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

Abstract

The present invention addresses the problem of providing a compound that has excellent pattern orientation and can be cured to form an optically anisotropic layer having a high refractive index ne to an abnormal light beam and a high birefringence Δn. The second problem addressed by the present invention is to provide a composition, a composition, a cured product, an optically anisotropic body, an optical element, and a light guide element.　The compound according to the present invention is represented by formula (I). In formula (I), P1 and P2 each independently represent a hydrogen atom, a polymerizable group, or a monovalent substituent, and at least one of P1 or P2 is a polymerizable group. A1 and A2 each independently represent a divalent aromatic ring group which may have a substituent, or a divalent alicyclic group which may have a substituent, and at least one of n1 A1 or A2 is a fused ring structure represented by formula (Ia). In formula (Ia), two of X1, X2, X3, and X4 represent -C(*)=, and the other two of X1, X2, X3, and X4 each independently represent -N= or -C(RA)=.

Description

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

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

[0002] Recently, polarized light has been utilized in many optical devices or systems, and optical elements capable of controlling the reflection, concentration, and divergence of polarized light are in demand. In particular, optical elements having a high refractive index (ne) for extraordinary rays are in demand in order to reduce the performance variation of optical elements depending on the angle of incidence of light incident on the optical element. Compounds that provide a high refractive index (ne) for extraordinary rays are known, for example, compounds containing a tolan structure (hereinafter also referred to as "tolane compounds"). Because tolan compounds have a relatively high refractive index, optically anisotropic bodies formed using liquid crystal compositions containing tolan compounds tend to have a high refractive index and exhibit good incident angle-dependent diffraction efficiency, whether the tolan compound itself has liquid crystallinity or is used in combination with other liquid crystal compounds without liquid crystallinity. For example, Patent Document 1 discloses liquid crystal compounds having a tolan structure.

[0003] International Publication No. 2019 / 182129

[0004] The present inventors have studied the liquid crystal compound described in Patent Document 1 and found that the refractive index ne for extraordinary light rays in an optically anisotropic layer prepared using the liquid crystal compound after curing is insufficient, and have clarified that improvement is necessary. Furthermore, the optically anisotropic layer after curing is required to have a high birefringence Δn and excellent pattern alignment properties in which the compound is oriented along a pattern.

[0005] Therefore, an object of the present invention is to provide a compound that is capable of forming an optically anisotropic layer having a high refractive index (ne) for extraordinary light rays and a high birefringence (Δn) after curing, and that has excellent pattern alignment properties. Another object of the present invention is to provide a composition, a cured product, an optically anisotropic body, an optical element, and a light guide element.

[0006] As a result of extensive research into solving the above problems, the present inventors have found that the above problems can be solved by the following configuration.

[0007] [1] A compound represented by the formula (I) described below. [2] In the above formula (Ia), X １ , X ２ , X ３ , and X ４ Two of them represent -C(*)=, and X １ , X ２ , X ３ , and X ４ The other two are -C(R Ａ [3] The compound according to [1], wherein in the above formula (Ia), X １ and X ４ [4] The compound according to [1] or [2], wherein n1 Z in the formula (I) represents -C(*)=. １ [5] The compound according to any one of [1] to [3], wherein at least one of the following is —C≡C—: １ and A ２ [6] The compound according to any one of [1] to [4], wherein at least two of the n1 A's in the formula (I) are fused ring structures represented by the formula (Ia). １ and A ２ at least two of the X in the fused ring structure represented by formula (Ia) are fused ring structures represented by formula (Ia) １ and X ４ [7] The compound according to any one of [1] to [5], wherein in the above formula (I), P １ and P ２ [8] The compound according to any one of [1] to [6], wherein at least one of the following represents a polymerizable group selected from the group consisting of formulas (P-1) to (P-19) described below. １ and P ２The compound according to [7], wherein at least one of the following represents a polymerizable group selected from formula (P-1) and formula (P-2) described below. [9] The compound according to any one of [1] to [8], wherein in formula (I), n1 represents an integer of 3 to 7.

[10] A composition comprising the compound according to any one of [1] to [9].

[11] The composition according to

[10] , further comprising a polymerization initiator.

[12] The composition according to

[10] or

[11] , further comprising a chiral agent.

[13] The composition according to any one of

[10] to

[12] , which has liquid crystal properties.

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

[10] to

[13] .

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

[10] to

[13] .

[16] The optically anisotropic body according to

[15] , which has an alignment pattern in which the direction of the optical axis derived from the compound is continuously rotated along at least one in-plane direction.

[17] An optical element comprising the optical anisotropic body according to

[16] .

[18] A light guide element comprising the optical element according to

[17] and a light guide plate.

[0008] According to the present invention, there is provided a compound which is capable of forming an optically anisotropic layer having a high refractive index (ne) for extraordinary light rays and a high birefringence (Δn) after curing, and which has excellent pattern alignment properties. Furthermore, according to the present invention, there are also provided a composition, a cured product, an optically anisotropic body, an optical element, and a light guide element.

[0009] Fig. 2 is a schematic diagram showing an embodiment of an optically anisotropic layer. Fig. 3 is a schematic plan view of the optically anisotropic layer shown in Fig. 1. Fig. 4 is a conceptual diagram showing the function of the optically anisotropic layer shown in Fig. 2. Fig. 5 is a conceptual diagram showing the function of the optically anisotropic layer shown in Fig. 2. Fig. 6 is a schematic diagram showing another example of an optically anisotropic layer. Fig. 7 is a schematic diagram showing another example of an optically anisotropic layer.

[0010] The present invention will be described in detail below. The following description of the components will be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment. In each drawing, the scale of the components is appropriately different from the actual scale for ease of viewing.

[0011] In addition, in this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​written before and after "to" as the lower and upper limits.

[0012] In this specification, the terms "perpendicular" and "parallel" with respect to angles mean a range of ±10° of the strict angle.

[0013] In this specification, n represents the refractive index, ne represents the refractive index in the slow axis direction, and no represents the refractive index in the fast axis direction. Unless otherwise specified, n, ne, and no represent values ​​at a wavelength of 550 nm. In this specification, n, ne, and no are values ​​measured by ellipsometry.

[0014] In addition, in this specification, the term "(meth)acryloyloxy group" refers to both an acryloyloxy group and a methacryloyloxy group, and the term "(meth)acrylate" refers to both an acrylate and a methacrylate.

[0015] Furthermore, in the description of groups (atomic groups) in this specification, when a notation does not specify whether the group is substituted or unsubstituted, it encompasses both unsubstituted groups and substituted groups. For example, the term "alkyl group" encompasses not only alkyl groups without a substituent (unsubstituted alkyl groups) but also alkyl groups with a substituent (substituted alkyl groups).

[0016] Furthermore, the bonding direction of divalent groups represented in this specification is not limited unless otherwise specified. For example, when Y is -COO- in a compound represented by the formula "X-Y-Z", Y may be -CO-O- or -O-CO-. Furthermore, the compound may be either "X-CO-O-Z" or "X-O-CO-Z".

[0017] Furthermore, in this specification, when simply referring to a "substituent", examples of the substituent include the following substituent L. Furthermore, in this specification, when referring to a "substituent L", the substituent L is intended to mean the following substituent L.

[0018] (Substituent L) Examples of the substituent L include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkanoyl group having 1 to 10 carbon atoms, an alkanoyloxy group having 1 to 10 carbon atoms, an alkanoylamino group having 1 to 10 carbon atoms, an alkanoylthio group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 2 to 10 carbon atoms, an alkylaminocarbonyl group having 2 to 10 carbon atoms, an alkylthiocarbonyl group having 2 to 10 carbon atoms, a hydroxy group, an amino group, a mercapto group, a carboxy group, a sulfo group, an amido group, a cyano group, a nitro group, a halogen atom, an NCS group, SO ２ Examples of the substituent L include an NCS group, an OCN group, a trifluoromethyl group, a halogen atom, and a polymerizable group. ２ When - (methylene group) is contained, -CH contained in the above group ２ The substituent L also includes a group in which at least one of - is replaced with -O-, -CO-, -CH=CH-, or -C≡C-. For example, a group in which the above groups are two or more -CH ２ -, one -CH ２ - is replaced with -O-, and one adjacent -CH ２ - may be replaced with -CO- to form an ester group (-O-CO-). When the above group described as the substituent L has a hydrogen atom, the substituent L also includes a group in which at least one of the hydrogen atoms contained in the above group is replaced with at least one selected from the group consisting of a fluorine atom and a polymerizable group. ２ When at least one of the - is replaced with -O-, -CO-, -CH=CH-, or -C≡C-, the number of carbon atoms after the replacement satisfies the above-mentioned predetermined range. ２When at least one of - is replaced by -O-, -CO-, -CH=CH-, or -C≡C-, the number of carbon atoms in the alkyl group after the replacement is 1 to 10. Furthermore, examples of the polymerizable group include an ethylenically unsaturated group and a ring-polymerizable group, and among these, a substituent selected from the polymerizable group P described below is preferred. As the substituent L, among others, 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 is preferred, 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 is more preferred, and 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 is even more preferred.

[0019] In addition, in this specification, when simply referring to a "polymerizable group", examples of the polymerizable group include polymerizable groups capable of addition polymerization and ring polymerization, such as the polymerizable group P shown below.

[0020] (Polymerizable Group P) Examples of the polymerizable group P include groups represented by any of the following formulae (P-1) to (P-19). In the following formulae, * represents a bonding position, Me represents a methyl group, and Et represents an ethyl group. Of these, formula (P-1) or formula (P-2) ((meth)acryloyloxy group) are preferred.

[0021]

[0022] In this specification, the "solid content" of a composition means the components that form an optically anisotropic layer formed using the composition, and when the composition contains a solvent (organic solvent, water, etc.), it means all components excluding the solvent. Furthermore, liquid components that form an optically anisotropic layer are also considered to be solid contents.

[0023] In this specification, unless otherwise specified, the thickness of a layer is a value obtained by observing a cross section cut by a microtome with a SEM (scanning electron microscope) or a TEM (transmission electron microscope) and measuring the thickness at 10 points, and averaging the thickness.

[0024] [Compound represented by formula (I)] A characteristic feature of the compound represented by formula (I) (hereinafter also referred to as "specific compound") is that it has a polymerizable group and a fused ring structure represented by formula (Ia) described below. An optically anisotropic layer obtained by curing a composition containing the specific compound has a high refractive index ne for extraordinary light rays and a high birefringence Δn. The specific compound also has excellent pattern alignment properties. Although the mechanism of action is not necessarily clear, the inventors speculate as follows.

[0025] The fused ring structure represented by formula (Ia) described below contains a sulfur atom with a large atomic refraction. In addition, the polymerizable group causes cure shrinkage during polymerization, thereby improving the density of the film and further increasing the refractive index. Furthermore, the refractive index of a liquid crystal compound is classified into the refractive index n e in the compound's long axis direction and the refractive index n o in the compound's short axis direction, with n e > n o being generally in the relationship n e > n o. In certain optical systems, in order to maximize the refractive index for polarized light, it is necessary to particularly increase the refractive index n e of the compound's long axis. It is speculated that the presence of a fused ring structure represented by formula (Ia) in a compound improves the liquid crystallinity and degree of orientation of the compound, resulting in a particularly large n e . Furthermore, the inventors have confirmed that polymerization reduces the degree of orientation, and therefore, depending on the structure of the compound, n e may decrease due to polymerization. However, it is speculated that in certain compounds, the high intermolecular forces of the fused ring structure represented by formula (Ia) described below facilitates film densification by polymerization, making n e more likely to increase. It has also been confirmed that the optically anisotropic layer obtained by curing a composition containing the specific compound has a high birefringence Δn, and that the specific compound has excellent pattern alignment properties.

[0026] Hereinafter, the term "better effects of the present invention" refers to an optically anisotropic layer obtained by curing a composition containing a specific compound having a higher refractive index ne for extraordinary light rays, an optically anisotropic layer obtained by curing a composition containing a specific compound having a higher birefringence Δn, and / or better pattern alignment of the specific compound.

[0027] The compound represented by formula (I) (specific compound) will be described in detail below. [Compound represented by formula (I)]

[0028]

[0029] In formula (I), P １ and P ２ each independently represents a hydrogen atom, a polymerizable group, or a monovalent substituent; P １ and P ２ At least one of P is a polymerizable group. １ and P ２ It is preferred that all of the groups are polymerizable groups.

[0030] P １ and P ２ Examples of the polymerizable group represented by the formula (I) include an ethylenically unsaturated group and a ring-polymerizable group, and specific examples thereof include substituents selected from the polymerizable groups P described above.

[0031] P １ and P ２ Examples of the monovalent substituent represented by the formula include the substituent L. As the substituent L, as described above, an alkyl group, an alkoxy group, a cyano group, or an NCS group is preferable, and an NCS group is more preferable.

[0032] L １ and L ２ each independently represents a single bond or an alkylene group having 20 or less carbon atoms, and any —CH ２ - may be replaced by -O-, -S-, -NR-, -CO-, or -CS-, and any -(CH ２ ) ２- may be replaced by -CH=CH- or C≡C-, and any hydrogen atom in the alkylene group may be replaced by a fluorine atom or a chlorine atom. ２ - and - (CH ２ ) ２ When - is replaced, the number of carbon atoms after the replacement satisfies the above-mentioned predetermined numerical range. The alkylene group having 20 or less carbon atoms may be linear, branched, or cyclic, but linear or branched is preferred. The number of carbon atoms in the alkylene group having 20 or less carbon atoms is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 4.

[0033] The R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The number of carbon atoms in the alkyl group represented by the R is preferably 1 to 6, and more preferably 1 to 3. When there are multiple Rs in the formula, the multiple Rs may be the same or different. The R is preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and more preferably a hydrogen atom.

[0034] A １ and A ２ each independently represents a divalent aromatic ring group which may have a substituent, or a divalent alicyclic group which may have a substituent, and n1 A's present in formula (I) １ and A ２ At least one of the rings is a fused ring structure represented by the following formula (Ia): １ and A ２ It is preferable that two or more of the above have a fused ring structure represented by the following formula (Ia).

[0035]

[0036] In formula (Ia), X １ , X ２ , X ３ , and X ４ Two of them represent -C(*)=, and X１ , X ２ , X ３ , and X ４ the other two of which are each independently -N= or -C(R Ａ ) =. R Ａ represents a hydrogen atom or a substituent. * represents a bonding position. In other words, the fused ring structure represented by formula (Ia) corresponds to a divalent linking group having * as a bonding position.

[0037] In formula (Ia), X １ , X ２ , X ３ , and X ４ Two of them represent -C(*)=, and X １ , X ２ , X ３ , and X ４ The other two are -C(R Ａ )=. Ａ Specific examples of the substituent represented by the formula (I) include the substituent L described above. Ａ Among these, a hydrogen atom is preferable as the .

[0038] In formula (Ia), X １ and X ４ represents -C(*)=, or X ２ and X ３ preferably represents -C(*)=, and X １ and X ４ More preferably, represents -C(*)=.

[0039] A １ and A ２ Examples of the divalent aromatic ring group represented by the formula (I) include a divalent aromatic hydrocarbon ring group and a divalent aromatic heterocyclic group. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon ring group may be either a monocyclic or polycyclic ring. The number of carbon atoms in the aromatic hydrocarbon ring group is preferably 6 to 20, and more preferably 6 to 10. Specific examples of the aromatic hydrocarbon ring are preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring.

[0040] The number of ring members in the aromatic heterocycle constituting the divalent aromatic heterocyclic group is preferably 5 to 10, and more preferably 5 or 6. Examples of heteroatoms contained in the aromatic heterocycle include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of carbon atoms in the aromatic heterocycle is preferably 3 to 20, and more preferably 3 to 10. Specific examples of the aromatic heterocycle include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a thiophene ring, a thiazole ring, and an imidazole ring.

[0041] A １ and A ２ The divalent aromatic ring group represented by the formula (I) is preferably a divalent aromatic hydrocarbon ring group, and more preferably a divalent benzene ring group (phenylene group), a divalent thienothiophene ring group, a divalent thienothiazole ring, a divalent thiazolothiazole ring, a divalent benzothiophene ring, or a divalent naphthalene ring group (naphthylene group).

[0042] A １ and A ２ Examples of the divalent alicyclic group represented by the formula (I) include a divalent aliphatic hydrocarbon ring group and a divalent aliphatic heterocyclic group. The aliphatic hydrocarbon ring constituting the divalent aliphatic hydrocarbon ring group may be either a monocyclic or polycyclic ring. The number of ring members in the aliphatic hydrocarbon ring is preferably 3 to 20, more preferably 3 to 10, and even more preferably 5 or 6. Specific examples of the aliphatic hydrocarbon ring include a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a norbornene ring, and an adamantane ring. Of these, a cyclopentane ring or a cyclohexane ring is preferred.

[0043] The aliphatic heterocycle constituting the divalent aliphatic heterocyclic group may be either a monocycle or a polycycle. Examples of heteroatoms contained in the aliphatic heterocycle include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of ring members in the aliphatic heterocycle is not particularly limited, but is preferably 5 to 10. Specific examples of the aliphatic heterocycle include an oxolane ring, an oxane ring, a piperidine ring, and a piperazine ring. The aliphatic heterocycle may be a ring containing -CH ２The - may be substituted with -CO-, such as a phthalimide ring.

[0044] A １ and A ２ The divalent aromatic ring group and the divalent alicyclic group represented by the following formula may have a substituent. Examples of the substituent include the aforementioned substituent L. Furthermore, when the divalent aromatic ring group and the divalent alicyclic group have a plurality of substituents (preferably substituents L), the substituents may form a ring together to form a condensed ring structure.

[0045] A １ and A ２ Among these, a divalent benzene ring group (phenylene group) which may have a substituent L, a divalent benzothiophene ring group which may have a substituent L, or a divalent naphthalene ring group (naphthylene group) which may have a substituent L is preferred, in terms of the effects of the present invention being more excellent.

[0046] In addition, in the formula, A １ If there are multiple A's, １ They may be the same or different from each other.

[0047] Z １ each independently represents a single bond, —O—, —S—, —CHRCHR—, —OCHR—, —CO—, —SO—, or —SO ２ -, -COO-, -CO-S-, -O-CO-O-, -CO-NR-, -SCHR-, -SO-CHR-, -SO ２ -CHR-, -CF ２ O-, -CF ２ S-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO ２ -CHRCHR-SO ２ -, -CH=CH-COO-, -CH=CH-OCO-, -CH=CH-CONR-, -CH=CH-COS-, -COO-CHRCHR-, -OCO-CHRCHR-, -COO-CHR-, -OCO-CHR-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=N-N=CR-, -CF=CF-, -C≡C-C≡C-, -C≡C- or an alkylene group having 10 or less carbon atoms, ２- may be replaced by -O-, -S-, -NR-, -CO-, or -CS-, and any -(CH ２ ) ２ - may be replaced by -CH=CH- or -C≡C-, and any hydrogen atom in the alkylene group may be replaced by a fluorine atom or a chlorine atom. ２ - and - (CH ２ ) ２ When - is substituted, the number of carbon atoms after the substitution satisfies the above-mentioned predetermined range.

[0048] The alkylene group having 10 or less carbon atoms may be linear, branched, or cyclic, and is preferably linear or branched. The number of carbon atoms in the alkylene group having 10 or less carbon atoms is preferably 1 to 6, and more preferably 1 to 3.

[0049] R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. The alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear. The alkyl group represented by R preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. When multiple Rs are present in the formula, the multiple Rs may be the same or different. Of these, a hydrogen atom is preferred as R.

[0050] Z １ Among these, a single bond, —CHRCHR—, —OCHR—, —COO—, —CO—NH—, or —C≡C— is preferable, and —OCH ２ - or -C≡C- is more preferred.

[0051] In addition, Z in the formula １ If there are multiple Z １ In formula (I), Z may be the same or different. １ At least one of these is preferably -C≡C-.

[0052] n1 represents an integer of 1 to 7. In terms of achieving better effects of the present invention, n1 is preferably 1 to 4, and more preferably 2 or 3. In terms of achieving better pattern orientation of the specific compound, n1 is also preferably 3 to 7.

[0053] In formula (I), when n1 is an integer of 2 or more, a plurality of Z １ A of １ Two Zs that are adjacent to each other via １ It is preferable that neither of them is —C≡C—.

[0054] An example where n1 represents 3 will be described. When n1 represents 3, -(A １ -Z １ ) ｎ１ The structural portion represented by - is -A １Ａ -Z １ａ -A １Ｂ -Z １ｂ -A １Ｃ -Z １ｃ - (However, A １Ａ ~A １Ｃ are all A １ is synonymous with Z １ａ ~Z １ｃ are all Z １ In this case, A １Ｂ Z １ａ and Z １ｂ is preferably not simultaneously —C≡C—. That is, for example, Z １ａ When represents -C≡C-, Z １ｂ is Z other than -C≡C- １ (a single bond or the above-mentioned Z １ A is preferably a divalent linking group other than -C≡C- among divalent linking groups represented by the following formula: １Ｃ Z １ｂ and Z １ｃ At the same time, it is also preferable that —C≡C— is not the case.

[0055] In formula (I), when n1 is an integer of 2 or more, a plurality of Z １ A of １Two Zs that are adjacent to each other via １ If both are -C≡C-, then two -C≡C- are linked together. １ In the above embodiment, Z is preferably a structure represented by formula (Ia). １ represents X in formula (Ia) ２ and X ３ It is preferred that the compound is bonded to

[0056] Examples of the specific compound are given below, but the invention is not limited thereto.

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063] The specific compound may or may not have liquid crystallinity, but preferably has liquid crystallinity. Note that, when a compound exhibits liquid crystallinity, it is intended that the compound has the property of exhibiting an intermediate phase between a crystalline phase (low temperature side) and an isotropic phase (high temperature side) when the temperature is changed. As a specific observation method, the optical anisotropy and fluidity derived from the liquid crystal phase can be confirmed by observing the compound under a polarizing microscope while heating or cooling it using a Mettler Toledo hot stage system FP90 or the like.

[0064] [Composition] [Specific Compound] The composition of the present invention contains a compound represented by formula (I) (specific compound). The specific compound is as described above. The content of the specific compound in the composition is not particularly limited, but is, for example, preferably 10 to 100% by mass, more preferably 30 to 99% by mass, and even more preferably 50 to 98% by mass, relative to the total mass of the liquid crystal compound in the composition. The composition may use one specific compound alone, or two or more specific compounds. When two or more specific compounds are used, the total content thereof is preferably within the above range.

[0065] [Liquid Crystal Compound] The composition of the present invention may contain a liquid crystal compound other than the specific compound.

[0066] Generally, liquid crystal compounds can be classified into rod-shaped and discotic types based on their shape. Each of these can further be divided into low-molecular-weight and high-molecular-weight types. A high-molecular-weight compound generally refers to a compound with a degree of polymerization of 100 or more (see "Polymer Physics: Phase Transition Dynamics," by Masao Doi, page 2, Iwanami Shoten, 1992). The liquid crystal compound is not particularly limited, and any compound may be used. Among these, rod-shaped liquid crystal compounds or discotic liquid crystal compounds (discotic liquid crystal compounds) are preferred, with rod-shaped liquid crystal compounds being more preferred, as they provide superior effects of the present invention.

[0067] Furthermore, the liquid crystal compound is preferably a liquid crystal compound having a polymerizable group in the molecule (polymerizable liquid crystal compound). Examples of the polymerizable group include an ethylenically unsaturated group and a ring-polymerizable group, and specific examples include a vinyl group, a styryl group, an allyl group, and a substituent selected from the above-mentioned polymerizable group P. When the liquid crystal compound contains a polymerizable group, the number of polymerizable groups is not particularly limited, but is, for example, one or more. In order to fix the alignment, it is preferable that the liquid crystal compound has two or more polymerizable groups in one molecule. The upper limit is, for example, preferably six or less, more preferably three or less.

[0068] The liquid crystal compound may be used alone or in combination of two or more. When two or more liquid crystal compounds are used in combination, the liquid crystal compound may be in the form of two or more rod-shaped liquid crystal compounds, two or more discotic liquid crystal compounds, or a mixture of a rod-shaped liquid crystal compound and a discotic liquid crystal compound. When two or more liquid crystal compounds are used in combination, it is also preferable that at least one of the liquid crystal compounds is a polymerizable liquid crystal compound.

[0069] As the liquid crystal compound, known compounds can be used. As the rod-shaped liquid crystal compound, for example, compounds described in [Claim 1] of JP-A-11-513019, paragraphs

[0026] to

[0098] of JP-A-2005-289980, WO 2019-182129, and JP-A-2023-003351 can be suitably used. Furthermore, as the discotic liquid crystal compound, for example, compounds described in paragraphs

[0020] to

[0067] of JP-A-2007-108732, and paragraphs

[0013] to

[0108] of JP-A-2010-244038 can be suitably used.

[0070] Examples of rod-shaped liquid crystal compounds include rod-shaped nematic liquid crystal compounds. Preferred rod-shaped nematic liquid crystal compounds include azomethines, azoxys, cyanobiphenyls, cyanophenyl esters, benzoates, cyclohexanecarboxylic acid phenyl esters, cyanophenylcyclohexanes, cyano-substituted phenylpyrimidines, alkoxy-substituted phenylpyrimidines, phenyldioxanes, tolanes, and alkenylcyclohexylbenzonitriles. As the liquid crystal compound, not only low-molecular-weight liquid crystal compounds but also high-molecular-weight liquid crystal compounds can be used.

[0071] The liquid crystal compound preferably has a high refractive index anisotropy Δn, specifically, preferably 0.15 or more, more preferably 0.18 or more, even more preferably 0.22 or more, and particularly preferably 0.25 or more. There is no particular upper limit, but it is often 0.60 or less.

[0072] By using a mixture of the specific compound and the liquid crystal compound, the crystallization temperature as a whole can be significantly lowered.

[0073] As the liquid crystal compound, Makromol. Chem. , Vol. 190, p. 2255 (1989), Advanced Materials Vol. 5, p. 107 (1993), U.S. Pat. No. 4,683,327, U.S. Pat. No. 4,983,479, U.S. Pat. No. 5,622,648, U.S. Pat. No. 5,770,107, WO 95 / 022586, WO 95 / 024455, WO 97 / 000600, WO 98 / 023580, WO 98 / 052905, JP-A-1-272551, WO 6-016616, WO 7-110469, WO 11-080081, and compounds described in JP-A-2001-328973 and the like can be mentioned. When the composition of the present invention contains a liquid crystal compound, the content of the liquid crystal compound in the composition is not particularly limited, but is preferably 0 to 90 mass %, more preferably 0 to 70 mass %, and even more preferably 0 to 50 mass %, relative to the total mass of the solid contents in the composition. The composition of the present invention may use one liquid crystal compound alone, or two or more liquid crystal compounds. When two or more liquid crystal compounds are used, the total content thereof is preferably within the above range.

[0074] [Polymerization initiator] The composition preferably contains a polymerization initiator. The polymerization initiator is preferably a photopolymerization initiator that can initiate a polymerization reaction upon irradiation with ultraviolet light. Examples of photopolymerization initiators include α-carbonyl compounds, acyloin ethers, α-hydrocarbon-substituted aromatic acyloin compounds, polynuclear quinone compounds, phenazine compounds, oxadiazole compounds, and compounds having an oxime ester structure.

[0075] When the composition of the present invention contains a polymerization initiator, the content of the polymerization initiator in the composition is not particularly limited, but is preferably 0.1 to 20 mass %, more preferably 1 to 8 mass %, relative to the total mass of the specific compound (when the composition contains a liquid crystal compound, relative to the total mass of the specific compound and the liquid crystal compound). The composition of the present invention may use one type of polymerization initiator alone, or two or more types. When two or more types are used, it is preferable that the total content thereof is within the above range.

[0076] The composition of the present invention may contain a surfactant that contributes to stable or rapid formation of a liquid crystal phase (e.g., a nematic phase, a cholesteric phase). Examples of the surfactant include fluorine-containing (meth)acrylate polymers, compounds represented by general formulas (X1) to (X3) described in WO 2011 / 162291, compounds represented by general formula (I) described in paragraphs

[0082] to

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

[0020] to

[0031] of JP 2013-047204. Examples of fluorine-containing (meth)acrylate polymers that can be used as surfactants include the polymers described in paragraphs

[0018] to

[0043] of JP 2007-272185. When the composition of the present invention contains a surfactant, the content of the surfactant is not particularly limited, but is preferably 0.001 to 10 mass %, more preferably 0.05 to 3 mass %, relative to the total mass of the specific compound (when the composition contains a liquid crystal compound, relative to the total mass of the specific compound and the liquid crystal compound). The composition of the present invention may use one surfactant alone, or two or more surfactants. When two or more surfactants are used, the total content thereof is preferably within the above range.

[0077] [Chiral Agent] The composition of the present invention may contain a chiral agent. A chiral agent (optically active compound) has the function of inducing a helical structure in a cholesteric liquid crystal phase. The chiral agent may be selected according to the purpose, since the twist direction or helical pitch of the helix induced varies depending on the compound. The type of chiral agent is not particularly limited. The chiral agent may be liquid crystalline or non-liquid crystalline. Chiral agents generally contain an asymmetric carbon atom, but axially asymmetric or planar asymmetric compounds that do not contain an asymmetric carbon atom can also be used as chiral agents. Examples of axially asymmetric or planar asymmetric compounds include binaphthyl, helicene, paracyclophane, and derivatives thereof. The chiral agent may have a polymerizable group.

[0078] When the composition of the present invention contains a chiral agent, the content of the chiral agent in the composition is not particularly limited, but is preferably 0.1 to 15 mass %, more preferably 1.0 to 10 mass %, relative to the total mass of the specific compound (when the composition contains a liquid crystal compound, relative to the total mass of the specific compound and the liquid crystal compound). The composition of the present invention may use one type of chiral agent alone, or two or more types. When two or more types are used, it is preferable that the total content thereof is within the above range.

[0079] [Solvent] The composition of the present invention may contain a solvent. The solvent is preferably one that can dissolve each component blended in the composition of the present invention, and examples thereof include chloroform and methyl ethyl ketone. When the composition of the present invention contains a solvent, the content of the solvent in the composition is preferably an amount that makes the solids concentration of the composition 0.5 to 35 mass %, more preferably an amount that makes 1 to 25 mass %. The composition of the present invention may use one solvent alone, or two or more solvents. When two or more solvents are used, the total content thereof is preferably within the above range.

[0080] [Other Additives] The composition of the present invention may contain additives other than the above-mentioned components, such as antioxidants, ultraviolet absorbers, sensitizers, stabilizers, plasticizers, chain transfer agents, polymerization inhibitors, defoamers, leveling agents, thickeners, flame retardants, dispersants, and coloring materials such as dyes and pigments.

[0081] [Refractive index of composition] The refractive index n of the composition of the present invention is preferably 1.65 or more, more preferably 1.70 or more, and even more preferably 1.75 or more, because the diffraction efficiency of the film obtained is higher.In addition, the refractive index ne of the slow axis direction is preferably 1.80 or more, more preferably 1.90 or more, and even more preferably 2.00 or more.The upper limit is not particularly limited, but for example, is 3.0 or less.

[0082] [Δn of composition] The refractive index anisotropy Δn of the composition of the present invention is preferably 0.20 or more, more preferably 0.25 or more, and most preferably 0.30 or more at a wavelength of 620 nm, in order to increase the diffraction efficiency of the resulting film. The upper limit is not particularly limited, but is, for example, 0.80 or less.

[0083] [Uses of the Composition] The cured product formed from the composition of the present invention can be used as an optically anisotropic body (optically anisotropic layer). The optically anisotropic layer and a method for producing the same will be described below.

[0084] <<Example of Embodiment of Optically Anisotropic Layer>> An example of an embodiment of an optically anisotropic layer comprising a cured layer of the above-described composition will be described with reference to the drawings. Figures 1 and 2 show schematic cross-sectional views of an optically anisotropic layer 1. Figure 1 is a side view schematically showing the optically anisotropic layer 1, and Figure 2 is a plan view schematically showing the liquid crystal alignment pattern of the optically anisotropic layer 1 shown in Figure 1. In the drawings, the sheet surface of the sheet-like optically anisotropic layer 1 is defined as the xy plane, and the thickness direction is defined as the z direction.

[0085] As shown in FIG. 1 , the optically anisotropic layer 1 has a liquid crystal orientation pattern (length of one period Λ) in which the direction of the optical axis derived from the liquid crystal compound 30 is continuously rotated along at least one in-plane direction. Note that in FIGS. 1 to 4 , in order to simplify the drawings and clearly show the configuration of the optically anisotropic layer 1, only the liquid crystal molecules present on one main surface of the optically anisotropic layer 1 are shown. However, the optically anisotropic layer 1 has a structure in which aligned liquid crystal compounds 30 are stacked, similar to an optically anisotropic layer formed using a composition containing a typical liquid crystal compound. Typically, when the in-plane retardation value of the optically anisotropic layer 1 is set to λ / 2, the optically anisotropic layer 1 functions as a typical λ / 2 plate, that is, imparts a phase difference of half the wavelength, i.e., 180°, to two orthogonal linearly polarized components contained in light incident on the optically anisotropic layer.

[0086] As shown in Fig. 2, the optically anisotropic layer 1 has a liquid crystal orientation pattern in which the direction of the optical axis 30A (hereinafter sometimes abbreviated as "optical axis 30A") derived from the liquid crystal compound 30 changes while continuously rotating in one direction within the plane of the optically anisotropic layer 1. Herein, the one direction in which the optical axis 30A changes rotationally coincides with the direction of the x-axis in the xy plane. In the following description, the one direction in which the optical axis 30A changes rotationally is referred to as the x-direction.

[0087] The optical axis 30A derived from the liquid crystal compound 30 is the axis along which the refractive index of the liquid crystal compound 30 is highest, that is, the so-called slow axis. As shown in Fig. 1, when the liquid crystal compound 30 is a rod-shaped liquid crystal compound, the optical axis 30A is aligned with the long axis direction of the rod shape.

[0088] The phrase "the orientation of the optical axis 30A changes while continuously rotating in the x direction" specifically means that the angle formed between the optical axis 30A of the liquid crystal compound 30 aligned along the x direction and the x direction varies depending on the position in the x direction, and the angle formed between the optical axis 30A and the x direction gradually changes along the x direction from θ to θ+180° or θ−180°. Here, "the angle gradually changes" may mean that the angle changes at regular angular intervals or that the angle changes continuously. However, the difference in angle between the optical axes 30A of the liquid crystal compounds 30 adjacent to each other in the x direction is preferably 45° or less, more preferably 15° or less, and even more preferably a smaller angle.

[0089] On the other hand, the liquid crystal compounds 30 forming the optically anisotropic layer 1 are arranged at equal intervals in the y direction perpendicular to the x direction in the plane, i.e., in the y direction perpendicular to the one direction (x direction) in which the optical axis 30A continuously rotates. In other words, among the liquid crystal compounds 30 forming the optically anisotropic layer 1, the liquid crystal compounds 30 aligned in the y direction have the same angle between the direction of the optical axis 30A and the x direction. In the optically anisotropic layer 1, in the liquid crystal orientation pattern of such liquid crystal compounds 30, the length (distance) over which the optical axis 30A of the liquid crystal compound 30 rotates 180° in the x direction in which the orientation of the optical axis 30A continuously rotates and changes in the plane is defined as the length Λ of one period of the liquid crystal orientation pattern. In other words, the length of one period of the liquid crystal orientation pattern is defined as the distance from θ to θ+180°, where θ is the angle between the optical axis 30A of the liquid crystal compound 30 and the x direction. 2, the distance between the centers in the x direction of two liquid crystal compounds 30 whose optical axes 30A coincide with the x direction is defined as the length of one period Λ (hereinafter, also referred to as "one period Λ" or "period Λ"). The liquid crystal alignment pattern of the optically anisotropic layer 1 is a pattern in which the liquid crystal alignment of this one period Λ is repeated in the x direction.

[0090] As described above, in the optically anisotropic layer 1, the angle between the optical axis 30A of each liquid crystal compound 30 aligned in the y direction and the x direction, along which the optical axis of the liquid crystal compound 30 rotates, is equal. A region in which the liquid crystal compounds 30, each with the same angle between the optical axis 30A and the x direction, are arranged in the y direction, is referred to as region R. In this case, the in-plane retardation (Re) value in each region R is preferably half the wavelength of the light to be diffracted by the optically anisotropic layer (hereinafter referred to as "target light"), i.e., when the wavelength of the target light is λ, the in-plane retardation Re is λ / 2. These in-plane retardations are calculated by the product of the refractive index anisotropy Δn of region R and the thickness (film thickness) d of the optically anisotropic layer. Here, the refractive index difference associated with the refractive index anisotropy of region R in the optically anisotropic layer is a refractive index difference defined by the difference between the refractive index in the direction of the slow axis in the plane of region R and the refractive index in the direction perpendicular to the slow axis. That is, the refractive index difference Δn due to the refractive index anisotropy of region R is equal to the difference between the refractive index of liquid crystal compound 30 in the direction of optical axis 30A and the refractive index of liquid crystal compound 30 in the direction perpendicular to optical axis 30A in the plane of region R. In other words, the refractive index difference Δn depends on the liquid crystal compound, and the in-plane retardation of each region R is approximately equal. However, as described above, the direction of optical axis 30A differs between each region R.

[0091] In the optically anisotropic layer 1, since the direction of the optical axis 30A is rotated in the plane, it is difficult to measure the in-plane retardation of the entire layer. However, the in-plane retardation of the optically anisotropic layer 1 can be estimated from the period and the diffraction efficiency.

[0092] When circularly polarized light is incident on such an optically anisotropic layer 1, the light is refracted and the direction of the circularly polarized light is changed. This action is conceptually shown in FIG. 3, exemplifying the optically anisotropic layer 1. It is assumed that the in-plane retardation of the optically anisotropic layer 1 is λ / 2. In this case, as shown in FIG. 3, left-handed circularly polarized light P Ｌ The incident light L １ When incident, the incident light L １ is given a phase difference of 180° by passing through the optically anisotropic layer 1, and becomes the transmitted light L ２ is right-handed circularly polarized light PＲ In addition, the incident light L １ When passing through the optically anisotropic layer 1, the absolute phase of the incident light L changes depending on the direction of the optical axis 30A of each liquid crystal compound 30. At this time, the direction of the optical axis 30A changes while rotating along the x direction. １ Furthermore, since the liquid crystal orientation pattern formed in the optically anisotropic layer 1 is a periodic pattern in the x direction, the amount of change in the absolute phase of the incident light L １ 3, a periodic absolute phase Q1 is given to the transmitted light L in the x direction corresponding to the direction of each optical axis 30A. As a result, an equiphase surface E1 tilted in the opposite direction to the x direction is formed. ２ is refracted so as to be inclined toward a direction perpendicular to the equiphase surface E1, and the incident light L １ In this way, left-handed circularly polarized light P Ｌ Incident light L １ is a right-handed circularly polarized light P that is tilted at a certain angle in the x direction with respect to the incident direction. Ｒ Transmitted light L ２ is converted to

[0093] On the other hand, as conceptually shown in FIG. 4, right-handed circularly polarized light P Ｒ Incident light L ４ When incident, the incident light L ４ is given a phase difference of 180° by passing through the optically anisotropic layer 1, and becomes left-handed circularly polarized light P Ｌ Transmitted light L ５ In addition, the incident light L ４ When passing through the optically anisotropic layer 1, the absolute phase of the incident light L changes depending on the direction of the optical axis 30A of each liquid crystal compound 30. At this time, the direction of the optical axis 30A changes while rotating along the x direction. ４ Furthermore, since the liquid crystal orientation pattern formed in the optically anisotropic layer 1 is a periodic pattern in the x direction, the amount of change in the absolute phase of the incident light L ４As shown in FIG. 4, the incident light L is given a periodic absolute phase Q2 in the x direction corresponding to the direction of each optical axis 30A. ４ is right-handed circularly polarized light P Ｒ Therefore, the periodic absolute phase Q2 in the x direction corresponding to the direction of the optical axis 30A is P Ｌ An incident light L １ As a result, the incident light L ４ Now, the incident light L １ Conversely, an equiphase surface E2 inclined in the x direction is formed. ４ is refracted so as to be inclined toward a direction perpendicular to the equiphase surface E2, and the incident light L ４ In this way, the incident light L ４ is the transmitted light L of left-handed circularly polarized light that is tilted at a certain angle in the direction opposite to the x-direction with respect to the incident direction. ５ is converted to

[0094] As described above, the in-plane retardation value of the optically anisotropic layer 1 is preferably half the wavelength of the target light. This is because the closer the in-plane retardation value is to half the wavelength of the target light, the higher the diffraction efficiency can be obtained in diffracting the target light. The in-plane retardation Re(λ) of the optically anisotropic layer for incident light with a wavelength of λ nm in the x direction is expressed as follows: λ ×d is preferably within the range defined by the following formula and can be set appropriately: 0.7 × (λ / 2) nm≦Δn λ ×d≦1.3×(λ / 2)nm

[0095] Here, by changing one period Λ of the liquid crystal alignment pattern formed in the optically anisotropic layer 1, the transmitted light L ２ and L ５ Specifically, the shorter the period Λ of the liquid crystal alignment pattern, the stronger the interference between the lights passing through the adjacent liquid crystal compounds 30, and therefore the angle of refraction of the transmitted light L ２ and L ５Furthermore, by reversing the rotation direction of the optical axis 30A of the liquid crystal compound 30, which rotates along the x direction, the direction of refraction of transmitted light can be reversed. The period Λ is preferably 50 μm or less, more preferably 25 μm or less, and even more preferably 5 μm or less.

[0096] The thickness d of the optically anisotropic layer 1 may be appropriately set to obtain the desired in-plane retardation, but is preferably 1 μm or less, more preferably 0.8 μm or less, and even more preferably 0.5 μm or less. In particular, when the optically anisotropic layer 1 is used as a birefringent mask to form a photo-alignment pattern, the smaller the thickness d, the more preferable. The smaller the thickness d, the more accurately the photo-alignment pattern can be formed. Note that the ratio Λ / d of the period Λ to the thickness d of the optically anisotropic layer is preferably 1 or more.

[0097] The period Λ of the liquid crystal alignment pattern in the optically anisotropic layer 1 can be determined from the period of light and dark by observing a light-dark periodic pattern of light and dark areas under crossed Nicols conditions using a polarizing microscope. The period Λ of the liquid crystal alignment pattern corresponds to twice the period of the observed light-dark periodic pattern. The thickness d of the optically anisotropic layer 1 can be measured, for example, by observing a cross section of the optically anisotropic layer using a scanning electron microscope.

[0098] The optically anisotropic layer 1 preferably has a refractive index anisotropy Δn of 0.21 or more at a wavelength of 550 nm. There is no particular upper limit, but it is preferably 0.8 or less.

[0099] It is also preferable to make the optically anisotropic layer substantially broadband with respect to the wavelength of incident light by adding a twist component to the composition or by laminating different retardation layers. For example, JP 2014-089476 A and the like disclose a method for realizing a broadband patterned λ / 2 plate by laminating two layers of liquid crystals with different twist directions in an optically anisotropic layer, and this method can be suitably used in the optically anisotropic layer of the present invention.

[0100] <Method of Producing Optically Anisotropic Layer 1> A specific example of a method of producing the optically anisotropic layer 1 includes a step X of contacting a substrate provided with an alignment film having a predetermined alignment pattern with a composition to form a composition layer on the alignment film on the substrate, and a step Y of subjecting the composition layer to a heat treatment to align the liquid crystal compound, followed by a curing treatment. After producing the optically anisotropic layer 1, the substrate may or may not be removed from the optically anisotropic layer. Similarly, after producing the optically anisotropic layer 1, the alignment film may or may not be removed from the optically anisotropic layer.

[0101] The specific procedures of Step X and Step Y are described in detail below. (Step X) Substrate The type of substrate used in Step X is not particularly limited, and examples thereof include known substrates (for example, resin substrates, glass substrates, ceramic substrates, semiconductor substrates, and metal substrates).

[0102] Alignment film An alignment film is disposed on the substrate. The presence of the alignment film facilitates orienting the liquid crystal compound 30 in a predetermined liquid crystal alignment pattern during the preparation of the optically anisotropic layer 1. As described above, the optically anisotropic layer 1 has a liquid crystal alignment pattern in which the direction of the optical axis 30A (see FIG. 2) derived from the liquid crystal compound 30 changes while continuously rotating along one in-plane direction (x direction). Therefore, the alignment film is formed so that the optically anisotropic layer can form this liquid crystal alignment pattern.

[0103] Various known alignment films can be used, including, for example, a rubbed film made of an organic compound such as a polymer, an obliquely evaporated film of an inorganic compound, a film having microgrooves, and a film obtained by accumulating LB (Langmuir-Blodgett) films made of organic compounds such as ω-tricosanoic acid, dioctadecylmethylammonium chloride, and methyl stearate by the Langmuir-Blodgett method.

[0104] An alignment film formed by rubbing treatment can be formed by rubbing the surface of the polymer layer several times in a certain direction with paper or cloth. Suitable materials for the alignment film include polyimide, polyvinyl alcohol, polymers having polymerizable groups as described in JP-A-9-152509, and materials used to form alignment films as described in JP-A-2005-097377, JP-A-2005-099228, and JP-A-2005-128503.

[0105] As the alignment film, a so-called photo-alignment film can be suitably used, which is formed by irradiating a photo-alignment material with polarized or non-polarized light. When irradiating with polarized light to form an alignment film, the photo-alignment material can be irradiated from a vertical direction or an oblique direction to form the alignment film, and when irradiating with non-polarized light to form an alignment film, the photo-alignment material can be irradiated from an oblique direction to form the alignment film. Examples of photo-alignment materials used for the photo-alignment film include those described in JP 2006-285197 A, JP 2007-076839 A, JP 2007-138138 A, JP 2007-094071 A, JP 2007-121721 A, JP 2007-140465 A, JP 2007-156439 A, and JP 2007-1 azo compounds described in JP-A-33184, JP-A-2009-109831, JP-A-3883848, and JP-A-4151746, aromatic ester compounds described in JP-A-2002-229039, and maleimides having photo-alignable units described in JP-A-2002-265541 and JP-A-2002-317013. and / or alkenyl-substituted nadimide compounds, photocrosslinkable silane derivatives described in Japanese Patent Nos. 4205195 and 4205198, photocrosslinkable polyimides, photocrosslinkable polyamides, and photocrosslinkable esters described in JP-T-2003-520878, JP-T-2004-529220, and JP-T-4162850, and photodimerizable compounds described in JP-A-9-118717, JP-A-10-506420, JP-A-2003-505561, WO 2010 / 150748, JP-A-2013-177561, and JP-A-2014-012823, particularly cinnamate compounds, chalcone compounds, and coumarin compounds. Among these, azo compounds, photocrosslinkable polyimides, photocrosslinkable polyamides, photocrosslinkable esters, cinnamate compounds, chalcone compounds, and the like can be suitably used.

[0106] There is no limitation on the thickness of the alignment film, and the thickness may be appropriately set to obtain the required alignment function depending on the material from which the alignment film is formed.

[0107] The thickness of the alignment film is preferably 0.01 to 5 μm, more preferably 0.05 to 2 μm.

[0108] The method for forming the alignment film is not particularly limited, and various known methods can be used depending on the material for forming the alignment film. A photo-alignment film formed by irradiating a photo-alignment material with polarized or non-polarized light is preferred, as this makes it easier to form an alignment pattern in the optically anisotropic layer 1. The methods described in paragraphs

[0078] to

[0080] of WO 2020 / 022496 and the like can be suitably applied.

[0109] - Procedure of Step X The method of bringing a substrate provided with an alignment film having a predetermined alignment pattern (hereinafter also referred to as "alignment film-attached substrate") into contact with the composition is not particularly limited, and examples thereof include a method of applying the composition onto the alignment film on the substrate, and a method of immersing the above-mentioned alignment film-attached substrate in the composition. Note that after bringing the alignment film-attached substrate into contact with the composition, a drying treatment may be carried out, if necessary, to remove the solvent from the composition layer arranged on the alignment film on the substrate.

[0110] (Step Y) Step Y is a step of subjecting the composition layer to a heat treatment to align the liquid crystal compound, followed by a curing treatment. By subjecting the composition layer to a heat treatment, the liquid crystal compound is oriented to form a liquid crystal phase. For example, when the composition layer contains a chiral agent, a cholesteric liquid crystal phase is formed. The conditions for the heat treatment are not particularly limited, and optimal conditions are selected depending on the type of liquid crystal compound. The curing method is not particularly limited, and examples include photocuring and heat curing. Among these, photoirradiation is preferred, and ultraviolet irradiation is more preferred. For ultraviolet irradiation, a light source such as an ultraviolet lamp is used. The cured product obtained by the above treatment corresponds to a layer formed by fixing a liquid crystal phase. In particular, when the composition contains a chiral agent, a layer formed by fixing a cholesteric liquid crystal phase is formed. Note that these layers no longer need to exhibit liquid crystallinity. More specifically, for example, the state in which the cholesteric liquid crystal phase is "fixed" is the most typical and preferred embodiment in which the orientation of the liquid crystal compound in the cholesteric liquid crystal phase is maintained. More specifically, it is preferable that the layer has no fluidity and can stably maintain the fixed orientation state without causing any change in the orientation state due to an external field or external force, usually in a temperature range of 0 to 50°C, or under more severe conditions in a temperature range of −30 to 70°C.

[0111] <<Modifications of Optically Anisotropic Layer>> The optically anisotropic layer 2 shown in FIG. 5 is an optically anisotropic layer in which liquid crystal compounds 30 are cholesterically aligned in the thickness direction.

[0112] It is known that cholesteric liquid crystal phases exhibit selective reflectivity at specific wavelengths. The central wavelength of selective reflection (selective reflection central wavelength) λ depends on the pitch P (= helical period) of the helical structure in the cholesteric liquid crystal phase, and follows the relationship λ = n × P with the average refractive index n of the cholesteric liquid crystal phase. Therefore, the selective reflection central wavelength can be adjusted by adjusting the pitch of this helical structure.

[0113] Cholesteric liquid crystal phases exhibit selective reflection for either left- or right-handed circularly polarized light at a specific wavelength. Whether the reflected light is right-handed or left-handed circularly polarized depends on the twist direction (sense) of the helix of the cholesteric liquid crystal phase. When the twist direction of the helix of the cholesteric liquid crystal phase is right-handed, right-handed circularly polarized light is reflected, and when the twist direction of the helix is ​​left-handed, left-handed circularly polarized light is reflected.

[0114] Furthermore, the half-width Δλ (nm) of the selective reflection band (circularly polarized light reflection band) exhibiting selective reflection depends on Δn of the cholesteric liquid crystal phase and the helical pitch P, and follows the relationship Δλ = Δn × P. Therefore, the width of the selective reflection band can be controlled by adjusting Δn.

[0115] That is, the optically anisotropic layer 2 has the function of selectively reflecting light of a specific circularly polarized light (right-handed or left-handed circularly polarized light) in a predetermined wavelength range.

[0116] On the other hand, the orientation pattern of the optic axis 30A in the in-plane direction of the optically anisotropic layer 2 is the same as the orientation pattern in the optically anisotropic layer 1 shown in Fig. 1, and therefore exhibits the same effect as the optically anisotropic layer 1. That is, the optically anisotropic layer 2 exhibits the effect of changing the absolute phase of incident light and bending it in a predetermined direction, similar to the above-mentioned optically anisotropic layer 1. Therefore, the optically anisotropic layer 2 has both the effect of bending incident light in a direction different from the incident direction and the effect of the above-mentioned cholesteric orientation, and reflects light at a predetermined angle relative to the reflection direction of specular reflection.

[0117] For example, if the cholesteric liquid crystal phase of the optically anisotropic layer 2 is designed to reflect right-handed circularly polarized light, as shown in FIG. Ｒ Light L ６ When the light is incident, the reflected light L ７ That is, the optically anisotropic layer 2 functions as a reflective diffraction grating.

[0118] 1 to 5, the optical axis 30A of the liquid crystal compound 30 rotates continuously in-plane along only the x-direction. However, in the optically anisotropic layer of the present invention, various configurations can be used as long as the optical axis 30A of the liquid crystal compound 30 rotates continuously along one direction.

[0119] Fig. 6 is a schematic plan view of an optically anisotropic layer 3 of a modified design. In Fig. 6, the liquid crystal orientation pattern is represented by the optical axis 30A of the liquid crystal compound. The optically anisotropic layer 3 has a liquid crystal orientation pattern in which regions in which the direction of the optical axis 30A is the same are arranged concentrically, and one direction in which the direction of the optical axis 30A changes while continuously rotating is arranged radially from the center of the optically anisotropic layer 3. In the optically anisotropic layer 3, the direction of the optical axis 30A is arranged in a number of directions from the center of the optically anisotropic layer 3 outward, for example, in the directions indicated by arrows A １ The direction indicated by arrow A ２ The direction indicated by arrow A ３ The circularly polarized light changes while continuously rotating along the direction indicated by the arrows. The absolute phase of the circularly polarized light incident on the optically anisotropic layer 3 having this liquid crystal orientation pattern changes in each local region where the optical axis of the liquid crystal compound 30 has a different orientation. At this time, the amount of change in each absolute phase differs depending on the orientation of the optical axis of the liquid crystal compound 30 into which the circularly polarized light is incident.

[0120] The optically anisotropic layer 3 having such a concentric liquid crystal orientation pattern, i.e., a liquid crystal orientation pattern in which the optical axis changes by continuous rotation in a radial direction, can transmit incident light as divergent or convergent light depending on the rotation direction of the optical axis of the liquid crystal compound 30 and the direction of the incident circularly polarized light. That is, by making the liquid crystal orientation pattern of the optically anisotropic layer concentric, the optically anisotropic layer can function as, for example, a convex lens or a concave lens.

[0121] Here, when the liquid crystal orientation pattern of the optically anisotropic layer is concentric and the optically anisotropic layer is made to function as a convex lens, it is preferable to gradually shorten one period Λ, in which the optical axis rotates by 180°, from the center of the optically anisotropic layer 3 toward the outside in one direction in which the optical axis continuously rotates. The angle of refraction of light with respect to the incident direction increases as one period Λ of the liquid crystal orientation pattern becomes shorter. Therefore, by gradually shortening one period Λ of the liquid crystal orientation pattern from the center of the optically anisotropic layer 3 toward the outside in one direction in which the optical axis continuously rotates, the light focusing power of the optically anisotropic layer 3 can be further improved, and the performance as a convex lens can be improved.

[0122] Furthermore, depending on the application of the laminate, for example, when forming a concave lens, it is preferable to rotate one period Λ, in which the optical axis in the liquid crystal orientation pattern rotates by 180°, from the center of the optically anisotropic layer 3 in the opposite direction to the direction in which the optical axis continuously rotates, and gradually shorten the period Λ from the center of the optically anisotropic layer 3 toward the outside in one direction. The angle of refraction of light with respect to the incident direction increases as one period Λ in the liquid crystal orientation pattern becomes shorter. Therefore, by gradually shortening one period Λ in the liquid crystal orientation pattern from the center of the optically anisotropic layer 3 toward the outside in one direction in which the optical axis continuously rotates, the light divergence power of the optically anisotropic layer 3 can be further improved, and the performance as a concave lens can be improved.

[0123] For example, when the optically anisotropic layer is used as a concave lens, it is also preferable to reverse the rotation direction of the incident circularly polarized light.

[0124] Conversely, one period Λ of the concentric liquid crystal orientation pattern may be gradually lengthened from the center of the optically anisotropic layer 3 outward in one direction in which the optical axis continuously rotates. Furthermore, depending on the application of the optically anisotropic layer, for example, when it is desired to provide a light intensity distribution in transmitted light, it is also possible to use a configuration in which the period Λ is not gradually changed in one direction in which the optical axis continuously rotates, but has regions in which the period Λ is partially different in one direction in which the optical axis continuously rotates. In addition, the light-emitting element may have an optically anisotropic layer in which the period Λ is uniform throughout and an optically anisotropic layer having regions in which the period Λ is different.

[0125] In this way, the configuration in which the period Λ of the optical axis, which rotates 180°, is changed in one direction in which the optical axis continuously rotates, can also be used in the configurations shown in Figures 1 to 4 in which the optical axis 30A of the liquid crystal compound 30 continuously rotates and changes only in one direction, the x direction. For example, by gradually shortening the period Λ of the liquid crystal orientation pattern in the x direction, an optically anisotropic layer that transmits light in a condensing manner can be obtained. Furthermore, by reversing the direction in which the optical axis rotates 180° in the liquid crystal orientation pattern, an optically anisotropic layer that transmits light in a diffusive manner only in the x direction can be obtained. Note that an optically anisotropic layer that transmits light in a diffusive manner only in the X direction indicated by the arrow can also be obtained by reversing the rotation direction of incident circularly polarized light. Furthermore, depending on the application of the optically anisotropic layer, for example, when it is desired to provide a light intensity distribution in the transmitted light, a configuration in which the period Λ is partially different in the x direction rather than gradually changing the period Λ in the x direction can also be used.

[0126] [Optical Element] The optical element of the present invention has the above-mentioned optically anisotropic layer (optically anisotropic body). The use of the optical element is not particularly limited, and it can be used for various uses that transmit light in a direction different from the incident direction, such as a light path changing element in an optical device, a light concentrating element, a light diffusing element in a predetermined direction, and a diffraction element. Among these, a preferred use is a light guide element. The light guide element typically includes a light guide plate and a diffraction element arranged on the light guide plate (preferably arranged at a distance from the light guide plate). The optical element of the present invention is suitably used as a diffraction element.

[0127] The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the examples shown below. The abbreviations used in the following explanation are as follows: DMAc: dimethylacetamide THF: tetrahydrofuran MeOH: methanol DMF: N,N-dimethylformamide

[0128] [Synthesis of specific compounds] <Synthesis Example 1: Synthesis of compound A-1> Compound A-1 was synthesized according to the following scheme. Compound 7 was synthesized according to WO 2019 / 182129. TMS represents a trimethylsilyl group (—Si(CH ３ ) ３ ) represents

[0129]

[0130] (1) Synthesis of Compound 4 Thieno[2,3-b]thiophene (Compound 1: 6.0 g, 42.8 mmol) was dissolved in DMF (60.0 mL) and cooled to 0°C. Subsequently, N-bromosuccinimide (7.62 g, 42.8 mmol) was added, and the mixture was warmed to room temperature and stirred for 1 hour. Dichloromethane (120 mL) and water (60 mL) were added, and the mixture was stirred, after which the aqueous layer was removed. The resulting organic layer was washed successively with a 1 M aqueous lithium chloride solution, water, and brine, and then dried over magnesium sulfate. The organic layer was filtered, and the solvent was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to obtain Compound 2.

[0131] Under a nitrogen atmosphere, DMF (40.3 mL) was cooled to 0°C. Subsequently, phosphorus oxychloride (36.1 mL) was added dropwise, and the mixture was stirred for 1 hour. A solution of compound 2 in 1,2-dichloroethane (57.2 mL) was added dropwise, and the temperature was raised to 90°C. After stirring for 5 hours, the reaction solution was added to water (400 mL) at 0°C. A 50% aqueous solution of sodium hydroxide was added until the pH reached 7.0, and then the mixture was extracted with dichloromethane. The obtained organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by flash column chromatography to obtain compound 3.

[0132] Under a nitrogen atmosphere, sodium borohydride (1.34 g, 35.5 mmol) was added to isopropanol (101 mL). Subsequently, a solution of compound 3 in THF (53.8 mL) was added dropwise, followed by stirring for 1 hour. After cooling to 0°C, 2N hydrochloric acid and dichloromethane were added and stirred, and the aqueous layer was removed. The resulting organic layer was washed sequentially with aqueous sodium bicarbonate and brine, and then dried over magnesium sulfate. After filtering the organic layer, the solvent was evaporated under reduced pressure to obtain compound 4 (8.0 g, three-step yield: 75.0%).

[0133] (2) Synthesis of Compound 5 Under a nitrogen atmosphere, compound 4 (8.00 g, 20.4 mmol) was dissolved in DMAc (80 mL), and N,N-diisopropylethylamine (11.4 mL) and trimethylsilylacetylene (4.04 mL, 28.6 mmol) were added. Subsequently, bis(benzonitrile)palladium(II) dichloride (297 mg), tri-tert-butylphosphonium tetrafluoroborate (432 mg), and copper iodide (190 mg) were added, followed by stirring at 60°C for 3 hours. The resulting solution was cooled to room temperature, and ethyl acetate (60 mL) was added. Subsequently, the mixture was washed sequentially with hydrochloric acid, water, and brine. The resulting organic layer was dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain compound 5 (6.48 g, yield: 74.1%).

[0134] (3) Synthesis of Compound 6 Compound 5 (6.48 g, 24.3 mmol) and acetic acid (1.53 mL, 26.8 mmol) were dissolved in THF (32.4 mL), and a 1 mol / L THF solution of tetra-n-butylammonium fluoride (TBAF) (26.8 mL, 26.8 mmol) was added dropwise under ice cooling. After stirring at room temperature for 1 hour, ethyl acetate (48.6 mL) was added, and the mixture was washed sequentially with hydrochloric acid, aqueous sodium bicarbonate, and brine. The resulting organic layer was dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to give compound 6 (3.12 g, yield: 66.0%).

[0135] (4) Synthesis of Compound 8 Under a nitrogen atmosphere, compound 7 (1.5 g, 3.04 mmol) was dissolved in DMF (15.0 mL), and triethylamine (4.23 mL), triphenylphosphine (60 mg), and tetrabutylammonium bromide (98 mg) were added. Subsequently, bis(triphenylphosphine)palladium(II) dichloride (43 mg) and copper iodide (43 mg) were added, followed by compound 6 (1.77 g, 9.11 mmol), and the mixture was stirred at 60 °C for 2 hours. The resulting solution was cooled to room temperature, and ethyl acetate and THF were added and stirred. The resulting organic layer was washed sequentially with hydrochloric acid, sodium bicarbonate water, and brine. The resulting organic layer was dried over magnesium sulfate, and the organic layer was filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography and then crystallized from THF and MeOH to obtain compound 8 (1.80 g, yield: 94.6%).

[0136] (5) Synthesis of Compound A-1 Compound 8 (1.80 g, 2.87 mmol) was dissolved in DMAc (30.6 mL), and acryloyl chloride (1.39 mL, 17.2 mmol) was added dropwise thereto, followed by stirring at room temperature for 2 hours. Chloroform was added thereto and stirred, after which the aqueous layer was removed. The resulting organic layer was washed successively with water, sodium bicarbonate water, and brine. The resulting organic layer was dried over sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography. The resulting compound was crystallized from THF and MeOH to obtain Compound A-1 (2.01 g, yield: 95.2%). １ H-NMR (CDCl ３ ): δ=3.93 (s, 3H), 5.23 (s, 2H), 5.38 (s, 4H), 5.88 (dd, 2H), 6.15 (dd, 2H), 6.47 (d, 2H), 6. 99 (d, 1H), 7.24 (d, 2H), 7.35 (d, 2H), 7.49 (d, 2H), 7.56 (d, 2H), 7.59 (dd, 1H), 8.03 (d, 1H)

[0137] Synthesis Example 2: Synthesis of Compound A-2 Compound A-2 was synthesized according to the following scheme. Compound 10 was synthesized according to WO 2019 / 182129. TMS represents a trimethylsilyl group (—Si(CH ３ )３ ) represents

[0138]

[0139] (1) Synthesis of Compound 9 Compound 1 (1.00 g, 7.13 mmol) was dissolved in DMF (10.0 mL) and cooled to 0°C. N-iodosuccinimide (NIS, 2.6 g, 14.6 mmol) was added, and the mixture was heated to 80°C and stirred for 5 hours. Water (10 mL) and dichloromethane (10 mL) were added, and the mixture was stirred, after which the aqueous layer was removed. The resulting organic layer was washed sequentially with a 1M aqueous lithium chloride solution, water, and brine. The resulting organic layer was dried over sodium sulfate, and the organic layer was filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography. Compound 9 (2.18 g, yield: 78.0%) was obtained.

[0140] (2) Synthesis of Compound 11 Under a nitrogen atmosphere, compound 9 (1.00 g, 2.55 mmol) and compound 10 (0.82 g, 5.61 mmol) were dissolved in DMAc (10.0 mL), and N,N-diisopropylethylamine (1.43 mL) was added. Subsequently, bis(benzonitrile)palladium(II) dichloride (37 mg), tri-tert-butylphosphonium tetrafluoroborate (54 mg), and copper iodide (24 mg) were added, and the mixture was stirred at 60°C for 4 hours. The resulting solution was cooled to room temperature, and ethyl acetate (10 mL) and THF (10 mL) were added. Subsequently, the mixture was washed sequentially with hydrochloric acid, water, and brine. The resulting organic layer was dried over magnesium sulfate, and the organic layer was filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain compound 11 (0.59 g, yield: 54.0%).

[0141] (3) Synthesis of Compound A-2 Compound 11 (0.10 g, 0.23 mmol) was dissolved in DMAc (1.7 mL), and acryloyl chloride (0.11 mL, 1.40 mmol) was added dropwise, followed by stirring at room temperature for 2 hours. Chloroform (6.5 mL) was added, and the mixture was washed successively with water, sodium bicarbonate water, and brine. The resulting organic layer was dried over sodium sulfate, and the organic layer was filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography. The resulting compound was crystallized from THF and MeOH to obtain Compound A-2 (0.11 g, yield: 87.8%). １ H-NMR (CDCl ３ ): δ = 3.01 (dd, 4H), 4.39 (dd, 4H), 5.84 (dd, 2H), 6.11 (dd, 2H), 6.39 (dd, 2H), 7.24 (d, 4H), 7.35 (s, 2H), 7.48 (d, 4H)

[0142] Synthesis Example 3: Synthesis of Compound A-3 Compound A-3 was synthesized according to the following scheme: A-3 was synthesized in the same manner as in (1) to (5) of Synthesis Example 1: Synthesis of Compound A-1, except that compound 14 was used.

[0143]

[0144] (1) Synthesis of Compound 14 4-iodo-2,6-dimethylphenol (compound 12: 3.00 g, 12.1 mmol), 4-iodobenzyl bromide (compound 13: 3.68 g, 12.1 mmol), potassium carbonate (1.92 g, 13.9 mmol), and potassium iodide (0.20 g, 1.21 mmol) were dissolved in DMAc (15.0 mL) and stirred at 45°C for 30 minutes, and then at 55°C for 3 hours. After heating to room temperature, MeOH (5 mL) was added and stirred for 10 minutes. Subsequently, a mixed solvent of water and MeOH (60 mL) was added dropwise, followed by water (60 mL) and stirring for 1 hour. The reaction solution was filtered to obtain compound 14 (5.37 g, yield: 95.7%). (2) Compound A-3 The obtained compound A-3 １ H-NMR (CDCl ３ ) are shown below. １ H-NMR (CDCl ３): δ=6.05 (s, 6H), 4.85 (s, 2H), 5.38 (t, 4H), 5.90 (dd, 2H), 6.17 (dd, 2H), 6. 49 (dd, 2H), 7.23 (d, 2H), 7.24 (d, 2H), 7.35 (d, 2H), 7.45 (d, 2H), 7.57 (d, 2H)

[0145] Synthesis Example 4: Synthesis of compound A-4 Compound A-4 was synthesized according to the following scheme: A-4 was synthesized in the same manner as in steps (1) to (5) of Synthesis Example 1: Synthesis of compound A-1, except that compound 17 was used.

[0146]

[0147] (1) Synthesis of Compound 17 4-iodo-2-(trifluoromethyl)phenol (Compound 16: 3.00 g, 10.4 mmol), 4-iodobenzyl bromide (Compound 13: 3.17 g, 10.7 mmol), potassium carbonate (16.6 g, 12.0 mmol), and potassium iodide (0.17 g, 1.04 mmol) were dissolved in DMAc (15.0 mL) and stirred at 45°C for 30 minutes, and then at 55°C for 3 hours. After heating to room temperature, MeOH (5 mL) was added and stirred for 10 minutes. Subsequently, a mixed solvent of water and MeOH (60 mL) was added dropwise, followed by water (60 mL) and stirring for 1 hour. The reaction solution was filtered, and the resulting residue was purified by flash column chromatography to obtain Compound 17 (2.01 g, yield: 38.3%). (2) Compound A-4 １ H-NMR (CDCl ３ ) are shown below. Compound A-4 １ H-NMR (CDCl ３ ): δ = 5.23 (s, 2H), 5.38 (s, 4H), 5.88 (dd, 2H), 6.15 (dd, 2H), 6.47 (dd, 2H), 7.00 (d, 1H), 7,24 (s, 2H), 7.35 (d, 2H), 7.43 (d, 2H), 7.55 (d, 2H), 7.60 (dd, 1H), 7.78 (d, 1H)

[0148] Synthesis Example 5: Synthesis of Compound A-5 Compound A-5 was synthesized according to the following scheme: A-5 was synthesized in the same manner as in (1) to (5) of Synthesis Example 1: Synthesis of Compound A-1, except that compound 21 was used.

[0149]

[0150] (1) Synthesis of Compound 20 5-Iodosalicylic acid (Compound 19: 6.00 g, 22.8 mmol) and 4-(dimethylamino)pyridine (DMAP, 0.28 g, 2.27 mmol) were dissolved in t-butyl alcohol (60.0 mL), and then a mixture of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDIC.HCl, 6.53 g, 34.1 mmol) and THF (32.7 mL) was added dropwise. After stirring at room temperature for 5 hours, the solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography. Compound 20 (3.01 g, yield: 45.0%) was obtained.

[0151] (2) Synthesis of Compound 21 Compound 20 (3.00 g, 9.37 mmol), 4-iodobenzyl bromide (compound 13: 2.78 g, 9.37 mmol), potassium carbonate (1.49 g, 10.8 mmol), and potassium iodide (0.16 g, 0.94 mmol) were dissolved in DMAc (15.0 mL) and stirred at 45°C for 30 minutes, followed by stirring at 55°C for 3 hours. After heating to room temperature, MeOH (5 mL) was added and stirred for 10 minutes. Subsequently, a mixed solvent of water and MeOH (60 mL) was added dropwise, followed by water (60 mL) and stirring for 1 hour. The reaction solution was filtered to obtain compound 21 (4.86 g, yield: 96.8%).

[0152] (3) Compound A-5 The obtained compound A-5 １ H-NMR (CDCl ３ ) are shown below. Compound A-5 １ H-NMR (CDCl ３): δ = 1.56 (s, 9H), 5.19 (s, 2H), 5.38 (d, 4H), 5.87 (dd, 2H), 6.13 (dd, 2H), 6.45 (dd, 2H) , 6.95 (d, 1H), 7,23 (d, 2H), 7.34 (d, 2H), 7.47 (d, 2H), 7.52-7.56 (m, 3H), 7.87 (ds, 1H)

[0153] Synthesis Example 6: Synthesis of Compound A-6 Compound A-6 was synthesized according to the following scheme: Compound 4 was synthesized in the same manner as in (1) of Synthesis Example 1: Synthesis of Compound A-1.

[0154]

[0155] (1) Synthesis of Compound 25 Under a nitrogen atmosphere, 2,5-dibromotoluene (Compound 23: 10.0 g, 40.0 mmol), bis(pinacolato)diboron (Compound 24: 25.6 g, 100.8 mmol), and potassium acetate (9.90 g, 100.8 mmmmol) were dissolved in anhydrous DMF, and then dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II) (2.93 g, 4.00 mmol) was added and the mixture was stirred at 90°C for 12 hours. The solvent was evaporated under reduced pressure, and the resulting residue was purified by flash column chromatography to obtain Compound 25 (6.88 g, yield: 50.0%).

[0156] (2) Synthesis of Compound 26 Under a nitrogen atmosphere, compound 25 (3.0 g, 4.01 mmol), compound 4 (2.50 g, 10.0 mmol), and potassium carbonate (4.16 g, 30.1 mmol) were dissolved in 2-methyl THF (75.0 mL) and water (30.0 mL), and then tetrakis(triphenylphosphine)palladium (46.4 mg, 0.40 mmol) was added and stirred at 80°C for 10 hours. After cooling to room temperature, the reaction solution was extracted with chloroform. The resulting organic layer was dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was purified by crystallization using a mixed solvent of THF and MeOH to obtain compound 26 (0.91 g, yield: 53.1%).

[0157] (3) Synthesis of Compound A-6 Compound 26 (0.81 g, 1.88 mmol) was dissolved in DMAc (4.1 mL), and acryloyl chloride (0.61 mL, 7.56 mmol) was added dropwise thereto, followed by stirring at room temperature for 2 hours. Methanol (8.1 mL) was added thereto, followed by stirring at room temperature for 1 hour. The reaction solution was then filtered, and the resulting residue was purified by flash column chromatography to obtain Compound A-6 (0.71 g, yield: 70.0%). １ H-NMR (CDCl ３ ): δ = 2.50 (s, 3H), 5.39 (d, 4H), 5.88 (dd, 2H), 6.17 (dd, 2H), 6.45 (dd, 2H), 7.16 (s, 1H), 7.29 (s, 1H), 7.43-7.45 (m, 4H)

[0158] Synthesis Example 7: Synthesis of compound A-7 Compound A-7 was synthesized according to the following scheme: A-7 was synthesized in the same manner as in (1) to (3) of Synthesis Example 6: Synthesis of compound A-6, except that compound 27 (4,4'-diiodo-2,2'-dimethylbiphenyl) was used.

[0159]

[0160] Compound A-7 １ H-NMR (CDCl ３ ): δ = 2.16 (s, 6H), 5.40 (s, 4H), 5.88 (dd, 2H), 6.16 (dd, 2H), 6.48 (dd, 2H), 7.14 (d, 2H), 7.28 (s, 2H), 7,44 (s, 2H), 7.47-7.52 (m, 4H)

[0161] [Synthesis of Comparative Example Compound (Compound B-1)] Compound B-1 was synthesized as a comparative compound according to WO 2019 / 182129.

[0162] [Specific Compounds and Comparative Compounds] The specific compounds (compounds A-1 to A-7) and the comparative compound (compound B-1) synthesized in the upper part are shown below.

[0163]

[0164]

[0165] [Examples 1 to 7 and Comparative Example 1] The following evaluations were carried out using compounds A-1 to A-7 synthesized in the upper part of Examples 1 to 7. Furthermore, the following evaluations were carried out using compound B-1 synthesized in the upper part of Comparative Example 1.

[0166] [Evaluation] <Refractive Index, Birefringence> The refractive index and birefringence of the optically anisotropic layers prepared using compositions containing the compounds of the Examples and Comparative Examples (compounds A-1 to A-7, compound B-1) were evaluated.

[0167] (Preparation of Optically Anisotropic Layer for Measuring Refractive Index and Birefringence) First, Coating Composition E was prepared having the composition shown below. Note that Compound B-1 added together with each compound in the Examples and Comparative Examples is the same as Compound B-1 synthesized in the upper section as a comparative compound. That is, in Coating Composition E in Comparative Example 1, the total amount of Compound B-1 is 100 parts by mass. ------------------------------------------------ Composition of Coating Composition E------------------------------------------------ - 50 parts by mass of each compound in the Examples and Comparative Examples shown in Table 1 below - Compound B-1: 50 parts by mass - Polymerization initiator (OMNIRAD (registered trademark) 819, manufactured by BASF) - 3 parts by mass - Leveling agent T-1 (described below): 0.4 parts by mass - Chloroform: 1,500 parts by mass

[0168] The leveling agent T-1 is a compound having the following structure:

[0169] -Leveling agent T-1-

[0170]

[0171] The rubbed glass with the alignment film was spin-coated with Coating Composition E. The resulting glass with the coating of Coating Composition E was heated on a hot plate until the temperature reached a point where Coating Composition E exhibited a nematic phase. Then, the glass was further heated on the hot plate with 300 mJ / cm 2 of light through a filter that cuts off light with a wavelength of 350 nm or less. ２ The film was irradiated with ultraviolet light for 100 seconds to prepare an optically anisotropic layer.

[0172] (Evaluation of Refractive Index and Birefringence) The refractive index of the prepared optically anisotropic layer was measured using an ellipsometer (M-2000, manufactured by J.A. WOOLLAM). Specifically, measurements were performed at incident angles of 50°, 60°, and 70°, and Cauchy fitting was performed using the measured values ​​from 450 to 1700 nm to calculate the refractive index. The refractive index n e for extraordinary light at a wavelength of 550 nm and the birefringence Δn (i.e., the difference between n e and n o ) were calculated and classified based on the following evaluation criteria. A rating of "B" or higher is preferred, and "A" is most preferred. The results are shown in the "n e" and "Δn" columns of Table 1 below. A rating of "B" or higher is preferred, and "A" is most preferred. <Evaluation Criteria for Refractive Index n e> "A": 1.90≦n e. "B": 1.85≦n e < 1.90. "C": n e < 1.85. <Evaluation Criteria for Birefringence Δn> "A": 0.30≦Δn. "B": 0.25≦Δn<0.30. "C": Δn<0.25.

[0173] <Evaluation of Pattern Orientation> (Formation of Orientation Film) The following coating solution for forming an alignment film was dropped onto a glass substrate, and the substrate was rotated at 500 rpm for 5 seconds using a spin coater, followed by rotation at 2500 rpm for 20 seconds to coat the substrate. The substrate on which the coating film of the coating solution for forming an alignment film had been formed was dried on a hot plate at 60°C for 60 seconds to form an alignment film.

[0174] ------------------------------------------------------------------ Coating liquid for forming alignment film ------------------------------------------------------------------ Photo alignment material D 4.00 parts by mass Water 16.00 parts by mass Butoxyethanol 42.00 parts by mass Propylene glycol monomethyl ether 42.00 parts by mass ------------------------------------------------------------------

[0175] Photoalignment material D is a compound having the following structure.

[0176] -Photo alignment material D-

[0177]

[0178] (Exposure of Alignment Film) The alignment film was exposed using the exposure device shown in FIG. 5 of WO 2020 / 022496 to form an alignment film P-1 having an alignment pattern. The exposure device used was one that emitted laser light with a wavelength of 325 nm. The exposure dose by the interference light was 2000 mJ / cm. ２ One period of the alignment pattern formed by the interference of the two laser beams (the length of a 180° rotation of the optical axis derived from the liquid crystal compound) was controlled by changing the crossing angle (crossing angle β) of the two beams.

[0179] (Evaluation of Pattern Orientation) <<Preparation of Measurement Composition>> The following coating composition F was prepared as a measurement composition for evaluating pattern orientation. Note that the compound B-1 added together with each compound in the examples and comparative examples is the same as the compound B-1 synthesized in the upper section as a comparative compound. That is, in coating composition F in comparative example 1, the total amount of compound B-1 was 100 parts by mass.

[0180] Coating composition F -------------------------------------------------- 50 parts by mass of each compound of the Examples and Comparative Examples shown in Table 1 below Compound B-1: 50 parts by mass Chiral agent (manufactured by BASF, Paliocolor (registered trademark) LC756): 6 parts by mass Polymerization initiator (manufactured by BASF, omnirad (registered trademark) 819): 2 parts by mass Leveling agent T-1 described above: 0.011 parts by mass Chloroform: 972 parts by mass

[0181] First, Coating Composition F was dropped onto the alignment film P-1, and the coating was performed by spinning it at 1500 rpm for 10 seconds using a spin coater. Next, the resulting coating film was subjected to a heat treatment, cooled, and then subjected to a curing treatment by ultraviolet irradiation to produce a cured layer (liquid crystal fixation layer). The resulting cured layer was observed under a polarizing microscope to check for the presence or absence of alignment defects, and evaluated according to the following evaluation criteria. The results are shown in the "Pattern alignment" column in Table 1. A rating of "B" or higher is preferable, with "A" being the most preferable. Evaluation Criteria: "A": No alignment defects. "B": Alignment defects are partially observed. "C": Alignment defects are observed over the entire surface.

[0182] Table 1 is shown below.

[0183]

[0184] The results in Table 1 clearly show that the optically anisotropic layer obtained by curing a composition containing a specific compound has a high refractive index ne for extraordinary light rays and a high birefringence Δn, and that the specific compound has excellent pattern alignment properties. Furthermore, comparison with the examples confirmed that when at least two of the n1 A1 and A2 in the above formula (I) represent the fused ring structure represented by the above formula (Ia), the performance is excellent.

[0185] Furthermore, by comparing the examples, it was confirmed that when n1 is an integer of 3 or more in the above formula (I), the pattern orientation of the specific compound is more excellent.

[0186] Furthermore, when the pattern-oriented optically anisotropic layer prepared in Example 1 was optically brought into close contact with a light guide plate, it was confirmed that light could be extracted from the light guide plate.

[0187] 1, 2, 3 Optically anisotropic layer xy plane sheet surface z direction thickness direction 30 liquid crystal compound Λ length of one period 30A optical axis derived from liquid crystal compound 30 θ angle R region d thickness (film thickness) of optically anisotropic layer P Ｌ Left circularly polarized light P Ｒ Right circularly polarized light L １ , L ４ , L ６ Incident light L ２ , L ５ , L ７ Transmitted light Q1, Q2 Absolute phase E1, E2 Equiphase surface A １ , A ２ , A ３ direction

Claims

1. A compound represented by the following formula (I). 【Chemistry 1】 In formula (I), P １ and P ２ Each of these independently represents a hydrogen atom, a polymerizable group, or a monovalent substituent, P １ and P ２ At least one of them is a polymerizable group. L １ and L ２ each independently represents a single bond or an alkylene group having 20 or fewer carbon atoms, and any —CH ２ — of the alkylene group may be replaced by —O—, —S—, —NR—, —CO—, or —CS—, and any —(CH ２ ) ２ — of the alkylene group may be replaced by —CH═CH— or —C≡C—, and any hydrogen atom of the alkylene group may be replaced by a fluorine atom or a chlorine atom. Z １ These are single bonds, -O-, -S-, -CHRCHR-, -OCHR-, -CO-, -SO-, -SO ２ -, -COO-, -CO-S-, -O-CO-O-, -CO-NR-, -SCHR-, -SO-CHR-, -SO ２ -CHR-, -CF ２ O-, -CF ２ S-, -OCHRCHRO-, -SCHRCHRS-, -SO-CHRCHR-SO-, -SO ２ -CHRCHR-SO ２ -, -CH=CH-COO-, -CH=CH-OCO-, -CH=CH-CONR-, -CH=CH-COS-, -COO-CHRCHR-, -OCO-CHRCHR-, -COO-CHR-, -OCO-CHR-, -CR=CR-, -CR=N-, -N=CR-, -N=N-, -CR=N-N=CR-, -CF=CF-, -C≡C-C≡C-, -C≡C-, or an alkylene group having 10 or fewer carbon atoms, and any -CH of the alkylene group ２ - may be replaced with -O-, -S-, -NR-, -CO-, or -CS-, and any -(CH) of the alkylene group ２ ) ２ The - can be replaced with -CH=CH- or -C≡C-, and any hydrogen atom of the alkylene group may be replaced with a fluorine atom or a chlorine atom. Note that Z in the formula １ If there are multiple Z １ The individuals may be identical or different from one another. R represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. n1 represents an integer between 1 and 7. A １ and A ２ Each of these independently represents a divalent aromatic ring group which may have substituents, or a divalent alicyclic group which may have substituents, and n of these A groups exist in the formula. １ and A ２ At least one of them is a fused ring structure represented by the following formula (Ia). Note that A is in the formula. １ If there are multiple A １ The individuals may be identical or different from one another. 【Chemistry 2】 In formula (Ia), X １ , X ２ , X ３ , and, X ４ Two of these represent -C(*) = X １ , X ２ , X ３ , and, X ４ The other two of these are, independently, -N = or -C(R Ａ ) represents =. R Ａ * represents a hydrogen atom or substituent. * represents a bond position.

2. In the above formula (Ia), X １ , X ２ , X ３ , and, X ４ Two of these represent -C(*) = X １ , X ２ , X ３ , and, X ４ The other two of them are -C(R Ａ The compound according to claim 1, which represents ) =.

3. In the above formula (Ia), X １ and X ４ The compound according to claim 1 or 2, wherein -C(*) =

4. In equation (I) above, there are n1 Z １ The compound according to claim 1 or 2, wherein at least one of the elements is -C≡C-.

5. In the above equation (I), there are n1 A １ and A ２ The compound according to claim 1 or 2, wherein at least two of the components are fused ring structures represented by formula (Ia).

6. In the above equation (I), there are n1 A １ and A ２ At least two of these are fused ring structures represented by formula (Ia), and X in the fused ring structure represented by formula (Ia) １ and X ４ The compound according to claim 1 or 2, wherein -C(*) =

7. In the above formula (I), P １ and P ２ The compound according to claim 1 or 2, wherein at least one of the groups represents a polymerizable group selected from the group consisting of the following formulas (P-1) to (P-19). 【Transformation 3】

8. In the above formula (I), P １ and P ２ The compound according to claim 7, wherein at least one of the groups represents a polymerizable group selected from formula (P-1) and formula (P-2).

9. The compound according to claim 1 or 2, wherein in formula (I), n1 represents an integer from 3 to 7.

10. The compound according to claim 1 or 2, wherein A1 and A2 each independently represent a optionally substituted divalent aromatic hydrocarbon ring group, an optionally substituted aromatic heterocyclic group composed of an optionally substituted aromatic heterocyclic ring having 5 to 6 members, a fused ring structure represented by the above formula (Ia), or an optionally substituted divalent alicyclic group, and at least one of the n1 A1 and A2 present in the formula is a fused ring structure represented by the above formula (Ia).

11. A composition comprising the compound described in claim 1 or 2.

12. Furthermore, the composition according to claim 11, further comprising a polymerization initiator.

13. Furthermore, the composition according to claim 12, further comprising a chiral agent.

14. The composition according to claim 13, having liquid crystalline properties.

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

16. An optical anisotropy obtained by curing the composition according to claim 11.

17. The optical anisotropy according to claim 16, having an orientation pattern in which the orientation of the optical axis derived from the compound is continuously rotated along at least one direction in the plane.

18. An optical element comprising the optical anisotropy described in claim 17.

19. A light guide element comprising the optical element and light guide plate described in claim 18.

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