Compound, Composition, Cured Product, Optical Isomer, Optical Element, and Light Guide Element

Abstract

To provide: a compound with high refractive index anisotropy ▵n; and a composition, a cured product, an optically anisotropic body, an optical element and a light guide element that comprise the compound.SOLUTION: The invention provides: a compound, e.g., represented by a formula (A-2) in the figure; and a composition, a cured product, an optically anisotropic body, an optical element, and a light guide element that comprise a compound represented by the formula (A-2) or the like.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[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 applied to various uses. For example, Patent Document 1 describes that an optical element including an optically anisotropic layer made of a cured product of a composition containing a liquid crystal compound can obtain diffracted light with a large diffraction angle and high diffraction efficiency. Patent Document 1 describes that good diffraction efficiency can be obtained by using a liquid crystal compound having a high refractive index anisotropy Δn (hereinafter also simply referred to as "Δn"). Further, Patent Document 2 describes a liquid crystal compound having a high Δn. Patent Document 2 describes a reflective film formed by curing a composition containing a liquid crystal compound having a high Δn.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0004] As described in Patent Documents 1 and 2, liquid crystal compounds having a high Δn are useful for various applications. Further, a compound having a high Δn can be made into a liquid crystal composition having a high Δn by mixing it with another compound having liquid crystallinity, for example, even if the compound itself does not have liquid crystallinity, and is useful for 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 optical anisotropic body, an optical element, and a light guide element.

Means for Solving the Problems

[0006] The present inventors have intensively studied and found that the above problems can be solved by the following means. [1] A compound represented by the following general formula (I).

Chemical Formula

Chem.

Chem.

[10] Among Z 1 、Z 2 and Z 3 in the general formula (I), each independently represents a single bond, -CHR-, -CHRCHR-, -OCHR-, -CHRO- or -OCHRCHRO-, and the compound according to any one of [1] to [9]. However, Z 2 connected to Sp 3 represents a single bond. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When a plurality of R's are present, they may be the same or different.

[11] The compound represented by the general formula (I) is the compound represented by the following general formula (I-2) or (I-3), and the compound according to [1].

Chem.

Chem.

[12] A composition containing the compound according to any one of [1] to

[11] .

[13] Furthermore, the composition according to

[12] , further containing a polymerization initiator.

[14] Furthermore, the composition according to

[12] or

[13] , further containing a chiral agent.

[15] The composition according to any one of

[12] to

[14] , having liquid crystallinity.

[16] The composition according to any one of

[12] to

[15] , for forming an optically anisotropic layer.

[17] A cured product obtained by curing the composition according to any one of

[12] to

[16] .

[18] An optically anisotropic body obtained by curing the composition according to any one of

[12] to

[16] .

[19] Having an optically anisotropic layer formed using the composition according to any one of

[12] to

[16] , the optically anisotropic layer has an alignment pattern, the alignment pattern is an alignment pattern in which the direction of the optical axis derived from the compound contained in the composition continuously rotates and changes along at least one direction in the plane, and the optical element.

[20] An optical waveguide element including the optical element according to

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

[20] , but other matters are also described in this specification for reference.

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

[0008]

Chemical formula

[0009] In the 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. However, Sp 1 and Sp 2 do not represent a divalent linking group containing at least one group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group and an aliphatic hydrocarbon ring group. Z 1 , Z 2 and Z 3Each independently represents a single bond, -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO2-CHRCHR-SO2-, -CH=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 a plurality of Rs are present, they may be the same or different. Z 1 and Z 2 When a plurality of them are present, they may be the same or different. When a plurality of Zs are present 3 may be the same or different. However, Sp 2 the Z linked to 3 represents a single bond. X 1 and X 2 Each independently represents a single bond or -S-. When a plurality of Xs are present 1 and X 2 may be the same or different. However, when a plurality of Xs are present 1 and a plurality of Xs 2 at least one of them represents -S-. k represents an integer of 2 to 4. m and n each independently represent an integer of 0 to 3. When a plurality of ms are present, they may be the same or different. A 1 、A 2 、A 3 and A4 represents, independently of each other, a group represented by any one of the following general formulas (B-1) to (B-7), or a group formed by linking two or more and three or less groups represented by any one of the following general formulas (B-1) to (B-7). A existing in plural 2 and A 3 may be the same or different from each other. A 1 and A 4 when there are a plurality of each, may be the same or different from each other.

[0010]

Chemical formula

[0011] In general formulas (B-1) to (B-7), W 1 ~W 18 each independently represents CR 1 or N, and R 1 represents a hydrogen atom or the following substituent L. Y 1 ~Y 6 each independently represents NR 2 , O or S, and R 2 represents a hydrogen atom or the following substituent L. G 1 ~G 4 each independently represents CR 3 R 4 , NR 5 , O or S, and R 3 ~R 5 each independently represents a hydrogen atom or the following substituent L. M 1 and M 2 each independently represents CR 6 or N, and R 6 represents a hydrogen atom or the following substituent L. * represents the bonding position. The substituent L is 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 amide group, a cyano group, a nitro group, a halogen atom or a polymerizable group. However, when the above groups described as the substituent L have -CH2-, at least one of -CH2- contained in the above groups replaced by -O-, -CO-, -CH=CH- or -C≡C- is also included in the substituent L. Further, when the above groups described as the substituent L have a hydrogen atom, at least one of the hydrogen atoms contained in the above groups replaced by at least one selected from the group consisting of a fluorine atom and a polymerizable group is also included in the substituent L. <2> The compound according to <1>, wherein n and m in the general formula (I) represent 0. <3> The compound according to <1> or <2>, wherein k in the general formula (I) represents 2. <4> A plurality of Xs present in the general formula (I) 1 and a plurality of Xs present 2 Among them, the compound according to any one of <1> to <3>, wherein at least two of them represent -S-. <5> In the general formula (I), n represents 0, m represents 0 or 1, the m closest to Sp 2 represents 0, the X 1 linked to Sp 1 is made X 1A and the Z 2 linked to Sp 3 and the X 2 linked to it are made X 2A Then, at least one of X 1A and X 2A represents -S-, and X 1AX other than 1 and X 2A X other than 2 represents a single bond, and Z 2 and Z 3 each independently represents a single bond, -O-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -OCHRCHRO-, -SO-CHRCHR-SO-, -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=N-N=CR-, -CF=CF- or -C≡C-, the compound according to <1>. However, Sp 2 Z linked to 3 represents a single bond. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When a plurality of Rs are present, they may be the same or different. <6> P in the general formula (I) above 1 and P 2 at least one of which represents a polymerizable group, the compound according to any one of <1> to <5>. <7> P in the general formula (I) above 1 represents a polymerizable group, n represents 0, and Sp 1 X linked to 1 represents -S-, the compound according to any one of <1> to <6>. <8> A in the general formula (I) above 1 A 2 A 3 and A 4is, independently of each other, a group represented by the general formula (B-1) or (B-2), the compound according to any one of <1> to <7>. However, W in the general formula (B-1) 1 and W 2 do not both represent N, and W 3 and W 4 do not both represent N. Also, W in the general formula (B-2) 5 and W 6 do not both represent N, and W 9 and W 10 do not both represent N. <9> Among A 1 , A 2 , A 3 and A 4 in the general formula (I), at least one has the substituent L, the compound according to any one of <1> to <8>. <10> Z 1 , Z 2 and Z 3 in the general formula (I) each independently represents a single bond, -CHR-, -CHRCHR-, -OCHR-, -CHRO- or -OCHRCHRO-. However, Z 2 linked to Sp 3 represents a single bond. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When a plurality of R's are present, they may be the same or different. <11> The compound represented by the general formula (I) is a compound represented by the following general formula (I-2) or (I-3), the compound according to <1>.

[0012]

Chemical formula

[0013]

Chemical formula

[0014] In general formulas (I-2) and (I-3), T 1 and T 2 each independently represents a hydrogen atom or a methyl group. r represents an integer from 1 to 5. t and v each independently represent 0 or 1. u represents 1 or 2. w represents an integer from 1 to 5. Q 1 ~Q 16 each independently represents a hydrogen atom or the above substituent L. E 1 ~E 6 each independently represents a hydrogen atom or the above substituent L. <12> A compound according to any one of <1> to <11>, having liquid crystallinity. <13> A composition containing a compound according to any one of <1> to <12>. <14> Furthermore, the composition according to <13>, further containing a polymerization initiator. <15> Furthermore, the composition according to <13> or <14>, further containing a chiral agent. <16> A composition according to any one of <13> to <15>, having liquid crystallinity. <17> A composition according to any one of <13> to <16>, for forming an optically anisotropic layer. <18> A cured product obtained by curing a composition according to any one of <13> to <16>. <19> An optically anisotropic body obtained by curing a composition according to any one of <13> to <16>. <20> Having an optically anisotropic layer formed using a composition according to any one of <13> to <16>, the above optically anisotropic layer has an alignment pattern, The alignment pattern is an optical element that is an alignment pattern in which the directions of the optical axes derived from the compounds contained in the composition continuously rotate and change along at least one direction in the plane. <21> A light guide element including the optical element according to <20> and a light guide plate.

Advantages of the Invention

[0015] 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 optical anisotropic body, an optical element, and a light guide element.

Modes for Carrying Out the Invention

[0016] Hereinafter, the modes 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, a characteristic value, etc., the description “(numerical value 1) to (numerical value 2)” represents the meaning of “(numerical value 1) or more and (numerical value 2) or less”. Further, in this specification, the description “(meth)acrylate” represents the meaning of “at least one of acrylate and methacrylate”. The same applies to “(meth)acrylic acid”, “(meth)acryloyl”, “(meth)acrylamide”, “(meth)acryloyloxy”, etc.

[0017] 〔Compound Represented by General Formula (I)〕 The compound represented by the compound represented by the following general formula (I) will be described.

[0018]

Chemical Formula

[0019] 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. However, Sp1 and Sp 2 does not represent a divalent linking group containing at least one group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. Z 1 Z 2 and Z 3 each independently represents a single bond, -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO2-CHRCHR-SO2-, -CH=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 a plurality of R's are present, they may be the same or different. Z 1 and Z 2 when a plurality of each are present, they may be the same or different. When a plurality of Z's 3 are present, they may be the same or different. However, Z 2 linked to Sp 3 represents a single bond. X 1 and X 2 each independently represents a single bond or -S-. When a plurality of X's 1 and X 2 are present, they may be the same or different. However, when a plurality of X's 1 and a plurality of X's 2 are present, at least one of them represents -S-. k represents an integer from 2 to 4. m and n each independently represent an integer from 0 to 3. Multiple m's may be the same or different. A 1 , A 2 , A 3 and A 4 each independently represent a group represented by any one of the following general formulas (B-1) to (B-7), or a group formed by linking two or more and three or less groups represented by any one of the following general formulas (B-1) to (B-7). Multiple A's 2 and A 3 may be the same or different. A 1 and A 4 may be the same or different when there are multiple of each.

[0020] [Chemical formula]

[0021] In general formulas (B-1) to (B-7), W 1 ~W 18 each independently represents CR 1 or N, and R 1 represents a hydrogen atom or the following substituent L. Y 1 ~Y 6 each independently represents NR 2 , O or S, and R 2 represents a hydrogen atom or the following substituent L. G 1 ~G 4 each independently represents CR 3 R 4 , NR 5 , O or S, and R 3 ~R 5 each independently represents a hydrogen atom or the following substituent L. M 1 and M 2 each independently represents CR 6 or N, and R 6 represents a hydrogen atom or the following substituent L. * represents the bonding position. The substituent L is 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 amide group, a cyano group, a nitro group, a halogen atom or a polymerizable group. However, when the above groups described as the substituent L have -CH2-, at least one of -CH2- contained in the above groups is replaced with -O-, -CO-, -CH=CH- or -C≡C-, and the resulting group is also included in the substituent L. Further, when the above groups described as the substituent L have a hydrogen atom, 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, and the resulting group is also included in the substituent L.

[0022] In the general formula (I), n represents an integer of 0 to 3, preferably represents an integer of 0 to 2, more preferably represents 0 or 1, and still more preferably represents 0.

[0023] In the general formula (I), m represents an integer of 0 to 3, preferably represents an integer of 0 to 2, more preferably represents 0 or 1, and still more preferably represents 0.

[0024] It is particularly preferred that n and m in the general formula (I) represent 0. When n and m represent 0, the solubility of the compound represented by the general formula (I) is increased, which is preferable.

[0025] In the general formula (I), k represents an integer of 2 to 4, preferably represents 2 or 3, and more preferably represents 2. When k represents 2, the solubility of the compound represented by the general formula (I) is increased, which is preferable.

[0026] P in general formula (I) 1 and P 2 each independently represents a hydrogen atom, -CN, -NCS or a polymerizable group.

[0027] When producing an optically anisotropic layer from a composition containing a compound represented by general formula (I), the orientation state of the compound represented by general formula (I) can be fixed or the durability of the optically anisotropic layer can be improved. For this reason, 1 and P 2 it is preferable that at least one of them represents a polymerizable group. For the reason that the reactivity is more excellent, 1 and P 2 it is more preferable that both represent polymerizable groups. The polymerizable group is not particularly limited, and examples include known polymerizable groups. From the viewpoint of reactivity, a functional group capable of addition polymerization reaction is preferable, and a polymerizable ethylenically unsaturated group or a ring polymerizable group is more preferable. 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. Note that the hydrogen atom in each of the above groups may be substituted with another substituent such as a halogen atom. Preferable specific examples of the polymerizable group include groups represented by any of the following formulas (P-1) to (P-19). In the following formulas, * represents the bonding position, Me represents a methyl group, and Et represents an ethyl group. The polymerizable group is preferably a (meth)acryloyloxy group.

[0028]

Chemical formula

[0029] Sp in general formula (I) 1 and Sp 2 each independently represents a single bond or a divalent linking group. However, Sp 1 and Sp 2does not represent a divalent linking group containing at least one group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. Sp 1 and Sp 2 When Sp and Sp represent a divalent linking group, the divalent linking group is not particularly limited, but an alkylene group (preferably an alkylene group having 1 to 20 carbon atoms), an alkenylene group (preferably an alkenylene group having 2 to 20 carbon atoms), -O-, -S-, -CO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, or a divalent linking group formed by combining a plurality of these is preferable. Sp 1 and Sp 2 each independently preferably represents a single bond or a divalent linking group formed by combining an alkylene group having 1 to 10 carbon atoms, -O-, -CO-, -COO-, -OCO-, or a plurality of these. Sp 1 and Sp 2 each more preferably independently represents a single bond or an alkylene group having 1 to 6 carbon atoms, and still more preferably represents a single bond or an alkylene group having 1 to 4 carbon atoms.

[0030] In General Formula (I), Z 1 , Z 2 and Z 3is, independently of each other, a single bond, -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SCHR-, -CHRS-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -CF2S-, -SCF2-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO2-CHRCHR-SO2-, -CH=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 a plurality of Rs are present, they may be the same or different. Z 1 and Z 2 , when a plurality of them are present, may be the same or different. When a plurality of Zs are present 3 may be the same or different. However, Sp 2 the Z linked to 3 represents a single bond. Z 1 , Z 2 and Sp 2 the Z linked to 3 other than Z 3 preferably represents a group other than a single bond. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, preferably represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and still more preferably represents a hydrogen atom.

[0031] In general formula (I), X 1 and X 2 each independently represents a single bond or -S-. When a plurality of Xs are present1 and X 2 may be the same or different from each other. However, among a plurality of X 1 and a plurality of X 2 at least one of them represents -S-. By introducing a sulfur atom with a high refractive index, △n of the compound represented by the general formula (I) can be increased. Therefore, among a plurality of X 1 and a plurality of X 2 it is preferable that at least two of them represent -S-.

[0032] Since the compound represented by the general formula (I) can be a compound having liquid crystallinity, n in the general formula (I) represents 0, m represents 0 or 1, and m at the position closest to Sp 2 represents 0, and X 1 linked to Sp 1 is X 1A Sp 2 linked to Z 3 linked to X 2 is X 2A When made into X 1A and X 2A at least one of them represents -S-, and X 1A X other than 1 and X 2A X other than 2 represents a single bond, and Z 2 and Z 3is each independently preferably a single bond, -O-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -OCHRCHRO-, -SO-CHRCHR-SO-, -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=N-N=CR-, -CF=CF- or -C≡C-. However, Sp 2 Z linked to 3 represents a single bond. The definition and preferred range of R are as described above. Z 2 and Sp 2 Z linked to 3 Z other than 3 preferably represents a group other than a single bond.

[0033] When n and m in the general formula (I) represent 0, and X 1 linked to Sp 1 is X 1A and X 2 linked to Z 3 linked to X 2 is X 2A Then, at least one of X 1A and X 2A represents -S-, and X 1A X other than 1 and X 2A X other than 2 represents a single bond, and Z 3is more preferably -O-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO2-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SO-CHR-, -CHR-SO-, -SO2-CHR-, -CHR-SO2-, -CF2O-, -OCF2-, -OCHRCHRO-, -SO-CHRCHR-SO-, -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=N-N=CR-, -CF=CF- or -C≡C-. However, Sp 2 Z linked to 3 represents a single bond. The definition and preferred range of R are as described above. Sp 2 Z linked to 3 Z other than 3 preferably represents a group other than a single bond.

[0034] Also, P in general formula (I) 1 represents a polymerizable group, n represents 0, and Sp 1 X linked to 1 also preferably represents -S-.

[0035] Z in general formula (I) 1 Z 2 and Z 3 each preferably independently represents a single bond, -CHR-, -CHRCHR-, -OCHR-, -CHRO- or -OCHRCHRO-. However, Sp 2 Z linked to 3 represents a single bond. The definition and preferred range of R are as described above. Z 1 Z 2 and Sp 2 Z linked to 3 Z other than 3 preferably represents a group other than a single bond.

[0036] A in general formula (I) 1 , A 2 , A 3 and A 4 each independently represents a group represented by any one of the following general formulas (B-1) to (B-7), or a group formed by linking two or more and three or less groups represented by any one of the following general formulas (B-1) to (B-7). When there are a plurality of A 2 and A 3 may be the same or different from each other. A 1 and A 4 , when there are a plurality of each, may be the same or different from each other.

[0037]

Chemical formula

[0038] In general formulas (B-1) to (B-7), W 1 ~W 18 each independently represents CR 1 or N, and R 1 represents a hydrogen atom or the following substituent L. Y 1 ~Y 6 each independently represents NR 2 , O or S, and R 2 represents a hydrogen atom or the following substituent L. G 1 ~G 4 each independently represents CR 3 R 4 , NR 5 , O or S, and R 3 ~R 5 each independently represents a hydrogen atom or the following substituent L. M 1 and M 2 each independently represents CR 6 or N, and R 6 represents a hydrogen atom or the following substituent L. * represents the bonding position. The substituent L is 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 amide group, a cyano group, a nitro group, a halogen atom or a polymerizable group. However, when the above group described as the substituent L has -CH2-, at least one of -CH2- contained in the above group replaced by -O-, -CO-, -CH=CH- or -C≡C- is also included in the substituent L. For example, when the above group has two or more -CH2-, one -CH2- may be replaced by -O- and one -CH2- adjacent thereto may be replaced by -CO- to form an ester group (-O-CO-). Further, when the above group described as the substituent L has a hydrogen atom, at least one of the hydrogen atoms contained in the above group replaced by at least one selected from the group consisting of a fluorine atom and a polymerizable group is also included in the substituent L. The above polymerizable group is the same as the polymerizable group when P 1 and P 2 represent a polymerizable group.

[0039] In general formulas (B-1) to (B-7), W 1 to W 18 each independently represents CR 1 or N, and preferably represents CR 1 . When a plurality of R 1 are present in general formulas (B-1) to (B-7), they may be the same or different. Y 1 to Y 6 each independently represents NR 2 , O or S, and preferably represents S. When a plurality of R 2When there are a plurality of them, they may be the same or different. G 1 ~G 4 each independently represents CR 3 R 4 , NR 5 , O or S, and it is preferable that CR 3 R 4 is represented. In general formula (B-7), when there are a plurality of R 3 ~R 5 respectively, they may be the same or different. M 1 and M 2 each independently represents CR 6 or N, and it is preferable that CR 6 is represented. In general formula (B-7), when there are a plurality of R 6 they may be the same or different.

[0040] R 1 ~R 6 each independently represents a hydrogen atom or the aforementioned substituent L. 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 trifluoromethyl group, a hydroxy group, a carboxy group, a cyano group, a nitro 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 still 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 fluorine atom.

[0041] Since the light resistance of the compound represented by the general formula (I) is high, A in the general formula (I) 1 , A 2 , A 3 and A 4 each preferably independently represents a group represented by the above general formula (B-1) or (B-2). Further, when A 1 , A 2 , A 3 and A 4 in the general formula (I) represent a group represented by the above general formula (B-1) or (B-2), it is preferable that W 1 and W 2 in the general formula (B-1) do not both represent N, and it is preferable that W 3 and W 4 in the general formula (B-1) do not both represent N. Further, it is preferable that W 5 and W 6 in the general formula (B-2) do not both represent N, and it is preferable that W 9 and W 10 in the general formula (B-2) do not both represent N.

[0042] A 1 , A 2 , A 3 and A 4 in the general formula (I) may be a group formed by linking two or more and three or less groups represented by any of the above general formulas (B-1) to (B-7). Note that the group formed by linking two or more and three or less groups represented by any of the above general formulas (B-1) to (B-7) may be a group formed by linking groups having the same structure or a group formed by linking groups having different structures. For example, as a group formed by linking two groups represented by the general formula (B-1), a group represented by the following general formula (B-1-2) can be mentioned.

[0043]

Chemical formula

[0044] In the general formula (B-1-2), W 1 to W 4 each independently represents CR 1 or N, and R1 represents a hydrogen atom or the above-mentioned substituent L. When there are a plurality of Ws 1 ~W 4 may be the same or different from each other.

[0045] Due to the high solubility of the compound represented by the general formula (I), A in the general formula (I) 1 , A 2 , A 3 and A 4 Preferably, at least one of them has the above-mentioned substituent L.

[0046] The compound represented by the general formula (I) is preferably a compound represented by the following general formula (I-2) or (I-3).

[0047]

Chemical formula

[0048]

Chemical formula

[0049] In the general formulas (I-2) and (I-3), T 1 and T 2 each independently represents a hydrogen atom or a methyl group. r represents an integer from 1 to 5. t and v each independently represent 0 or 1. u represents 1 or 2. w represents an integer from 1 to 5. Q 1 ~Q 16 each independently represents a hydrogen atom or the above-mentioned substituent L. E 1 ~E 6 each independently represents a hydrogen atom or the above-mentioned substituent L.

[0050] T 1 and T 2 Preferably represent a hydrogen atom. r preferably represents an integer from 1 to 4, more preferably represents an integer from 2 to 4, still more preferably represents 2 or 3, and particularly preferably represents 2. t preferably represents 0. u preferably represents 1. v preferably represents 1. w preferably represents an integer from 1 to 4, more preferably represents an integer from 2 to 4, still more preferably represents 2 or 3, and particularly preferably represents 2. Q 1 ~Q 16 and E 1 ~E 6 each independently represents a hydrogen atom or the above substituent L, and the preferred range of the substituent L is as described above.

[0051] Q in the general formula (I-2) 5 ~Q 12 at least one of them preferably represents the substituent L, and 5 ~Q 12 more preferably one or two of them represent the substituent L. E in the general formula (I-3) 1 ~E 6 and Q 9 ~Q 12 at least one of them preferably represents the substituent L, and 1 ~E 6 and Q 9 ~Q 12 more preferably one or two of them represent the substituent L.

[0052] Specific examples of the compound represented by the general formula (I) are shown below, but are not limited thereto. In the following structural formulas, Me represents a methyl group, Et represents an ethyl group, and t-Bu represents a tert-butyl group.

[0053]

Chemical formula

[0054]

Chemical formula

[0055]

Chem.

[0056]

Chem.

[0057]

Chem.

[0058]

Chem.

[0059]

Chem.

[0060]

Chem.

[0061]

Chem.

[0062]

Chem.

[0063]

Chem.

[0064]

Chem.

[0065] [Chemical]

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

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

[0068] For a compound to have liquid crystallinity means that the compound has the property of exhibiting a mesophase between a crystal phase (low temperature side) and an isotropic phase (high temperature side) when the temperature is changed. As a specific observation method, by observing under a polarizing microscope while heating or cooling the compound with a hot stage or the like, the optical anisotropy and fluidity derived from the liquid crystal phase can be confirmed.

[0069] The optical element of the present invention described later is preferably produced by dissolving a composition containing the compound represented by the general formula (I) in a solvent and coating it. The precipitation concentration of the compound represented by the general formula (I) in the solvent at 25 °C is preferably 10% by mass or more.

[0070] [Composition Containing Compound Represented by General Formula (I)] A composition containing the compound represented by the general formula (I) (hereinafter, also referred to as "the composition of the present invention") will be described. The content of the compound represented by the general formula (I) in the composition of the present invention is not particularly limited, but is preferably 5 to 100% by mass, more preferably 20 to 99% by mass, still more preferably 30 to 99% by mass, and particularly preferably 40 to 99% by mass, based on the total mass of the solid content in the composition. Note that the solid content means components (non-volatile components) other than the solvent in the composition. As long as it is other than the solvent, even if the property is a liquid component, it is regarded as a solid content. The composition may use the compound represented by the general formula (I) alone or in combination of two or more. When using two or more, it is preferable that the total content is 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, when producing an optically anisotropic layer from the composition, the compounds in the composition can be easily oriented, and a desired orientation pattern can be easily produced, which is preferable.

[0072] That the composition has liquid crystallinity means that the composition has the property of expressing a mesophase between a crystal phase (low temperature side) and an isotropic phase (high temperature side) when the temperature is changed. As a specific observation method, while heating or cooling the composition with a hot stage or the like, the optical anisotropy and fluidity derived from the liquid crystal phase can be confirmed by observing under a polarized light microscope.

[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 the general formula (I). Hereinafter, other components will be described.

[0075] <Other liquid crystal compounds> The composition of the present invention may contain a liquid crystal compound that is not the compound represented by the general formula (I) (also referred to as "other liquid crystal compounds"). The other liquid crystal compounds may be rod-shaped liquid crystal compounds or disc-shaped liquid crystal compounds, but rod-shaped liquid crystal compounds are preferred. Further, the other liquid crystal compounds are preferably liquid crystal compounds having a polymerizable group (other polymerizable liquid crystal compounds). Examples of the rod-shaped liquid crystal compounds as the other liquid crystal compounds include rod-shaped nematic liquid crystal compounds. As the above rod-shaped nematic liquid crystal compounds, azomethines, azoxyes, cyanobiphenyls, cyanophenyl esters, benzoic acid esters, phenyl esters of cyclohexanecarboxylic acid, cyanophenylcyclohexanes, cyano-substituted phenylpyrimidines, alkoxy-substituted phenylpyrimidines, phenyldioxanes, tolanes or alkenylcyclohexylbenzonitriles are preferred. As the other liquid crystal compounds, not only low-molecular liquid crystal compounds but also high-molecular liquid crystal compounds can be used.

[0076] The liquid crystal compound having a polymerizable group is obtained by introducing a polymerizable group into the liquid crystal compound. Examples of the polymerizable group include P in the general formula (I) 1 and P 2 and the polymerizable groups exemplified therein. The number of polymerizable groups in the liquid crystal compound having a polymerizable group is preferably 1 to 6, more preferably 1 to 3. The other liquid crystal compounds preferably have a high refractive index anisotropy Δn. Specifically, 0.15 or more is preferred, 0.18 or more is more preferred, and 0.22 or more is even more preferred. The upper limit is not particularly limited, but it is often 0.60 or less. Further, by mixing and using the compound represented by the general formula (I) and the other liquid crystal compounds, the crystallization temperature as a whole can also be greatly reduced. Examples of other liquid crystal compounds include those described in Makromol.Chem., Vol. 190, p. 2255 (1989), Advanced Materials, Vol. 5, p. 107 (1993), U.S. Patent No. 4,683,327, U.S. Patent No. 4,983,479, No. 5,622,648, No. 5,770,107, International Publication WO95 / 22586, WO95 / 24455, WO97 / 00600, WO98 / 23580, WO98 / 52905, JP-A-1-272551, JP-A-6-16616, JP-A-7-110469, JP-A-11-80081, and JP-A-2001-328973, etc. 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 it is preferably 95% by mass or less, more preferably 1 to 80% by mass, still more preferably 1 to 70% by mass, and particularly preferably 1 to 60% by mass with respect to the total mass of the solid content in the composition. The composition of the present invention may use one kind of other liquid crystal compound alone or two or more kinds thereof. When two or more kinds are used, it is preferable that the total content thereof is 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 by ultraviolet irradiation. Examples of the photopolymerization initiator include α-carbonyl compounds, acyloin ethers, α-hydrocarbon-substituted aromatic acyloin compounds, polynuclear quinone compounds, phenazine compounds, and oxadiazole compounds. Also, compounds having an oxime ester structure are preferable. 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 it is preferably 0.1 to 20% by mass, more preferably 1 to 8% by mass with respect to the total mass of the compound represented by the general formula (I) (when the composition contains other liquid crystal compounds, with respect to the total mass of the compound represented by the general formula (I) and the other liquid crystal compounds). The composition of the present invention may use a polymerization initiator alone or in combination of two or more. When using two or more, the total content is preferably within the above range.

[0078] <Surfactant> The composition of the present invention may contain a surfactant that contributes to the formation of a stable or rapid liquid crystal phase (for example, nematic phase, cholesteric phase). Examples of the surfactant 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 2014-119605, and compounds described in paragraphs 0020 to 0031 of JP-A 2013-47204. Examples of the fluorine-containing (meth) acrylate polymer that can be used as a surfactant also include the polymers described in paragraphs 0018 to 0043 of JP-A 2007-272185. When the composition of the present invention contains a surfactant, the content of the surfactant is not particularly limited. However, it is preferably 0.001 to 10% by mass, more preferably 0.05 to 3% by mass, based on the total mass of the compound represented by general formula (I) (when the composition contains other liquid crystal compounds, based on the total mass of the compound represented by general formula (I) and other liquid crystal compounds). The composition of the present invention may use a surfactant alone or in combination of two or more. When using two or more, the total content is preferably within the above range.

[0079] <Chiral agent> The composition of the present invention may contain a chiral agent. When the composition of the present invention 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, an axial 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 axial 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% by mass, more preferably 1.0 to 10% by mass, based on the total mass of the compound represented by the general formula (I) (when the composition contains other liquid crystal compounds, based on the total mass of the compound represented by the general formula (I) and the other liquid crystal compounds). The composition of the present invention may use one kind of chiral agent alone or two or more kinds thereof. When two or more kinds are used, it is preferable that the total content is within the above range.

[0080] <Solvent> The composition of the present invention may contain a solvent. The solvent preferably can dissolve each component of the composition of the present invention, and examples thereof include chloroform, methyl ethyl ketone, and the like. 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 solid content concentration of the composition 0.5 to 20% by mass, more preferably 1 to 10% by mass. The composition of the present invention may use one kind of solvent alone or two or more kinds thereof. When two or more kinds are used, it is preferable that the total content is within the above range.

[0081] In addition to the above, the composition of the present invention may contain other components such as antioxidants, ultraviolet absorbers, sensitizers, stabilizers, plasticizers, chain transfer agents, polymerization inhibitors, defoamers, leveling agents, thickeners, flame retardants, surfactants, dispersants, and color materials such as dyes and pigments.

[0082] Further, by imparting a twist component to the composition of the present invention and by laminating different retardation layers, it is also preferable to make the optically anisotropic layer substantially broadband with respect to the wavelength of incident light. For example, in the optically anisotropic layer, a method of realizing a broadband patterned λ / 2 plate by laminating two layers of liquid crystal having different twist directions is disclosed in Japanese Patent Application Laid-Open No. 2014-089476 and the like, and can be preferably used in the optical element of the present disclosure.

[0083] 〔Cured Product and Optically Anisotropic Body〕 A cured product and an optically anisotropic body obtained by curing the composition of the present invention will be described. The method for curing (polymerization curing) the composition of the present invention is not particularly limited, and known methods can be adopted. For example, there is an embodiment having a step X of bringing a predetermined substrate into contact 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 orient the compound represented by the general formula (I) and then performing a curing treatment. According to this embodiment, the compound represented by the general formula (I) can be fixed in an oriented state, and an optically anisotropic body (for example, an optically anisotropic layer) can be formed.

[0084] Hereinafter, the procedures of step X and step Y will be described in detail.

[0085] Step X is a step of bringing a predetermined substrate into contact with the composition to form a composition layer on the substrate. The type of the substrate to be used is not particularly limited, and known substrates (for example, resin substrates, glass substrates, ceramic substrates, semiconductor substrates, and metal substrates) can be mentioned. The method of bringing the substrate into contact with the composition is not particularly limited, and examples thereof include a method of applying the composition onto the substrate and a method of immersing the substrate in the composition. Note that after bringing the substrate into contact with the composition, a drying treatment may be performed as 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 orient the compound represented by the general formula (I) and then performing a curing treatment. By subjecting the composition layer to a heat treatment, the compound represented by the general formula (I) is oriented to form a liquid crystal phase. For example, when a chiral agent is included in the composition layer, a cholesteric liquid crystal phase is formed. The conditions for the heat treatment are not particularly limited, and optimal conditions are selected according to the type of the compound represented by the general formula (I).

[0087] The method of the curing treatment is not particularly limited, and examples thereof include a photocuring treatment and a thermosetting treatment. Among them, a light irradiation treatment is preferable, and an ultraviolet irradiation treatment is more preferable. For the 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 the liquid crystal phase is fixed. In particular, when the composition contains a chiral agent, a layer in which the cholesteric liquid crystal phase is fixed is formed. Note that these layers do not necessarily need to exhibit liquid crystallinity anymore. More specifically, for example, the state where the cholesteric liquid crystal phase is "fixed" is the most typical and preferable mode in which the orientation of the compound represented by the general formula (I) that is in the cholesteric liquid crystal phase is maintained. More specifically, it is preferably a state in which the layer has no fluidity in the temperature range of usually 0 to 50 °C, and more severely -30 to 70 °C, and can stably maintain the fixed orientation form without changing the orientation form due to an external field or an external force.

[0089] 〔Optical Element〕 The optical element of the present invention has an optically anisotropic layer formed using the composition of the present invention described above. The above-mentioned optically anisotropic layer has an alignment pattern. The above alignment pattern is an optical element in which the direction of the optical axis derived from the compound contained in the above composition continuously rotates and changes along at least one direction in the plane. The above alignment pattern is preferably an alignment pattern in which the direction of the optical axis derived from the compound represented by the general formula (I) continuously rotates and changes along at least one direction in the plane, or an alignment pattern in which the directions of the optical axes derived from the compound represented by the general formula (I) and other liquid crystal compounds continuously rotate and change along at least one direction in the plane. Since the optical element of the present invention has an alignment pattern in which the direction of the optical axis continuously rotates and changes along at least one direction in the plane, the light incident on the optical element can be diffracted. Since the compound represented by the general formula (I) is a compound having a high refractive index anisotropy Δn, the diffraction efficiency can be increased. Regarding the optical element, reference can be made to the descriptions in

[0067] to

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

[0090] The optical element of the present invention can be applied as an optical member such as an Augmented Reality (AR) video projection device.

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

Examples

[0092] The present invention will be described more specifically with reference to the following examples and comparative examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be appropriately changed 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.

[0093] Synthesis examples of Compounds A-1 to A-20 are shown below. The structural formulas of Compounds A-1 to A-20 are as described above.

[0094] <Synthesis Example 1: Synthesis of Compound A-1> Compound A-1 was synthesized according to the following scheme. Compound 1 was synthesized according to International Publication No. 2019 / 182129, and Compound 6 was synthesized according to International Publication No. 2007 / 140183. Ac represents an acetyl group, Ms represents a methanesulfonyl group (-SO2CH3), and TMS represents a trimethylsilyl group (-Si(CH3)3).

[0095]

Chemical formula

[0096] (1) Synthesis of Compound 2 Compound 1 (5.47 g, 35.5 mmol) was dissolved in a mixed solution of tetrahydrofuran (THF) (30 mL) and pyridine (15 mL). The resulting solution was cooled in an ice-water bath, acetic anhydride (Ac2O) (5.44 g, 53.3 mmol) and 4-dimethylaminopyridine (DMAP) (0.43 g, 3.6 mmol) were added, and the mixture was stirred at room temperature (25 °C) for 3 hours. Ethyl acetate (50 mL) and water (50 mL) were added to the resulting solution, and then the mixture was extracted with ethyl acetate. The obtained organic layer was washed with brine and dried over magnesium sulfate. The organic layer was filtered, the solvent was distilled off under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain Compound 2 (6.18 g, 32.8 mmol). The yield was 92.4%.

[0097] (2) Synthesis of Compound 3 4-Bromothiophenol (9.50 g, 50.3 mmol) and 2-bromoethyl acetate (8.39 g, 50.3 mmol) were dissolved in acetonitrile (100 mL), potassium carbonate (13.9 g, 100 mmol) was added, and the mixture was stirred under reflux for 2 hours. The resulting solution was cooled to room temperature, ethyl acetate (100 mL) and 1 mol / L hydrochloric acid (200 mL) were added, and then the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and the organic layer was filtered. The solvent was distilled off under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain Compound 3 (12.6 g, 45.8 mmol). The yield was 90.9%.

[0098] (3) Synthesis of Compound 4 Under a nitrogen atmosphere, compound 3 (10.0 g, 36.3 mmol) was dissolved in THF (100 mL), and triethylamine (36.8 g, 363 mmol) was added. After nitrogen bubbling of the resulting solution was carried out for 1 hour, trimethylsilylacetylene (3.93 g, 40.0 mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.84 g, 0.73 mmol) and CuI (0.14 g, 0.73 mmol) were added, and the mixture was stirred under heating under reflux for 6 hours. The resulting solution was filtered and washed successively with water, 1 mol / L hydrochloric acid, aqueous sodium bicarbonate solution, and brine. The obtained organic layer was dried over sodium sulfate, and the organic layer was filtered. The solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain compound 4 (9.33 g, 31.9 mmol). The yield was 79.2%.

[0099] (4) Synthesis of compound 5 Compound 4 (8.39 g, 28.7 mmol) was dissolved in THF (50 mL). The resulting solution was cooled in an ice-water bath, and a THF solution of tetra-n-butylammonium fluoride (TBAF) (1 mol / L, 31.6 mL, 31.6 mmol) was added, and the mixture was stirred at room temperature for 2 hours. The resulting solution was cooled in an ice-water bath, ethyl acetate (50 mL) and 1 mol / L hydrochloric acid (50 mL) were added, and then extraction was carried out with ethyl acetate. The obtained organic layer was washed successively with water, aqueous sodium bicarbonate solution, and brine. The obtained organic layer was dried over sodium sulfate, and the organic layer was filtered. The solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain compound 5 (5.10 g, 23.2 mmol). The yield was 80.7%.

[0100] (5) Synthesis of compound 7 Compound 6 (4.49 g, 18.1 mmol) was dissolved in THF (20 mL). The resulting solution was cooled to -10 °C, methanesulfonyl chloride (2.28 g, 19.9 mmol) and triethylamine (2.20 g, 21.7 mmol) were added, and the mixture was stirred at room temperature for 1 hour. The resulting solution was cooled in an ice-water bath, ethyl acetate (70 mL) and water (20 mL) were added, and then extraction was performed with ethyl acetate. The obtained organic layer was washed with brine and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 7 (5.70 g, 17.5 mmol). The yield was 97.0%.

[0101] (6) Synthesis of Compound 8 Compound 7 (4.00 g, 12.3 mmol) and 4-bromothiophenol (2.32 g, 12.3 mmol) were dissolved in dimethylacetamide (DMAc) (30 mL), potassium carbonate (2.03 g, 14.7 mmol) and potassium iodide (0.20 g, 1.2 mmol) were added, and the mixture was stirred at 85 °C for 2 hours. The resulting solution was cooled to room temperature, ethyl acetate (100 mL) and water (50 mL) were added, and then extraction was performed with ethyl acetate. The obtained organic layer was washed successively with water and brine and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 8 (4.00 g, 9.5 mmol). The yield was 77.5%.

[0102] (7) Synthesis of Compound 9 Under a nitrogen atmosphere, Compound 8 (2.30 g, 5.49 mmol) and Compound 5 (1.33 g, 6.04 mmol) were dissolved in THF (15 mL), and triethylamine (5.55 g, 54.9 mmol) was added. After nitrogen bubbling of the resulting solution was carried out for 20 minutes, Pd(PPh3)4 (0.32 g, 0.27 mmol) and CuI (0.11 g, 0.55 mmol) were added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (100 mL) and water (30 mL) were added to the resulting solution, and then extraction was performed with ethyl acetate. The obtained organic layer was washed successively with water and brine, and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 9 (1.62 g, 3.17 mmol). The yield was 57.7%.

[0103] (8) Synthesis of Compound A-1 Under a nitrogen atmosphere, Compound 9 (0.25 g, 0.40 mmol) and Compound 2 (0.22 g, 1.2 mmol) were dissolved in dimethylacetamide (DMAc) (5 mL), and triethylamine (0.98 g, 9.7 mmol) was added. After nitrogen bubbling of the resulting solution was carried out for 20 minutes, Pd(PPh3)4 (56 mg, 0.049 mmol) and CuI (19 mg, 0.097 mmol) were added, and the mixture was stirred at 80 °C for 4 hours. Ethyl acetate (20 mL) and water (20 mL) were added to the resulting solution, and then extraction was performed with ethyl acetate. The obtained organic layer was washed with brine, and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by recrystallization from MeOH to obtain Compound A-1 (0.25 g, 0.40 mmol). The yield was 42%. 1 H-NMR(CDCl3): δ = 2.05(s, 6H), 2.47(s, 3H), 2.95(t, 2H), 3.18(t, 2H), 4.11(s, 2H), 4.26(t, 2H), 4.28(t, 2H), 7.10(d, 1H), 7.16 - 7.28(m, 5H), 7.34(d, 2H), 7.41(d, 3H), 7.43 - 7.48(m, 4H)

[0104] <Synthesis Example 2: Synthesis of Compound A-2> Compound A-2 was synthesized according to the following scheme. Compound 10 was synthesized from 4-iodobenzyl alcohol according to WO 2019 / 182129, and compound 11 was synthesized according to J. Karsten, et al. Synthsis, 4, 539 (2011).

[0105]

Chemical Structure

[0106] (1) Synthesis of Compound 12 Compound 10 (1.60 g, 5.13 mmol) and compound 11 (1.21 g, 5.13 mmol) were dissolved in DMAc (10 mL), potassium carbonate (0.85 g, 6.2 mmol) and potassium iodide (0.09 g, 0.5 mmol) were added, and the mixture was stirred at 85 °C for 2 hours. The resulting solution was cooled to room temperature, ethyl acetate (100 mL) and water (50 mL) were added, and then the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and brine, and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain compound 12 (1.93 g, 4.27 mmol). The yield was 83.2%.

[0107] (2) Synthesis of Compound A-2 Under a nitrogen atmosphere, compound 12 (1.50 g, 3.32 mmol) and compound 5 (1.61 g, 7.30 mmol) were dissolved in DMAc (10 mL), and triethylamine (3.36 g, 33.2 mmol) was added. After nitrogen bubbling of the resulting solution for 20 minutes, Pd(PPh3)4 (0.19 g, 0.17 mmol) and CuI (0.06 g, 0.3 mmol) were added, and the mixture was stirred at room temperature for 4 hours. Ethyl acetate (10 mL) was added to the resulting solution, and the precipitate was filtered. The obtained solid was rinsed with ethyl acetate to obtain compound A-2 (1.52 g, 2.27 mmol). The yield was 68.3%. 11H-NMR (CDCl3): δ = 2.04 (s, 6H), 3.18 (t, 4H), 4.13 (s, 2H), 4.26 (t, 4H), 7.22 - 7.30 (m, 4H), 7.33 (d, 4H), 7.39 (d, 2H), 7.42 - 7.47 (m, 6H)

[0108] <Synthesis Example 3: Synthesis of Compound A-3> Compound A-3 was synthesized according to the following scheme. Compound 16 was synthesized according to WO 2011 / 050276, and Compound 13 was synthesized according to Chun, J.-H, et al. Org. Biomol. Chem. 11, 6300 (2013). TBS represents a tert-butyldimethylsilyl group.

[0109] [Chemical Formula]

[0110] (1) Synthesis of Compound 14 4-Bromothiophenol (28.0 g, 0.148 mol) and Compound 13 (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, ethyl acetate (500 mL) and water (400 mL) were added, and then the mixture was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and filtered. The solvent was distilled off under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain Compound 14 (52.2 g, 0.150 mol). The yield was 62.4%.

[0111] (2) Synthesis of Compound 15 Under a nitrogen atmosphere, compound 14 (32.0 g, 92.1 mmol) was dissolved in THF (320 mL), and triethylamine (92.8 g, 0.917 mol) was added. After nitrogen bubbling of the resulting solution was carried out 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 heating under reflux for 4 hours. The resulting solution was filtered through celite and washed successively with water, 1 mol / L hydrochloric acid, aqueous sodium bicarbonate solution, and brine. The obtained organic layer was dried over magnesium sulfate and filtered. The solvent was distilled off under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain compound 15 (28.4 g, 77.9 mmol). The yield was 84.9%.

[0112] (3) Synthesis of compound 16 Compound 15 (28.4 g, 77.9 mmol) was dissolved in a mixed solution of THF (140 mL) and methanol (MeOH) (140 mL), potassium carbonate (31.7 g, 0.229 mol) was added, and the mixture was stirred at room temperature for 1 hour. Water was added to the resulting solution, and then the mixture was extracted with ethyl acetate. The obtained organic layer was washed with brine and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain compound 16 (20.5 g, 70.1 mmol). The yield was 91.8%.

[0113] (4) Synthesis of compound 17 Compound 10 (0.86 g, 2.8 mmol) and methyl 5-iodosalicylate (0.77 g, 2.8 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 17 (1.38 g, 2.76 mmol). The yield was 99.8%.

[0114] (5) Synthesis of compound 18 Under a nitrogen atmosphere, Compound 17 (1.20 g, 2.43 mmol) and Compound 16 (1.56 g, 5.34 mmol) were dissolved in DMAc (10 mL), and triethylamine (2.46 g, 24.3 mmol) was added. After nitrogen bubbling of the resulting solution was carried out for 1 hour, Pd(PPh3)4 (0.14 mg, 0.12 mmol) and CuI (47 mg, 0.24 mmol) were added, and the mixture was stirred at room temperature for 2 hours. The resulting solution was cooled in an ice-water bath, ethyl acetate (50 mL) and water (20 mL) were added, and then extraction was performed with ethyl acetate. The obtained organic layer was washed successively with water and brine, and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 18 (1.83 g, 2.22 mmol). The yield was 91.5%.

[0115] (6) Synthesis of Compound 19 Compound 18 (1.83 g, 2.22 mmol) was dissolved in THF (15 mL). The resulting solution was cooled in an ice-water bath, and a THF solution of TBAF (1 mol / L, 4.7 mL, 4.7 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The resulting solution was cooled in an ice-water bath, chloroform (50 mL) and water (20 mL) were added, and then extraction was performed with chloroform. The obtained organic layer was washed with brine and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 19 (1.22 g, 1.97 mmol). The yield was 88.5%.

[0116] (7) Synthesis of Compound A-3 Compound 19 (1.22 g, 2.05 mmol) was dissolved in DMAc (5 mL). The resulting solution was cooled in an ice-water bath, acryloyl chloride (0.63 g, 7.0 mmol) was added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (50 mL) and water (20 mL) were added to the resulting solution, and then extraction was performed with ethyl acetate. The obtained organic layer was successively washed with water, aqueous sodium bicarbonate, and brine, and then dried over magnesium sulfate. After filtering the organic layer, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound A-3 (1.05 g, 1.49 mmol). The yield was 72.8%. 1H-NMR (CDCl3): δ = 3.221 (t, 2H), 3.226 (t, 2H), 4.350 (t, 2H), 4.352 (t, 2H), 5.23 (s, 2H), 5.848 (d, 1H), 5.850 (d, 1H), 6.094 (dd, 1H), 6.097 (dd, 1H), 6.40 (d, 2H), 6.98 (d, 1H), 7.32 - 7.38 (m, 4H), 7.40 - 7.51 (m, 6H), 7.53 - 7.60 (m, 3H), 8.02 (d, 1H)

[0117] <Synthesis Example 4: Synthesis of Compound A-4> Compound A-4 was obtained according to the same procedure as in Synthesis Example 3, except that Compound 20 obtained by esterifying methyl 5-iodosalicylate and 4-iodobenzoic acid was used instead of Compound 17.

[0118]

Chemical Structure

[0119] <Synthesis Example 5: Synthesis of Compound A-5> Compound A-5 was obtained according to the same procedure as in Synthesis Example 3, except that 4-bromo-3-methoxybenzyl alcohol synthesized according to Gilmartin, P. H. et al. Org. Lett. 22, 2914 (2020) was used instead of Compound 10, and Compound 11 was used instead of methyl 5-iodosalicylate.

[0120] <Synthesis Example 6: Synthesis of Compound A-6> Compound A-6 was obtained according to the same procedure as in Synthesis Example 3, except that 2-methyl-4-iodophenol was used instead of methyl 5-iodosalicylate.

[0121] <Synthesis Example 7: Synthesis of Compound A-7> Compound A-7 was obtained according to the same procedure as in Synthesis Example 3, except that 4-bromo-2-fluorophenol was used instead of methyl 5-iodosalicylate.

[0122] <Synthesis Example 8: Synthesis of Compound A-8> Compound A-8 was obtained according to the same procedure as in Synthesis Example 3, except that Compound 21 synthesized according to Chun, J.-H, et al. Org. Biomol. Chem. 11, 6300 (2013) was used instead of 4-iodobenzyl alcohol which is a raw material of Compound 10.

[0123]

Chemical Structure

[0124] <Synthesis Example 9: Synthesis of Compound A-9> Compound A-9 was obtained according to the same procedure as in Synthesis Example 3, except that Compound 21 was used instead of 4-iodobenzyl alcohol which is a raw material of Compound 10, and 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.

[0125] <Synthesis Example 10: Synthesis of Compound A-10> Compound A-10 was obtained according to the same procedure as in Synthesis Example 3, except that Compound 21 was used instead of 4-iodobenzyl alcohol, and 4-iodo-2,6-dimethylphenol was used instead of methyl 5-iodosalicylate.

[0126] <Synthesis Example 11: Synthesis of Compound A-11> Compound A-11 was obtained according to the same procedure as in Synthesis Example 3, except that 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.

[0127] <Synthesis Example 12: Synthesis of Compound A-12> Compound A-12 was obtained according to the same procedure as in Synthesis Example 3, except that 4-(4-bromophenyl)benzyl alcohol synthesized according to EP2407502 was used instead of 4-iodobenzyl alcohol.

[0128] <Synthesis Example 13: Synthesis of Compound A-13> Compound A-13 was obtained according to the same procedure as in Synthesis Example 1, except that 4-iodophenol was used instead of 4-bromothiophenol.

[0129] <Synthesis Example 14: Synthesis of Compound A-14> Compound A-14 was synthesized according to the same procedure as in Synthesis Example 3, except that compound 22 synthesized according to the following scheme was used instead of compound 17.

[0130]

Chemical formula

[0131] (1) Synthesis of Compound 22 Compound 10 (3.00 g, 9.61 mmol) and methyl 2,5-dihydroxybenzoate (0.81 g, 4.86 mmol) were dissolved in DMAc (20 mL), potassium carbonate (1.59 g, 11.5 mmol) and potassium iodide (0.16 g, 0.96 mmol) were added, and the mixture was stirred at 85 °C for 3 hours. The resulting solution was cooled to room temperature, water (100 mL) was added, and the precipitate was filtered. The obtained solid was purified by flash column chromatography to obtain compound 22 (1.81 g, 3.02 mmol). The yield was 62.8%.

[0132] <Synthesis Example 15: Synthesis of Compound A-15> Compound A-15 was synthesized according to the following scheme. Ac represents an acetyl group.

[0133] [Chemical formula]

[0134] (1) Synthesis of Compound 23 Under a nitrogen atmosphere, 2-methyl-4-iodophenol (1.60 g, 6.84 mmol) and Compound 5 (1.81 g, 8.20 mmol) were dissolved in THF (10 mL), and triethylamine (6.92 g, 68.4 mmol) was added. After nitrogen bubbling of the resulting solution was carried out for 1 hour, Pd(PPh3)4 (0.40 g, 0.34 mmol) and CuI (0.13 g, 0.68 mmol) were added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (30 mL) was added to the resulting solution, and the mixture was filtered. Water (30 mL) was added to the resulting solution, and then the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water, 1 mol / L hydrochloric acid, and brine, and then dried over magnesium sulfate. After the organic layer was filtered, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 18 (2.15 g, 6.59 mmol). The yield was 96.4%.

[0135] (2) Synthesis of Compound 24 Compound 23 (0.77 g, 2.4 mmol) and Compound 10 (0.74 g, 2.4 mmol) were dissolved in DMAc (15 mL), potassium carbonate (0.39 g, 2.9 mmol) and potassium iodide (0.04 g, 0.3 mmol) were added, and the mixture was stirred at 85 °C for 2 hours. The resulting solution was cooled to room temperature, ethyl acetate (70 mL) and water (50 mL) were added, and then the mixture was extracted with ethyl acetate. The obtained organic layer was washed successively with water and brine, and then dried over magnesium sulfate. After the organic layer was filtered, the solvent was distilled off under reduced pressure, and the obtained residue was rinsed with a mixed solvent of ethyl acetate and hexane to obtain Compound 24 (0.87 g, 1.6 mmol). The yield was 68%.

[0136] (3) Synthesis of Compound 25 Under a nitrogen atmosphere, Compound 24 (0.43 g, 0.78 mmol) was dissolved in THF (5 mL), and triethylamine (0.79 g, 7.8 mmol) was added. After nitrogen bubbling of the resulting solution was carried out for 20 minutes, tetramethylsilylacetylene (0.13 mL, 0.94 mmol), Pd(PPh3)4 (45.3 mg, 0.0392 mmol), and CuI (15.0 g, 0.0784 mmol) were added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (30 mL) and water (10 mL) were added to the resulting solution, and then extraction was carried out with ethyl acetate. The obtained organic layer was washed with brine, dried over magnesium sulfate, and the organic layer was filtered. The solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 25 (0.39 g, 0.76 mmol). The yield was 97%.

[0137] (4) Synthesis of Compound 26 Compound 25 (0.39 g, 0.76 mmol) was dissolved in THF (5 mL). The resulting solution was cooled in an ice-water bath, a THF solution of TBAF (1 mol / L, 0.86 mL, 0.86 mmol) was added, and the mixture was stirred at room temperature for 1 hour. Ethyl acetate (30 mL) and water (10 mL) were added to the resulting solution, and then extraction was carried out with ethyl acetate. The obtained organic layer was washed with brine, dried over magnesium sulfate. After the organic layer was filtered, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain Compound 26 (0.33 g, 0.75 mmol). The yield was 99%.

[0138] (5) Synthesis of Compound A-15 Under a nitrogen atmosphere, compound 24 (0.40 g, 0.73 mmol) and compound 26 (0.35 g, 0.80 mmol) were dissolved in THF (5 mL), and triethylamine (0.73 g, 7.3 mmol) was added. After nitrogen bubbling of the resulting solution was carried out for 1 hour, Pd(PPh3)4 (42 mg, 0.036 mmol) and CuI (14 mg, 0.073 mmol) were added, and the mixture was stirred at room temperature for 1 hour. After chloroform (30 mL) was added to the resulting solution, the solvent was distilled off under reduced pressure, and the obtained residue was purified by flash column chromatography to obtain compound A-15 (0.24 g, 0.28 mmol). The yield was 39%. 1H-NMR(CDCl3):δ=2.04(s, 6H), 2.30(s, 6H), 3.18(t, 4H), 4.26(t, 4H), 5.13(br s, 4H), 6.80 - 6.85(m, 2H), 7.17 - 7.21(m, 2H), 7.31 - 7.38(m, 4H), 7.40 - 7.47(m, 8H), 7.54 - 7.59(m, 2H)

[0139] <Synthesis Example 16: Synthesis of Compound A-16> Compound A-16 was obtained according to the same procedure as in Synthesis Example 3, except that 5-bromothiophen-2-ylmethanol synthesized according to Lee, J. et al. J. Org. Chem. 77, 4821 (2012) was used instead of 4-iodobenzyl alcohol.

[0140] <Synthesis Example 17: Synthesis of Compound A-17> Compound A-17 was synthesized according to the same procedure as in Synthesis Example 3, except that 2-methyl-4-iodophenol was used instead of 4-bromothiophenol and compound 27 synthesized according to the following scheme was used instead of compound 17.

[0141]

Chemical Structure

[0142] (1) Synthesis of Compound 27 4-Bromothiophenol (11.3 g, 59.8 mmol) and 1,2-dibromoethane (5.63 g, 30.0 mmol) were dissolved in acetonitrile (150 mL), potassium carbonate (16.6 g, 120 mmol) was added, and the mixture was stirred at 80 °C for 2 hours. The resulting solution was cooled to room temperature, ethyl acetate (50 mL) and water (50 mL) were added, and the precipitate was filtered to obtain Compound 27 (4.62 g, 11.4 mmol). The yield was 38.1%.

[0143] <Synthesis Example 18: Synthesis of Compound A-18> Compound A-18 was synthesized according to the same procedure as in Synthesis Example 3, except that Compound 28 synthesized according to the following scheme was used instead of Compound 17.

[0144]

Chemical formula

[0145] (1) Synthesis of Compound 28 Methyl 5-iodosalicylate (8.88 g, 31.9 mmol) and 1,2-dibromoethane (3.00 g, 16.0 mmol) were dissolved in DMAc (30 mL), potassium carbonate (5.30 g, 38.3 mmol) and potassium iodide (0.27 g, 0.16 mmol) were added, and the mixture was stirred at 85 °C for 3 hours. The resulting solution was cooled to room temperature, water (100 mL) was added, and the precipitate was filtered. The obtained solid was rinsed with ethyl acetate and then dissolved in chloroform, and MeOH was added for reprecipitation to obtain Compound 28 (2.99 g, 5.14 mmol). The yield was 32.2%.

[0146] <Synthesis Example 19: Synthesis of Compound A-19> Compound A-19 was obtained according to the same procedure as in Synthesis Example 3, except that 3-bromopropanol was used instead of 2-bromoethanol which is the raw material of Compound 13.

[0147] <Synthesis Example 20: Synthesis of Compound A-20> Compound A-20 was obtained in the same procedure as in Synthesis Example 3, except that 4-bromobutanol was used instead of 2-bromoethanol, which is the raw material of Compound 13.

[0148] <Synthesis of Compound RA-1> Compound RA-1 was synthesized as a comparative compound according to Synthesis Example 1 of JP-A-2005-15406.

[0149] <Synthesis of Compound RA-2> Compound RA-2 was obtained as a comparative compound according to International Publication No. 2018 / 034216.

[0150] [Chemical formula]

[0151] [Examples 1 to 19, Comparative Examples 1 and 2] [Evaluation] In Examples 1 to 19, the evaluations described below were performed using Compounds A-1, A-3 to A-20, respectively. Also, in Comparative Examples 1 and 2, the evaluations described below were performed using Compounds RA-1 and RA-2, respectively.

[0152] [Liquid crystal property evaluation] The compounds of each Example and Comparative Example (Compounds A-1, A-3 to A-20, Compounds RA-1 and RA-2) were heated on a hot stage, observed with a polarizing microscope, the phase transition temperature was measured, and the presence or absence of liquid crystal property was evaluated. When there was liquid crystal property, it was evaluated as A, and when there was no liquid crystal property, it was evaluated as B. The results are shown in Table 1.

[0153] [Measurement of Δn (refractive index anisotropy)] The Δn values of the compounds of each example and comparative example (compounds A-1, A-3 to A-20, compounds RA-1 and RA-2), which are the compounds to be measured, were measured by the method using a wedge-shaped liquid crystal cell described on page 202 of the Liquid Crystal Handbook (edited by the Liquid Crystal Handbook Editorial Committee, published by Maruzen Co., Ltd., 2000). The Δn was taken as the measured value at a wavelength of 550 nm at 30 °C or the lower limit temperature of the nematic phase + 0 to 10 °C. In the case of compounds that are likely to crystallize or compounds that do not have liquid crystallinity, evaluation was performed using a mixture with other liquid crystal compounds, and Δn was estimated from the extrapolated value. As the above-mentioned other liquid crystal compound, L-1-1 described below was used. The above mixture used was one mixed so that the compound to be measured / L-1-1 = 1 / 2 (mass ratio). When Δn was 0.35 or more, it was evaluated as A, when Δn was 0.32 or more and less than 0.35, it was evaluated as B, when Δn was 0.30 or more and less than 0.32, it was evaluated as C, and when Δn was less than 0.30, it was evaluated as D. The results are shown in Table 1.

[0154]

Chemical formula

[0155] <Solubility evaluation> The solubility of the compounds of each example and comparative example (compounds A-1, A-3 to A-20, compounds RA-1 and RA-2) in methyl ethyl ketone was evaluated. After preparing a solution in which the compound was dissolved by ultrasonic wave or heating, it was observed whether the compound precipitated in the solution at room temperature (25 °C). 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 10% by mass or more, the solubility was evaluated as A, and when the precipitation concentration was less than 10% by mass, the solubility was evaluated as B. The results are shown in Table 1.

[0156] <Light resistance / durability evaluation> As shown below, the durability of the optically anisotropic layer prepared using the composition containing compounds A-1, A-3 to A-20, compounds RA-1, and RA-2 was evaluated.

[0157] (Preparation of optically anisotropic layer for light resistance / durability test) A coating composition having the following composition was prepared and spin-coated onto glass with a rubbed alignment film. Each coating composition was heated to a temperature at which it exhibited a nematic phase on a hot plate and irradiated with ultraviolet light of 300 mJ / cm 2 through a filter that cuts off light with a wavelength of 350 nm or less, to produce an optically anisotropic layer for light resistance / durability testing (an optically anisotropic layer for light resistance testing and an optically anisotropic layer for durability testing). ――――――――――――――――――――――――――――――――― Composition of the coating composition ――――――――――――――――――――――――――――――――― · 25 parts by mass of the compound of each of the examples and comparative examples shown in Table 1 below · 75 parts by mass of the following polymerizable liquid crystal compound L-1 · A polymerization initiator (manufactured by BASF, Irgacure (registered trademark) 907) 2 parts by mass · 0.1 part by mass of the following leveling agent T-1 · 1940 parts by mass of chloroform ―――――――――――――――――――――――――――――――――

[0158] The polymerizable liquid crystal compound L-1 is a mixture containing the following L-1-1 / L-1-2 / L-1-3 at a mass ratio of 84 / 14 / 2.

[0159]

Chemical formula

[0160] The leveling agent T-1 is a compound having the following structure.

[0161]

Chemical formula

[0162] (Light resistance evaluation) The optical anisotropic layer for the light resistance / durability test that was fabricated was irradiated with light using a Super Xenon Weather Meter SX75 manufactured by Suga Test Instruments Co., Ltd. As an ultraviolet cut filter, KU-1000100 manufactured by King Seisakusho Co., Ltd. was used, and a light resistance test was conducted by irradiating light of 5 million lx for 50 hours under oxygen blocking conditions. 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 optical anisotropic layer before and after the light resistance test was measured, and when the Re change rate shown below was less than 10%, the light resistance was evaluated as A, and when the Re change rate was 10% or more, the light resistance was evaluated as B. The smaller the Re change rate, the better the light resistance. The results are shown in Table 1. Re is the in-plane retardation. Re change rate (%) = [100 × {|(Re after the test) - (Re before the test)|} / (Re before the test)] Re was measured at a wavelength of 550 nm with an Axoscan from Axometrix, and the measurement temperature was room temperature.

[0163] (Durability evaluation) For the fabricated optical anisotropic layer, a damp heat durability test was conducted by allowing it to pass through 136 hours at 100°C and a relative humidity of 95%RH. The Re change rate before and after the durability test was evaluated, and when the Re change rate was less than 10%, the durability was evaluated as A, and when the Re change rate was 10% or more, the durability was evaluated as B. The smaller the Re change rate, the better the durability. The results are shown in Table 1.

[0164] [Example 20] As Example 20, an optical element was fabricated using Compound A-9 as shown below.

[0165] [Fabrication of optical element] [Preparation of support and saponification treatment of support] As the support, a commercially available triacetyl cellulose film (Z-TAC manufactured by Fujifilm Corporation) was prepared. 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. Subsequently, on one side of the support, the alkaline solution described below was applied using a bar coater at an application rate of 14 mL (liter) / m 2 and the support was heated to 110°C and further conveyed under a steam type far-infrared heater (manufactured by Noritake Company Limited) for 10 seconds. Subsequently, again using a bar coater, 3 mL / m of pure water was applied to the alkaline solution-coated surface of the support. 2 Next, after repeating the water washing with a fountain coater and water draining with an air knife three times, the support was conveyed through a drying zone at 70°C for 10 seconds for drying, and the surface of the support was alkali saponified.

[0166] ――――――――――――――――――――――――――――――――― Alkaline solution ――――――――――――――――――――――――――――――――― · Potassium hydroxide 4.70 parts by mass · Water 15.80 parts by mass · Isopropyl alcohol 63.70 parts by mass · Surfactant SF-1: C 14 H 29 O(CH2CH2O)2OH 1.0 part by mass · Propylene glycol 14.8 parts by mass ―――――――――――――――――――――――――――――――――

[0167] <Formation of the undercoat layer> The following coating solution for forming the undercoat layer was continuously applied to the alkali saponified surface of the support using a #8 wire bar. The support on which the coating film was formed was dried with warm air at 60°C for 60 seconds and further with warm air at 100°C for 120 seconds to form the undercoat layer.

[0168] ――――――――――――――――――――――――――――――――― Coating solution for forming the undercoat layer ――――――――――――――――――――――――――――――――― · 2.40 parts by mass of the following modified polyvinyl alcohol · 1.60 parts by mass of isopropyl alcohol · 36.00 parts by mass of methanol · 60.00 parts by mass of water ―――――――――――――――――――――――――――――――――

[0169] Modified polyvinyl alcohol (the ratio of repeating units in the following structural formula is by mass).

[0170]

Chem.

[0171] <Formation of alignment film> On the support with the undercoat layer formed, the following coating solution for forming an alignment film was continuously coated with a #2 wire bar. The support on which the coating film of this coating solution for forming an alignment film was formed was dried on a hot plate at 60 °C for 60 seconds to form an alignment film.

[0172] ――――――――――――――――――――――――――――――――― Coating solution for forming an alignment film ――――――――――――――――――――――――――――――――― · 1.00 part by mass of photo-alignment material D · 16.00 parts by mass of water · 42.00 parts by mass of butoxyethanol · 42.00 parts by mass of propylene glycol monomethyl ether ―――――――――――――――――――――――――――――――――

[0173] Photo-alignment material D is a compound having the following structure.

[0174]

Chem.

[0175] <Exposure of alignment film> The alignment film was exposed using the exposure apparatus of FIG. 5 of International Publication No. 2020 / 22496 to form an alignment film P-1 having an alignment pattern. In the exposure apparatus, a laser that emits laser light with a wavelength of 325 nm was used. The exposure amount by interference light was 2000 mJ / cm 2 Note that one period of the alignment pattern formed by the interference of two laser lights (the length in which the optical axis derived from the liquid crystal compound rotates 180°) was controlled by changing the crossing angle (crossing angle β) of the two lights.

[0176] <Formation of the optically anisotropic layer> As the composition for forming the optically anisotropic layer, the following composition E-1 was prepared.

[0177] ――――――――――――――――――――――――――――――――― Composition E-1 ――――――――――――――――――――――――――――――――― · 100.00 parts by mass of liquid crystal compound A-9 · Photoinitiator (manufactured by BASF, Irgacure (registered trademark) 907) 3.00 parts by mass · 0.08 parts by mass of the leveling agent T-1 described above · 927.7 parts by mass of methyl ethyl ketone ―――――――――――――――――――――――――――――――――

[0178] The optically anisotropic layer was formed by applying composition E-1 onto the alignment film P-1 in multiple layers. Here, the multiple-layer coating means first applying the first layer of composition E-1 onto the alignment film, performing ultraviolet curing after heating and cooling to produce a liquid crystal immobilization layer, and then, for the second and subsequent layers, applying by overcoating on the liquid crystal immobilization layer and repeating ultraviolet curing after heating and cooling in the same manner. By forming it by multiple-layer coating, even when the film thickness of the liquid crystal layer becomes thick, the alignment direction of the alignment film is reflected from the lower surface (the surface on the alignment film P-1 side) to the upper surface of the liquid crystal layer.

[0179] First, for the first layer, the above composition E-1 was applied onto the alignment film P-1, and the coating film was heated to 80°C on a hot plate and then cooled to 50°C. After that, under a nitrogen atmosphere, ultraviolet light with a wavelength of 365 nm was irradiated onto the coating film at an irradiation dose of 300 mJ / cm 2 , thereby fixing the alignment of the liquid crystal compound. The film thickness of the liquid crystal layer of the first layer at this time was 0.3 μm.

[0180] For the second layer and subsequent layers, they were overcoated on this liquid crystal layer, and after heating and cooling under the same conditions as above, an ultraviolet effect was performed to fabricate a liquid crystal fixing layer (hardened layer). In this way, overcoating was repeated until the retardation reached 325 nm to form an optically anisotropic layer and fabricate an optical element G-1.

[0181] Regarding the optically anisotropic layer in this example, it was confirmed by a polarizing microscope that it had a periodic alignment surface as shown in FIG. 3 of International Publication No. 2020 / 22496. In the alignment pattern of this optically anisotropic layer, one period Λ in which the optical axis derived from liquid crystal compound A-9 rotates 180° was 1.0 μm. The period Λ was obtained by measuring the period of the light and dark pattern observed under cross Nicol conditions using a polarizing microscope.

[0182] <Measurement of diffraction efficiency> An evaluation optical system was prepared by arranging an evaluation light source, a polarizer, a quarter-wave plate, an optical element G-1, and a screen in this order. A laser pointer with a wavelength of 650 nm was used as the evaluation light source, and SAQWP05M-700 manufactured by Thorlabs was used as the quarter-wave plate. The slow axis of the quarter-wave plate was arranged at a 45° relationship with respect to the absorption axis of the polarizer. Also, the optical element G-1 was arranged with the support surface facing the light source side. When the light transmitted through the polarizer and the quarter-wave plate from the evaluation light source was incident perpendicularly to the film surface of the optical element G-1, a part of the light transmitted through the optical element G-1 was diffracted, and a plurality of bright spots were confirmed on the screen. The intensities of each diffracted light and the 0th-order light corresponding to the bright spots on the screen were measured with a power meter, and the diffraction efficiency was calculated by the following formula. Diffraction efficiency = (first-order light intensity) / (0th-order light intensity + diffraction light intensity other than the first order) The obtained diffraction efficiency was as high as 99% or more.

[0183] <Liquid crystallinity of the composition> When the composition E-1 was dried to volatilize the solvent (methyl ethyl ketone), it was confirmed that the composition exhibited liquid crystallinity.

[0184] [Example 21] As Example 21, as shown below, a light guide element was fabricated using a composition containing Compound A-9 and a chiral agent.

[0185] As a composition for forming a cholesteric liquid crystal layer as shown in FIG. 6 of WO 2020 / 22496, the following composition E-2 was prepared. In the structural formula of the following chiral agent Ch-2, Bu represents an n-butyl group. ――――――――――――――――――――――――――――――――― Composition E-2 ――――――――――――――――――――――――――――――――― · Liquid crystal compound A-9 100.00 parts by mass · The following polymerization initiator PI-1 3.00 parts by mass · The following chiral agent Ch-1 4.40 parts by mass · The following chiral agent Ch-2 1.00 part by mass · Methyl ethyl ketone 201.31 parts by mass ―――――――――――――――――――――――――――――――――

[0186]

Chemical formula

[0187]

Chemical formula

[0188]

Chemical formula

[0189] In the same manner as <Preparation of the support and saponification treatment of the support>, <Formation of the undercoat layer>, <Formation of the alignment film>, and <Exposure of the alignment film> in Example 20 described above, an alignment film P-1 was prepared. On the alignment film P-1, the above composition E-2 was applied in multiple layers until the film thickness reached 3.5 μm to form a cholesteric liquid crystal layer. Here, the multiple-layer coating means that first, the first layer of the composition E-2 was applied on the alignment film, and after heating, ultraviolet curing was performed to prepare a liquid crystal immobilization layer. Then, for the second layer and subsequent layers, coating was performed by overcoating on the liquid crystal immobilization layer, and heating and ultraviolet curing were performed in the same manner and repeated. By forming through multiple-layer coating, even when the total thickness of the liquid crystal layer becomes thick, the alignment direction of the alignment film is reflected from the lower surface to the upper surface of the liquid crystal layer. As the first layer of the optically anisotropic layer, on the alignment film P-1, the composition E-2 was applied at 1000 rpm (rotations per minute) using a spin coater. The coating film was heated on a hot plate at 80 °C for 3 minutes, and then further at 50 °C, and ultraviolet light with a wavelength of 365 nm was irradiated on the coating film with an irradiation dose of 300 mJ / cm 2 by using a high-pressure mercury lamp in a nitrogen atmosphere, thereby fixing the alignment of the liquid crystal compound. For the second layer and subsequent layers, overcoating was performed on this liquid crystal layer, and heating and ultraviolet curing were performed under the same conditions as above to form a cholesteric liquid crystal layer. The formed cholesteric liquid crystal layer was bonded to a light guide plate (glass with a refractive index of 1.80 and a thickness of 0.50 mm) to produce a light guide element. Light with a wavelength of 532 nm was incident from the normal direction on the light guide plate side of the produced light guide element. As a result, it was confirmed that the incident light was reflected by the cholesteric liquid crystal layer at an angle exceeding the critical angle in a direction different from the specular reflection direction and was guided through the light guide plate.

[0190] <Liquid crystallinity of the composition> When the composition E-2 was dried to volatilize the solvent (methyl ethyl ketone), it was confirmed that it exhibited liquid crystallinity.

[0191]

Table 1

[0192] From the results shown in Table 1 above, it was found that the compounds represented by the general formula (I) have a high refractive index anisotropy Δn (Examples 1 to 19). In particular, from the comparison between Example 12 and the other examples, among the plurality of Xs present in the general formula (I) 1 and the plurality of Xs present 2 it was found that when at least any two of them represent -S-, the refractive index anisotropy Δn becomes even higher. Also, as described above, an optical element produced using a composition containing the compound represented by the general formula (I) was able to obtain a high diffraction efficiency. Furthermore, as described above, a light guide element could be produced using a composition containing the compound represented by the general formula (I) and a chiral agent. On the other hand, it was found that the refractive index anisotropy Δn of the comparative compounds that are not the compounds represented by the general formula (I) is lower than that of the compounds represented by the general formula (I) (Comparative Examples 1 and 2).

Claims

1. A compound represented by the following general formula (I). 【Chemical 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 of the following formulas (P-1) to (P-19). Sp １ and Sp ２ each independently represents a single bond or a divalent linking group formed by combining an alkylene group, an alkenylene group, -O-, -S-, -CO-, -SO-, -SO₂-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, or a plurality of these. However, Sp １ and Sp ２ do not represent a divalent linking group containing at least one group selected from the group consisting of an aromatic hydrocarbon ring group, an aromatic heterocyclic group, and an aliphatic hydrocarbon ring group. Z １ 、Z ２ and Z ３ are each independently a single bond, -O-, -S-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -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 -C≡C-. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When a plurality of R's are present, they may be the same or different. Z １ and Z ２ when each is present in a plurality, they may be the same or different. A plurality of Z's ３ may be the same or different. However, the Z ２ connected to Sp ３ represents a single bond. X １ and X ２ each independently represents a single bond or -S-. When there are a plurality of X １ and X ２ they may be the same or different from each other. However, among a plurality of X １ and a plurality of X ２ at least one of them represents -S-. k represents an integer of 2 to 4. m and n each independently represent an integer of 0 to 3. A plurality of m's may be the same or different. A １ 、A ２ 、A ３ and A ４ each independently represents a group represented by any one of the following general formulas (B-1) to (B-7), or a group formed by linking two or more and three or less groups represented by any one of the following general formulas (B-1) to (B-7). When there are a plurality of A ２ and A ３ may be the same or different from each other. A １ and A ４ when there are a plurality of each, may be the same or different from each other. 【Chemical 2】 In general formulas (B-1) to (B-7), W １ to W １８ each independently represents CR １ or N, and R １ represents a hydrogen atom or the following substituent L. Y １ to Y ６ each independently represents NR ２ , O or S, and R ２ represents a hydrogen atom or the following substituent L. G １ to G ４ each independently represents CR ３ R ４ , NR ５ , O or S, and R ３ to R ５ each independently represents a hydrogen atom or the following substituent L. M １ and M ２ each independently represents CR ６ or N, and R ６ represents a hydrogen atom or the following substituent L. * represents a bonding position. The substituent L is 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 amide group, a cyano group, a nitro group, a halogen atom or a polymerizable group represented by any one of the following formulas (P-1) to (P-19). However, when the above group described as the substituent L has -CH ２ -, at least one of -CH ２ - included in the above group is replaced by -O-, -CO-, -CH=CH- or -C≡C-, and the resulting group is also included in the substituent L. Further, when the above group described as the substituent L has a hydrogen atom, at least one of the hydrogen atoms included in the above group is replaced by at least one selected from the group consisting of a fluorine atom and a polymerizable group represented by any one of the following formulas (P-1) to (P-19), and the resulting group is also included in the substituent L. In the following formulas (P-1) to (P-19), * represents a bonding position, Me represents a methyl group, and Et represents an ethyl group. 【Chemical 3】

2. The compound according to claim 1, wherein n and m in the general formula (I) represent 0.

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

4. The plurality of X's present in the general formula (I) １ and the plurality of X's ２ wherein at least any two of them represent -S-, the compound according to any one of claims 1 to 3

5. In the general formula (I), n represents 0, m represents 0 or 1, and Sp ２ m at the position closest to Sp represents 0, and X １ linked to Sp １ is X １Ａ , Sp ２ Z linked to ３ X linked to ２ is X ２Ａ is taken as X １Ａ and X ２Ａ at least one of which represents -S-, and X １Ａ X other than １ and X ２Ａ X other than ２ represents a single bond, and Z ２ and Z ３ each independently represents a single bond, -O-, -CHR-, -CHRCHR-, -OCHR-, -CHRO-, -SO-, -SO ２ -, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NR-, -NR-CO-, -SO-CHR-, -CHR-SO-, -SO ２ -CHR-, -CHR-SO ２ -, -CF ２ O-, -OCF ２ -, -OCHRCHRO-, -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-. The compound according to claim 1. However, Z ２ linked to Sp ３ represents a single bond. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When there are a plurality of Rs, they may be the same or different.

6. P in the general formula (I) above １ and P ２ The compound according to any one of claims 1 to 5, wherein at least one of them represents a polymerizable group represented by any one of the formulas (P-1) to (P-19).

7. P in the general formula (I) １ represents a polymerizable group represented by any one of the formulas (P-1) to (P-19), n represents 0, and X linked to Sp １ represents -S-, and the compound according to any one of claims 1 to 6. １ ​

8. A in the general formula (I) １ , A ２ , A ３ and A ４ each independently represents a group represented by the general formula (B-1) or (B-2), the compound according to any one of claims 1 to 7. However, W in the general formula (B-1) １ and W ２ do not both represent N, and W ３ and W ４ do not both represent N. Also, W in the general formula (B-2) ５ and W ６ do not both represent N, and W ９ and W １０ do not both represent N.

9. A in the general formula (I) １ , A ２ , A ３ and A ４ The compound according to any one of claims 1 to 8, wherein at least one of them has the substituent L.

10. Z in the general formula (I) above １ , Z ２ and Z ３ each independently represents a single bond, —CHR—, —CHRCHR—, —OCHR—, —CHRO— or —OCHRCHRO—, the compound according to any one of claims 1 to 9. However, Z ２ linked to Sp ３ represents a single bond. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. When a plurality of Rs are present, they may be the same or different.

11. The compound according to claim 1, wherein the compound represented by the general formula (I) is a compound represented by the following general formula (I-2) or (I-3). 【Chemical Formula 4】 [Chemical Formula 5] In general formulas (I-2) and (I-3), T １ and T ２ each independently represents a hydrogen atom or a methyl group. r represents an integer of 1 to 5. t and v each independently represent 0 or 1. u represents 1 or 2. w represents an integer of 1 to 5. Q １ to Q １６ each independently represents a hydrogen atom or the substituent L. E １ ~E ６ each independently represents a hydrogen atom or the substituent L.

12. A composition comprising the compound according to any one of claims 1 to 11.

13. The composition according to claim 12, further comprising a polymerization initiator.

14. The composition according to claim 12 or 13, further comprising a chiral agent.

15. The composition according to any one of claims 12 to 14, having liquid crystallinity.

16. The composition according to any one of claims 12 to 15, for forming an optically anisotropic layer.

17. A cured product obtained by curing the composition according to any one of claims 12 to 16.

18. An optically anisotropic body obtained by curing the composition according to any one of claims 12 to 16.

19. Having an optically anisotropic layer formed using the composition according to any one of claims 12 to 16, the optically anisotropic layer has an alignment pattern, the alignment pattern is an alignment pattern in which the direction of the optical axis derived from the compound contained in the composition continuously rotates and changes along at least one direction in the plane, an optical element.

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

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