An evaluation optical system was prepared, arranging the evaluation light source, polarizer, quarter-wave plate, optical element G-1, and screen in that order. A laser pointer with a wavelength of 650 nm was used as the evaluation light source, and a Thorlab SAQWP05M-700 quarter-wave plate was used as the quarter-wave plate. The slow axis of the quarter-wave plate was positioned at a 45° angle to the absorption axis of the polarizer. Optical element G-1 was also positioned with its support surface facing the light source. When light from the evaluation light source was transmitted through a polarizer and a quarter-wave plate and incident on optical element G-1 perpendicular to the film surface, some of the light that had transmitted through the optical element was diffracted, and multiple bright spots were visible on the screen. The intensity of each diffracted light and the zero-order light corresponding to a bright spot on the screen was measured with a power meter, and the diffraction efficiency was calculated using the following formula. Diffraction efficiency = (1st-order light intensity) / (0th-order light intensity + diffracted light intensity other than 1st order) The diffraction efficiency obtained was as high as 99% or more.

[0156] <Liquid Crystallinity of Composition> When composition E-1 was dried to volatilize the solvent (methyl ethyl ketone), it was confirmed that the composition exhibited liquid crystallinity.

[0157] [Example 13] As Example 13, a light guide element was produced using a composition containing Compound A-3 and a chiral agent, as shown below.

[0158] The following composition E-2 was prepared as a composition for forming a cholesteric liquid crystal layer as shown in Figure 6 of WO 2020 / 22496. In the structural formula of the following chiral agent Ch-2, Bu represents an n-butyl group. ---------------------------------------------------------------------------------- Composition E-2 ---------------------------------------------------------------------------------- ·Liquid crystal compound A-3 50.00 parts by mass 50.00 parts by mass of the polymerizable liquid crystal compound L-2 3.00 parts by mass of the following polymerization initiator PI-1 4.40 parts by mass of the following chiral agent Ch-1 1.00 parts by mass of the following chiral agent Ch-2 Methyl ethyl ketone 201.31 parts by mass ----------------------------------------------------------------------------------

[0159] Initiator PI-1 [ka]

[0160] Chiral Agent Ch-1 [ka]

[0161] Chiral Agents Ch-2 [ka]

[0162] An alignment film P-1 was prepared in the same manner as in Example 12 above, <Preparation of support and saponification treatment of support>, <Formation of undercoat layer>, <Formation of alignment film> and <Exposure of alignment film>. A cholesteric liquid crystal layer was formed by coating the above composition E-2 on the alignment film P-1 in multiple layers until the film thickness reached 3.5 μm. "Multi-layer coating" here refers to first coating the first layer of liquid crystal composition on the alignment film, heating it, and then curing it with UV light to form a liquid crystal fixation layer. Then, subsequent layers are coated on top of the liquid crystal fixation layer, and the process of heating and UV curing is repeated. By forming the layer using multiple layers, the alignment direction of the alignment film is reflected from the bottom to the top of the liquid crystal layer, even when the total thickness of the liquid crystal layer is large. Composition E-2 was applied to the alignment film P-1 as the first optically anisotropic layer using a spin coater at 1000 rpm. The coating was heated on a hot plate at 80°C for 3 minutes, and then further heated at 50°C under a nitrogen atmosphere with ultraviolet light of 365 nm wavelength at 300 mJ / cm using a high-pressure mercury lamp. 2 The coating film was irradiated with an irradiation dose of 1000 .mu.m to fix the alignment of the liquid crystal compound. The second and subsequent layers were applied on top of this liquid crystal layer, and heated and cured with ultraviolet light under the same conditions as above to form a cholesteric liquid crystal layer. The formed cholesteric liquid crystal layer was attached to a light guide plate (glass with a refractive index of 1.80 and a thickness of 0.50 mm) to prepare a light guide element. When 532 nm light was incident on the fabricated light guide element from the light guide plate side in the normal direction, it was confirmed that the incident light was reflected by the cholesteric liquid crystal layer in a direction other than the regular reflection direction at a critical angle and was guided within the light guide plate. In this way, a light guide element could be produced using a composition containing the compound represented by general formula (I) and a chiral agent.

[0163] <Liquid Crystallinity of Composition> Composition E-2 was dried to volatilize the solvent (methyl ethyl ketone), and it was confirmed that the composition exhibited liquid crystallinity. [Industrial Applicability]

[0164] According to the present invention, it is possible to provide a compound having a high refractive index anisotropy Δn, a composition containing the compound, a cured product, an optically anisotropic body, an optical element, and a light guide element.

[0165] Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention. This application is based on a Japanese patent application (Patent Application No. 2021-104475) filed on June 23, 2021, the contents of which are incorporated herein by reference.

Claims

1. A compound represented by the following general formula (I): 【Chemistry 1】 In general formula (I), P １ and P ２ each independently represents a hydrogen atom, —CN, —NCS, or a polymerizable group represented by any one of the following general formulae (P-1) to (P-19), and at least one of P 1 and P 2 represents a polymerizable group represented by any one of the following general formulae (P-1) to (P-19): In the following general formulae (P-1) to (P-19), * represents a bonding position, Me represents a methyl group, and Et represents an ethyl group. 【Chemistry 2】 Sp １ and Sp ２ each independently represents a single bond, an alkylene group, an alkenylene group, -O-, -S-, -CO-, -SO-, -SO 2 -, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -N(R 1 )-, or a divalent linking group formed by combining a plurality of these. R 1 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. However, Sp １ and Sp ２ does not represent a divalent linking group having a group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. However, Sp １ -P １ and Sp ２ -P ２ However, neither of them is a methyl group. Z １ is -O-, -S-, -CHRCHR-, -OCHR-, -CHRO-, -CO-, -SO-, -SO ２ -, -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 -C≡C-. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When multiple Rs are present, the multiple Rs may be the same or different. Multiple Zs present １ may be the same or different. However, two or more Z １ represents -C≡C-. -Z in the general formula (I) １ -A ２ -Z １ A in - ２ Two Z's bonded to do not represent -C≡C-. A １ and A ２ each independently represents an aromatic hydrocarbon ring group or an aliphatic hydrocarbon ring group, each of which may have a substituent L, or a group formed by linking two groups selected from the group consisting of aromatic hydrocarbon ring groups and aliphatic hydrocarbon ring groups, each of which may have a substituent L. However, A connected to a triple bond １ and A ２ At least one of the A's represents a group represented by the following general formula (A-1) or (A-2). ２ may be the same or different. 【Transformation 3】 In general formulas (A-1) to (A-2), W １ ~W １４ each independently represents CR 1 , and R １ represents a hydrogen atom or a substituent L. * indicates the bond position. The substituent L 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 an aldehyde group, provided that the above groups are not -CH ２ When the group has -, -CH contained in the above group ２ At least one of the - may be replaced by -O-, -CO-, -CH=CH- or -C≡C-. When the above group has a hydrogen atom, at least one of the hydrogen atoms contained in the above group may be replaced by a fluorine atom. n represents an integer of 3 to 7.

2. The compound according to claim 1 , wherein n in the general formula (I) represents 3.

3. The compound according to claim 1, wherein both P 1 and P 2 in general formula (I) represent a polymerizable group represented by any one of general formulas (P-1) to (P-19).

4. Z 1 in the general formula (I) is -O-, -S-, -CHRCHR-, -OCHR-, -CHRO-, -CO-, -SO-, -SO 2 -, -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 3. The compound according to claim 1, wherein R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When a plurality of Rs are present, the plurality of Rs may be the same or different.

5. A in the general formula (I) １ and A ２ each independently represent a group represented by general formula (A-1), a group represented by general formula (A-2), or a group represented by general formula (A-3): 【Chemistry 4】 In general formula (A-3), W １５ ~W １８ each independently represents CR 1 , and R １ represents a hydrogen atom or a substituent L. * indicates the bond position.

6. A in the general formula (I) １ and A ２ The compound according to claim 1 or 2, wherein at least one of the following has a substituent L:

7. Z in the general formula (I) １ is -CH ２ CH ２ -, -OCH ２ -, -CH ２ The compound according to claim 1 or 2, wherein the group represents O— or —C≡C—.

8. In the general formula (I), A linked to a triple bond １ and A ２ The compound according to claim 1 or 2, wherein at least one of the following represents a group represented by general formula (A-2):

9. Sp in the general formula (I) １ represents a group represented by the following general formula (II), Sp ２ The compound according to claim 1 or 2, wherein represents a group represented by the following general formula (III): 【Transformation 5】 In general formula (II) and general formula (III), W ２１ and W ２２ each independently represents an alkylene group having 1 to 15 carbon atoms, and one or more methylene groups contained in the alkylene group may each independently be replaced by —O—, —S—, or —C(═O)—. * indicates Sp １ or Sp ２ A directly connected to １ or A ２ ** represents the bonding position with P １ or P ２ represents the bonding position with

10. The compound according to claim 1 or 2, which has liquid crystal properties.

11. A composition comprising a compound according to claim 1 or 2.

12. The composition of claim 11 further comprising a polymerization initiator.

13. The composition of claim 11 further comprising a chiral agent.

14. The composition according to claim 11, which has liquid crystal properties.

15. The composition according to claim 11, which is for forming an optically anisotropic layer.

16. A cured product obtained by curing the composition according to claim 11.

17. An optically anisotropic body obtained by curing the composition according to claim 11.

18. An optically anisotropic layer formed using the composition according to claim 11, the optically anisotropic layer has an alignment pattern, An optical element, wherein the alignment pattern is a liquid crystal alignment pattern in which the direction of the optical axis derived from a compound contained in the composition is continuously rotated and changed along at least one direction in the plane.

19. A light guide element comprising the optical element according to claim 18 and a light guide plate.

Images