Compounds, compositions, cured products, optical anisotropes, light guide elements
Patent Information
- Application Number
- JP2025058555
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2025-03-31
- Publication Date
- 2026-10-14
AI Technical Summary
【0009】 本発明によれば、異常光線に対する屈折率neが大きく、耐光性に優れる硬化物を形成できる化合物を提供できる。 また、本発明は、組成物、硬化物、光学異方体、及び、導光素子も提供できる。
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Figure 2026165909000001_ABST
Abstract
Description
[Technical Field]
[0001] This invention relates to compounds, compositions, cured products, optical anisotropes, and light guide elements. [Background technology]
[0002] Recently, polarization is used in many optical devices and systems, and there is a demand for optical elements using polymerizable liquid crystal compounds to control the reflection, focusing, and divergence of polarized light. As polymerizable liquid crystal compounds, for example, compounds containing a trans structure (hereinafter also referred to as "trans compounds") are known. Because trans compounds have a relatively high refractive index, whether the trans compound itself is liquid crystallized or is used in combination with other liquid crystal compounds without being liquid crystallized itself, optical anisotropes formed using a liquid crystal composition containing a trans compound tend to have a high refractive index and exhibit good incident angle-dependent diffraction efficiency.
[0003] For example, Patent Document 1 discloses a liquid crystal compound having a transstructure. [Prior art documents] [Patent Documents]
[0004] [Patent Document 1] International Publication No. 2009 / 086911 [Overview of the project] [Problems that the invention aims to solve]
[0005] The present inventors conducted a study on the liquid crystal compounds described in Patent Document 1, and found that in the cured products formed using the aforementioned liquid crystal compounds, the coexistence of a high extraordinary ray refractive index (the extraordinary ray refractive index refers to the refractive index ne for extraordinary rays) and excellent light resistance was not sufficiently achieved. The aforementioned light resistance is intended to mean the performance that the in-plane retardation (Re) of a cured product formed using the liquid crystal compound is less likely to change before and after irradiation when the cured product is irradiated with light.
[0006] In view of the above circumstances, the present invention has an object to provide a compound capable of forming a cured product that has a large refractive index ne for extraordinary rays and is excellent in light resistance. The present invention also has an object to provide a composition, a cured product, an optically anisotropic body, and a light guide element. [Means for Solving the Problems]
[0007] As a result of intensive studies conducted by the present inventors to solve the above problems, the present inventors have found that the above problems can be solved by the following configuration.
[0008] [1] A compound represented by Formula (1) described later. [2] In the above Formula (X1), Q 1 represents -NR-, Q 2 represents -O-, -S-, or -NR-, the compound according to [1]. [3] In the above Formula (1), Z 13 represents a single bond, -CR=CR-, -C≡C-, -CR=N-, or a linking group formed by combining two or more thereof, the compound according to [1] or [2]. [4] In the above Formula (1), A 11 , A 12 , and A 13 each independently represent a divalent cyclic group represented by any of Formula (1-1) to Formula (1-6) described later, the compound according to any one of [1] to [3]. [5] In the above Formula (1), A 11 , A 12 , and A 13The compounds according to any one of [1] to [4], wherein each independently represents a substituted 1,4-phenylene group or a substituted 2,6-naphthylene group. [6] In the above equation (1), Z 11 However, a compound that represents -O- or -S- as described in any of [1] to [5]. [7] A compound according to any one of [1] to [6], wherein the polymerizable group P in formula (1) above represents a radical polymerizable group containing an unsaturated double bond. [8] A compound according to any of [1] to [7], wherein the polymerizable group P in formula (1) above represents a polymerizable group represented by any of the formulas (P-31) to (P-42) described later. [9] The compounds described in [1] to [8], wherein the polymerizable group P represents a polymerizable group represented by formula (P-31) described later.
[10] A compound according to any of [1] to [9], wherein the above formula (1) has two or more polymerizable groups P.
[11] In the above formula (1), R 11 and R 12 However, all of these compounds represent a monovalent substituent containing a polymerizable group P, as described in any of [1] to
[10] .
[12] In the above equation (1), R 11 This represents a polymerizable group P, and R 12 This represents a monovalent substituent represented by formula (3) described later, or R 12 ga-L 12 - Represents a monovalent substituent represented by a polymerizable group P, and R 11 This represents a monovalent substituent represented by formula (3) described later, L 12 The compound described in any of [1] to
[11] , which represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. However, the -CH2- in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, or -C(=CH2)-, the -(CH2)2- in the alkylene group may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent.
[13] A compound described in any of [1] to
[12] that is liquid crystalline.
[14] A composition containing any of the compounds described in [1] to
[13] .
[15] The composition according to
[14] , further comprising a polymerizable liquid crystal compound.
[16] The composition according to
[15] , wherein the polymerizable liquid crystal compound is a compound represented by formula (2) described later.
[17] n 21 Individual Z 21 The composition according to
[16] , wherein at least one of them represents -C≡C-.
[18] A composition according to any one of
[14] to
[17] , which is liquid crystalline.
[19] A cured product obtained by curing any of the compositions described in
[14] to
[18] .
[20] An optical anisotropy obtained by curing any of the compositions described in
[14] to
[18] .
[21] An optical anisotropy obtained by curing any of the compositions described in
[14] to
[18] , An optical anisotropy having an orientation pattern in which the direction of the optical axis derived from the compound represented by formula (1) above is continuously rotated along at least one direction in the plane.
[22] A light guide element comprising the optical anisotropy described in
[21] and a light guide plate. [Effects of the Invention]
[0009] According to the present invention, it is possible to provide a compound that can form a cured product with a large refractive index ne for extraordinary light and excellent light resistance. Furthermore, the present invention can also provide compositions, cured products, optical anisotropes, and light guide elements. [Brief explanation of the drawing]
[0010] [Figure 1] This is a schematic diagram showing an embodiment of an optically anisotropic layer. [Figure 2] Figure 1 is a schematic plan view of the optically anisotropic layer. [Figure 3] Figure 2 is a conceptual diagram illustrating the function of the optical anisotropy layer. [Figure 4] Figure 2 is a conceptual diagram illustrating the function of the optical anisotropy layer. [Figure 5] This is a schematic diagram showing another example of an optically anisotropic layer. [Figure 6] This is a schematic diagram showing another example of an optically anisotropic layer. [Modes for carrying out the invention]
[0011] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. Please note that in each drawing, the scale of the components has been appropriately adjusted from the actual scale for easier viewing.
[0012] Furthermore, in this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively.
[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 the values at a wavelength of 550 nm. Furthermore, in this specification, n, ne, and no are values measured by ellipsometry.
[0014] Furthermore, the bonding direction of divalent groups as expressed herein is not limited unless otherwise specified. For example, in a compound represented by the formula "XYZ", if Y is -COO-, Y may also be -CO-O- or -O-CO-. Also, the above compound may be "X-CO-OZ" or "XO-CO-Z".
[0015] Furthermore, in this specification, when the term "substituent" is used, the substituent is not limited unless otherwise specified. The substituent is preferably a monovalent substituent. Examples of substituents include the group exemplified by substituent L below. In this specification, when the term "substituent L" is used, substituent L refers to the substituent L described below.
[0016] (substituent L) Examples of substituents L include C1-C10 alkyl groups, C1-C10 alkoxy groups, C1-C10 alkylamino groups, C1-C10 alkylthio groups, C2-C10 alkanoyl groups, C2-C10 alkanoyloxy groups, C2-C10 alkanoylamino groups, C2-C10 alkanoylthio groups, C2-C10 alkyloxycarbonyl groups, C2-C10 alkylaminocarbonyl groups, C2-C10 alkylthiocarbonyl groups, hydroxyl groups, amino groups, mercapto groups, carboxyl groups, sulfo groups, amide groups, cyano groups, nitro groups, halogen atoms, NCS groups, SO2NCS groups, OCN groups, trifluoromethyl groups, vinyl groups, and polymerizable substituents. However, if the group described as substituent L includes a -CH2- (methylene group), a group formed by replacing at least one of the -CH2- contained in the group with -O- or -CO- is also included in substituent L. Furthermore, if the group described as substituent L includes a -(CH2)2- (ethylene group), a group formed by replacing at least one of the -(CH2)2- contained in the group with -CH=CH- or -C≡C- is also included in substituent L. In addition, in the substitution of -CH2- and -(CH2)2- contained in the group described as substituent L with the other groups described above, for example, if the group has two or more -CH2-, one -CH2- may be replaced with -O- and the adjacent -CH2- may be replaced with -CO- to form an ester group (-O-CO-). Furthermore, if the group described as substituent L has a hydrogen atom, substituent L also includes a group obtained by replacing at least one of the hydrogen atoms in the group with at least one selected from the group consisting of a fluorine atom and a polymerizable group. In addition, if at least one of the -CH2- is replaced with -O- or -CO-, and if at least one of the -(CH2)2- is replaced with -CH=CH- or -C≡C-, the number of carbon atoms in the replaced state satisfies the predetermined numerical range described above. Furthermore, examples of the polymerizable substituents include monovalent substituents containing the polymerizable group P, which will be described later. Examples of monovalent substituents containing the polymerizable group P include -L w A monovalent substituent represented by -P is preferred. w R represents a single bond or a linear or branched alkylene group having 10 or fewer carbon atoms, wherein at least one of the -CH2- atoms in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, or -SO2-, at least one of the -(CH2)2- atoms in the alkylene group may be replaced with -CH=CH- or -C≡C-, and at least one of the hydrogen atoms in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. As the monovalent substituent represented by R, for example, an alkyl group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms) is preferred. Among the substituents L, alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, alkanoyl groups having 2 to 10 carbon atoms, alkanoyloxy groups having 2 to 10 carbon atoms, alkyloxycarbonyl groups having 2 to 10 carbon atoms, halogen atoms, or polymerizable substituents are preferred, and alkyl groups having 1 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, alkanoyl groups having 2 to 6 carbon atoms, alkanoyloxy groups having 2 to 6 carbon atoms, alkyloxycarbonyl groups having 2 to 6 carbon atoms, trifluoromethyl groups, fluorine atoms, or polymerizable substituents are more preferred.
[0017] (Polymerizable group P) Furthermore, in this specification, when referring to "polymerizable group P," examples include polymerizable groups capable of addition polymerization and cyclic polymerization (for example, radical polymerizable groups containing unsaturated double bonds), and examples include polymerizable groups represented by any of the following formulas (P-31) to (P-42). The polymerizable group P is preferably a polymerizable group represented by formulas (P-31) to (P-37) or formula (P-40), more preferably a polymerizable group represented by formulas (P-31) to (P-37), and even more preferably a polymerizable group represented by formula (P-31). Furthermore, in the polymerizable group represented by formula (P-31), R 42 In terms of superior effects and curability, a hydrogen atom or a methyl group is preferred, and a hydrogen atom is more preferred.
[0018] [ka]
[0019] X 1 Each of these independently represents either an oxygen atom or a sulfur atom. X 2 -O-, -S-, or -NR 42 - represents R 42 Each of these independently represents a hydrogen atom, a halogen atom, or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 5 carbon atoms, and more preferably a hydrogen atom or a methyl group. R 42 When is an aliphatic hydrocarbon group, at least one hydrogen atom in the aliphatic hydrocarbon group may be replaced by a halogen atom, and at least one -CH2- in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -NR-, -CO-, -CS-, -SO-, or -SO2-. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited, and examples include the substituent L mentioned above. R is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. The number of carbon atoms in the alkyl group represented by R is preferably 1 to 6, and more preferably 1 to 3. * indicates the connection position.
[0020] (Polymerizable group) Furthermore, in this specification, when the term "polymerizable group" is used, it refers to polymerizable groups that can undergo addition polymerization and cyclic polymerization (for example, radical polymerizable groups containing unsaturated double bonds), and a specific example of this is the polymerizable group exemplified above as an example of polymerizable group P.
[0021] Furthermore, in this specification, "solid content" of a composition means the components that form a cured product (e.g., an optically anisotropic layer) using the composition, and if the composition contains a solvent (organic solvent, water, etc.), it means all components excluding the solvent. In addition, liquid components that form a cured product (e.g., an optically anisotropic layer) are also considered to be solid content.
[0022] Furthermore, in this specification, unless otherwise specified, the thickness of a layer is the average value obtained by observing a cross-section cut by a microtome using an SEM (scanning electron microscope) or TEM (transmission electron microscope) and measuring the thickness at 10 points.
[0023] Furthermore, in this specification, when it is stated that the -CH2- and -(CH2)2- in aliphatic hydrocarbon groups and alkylene groups may be replaced with other linking groups (e.g., -O- and -S-), only one may be replaced, or two or more may be replaced. For example, if the group has two or more -CH2-, one -CH2- may be replaced with -O-, and the adjacent -CH2- may be replaced with -CO- to form an ester group (-O-CO-). Furthermore, if the hydrogen atoms in the above group may be replaced by other substituents (for example, fluorine atoms and chlorine atoms, etc.), then only one atom may be replaced, or two or more atoms may be replaced.
[0024] [Compound of the present invention] The main characteristic of the compound of the present invention (the compound represented by formula (1) described later; hereinafter also referred to as the "specific compound") is X 11 A point having a structural part represented by X 11 -A is located adjacent to it. 12 -Z 13 ―A 13 One notable feature is that it has a structural component represented by -. It is presumed that cured products formed using a specific compound (e.g., optically anisotropic layers) have a large refractive index ne for extraordinary light due to the structure of the specific compound (especially the structural part described above). Furthermore, cured products formed using a specific compound are thought to have a large refractive index ne for extraordinary light due to the specific compound being X 11 It is presumed that it has excellent light resistance due to having a structural component represented by [this symbol].
[0025] Hereinafter, "the effects of the present invention are superior" refers to obtaining at least one of the following effects: a higher refractive index ne for abnormal light rays in a cured product (e.g., an optically anisotropic layer) formed using a specific compound, and superior light resistance.
[0026] The following provides a detailed description of a compound represented by formula (1), which is one type of specific compound.
[0027] [ka]
[0028] In formula (1), R 11 and R 12 Each of these independently represents a monovalent substituent. However, R 11 and R 12 At least one of them represents a monovalent substituent containing a polymerizable group P. 11 and R 12 This will be explained later.
[0029] In formula (1), L 11 represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. The -CH2- in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, or -C(=CH2)-, the -(CH2)2- in the alkylene group may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited, and examples include the substituent L mentioned above. R is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. The number of carbon atoms in the alkyl group represented by R is preferably 1 to 6, and more preferably 1 to 3.
[0030] L 11 In terms of superior effects of the present invention, a linear or branched alkylene group having 1 to 14 carbon atoms, or a linear or branched alkylene group having 1 to 14 carbon atoms -X- is preferred, and a linear or branched alkylene group having 1 to 8 carbon atoms, or a linear or branched alkylene group having 1 to 8 carbon atoms -X- is more preferred. X represents -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, -CO-O-, -O-CS-, -S-CS-, -NR-CS-, or -C(=CH2)-. The hydrogen atoms in the above alkylene groups may be replaced with fluorine atoms or chlorine atoms.
[0031] In formula (1), Z11 -O-, -S-, -NR-, -CO-, -CS-, -SO-, or -SO2- represents a single bond, -O-, -S-, or -NR-, which are preferable in terms of superior effects of the present invention, a single bond, -O-, or -S- is more preferable, and -O- or -S- is even more preferable. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited, and examples include the substituent L mentioned above. R is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms. The number of carbon atoms in the alkyl group represented by R is preferably 1 to 6, and more preferably 1 to 3.
[0032] In formula (1), A 11 Each of these independently represents a divalent aromatic ring group which may have substituents, or a divalent alicyclic group which may have substituents. Note that A 11 If there are multiple A 11 The members may be the same as or different from one another.
[0033] Examples of divalent aromatic ring groups include divalent aromatic hydrocarbon ring groups and divalent aromatic heterocyclic ring groups. The aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon ring group may be monocyclic or polycyclic (fused ring). The number of carbon atoms in the aromatic hydrocarbon ring is preferably 6 to 20, and more preferably 6 to 10. The aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring.
[0034] The number of members in the aromatic heterocycle constituting the divalent aromatic heterocycle group is preferably 5 to 10, and more preferably 5 or 6. Examples of heteroatoms contained in the aromatic heterocycle include nitrogen atoms, oxygen atoms, and sulfur atoms. The number of carbon atoms in the aromatic heterocycle is preferably 3 to 20, and more preferably 3 to 10. Examples of the aromatic heterocycle include pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, triazine rings, thiophene rings, thiazole rings, imidazole rings, thienothiophene ring groups, thienothiazole rings, thiazolothiazole rings, and benzothiophene rings.
[0035] Examples of divalent alicyclic groups include divalent aliphatic hydrocarbon ring groups and divalent aliphatic heterocyclic groups. The aliphatic hydrocarbon ring constituting the divalent aliphatic hydrocarbon ring group may be monocyclic or polycyclic (fused ring). The number of members of 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 cyclopentane, cyclohexane, cycloheptane, cyclooctane, norbornene, and adamantane. Among these, cyclopentane or cyclohexane rings are preferred.
[0036] The aliphatic heterocycle constituting the divalent aliphatic heterocyclic group may be monocyclic or polycyclic (fused). Examples of heteroatoms included in the aliphatic heterocycle include nitrogen, oxygen, and sulfur atoms. The number of members in the aliphatic heterocycle is not particularly limited, but 5 to 10 is preferred. Examples of the aliphatic heterocycle include oxolane rings, oxane rings, piperidine rings, and piperazine rings. The aliphatic heterocycle may also have -CH2- groups substituted with -CO- groups, for example, a phthalimide ring.
[0037] The above-mentioned divalent aromatic ring group and the above-mentioned divalent alicyclic group may have substituents. The substituents are not particularly limited, and examples include substituent L.
[0038] In formula (1), A 12 and A 13 Each of these independently represents a divalent aromatic ring group which may have substituents. A 12 and A 13 A divalent aromatic ring group which may have substituents represented by A 11 This is synonymous with a divalent aromatic ring group which may have substituents represented by , and the preferred embodiment is the same. However, A 12 If it is a 6-membered ring, A 12 Z that combines with 11 or Z 12 And, Z 13This means it connects at the para position. In other words, n 11 When A is 0, 12 is Z 11 and Z 13 It is combined with Z 11 and Z 13 It bonds at the para position. Also, n 11 When A represents an integer from 1 to 4, 12 is Z 12 and Z 13 It is combined with Z 12 and Z 13 It bonds in the para position. 13 If it is a 6-membered ring, then Z 13 and X 11 This means it binds at the para position.
[0039] A 11 , A 12 , and A 13 Each of these is preferably a divalent aromatic ring group which may have substituents, and more preferably a divalent ring group represented by any of the following formulas (1-1) to (1-6). In equations (1-1) to (1-6), * indicates a bonding position.
[0040] [ka]
[0041] In formulas (1-1) to (1-6), W 1 Each of these is independent of the other, =CR 1 - or =N- represents Y 1 Each of these is independently of -NR 1 Represents -, -O-, or -S-. 1 represents a hydrogen atom or a monovalent substituent. * represents a bond position. R 1 The monovalent substituent represented by is not particularly limited, and examples include the substituent L mentioned above, with alkyl groups having 1 to 10 carbon atoms being preferred. R 1 Of these, a hydrogen atom or an alkyl group having 1 to 6 carbon atoms is preferred, a hydrogen atom or an alkyl group having 1 to 3 carbon atoms is more preferred, and a hydrogen atom or a methyl group is even more preferred.
[0042] A 11 , A 12 , and A 13 Each of these is preferably an optionally substituted 1,4-phenylene group or an optionally substituted 2,6-naphthylene group. The above substituents are not particularly limited, and examples include the substituent L.
[0043] A 12 and A 13 At least one of the components is preferably a divalent fused ring group which may have substituents. The number of rings in the fused ring group can be 2 to 4, and it is preferable that the fused ring group is a two-ring fused ring group because it allows specific compounds to easily exhibit liquid crystalline properties and has excellent solubility.
[0044] The two-ring fused ring group is preferably a divalent ring group represented by formulas (1-2) to (1-6). The fused ring constituting the two-ring fused ring group is preferably a naphthalene ring, a thienothiophene ring, a thienothiazole ring, or a thiazolothiazole ring, with the naphthalene ring being more preferred.
[0045] In formula (1), Z 12 and Z 13 Each of these independently represents a single bond, -CR2CR2-, -CR=CR-, -C≡C-, -CR2O-, -CR2S-, -CR2NR-, -CR2CO-, -CR2CS-, -COO-, -COS-, -CONR-, -COCO-, -COCS-, -CSO-, -CSS-, -CSNR-, -CSCS-, -CR=N-, or a linking group formed by combining two or more of these. However, Z 13does not represent -CR₂O-CONR-, -CR₂O-CSNR-, -CR₂S-CONR-, -CR₂S-CSNR-, -CR₂NR-CONR-, or -CR₂NR-CSNR-, nor is it a linking group containing a group selected from the group consisting of -CR₂O-CONR-, -CR₂O-CSNR-, -CR₂S-CONR-, -CR₂S-CSNR-, -CR₂NR-CONR-, and -CR₂NR-CSNR-. Here, in the formula, Z 12 is present in plural, the plurality of Z 12 may be the same as or different from each other. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited, and examples thereof include the aforementioned substituent L, with an alkyl group having 1 to 10 carbon atoms being preferred. Above all, R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group.
[0046] Z 12 is preferably a single bond, -COO-, -OCR₂-CR₂O-, -OCR₂-CR₂O-CSNR-, or -NRCS-OCR₂-CR₂O-CSNR-, from the viewpoint that the effect of the present invention is more excellent.
[0047] Z 13 preferably represents a single bond, -CR=CR-, -C≡C-, -CR=N-, or a linking group formed by combining two or more thereof, from the viewpoint that the effect of the present invention is more excellent, and a single bond is more preferred.
[0048] In formula (1), n 11 represents an integer of 0 to 4. n 11 preferably represents an integer of 0 to 3.
[0049] In formula (1), X 11 represents a divalent linking group represented by either formula (X1) or formula (X2), and preferably represents the divalent linking group represented by formula (X1).
[0050] In formula (X1), Q 1 represents -O-, -S-, or -NR-. Q 2 represents -O-, -S-, -NR-, or a single bond. * represents the bonding position to A 13 , and ** represents the bonding position to R 12 . Q 1 is preferably -NR- from the viewpoint that the effects of the present invention are more excellent. Q 2 is preferably -O-, -S-, or -NR-, more preferably -O- or -NR-, and even more preferably -O-, from the viewpoint that the effects of the present invention are more excellent. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent represented by R is not particularly limited, and examples thereof include the aforementioned substituent L, and an alkyl group having 1 to 10 carbon atoms is preferable. Among these, R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group.
[0051] In formula (X2), Cy 1 represents a ring which may have a substituent and has at least one each of a nitrogen atom (intended to be the nitrogen atom explicitly shown in formula (X2)) and a carbon atom (intended to be the carbon atom in C(=S) explicitly shown in formula (X2)) as ring member atoms. * represents the bonding position to A 13 , and ** represents the bonding position to R 12 . Cy 1 The ring represented by may be either a monocyclic ring or a polycyclic (fused ring) ring. Cy 1 The ring represented by may contain a heteroatom other than the aforementioned nitrogen atom as a ring member atom. Examples of the heteroatom include a nitrogen atom, an oxygen atom, and a sulfur atom. Cy 1 The number of ring members of the ring represented by is not particularly limited, but is preferably 5 to 10, and more preferably 5 to 6. Cy 1The substituents that the ring represented by are not particularly limited, and examples include the substituent L mentioned above.
[0052] Cy 1 In the ring represented by , the nitrogen atom explicitly shown in formula (X2) and the carbon atom in C(=S) explicitly shown in formula (X2) are, for example, *-L A -(X A ) a It is preferable that the atoms are linked by a divalent linking group represented by -**. * represents the bond position with the nitrogen atom, and ** represents the bond position with the carbon atom. However, *-L A -(X A ) a -** is a structural part in which one of the hydrogen atoms of the ring-forming atoms is removed and R 12 It forms a coupling with. L A This represents a divalent aliphatic hydrocarbon group which may have substituents. Specific examples of divalent aliphatic hydrocarbon groups include ethylene and alkylene groups such as propylene. X A represents -O-, -S-, or -NR-. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited; for example, substituent L is one such substituent, and an alkyl group having 1 to 10 carbon atoms is preferred. R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group. 'a' represents either 0 or 1.
[0053] In formula (1), R 11 and R 12 Each of these independently represents a monovalent substituent. However, R 11 and R 12 At least one of them represents a monovalent substituent containing a polymerizable group P. The definition of polymerizable group P is as previously described. Among the polymerizable groups P, radical polymerizable groups containing an unsaturated double bond are preferred. Examples of radical polymerizable groups containing an unsaturated double bond include ethylene unsaturated groups, and polymerizable groups represented by any of the above formulas (P-31) to (P-37) are preferred, with the polymerizable group represented by formula (P-31) being more preferred.
[0054] R 11 The monovalent substituent represented by is not particularly limited, and examples include the above substituent L and the monovalent substituent represented by the following formula (3) described later. 11 Among the monovalent substituents represented by , monovalent substituents containing a polymerizable group P are preferred, and monovalent substituents representing a polymerizable group P or the following formula (3) are more preferred.
[0055] R 12 The monovalent substituent represented by is not particularly limited, for example, the substituents L and -L mentioned above. 12 -Examples include a monovalent linking group represented by the polymerizable group P, and a monovalent substituent represented by the following formula (3), which will be described later. L 12 represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. The -CH2- in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, or -C(=CH2)-, the -(CH2)2- in the alkylene group may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited; for example, substituent L is one such substituent, and an alkyl group having 1 to 10 carbon atoms is preferred. R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group. L 12 In terms of superior effects of the present invention, linear or branched alkylene groups having 1 to 14 carbon atoms are preferred, and linear or branched alkylene groups having 1 to 8 carbon atoms are more preferred.
[0056] R 12 Among the monovalent substituents represented by , monovalent substituents containing polymerizable group P are preferred, and -L 12 -A monovalent linking group represented by a polymerizable group P, or a monovalent substituent represented by the following formula (3), is more preferred.
[0057] [ka]
[0058] In formula (3), L 31 and L 32 Each of these independently represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. The -CH2- in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, or -C(=CH2)-, the -(CH2)2- in the alkylene group may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited; for example, substituent L is one such substituent, and an alkyl group having 1 to 10 carbon atoms is preferred. R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group.
[0059] In formula (3), L 31 In terms of superior effects of the present invention, linear or branched alkylene groups having 1 to 14 carbon atoms are preferred, linear or branched alkylene groups having 1 to 8 carbon atoms are more preferred, linear or branched alkylene groups having 1 to 4 carbon atoms are even more preferred, and linear or branched alkylene groups having 2 to 4 carbon atoms are particularly preferred. L 32In terms of superior effects of the present invention, linear or branched alkylene groups having 1 to 14 carbon atoms are preferred, and linear or branched alkylene groups having 1 to 8 carbon atoms are more preferred.
[0060] In formula (3), Z 31 and Z 32 Each of these independently represents a single bond or a divalent linking group that does not contain a ring structure. Examples of divalent linking groups that do not contain a ring structure include -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, -C(=CH2)-, linear or branched alkylene groups, or groups formed by combining two or more of these. The -CH2- in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, or -C(=CH2)-, the -(CH2)2- in the alkylene group may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited; for example, substituent L is one such substituent, and an alkyl group having 1 to 10 carbon atoms is preferred. R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group.
[0061] Z 31 and Z 32 In terms of superior effects of the present invention, single bonds, -O-, -S-, -NR-, -CO-, -CS-, or groups formed by combining two or more of these are preferred. Z 31 and Z 32 Specific examples include single bonds, -O-, -S-, -NR-, -CO-, -CS-, -NR-CS-O-, -NR-CS-S-, -NR-CS-NR-, -O-CS-S-, -O-CS-O-, -S-CS-S-, -NR-CS-, -O-CS-, and -S-CS-, etc.
[0062] In formula (3), A31 Each of these independently represents a divalent aromatic ring group which may have substituents, or a divalent alicyclic group which may have substituents. A 31 A divalent aromatic ring group and a divalent alicyclic group that may have substituents, represented by A in formula (1), are 11 This is synonymous with a substituted divalent aromatic ring group and a substituted divalent alicyclic group, and the preferred embodiments are the same. Note that A 31 If there are multiple A 31 The members may be the same as or different from one another.
[0063] In formula (3), n 31 n represents an integer from 0 to 6. 31 It is preferable that this represents an integer between 1 and 3.
[0064] In formula (3), P represents the polymerizable group P. The polymerizable group P is as previously described. In equation (3), * represents the bonding position.
[0065] In formula (1), R is more advantageous in terms of the effects of the present invention. 11 This represents a polymerizable group P, and R 12 This represents a monovalent substituent represented by formula (3), or R 12 ga-L 12 - Represents a monovalent substituent represented by a polymerizable group P, and R 11 It is preferable that this represents a monovalent substituent represented by formula (3).
[0066] Specific examples of particular compounds include the following formulas (A) to (E). Note that in equation (1), R 11 This represents a polymerizable group P, and R 12 This corresponds to the embodiment representing a monovalent substituent represented by formula (3), and the following formula (E) is, in formula (1), R 12 ga-L 12 - Represents a monovalent substituent represented by a polymerizable group P, and R 11This represents a monovalent substituent represented by formula (3) (where L 11 This corresponds to the mode in which a single bond is represented.
[0067] [ka] TIFF2026165909000007.tif54154
[0068] R in equation (A) 12N , and R in equation (C) 11N represents a monovalent substituent that does not have a polymerizable group. Examples of monovalent substituents that do not have a polymerizable group include the substituent L (provided that it does not have a polymerizable group), and alkyl groups having 1 to 10 carbon atoms are preferred. In formulas (A) to (E), P represents a polymerizable group P. The polymerizable group P is as previously described. L in equations (B), (C), and (E) 12 represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. The -CH2- in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO2-, or -C(=CH2)-, the -(CH2)2- in the alkylene group may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited; for example, substituent L is one such substituent, and an alkyl group having 1 to 10 carbon atoms is preferred. R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group. L 12 In terms of superior effects of the present invention, linear or branched alkylene groups having 1 to 14 carbon atoms are preferred, and linear or branched alkylene groups having 1 to 8 carbon atoms are more preferred. In formulas (A) to (E), L 11 , Z 11 , Z12 , Z 13 , A 11 , A 12 , A 13 , n 11 , and, X 11 L in equation (1) 11 , Z 11 , Z 12 , Z 13 , A 11 , A 12 , A 13 , n 11 , and, X 11 This is synonymous with the same thing, and the preferred embodiment is also the same. In equations (D) and (E), L 31 , L 32 , Z 31 , Z 32 , A 31 , and, n 31 L 31 , L 32 , Z 31 , Z 32 , A 31 , and, n 31 This is synonymous with the same thing, and the preferred embodiment is also the same.
[0069] In formula (D), n 31 The integer is preferably between 1 and 3, and more preferably 2 or 3. In formula (D), L 31 Z at the bonding position with 31 The group is preferably selected from the group consisting of -O-, -NR-CS-O-, -NR-CS-S-, -NR-CS-NR-, -O-CS-S-, -O-CS-O-, -S-CS-S-, -NR-CS-, -O-CS-, and -S-CS-, and more preferably -O-, *-NR-CS-O-**, *-NR-CS-S-**, or *-NR-CS-NR-**. Note that * is A 31 The bonding position with ** is L 31 This indicates the connection point with [the other element].
[0070] In formula (E), n 31 The integer is preferably between 1 and 3. In formula (E), L 31 Z at the bonding position with 31The group is preferably selected from the group consisting of -O-, -NR-CS-O-, -NR-CS-S-, -NR-CS-NR-, -O-CS-S-, -O-CS-O-, -S-CS-S-, -NR-CS-, -O-CS-, and -S-CS-, and more preferably -O-, *-NR-CS-O-**, *-NR-CS-S-**, or *-NR-CS-NR-**. Note that * is A 31 The bonding position with ** is L 31 This indicates the connection point with [the other element].
[0071] The following are examples of exemplary compounds represented by formula (1), which is a type of specific compound, but are not limited to these examples.
[0072] [ka]
[0073] [ka]
[0074] [ka]
[0075] [ka]
[0076] [ka]
[0077] [ka]
[0078] [ka]
[0079] [ka]
[0080] [ka]
[0081] [ka]
[0082] [ka]
[0083] [ka]
[0084] The specific compound may or may not be liquid crystalline, but it is preferable that it be liquid crystalline. Furthermore, when a compound is described as exhibiting liquid crystalline properties, it means that the compound possesses the property of exhibiting an intermediate phase between the crystalline phase (low temperature side) and the isotropic phase (high temperature side) when the temperature is changed. Specifically, as an observation method, the optical anisotropy and fluidity originating from the liquid crystalline phase can be confirmed by observing the compound under a polarizing microscope while heating or cooling it using a hot stage system such as the Mettler Toledo FP90.
[0085] [Composition] [Specific compound] The composition of the present invention contains a compound represented by formula (1) (specific compound). The specific compound is as described above. The composition of the present invention preferably has liquid crystal properties. The content of the specific compound in the composition is not particularly limited, but for example, it is preferably 5 to 100% by mass, more preferably 10 to 95% by mass, and even more preferably 20 to 80% 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 compounds. When using two or more compounds, it is preferable that their total content be within the above range. The content of specific compounds in the composition is not particularly limited, but is preferably 5 to 100% by mass, more preferably 10 to 95% by mass, and even more preferably 20 to 80% by mass, relative to the total mass of solids in the composition.
[0086] [Polymerizable liquid crystal compound] The composition of the present invention may contain polymerizable liquid crystal compounds other than the specified compound. Polymerizable liquid crystal compounds are compounds that have polymerizable groups and exhibit liquid crystal properties.
[0087] The polymerizable liquid crystal compound may be a rod-shaped liquid crystal compound or a disc-shaped liquid crystal compound, for example, a rod-shaped nematic liquid crystal compound having a polymerizable group. Examples of rod-shaped nematic liquid crystal compounds include azomethines, azoxys, cyanobiphenyls, cyanophenyl esters, benzoic acid esters, cyclohexanecarboxylic acid phenyl esters, cyanophenylcyclohexanes, cyanosubstituted phenylpyrimidines, alkoxysubstituted phenylpyrimidines, phenyldioxanes, trans, and alkenylcyclohexylbenzonitriles. Furthermore, not only low-molecular-weight liquid crystal compounds but also high-molecular-weight liquid crystal compounds can be used.
[0088] The number of polymerizable groups in the polymerizable liquid crystal compound may be one or more, preferably 1 to 6, more preferably 1 to 3, and even more preferably 2. Polymerizable liquid crystal compounds are obtained by introducing polymerizable groups into liquid crystal compounds.
[0089] Examples of polymerizable groups include known chain polymerizable groups (chain polymerizable groups), among which unsaturated bonding groups (e.g., ethylenically unsaturated groups) are preferred, and radical polymerizable groups containing unsaturated double bonds are more preferred. Specific examples of polymerizable groups include polymerizable groups represented by any of the formulas (P-31) to (P-42) exemplified above as specific examples of polymerizable group P. Among these polymerizable groups, the polymerizable group represented by formula (P-31) is more preferred.
[0090] As the polymerizable liquid crystal compound, the compound represented by the following formula (2) is preferred.
[0091] [ka]
[0092] In formula (2), P 21 and P 22 Each of these independently represents a polymerizable group. The definition of a polymerizable group is as described above.
[0093] n 21 This represents an integer between 1 and 10. n 21 Preferably, the integer is between 2 and 8, and more preferably between 2 and 6.
[0094] L 21 and L 22 Each of these independently represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. The -CH2- in the alkylene group may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, or -SO2-, the -(CH2)2- in the alkylene group may be replaced with -CH=CH- or -C≡C-, and the hydrogen atom in the alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. The monovalent substituent is not particularly limited; for example, substituent L is one such substituent, and an alkyl group having 1 to 10 carbon atoms is preferred. R is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group. L 21 and L 22The number of carbon atoms in the alkylene group represented by is preferably 1 to 12, more preferably 1 to 10, and even more preferably 1 to 6. L 21 and L 22 Among these, alkylene groups having 1 to 10 carbon atoms, in which -CH2- may be substituted with -O-, -S-, or -COO-, are preferred, and alkylene groups having 1 to 6 carbon atoms, in which -CH2- may be substituted with -O-, -S-, or -CO-O-, are more preferred. L 21 and L 22 The alkylene group represented above may have a substituent (preferably the substituent L mentioned above), but it is preferable that it does not.
[0095] Z 21 This represents a single bond or a divalent linking group. Z 21 The divalent linking group represented by represents a group consisting of one or more selected from the group consisting of -CH2-, -O-, -NH-, -S-, -C=C-, -CO-, -CS-, -CH=N-, -N=N-, and -C≡C-. However, any substitutable hydrogen atom in these groups may be substituted with a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.). Z 21As, a single bond, -O-, -S-, -OCH₂-, -CH₂CH₂-, -CO-, -CS-, -COO-, -CSO-, -CSS-, -CO-S-, -O-CO-O-, -CO-CO-, -CO-NH-, -SCH₂-, -CF₂O-, -CF₂S-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH₂CH₂-, -OCO-CH₂CH₂-, -COO-CH₂-, -OCO-CH₂-, -COO-NH-, -OCO-NH-, -CH=CH-, -N=N-, -CH=N-N=CH-, -CH=N-, -CF=CF-, -C≡C-, -C≡C-C≡C-, -OCH₂CH₂O-, or -SCH₂CH₂S- is preferable; a single bond, -OCH₂-, -CH₂CH₂-, -COO-, -CSO-, -CSS-, -CO-S-, -CO-CO-, -CO-NH-, -SCH₂-, -CF₂O-, -CF₂S-, -CH=N-, -C≡C-, or -C≡C-C≡C- is more preferable; and a single bond, -OCH₂-, -C≡C-, or -COO- is even more preferable. n 21 Z groups 21 Among the divalent linking groups represented by, it is preferable that at least one thereof is -C≡C-, from the viewpoint of excellent anisotropy when used as an optically anisotropic layer.
[0096] A 21 and A 22 each independently represent a divalent aromatic ring group which may have a substituent, or a divalent alicyclic group which may have a substituent.
[0097] Examples of the divalent aromatic ring group include a divalent aromatic hydrocarbon ring group and a divalent aromatic heterocyclic group. The aromatic ring constituting the divalent aromatic ring group may be either monocyclic or polycyclic (fused ring). The number of carbon atoms in the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon ring group is preferably 6 to 10. Specific examples of the aromatic hydrocarbon ring include a benzene ring and a naphthalene ring, and a benzene ring is more preferable. The number of ring members of the aromatic heterocyclic ring constituting the divalent aromatic heterocyclic group is preferably 5 to 10, more preferably 5 or 6. Examples of the heteroatom contained in the aromatic heterocyclic ring include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of heteroatoms contained in the aromatic heterocyclic ring is not particularly limited, and is, for example, preferably 1 to 4, more preferably 1 or 2.
[0098] Examples of the divalent alicyclic group include a divalent aliphatic hydrocarbon ring group and a divalent aliphatic heterocyclic group. The alicyclic ring constituting the divalent alicyclic group may be either a monocyclic ring or a polycyclic (fused ring) ring. The number of ring members of the aliphatic hydrocarbon ring constituting the divalent aliphatic hydrocarbon ring group is preferably 5 to 12, more preferably 5 to 10, and still more preferably 5 or 6. Examples of the heteroatom contained in the aliphatic heterocyclic ring constituting the divalent aliphatic heterocyclic group include a nitrogen atom, an oxygen atom, and a sulfur atom. The number of ring members of the aliphatic heterocyclic ring is not particularly limited, and is preferably 5 to 10.
[0099] The hydrogen atoms in the aforementioned divalent aromatic ring group and divalent alicyclic group may be substituted with other substituents. Examples of the other substituents include the aforementioned substituent L.
[0100] In formula (2), A 21 and A 22 are each preferably a divalent aromatic hydrocarbon ring group which may have a substituent. A 21 and A 22 As one embodiment, a phenylene group bonded at the 1-position and the 4-position may be mentioned.
[0101] Moreover, A 21 and A 22 As another embodiment, n 21 of A 21 and A 22 An embodiment in which at least one of them is any aromatic hydrocarbon ring group selected from the group consisting of groups represented by the following formulae (Ar-1) to (Ar-5) is also mentioned. A 21 and A22 If it contains any aromatic hydrocarbon ring group selected from the group consisting of groups represented by formulas (Ar-1) to (Ar-5), then n 21 This represents 2, and P 21 The second A from the side 21 This represents an aromatic hydrocarbon ring selected from the group consisting of groups represented by formulas (Ar-1) to (Ar-5), or n 21 This represents 4, P 21 Third A from the side 21 This represents an aromatic hydrocarbon ring selected from the group consisting of groups represented by formulas (Ar-1) to (Ar-5), or n 21 This represents 4, P 21 The second and fourth A from the side 21 This represents an aromatic hydrocarbon ring selected from the group consisting of groups represented by formulas (Ar-1) to (Ar-5), or n 21 represents 5, P 21 The second and fifth A from the side 21 A preferred embodiment is one in which the group consists of groups represented by formulas (Ar-1) to (Ar-5) and represents an aromatic hydrocarbon ring selected from this group.
[0102] [ka]
[0103] In formula (Ar-1), Q 1 This represents =N- or =CH-. Q 2 -S-, -O-, or -N(R 6 ) represents -. R 6 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 6 Examples of C1-C6 alkyl groups represented by include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl groups.
[0104] Y 1This represents an aromatic hydrocarbon ring group having 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group having 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Y 1 Examples of aromatic hydrocarbon ring groups having 6 to 12 carbon atoms, represented by , include the phenyl group, the 2,6-diethylphenyl group, and the naphthyl group. Y 1 Examples of aromatic heterocyclic groups having 3 to 12 carbon atoms, represented by , include the thienyl group, thiazolyl group, furyl group, and pyridyl group. Y 1 Examples of alicyclic hydrocarbon groups having 6 to 20 carbon atoms, represented by the formula, include the cyclohexylene group, cyclopentylene group, norbornylene group, and adamantylene group. Also, Y 1 Examples of substituents that may be present include the substituent L mentioned above.
[0105] Also, in the above equations (Ar-1) to (Ar-5), Z 1 , Z 2 , and Z 3 These are, independently, a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon ring group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic ring group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, and -OR. 7 , -NR 8 R 9 , -SR 10 ,-COOR 11 , or -COR 12 It represents. R 7 ~R 12 Each of these independently represents either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Also, Z 1 and Z 2 These may combine with each other to form an aromatic ring.
[0106] Z1 , Z 2 , and Z 3 As the monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by , alkyl groups having 1 to 15 carbon atoms are preferred, and alkyl groups having 1 to 8 carbon atoms are more preferred. Z 1 , Z 2 , and Z 3 Examples of monovalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms, represented by , include the methyl group, ethyl group, isopropyl group, tert-pentyl group (1,1-dimethylpropyl group), tert-butyl group, and 1,1-dimethyl-3,3-dimethylbutyl group.
[0107] Z 1 , Z 2 , and Z 3 Examples of monovalent alicyclic hydrocarbon groups having 3 to 20 carbon atoms, represented by , include monocyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, methylcyclohexyl, and ethylcyclohexyl; monocyclic unsaturated hydrocarbon groups such as cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, cyclopentadienyl, cyclohexadienyl, cyclooctadiene; bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, tricyclo[5.2.1.0 2,6 ]decyl group, tricyclo[3.3.1.1 3,7 ] Decyl group, tetracyclo[6.2.1.1 3,6 .0 2,7 Examples include polycyclic saturated hydrocarbon groups such as dodecyl groups and adamantyl groups.
[0108] Z 1 , Z 2 , and Z 3 As the monovalent aromatic hydrocarbon ring group having 6 to 20 carbon atoms represented by , an aryl group having 6 to 12 carbon atoms (particularly a phenyl group) is preferred. 1 , Z 2 , and Z 3Examples of the monovalent aromatic hydrocarbon ring group having 6 to 20 carbon atoms represented by include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, and a biphenyl group. Z 1 , Z 2 , and Z 3 Examples of the monovalent aromatic heterocyclic group having 6 to 20 carbon atoms represented by include a 4-pyridyl group, a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group. Z 1 , Z 2 , and Z 3 Examples of the halogen atom represented by include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
[0109] R 7 to R 12 Examples of the alkyl group having 1 to 6 carbon atoms represented by include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.
[0110] In the above formula (Ar-2) and formula (Ar-3), A 3 and A 4 each independently represent a group selected from the group consisting of -O-, -N(R 13 )-, -S-, and -CO-. R 13 represents a hydrogen atom or a substituent. R 13 Examples of the substituent represented by include the aforementioned substituent L.
[0111] In formula (Ar-2), X represents a nonmetallic atom of Groups 14 to 16, which may have a hydrogen atom or a substituent bonded thereto. Examples of the nonmetallic atom of Groups 14 to 16 represented by X include an oxygen atom, a sulfur atom, a nitrogen atom to which a hydrogen atom or a substituent is bonded [=N-R N1 , R N1 represents a hydrogen atom or a substituent.], and a carbon atom to which a hydrogen atom or a substituent is bonded [=C-(R C1 )2, RC1 represents a hydrogen atom or substituent. Examples include: Examples of substituents include alkyl groups, alkoxy groups, alkyl-substituted alkoxy groups, cyclic alkyl groups, aryl groups (e.g., phenyl group, naphthyl group, etc.), cyano groups, amino groups, nitro groups, alkylcarbonyl groups, sulfo groups, and hydroxyl groups.
[0112] In formula (Ar-3), D 7 and D 8 Each of these can be independently linked by a single bond, or by -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -, -CR 3 =CR 4 -, -NR 5 - Represents a divalent linking group consisting of two or more combinations thereof. R 1 ~R 5 Each of these independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. D 7 and D 8 Examples of divalent linking groups represented by -CO-, -O-, -CO-O-, -CSO-, -CR 1 R 2 -, -CR 1 R 2 -CR 1 R 2 -, -O-CR 1 R 2 -, -CR 1 R 2 -O-CR 1 R 2 -,-CO-O-CR 1 R 2 -, -O-CO-CR 1 R 2 -, -CR 1 R 2 -O-CO-CR 1 R 2 -, -CR 1 R 2 -CO-O-CR 1 R 2 -, -NR 5 -CR 1 R 2-, and -CO-NR 5 - are examples, with -CO-, -O-, or -CO-O- being preferred.
[0113] In formula (Ar-3), L 3 and L 4 Each of these independently represents a single bond, a linear (linear or branched) alkylene group having 1 to 14 carbon atoms, or a divalent linking group in which one or more of the -CH2- atoms constituting a linear (linear or branched) alkylene group having 1 to 14 carbon atoms are substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent. An example of a substituent is the substituent L mentioned above.
[0114] In formula (Ar-3), P 3 and P 4 Each of these independently represents a monovalent organic group. However, P 3 and P 4 At least one of them represents a polymerizable group. P 3 and P 4 Examples of monovalent organic groups represented by include groups corresponding to the organic groups exemplified as substituent L (preferably alkyl groups, aryl groups, or heteroaryl groups), and polymerizable groups (preferably the polymerizable group P described above).
[0115] In formulas (Ar-4) to (Ar-5), Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Furthermore, Ay represents an organic group having 2 to 30 carbon atoms having a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have substituents, or at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Here, the aromatic rings in Ax and Ay may have substituents, or Ax and Ay may be bonded together to form a ring. Also, Q 3 This represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, which may have substituents. Examples of Ax and Ay are those described in paragraphs
[0039] to
[0095] of International Publication No. 2014 / 010325. Also, Q 3 Examples of C1-C20 alkyl groups represented by include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl groups. Examples of substituents include the substituent L mentioned above.
[0116] Note that in equation (2), A 21 If there are multiple A 21 The terms may be the same or different from each other. 21 If multiple Zs exist, 21 The members may be the same as or different from one another.
[0117] Polymerizable liquid crystal compounds also preferably contain a trans structure within the molecule. The trans structure refers to a structural site represented as *-Ph-C≡C-Ph-* (where Ph represents a benzene ring group which may have substituents, and * represents a bond position). When a polymerizable liquid crystal compound contains a transstructure within its molecule, the optically anisotropic layer formed by the composition tends to produce diffracted light with a large diffraction angle and high diffraction efficiency.
[0118] Furthermore, it is preferable that the polymerizable liquid crystal compound is a polymerizable liquid crystal compound with reverse wavelength dispersion. In this specification, "a liquid crystal compound is inversely wavelength-dispersive" means that when the in-plane retardation (Re) value in the visible light range is measured for an optically anisotropic layer made using such a liquid crystal compound, the Re value increases as the measured wavelength increases.
[0119] As polymerizable liquid crystal compounds, compounds described in Makromol. Chem., Vol. 190, p. 2255 (1989), Advanced Materials, Vol. 5, p. 107 (1993), U.S. Patent No. 4,683,327, U.S. Patent No. 5,622,648, U.S. Patent No. 5,770,107, International Publication No. 95 / 022586, International Publication No. 95 / 024455, International Publication No. 97 / 000600, International Publication No. 98 / 023580, International Publication No. 98 / 052905, Japanese Patent Publication No. 1-272551, Japanese Patent Publication No. 6-016616, Japanese Patent Publication No. 7-110469, Japanese Patent Publication No. 11-080081, and Japanese Patent Publication No. 2001-328973 can also be preferably used. Furthermore, polymerizable liquid crystal compounds can also be preferably used, such as those described in Japanese Patent Publication No. 11-513019 and Japanese Patent Application Publication No. 2007-279688.
[0120] Furthermore, two or more polymerizable liquid crystal compounds may be used in combination. Using two or more polymerizable liquid crystal compounds in combination can lower the orientation temperature.
[0121] In addition, as polymerizable liquid crystal compounds other than those mentioned above, cyclic organopolysiloxane compounds having a cholesteric phase, such as those disclosed in Japanese Patent Publication No. 57-165480, can also be used. Furthermore, the polymerizable liquid crystal compound may also be a polymer liquid crystal compound. Examples of polymer liquid crystal compounds that can be used include polymers in which liquid crystal-like mesogenic groups are introduced in the main chain, side chains, or both the main chain and side chains; polymer cholesteric liquid crystals in which cholesteryl groups are introduced in the side chains; liquid crystalline polymers such as those disclosed in Japanese Patent Publication No. 9-133810; and liquid crystalline polymers such as those disclosed in Japanese Patent Publication No. 11-293252.
[0122] As polymerizable liquid crystal compounds, those described in Japanese Patent Publication No. 2007-108732 and Japanese Patent Publication No. 2010-244038 can also be preferably used.
[0123] The birefringence Δn of the polymerizable liquid crystal compound is preferably 0.15 or higher, more preferably 0.20 or higher, and even more preferably 0.25 or higher, from the standpoint of excellent anisotropy when used as an optical anisotropic layer, and from the standpoint of obtaining diffracted light with high diffraction efficiency at large diffraction angles when used as a diffracting element. There is no particular upper limit, but it is often 0.80 or lower. Furthermore, specific examples of polymerizable liquid crystal compounds with high refractive index anisotropy include, for example, JP 2009-102245 A, JP 4655348, JP 4524827, JP 4720200, JP 2004-091380 A, JP 3972430, JP 4517416 A, JP 2002-128742 A, JP 4810750 A, JP 5888544 A, JP 2014-019654 A, JP 6241654 A, JP 6372060 A, JP 6323144 A, JP 2005-015406 A, and JP 20 Patent Publication No. 07-230968, Patent Publication No. 6761484, Patent Publication No. 6681992, International Publication No. 19 / 182129, CN01134217A, KR101069555B, KR101690767B, CN20120229730A, Patent Publication No. 4053782, JP A2009-249406, Patent Publication No. 4121075, JP A2005-528416, US6514578, International Publication No. 06 / 006819, JP A2011-184417, JP A2013-095685, JP A2013-103897, JP A Japanese Patent Publication No. 2002-088008, Japanese Patent Application Publication No. 2002-226412, Japanese Patent Application Publication No. 2012-167214, Japanese Patent Application Publication No. 2012-167068, Japanese Patent Application No. 2018-084511, Japanese Patent Application Publication No. 2003-055317, Japanese Patent Application Publication No. 2001-329264, Japanese Patent Application Publication No. 2002-0 Japanese Patent Publication No. 30016, Japanese Patent Publication No. 2003-055664, Japanese Patent Publication No. 2018-070889, Japanese Patent Publication No. CN102557896, Japanese Patent Publication No. US2015369982, Japanese Patent Publication No. 2020-105264, Japanese Patent Publication No. 2014-224237, Japanese Patent Publication No. 2012-051862, Japanese Patent Publication No. 2010-106274, Japanese Patent Publication No. 2005-179557, Japanese Patent Publication No. 2005-035985, Japanese Patent Publication No. 2002-012579, Japanese Patent Publication No. 2002-003845, Japanese Patent Publication No. 2001-233837, Japanese Patent Publication No. 2019-532167, Japanese Patent Publication No. 2016-509247, Japanese Patent Publication No. 2010-503733, Japanese Patent Publication No. 2003-533557, International Publication No. 19 / 098115, International Publication No. 18 / 034216, International Publication No. 18 / 221236, International Publication No. 18 / 123396, International Publication No. 18 / 003482,Examples include the compounds described in International Publication Nos. 17 / 086143, 14 / 192655, 13 / 161669, and 09 / 104468.
[0124] The content of polymerizable liquid crystal compounds in the composition is not particularly limited, but is preferably 0 to 95% by mass, more preferably 5 to 90% by mass, and even more preferably 20 to 80% by mass, based on the total mass of solids in the composition. The composition may use one polymerizable liquid crystal compound alone, or two or more compounds. When two or more compounds are used, it is preferable that their total content be within the above range. Furthermore, since the orientation temperature tends to decrease, it is also preferable for the composition to contain two or more polymerizable liquid crystal compounds.
[0125] The following are specific examples of polymerizable liquid crystal compounds, but are not limited thereto.
[0126] [ka]
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[0133] Furthermore, as polymerizable liquid crystal compounds, compounds represented by the following formulas (1) to (22) (in particular those exhibiting smectic properties) are preferred. In the following formulas (1) to (22), K (side chain structure) corresponds to one of the values in Tables K1 to K3 described later. In addition, in the table K1 to K3 below, the "*" shown in the side chain structure of K represents the bond position with the aromatic ring as explicitly shown in formulas (1) to (22) below. Furthermore, in the side chain structures represented by 2-2 in Table K2 and 3-2 in Table 3, the groups adjacent to the acryloyloxy group and methacryloyl group, respectively, represent propylene groups (groups in which a methyl group is replaced by an ethylene group), and represent a mixture of positional isomers with different methyl group positions.
[0134] [ka] TIFF2026165909000047.tif134138
[0135] [Table 1]
[0136] [Table 2]
[0137] [Table 3]
[0138] [Polymerization initiator] The composition may contain a polymerization initiator. Polymerization initiators include photopolymerization initiators and thermal polymerization initiators, with photopolymerization initiators that can initiate the polymerization reaction by ultraviolet irradiation being preferred. Examples of photopolymerization initiators include alkylphenone compounds, α-carbonyl compounds, acyloin ethers, α-hydrocarbon-substituted aromatic acyloin compounds, polynuclear quinone compounds, phenazine compounds, and oxadiazole compounds. If the composition contains a polymerization initiator, the content of the polymerization initiator in the composition is not particularly limited, but it is preferably 0.1 to 20% by mass, and more preferably 1 to 8% by mass, relative to the total mass of the liquid crystal compound. The composition may use one polymerization initiator alone or two or more. When using two or more, it is preferable that their total content is within the above range.
[0139] 〔solvent〕 The composition may contain a solvent. The solvent is preferably one that can dissolve each component blended in the composition, for example, ketones (e.g., acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and cyclopentanone), ethers (e.g., dioxane and tetrahydrofuran), aliphatic hydrocarbons (e.g., hexane), alicyclic hydrocarbons (e.g., cyclohexane), aromatic hydrocarbons (e.g., toluene, xylene, and trimethylbenzene), halogenated carbons (e.g., Examples include dichloromethane, dichloroethane, dichlorobenzene, and chlorotoluene, esters (e.g., methyl acetate, ethyl acetate, and butyl acetate), water, alcohols (e.g., ethanol, isopropanol, butanol, and cyclohexanol), cellosolves (e.g., methyl cellosolve and ethyl cellosolve), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide), and amides (e.g., dimethylformamide and dimethylacetamide). If the composition contains a solvent, the amount of solvent in the composition is preferably such that the solid content concentration is 0.5 to 30% by mass, and more preferably 1 to 20% by mass. The composition may use one solvent alone or two or more solvents. When using two or more solvents, it is preferable that their total content be within the above range.
[0140] [Chiral agents] The composition may contain a chiral agent. Chiral agents (optically active compounds) have the function of inducing a helical structure in the cholesteric liquid crystal phase. Since different chiral agents induce different helical twist directions or helical pitches, they should be selected according to the purpose. There are no particular restrictions on the chiral agents used. For example, compounds listed in "Liquid Crystal Device Handbook, Chapter 3, Section 4-3, Chiral Agents for TN (Twisted Nematic) and STN (Super Twisted Nematic), p. 199, edited by the 142nd Committee of the Japan Society for the Promotion of Science, 1989," as well as isosorbide and isomannide derivatives, can be used. 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 their derivatives. Furthermore, the chiral agent may have polymerizable groups. When both the chiral agent and the liquid crystal compound have polymerizable groups, a polymer can be formed by a polymerization reaction between the polymerizable chiral agent and the polymerizable liquid crystal compound, having repeating units derived from the polymerizable liquid crystal compound and repeating units derived from the chiral agent. In this embodiment, it is preferable that the polymerizable groups of the polymerizable chiral agent are of the same type as the polymerizable groups of the polymerizable liquid crystal compound. Furthermore, the chiral agent itself may be a liquid crystal compound.
[0141] When the chiral agent has a photoisomerizing group, it is preferable because, after coating and orientation, a pattern of the desired reflection wavelength corresponding to the emission wavelength can be formed by photomask irradiation with active light or the like. Preferred photoisomerizing groups are the isomerization site of a photochromic compound, an azo group, an azoxy group, or a cinnamoyl group. Specific compounds that can be used include those described in Japanese Patent Publication No. 2002-080478, 2002-080851, 2002-179668, 2002-179669, 2002-179670, 2002-179681, 2002-179682, 2002-338575, 2002-338668, 2003-313189, and 2003-313292, etc.
[0142] If the composition contains a chiral agent, the content of the chiral agent in the composition is not particularly limited, but is preferably 0.01 to 15% by mass, and more preferably 1.0 to 10% by mass, relative to the content of the liquid crystal compound.
[0143] [Other additives] The composition may contain other components besides those described above. Other components include, for example, silicon-containing compounds other than the specified compounds, non-polymerizable liquid crystal compounds, antioxidants, ultraviolet absorbers, sensitizers, stabilizers, plasticizers, chain transfer agents, polymerization inhibitors, defoamers, leveling agents, thickeners, flame retardants, surfactants, dispersants, and colorants such as dyes and pigments.
[0144] [Uses of the composition] A cured product can be obtained from the composition of the present invention. More specifically, a cured product can be obtained by polymerizing a specific compound in the composition of the present invention. The resulting cured material can be used as an optical anisotropy (optical anisotropic layer).
[0145] [Refractive index of optical anisotropies] The refractive index n of the optical anisotropy of the present invention is preferably 1.65 or higher, and more preferably 1.70 or higher, in that it results in a higher diffraction efficiency of the resulting film. Furthermore, the refractive index ne in the slow axis direction of the optical anisotropy is preferably 1.90 or higher, and more preferably 1.94 or higher. There is no particular upper limit, but for example, it is 3.0 or lower.
[0146] [Δn of optical anisotropy] The refractive index anisotropy Δn of the optical anisotropy of the present invention is preferably 0.30 or higher, and more preferably 0.35 or higher, in that it results in a higher diffraction efficiency of the resulting film. There is no particular upper limit, but for example, it is 0.80 or lower.
[0147] The following describes an optically anisotropic layer and a method for manufacturing the same.
[0148] [An example of an embodiment of an optically anisotropic layer] An example of an embodiment of the optically anisotropic layer, which is a cured product of the above-described composition, will be explained with reference to the drawings. Figures 1 and 2 show schematic cross-sectional diagrams of the optical anisotropy layer 1. Figure 1 is a schematic side view of the optical anisotropy layer 1, and Figure 2 is a schematic plan view showing the orientation pattern of the optical anisotropy layer 1 shown in Figure 1. In the drawings, the sheet surface of the sheet-like optical anisotropy layer 1 is defined as the xy plane, and the thickness direction is defined as the z direction.
[0149] As shown in Figure 1, the optically anisotropic layer 1 has an orientation pattern (length of one period Λ) in which the orientation of the optical axis originating from the liquid crystal compound 30 continuously rotates along at least one direction in the plane. In Figure 1, the liquid crystal compound 30 corresponds to the embodiment in which the liquid crystal compound 30 is the specific compound described above. However, the present invention is not limited to this embodiment, and the liquid crystal compound 30 may be composed of the specific compound and a polymerizable liquid crystal compound. In Figures 1-4, only the liquid crystal molecules present on one main surface side of the optical anisotropy layer 1 are shown in order to simplify the diagrams and clearly illustrate the structure of the optical anisotropy layer 1. However, the optical anisotropy layer 1 has a structure in which oriented liquid crystal compounds 30 are stacked, similar to optical anisotropy layers formed using compositions containing ordinary liquid crystal compounds. Typically, when the in-plane retardation value of the optical anisotropy layer 1 is set to λ / 2, it functions as a general λ / 2 plate, that is, it gives a half-wavelength, or 180°, phase difference to two mutually orthogonal linearly polarized components contained in the light incident on the optical anisotropy layer.
[0150] As shown in Figure 2, the optically anisotropic layer 1 has an orientation pattern in which the direction of the optical axis 30A (hereinafter sometimes abbreviated as "optical axis 30A") originating from the liquid crystal compound 30 changes while continuously rotating in one direction within the plane of the optically anisotropic layer 1. Here, the one direction in which the optical axis 30A changes rotation is assumed to coincide with the direction of the x-axis in the xy-plane. In the following, the one direction in which the optical axis 30A changes rotation will be described as the x-direction.
[0151] The optical axis 30A derived from the liquid crystal compound 30 is the axis in the liquid crystal compound 30 that has the highest refractive index, the so-called slow axis. As shown in Figure 1, when the liquid crystal compound 30 is a rod-shaped liquid crystal compound, the optical axis 30A is aligned with the long axis of the rod shape.
[0152] Specifically, the statement that the orientation of the optical axis 30A changes while continuously rotating in the x-direction means that the angle between the optical axis 30A of the liquid crystal compounds 30 arranged along the x-direction and the x-direction differs depending on the position in the x-direction, and that the angle between the optical axis 30A and the x-direction gradually changes along the x-direction from θ to θ+180° or θ-180°. Here, "gradually changing angle" may mean that the angle changes at regular angular intervals or that it changes continuously. However, the difference in angle between the optical axes 30A of 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.
[0153] On the other hand, in the liquid crystal compound 30 forming the optical anisotropy layer 1, in the y direction perpendicular to the x direction within the plane, that is, in the y direction perpendicular to the one direction (x direction) in which the optical axis 30A rotates continuously, liquid crystal compound 30 with the same orientation of the optical axis 30A are arranged at equal intervals. In other words, in the liquid crystal compound 30 forming the optical anisotropy layer 1, the angle between the orientation of the optical axis 30A and the x direction is equal for liquid crystal compound 30 arranged in the y direction. In the optical anisotropy layer 1, in such an orientation pattern of liquid crystal compound 30, the length (distance) over which the optical axis 30A of the liquid crystal compound 30 rotates by 180° in the x direction in which the orientation of the optical axis 30A changes continuously within the plane is defined as the length of one period Λ in the orientation pattern. In other words, the length of one period in the orientation pattern is defined by the distance over which the angle between the optical axis 30A of the liquid crystal compound 30 and the x direction changes from θ to θ+180°. Specifically, as shown in Figure 2, the distance between the centers in the x-direction of two liquid crystal compounds 30 whose x-direction coincides with the direction of the optical axis 30A is defined as the length of one period Λ (hereinafter sometimes referred to as "period Λ" or "period Λ"). The orientation pattern of the optical anisotropy layer 1 is a pattern in which this liquid crystal orientation of period Λ is repeated in the x-direction.
[0154] As described above, in the optically anisotropic layer 1, the liquid crystal compounds 30 arranged in the y-direction have an equal angle between their optical axis 30A and the x-direction, which is the direction of rotation of the optical axis of the liquid crystal compound 30. The region where liquid crystal compounds 30 with an equal angle between their optical axis 30A and the x-direction are arranged in the y-direction is defined as region R. In this case, the value of the in-plane retardation (Re) in each region R is preferably λ / 2 when the wavelength of the light to be diffracted by the optical anisotropy layer (hereinafter referred to as "target light") is λ. 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 optical anisotropy layer. Here, the refractive index difference associated with the refractive index anisotropy of region R in the optical anisotropy layer is defined as the refractive index 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 direction of the slow axis. That is, the refractive index anisotropy Δn associated with the refractive index anisotropy of region R is equal to the difference between the refractive index of the liquid crystal compound 30 in the direction of the optical axis 30A and the refractive index of the liquid crystal compound 30 in the direction perpendicular to the optical axis 30A in the plane of region R. In other words, the above refractive index anisotropy Δn depends on the liquid crystal compound, and the in-plane retardations of each region R are approximately the same. However, as previously mentioned, the direction of the optical axis 30A differs between each region R.
[0155] In the optically anisotropic layer 1, the orientation of the optical axis 30A rotates within the plane, making it difficult to measure the overall in-plane retardation. However, the in-plane retardation of the optically anisotropic layer 1 can be estimated from its period and diffraction efficiency.
[0156] When circularly polarized light is incident on such an optically anisotropic layer 1, the light is refracted and the direction of the circular polarization is changed. This effect is conceptually illustrated in Figure 3, which illustrates the optical anisotropy layer 1. It is assumed that the in-plane retardation of the optical anisotropy layer 1 is λ / 2. In this case, as shown in Figure 3, left-circularly polarized light P is present in the optical anisotropy layer 1. L When incident light L1 is incident, the incident light L1 passes through the optical anisotropy layer 1, giving it a phase difference of 180°, and the transmitted light L2 is right-circularly polarized P R It will be converted. Furthermore, as the incident light L1 passes through the optical anisotropy layer 1, its absolute phase changes according to the orientation of the optical axis 30A of each liquid crystal compound 30. At this time, the orientation of the optical axis 30A changes while rotating along the x-direction, so the amount of change in the absolute phase of the incident light L1 differs depending on the orientation of the optical axis 30A. Moreover, since the orientation pattern formed in the optical anisotropy layer 1 is a periodic pattern in the x-direction, the incident light L1 that has passed through the optical anisotropy layer 1 is given an absolute phase Q1 that is periodic in the x-direction and corresponds to the orientation of each optical axis 30A, as shown in Figure 3. As a result, an equiphase surface E1 tilted in the opposite direction to the x-direction is formed. Therefore, the transmitted light L2 is refracted so as to be tilted perpendicular to the equiphase plane E1, and propagates in a direction different from the direction of propagation of the incident light L1. In this way, left-circularly polarized light P L The incident light L1 is right-circularly polarized P, tilted at a constant angle in the x-direction relative to the direction of incidence. R It is converted to transmitted light L2.
[0157] On the other hand, as conceptually shown in Figure 4, right-circularly polarized light P is emitted from the optical anisotropy layer 1 having similar in-plane retardation. R When incident light L4 is incident, the incident light L4 passes through the optical anisotropy layer 1, resulting in a phase difference of 180°, and becomes left-circularly polarized P L It is converted to transmitted light L5. Furthermore, as the incident light L4 passes through the optical anisotropy layer 1, its absolute phase changes according to the orientation of the optical axis 30A of each liquid crystal compound 30. At this time, the orientation of the optical axis 30A changes while rotating along the x-direction, so the amount of change in the absolute phase of the incident light L4 differs depending on the orientation of the optical axis 30A. Moreover, since the orientation pattern formed in the optical anisotropy layer 1 is a periodic pattern in the x-direction, the incident light L4 that has passed through the optical anisotropy layer 1 is given an absolute phase Q2 that is periodic in the x-direction corresponding to the orientation of each optical axis 30A, as shown in Figure 4. Here, the incident light L4 is right-circularly polarized P R Therefore, the absolute phase Q2 that is periodic in the x-direction corresponding to the orientation of the optical axis 30A is left-circularly polarized P LThis is the opposite of the incident light L1. As a result, with incident light L4, an equiphase surface E2 is formed that is tilted in the x-direction in the opposite direction to that of incident light L1. Therefore, the incident light L4 is refracted so as to be tilted perpendicular to the equiphase plane E2, and travels in a direction different from the direction of propagation of the incident light L4. In this way, the incident light L4 is converted into transmitted light L5, which is left-circularly polarized and tilted by a certain angle in the direction opposite to the x-direction with respect to the direction of incidence.
[0158] As previously described, in the optical anisotropy layer 1, the in-plane retardation value 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 the diffraction of the target light. The in-plane retardation of the optical anisotropy layer for incident light with an x-direction wavelength of λnm is Re(λ)=Δn λ ×d is preferably within the range defined by the following formula and can be set as appropriate. 0.7 × (λ / 2) nm ≤ Δn λ ×d ≤ 1.3 × (λ / 2) nm
[0159] Here, the angle of refraction of transmitted light L2 and L5 can be adjusted by changing the period Λ of the orientation pattern formed in the optical anisotropy layer 1. Specifically, the shorter the period Λ of the orientation pattern, the stronger the interference between light passing through adjacent liquid crystal compounds 30, allowing for greater refraction of transmitted light L2 and L5. Furthermore, 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.
[0160] The film thickness d of the optical anisotropy layer 1 can be set appropriately to obtain the desired in-plane retardation, but it 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 optical anisotropy layer 1 is used as a birefringent mask to form an optical alignment pattern, a smaller film thickness d is preferable. A smaller film thickness d improves the accuracy of the optical alignment pattern formation. Furthermore, it is preferable that the ratio of the period Λ to the thickness d of the optically anisotropic layer, Λ / d, is 1 or greater.
[0161] The period Λ of the orientation pattern in optically anisotropic layer 1 is determined by observing the light-dark periodic pattern of the light and dark areas under crossed nicol conditions using a polarizing microscope, and then obtaining the period of the light and dark areas. Twice the period of the observed light-dark periodic pattern corresponds to the period Λ of the orientation pattern. Furthermore, the film thickness d of the optically anisotropic layer 1 can be measured, for example, by observing a cross-section of the optically anisotropic layer with a scanning electron microscope.
[0162] The optical anisotropy layer 1 preferably has a refractive index anisotropy Δn of 0.21 or higher at a wavelength of 550 nm. There is no particular upper limit, but 0.8 or lower is preferred.
[0163] Furthermore, it is preferable to make the optical anisotropy layer substantially broadband with respect to the wavelength of incident light by imparting a torsional component to the composition or by laminating different phase difference layers. For example, a method for realizing a broadband patterned λ / 2 plate by laminating two liquid crystal layers with different torsional directions in the optical anisotropy layer is shown in Japanese Patent Application Publication No. 2014-089476, and can be suitably used in the optical anisotropy layer of the present invention.
[0164] [Method for fabricating optically anisotropic layer 1] One specific example of a method for producing the optical anisotropy layer 1 is an embodiment comprising the steps of: step X, which involves bringing a composition into contact with a substrate having an alignment film having a predetermined orientation pattern to form a composition layer on the alignment film on the substrate; and step Y, which involves heat-treating the composition layer to orient the liquid crystal compound, followed by curing. Furthermore, after the fabrication of the optical anisotropy layer 1, the aforementioned substrate may or may not be removed from the optical anisotropy layer. Similarly, the aforementioned alignment film may or may not be removed from the optical anisotropy layer after the fabrication of the optical anisotropy layer 1.
[0165] The specific procedures for processes X and Y are described in detail below. (Process X) ·substrate In process X, the type of substrate used is not particularly limited and includes known substrates (e.g., resin substrates, glass substrates, ceramic substrates, semiconductor substrates, and metal substrates).
[0166] • Orientation membrane An alignment film is placed on the substrate. The presence of the alignment film makes it easier to orient the liquid crystal compound 30 into a predetermined alignment pattern when fabricating the optical anisotropy layer 1. As previously described, the optical anisotropy layer 1 has an alignment pattern in which the orientation of the optical axis 30A (see Figure 2) derived from the liquid crystal compound 30 changes while continuously rotating along one direction (x direction) in the plane. Therefore, the alignment film is formed so that the optical anisotropy layer can form this alignment pattern.
[0167] Various known orientation films are available. Examples of orientation films include rubbing films made of organic compounds such as polymers, obliquely deposited films of inorganic compounds, films having microgrooves, and films obtained by accumulating LB (Langmuir-Blodgett) films of organic compounds such as ω-tricosanoic acid, dioctadecylmethylammonium chloride, and methyl stearylate using the Langmuir-Blodgett method.
[0168] An oriented film formed by rubbing can be created by rubbing the surface of a polymer layer several times in a specific direction with paper or cloth. Suitable materials for use in the orientation film include polyimide, polyvinyl alcohol, polymers having polymerizable groups as described in Japanese Patent Publication No. 9-152509, materials used for forming orientation films as described in Japanese Patent Publication No. 2005-097377, Japanese Patent Publication No. 2005-099228, and Japanese Patent Publication No. 2005-128503.
[0169] Furthermore, as the alignment film, a so-called photo-alignment film, which is formed by irradiating a photo-alignable material with polarized or unpolarized light, can be suitably used. When forming an alignment film by irradiating with polarized light, the film can be formed by irradiating the photo-alignable material from a direction perpendicular or oblique, and when forming an alignment film by irradiating with unpolarized light, the film can be formed by irradiating the photo-alignable material from a direction oblique. Examples of photo-alignment materials used in photo-alignment films include those described in Japanese Patent Publication No. 2006-285197, Japanese Patent Publication No. 2007-076839, Japanese Patent Publication No. 2007-138138, Japanese Patent Publication No. 2007-094071, Japanese Patent Publication No. 2007-121721, Japanese Patent Publication No. 2007-140465, Japanese Patent Publication No. 2007-156439, and Japanese Patent Publication No. 200 Azo compounds described in Japanese Patent Publication No. 7-133184, Japanese Patent Publication No. 2009-109831, Japanese Patent No. 3883848 and Japanese Patent No. 4151746, aromatic ester compounds described in Japanese Patent Publication No. 2002-229039, and Murray having photo-orienting units described in Japanese Patent Publication No. 2002-265541 and Japanese Patent Publication No. 2002-317013 Examples include mido and / or alkenyl-substituted nadiimide compounds, photocrosslinkable silane derivatives described in Japanese Patent No. 4205195 and Japanese Patent No. 4205198, photocrosslinkable polyimides, photocrosslinkable polyamides and photocrosslinkable esters described in Japanese Patent Publication No. 2003-520878, Japanese Patent Publication No. 2004-529220 and Japanese Patent No. 4162850, and photodimerizable compounds described in Japanese Patent Publication No. 9-118717, Japanese Patent Publication No. 10-506420, Japanese Patent Publication No. 2003-505561, International Publication No. 2010 / 150748, Japanese Patent Publication No. 2013-177561 and Japanese Patent Publication No. 2014-012823, particularly cinnamate compounds, chalcone compounds and coumarin compounds. In particular, azo compounds, photocrosslinkable polyimides, photocrosslinkable polyamides, photocrosslinkable esters, cinnamate compounds, and chalcone compounds can be suitably used.
[0170] There are no restrictions on the thickness of the alignment film; the appropriate thickness should be set according to the material used to form the alignment film, so as to obtain the required alignment function.
[0171] The thickness of the orientation film is preferably 0.01 to 5 μm, and more preferably 0.05 to 2 μm.
[0172] The method for forming the alignment film is not particularly limited, and various known methods depending on the material used to form the alignment film can be used. In terms of the ease with which the orientation pattern of the optical anisotropy layer 1 can be formed, it is preferable that the photo-alignment film is formed as an alignment film by irradiating a photo-alignable material with polarized or unpolarized light, and the methods described in
[0078] to
[0080] etc. of International Publication No. 2020 / 022496 can be suitably applied.
[0173] • Procedure for process X The method for bringing a substrate equipped with an alignment film having a predetermined orientation pattern (hereinafter also referred to as "substrate with alignment film") into contact with a composition is not particularly limited. Examples include coating the composition onto the alignment film on the substrate, and immersing the substrate with the alignment film in the composition. Furthermore, after bringing the substrate with the alignment film into contact with the composition, a drying process may be performed as needed to remove the solvent from the composition layer placed on the alignment film on the substrate.
[0174] (Process Y) Step Y is a process in which the composition layer is heat-treated to orient the liquid crystal compound, and then cured. By heat-treating the composition layer, the liquid crystal compound is oriented and a liquid crystal phase is formed. For example, if the composition layer contains a chiral agent, a cholesteric liquid crystal phase is formed. The heat treatment conditions are not particularly limited, and the optimal conditions are selected according to the type of liquid crystal compound. The curing method is not particularly limited and includes photocuring and heat curing. Among these, photocuring is preferred, and ultraviolet irradiation is more preferred. For ultraviolet irradiation, light sources such as ultraviolet lamps are used. The cured product obtained by the above process corresponds to a layer in which the liquid crystal phase is fixed. In particular, when the composition contains a chiral agent, a layer in which the cholesteric liquid crystal phase is fixed is formed. Furthermore, these layers no longer need to exhibit liquid crystalline properties. More specifically, for example, the most typical and preferred embodiment of a "fixed" cholesteric liquid crystal phase is one in which the orientation of the liquid crystal compound that constitutes the cholesteric liquid crystal phase is maintained. More specifically, it is preferable that the layer is non-fluid and that the fixed orientation can be stably maintained without causing changes in the orientation due to external fields or external forces, usually in a temperature range of 0 to 50°C, and under more severe conditions, in a temperature range of -30 to 70°C.
[0175] [Modified example of an optically anisotropic layer] The optically anisotropic layer 2 shown in Figure 5 is an optically anisotropic layer in which the liquid crystal compound 30 is cholesterically oriented in the thickness direction.
[0176] Cholesteric liquid crystal phases are known to exhibit selective reflectivity at specific wavelengths. The center wavelength λ of selective reflection depends on the pitch P (period of the helix) of the helical structure in the cholesteric liquid crystal phase, and follows the relationship λ = n × P with respect to the average refractive index n of the cholesteric liquid crystal phase. Therefore, the center wavelength of selective reflection can be adjusted by adjusting the pitch of this helical structure.
[0177] The cholesteric liquid crystal phase exhibits selective reflectivity for either right-handed or left-handed circularly polarized light at specific wavelengths. Whether the reflected light is right-handed or left-handed depends on the twist direction (sense) of the helix of the cholesteric liquid crystal phase. Selective reflection of circularly polarized light by the cholesteric liquid crystal phase occurs when the twist direction of the helix of the cholesteric liquid crystal phase is to the right, and when the twist direction of the helix is to the left, it reflects left-handed circularly polarized light.
[0178] Furthermore, the half-width Δλ (nm) of the selective reflection band (circularly polarized reflection band) exhibiting selective reflection depends on the Δn of the cholesteric liquid crystal phase and the helical pitch P, following the relationship Δλ = Δn × P. Therefore, the width of the selective reflection band can be controlled by adjusting Δn.
[0179] In other words, the optical anisotropic layer 2 selectively reflects light in a predetermined wavelength range of specific circular polarization (right-circular polarization or left-circular polarization).
[0180] On the other hand, the orientation pattern of the optical axis 30A in the in-plane direction of the optical anisotropy layer 2 is the same as the orientation pattern of the optical anisotropy layer 1 shown in Figure 1, and therefore produces the same effect as the optical anisotropy layer 1. That is, the optical anisotropy layer 2, like the optical anisotropy layer 1 described above, has the effect of changing the absolute phase of incident light and bending it in a predetermined direction. Therefore, the optical anisotropy layer 2 has the effect of bending incident light in a direction different from the incident direction and the effect of the cholesteric orientation described above, and reflects light at a predetermined angle with respect to the reflection direction of specular reflection.
[0181] For example, suppose the cholesteric liquid crystal phase of the optical anisotropy layer 2 is designed to reflect right-circularly polarized light. In this case, as shown in Figure 5, right-circularly polarized light P is directed perpendicular to the main surface of the optical anisotropy layer 2, i.e., along the normal. R When light L6 is incident on it, reflected light L7 is generated in a direction that is tilted with respect to the normal direction. In other words, the optical anisotropy layer 2 functions as a reflective diffraction grating.
[0182] In the orientation patterns of the optically anisotropic layers shown in Figures 1-5, the optical axis 30A of the liquid crystal compound 30 rotates continuously along the x-direction only within the plane. However, in the optically anisotropic layer of the present invention, various configurations are available as long as the optical axis 30A of the liquid crystal compound 30 rotates continuously along one direction.
[0183] Figure 6 is a schematic plan view of the optical anisotropy layer 3 in an example of a design change. In Figure 6, the orientation pattern is shown by the optical axis 30A of the liquid crystal compound. The optical anisotropy layer 3 has an orientation pattern in which regions with the same orientation of the optical axis 30A are arranged concentrically, and one direction in which the orientation of the optical axis 30A changes while continuously rotating is arranged radially from the center of the optical anisotropy layer 3. In the optically anisotropic layer 3, the orientation of the optical axis 30A changes while continuously rotating along multiple directions that extend outward from the center of the optically anisotropic layer 3, for example, the direction indicated by arrow A1, the direction indicated by arrow A2, the direction indicated by arrow A3, and so on. When circularly polarized light is incident on the optically anisotropic layer 3 having this orientation pattern, the absolute phase changes in each local region where the optical axis orientation of the liquid crystal compound 30 differs. In this case, the amount of change in the absolute phase differs depending on the orientation of the optical axis of the liquid crystal compound 30 to which the circularly polarized light is incident.
[0184] Such an optically anisotropic layer 3, having a concentric orientation pattern, that is, an orientation pattern that changes as the optical axis rotates radially, can transmit incident light as divergent or focused light depending on the direction of rotation of the optical axis of the liquid crystal compound 30 and the direction of the incident circularly polarized light. In other words, by aligning the optical anisotropy layer in a concentric pattern, the optical anisotropy layer functions as, for example, a convex lens or a concave lens.
[0185] Here, when the orientation pattern of the optical anisotropic layer is concentric and the optical anisotropic layer acts as a convex lens, it is preferable to gradually shorten the period Λ in the orientation pattern, which is the rotation of the optical axis by 180°, from the center of the optical anisotropic layer 3 outward in one direction in which the optical axis rotates continuously. The angle of refraction of light with respect to the incident direction becomes larger as the period Λ in the orientation pattern becomes shorter. Therefore, by gradually shortening the period Λ in the orientation pattern from the center of the optical anisotropic layer 3 outward in one direction in which the optical axis rotates continuously, the focusing power of light by the optical anisotropic layer 3 can be further improved, and the performance as a convex lens can be improved.
[0186] Furthermore, depending on the application of the laminate, such as when forming a concave lens, it is preferable to gradually shorten the period Λ in the orientation pattern, where the optical axis rotates 180°, by rotating it in the opposite direction to the direction in which the optical axis continuously rotates, from the center of the optical anisotropy layer 3 outwards in one direction. The angle of refraction of light with respect to the incident direction increases as the period Λ in the orientation pattern becomes shorter. Therefore, by gradually shortening the period Λ in the orientation pattern from the center of the optical anisotropy layer 3 outwards in one direction in which the optical axis continuously rotates, the light divergence power of the optical anisotropy layer 3 can be further improved, and the performance as a concave lens can be improved.
[0187] Furthermore, it is also preferable to reverse the direction of rotation of the incident circularly polarized light, for example, when the optical anisotropy layer is a concave lens.
[0188] Conversely, the period Λ in the concentric orientation pattern may be gradually lengthened outward from the center of the optical anisotropy layer 3 in one direction in which the optical axis rotates continuously. Furthermore, depending on the application of the optical anisotropy layer, such as when it is desired to provide a light intensity distribution in transmitted light, it is also possible to use a configuration in which, instead of gradually changing the period Λ in one direction in which the optical axis rotates continuously, there are regions in which the period Λ is partially different in one direction in which the optical axis rotates continuously. 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 in which the period Λ is different in different regions.
[0189] Thus, the configuration that changes one period Λ, which is the rotation of the optical axis by 180°, in one direction in which the optical axis rotates continuously, can also be used in the configuration shown in Figures 1-4, in which the optical axis 30A of the liquid crystal compound 30 rotates continuously and changes only in the x-direction. For example, by gradually shortening the period Λ of the orientation pattern in the x-direction, an optically anisotropic layer that transmits light in a focused manner can be obtained. Furthermore, by reversing the direction in which the optical axis rotates 180° in the orientation pattern, an optically anisotropic layer that transmits light in a diffuse direction only in the x-direction can be obtained. Additionally, by reversing the rotation direction of the incident circularly polarized light, an optically anisotropic layer that transmits light in a diffuse direction only in the X-direction (indicated by the arrow) can also be obtained. Furthermore, depending on the application of the optical anisotropy layer, such as when it is desired to provide a light intensity distribution in the transmitted light, it is also possible to use a configuration in which there are regions in the x-direction where the period Λ is partially different, rather than gradually changing the period Λ in the x-direction.
[0190] [Optical elements and light guide elements] The optical element of the present invention has the above-mentioned optical anisotropy (for example, an optically anisotropic layer). While there are no particular limitations on the applications of optical elements, they can be used in various applications that transmit light in a direction different from the incident direction, such as optical path changing members, light focusing elements, light diffusion elements in a predetermined direction, and diffraction elements in optical devices. Among preferred applications is a light guide element. A light guide element typically includes a light guide plate and a diffraction element disposed on the light guide plate (preferably spaced apart from the light guide plate). The optical anisotropy layer of the present invention is suitably used as a diffraction element. In other words, the light guide element of the present invention includes a light guide plate and an optical anisotropy disposed on the light guide plate. [Examples]
[0191] The present invention will be described in more detail below based on examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified 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.
[0192] In the following, unless otherwise specified, "parts" and "%" represent "parts by mass" and "% by mass," respectively. The abbreviations used in the following explanations are as follows: THF: Tetrahydrofuran DMF: N,N-dimethylformamide DMAc: Dimethylacetamide
[0193] [Synthesis of specific compounds] <Synthesis Example 1: Synthesis of Compound A-1> Compound A-1 was synthesized according to the following scheme.
[0194] [ka]
[0195] (1) Synthesis of compound 2 6-Bromo-2-naphthol (Compound 1: 10.0 g, 44.8 mmol) and 2-bromoethanol (6.7 g, 56.0 mmol) were dissolved in DMF (40 mL), and then a mixed solution of potassium hydroxide (3.14 g, 56.0 mmol), potassium iodide (223 mg, 1.34 mmol), and water (6.6 mL) was added at room temperature. The mixture was then heated to 85 °C and stirred for 4 hours. After cooling to room temperature, diethyl ether was added and the mixture was filtered. The resulting organic layer was sequentially washed with water, 2% potassium hydroxide aqueous solution, and saline solution, and the solvent was removed by vacuum distillation. The resulting residue was purified by crystallization with methanol and water to obtain Compound 2 (7.5 g, yield 63%).
[0196] (2) Synthesis of compound 4 To a mixed solution of compound 2 (5.0 g, 16.8 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (compound 3: 4.1 g, 18.5 mmol), potassium carbonate (5.12 g, 37.1 mmol), DMF (37.5 mL), and water (12.5 mL), degassed under reduced pressure, tetrakis(triphenylphosphine)palladium (2.0 g, 1.68 mmol) was added. The mixture was then heated to 110°C and stirred for 2 hours. After cooling to room temperature, water was added. The resulting mixed solvent was extracted with ethyl acetate, then washed sequentially with water and saline solution, and dried over magnesium sulfate. The organic layer was filtered, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography to obtain compound 4 (2.45 g, yield 52%).
[0197] (3) Synthesis of compound 5 1,1'-thiocarbonyldi-2(1H)-pyridone (3.5 g, 15.0 mmol) was added to a mixed solution of compound 4 (4.0 g, 14.3 mmol) and THF (40 mL). After stirring at room temperature for 1 hour, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography to obtain compound 5 (3.45 g, 75% yield).
[0198] (4) Synthesis of compound 6 Acryloyl chloride (0.56 g, 6.2 mmol) was added to a mixed solution of compound 5 (1.0 g, 3.1 mmol) and DMAc (5 mL). After stirring at room temperature for 1 hour, methanol was added. The mixture was filtered to obtain compound 6 (1.0 g, 95% yield).
[0199] (5) Synthesis of A-1 Methanol (2.5 mL) was added to a mixed solvent of compound 6 (0.5 g, 1.3 mol) and DMF (7.5 mL). The mixture was then heated to 70°C and stirred for 5 hours. After cooling to room temperature, 10 mL of water was added and the mixture was stirred for 30 minutes. The mixture was filtered to obtain compound A-1 (0.47 g, yield 87%).
[0200] The structure of the obtained compound A-1 was identified by NMR (Nuclear Magnetic Resonance). Compound A-1 1 H-NMR (CDCl3): δ=4.18(s, 3H), 4.36(t, 2H), 4.60(t, 2H), 5.88(dd, 1H), 6.19(dd, 1H), 6.48(dd, 1H), 7.17(d, 1H) ), 7.21(dd, 1H), 7.26-7.27(m, 1H), 7.35(brs, 1H), 7.65-7.72(m, 3H), 7.80(dd, 2H), 7.96(s, 1H), 8.31(brs, 1H)
[0201] <Synthesis Example 2: Synthesis of Compound A-2> Compound A-2 was synthesized according to the following scheme.
[0202] [ka]
[0203] (1) Synthesis of A-2 To a mixed solvent of compound 6 (0.5 g, 1.3 mol) cooled to 0°C and DMF (5.0 mL), dimethylamine (0.7 mL) was added and the mixture was stirred at the same temperature for 1 hour. After adding 10 mL of methanol and stirring for 30 minutes, the mixture was filtered to obtain compound A-2 (0.39 g, 72% yield).
[0204] The structure of the obtained compound A-2 was identified by NMR. Compound A-2 1 H-NMR (CDCl3): δ=3.38(s, 6H), 4.35(t, 2H), 4.60(t, 2H), 5.87(dd, 1H), 6.19(dd, 1H), 6.47(dd, 1H), 7.10 (s, 1H), 7.17(d, 1H), 7.20(dd, 1H), 7.37(d, 2H), 7.64-7.73(m, 3H), 7.78(d, 1H), 7.80(d, 1H), 7.96(d, 1H)
[0205] <Synthesis Example 3: Synthesis of Compound A-3> Compound A-3 was synthesized according to the following scheme.
[0206] [ka]
[0207] (1) Combination of A-3 Compound 6 (1.0 g, 2.7 mol) and DMF (15 mL) were mixed with 2.8 g of hydroxyethyl acrylate. The mixture was heated to 90°C and stirred for 3 hours. After cooling to room temperature, methanol was added and the mixture was stirred for 1 hour. The mixture was filtered to obtain compound A-3 (0.46 g, 85% yield).
[0208] The structure of the obtained compound A-3 was identified by NMR. Compound A-3 1 H-NMR (DMSO-d6): δ=4.38(t, 2H), 4.45-4.50(m, 2H), 4.52(t, 2H), 4.67-4.79(m, 2H), 5.98(dd, 1H), 6.00(dd, 1H), 6.24(dd, 1H), 6.27(dd, 1H), 6.38(dd, 1H), 6.39(dd, 1H), 7.21(dd, 1H), 7.40(d, 1H), 7.43-7.50(m, 1H), 7.68-7.84(m, 4H), 7.89(t, 2H), 8.14(s, 1H), 11.4(s, 1H)
[0209] <Synthesis Example 4: Synthesis of Compound A-4> Compound A-4 was synthesized according to the following scheme.
[0210] [ka]
[0211] (1) Synthesis of compound 8 A mixed solution of diethanolamine (compound 7: 10.0 g, 9.5 mol), imidazole (2.1 g, 3.0 mol), and THF (66.7 mL), cooled to 0°C, was to be mixed with tert-butyldimethylsilyl chloride (4.3 g, 2.9 mol) and THF (33.3 mL) dropwise. The mixture was heated to room temperature and stirred for 4 hours, after which water was added. The resulting mixed solvent was extracted with ethyl acetate, washed with saline solution, and dried over magnesium sulfate. The organic layer was filtered, and the solvent was removed by vacuum distillation. The resulting residue was purified by flash column chromatography to obtain compound 8 (3.7 g, 58% yield).
[0212] (2) Synthesis of compound 9 Imidazole (0.48 g, 7.0 mmol) was added to a mixed solution of compound 5 (1.5 g, 4.7 mmol), tert-butyldimethylsilyl chloride (0.91 g, 6.1 mol), and DMF (15 mL), which had been cooled to 0°C. The mixture was stirred at room temperature for 2 hours, then cooled to 0°C. Methanol was added and the mixture was stirred for 1 hour, after which the mixture was filtered to obtain compound 9 (1.8 g, 90% yield).
[0213] (3) Synthesis of compound 10 Compound 8 (0.60 g, 2.8 mol) was added to a mixed solution of compound 9 (1.2 g, 2.8 mmol) cooled to 0°C and DMF (10 mL), and the mixture was stirred for 1 hour. After adding methyl tert-butyl ether, the mixture was filtered to obtain compound 10 (1.8 g, 98% yield).
[0214] (4) Synthesis of compound 11 To a mixed solution of compound 10 (1.5 g, 2.3 mmol), pyridine (0.54 g, 6.8 mmol), and DMF (12 mL), cooled to 0°C, tosyl chloride (0.44 g, 2.3 mmol) was added. After stirring at 50°C for 3 hours, water was added. The resulting mixed solvent was extracted with ethyl acetate, washed with saline solution, and dried over magnesium sulfate. The organic layer was filtered, and the solvent was removed by vacuum distillation. The resulting residue was purified by flash column chromatography to obtain compound 11 (0.56 g, yield 48%).
[0215] (5) Synthesis of compound 12 To a mixed solution of compound 11 (0.5 g, 0.78 mmol) cooled to 0°C and anhydrous THF (5.0 mL), tetrabutylammonium fluoride (approximately 1 mol / L THF solution: 1.8 mL, 1.8 mmol) was added. After stirring at 0°C for 20 minutes, water was added. The resulting mixed solvent was extracted with ethyl acetate, washed with saline solution, and dried over magnesium sulfate. The organic layer was filtered, and the solvent was removed by vacuum distillation. Methanol was added to the resulting residue and stirred for 1 hour, after which the mixture was filtered to obtain compound 12 (0.18 g, yield 56%).
[0216] (6) Synthesis of A-4 Acryloyl chloride (0.14 mL, 1.8 mmol) was added to a mixed solution of compound 12 (0.18 g, 0.44 mmol) and DMAc (0.9 mL) cooled to 0°C. After stirring at room temperature for 3 hours, water was added. The resulting mixed solvent was extracted with ethyl acetate, washed with saline solution, and dried over magnesium sulfate. The organic layer was filtered, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography to obtain compound A-4 (0.21 g, 91% yield).
[0217] The structure of the obtained compound A-4 was identified by NMR. Compound A-4 1 H-NMR (CDCl3): δ=3.18(t, 2H), 3.74(t, 2H), 3.86(t, 2H), 4.37(t, 2H), 4.47(t, 2H), 4.59(t, 2H), 5.87(dd, 1H), 5.88(dd, 1H), 6.17(d d, 1H), 6.18(dd, 1H), 6.46(dd, 1H), 6.47(dd, 1H), 7.03(d, 2H), 7.16(s, 1H) 7.17(dd, 1H), 7,64(d, 2H), 7.70-7.80(m, 3H), 7.98(s, 1H)
[0218] <Synthesis Example 5: Synthesis of Compound A-5> A-5 was synthesized according to the following scheme.
[0219] [ka]
[0220] (1) Synthesis of compound 13 To a mixed solvent of compound 2 (15.0 g, 0.056 mol) and pyridine (75 mL), cooled to 0°C, p-toluenesulfonyl chloride (32.1 g, 0.17 mol) was added and the mixture was stirred at the same temperature for 3 hours. After adding water, the mixture was stirred at room temperature for 1 hour. The mixture was filtered to obtain compound 13 (19.0 g, 99% yield).
[0221] (2) Synthesis of compound 15 To a mixed solution of 5-bromo-2-iodotoluene (compound 14: 6.7 g, 23 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (5.0 g, 23 mmol), potassium carbonate (11 g, 80 mmol), DMF (100 mL), and water (5 mL), tetrakis(triphenylphosphine)palladium (1.3 g, 0.11 mmol) was added. The mixture was then heated to 60°C and stirred for 10 hours. After removing the solvent under reduced pressure, the resulting residue was purified by flash column chromatography to obtain compound 15 (5.6 g, 94% yield).
[0222] (3) Synthesis of compound 16 Compound 15 (2.0 g, 5.9 mmol), Compound 13 (2.4 g, 5.8 mmol), potassium iodide (0.10 g, 0.6 mmol), and potassium carbonate (0.92 g, 6.7 mmol) were dissolved in DMF (8 mL) and stirred at 80°C for 1 hour. After cooling to room temperature, a mixed solution of acetic acid (0.42 g) and MeOH (2 mL) was added and stirred for 30 minutes. Then, water and MeOH were added and stirred at 20°C for 1 hour. The mixture was filtered to obtain Compound 16 (1.4 g, yield 48%).
[0223] (4) Synthesis of compound 17 To a mixed solution of compound 16 (degassed under reduced pressure), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, potassium carbonate, DMF (37.5 mL), and water (12.5 mL), tetrakis(triphenylphosphine)palladium was added. The mixture was then heated to 110°C and stirred for 2 hours. After cooling to room temperature, water was added. The resulting mixed solvent was extracted with ethyl acetate, then washed sequentially with water and saline solution, and dried over magnesium sulfate. The organic layer was filtered, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography to obtain compound 17.
[0224] (5) Synthesis of compound 18 1,1'-thiocarbonyldi-2(1H)-pyridone was added to a mixed solution of compound 17 and THF. After stirring at room temperature for 1 hour, the solvent was removed by distillation under reduced pressure. The resulting residue was purified by flash column chromatography to obtain compound 18.
[0225] (6) Synthesis of compound A-5 2-hydroxyethyl acrylate was added to a mixed solvent of compound 18 and DMF. The mixture was heated to 90°C and stirred for 3 hours. After cooling to room temperature, methanol was added and the mixture was stirred for 1 hour. The mixture was filtered to obtain compound A-5.
[0226] [Synthesis of comparative compounds (compounds B-1 and B-2)] Compound B-1 was synthesized as a comparative example in accordance with U.S. Patent Application No. 2022 / 0177782. Compound B-2 was synthesized as a comparative example in accordance with International Publication No. 2009 / 086911.
[0227] [Specific compounds and comparative compounds] The specific compounds (compounds A-1 to A-5) and comparative compounds (compounds B-1 to B-3) synthesized in the upper section are shown below.
[0228] [ka]
[0229] [ka]
[0230] [ka]
[0231] [Examples 1-5 and Comparative Examples 1-2] In the following examples 1 to 5, compounds A-1 to A-5 synthesized in the upper section were used, and the evaluations described below were performed. In addition, in comparative examples 1 to 2, compounds B-1 to B-2 synthesized in the upper section were used, and the evaluations described below were performed.
[0232] [Fabrication and evaluation of optically anisotropic layers] Optically anisotropic layers were prepared using compositions containing each of the compounds in the examples and comparative examples (compounds A-1 to A-5, compounds B-1 to B-2) according to the following procedure, and various evaluations of the obtained optically anisotropic layers were performed.
[0233] (Fabrication of optically anisotropic layers) First, a coating composition E with the following composition was prepared. ------------------------------------------------------------------ Composition of coating composition E ------------------------------------------------------------------ • 50 parts by mass of each compound from the examples and comparative examples shown in Table 4 below. ·Composition C-1 50 parts by mass • Polymerization initiator (manufactured by IGM RESINS BV, omnirad® 819) 3 parts by mass • Leveling agent T-1: 0.4 parts by mass Cyclopentanone 1045 parts by mass ------------------------------------------------------------------
[0234] Composition C-1 is a composition having the following structure.
[0235] [ka]
[0236] Leveling agent T-1 is a compound with the following structure.
[0237] [ka]
[0238] Coating composition E was dropped onto a glass with a rubbed PVA alignment film, and the coating composition E was applied using a spin coater, rotating at 1500 rpm for 10 seconds. The resulting glass coated with coating composition E was heated on a hot plate until the coating composition E reached a temperature at which it exhibited the nematic phase, and then further heated on the hot plate through a filter that cuts out light with a wavelength of 350 nm or less at a rate of 300 mJ / cm². 2 An optically anisotropic layer was fabricated by irradiating it with ultraviolet light.
[0239] (Evaluation of refractive index ne for extraordinary rays) The refractive index of the fabricated optical anisotropic layer was measured using an ellipsometer (JAWOOLLAM). Specifically, measurements were taken 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 ne for the extraordinary ray at a wavelength of 550 nm was calculated and classified according to the evaluation criteria below. An evaluation of "B" or higher is preferable, and "A" is the most preferable. The results are shown in Table 4. 《Refractive index ne: Evaluation criteria for abnormal light rays》 "A": 1.94 ≤ ne. "B": 1.90 ≤ ne < 1.94. "C": ne < 1.90.
[0240] (Lightfastness evaluation) A 2 μm thick PVA layer was laminated on an optically anisotropic liquid crystal layer, and a lightfastness test was conducted by irradiating it with Xe light for 3 days using a Super Xenon Weather Meter SX75 (Suga Test Instruments) through an SC40 cut filter (Fujifilm). In-plane retardation (Re) at 0° incidence before and after the lightfastness test was measured using a Mueller Matrix Polarimeter (Axometrics). The rate of change of Re was calculated using the following formula and classified according to the evaluation criteria below. An evaluation of "B" or higher is preferable, and "A" is the most preferable. The results are shown in Table 4. Re change rate (%) = {(Re before lightfastness test) - (Re after lightfastness test) / (Re before lightfastness test)) × 100} Lightfastness: Evaluation Criteria "A": The rate of change in Re is less than 1.0%. "B": The rate of change in Re is 1.0% or more and less than 3.0%. "C": The rate of change in Re is 3.0% or higher.
[0241] (Hardening evaluation) The optically anisotropic layer is immersed in tetrahydrofuran, and in-plane retardation (Re) is measured at 0° incidence. The rate of Re change is calculated using the following formula and classified according to the evaluation criteria below. An evaluation of "A" is preferable. The results are shown in Table 4. Re change rate (%) = {(Re before immersion) - (Re after immersion) / (Re before immersion)) × 100 Evaluation Criteria "A": The rate of change is less than 20%. "B": The rate of change in Re is 20% or more.
[0242] Table 4 is shown below.
[0243] [Table 4]
[0244] The results in Table 4 show that the optically anisotropic layer formed using the specific compound has a high refractive index ne for extraordinary light rays and excellent light resistance. The results from Examples 1-5 indicate that when a specific compound has two or more polymerizable groups P, its curability is superior. From a comparison of Examples 1 to 4, it can be confirmed that the smaller the proportion of the side chain portion relative to the mesogenic portion of a particular compound, the higher the refractive index ne for the abnormal ray. [Explanation of Symbols]
[0245] 1, 2, 3 Optically Anisotropic Layers xy surface, sheet surface z-direction, thickness direction 30 Liquid crystal compounds Λ is the length of one period. Optical axis derived from liquid crystal compound 30A θ angle R area d. Thickness (film thickness) of the optically anisotropic layer P L Left-hand circular polarization P R Right-hand circular polarization L1, L4, L6 incident light L2, L5, L7 transmitted light Q1, Q2 Absolute Phase E1, E2 isophase plane A1, A2, A3 direction
Claims
1. A compound represented by formula (1). 【Chemistry 1】 In formula (1), R 11 and R 12 Each of these independently represents a monovalent substituent. However, R 11 and R 12 At least one of them represents a monovalent substituent containing a polymerizable group P. L 11 represents a single bond, or a linear or branched alkylene group having 20 or less carbon atoms. -CH in the aforementioned alkylene group 2 - may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO 2 -, or -C(=CH 2 )-, and -(CH in the aforementioned alkylene group 2 ) 2 - may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and a hydrogen atom in the aforementioned alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. Z 11 These are single bonds, -O-, -S-, -NR-, -CO-, -CS-, -SO-, or -SO 2 This represents a negative sign. R represents a hydrogen atom or a monovalent substituent. A 11 Each of these independently represents a divalent aromatic ring group which may have substituents, or a divalent alicyclic group which may have substituents. Z 12 and Z 13 Each of these is independently a single bond, -CR 2 CR 2 -, -CR=CR-, -C≡C-, -CR 2 O-, -CR 2 S-, -CR 2 NR-, -CR 2 CO-, -CR 2 CS-, -COO-, -COS-, -CONR-, -COCO-, -COCS-, -CSO-, -CSS-, -CSNR-, -CSCS-, -CR=N-, or a linking group formed by combining two or more of these. However, Z 13 is, -CR 2 O-CONR-, -CR 2 O-CSNR-, -CR 2 S-CONR-, -CR 2 S-CSNR-, -CR 2 NR-CONR- or -CR 2 NR-CSNR- is not used, and also -CR 2 O-CONR-, -CR 2 O-CSNR-, -CR 2 S-CONR-, -CR 2 S-CSNR-, -CR 2 NR-CONR- and -CR 2 The linking group does not include a group selected from the group consisting of NR-CSNR-. R represents a hydrogen atom or a monovalent substituent. A 12 and A 13 Each of these independently represents a divalent aromatic ring group which may have substituents. However, A 12 If it is a 6-membered ring, A 12 Z that combines with 11 or Z 12 And, Z 13 This means it bonds at the para position. A 13 If it is a 6-membered ring, then Z 13 and X 11 This means it binds at the para position. n 11 This represents an integer between 0 and 4. X 11 This represents a divalent linking group represented by either formula (X1) or formula (X2). In formula (X1), Q 1 represents -O-, -S-, or -NR-. R represents a hydrogen atom or a monovalent substituent. Q 2 The '-' represents -O-, -S-, -NR-, or a single bond. R represents a hydrogen atom or a monovalent substituent. * is A 13 This indicates the bonding position with R. 12 This indicates the connection point with [the other element]. In formula (X2), Cy 1 This represents a ring having at least one nitrogen atom and at least one carbon atom as ring member atoms, which may have substituents. * is A 13 This indicates the bonding position with R. 12 This indicates the connection point with [the other element].
2. In the above formula (X1), Q 1 However, it represents -NR-, Q 2 The compound according to claim 1, wherein the compound represents -O-, -S-, or -NR-.
3. In the above formula (1), Z 13 The compound according to claim 1 or 2, wherein the linking group is a single bond, -CR=CR-, -C≡C-, -CR=N-, or a combination of two or more of these.
4. In the above formula (1), A 11 A 12 , and A 13 The compound according to claim 1 or 2, wherein each independently represents a divalent ring group represented by any of formulas (1-1) to (1-6). 【Chemistry 2】 In formulas (1-1) to (1-6), W 1 Each is independent of the other, =CR 1 It represents - or =N-. Y 1 Each of them independently, -NR 1 It represents -, -O-, or -S-. R 1 represents a hydrogen atom or a monovalent substituent. * indicates the joining position.
5. In the above formula (1), A 11 A 12 , and A 13 The compound according to claim 1 or 2, wherein each independently represents a substituted 1,4-phenylene group or a substituted 2,6-naphthylene group.
6. In the above formula (1), Z 11 The compound according to claim 1 or 2, wherein the compound represents -O- or -S-.
7. The compound according to claim 1 or 2, wherein the polymerizable group P in formula (1) represents a radical polymerizable group containing an unsaturated double bond.
8. The compound according to claim 1 or 2, wherein in formula (1), the polymerizable group P represents a polymerizable group represented by any of formulas (P-31) to (P-42). 【Transformation 3】 X 1 Each of these independently represents either an oxygen atom or a sulfur atom. X 2 is -O-, -S-, or -NR 42 It represents -. R 42 Each of these independently represents a hydrogen atom, a halogen atom, or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, and the hydrogen atom in the aliphatic hydrocarbon group may be replaced by a halogen atom, and the -CH in the aliphatic hydrocarbon group 2 - can be -O-, -S-, -NR-, -CO-, -CS-, -SO-, or -SO 2 It can be replaced with a hyphen. R represents a hydrogen atom or a monovalent substituent. * indicates the joining position.
9. The compound according to claim 8, wherein the polymerizable group P represents a polymerizable group represented by formula (P-31).
10. The compound according to claim 1 or 2, wherein formula (1) has two or more polymerizable groups P.
11. In the above formula (1), R 11 and R 12 The compound according to claim 1 or 2, wherein each represents a monovalent substituent containing a polymerizable group P.
12. In the above formula (1), R 11 This represents a polymerizable group P, and R 12 This represents a monovalent substituent represented by formula (3), or R 12 ga-L 12 - Represents a monovalent substituent represented by a polymerizable group P, and R 11 This represents a monovalent substituent represented by formula (3), L 12 The compound according to claim 1 or 2, wherein the compound represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. However, the -CH in the alkylene group 2 - is -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO 2 -, or -C (=CH 2 ) may be replaced by - (CH in the alkylene group) 2 ) 2 The - can be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the alkylene group can be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. 【Chemistry 4】 In formula (3), L 31 and L 32 each independently represent a single bond, or a linear or branched alkylene group having 20 or less carbon atoms. -CH in the aforementioned alkylene group 2 - may be replaced with -O-, -S-, -NR-, -CO-, -CS-, -SO-, -SO 2 -, or -C(=CH 2 )-, - (CH in the aforementioned alkylene group 2 ) 2 - may be replaced with -CH=CH-, -C≡C-, or -CH=N-, and the hydrogen atom in the aforementioned alkylene group may be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. Z 31 and Z 32 each independently represent a single bond or a divalent linking group containing no ring structure. A 31 Each of these independently represents a divalent aromatic ring group which may have substituents, or a divalent alicyclic group which may have substituents. n 31 This represents an integer from 0 to 6. P represents the polymerizable group P. * indicates the joining position.
13. The compound according to claim 1 or 2, having liquid crystalline properties.
14. A composition comprising the compound described in any one of claims 1 to 13.
15. Furthermore, the composition according to claim 14, comprising a polymerizable liquid crystal compound.
16. The composition according to claim 15, wherein the polymerizable liquid crystal compound is a compound represented by formula (2). 【Transformation 5】 In formula (2), P 21 and P 22 Each of these independently represents a polymerizable group. L 21 and L 22 Each of these independently represents a single bond or a linear or branched alkylene group having 20 or fewer carbon atoms. The -CH in the alkylene group 2 - can be -O-, -S-, -NR-, -CO-, -CS-, -SO-, or -SO 2 - may be replaced by -(CH 2 ) 2 The - can be replaced with -CH=CH- or -C≡C-, and the hydrogen atom in the alkylene group can be replaced with a fluorine atom or a chlorine atom. R represents a hydrogen atom or a monovalent substituent. Z 21 This represents a single bond or a divalent linking group. A 21 and A 22 Each of these independently represents a divalent aromatic ring group which may have substituents, or a divalent alicyclic group which may have substituents. n 21 This represents an integer between 1 and 10.
17. n 21 Individual Z 21 The composition according to claim 16, wherein at least one of them represents -C≡C-.
18. The composition according to claim 14 or 15, having liquid crystalline properties.
19. A cured product obtained by curing the composition according to claim 14 or 15.
20. An optical anisotropy obtained by curing the composition according to claim 14 or 15.
21. An optical anisotropy obtained by curing the composition according to claim 14 or 15, An optical anisotropy having an orientation pattern in which the orientation of the optical axis derived from the compound represented by formula (1) is continuously rotated along at least one direction in the plane.
22. A light guide element comprising the optical anisotropy described in claim 21 and a light guide plate.
Citation Information
Patent Citations
Reactive mesogenic compounds and mixtures
WO2009086911A1