Electro-optical element and method for manufacturing electro-optical element

Abstract

The present invention addresses the problem of providing an electro-optical element having an electro-optical layer excellent in temporal stability of the electro-optic constant, and a method for manufacturing the electro-optical element. An electro-optical element according to the present invention has a substrate, an electro-optical layer, and an electrode, the electro-optical layer being obtained by fixing the alignment state of a composition for forming an electro-optical layer, the composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600-1200 nm, and the degree of orientation of a component derived from the liquid crystal compound in the electro-optical layer being 0.50 or more.

Description

Electro-optical element and method for manufacturing the same

[0001] The present invention relates to an electro-optical element and a method for manufacturing an electro-optical element.

[0002] In recent years, organic EO materials have been attracting attention as electro-optical (hereinafter also abbreviated as "EO") materials applicable to optical control elements (optical elements) such as optical modulators, optical switches, optical interconnects, etc., from the perspective of realizing ultrafast optical communications. For example, Patent Document 1 describes "a composition for nonlinear optical materials containing a liquid crystalline / nonlinear optically responsive compound having at least one polymerizable group and at least one nonlinear optically responsive group, and a compound having at least one photosensitive isomerization group."

[0003] Japanese Patent Application Laid-Open No. 2007-017960

[0004] The present inventors have found that when a composition containing a liquid crystalline / nonlinear optically responsive compound (liquid crystal compound) and a compound having a photosensitive isomerizable group (organic dye) described in Patent Document 1 is used as an organic EO material, the electro-optical constants of the formed electro-optical layer (hereinafter also abbreviated as "EO layer") may have insufficient stability over time, and there is room for improvement.

[0005] SUMMARY OF THE INVENTION It is therefore an object of the present invention to provide an electro-optical element having an electro-optical layer with excellent stability of electro-optical constants over time, and a method for manufacturing the electro-optical element.

[0006] As a result of intensive research aimed at solving the above-mentioned problems, the present inventors have discovered that, in an electro-optical element having an electro-optical layer, when a layer is used as the electro-optical layer, which is formed by fixing the orientation state of an electro-optical layer-forming composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm, and when the degree of orientation of the component derived from the liquid crystal compound in the electro-optical layer is 0.50 or more, an electro-optical element including an EO layer having excellent stability over time of the electro-optical constants can be obtained, and have completed the present invention. That is, the present inventors have discovered that the above-mentioned problems can be solved by the following configuration.

[0007] [1] An electro-optical element having a substrate, an electro-optical layer, and electrodes, wherein the electro-optical layer is a layer formed by fixing an orientation state of an electro-optical layer-forming composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm, and wherein a component derived from the liquid crystal compound in the electro-optical layer has a degree of orientation of 0.50 or more. [2] The electro-optical element according to [1], wherein the liquid crystal compound comprises at least one of a polymer liquid crystal compound having a repeating unit containing a mesogen group and a low molecular weight liquid crystal compound, and wherein at least one of the repeating unit containing the mesogen group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound has an aspect ratio of 2.0 or more. [3] The electro-optical element according to [1] or [2], wherein the liquid crystal compound comprises at least one of a polymer liquid crystal compound having a repeating unit containing a mesogen group and a low molecular weight liquid crystal compound, and wherein the angle θes formed between the vector of the molecular long axis and the vector of the transition dipole moment in at least one of the repeating unit containing a mesogen group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound is 30.0° or less. [4] The electro-optical element according to any of [1] to [3], wherein the angle θeg formed between the vector of the molecular long axis and the vector of the transition dipole moment in the organic dye is 10.0° or less. [5] The electro-optical element according to any of [1] to [4], wherein the liquid crystal compound comprises at least one of a polymer liquid crystal compound having a repeating unit containing a mesogen group and a low molecular weight liquid crystal compound, and wherein the polar term of the Hansen solubility parameter in at least one of the repeating unit containing a mesogen group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound is 7.0 or more. [6] The electro-optical element according to any one of [1] to [5], wherein the liquid crystal compound exhibits liquid crystallinity in a temperature range of 25 to 250° C., and the softening point of the electro-optical layer is 100° C. or higher. [7] When the softening point of the electro-optical layer is X° C., in a specific temperature range of X-30° C. to X+30° C., the melt viscosity of the electro-optical layer is 10×10 ７ ~10 x 10 ８The electro-optical element according to any one of [1] to [6], wherein the liquid crystal compound exhibits nematic or smectic liquid crystallinity. [8] The electro-optical element according to any one of [1] to [7], wherein the liquid crystal compound exhibits nematic or smectic liquid crystallinity. [9] The electro-optical element according to any one of [1] to [8], wherein the electro-optical element has an alignment layer, and the alignment layer is disposed so as to be in contact with the electro-optical layer.

[10] The electro-optical element according to [9], wherein the alignment layer has a thickness of 0.001 to 1 μm.

[11] The electro-optical element according to [9] or

[10] , wherein the alignment layer has a thickness variation of more than −5.0% and less than 5.0%.

[12] The electro-optical element according to any one of [1] to

[11] , wherein the composition for forming an electro-optical layer contains an alignment agent.

[13] The electro-optical element according to any one of [1] to

[12] , wherein the organic dye has a maximum absorption wavelength of 700 to 1200 nm.

[14] The electro-optical element according to any one of [1] to

[13] , wherein the electrode is a transparent electrode film.

[15] The electro-optical element according to any one of [1] to

[14] , wherein the electro-optical element is an optical modulation device having an optical waveguide.

[16] The electro-optical element according to

[15] , wherein the optical waveguide has a core layer and a clad layer, and the electro-optical layer is used as the core layer.

[17] The electro-optical element according to

[15] or

[16] , wherein the optical waveguide is a slot waveguide or a ridge waveguide.

[18] A method for producing an electro-optical element according to any one of [1] to

[17] , comprising a step of laminating the electro-optical layer of a transfer film having a temporary support, an alignment layer, and an electro-optical layer in this order to a substrate, and then peeling off the temporary support, wherein the electro-optical layer is a layer obtained by fixing an alignment state of a composition for forming an electro-optical layer, the composition including a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm, and wherein the degree of orientation of a component derived from the liquid crystal compound in the electro-optical layer is 0.50 or more.

[19] A method for producing an electro-optical element according to any one of [1] to

[17] , comprising: a step of applying a composition for forming an electro-optical layer, the composition including a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm, to form a coating film; a step of orienting the liquid crystal compound and the organic dye contained in the coating film to obtain an electro-optical layer; a first curing step of curing the electro-optical layer; and a second curing step of further curing the electro-optical layer after the first curing step, wherein a poling treatment is performed on the electro-optical layer after the first curing step and before the second step, or the curing treatment in the second curing step is performed together with the poling treatment.

[0008] According to the present invention, it is possible to provide an electro-optical element having an electro-optical layer with excellent stability of electro-optical constants over time, and a method for manufacturing the electro-optical element.

[0009] The present invention will be described in detail below. The following description of the components may be based on representative embodiments of the present invention, but the present invention is not limited to such embodiments.

[0010] In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the upper and lower limits. In this specification, in a numerical range described in stages, the upper or lower limit described in a certain numerical range may be replaced with the upper or lower limit of another numerical range described in stages. In addition, in a numerical range described in this specification, the upper or lower limit described in a certain numerical range may be replaced with a value shown in an example.

[0011] Furthermore, in this specification, parallel, orthogonal, horizontal, and vertical do not mean parallel, orthogonal, horizontal, and vertical in the strict sense, but rather mean a range of parallel ±10°, a range of orthogonal ±10°, a range of horizontal ±10°, and a range of vertical ±10°, respectively.

[0012] In addition, in this specification, each component may be a single substance corresponding to the component, or two or more substances may be used in combination. Here, when two or more substances are used in combination for each component, the content of the component refers to the total content of the substances used in combination, unless otherwise specified.

[0013] In addition, in this specification, the bonding direction of the divalent group (for example, —O—CO—) is not particularly limited. １ -L ２ -L ３ In the bond ２ When is —O—CO—, L １ The position where it is bonded to the side is *1, L ３ If the position bonded to the side is *2, then L ２ may be *1-O-CO-*2 or *1-CO-O-*2.

[0014] In addition, in this specification, "(meth)acrylate" is a notation representing "acrylate" or "methacrylate", "(meth)acrylic" is a notation representing "acrylic" or "methacrylic", and "(meth)acryloyl" is a notation representing "acryloyl" or "methacryloyl".

[0015] In this specification, examples of the substituent (monovalent substituent) include the substituents described below in Substituent Group A. In this specification, the phrase "optionally having a substituent" includes not only an embodiment in which no substituent is present, but also an embodiment in which one or more substituents are present. <Substituent Group A> Examples of the substituent include halogen atoms (for example, fluorine atoms, chlorine atoms, and bromine atoms, preferably chlorine atoms and fluorine atoms, and more preferably fluorine atoms); alkyl groups (preferably linear, branched, or cyclic alkyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as linear alkyl groups having 1 to 6 carbon atoms (for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl groups), branched alkyl groups having 3 to 6 carbon atoms (for example, isopropyl, isobutyl, tert-butyl, sec-butyl, neopentyl, isohexyl, and 3-methylpentyl groups), and cyclic alkyl groups having 3 to 12 carbon atoms (for example, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl groups); alkenyl groups (preferably alkenyl groups having 2 to 48 carbon atoms, more preferably 2 to 18 carbon atoms, such as vinyl groups, allyl groups, 1-butenyl groups, and 2-butenyl groups); alkynyl groups (preferably alkynyl groups having 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, such as ethynyl groups, 1-propynyl groups, propargyl groups, 1-butynyl groups, and 2-butynyl groups); aryl groups (preferably aryl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, such as phenyl groups, oligoaryl groups (naphthyl groups, anthryl groups), phenanthrenyl groups, fluorenyl groups, pyrenyl groups, triphenylenyl groups, and biphenyl groups); Heteroaryl groups (preferably heterocyclic groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a 2-thienyl group, a 4-pyridyl group, a 2-furyl group, a 2-pyrimidinyl group, a 1-pyridyl group, a 2-benzothiazolyl group, a 1-imidazolyl group, a 1-pyrazolyl group, or a benzotriazol-1-yl group);arylalkyl groups (preferably arylalkyl groups having 7 to 15 carbon atoms, for example, benzyl group, phenethyl group, methylbenzyl group, phenylpropyl group, 1-methylphenylethyl group, phenylbutyl group, 2-methylphenylpropyl group, tetrahydronaphthyl group, naphthylmethyl group, naphthylethyl group, indenyl group, fluorenyl group, anthracenylmethyl group (anthrylmethyl group), phenanthrenylmethyl group (phenanthrylmethyl group)); silyl groups (preferably silyl groups having 3 to 38 carbon atoms, more preferably 3 to 18 carbon atoms, for example, trimethylsilyl group, triethylsilyl group, tributylsilyl group, t-butyldimethylsilyl group, t-hexyldimethylsilyl group); hydroxy groups; cyano groups; nitro groups; morpholino groups; Alkoxy groups (preferably alkoxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methoxy, ethoxy, 1-butoxy, 2-butoxy, isopropoxy, t-butoxy, dodecyloxy, and cycloalkyloxy groups (for example, cyclopentyloxy and cyclohexyloxy)); aryloxy groups (preferably aryloxy groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenoxy and 1-naphthoxy); alkenyloxy groups (preferably alkenyloxy groups having 2 to 6 carbon atoms, for example, vinyloxy, 1-propenyloxy, 2-n-propenyloxy (allyloxy), 1-n-butenyloxy, and prenyloxy); heterocyclic oxy groups (preferably heterocyclic oxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a 1-phenyltetrazole-5-oxy group or a 2-tetrahydropyranyloxy group); silyloxy groups (preferably silyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a trimethylsilyloxy group, a t-butyldimethylsilyloxy group or a diphenylmethylsilyloxy group); acyloxy groups (preferably acyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, such as an acetoxy group, a pivaloyloxy group, a benzoyloxy group, a dodecanoyloxy group, an acryloyloxy group or a methacryloyloxy group);hydroxyalkyleneoxy groups (preferably hydroxyalkyleneoxy groups having 2 to 10 carbon atoms, for example, a hydroxyethyleneoxy group); alkoxycarbonyloxy groups (preferably alkoxycarbonyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or a cycloalkyloxycarbonyloxy group (for example, a cyclohexyloxycarbonyloxy group)); aryloxycarbonyloxy groups (preferably aryloxycarbonyloxy groups having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonyloxy group); carbamoyloxy groups (preferably carbamoyloxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, an N,N-dimethylcarbamoyloxy group, an N-butylcarbamoyloxy group, an N-phenylcarbamoyloxy group, or an N-ethyl-N-phenylcarbamoyloxy group); sulfamoyloxy groups (preferably sulfamoyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, such as an N,N-diethylsulfamoyloxy group or an N-propylsulfamoyloxy group); alkylsulfonyloxy groups (preferably alkylsulfonyloxy groups having 1 to 38 carbon atoms, more preferably 1 to 24 carbon atoms, such as a methylsulfonyloxy group, a hexadecylsulfonyloxy group or a cyclohexylsulfonyloxy group); arylsulfonyloxy groups (preferably arylsulfonyloxy groups having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, such as a phenylsulfonyloxy group); acyl groups (preferably acyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as a formyl group, an acetyl group, an acryloyl group, a methacryloyl group, a pivaloyl group, a benzoyl group, a tetradecanoyl group or a cyclohexanoyl group); an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, an octadecyloxycarbonyl group, a cyclohexyloxycarbonyl group, or a 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl group);an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, such as a phenoxycarbonyl group); a carbamoyl group (preferably a carbamoyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as a carbamoyl group, N,N-diethylcarbamoyl group, N-ethyl-N-octylcarbamoyl group, N,N-dibutylcarbamoyl group, N-propylcarbamoyl group, N-phenylcarbamoyl group, N-methyl-N-phenylcarbamoyl group, or N,N-dicyclohexylcarbamoyl group); an amino group (preferably an amino group having 32 or less carbon atoms, more preferably 24 or less carbon atoms, such as an amino group, methylamino group, N,N-dimethylamino group, N,N-dibutylamino group, tetradecylamino group, 2-ethylhexylamino group, or cyclohexylamino group); anilino group (preferably an anilino group having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, an anilino group, an N-methylanilino group); heterocyclic amino group (preferably a heterocyclic amino group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, a 4-pyridylamino group); carbonamido group (preferably a carbonamido group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, an acetamido group, a benzamido group, a tetradecanamido group, a pivaloylamido group, a cyclohexanamido group); ureido group (preferably a ureido group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a ureido group, an N,N-dimethylureido group, an N-phenylureido group); imido group (preferably an imido group having 36 or less carbon atoms, more preferably 24 or less carbon atoms, for example, an N-succinimido group, an N-phthalimido group); an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an octadecyloxycarbonylamino group, or a cyclohexyloxycarbonylamino group); an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonylamino group);sulfonamido groups (preferably sulfonamido groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methanesulfonamido groups, butanesulfonamido groups, benzenesulfonamido groups, hexadecanesulfonamido groups, and cyclohexanesulfonamido groups); sulfamoylamino groups (preferably sulfamoylamino groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, N,N-dipropylsulfamoylamino groups, and N-ethyl-N-dodecylsulfamoylamino groups); azo groups (preferably azo groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, phenylazo groups and 3-pyrazolylazo groups); alkylthio groups (preferably alkylthio groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylthio groups, ethylthio groups, octylthio groups, and cyclohexylthio groups); an arylthio group (preferably an arylthio group having 6 to 48 carbon atoms, more preferably an arylthio group having 6 to 24 carbon atoms, for example, a phenylthio group); a heterocyclic thio group (preferably a heterocyclic thio group having 1 to 32 carbon atoms, more preferably a heterocyclic thio group having 1 to 18 carbon atoms, for example, a 2-benzothiazolylthio group, a 2-pyridylthio group, or a 1-phenyltetrazolylthio group); an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 32 carbon atoms, more preferably an alkylsulfinyl group having 1 to 24 carbon atoms, for example, a dodecanesulfinyl group); an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 32 carbon atoms, more preferably an arylsulfinyl group having 6 to 24 carbon atoms, for example, a phenylsulfinyl group); alkylsulfonyl groups (preferably alkylsulfonyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, isopropylsulfonyl, 2-ethylhexylsulfonyl, hexadecylsulfonyl, octylsulfonyl, and cyclohexylsulfonyl groups); arylsulfonyl groups (preferably arylsulfonyl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenylsulfonyl, and 1-naphthylsulfonyl groups);sulfamoyl groups (preferably sulfamoyl groups having 32 or less carbon atoms, more preferably 24 or less carbon atoms, for example, a sulfamoyl group, an N,N-dipropylsulfamoyl group, an N-ethyl-N-dodecylsulfamoyl group, an N-ethyl-N-phenylsulfamoyl group, an N-cyclohexylsulfamoyl group, or an N-(2-ethylhexyl)sulfamoyl group); phosphonyl groups (preferably phosphonyl groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a phenoxyphosphonyl group, an octyloxyphosphonyl group, or a phenylphosphonyl group); phosphinoylamino groups (preferably phosphinoylamino groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a diethoxyphosphinoylamino group, or a dioctyloxyphosphinoylamino group); epoxy groups; —NHCOCH; ３ ;-SO ２ NHC ２ H ４ OCH ３ ;-NHSO ２ CH ３ and the like, and two or more of these may be combined. These substituents may be further substituted with other substituents. When two or more substituents are present, they may be the same or different. If possible, they may be bonded to each other to form a ring.

[0016] [Electro-optical element] The electro-optical element of the present invention (hereinafter also referred to as "the present EO element") is an electro-optical element having a substrate, an electro-optical layer, and electrodes, wherein the electro-optical layer is a layer formed by fixing the orientation state of an electro-optical layer-forming composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm, and the degree of orientation of the component derived from the liquid crystal compound in the electro-optical layer is 0.50 or more.

[0017] The electro-optical layer (hereinafter also referred to as "EO layer") of this EO element exhibits excellent stability of electro-optical constants over time. While the details of the reason for this are unclear, it is generally assumed as follows. When forming the EO layer, the EO layer may be cured by a curing process such as exposure to light. For example, if the EO layer contains a photopolymerization initiator, the EO layer may be cured by irradiating it with light (e.g., an i-line with a wavelength of 365 nm or an h-line with a wavelength of 406 nm) that matches the maximum absorption wavelength of the photopolymerization initiator (e.g., 350 to 400 nm). In this case, if the maximum absorption wavelength of the organic dye contained in the EO layer is low (specifically, less than 600 nm), the organic dye may absorb the light used to cure the EO layer, resulting in insufficient curing of the EO layer. As a result, the orientation of the organic dye may not be sufficiently fixed, resulting in poor stability of the electro-optical constants over time. To address this issue, the organic dye contained in the EO layer of this EO element has a maximum absorption wavelength of 600 to 1200 nm. This makes it difficult for the organic dye to absorb the light used in the curing process of the EO layer, which is thought to have effectively fixed the orientation of the organic dye. As a result, it is thought that the stability of the electro-optic constants over time has improved.

[0018] Furthermore, if the degree of orientation of the component derived from the liquid crystal compound in the EO layer is less than 0.50, the degree of orientation of the organic dye in the EO layer tends to decrease. This may cause the organic dye to form aggregates, aggregate, or crystallize more easily. As a result, the EO layer is likely to deteriorate from the nuclei of the aggregates and crystals, leading to a decrease in the electro-optical constant over time. In contrast, in the present EO element, the degree of orientation of the component derived from the liquid crystal compound in the EO layer is high, making the above-mentioned problems less likely to occur, and therefore improving the stability of the electro-optical constant over time.

[0019] The EO element can be used in optical modulation devices, optical switches, optical interconnects, etc., with an optical modulation device being preferred. The optical modulation device has an optical waveguide. The optical waveguide has a core layer and a clad layer and functions as a phase modulation section. The EO layer of the EO element is preferably used as a core layer or a clad layer, and more preferably as a core layer.

[0020] Specific examples of the optical waveguide structure include a slot waveguide, a ridge waveguide, an inverted ridge waveguide, and a channel waveguide, among which a slot waveguide or a ridge waveguide is preferred. An example of a slot waveguide is a waveguide in which an EO material (the EO layer of the present EO element) is disposed between two electrodes disposed on a substrate. Specific examples of the slot waveguide structure include the slot waveguide described in FIG. 4 of JP 2021-043263 A. An example of a ridge waveguide is a waveguide having a substrate, a lower electrode disposed on the substrate, a lower clad layer disposed on the surface of the lower electrode, a core layer (the EO layer of the present EO element) disposed on a portion of the upper surface of the lower clad layer, an upper clad layer disposed on the lower clad layer so as to bury the core layer, and an upper electrode disposed on the upper clad layer. A specific example of the structure of the ridge waveguide is the ridge waveguide shown in FIG. 1 of Japanese Patent Application Laid-Open No. 2005-010355.

[0021] [Substrate] The substrate of the present EO element is not particularly limited, and may be, for example, a conventionally known substrate such as a glass substrate, a metal substrate, a ceramic substrate, a semiconductor substrate, or a circuit substrate. A semiconductor substrate is preferable. Specific examples of the semiconductor substrate include a silicon (Si) substrate and a silicon dioxide (SiO ２ ) substrate, gallium arsenide (GaAs) substrate, indium phosphide (InP) substrate, gallium phosphide (GaP) substrate, gallium nitride (GaN) substrate, gallium telluride (GaTe) substrate, zinc selenium (ZnSe) substrate, silicon carbide (SiC) substrate, etc.

[0022] [Electro-optical Layer] The electro-optical layer (EO layer) of the present EO element is a layer formed by fixing the alignment state of an electro-optical layer-forming composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm.

[0023] The EO layer of the present EO element is preferably a layer formed by fixing the composition for forming an electro-optical layer at a temperature at which the composition exhibits a nematic or smectic phase orientation state, because this results in a higher electro-optical constant.

[0024] The EO layer of the present EO element contains a component derived from a liquid crystal compound. The component derived from a liquid crystal compound corresponds to the liquid crystal compound in the composition for forming an electro-optical layer described below. The component derived from the liquid crystal compound contained in the EO layer is preferably fixed in its alignment state in the EO layer, and the EO layer in which the alignment state is fixed does not need to exhibit liquid crystallinity. Furthermore, when the liquid crystal compound contained in the composition for forming an electro-optical layer has a reactive group such as a polymerizable group or a crosslinkable group, the component derived from the liquid crystal compound in the EO layer may be present as a product obtained by reaction of the reactive group of the liquid crystal compound.

[0025] The degree of orientation of the component derived from the liquid crystal compound in the EO layer is 0.50 or more, preferably 0.60 or more, more preferably 0.70 or more, because the electro-optical constant becomes higher. The upper limit of the degree of orientation of the component derived from the liquid crystal compound in the EO layer is not particularly limited, but the closer to 1.0 the better. The upper limit of the degree of orientation of the component derived from the liquid crystal compound in the EO layer is preferably 0.99 or less, and often 0.98 or less, from the viewpoint of practical production feasibility. The degree of orientation of the component derived from the liquid crystal compound in the EO layer is measured according to the method described in the Examples section below.

[0026] The content of the component derived from the liquid crystal compound in the EO layer is the same as the content of the liquid crystal compound relative to the total mass of the solid content of the present composition, which will be described later.

[0027] The EO layer of the EO element contains an organic dye. When the organic dye contained in the composition for forming an electro-optical layer has a reactive group such as a polymerizable group or a crosslinkable group, the organic dye in the EO layer may be present as a product obtained by reaction of the reactive group of the organic dye.

[0028] The degree of orientation of the organic dye in the EO layer is preferably 0.30 or more, more preferably 0.40 or more, and even more preferably 0.50 or more, from the viewpoint of reducing power consumption. The upper limit of the degree of orientation of the organic dye in the EO layer is not particularly limited, but the closer to 1.0 the better. The upper limit of the degree of orientation of the organic dye in the EO layer is usually 0.99 or less in many cases. The degree of orientation of the organic dye in the EO layer is measured according to the method described in the Examples section below.

[0029] The content of the organic dye in the EO layer is the same as the content of the organic dye relative to the total mass of the solid content of the present composition, which will be described later.

[0030] The orientation state of the component derived from the liquid crystal compound and the organic dye in the EO layer is preferably horizontal or vertical, and more preferably vertical. In this specification, "horizontal orientation" refers to a state in which the major surface of the EO layer is parallel to the long axis direction of the component derived from the liquid crystal compound or the organic dye. Strict parallelism is not required, and in this specification, it refers to an orientation in which the angle between the long axis direction of the component derived from the liquid crystal compound or the organic dye and the major surface of the EO layer is 0 to 10°. In addition, in this specification, "vertical orientation" refers to a state in which the major surface of the EO layer is perpendicular to the long axis direction of the component derived from the liquid crystal compound or the organic dye. Strict perpendicularity is not required, and in this specification, it refers to an orientation in which the angle between the long axis direction of the component derived from the liquid crystal compound or the organic dye and the major surface of the EO layer is 80 to 90°.

[0031] The softening point of the EO layer is preferably 100°C or higher, more preferably 110°C or higher, and even more preferably 120°C or higher. Taking into account the manufacturing process of the EO layer, the upper limit of the softening point of the EO layer is preferably 180°C or lower, and more preferably 150°C or lower. In this specification, the softening point refers to the temperature at which a substance transitions from solid to liquid, and the temperature at which the viscosity rapidly decreases from the plateau region in melt viscosity measurement. Here, the softening point is determined by calculating the rate of change of viscosity with respect to the temperature gradient. Specifically, the temperature change of the viscosity of the EO layer is measured using the method described in the Examples section below, and a graph is obtained in which the horizontal axis represents temperature and the vertical axis represents viscosity. Based on the obtained graph, the change in viscosity with respect to a small change in temperature is differentiated to determine the point at which the viscosity rapidly decreases, and the point at which the differential value having an extreme value is taken as the point at which the viscosity rapidly decreases, and this is taken as the softening point.

[0032] In one preferred embodiment of the present invention, when the softening point of the EO layer is X°C, the melt viscosity of the EO layer is 10×10 in a specific temperature range from X−30°C to X+30°C. ７ ~10 x 10 ８ In one embodiment, the EO layer has a temperature range where the viscosity is 0.05 MPa s. This allows the poling treatment described below to be carried out satisfactorily, thereby increasing the electro-optic constant of the EO layer. The melt viscosity (the viscosity of the EO layer near its softening point) is measured according to the method described in the Examples section below.

[0033] The thickness of the EO layer is preferably 0.1 to 5.0 μm, more preferably 0.5 to 3.0 μm, in the case of a ridge waveguide. The thickness of the EO layer is preferably 0.01 to 2.0 μm, more preferably 0.05 to 0.5 μm, in the case of a slot waveguide. Here, the thickness of the EO layer is calculated as the average value of measurements taken at any five points using a surface roughness meter (for example, P-10 (manufactured by TENCOR Corporation)).

[0034] <Composition for forming electro-optical layer> The composition for forming an electro-optical layer (hereinafter also referred to as "the composition") used to form the EO layer of the present EO element contains a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm. Hereinafter, each component that can be contained in the composition for forming an electro-optical layer used to form the EO layer of the present EO element will be described.

[0035] (Liquid Crystal Compound) The liquid crystal compound contained in this composition is a liquid crystal compound that does not exhibit ferroelectricity. Here, ferroelectricity refers to the property of being able to maintain electric polarization even in the absence of an external electric field and to reverse the polarity of electric polarization in response to an external electric field. In the present invention, the presence or absence of ferroelectricity is determined using the following method and evaluation criteria. - Measurement of Polarization Reversal and Residual Polarization A liquid crystal compound is sealed in an 8 μm gap liquid crystal cell (manufactured by EHC Corporation) with glass substrates with indium tin oxide (ITO) on the top and bottom. In the liquid crystal phase of the sealed liquid crystal compound, a triangular wave of 80 Hz, offset voltage 0 V, and amplitude ±10 V is applied to the cell, and the polarization reversal current and electric flux density corresponding to the applied voltage are measured. The spontaneous polarization Ps is calculated from the area of ​​the polarization reversal peak, and the remanent polarization Pr is calculated from the value of the electric flux density when the electric field becomes 0. The presence or absence of ferroelectricity is determined using the following evaluation criteria. Evaluation criteria Ferroelectricity: Both spontaneous polarization Ps and remnant polarization Pr are calculated. No ferroelectricity: At least one of spontaneous polarization Ps and remnant polarization Pr is not calculated.

[0036] The liquid crystal compound contained in the composition is preferably a liquid crystal compound exhibiting nematic or smectic liquid crystallinity. Here, "liquid crystal compound exhibiting nematic liquid crystallinity" refers to a liquid crystal compound capable of exhibiting a nematic liquid crystal state. The nematic phase refers to a state in which the constituent molecules have orientational order but no three-dimensional positional order. Furthermore, "liquid crystal compound exhibiting smectic liquid crystallinity" refers to a liquid crystal compound capable of exhibiting a smectic liquid crystal state. The smectic phase refers to a state in which molecules aligned in one direction have a layer structure.

[0037] From the viewpoint of improving the handleability and coatability of the EO layer, the liquid crystal compound contained in the composition preferably exhibits liquid crystallinity in a temperature range of 25 to 250° C., and more preferably in a temperature range of 30 to 180° C. Here, one preferred embodiment of the present invention is an embodiment in which the liquid crystal compound contained in the composition exhibits liquid crystallinity in a temperature range of 25 to 250° C., and the EO layer has a softening point of 100° C. or higher. This allows the poling treatment described below to be carried out well, and the electro-optic constant of the EO layer can be further increased.

[0038] The liquid crystal compound contained in the composition preferably contains at least one of a polymer liquid crystal compound having a repeating unit containing a mesogenic group (hereinafter also referred to as "repeating unit L") and a low molecular weight liquid crystal compound. That is, the composition may contain only one of a low molecular weight liquid crystal compound and a polymer liquid crystal compound, or may contain both a low molecular weight liquid crystal compound and a polymer liquid crystal compound. The low molecular weight liquid crystal compound and the polymer liquid crystal compound may each be used alone or in combination of two or more. Here, "low molecular weight liquid crystal compound" refers to a liquid crystal compound that does not have a repeating unit in its chemical structure. The term "polymer liquid crystal compound" refers to a liquid crystal compound that has a repeating unit in its chemical structure, and in the present invention, refers to a liquid crystal compound that has a repeating unit containing a mesogenic group. The weight-average molecular weight (Mw) of the polymer liquid crystal compound is not particularly limited, but is preferably 5,000 to 500,000, more preferably 7,000 to 300,000, and even more preferably 10,000 to 200,000. Here, the weight-average molecular weight in the present invention is a value measured by gel permeation chromatography (GPC) under the following conditions: Solvent (eluent): THF (tetrahydrofuran) Apparatus name: TOSOH HLC-8320GPC Column: Three TOSOH TSKgel Super HZM-H (4.6 mm x 15 cm) columns connected together Column temperature: 40°C Sample concentration: 0.1% by mass Flow rate: 1.0 ml / min Calibration curve: A calibration curve using seven samples of TSK standard polystyrene manufactured by TOSOH with Mw = 2,800,000 to 1,050 (Mw / Mn = 1.03 to 1.06) was used.

[0039] In the present invention, examples of low molecular weight liquid crystal compounds include the liquid crystal compounds described in paragraphs

[0072] to

[0088] of JP 2013-228706 A, and among these, liquid crystal compounds exhibiting smectic properties are preferred. Examples of polymer liquid crystal compounds include the thermotropic liquid crystal polymers described in JP 2011-237513 A, and the polymer liquid crystal compounds described in paragraphs

[0012] to

[0042] of WO 2018 / 199096 A. Examples of such liquid crystal compounds include those described in paragraphs

[0019] to

[0140] of WO 2022 / 014340 A, and the descriptions thereof are incorporated herein by reference.

[0040] Here, the mesogenic group refers to a group that represents the main skeleton of a liquid crystal molecule, contributing to the formation of liquid crystals. Liquid crystal molecules exhibit liquid crystallinity, which is an intermediate state (mesophase) between a crystalline state and an isotropic liquid state. Known mesogenic groups can be used as the mesogenic group. For example, see "Flussige Kristalle in Tabellen II" (VEB Deutsche Verlag fur Grundstoff Industrie, Leipzig, published in 1984), particularly pages 7 to 16, and "Liquid Crystal Handbook" edited by the Liquid Crystal Handbook Editorial Committee (Maruzen, published in 2000), particularly Chapter 3. In the present invention, the mesogenic group is preferably, for example, a group having at least one cyclic structure selected from the group consisting of an aromatic hydrocarbon group, a heterocyclic group, and an alicyclic group.

[0041] In the present invention, the monomer forming the repeating unit L of the low molecular weight liquid crystal compound or the polymer liquid crystal compound is preferably a compound represented by the following formula (3), because this allows the formation of an EO layer exhibiting a higher electro-optical constant. The polymer liquid crystal compound may have only one type of repeating unit L, or may have two or more types of repeating units L.

[0042] E1-(L1-M)n-L2-E2 (3) In the above formula (3), n represents an integer of 2 or more. M represents an aromatic ring which may have a substituent. Multiple Ms may be the same or different. L1 and L2 each independently represent a single bond or a divalent linking group. Multiple L1s may be the same or different. E1 and E2 each independently represent a hydrogen atom, an electron-withdrawing group, or a polymerizable group. However, with regard to the monomer, at least one of E1 and E2 represents a polymerizable group. At least one of E1 and E2 and the substituents which M may have represents an electron-withdrawing group.

[0043] In the above formula (3), n represents an integer of 2 or more, preferably an integer of 2 to 5, more preferably an integer of 2 to 4, and even more preferably 2 or 3.

[0044] Examples of the aromatic ring represented by M in the above formula (3) include aromatic rings having 6 to 20 carbon atoms, and specific examples include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring; and aromatic heterocycles such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring. Furthermore, examples of the substituent that M may have include the substituents described in the above-mentioned substituent group A, and among these, a substituent corresponding to an electron-withdrawing group is preferred. Examples of the electron-withdrawing group include those described in one embodiment of E1 and E2 below.

[0045] Examples of the divalent linking group represented by one embodiment of L1 and L2 in the above formula (3) include -CO-, -O-, -S-, -C(=S)-, -CR １ R ２ -, -CR ３ =CR ４ -, -CR ３ =N-, -C≡C-, -N=N-, -NR ５ or a divalent linking group formed by a combination of two or more thereof, specifically, —CO—, —O—, —CO—O—, —C(═S)O—, —CR １ R ２ -, -CR １ R２ -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 -, etc. Here, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. L1 and L2 are preferably any of a single bond, —CO—, —O—, and —CO—O—.

[0046] Examples of the polymerizable group represented by one embodiment of E1 and E2 in the above formula (3) include groups represented by the following formulas (P-1) to (P-30): As described above, when the monomer forming the repeating unit L of the polymer liquid crystal compound is a compound represented by the above formula (3), at least one of E1 and E2 represents a polymerizable group.

[0047]

[0048] In the above formulas (P-1) to (P-30), * represents the bonding position with L1 (M when L1 is a single bond) or L2 (M when L2 is a single bond) in the above formula (3). Ｐis a hydrogen atom, a halogen atom, a linear, branched or cyclic alkylene group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heterocyclic group (which may also be called a heterocyclic group), a cyano group, a hydroxy group, a nitro group, a carboxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (including an anilino group), an ammonio group, an acylamino group, an aminocarbonylamino group, an a an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfamoylamino group, an alkyl or arylsulfonylamino group, a mercapto group, an alkylthio group, an arylthio group, a heterocyclic thio group, a sulfamoyl group, a sulfo group, an alkyl or arylsulfinyl group, an alkyl or arylsulfonyl group, an acyl group, an aryloxycarbonyl group, an alkoxycarbonyl group, a carbamoyl group, an aryl or heterocyclic azo group, an imido group, a phosphino group, a phosphinyl group, a phosphinyloxy group, a phosphinylamino group, a phosphono group, a silyl group, a hydrazino group, a ureido group, a boronic acid group (-B(OH) ２ ), phosphato group (—OPO(OH) ２ ), or a sulfato group (—OSO ３ H), and a plurality of R Ｐ may be the same or different.

[0049] Examples of the electron-withdrawing group represented by one embodiment of E1 and E2 in formula (3) above include any of the groups represented by the following formulae: As described above, at least one of the substituents that E1, E2, and M may have represents an electron-withdrawing group, and examples thereof include groups represented by any of formulae (EA-1) to (EA-52) below, and among these, groups represented by any of formulae (EA-1) to (EA-33) below are preferred.

[0050]

[0051] In the above formulas (EA-1) to (EA-52) representing electron-withdrawing groups, * represents a bonding position. R represents a hydrogen atom or a substituent. na represents an integer of 0 to 5, and when na represents an integer of 2 to 5, multiple Rs may be the same or different. X represents -C(R Ｅ１１ ) (R Ｅ１２ )-, -C(=O)-, -C(=S)-, or -C(=NR Ｅ１３ )-. Ｅ１１ and R Ｅ１２ each independently represents a hydrogen atom, a halogen atom, an alkyl group, a fluoroalkyl group, an aryl group, a cyano group, or a nitro group, and —CH ２ - may be substituted with a divalent linking group, and the hydrogen atoms of the alkyl group and aryl group may be substituted with a substituent. Ｅ１３ represents a hydrogen atom or an alkyl group, and —CH ２ - may be substituted with a divalent linking group. Y is -O-, -S-, -N(R Ｅ１４ )- or -S(=O)-. Ｅ１４ represents a hydrogen atom, or an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group, each of which may have a substituent. Z represents -C(H)= or -N=.

[0052] Examples of the substituent represented by one embodiment of R in the above formula representing the electron-withdrawing group include the substituents described in the above-mentioned Substituent Group A. R in the above formula is preferably a hydrogen atom or an alkyl group.

[0053] As described above, X in the above formula representing an electron-withdrawing group is —C(R Ｅ１１ ) (R Ｅ１２ )-, -C(=O)-, -C(=S)-, or -C(=NR Ｅ１３ )-, where R Ｅ１１ and R Ｅ１２each independently represents a hydrogen atom, a halogen atom, an alkyl group, a fluoroalkyl group, an aryl group, a cyano group, or a nitro group, and —CH ２ - may be substituted with a divalent linking group, and the hydrogen atoms of the alkyl group and aryl group may be substituted with a substituent. ２ Examples of the divalent substituent substituting - include the same as the divalent linking group represented by one embodiment of L1 and L2, and examples of the substituent substituting a hydrogen atom include the substituents described in the above-mentioned Substituent Group A. Ｅ１３ represents a hydrogen atom or an alkyl group, and —CH ２ - may be substituted with a divalent linking group. ２ Examples of the divalent substituent substituting - include the same as the divalent linking group represented by one embodiment of L1 and L2.

[0054] As described above, Y in the above formula representing an electron-withdrawing group is —O—, —S—, —N(R Ｅ１４ )- or -S(=O)-. Ｅ１４ represents a hydrogen atom, or an alkyl group, an aryl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylsulfonyl group, or an arylsulfonyl group, which may have a substituent. Examples of the substituent that the alkyl group or the like may have include the substituents described in the above-mentioned substituent group A.

[0055] Repeating Unit L1 In the present invention, examples of polymeric liquid crystal compounds having a repeating unit L include polymers having a repeating unit L1 represented by the following formula (L1). The repeating unit L1 is a repeating unit containing a mesogenic group. The polymeric liquid crystal compound may have only one type of repeating unit L1, or may have two or more types of repeating units L1.

[0056] In the above formula (L1), R Ｂ１ represents a hydrogen atom or a substituent, and X represents —O—, —S—, or —NR Ｂ２ represents -, and R Ｂ２ represents a hydrogen atom or a substituent.Ｂ１ and L Ｂ２ each independently represents a single bond or a divalent linking group. Mes represents a mesogen group represented by formula (M) described later. T Ｂ１ represents a hydrogen atom or a substituent, and may be linked to the main chain of another polymeric liquid crystal compound.

[0057] In the above formula (L1), R Ｂ１ represents a hydrogen atom or a substituent. Ｂ１ Examples of the substituent represented by one embodiment of R include the substituents described in the above-mentioned Substituent Group A. Ｂ１ is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group.

[0058] In the above formula (L1), X is —O—, —S—, or —NR Ｂ２ represents -, and R Ｂ２ represents a hydrogen atom or a substituent. Ｂ２ Examples of the substituent represented by one embodiment of R include the substituents described in the above-mentioned Substituent Group A. Ｂ２ is preferably a hydrogen atom or an alkyl group. X is preferably —O— or —NR Ｂ２ It is preferably —, more preferably —O— or —NH—, and further preferably —O—.

[0059] In the above formula (L1), L Ｂ１ and L Ｂ２ each independently represents a single bond or a divalent linking group. Ｂ１ and L Ｂ２Examples of the divalent linking group represented by one embodiment of the formula (I) include a divalent aliphatic hydrocarbon group which may have a substituent, -O-, -S-, -N(Q)-, -CO-, or a group formed by combining these. Q represents a hydrogen atom or a substituent. Examples of the divalent aliphatic hydrocarbon group include an alkylene group having 1 to 10 carbon atoms, an alkenylene group having 1 to 10 carbon atoms, and an alkynylene group having 1 to 10 carbon atoms. Furthermore, examples of groups formed by combining these include groups formed by combining at least two or more selected from the group consisting of the above-mentioned divalent aliphatic hydrocarbon groups, -O-, -S-, -N(Q)-, and -CO-, and examples thereof include a divalent aliphatic hydrocarbon group -O- and a divalent hydrocarbon group -N(Q)-. L Ｂ１ L is preferably a divalent linking group formed by combining at least two or more groups selected from the group consisting of a linear alkylene group having 1 to 10 carbon atoms which may have a substituent, a branched alkylene group having 3 to 10 carbon atoms which may have a substituent, a cyclic alkylene group having 3 to 10 carbon atoms which may have a substituent, -O-, and -N(Q)-, and more preferably a divalent linking group formed by combining at least two or more groups selected from the group consisting of a linear alkylene group having 1 to 10 carbon atoms which may have a substituent, a cyclic alkylene group having 3 to 10 carbon atoms which may have a substituent, -O-, and -NH-. Ｂ２ is preferably a single bond. Examples of the substituent that the divalent aliphatic hydrocarbon group may have and the substituent represented by one embodiment of Q include the substituents described in the above-mentioned Substituent Group A.

[0060] In the above formula (B), Mes represents a mesogen group represented by the following formula (M). In the formula (M), * represents a bonding position, and m represents an integer of 2 or more. １１ and Ph １２ each independently represents an aromatic ring, and a plurality of Ph １１ may be the same or different. １１ represents a single bond or a divalent linking group, and a plurality of L １１may be the same or different.

[0061] Ph in the above formula (M) １１ and Ph １２ Examples of the aromatic ring represented by the formula (I) include aromatic rings having 6 to 20 carbon atoms, and specific examples thereof include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring; and aromatic heterocycles such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring.

[0062] In the above formula (M), n represents an integer of 2 or more, preferably an integer of 2 to 5, more preferably an integer of 2 to 4, and even more preferably 2 or 3.

[0063] L in the above formula (M) １１ Examples of the divalent linking group represented by one embodiment of the formula (I) include -CO-, -O-, -S-, -C(=S)-, and -CR １ R ２ -, -CR ３ =CR ４ -, -CR ３ =N-, -C≡C-, -N=N-, -NR ５ or a divalent linking group formed by a combination of two or more thereof, specifically, —CO—, —O—, —CO—O—, —C(═S)O—, —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 -, etc. Here, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. １１ is preferably any one of a single bond, —CO—, —O—, and —CO—O—.

[0064] In the above formula (L1), T Ｂ１ represents a hydrogen atom or a substituent, and may be linked to the main chain of another polymer liquid crystal compound. Ｂ１ Examples of the substituent represented by one embodiment of the formula (1) include the substituents described in the above-mentioned Substituent Group A, as well as the above-mentioned polymerizable groups and electron-withdrawing groups.

[0065] Specific examples of the repeating unit L1 represented by the above formula (L1) include the following.

[0066] When the polymeric liquid crystal compound has a repeating unit L (preferably, a repeating unit L1), the content of the repeating unit L (preferably, a repeating unit L1) is preferably 30 to 90 mass%, more preferably 50 to 90 mass%, and even more preferably 70 to 90 mass%, relative to the total repeating units (100 mass%) contained in the polymeric liquid crystal compound. When the content of the repeating unit L (preferably, the repeating unit L1) is within the above range, the degree of orientation of the components derived from the liquid crystal compound is further improved. The polymeric liquid crystal compound may contain one type of repeating unit L alone, or two or more types of repeating units L. When two or more types of repeating units L are contained, the content of the repeating unit L refers to the total content of the repeating units L.

[0067] Repeating Units Containing No Mesogen Group The polymeric liquid crystal compound may have a repeating unit that does not contain a mesogen group. Specific examples of repeating units that do not contain a mesogen group include the repeating unit X and repeating unit Y described below. When the polymeric liquid crystal compound has repeating units that do not contain a mesogen group, the content of the repeating units that do not contain a mesogen group is preferably more than 0% by mass and 30% by mass or less, more preferably 0.1 to 20% by mass, and even more preferably 0.1 to 15% by mass, relative to the total repeating units (100% by mass) contained in the polymeric liquid crystal compound. The repeating units that do not contain a mesogen group may be contained alone, or two or more types may be contained in the polymeric liquid crystal compound. When two or more types of repeating units that do not contain a mesogen group are contained, the content of the repeating units that do not contain a mesogen group refers to the total content of the repeating units that do not contain a mesogen group.

[0068] An example of a repeating unit that does not contain a mesogen group is a repeating unit X having a fluorine atom. Specific examples of the repeating unit X having a fluorine atom include the repeating unit F-1 described in paragraphs 0162 to 0209 of WO 2022 / 014342.

[0069] When the polymeric liquid crystal compound has a repeating unit X, the content of the repeating unit X is preferably 0.1 to 20% by mass, more preferably 5 to 15% by mass, and even more preferably 10 to 15% by mass, based on the total repeating units (100% by mass) contained in the polymeric liquid crystal compound. The repeating unit X may be contained in the polymeric liquid crystal compound as a single type, or as a combination of two or more types. When two or more types of repeating unit X are contained, the content of the repeating unit X refers to the total content of the repeating units X.

[0070] An example of a repeating unit that does not contain a mesogenic group is a repeating unit Y that has a crosslinkable group. Specific examples of the repeating unit Y include repeating units represented by the following formula Y:

[0071]

[0072] In formula (Y), R Ｙ１ , R Ｙ２ and R Ｙ３ R each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an aryl group. Ｙ１ , R Ｙ２ and R Ｙ３ Examples of the alkyl group in R include linear alkyl groups having 1 to 18 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms) and branched or cyclic alkyl groups having 3 to 18 carbon atoms (preferably 3 to 9 carbon atoms, more preferably 3 to 6 carbon atoms). Specific examples include methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, and cyclohexyl groups. Ｙ１ , R Ｙ２ and R Ｙ３ Examples of the alkenyl group in R include linear alkenyl groups having 2 to 18 carbon atoms and branched alkenyl groups having 3 to 18 carbon atoms. Specific examples include vinyl groups, aryl groups, 2-butenyl groups, and 3-pentenyl groups. Ｙ１ , R Ｙ２ and R Ｙ３The aryl group in R includes an aryl group having 6 to 30 carbon atoms (preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms). Specific examples include a phenyl group, a 2,6-diethylphenyl group, a 3,5-ditrifluoromethylphenyl group, a styryl group, a naphthyl group, and a biphenyl group. Ｙ１ , R Ｙ２ and R Ｙ３ is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.

[0073] In formula (Y), L Ｙ１ represents a single bond or —CO—, and —CO— is preferred.

[0074] In formula (Y), L Ｙ２ represents a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. The aliphatic hydrocarbon group may be linear or branched. As the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkylene group having 1 to 15 carbon atoms is preferred, and an alkylene group having 1 to 8 carbon atoms is more preferred. Specific examples of suitable groups include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group, and a heptylene group. L Ｙ２ -CH which constitutes part of the hydrocarbon group in ２ -, one or more -CH ２ Each - may be independently substituted with -O-, -C(O)O-, or a phenylene group. Ｙ２ Of the hydrogen atoms constituting a part of the hydrocarbon group in the formula (I), one or more hydrogen atoms may be substituted with —OH or the like.

[0075] In formula (Y), Q Ｙ represents a crosslinkable group. Specific examples of the crosslinkable group include a vinyl group, a butadiene group, a (meth)acryloyl group, a (meth)acrylamide group, a vinyl acetate group, a fumarate ester group, a styryl group, a vinylpyrrolidone group, maleic anhydride, a maleimide group, a vinyl ether group, an epoxy group, and an oxetanyl group.

[0076] When the polymeric liquid crystal compound has a repeating unit Y, the content of the repeating unit Y is preferably 0.1 to 10% by mass, and more preferably 0.1 to 5.0% by mass, based on the total repeating units (100% by mass) contained in the polymeric liquid crystal compound. The repeating unit Y may be contained in the polymeric liquid crystal compound as a single type, or as a combination of two or more types. When two or more types of repeating unit Y are contained, the content of the repeating unit Y refers to the total content of the repeating units Y.

[0077] Content The content of the liquid crystal compound is preferably 40 to 95% by mass, and more preferably 50 to 90% by mass, based on the total mass of the solid content of the composition.

[0078] Aspect Ratio The aspect ratio of at least one of the mesogen group-containing repeating unit of the polymer liquid crystal compound and the low molecular weight liquid crystal compound is preferably 2.0 or more, more preferably 2.0 to 5.0, and even more preferably 2.5 to 5.0, from the viewpoints of a higher electro-optical constant and better stability of the electro-optical constant over time. The aspect ratio of the mesogen group-containing repeating unit of the polymer liquid crystal compound or the aspect ratio of the low molecular weight liquid crystal compound refers to the ratio (L / D) of the length (L) to the diameter (D) of the smallest diameter cylinder inscribed by a molecule of the mesogen group-containing repeating unit of the polymer liquid crystal compound or a molecule of the low molecular weight liquid crystal compound, and the larger the aspect ratio, the more elongated the molecular shape.

[0079] Here, when the composition for forming an electro-optical layer contains both a polymer liquid crystal compound and a low molecular weight liquid crystal compound, it is preferable that the aspect ratio of either the repeating unit containing a mesogen group of the polymer liquid crystal compound or the low molecular weight liquid crystal compound satisfies the above value, and it is more preferable that the aspect ratios of both satisfy the above value in terms of higher electro-optical constants and better stability of the electro-optical constants over time.

[0080] Furthermore, when the polymer liquid crystal compound contains two or more types of repeating units containing a mesogenic group, it is preferable that the aspect ratio of at least one of the repeating units containing a mesogenic group satisfies the above-mentioned value, and it is more preferable that the aspect ratios of all of the repeating units satisfy the above-mentioned value, in terms of higher electro-optical constants and better stability of the electro-optical constants over time.

[0081] Furthermore, when two or more low-molecular-weight liquid crystal compounds are contained, it is preferable that the aspect ratio of at least one of the plurality of low-molecular-weight liquid crystal compounds satisfies the above-mentioned value, and it is more preferable that the aspect ratios of all of the low-molecular-weight liquid crystal compounds satisfy the above-mentioned value, in terms of higher electro-optical constants and better stability of the electro-optical constants over time.

[0082] The aspect ratios of the repeating unit of the polymer liquid crystal compound and the low molecular weight liquid crystal compound are values ​​calculated using the quantum chemistry calculation program Gaussian 16 under the following conditions of density functional theory, after determining the most stable conformations of the repeating unit of the polymer liquid crystal compound and the low molecular weight liquid crystal compound, using simulation software Winmostar V11.4.3 (manufactured by CrossAbility). Functional: cam-b3lyp Basis function: 6-31G(d) Solvent effect: ethyl acetate Other conditions: td = (nate = 16, root = 0)

[0083] The angle θes between the vector of the molecular long axis and the vector of the transition dipole moment In at least one of the repeating unit containing a mesogen group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound, the angle θes (hereinafter also abbreviated as "θes") between the vector of the molecular long axis and the vector of the transition dipole moment is preferably 30.0° or less, and more preferably 25.0° or less, from the viewpoints of higher electro-optical constants and superior stability of the electro-optical constants over time. The lower limit of θes is not particularly limited, but is preferably 0°.

[0084] Here, when the composition for forming the electro-optical layer contains both a polymer liquid crystal compound and a low molecular weight liquid crystal compound, it is preferable that the θes of one of the repeating units containing a mesogenic group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound satisfies the above-mentioned value, and it is more preferable that the θes of both satisfy the above-mentioned value in terms of higher electro-optical constants and better stability of the electro-optical constants over time.

[0085] Furthermore, when the polymer liquid crystal compound contains two or more types of repeating units containing a mesogenic group, it is preferable that the θes of at least one of the repeating units containing a mesogenic group satisfies the above value, and it is more preferable that the θes of all repeating units satisfies the above value in terms of a higher electro-optical constant and better stability over time of the electro-optical constant.

[0086] Furthermore, when two or more low-molecular-weight liquid crystal compounds are contained, it is preferable that the θes of at least one of the plurality of low-molecular-weight liquid crystal compounds satisfies the above-mentioned value, and it is more preferable that the θes of all of the low-molecular-weight liquid crystal compounds satisfies the above-mentioned value in terms of a higher electro-optical constant and better stability of the electro-optical constant over time.

[0087] θes refers to a value calculated using the following procedure and method. First, under the same conditions as in the calculation of the aspect ratio described above, the repeating unit containing a mesogen group of the polymer liquid crystal compound and the most stable three-dimensional structure of the low-molecular-weight liquid crystal compound are determined. Then, using the quantum chemistry calculation program Gaussian16, the excited-state energy is calculated by density functional theory under the following conditions. Functional: Cam-b3lyp Basis function: 6-31G(d) Solvent effect: acetonitrile Other conditions: td = (nate = 16, root = 0) Next, using the simulation software Winmostar V11.4.3 (manufactured by CrossAbility), the molecular long axis vector (Mx, My, Mz) and the transition dipole moment vector (Tx, Ty, Tz) are calculated. Note that if multiple transition dipole moments are present, the vector of the transition dipole moment with the largest absorption wavelength is used to calculate θes. Next, θes is calculated according to the following formulas (A) to (D). (A) Lm = (Mx^2 + My^2 + Mz^2)^(1 / 2) (B) Lt = (Tx^2 + Ty^2 + Tz^2)^(1 / 2) (C) θes = acos((Mx x Tx + My x Ty + Mz x Tz) / (Lm x Lt)) Here, Lm represents the magnitude of the molecular long axis vector, and Lt represents the magnitude of the transition dipole moment vector. Furthermore, if the calculated angle exceeds 90°, the calculated angle is subtracted from 180° to adjust it so that it is in the range of 0° or more and less than 90°, and this value is defined as θes.

[0088] Hansen Solubility Parameter The polarity term (δp) of the Hansen Solubility Parameter (hereinafter also referred to as "HSP value") of at least one of the mesogen group-containing repeating unit of the polymer liquid crystal compound and the low molecular weight liquid crystal compound is preferably 7.0 or more, more preferably 7.5 or more, in order to further improve compatibility with organic dyes. The upper limit of the polarity term (δp) is preferably 12.0 or less, in order to improve the solubility of the liquid crystal compound and to broaden the range of solvents that can well dissolve the liquid crystal compound in the preparation of this composition (composition for forming an electro-optical layer).

[0089] Here, when the composition for forming an electro-optical layer contains both a polymer liquid crystal compound and a low molecular weight liquid crystal compound, it is preferable that the polarity term (δp) of one of the repeating units containing a mesogenic group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound satisfies the above value, and it is more preferable that the polarity terms (δp) of both satisfy the above value in terms of better compatibility with the organic dye.

[0090] Furthermore, when the polymer liquid crystal compound contains two or more types of repeating units containing a mesogenic group, the arithmetic mean value of the polar terms (δp) of the respective repeating units is adopted as the polar term (δp) of the repeating unit containing a mesogenic group of the polymer liquid crystal compound.

[0091] Furthermore, when two or more low-molecular-weight liquid crystal compounds are contained, it is preferable that the aspect ratio of at least one of the plurality of low-molecular-weight liquid crystal compounds satisfies the above-mentioned value, and it is more preferable that the aspect ratios of all of the low-molecular-weight liquid crystal compounds satisfy the above-mentioned value, in terms of higher electro-optical constants and better stability of the electro-optical constants over time.

[0092] Here, details of the HSP value are described in Hansen, Charles (2007). Hansen Solubility Parameters: A User's Handbook, Second Edition. Boca Raton, Fla.: CRC Press. ISBN 9780849372483. The hydrogen bond term (δh), dispersion term (δd), and polar term (δp) of the HSP value are calculated by inputting the structural formula of the compound into the following software. As the software, HSPiP (Hansen Solubility Parameters in Practice) ver. 4.1.07 is used. When calculating the HSP value of a polymer liquid crystal compound, the structural formula of a repeating unit containing a mesogenic group is input into the above software.

[0093] Specific examples of the method for adjusting the repeating unit of the polymer liquid crystal compound and the polar term (δp) of the low molecular weight liquid crystal compound to fall within the above range include a method of introducing a specific functional group into the molecule, a method of changing the length of the side chain of the molecule, a method of introducing an aromatic ring into the molecule, a method of introducing hydrogen bonding, and the like.

[0094] (Organic Dye) The organic dye contained in the composition is an organic dye having a maximum absorption wavelength (hereinafter also referred to as "λmax") of 600 to 1200 nm. The lower limit of λmax of the organic dye is 600 nm or more, and from the viewpoint of superior stability over time of the electro-optical constant, it is preferably 630 nm or more, more preferably 650 nm or more, even more preferably 680 nm or more, and particularly preferably 700 nm or more. The upper limit of λmax of the organic dye is 1200 nm or less, and from the viewpoint of transparency (low absorption) in the central wavelength band, it is preferably 1100 nm or less, more preferably 1050 nm or less, even more preferably 1000 nm or less, and particularly preferably 900 nm or less.

[0095] Here, the above λmax refers to a value calculated after optimizing the structure of the organic dye using the quantum chemistry calculation program Gaussian 16 under the following conditions of the density functional theory: Functional: cam-b3lyp Basis function: 6-31+G(d,p) Solvent effect: None Other conditions: Polar

[0096] The organic dye is preferably a compound represented by the following formula (E1), from the viewpoints of further improving the degree of alignment, solubility in the liquid crystal compound, and ease of adjusting λmax within the above range.

[0097]

[0098] In the above formula (E1), R represents a hydrogen atom, or an alkyl group, aryl group, or heterocyclic group, which may have a substituent. Examples of the alkyl group in R include linear alkyl groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and branched or cyclic alkyl groups having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms). -CH ２- may be substituted with a divalent substituent, and specific examples of the divalent substituent include the above-mentioned L-C, among which -C(O)O- is preferred. Examples of the aryl group in R include aryl groups having 6 to 15 carbon atoms. Specific examples include a phenyl group and a naphthyl group. The heterocyclic group in R may be either aromatic or non-aromatic. Examples of atoms other than carbon constituting the heterocyclic group in R include a nitrogen atom, a sulfur atom, and an oxygen atom. When the heterocyclic group has multiple atoms other than carbon constituting the ring, these atoms may be the same or different. Specific examples of the heterocyclic group in R include a piperidinyl group, a piperazinyl group, a morpholinyl group, a pyrrolidinyl group, a pyrrolyl group, a pyrazolyl group, an indolyl group, an isoindolyl group, an azaindolyl group, a benzothiazolyl group, and a julolidinyl group. Examples of substituents that the alkyl group, aryl group, and heterocyclic group in R may have include -Z Ｈ , —OH, —OZ Ｈ , -OC(O)Z Ｈ , -OC(O)OZ Ｈ , -NZ Ｈ Z Ｈ’ , -NZ Ｈ C(O)Z Ｈ’ , -NZ Ｈ C(O)OZ Ｈ’ , -NZ Ｈ C(O)NZ Ｈ’ OZ Ｈ’’ , -SH, -SZ Ｈ is preferred. Ｈ , Z Ｈ’ and Z Ｈ’’each independently represents an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group, or -L-CL. In -L-CL, L represents a single bond or a divalent linking group. Specific examples of the divalent linking group are the same as the divalent linking group represented by one embodiment of L1 and L2 in formula (3). In -L-CL, CL represents a crosslinkable group. Specific examples of the crosslinkable group include a vinyl group, a butadiene group, a (meth)acryloyl group, a (meth)acrylamide group, a vinyl acetate group, a fumarate ester group, a styryl group, a vinylpyrrolidone group, maleic anhydride, a maleimide group, a vinyl ether group, an epoxy group, and an oxetanyl group. When n is 2 or more, the two or more R may be the same or different and may be bonded to each other to form a ring containing E1 (i.e., a ring containing E1 as a ring member atom). Specific examples of the ring containing E1 include a piperidinyl group, a piperazinyl group, a morpholinyl group, a pyrrolidinyl group, a pyrrolyl group, a pyrazolyl group, an indolyl group, an isoindolyl group, an azaindolyl group, a benzothiazolyl group, and a julolidinyl group. The ring containing E1 may have a substituent, and examples of the substituent include a hydroxy group.

[0099] In the above formula (E1), E1 represents an oxygen atom, a sulfur atom, or a nitrogen atom, and is preferably a nitrogen atom from the viewpoint of a high electro-optical constant and suitability for synthesis.

[0100] In the above formula (E1), A1 is —C(R Ａ１ ) = C(R Ａ２)-, an arylene group which may have a substituent, or a heterocyclic group which may have a substituent. Examples of the arylene group in A1 include an arylene group having 6 to 15 carbon atoms. Specific examples include a phenylene group and a naphthylene group. The heterocyclic group in A1 may be either aromatic or non-aromatic, but is preferably an aromatic heterocyclic group. Examples of atoms other than carbon constituting the heterocyclic group in A1 include a nitrogen atom, a sulfur atom, and an oxygen atom. When the heterocyclic group has multiple atoms constituting the ring other than carbon, these atoms may be the same or different. Specific examples of the heterocyclic group in A1 include a pyridylene group (pyridine-diyl group), a pyridazine-diyl group, an imidazole-diyl group, a thienylene (thiophene-diyl group), a quinolylene group (quinoline-diyl group), an isoquinolylene group (isoquinoline-diyl group), an oxazole-diyl group, a thiazole-diyl group, an oxadiazole-diyl group, a benzothiazole-diyl group, a benzothiadiazole-diyl group, a phthalimido-diyl group, a thienothiazole-diyl group, a thiazolothiazole-diyl group, a thienothiophene-diyl group, a thienoxazole-diyl group, a furan-diyl group, a dibenzofuran-diyl group, and a pyrazole-diyl group. Substituents that the arylene group and heterocyclic group in A1 may have include -Z Ｈ , —OH, —OZ Ｈ , -NZ Ｈ Z Ｈ’ , -SH, -SZ Ｈ , is preferred. Ｈ and Z Ｈ’ The definition is as above.

[0101] -C(R Ａ１ ) = C(R Ａ２ )-, where R Ａ１ and R Ａ２ each independently represents a hydrogen atom, —SH, or an alkyl group, and —CH ２ - may be substituted with a divalent substituent. Ａ１ and R Ａ２The alkyl group in the formula (I) includes a linear alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms), and a branched or cyclic alkyl group having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms). ２ - may be substituted with a divalent substituent, and specific examples of the divalent substituent include -O-, -(CH ２ ) ｇ -(g represents an integer of 1 to 10), -N(Z)-, -C(Z) ２ -C(Z') ２ -, -C(O)-, -C(O)O-, -O-C(O)O-, -C(O)N(Z)-, -S-, -S(O)-, -S(O)(O)-, -(O)S(O)O-, are preferred. Z and Z' each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom.

[0102] Here, A1 is -C(R Ａ１ ) = C(R Ａ２ )-, then R Ａ１ and R may be bonded to form a ring containing E1. ｎ -E1-A1- may form a fused ring. For example, when A1 is -C(SH)=CH-, E1 is N, and one of the two R is a phenyl group, the sulfur atom of the -SH group bonds to a carbon atom of the phenyl group to form a fused ring having a benzothiazole structure as shown below. In the following formula, R is defined as above, and * indicates the bonding position with L1 in formula (E1).

[0103]

[0104] In the formula (E1), A2 represents a single bond, or an arylene group or heterocyclic group which may have a substituent. When m is 2 or more, two or more A2 may be the same or different. Specific examples of the arylene group and heterocyclic group in A2 are the same as those of A1.

[0105] In the formula (E1), L1 and L2 each independently represent a single bond, —C(R Ｌ１ ) = C(R Ｌ２ ) -, -N=C(R Ｌ４) -, -C(R Ｌ４ )=N-, -C≡C-, or -N=N-. Ｌ１ , R Ｌ２ , and R Ｌ４ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, a thiol group, an alkyl group having 1 to 15 carbon atoms, an aryl group having 6 to 20 carbon atoms, or —O—Si(R Ｌ５ ) ３ or a group formed by combining two or more of these groups, and —CH ２ - may be substituted with a divalent substituent. Ｌ５ each independently represents a hydrogen atom, an alkyl group (preferably having 1 to 10 carbon atoms, which may be linear, branched, or cyclic), or a phenyl group. When n1 is 2 or more, adjacent L1s may be bonded to each other to form a ring, and when n2 is 2 or more, adjacent L2s may be bonded to each other to form a ring. When L1 and L2 are adjacent to each other (i.e., when A2 is a single bond), adjacent L1s and L2s may be bonded to form a ring. For example, when two adjacent L1s are both -C(R Ｌ１ ) = C(R Ｌ２ )-, R in one L1 Ｌ１ and R in the other L1 Ｌ１ are bonded to form a ring having the following structure (wherein * indicates a bonding site to another group). When L1 and L2 are adjacent to each other, or when L2 are adjacent to each other, a ring having the following structure can be formed, similar to when L1 are linked to each other. When n1 or m is 2 or more, the two or more L1s may be the same or different, and when n2 is 2 or more, the two or more L2s may be the same or different.

[0106]

[0107] In the above formula (E1), E ２ is -C(R Ｅ２１ ) (R Ｅ２２ )-, -C(=O)-, -C(=S)-, or -C(=NR Ｅ４ )-, represents. Ｅ２１ and R Ｅ２２R each independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 15 carbon atoms, a fluoroalkyl group having 1 to 8 carbon atoms, an aryl group having 1 to 20 carbon atoms, a cyano group, or a nitro group. Ｅ２１ and R Ｅ２２ -CH in the alkyl group ２ - may be substituted with a divalent substituent, and the hydrogen atoms of the alkyl group and aryl group may be substituted with a monovalent substituent. Specific examples of the divalent substituent include -O-, -C(Z)=N-, -C(O)-, -C(O)O-, -C(O)N(Z)-, -C(Z)=N-, -C(S)-, -S(O)-, and -SO ２ -, -(O)S(O)O-, -O(O)S(O)O-, -SC(O)- are preferred. Z represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom. Specific examples of the monovalent substituent include a halogen atom (particularly a fluorine atom or a chlorine atom), a cyano group, -Z Ｈ , —OH, —OZ Ｈ , -C(O)Z Ｈ , -C(O)OZ Ｈ , -OC(O)Z Ｈ , -OC(O)OZ Ｈ , -NZ Ｈ Z Ｈ’ , -NZ Ｈ C(O)Z Ｈ’ , -NZ Ｈ C(O)OZ Ｈ’ , -C(O)NZ Ｈ Z Ｈ’ , -OC(O)NZ Ｈ Z Ｈ’ , -NZ Ｈ C(O)NZ Ｈ’ OZ Ｈ’’ , -C(S)Z Ｈ , -C(O)SZ Ｈ , -SC(O)Z Ｈ , is preferred. Ｈ , Z Ｈ’ and Z Ｈ’’ The definition of R is as described above. Ｅ４ represents a hydrogen atom or an alkyl group having 1 to 15 carbon atoms, and —CH ２- may be substituted with a divalent substituent. Specific examples of the divalent substituent include -O-, -(CH ２ ) ｇ -, -N(Z)-, -C(Z) ２ -C(Z') ２ -, -C(O)-, -C(O)O-, -O-C(O)O-, -C(O)N(Z)- (Z and Z' each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom), -S-, -S(O)-, -S(O)(O)-, -(O)S(O)O-, -O(O)S(O)O-, and -SC(O)- are preferred.

[0108] In the above formula (E1), E ３ is -O-, -S-, -N(R Ｅ５ )- or -S(=O)-. Ｅ５ represents a hydrogen atom, or an alkyl group having 1 to 15 carbon atoms, an aryl group having 5 to 20 carbon atoms, an alkylcarbonyl group having 1 to 15 carbon atoms, an arylcarbonyl group having 5 to 20 carbon atoms, an alkylsulfonyl group having 1 to 15 carbon atoms, or an arylsulfonyl group having 5 to 20 carbon atoms, each of which may have a substituent. Specific examples of the substituent include -Z Ｈ , -C(O)Z Ｈ , -C(O)OZ Ｈ , -C(O)NZ Ｈ Z Ｈ’ , -C(S)Z Ｈ , -C(O)SZ Ｈ , is preferred. Ｈ and Z Ｈ’ The definition is as above.

[0109] In the above formula (E1), n ​​represents an integer of 1 or 2. When E1 is an oxygen atom or a sulfur atom, n is 1, and when E1 is a nitrogen atom, n is 2.

[0110] In the above formula (E1), n1 represents an integer of 0 to 3, and preferably an integer of 0 to 2.

[0111] In the above formula (E1), n2 represents an integer of 0 to 3, and an integer of 0 to 3 is preferred.

[0112] In the above formula (E1), m represents an integer of 0 to 4, and preferably an integer of 1 to 3.

[0113] As for the above formula (E1), a compound represented by the following formula (E1-1) or a compound represented by the following formula (E1-2) is preferred, and a compound represented by the following formula (E1-1) is more preferred, from the viewpoint of further improving the solubility and degree of alignment of the liquid crystal compound and facilitating adjustment of λmax within the above range.

[0114]

[0115] The definitions of the groups in formula (E1-1) and formula (E1-2) are the same as those in formula (E1) above.

[0116] Specific examples of organic dyes are shown below, but the organic dyes are not limited to these.

[0117]

[0118]

[0119] The content of the organic dye is preferably 5.0% by mass or more, more preferably 10% by mass or more, based on the total mass of the solid content of the composition, from the viewpoint of forming an EO layer exhibiting a higher electro-optic constant. The upper limit of the content of the organic dye is preferably 50% by mass or less, more preferably 40% by mass or less, based on the total mass of the solid content of the composition.

[0120] Second-order molecular susceptibility The second-order molecular susceptibility of organic dyes is 400,000 x 10 due to their superior electro-optical constants. －３３ esu or more is preferable, and 1,000,000 x 10 －３３ esu or more is preferable, and 2,000,000 x 10 －３３ esu or more is more preferable, and 3,000,000×10 －３３ From the viewpoint of dye stability, the second-order molecular susceptibility of the organic dye is 30,000,000×10 －３３ esu or less is preferable, 25,000,000 x 10 －３３ esu or less is more preferable, and 20,000,000 x 10 －３３Here, the second-order molecular susceptibility of the organic dye refers to a value calculated by the density functional method using the quantum science calculation program Gaussian 16 under the following conditions: Functional: M06x02 Basis function: 6-31+g(d,p) Solvent effect: chloroform Other conditions: default values ​​of Gaussian 16

[0121] Aspect Ratio The aspect ratio of the organic dye molecules is preferably 1.6 or more, more preferably 2.0 or more, and even more preferably 2.2 or more, from the viewpoint of further improving the degree of orientation of the organic dye. The upper limit of the aspect ratio of the organic dye molecules is preferably 5.0 or less, more preferably 4.0 or less, and even more preferably 3.5 or less, from the viewpoint of synthesis suitability and the degree of orientation. The aspect ratio of the organic dye molecules can be determined by the same method as the method for measuring the aspect ratio of the liquid crystal compound described above, except that an organic dye is used.

[0122] When two or more organic dyes are contained, it is preferable that the aspect ratio of at least one of the plurality of organic dyes satisfies the above value, and it is more preferable that the aspect ratios of all of the organic dyes satisfy the above value in terms of a better degree of orientation of the organic dyes.

[0123] As a method for increasing the aspect ratio of the organic dye molecule, the substituents in the minor axis direction, for example, the substituents A1 and A2 in the above formula (E1), R Ｌ１ ~R Ｌ４ , R Ｅ２１ , R Ｅ２２ , and R Ｅ４ is preferably a group having a linear structure, or if it is a branched structure, it is preferably a group having 10 or less atoms (the number of atoms here does not include the number of hydrogen atoms). Also, it is preferred that it is not a ring structure.

[0124] Angle θeg between the vector of the molecular long axis and the vector of the transition dipole moment The angle θeg between the vector of the molecular long axis and the vector of the transition dipole moment in the organic dye is preferably 10.0° or less, more preferably 8.0° or less, and even more preferably 6.0° or less, in order to further improve the degree of orientation of the organic dye. The lower limit of θeg is 0°. θeg can be determined by the same method as the method for measuring θes of the liquid crystal compound described above, except that an organic dye is used.

[0125] When two or more organic dyes are contained, it is preferable that the θeg of at least one of the multiple organic dyes satisfies the above value, and it is more preferable that the θeg of all of the organic dyes satisfies the above value in order to obtain a better degree of orientation of the organic dyes.

[0126] (Alignment Agent) The present composition preferably contains an alignment agent. This improves the alignment of the liquid crystal compound in the EO layer, thereby increasing the degree of alignment of the specific organic dye aligned along the liquid crystal compound. The alignment agent is not particularly limited, but examples thereof include surfactants. Both low-molecular-weight surfactants and polymeric surfactants can be used as the surfactant. Furthermore, polymeric surfactants and low-molecular-weight surfactants may be used in combination as the surfactant. Here, "polymeric surfactant" refers to a surfactant having a repeating unit in its chemical structure. Furthermore, "low-molecular-weight surfactant" refers to a surfactant having no repeating unit in its chemical structure.

[0127] From the viewpoint of a more excellent effect of reducing transmission loss and a further improvement in the degree of orientation, the polymer surfactant preferably has one or more repeating units (structural units) selected from the group consisting of a repeating unit represented by the following formula (F-1), a repeating unit represented by the following formula (F-2), a repeating unit represented by the following formula (S-1), a repeating unit represented by the following formula (A-1), and a repeating unit represented by the following formula (M-1). Among these, from the viewpoint of a more excellent effect of reducing transmission loss and a further improvement in the degree of orientation, it is more preferable to have both a repeating unit represented by the following formula (F-1), a repeating unit represented by the following formula (F-2), a repeating unit represented by the following formula (S), and a repeating unit represented by the following formula (A) (hereinafter also referred to as a "first structural unit") selected from the group consisting of a repeating unit represented by the following formula (M) (hereinafter also referred to as a "second structural unit").

[0128] First structural unit: Repeating unit F-1

[0129]

[0130] In formula (F-1), LF1 represents a single bond or a divalent linking group, R1 represents a hydrogen atom, a fluorine atom, a chlorine atom, or an alkyl group having 1 to 20 carbon atoms, and RF1 is a group containing at least one of the following groups: (a) a group represented by the following formula (1), (2), or (3), (b) a perfluoropolyether group, or (d) a group represented by the following formula (1-d).

[0131]

[0132] In formula (F-1), R1 is preferably a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms, and more preferably a hydrogen atom or a methyl group.

[0133] In formula (F-1), LF1 represents a single bond or a divalent linking group, and more specifically, examples thereof include a group represented by -LW-SPW-, an aromatic hydrocarbon group having 4 to 20 carbon atoms, a cyclic alkylene group having 4 to 20 carbon atoms, and a heterocyclic group having 1 to 20 carbon atoms. A linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 4 to 20 carbon atoms is preferred, and it is preferable to have -O-, -C(O)-O-, -C(O)-NH-, or -O-C(O)-. Here, SPW represents a divalent spacer group, and examples thereof include a linear, branched, or cyclic alkylene group having 1 to 50 carbon atoms, or a heterocyclic group having 1 to 20 carbon atoms. Furthermore, LW represents a single bond or a divalent linking group. Examples of the divalent linking group represented by LW include -O-, -(CH ２ ) ｇ -, - (CF ２ ) ｇ -, -Si(CH ３ ) ２ -, -(Si(CH ３ ) ２ O) ｇ -(g represents an integer of 1 to 10), -N(Z)-, -C(Z)=C(Z')-, -C(Z)=N-, -C(Z) ２ -C(Z') ２ -, -C(O)-, -C(O)O-, -O-C(O)O-, -C(O)N(Z)-, -C(Z)=C(Z')-C(O)O-, -C(Z)=C(Z')-C(O)N(Z")-, -C(Z)=C(Z')-C(O)-S-, -C(Z)=N-N=C(Z')- (Z, Z' and Z" each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom), -C≡C-, -N=N-, -S-, -S(O)-, -S(O)(O)-, -(O)S(O)O-, -O(O)S(O)O-, -SC(O)- and the like.

[0134] ...(a) Repeating unit having a group represented by formula (1), (2), or (3) When RF1 in formula (F-1) contains a group represented by formula (1), (2), or (3), formula (F-1) is also preferably a repeating unit represented by formula (4) below.

[0135]

[0136] In formula (4), Rf ａ is a group represented by the above formula (1), (2) or (3).

[0137] In formula (4), R １Ｂ is a divalent group having 2 to 50 carbon atoms. １Ｂ The divalent group having 2 to 50 carbon atoms represented by the formula (R) may contain a heteroatom, and may be an aromatic group, a heteroaromatic group, a heterocyclic group, an aliphatic group, or an alicyclic group. １Ｂ Specific examples of the group include the following:

[0138] - (CH ２ ) ｎ１ - (n1=2~50) -X-Y-(CH ２ ) ｎ２ - (n2=2~43) -X-(CH ２ ) ｎ３ - (n3=1~44) -CH ２ CH ２ (OCH ２ CH ２ ) ｎ４ - (n4=1~24) -XCO(OCH ２ CH ２ ) ｎ５ - (n5=1 to 21)

[0139] In the above formula, X represents phenylene, biphenylene, or naphthylene, which may have 1 to 3 substituents selected from the group consisting of alkyl groups having 1 to 3 carbon atoms (methyl, ethyl, or propyl), alkoxy groups having 1 to 4 carbon atoms (methoxy, ethoxy, propoxy, or butoxy), and halogen atoms (F, Cl, Br, or I). Y represents -O-CO-, -CO-O-, -CONH-, or -NHCO-. X is preferably 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene, and more preferably 1,4-phenylene.

[0140] Particularly preferred R １Ｂ Specific examples of the divalent group having 2 to 50 carbon atoms represented by the formula (I) include divalent groups having the following structures:

[0141] - (CH ２ ) ｎ１- (n1=2~10) -C ６ H ４ OCO (CH ２ ) ｎ２ - (n2=2~10) -C ６ H ４ (CH ２ ) ｎ３ - (n3=1~10) -CH ２ CH ２ (OCH ２ CH ２ ) ｎ４ - (n4=1 to 10) -C ６ H ４ CO(OCH ２ CH ２ ) ｎ５ - (n5=1 to 10)

[0142] In formula (4), R ２ is a hydrogen atom or a methyl group.

[0143] ...(b) Repeating unit having a perfluoropolyether group In the above formula (F-1), it is also preferable that RF1 has a perfluoropolyether group. The perfluoropolyether group is a divalent group in which a plurality of fluorocarbon groups are bonded via ether bonds. The perfluoropolyether group is preferably a divalent group in which a plurality of perfluoroalkylene groups are bonded via ether bonds. The perfluoropolyether group may have a linear, branched, or cyclic structure, and is preferably a linear or branched structure, and more preferably a linear structure.

[0144] When RF1 in formula (F-1) contains a repeating unit containing a perfluoropolyether group, formula (F-1) is preferably a structural unit represented by the following formula (Ib).

[0145]

[0146] In formula (I-b), LF1 represents the same group as in formula (F-1). １１ represents a hydrogen atom, a fluorine atom, a chlorine atom, or an alkyl group having 1 to 20 carbon atoms. １ and Rf ２Rf each independently represents a fluorine atom or a perfluoroalkyl group. １ When a plurality of Rf are present, they may be the same or different. ２ When a plurality of are present, they may be the same or different. u represents an integer of 1 or more. p represents an integer of 1 or more.

[0147] R １２ represents a hydrogen atom or a substituent, and the substituent is not particularly limited, but examples thereof include a fluorine atom, a perfluoroalkyl group (preferably having 1 to 10 carbon atoms), an alkyl group (preferably having 1 to 10 carbon atoms), and a hydroxyalkyl group (preferably having 1 to 10 carbon atoms). In formula (I-b), u represents an integer of 1 or more, preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 3. In formula (I-b), p represents an integer of 1 or more, preferably 1 to 100, more preferably 1 to 80, and even more preferably 1 to 60. It should be noted that when p [CRf １ Rf ２ ]uO may be the same or different.

[0148] ...(d) A group represented by formula (1-d)

[0149]

[0150] In formula (1-d), X represents a hydrogen atom or a substituent (preferably a group represented by "SP-H" above), T10 represents a terminal group (preferably the same group as T1 above), l represents an integer of 1 to 20, m represents an integer of 0 to 2, n represents an integer of 1 or 2, and m+n is 2. When l is 2 or greater, multiple -(CXmFn)- groups may be the same or different. In formula (1-d), C represents a carbon atom, and F represents a fluorine atom.

[0151] In formula (1-d), X represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cyano group, a nitro group, -OZ Ｈ , -C(O)Z Ｈ , -C(O)OZ Ｈ , -OC(O)Z Ｈ , -NZＨ Z Ｈ ', -NZ Ｈ C(O)Z Ｈ ', -NZ Ｈ C(O)OZ Ｈ ', -C(O)NZ Ｈ Z Ｈ ', -OC(O)NZ Ｈ Z Ｈ ' is preferred, and a hydrogen atom, a fluorine atom, -Z Ｈ , or -OZ Ｈ is more preferred. Ｈ and Z Ｈ Each of the ' independently represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cyano group, or a nitro group, and preferably has 1 to 4 carbon atoms.

[0152] In formula (1-d), T10 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cyano group, a nitro group, -OZ Ｈ , -C(O)Z Ｈ , -C(O)OZ Ｈ , -OC(O)Z Ｈ or the crosslinkable groups represented by the above formulas (P1) to (P30), and a hydrogen atom, a fluorine atom, an alkyl group having 1 to 10 carbon atoms, a cyano group, a nitro group, -OZ Ｈ , a vinyl group, a (meth)acryloyl group, a (meth)acrylamide group, a styryl group, a vinyl ether group, an epoxy group, or an oxetanyl group is more preferred. Ｈ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cyano group, or a nitro group, and preferably has 1 to 4 carbon atoms.

[0153] Repeating Unit F-2 Repeating unit F-2 is a repeating unit represented by the following formula (F-2).

[0154]

[0155] In formula (F-2), R2 represents a hydrogen atom, a fluorine atom, a chlorine atom, or an alkyl group having 1 to 4 carbon atoms, LF2 represents the same group as LF1 in formula (F-1) above, SP21 and SP22 each independently represent a spacer group, DF2 represents a group having a valence of (m2+1), T2 represents a terminal group, RF2 represents a group containing a fluorine atom, n2 represents an integer of 2 or more, m2 represents an integer of 2 or more, and m2≧n2. Multiple -SP22-RF2 may be the same or different. When multiple T2s are present, the multiple T2s may be the same or different.

[0156] In formula (F-2), R2 represents a hydrogen atom, a fluorine atom, a chlorine atom, or an alkyl group having 1 to 4 carbon atoms, and is preferably a hydrogen atom or a methyl group.

[0157] In formula (F-2), DF2 represents a (m2+1)-valent group, and specifically, DF2 represents a tertiary carbon atom (-C(H)<), a quaternary carbon atom (>C<), a nitrogen atom, a phosphate ester group (P(=O)(-O-) ３ ), a branched alkylene group having 2 to 20 carbon atoms, an aromatic ring having 4 to 15 carbon atoms, an aliphatic ring and a heterocycle having 4 to 15 carbon atoms, etc. The carbon atoms in the branched alkylene group, aromatic ring and aliphatic ring may be replaced with the above-mentioned "SP-C". The hydrogen atoms in the branched alkylene group, aromatic ring and aliphatic ring may be replaced with the above-mentioned "SP-H". DF2 is preferably a carbon atom (a tertiary carbon atom or a quaternary carbon atom), a nitrogen atom, a benzene ring, a cyclohexane ring or a cyclopentane ring.

[0158] SP21 and SP22 each independently represent a spacer group, preferably a single bond, or a linear, branched, or cyclic alkylene group having 1 to 10 carbon atoms. Here, the carbon atoms of the alkylene group are -O-, -S-, -N(Z)-, -C(Z)=C(Z')-, -C(O)-, -C(S)-, -OC(O)-, -OC(S)-, -SC(O)-, -C(O)O-, -C(S)O-, -C(O)S-, -O-C(O)O-, -N(Z)C(O)-, -C(O)N(Z)-, (Z and Z' each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom.) may be substituted. In addition, the hydrogen atoms of the alkylene group may be substituted with a fluorine atom or a fluoroalkyl group.

[0159] T2 is a hydrogen atom, a halogen atom, —OH, —COOH, an alkyl group having 1 to 10 carbon atoms, a cyano group, a nitro group, —OZ Ｈ , -C(O)Z Ｈ , -C(O)OZ Ｈ , -OC(O)Z Ｈ , and crosslinkable groups represented by formulae (P1) to (P30), and a hydrogen atom, a fluorine atom, —OH, —COOH, —Z Ｈ , -OZ Ｈ , a vinyl group, a (meth)acryloyl group, a (meth)acrylamide group, a styryl group, a vinyl ether group, an epoxy group, or an oxetanyl group is more preferred. Ｈ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cyano group, or a nitro group, and preferably has 1 to 4 carbon atoms.

[0160] RF2 represents a group containing a fluorine atom, and among these, a fluorine atom, RF1 in the above formula (F-1), or a group containing a fluorine atom among the above T2 is preferred.

[0161] In formula (F-2), m2 is preferably an integer of 2 to 8, and more preferably an integer of 2 to 6. n2 is preferably an integer of 2 to 4, and more preferably an integer of 2 or 3.

[0162] The repeating unit represented by formula (F-2) may be of a cleavage type that is cleaved by an acid or a base, etc., and RF2 is eliminated from the polymer side chain, thereby improving the coatability of the upper layer.

[0163] Repeating Unit S The repeating unit S is a repeating unit represented by the following formula (S).

[0164]

[0165] In formula (S), ms represents an integer of 2 or greater. ms is preferably an integer of 3 or greater, more preferably an integer of 3 to 6, and even more preferably an integer of 3 to 5.

[0166] In formula (S), R ３１ , R ３２ , and R ３３ each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. ３１ may be the same or different. ３２ may be the same or different. ３３ may be the same or different. Here, examples of the alkyl group include linear alkyl groups having 1 to 18 carbon atoms and branched or cyclic alkyl groups having 3 to 18 carbon atoms. Examples of the alkenyl group include alkenyl groups having 2 to 12 carbon atoms. Examples of the aryl group include aryl groups having 6 to 12 carbon atoms. Specific examples include phenyl groups, α-methylphenyl groups, and naphthyl groups. Examples of the alkylenearyl group include alkylenearyl groups having 7 to 30 carbon atoms.

[0167] In formula (S), R ２１ and R ２２ R each independently represents a hydrogen atom or an alkyl group. ２１ and R ２２Examples of the alkyl group represented by one embodiment of the formula (1) include linear alkyl groups having 1 to 18 carbon atoms, and branched or cyclic alkyl groups having 3 to 18 carbon atoms. Specific examples include methyl, ethyl, propyl, butyl, isopropyl, tert-butyl, and cyclohexyl groups. ２１ and R ２２ is preferably a hydrogen atom.

[0168] In formula (S), R ２３ represents a hydrogen atom or a substituent. ２３ Examples of the substituent represented by one embodiment of the formula (1) include an alkyl group, an alkenyl group, an aryl group, or a substituent having a linking group and a group containing a silicon atom. ２ -CO-L Ｓ１ -L Ｓ２ -(Si(R ３１ ) (R ３２ ) (R ３３ )) ms is also included. Ｓ１ , L Ｓ２ 、 R ３１ , R ３２ , R ３３ and ms are defined as the same as the symbols in formula (S). ２３ is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group. ２３ is preferably a hydrogen atom or a methyl group.

[0169] In formula (S), L Ｓ１ is —O— or —NR Ｚ - represents. Ｚ represents a hydrogen atom or a substituent. Ｓ１ One aspect of the invention is represented by -NR Ｚ -Regarding R Ｚ The substituent represented by one embodiment of the formula (I) is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or an ethyl group. Ｓ１ As the group, —O— or NH— is preferable, and —O— is more preferable.

[0170] In formula (S), LＳ２ represents a ms+1-valent linking group. Ｓ２ Suitable examples of the ms+1 valent linking group represented by are hydrocarbon groups having 1 to 10 carbon atoms and ms+1 valent, which may have a substituent, and in which some of the carbon atoms constituting the hydrocarbon group may be substituted with heteroatoms. Here, the substituent that the hydrocarbon group may have is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or an ethyl group. Examples of heteroatoms include a silicon atom, an oxygen atom, and a nitrogen atom. L Ｓ２ Specific examples of the formula (S1) include the formulae K-1-L, K-2-L, and K-3-L shown below. In the formulae below, * indicates L in formula (S1). Ｓ１ ** represents the bonding position of (—SiR ３１ R ３２ R ３３ ) represents the bonding position to the group represented by ms.

[0171]

[0172] Repeating Unit A Repeating unit A is a repeating unit represented by the following formula (A).

[0173]

[0174] In formula (A), R ２１ , R ２２ , and R ２３ are each defined as the same symbol in formula (S).

[0175] In formula (A), L Ａ１ represents a single bond or a divalent linking group. Ａ１ Examples of the divalent linking group represented by one embodiment of the formula (I) include -CO-, -O-, -S-, -C(=S)-, and -CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group consisting of a combination of two or more thereof. １ ~R ５each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. Among these divalent linking groups, —O—, —S—, —CO—O—, —CO—NR ５ - or -CO-S- is preferred, and -CO-O- or -CO-NR ５ - is more preferable.

[0176] In formula (A), na represents an integer of 1 to 8. na preferably represents an integer of 1 to 4, and more preferably represents 1 or 2. When na represents 1, L Ａ２ represents a single bond.

[0177] In formula (A), L Ａ２ represents a single bond or a na+1-valent linking group. Ａ２ Examples of the na+1-valent linking group represented by one embodiment of the formula (1) include an alkylene group, an ether group (—O—), a thioether group (—S—), a tertiary carbon atom, a quaternary carbon atom, and a linking group formed from a combination thereof. Specific examples include a trivalent linking group formed from a combination of an alkylene group having 1 to 6 carbon atoms, a tertiary carbon atom bonded to the alkylene group, and two ether groups bonded to the tertiary carbon atom, and a tetravalent linking group formed from a combination of an alkylene group having 1 to 6 carbon atoms, a quaternary carbon atom bonded to the alkylene group, and three ether groups bonded to the quaternary carbon atom.

[0178] In formula (A), A represents an alkyl group having 5 to 40 carbon atoms and three or more terminal methyl groups (hereinafter also referred to as a "specific alkyl group"). However, when na represents an integer of 2 to 8, the multiple A's may be the same or different. Here, a "terminal methyl group" refers to a methyl group constituting the terminal of a linear or side chain of an alkyl group. For example, linear alkyl groups such as n-propyl and n-butyl groups are alkyl groups having one terminal methyl group, an isopropyl group is an alkyl group having two terminal methyl groups, and a t-butyl group is an alkyl group having three terminal methyl groups. Therefore, for example, an n-hexyl group has six carbon atoms, but is an alkyl group having only one terminal methyl group, and therefore does not fall under the category of a specific alkyl group. On the other hand, the alkyl groups represented by the following formulae (a-1) to (a-4) all have 5 to 40 carbon atoms and three or more terminal methyl groups (methyl groups surrounded by dotted lines in the following formulae), and therefore fall under the category of a specific alkyl group.

[0179]

[0180] The number of terminal methyl groups in the specific alkyl group is preferably 3 to 15, and more preferably 3 to 10. The number of carbon atoms in the specific alkyl group is preferably 5 to 30, and more preferably 5 to 20. The ratio of the number of terminal methyl groups to the number of carbon atoms in the specific alkyl group (number of terminal methyl groups / number of carbon atoms in the specific alkyl group) is preferably 0.4 or more, and more preferably 0.4 or more and 0.6 or less. The specific alkyl group is preferably an alkyl group represented by any of the above formulas (a-1) to (a-4).

[0181] Examples of the first constitutional unit are shown below, but the first constitutional unit is not limited to the examples below.

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] Of these structural units, the first structural unit is preferably a structural unit having the repeating unit S or the repeating unit A from the viewpoint of environmental protection.

[0189] Second Structural Unit: Repeating Unit M The repeating unit M is a repeating unit represented by the following formula (M).

[0190]

[0191] In formula (M), RA1 and RA2 each independently represent a hydrogen atom or an alkyl group. Examples of the alkyl group in RA1 and RA2 include a linear alkyl group having 1 to 18 carbon atoms (preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms) and a branched or cyclic alkyl group having 3 to 18 carbon atoms (preferably 3 to 9 carbon atoms, more preferably 3 to 6 carbon atoms). Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, a tert-butyl group, a cyclohexyl group, and the like. It is preferable that both RA1 and RA2 are hydrogen atoms.

[0192] In formula (M), RA3 represents a hydrogen atom, a halogen atom, or a substituent. Specific examples of the substituent in RA3 include an alkyl group, an alkenyl group, and an aryl group. The substituent in RA3 is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or an ethyl group. RA3 is preferably a hydrogen atom or a methyl group.

[0193] In formula (M), LX represents a single bond or a divalent linking group, and more specific examples thereof include the group represented by -LW-SPW- described above, an aromatic hydrocarbon group having 4 to 20 carbon atoms, a cyclic alkylene group having 4 to 20 carbon atoms, and a heterocyclic group having 1 to 20 carbon atoms. A linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 4 to 20 carbon atoms is preferred, and one having -O-, -C(O)-O-, -C(O)-NH-, or -O-C(O)- is more preferred.

[0194] In formula (M), SPX is a divalent spacer group. The divalent spacer group in SPX is preferably a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 4 to 20 (preferably 6 to 20) carbon atoms, and the carbon atom of the alkylene group may be substituted with the above SP-C. Among the above SP-C, —O—, —Si(CH ３ ) ２ -, -(Si(CH ３ ) ２ O) ｇ -(g represents an integer of 1 to 10), -C(Z) ２ -C(Z') ２ -, -C(O)-, -C(O)O-, -O-C(O)O-, -C(O)N(Z)- (Z and Z' each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom), -S-, -S(O)-, and -S(O)(O)- are preferred.

[0195] TX represents a group represented by formula (M1) or a group represented by formula (M2).

[0196]

[0197] In the above formulas (M1) and (M2), * represents a linking site with SPX.

[0198] In the above formula (M1), TM1 represents —COOH, —CSOH, —OH, —NR Ｍ１ R Ｍ２ , -SO ３ H or PO ４ represents H, and R Ｍ１ and R Ｍ２ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. TM1 is —COOH, —NR Ｍ１ R Ｍ２ is preferred.

[0199] In the above formula (M2), m2 represents an integer of 1 to 4, M21 and M22 each independently represent an aromatic ring, an aliphatic ring or a heterocycle which may have a substituent, and when m2 is 2 or more, multiple M22 may be the same or different, LM2 represents a single bond or a divalent linking group, more specifically, represents the group represented by -LW-SPW- above, and when m2 is 2 or more, multiple LM2 may be the same or different, and TM2 represents a terminal group.

[0200] M21 and M22 each represent an aromatic ring, an aliphatic ring, or a heterocycle, which may have a substituent, and are preferably 4- to 15-membered rings. M21 and M22 may be a monocycle or a condensed ring, and a plurality of M21 and M22 may be the same or different. Examples of the aromatic ring represented by M21 and M22 include a phenylene group, a naphthylene group, a fluorene-diyl group, an anthracene-diyl group, and a tetracene-diyl group, and from the viewpoints of the diversity of mesogen skeleton designs and the availability of raw materials, a phenylene group or a naphthylene group is preferred. Examples of the aliphatic ring represented by M21 and M22 include a cyclopentylene group and a cyclohexylene group, and the carbon atom may be -O-, -Si(CH ３ ) ２ -, -N(Z)-, -C(O)-, -S-, -C(S)-, -S(O)-, and -SO ２-, or a group consisting of a combination of two or more of these groups. Z represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group, an aryl group, a cyano group, or a halogen atom. Atoms other than carbon that constitute the heterocycle represented by M21 and M22 include a nitrogen atom, a sulfur atom, and an oxygen atom. When the heterocycle has multiple atoms that constitute the ring other than carbon, these atoms may be the same or different. Specific examples of the heterocycle include a pyridylene group (pyridine-diyl group), a pyridazine-diyl group, an imidazole-diyl group, a thienylene (thiophene-diyl group), a quinolylene group (quinoline-diyl group), an isoquinolylene group (isoquinoline-diyl group), an oxazole-diyl group, a thiazole-diyl group, an oxadiazole-diyl group, a benzothiazole-diyl group, a benzothiadiazole-diyl group, a phthalimido-diyl group, a thienothiazole-diyl group, a thiazolothiazole-diyl group, a thienothiophene-diyl group, a thienoxazole-diyl group, and the following structures (II-1) to (II-4).

[0201]

[0202] In formulas (II-1) to (II-4), D １ is —S—, —O—, or NR １１ represents -, and R １１ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; １ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms; Z １ , Z ２ and Z ３ each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, or —NR １２ R １３ , or -SR １２ where Z １ and Z ２ may be bonded to each other to form an aromatic ring or an aromatic heterocycle, R １２ and R １３each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; １ and A ２ are each independently —O—, —NR ２１ - (R ２１ represents a hydrogen atom or a substituent; represents a group selected from the group consisting of -S- and CO-; E represents a non-metallic atom of Groups 14 to 16 which may have a hydrogen atom or a substituent bonded thereto; 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; Ay represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, or 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, the aromatic rings of Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring; D ２ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.

[0203] In formula (II-2), Y １ When Y is an aromatic hydrocarbon group having 6 to 12 carbon atoms, it may be monocyclic or polycyclic. １ When A is an aromatic heterocyclic group having 3 to 12 carbon atoms, it may be a monocyclic or polycyclic ring. １ and A ２ But, -NR ２１ When - represents R ２１ For the substituent, see, for example, paragraphs

[0035] to

[0045] of JP-A-2008-107767, the contents of which are incorporated herein by reference. In formula (II-2), when E is a non-metallic atom of Groups 14 to 16 which may have a substituent bonded thereto, ═O, ═S, ═NR', or ═C(R')R' is preferred. R' represents a substituent, and for the substituent, see, for example, paragraphs

[0035] to

[0045] of JP-A-2008-107767, with oxygen and sulfur atoms being preferred.

[0204] Regarding M21 and M22 in the above formula (M2), examples of the substituent that the aromatic ring, aliphatic ring, or heterocycle may have include, for example, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heterocyclic group (also referred to as a heterocyclic group), a cyano group, a hydroxy group, a nitro group, a carboxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (including an anilino group), ), ammonio group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, aryl or heterocyclic azo group, imido group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, phosphono group, silyl group, hydrazino group, ureido group, boronic acid group (-B(OH) ２ ), phosphato group (—OPO(OH) ２ ), sulfato group (—OSO ３ H), and other known substituents. Details of the substituents are described in paragraph

[0023] of JP-A-2007-234651.

[0205] LM2 represents a single bond or a divalent linking group, and among these, an alkylene group having 2 to 12 carbon atoms, a fluorinated alkylene group having 2 to 12 carbon atoms, -(OC ２ H ４ ) ｇ O-, -(OC ３ H ６ ) ｇ O-,-(Si(CH ３ ) ２ O) ｇ-, (wherein g represents an integer of 1 to 10), are preferred.

[0206] TM2 represents a terminal group. More specific examples include a hydrogen atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylsulfonyl group having 1 to 10 carbon atoms, an alkylaminocarbonyl group having 1 to 10 carbon atoms, an alkylaminosulfonyl group having 1 to 10 carbon atoms, an alkylcarbonylamino group having 1 to 10 carbon atoms, an alkoxycarbonyl group having 1 to 10 carbon atoms, a C1 to 10 alkylcarbonyloxy group, and an alkylsulfonylamino group having 1 to 10 carbon atoms, among which a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkoxycarbonyl group, and an alkylcarbonyloxy group are preferred.

[0207] Examples of the second constitutional unit are shown below, but the second constitutional unit is not limited to the examples below.

[0208]

[0209] When the polymer surfactant has the first structural unit, the content of the first structural unit is preferably 10.0 to 80.0 mass%, more preferably 15.0 to 75.0 mass%, and even more preferably 20.0 to 70.0 mass%, based on all units contained in the polymer surfactant. When the polymer surfactant has the second structural unit, the content of the second structural unit is preferably 5.0 to 80.0 mass%, more preferably 17.0 to 75.0 mass%, and even more preferably 10.0 to 70.0 mass%, based on all units contained in the polymer surfactant.

[0210] - Third Constitutional Unit When the polymer surfactant has a first constitutional unit and a second constitutional unit, the polymer surfactant may further have a unit other than the first constitutional unit and the second constitutional unit (hereinafter also referred to as a "third constitutional unit"). Specific examples of the third constitutional unit are shown below.

[0211]

[0212] When the polymer surfactant has a third constitutional unit, the content of the third constitutional unit is preferably 1.0 to 80.0 mass%, more preferably 3.0 to 75.0 mass%, and even more preferably 5.0 to 70.0 mass%, based on all units contained in the polymer surfactant.

[0213] Content The content of the alignment agent (particularly, polymer surfactant) is preferably 0.10 to 30.0 parts by mass, more preferably 0.15 to 20.0 parts by mass, and even more preferably 0.20 to 10.0 parts by mass, relative to 100 parts by mass of the organic dye. If the content of the alignment agent is 0.10 parts by mass or more, the effect of reducing transmission loss is further improved, and the degree of alignment is further improved. If the content of the alignment agent is 30.0 parts by mass or less, the electro-optical constant can be further increased.

[0214] Molecular Weight When the alignment agent is a polymer surfactant, the weight-average molecular weight (Mw) of the polymer surfactant is preferably 4,000 to 200,000, more preferably 6,000 to 100,000, and even more preferably 8,000 to 70,000. Here, the weight-average molecular weight of the polymer surfactant is a value measured by gel permeation chromatography (GPC). Solvent (eluent): tetrahydrofuran. Apparatus name: TOSOH HLC-8220GPC. Column: Three TOSOH TSKgel Super HZM-H (4.6 mm x 15 cm) columns connected together. Column temperature: 25°C. Sample concentration: 0.1% by mass. Flow rate: 0.35 ml / min. Calibration curve: A calibration curve using seven samples of TSK standard polystyrene manufactured by TOSOH with Mw = 2,800,000 to 1,050 (Mw / Mn = 1.03 to 1.06) was used.

[0215] Preferred Embodiment One preferred embodiment of the present EO element is one in which the content of the alignment agent (particularly, polymer surfactant) in the present composition is 10% by mass or more, and the absolute value of the difference in HSP value between the liquid crystal compound in the present composition and the alignment agent (particularly, polymer surfactant) is 2 or more. This makes it easier for the alignment agent to be unevenly distributed, resulting in excellent high alignment. The HSP value of the alignment agent can be calculated using the same method as the method for calculating the HSP value of a liquid crystal compound.

[0216] (Solvent) From the viewpoint of workability, etc., the present composition preferably contains a solvent. Examples of the solvent include ketones (e.g., acetone, 2-butanone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, acetylacetone, etc.), ethers (e.g., dioxane, tetrahydrofuran, tetrahydropyran, dioxolane, tetrahydrofurfuryl alcohol, cyclopentyl methyl ether, dibutyl ether, etc.), aliphatic hydrocarbons (e.g., hexane, etc.), alicyclic hydrocarbons (e.g., cyclohexane, etc.), aromatic hydrocarbons (e.g., benzene, toluene, xylene, tetralin, trimethylbenzene, etc.), halogenated carbons (e.g., dichloromethane, trichloromethane (chloroform), dichloroethane, dichlorobenzene, 1,1,2,2-tetrachloroethane, chlorotoluene, etc.), esters (e.g., methyl acetate, ethyl acetate, butyl acetate, diethyl carbonate, ethyl acetoacetate, n-pentyl acetate, ethyl benzoate, benzyl benzoate, butyl carbitol acetate, diethylene glycol monoethyl ether, etc.). acetate, isoamyl acetate, etc.), alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol, furfuryl alcohol, 2-ethylhexanol, octanol, benzyl alcohol, ethanolamine, ethylene glycol, propylene glycol, diethylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, etc.), phenols (e.g., phenol, cresol, etc.), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, 1,2-dimethoxyethane, etc.), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), amides (e.g., dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, etc.), and heterocyclic compounds (e.g., pyridine, 2,6-lutidine, etc.), as well as organic solvents such as water. These solvents may be used alone or in combination of two or more.

[0217] When the present composition contains a solvent, the content of the solvent is preferably 50.0 to 98.0 mass %, more preferably 45.0 to 95.0 mass %, and even more preferably 40.0 to 93.0 mass %, relative to the total mass of the present composition.

[0218] (Polymerization initiator) The composition of the present invention preferably contains a polymerization initiator. There are no particular limitations on the polymerization initiator, but it is preferably a photosensitive compound, i.e., a photopolymerization initiator. As the photopolymerization initiator, various compounds can be used without particular limitations. Examples of photopolymerization initiators include α-carbonyl compounds (U.S. Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (U.S. Pat. No. 2,448,828), α-hydrocarbon-substituted aromatic acyloin compounds (U.S. Pat. No. 2,722,512), polynuclear quinone compounds (U.S. Pat. Nos. 3,046,127 and 2,951,758), and combinations of triarylimidazole dimers and p-aminophenyl ketones (U.S. Pat. No. 3,549,367). Detailed description), acridine and phenazine compounds (JP 60-105667 A and U.S. Pat. No. 4,239,850 A), oxadiazole compounds (U.S. Pat. No. 4,212,970 A), o-acyloxime compounds (JP 2016-27384 A

[0065] ), and acylphosphine oxide compounds (JP 63-40799 A, JP 5-29234 A, JP 10-95788 A, and JP 10-29997 A). Commercially available photopolymerization initiators can also be used, and examples thereof include IRGACURE-184, IRGACURE-907, IRGACURE-369, IRGACURE-651, IRGACURE-819, IRGACURE-OXE-01, and IRGACURE-OXE-02 manufactured by BASF.

[0219] The maximum absorption wavelength of the photopolymerization initiator is preferably 300 to 400 nm.

[0220] When the present composition contains a polymerization initiator, the content of the polymerization initiator is preferably 0.1 to 10% by mass, more preferably 0.5 to 5.0% by mass, based on the total mass of the present composition.

[0221] [Other Components] The composition may contain components other than the above-described components (hereinafter also referred to as "other components"). Examples of the other components include a vertical alignment agent and an adhesion agent.

[0222] [Electrodes] The electrodes of the present EO element are not particularly limited, and conventionally known electrodes described in JP 2021-043263 A, JP 2021-043263 A, etc. can be used. Here, when the present EO element is an optical modulation device having a slot waveguide, the electrodes are not only so-called positive and negative electrodes, but also the rails and slabs described in JP 2021-167851 A, etc. This concept includes these electrodes.

[0223] A suitable embodiment of the electrode is a transparent electrode film. When a transparent electrode film is used in the EO element, light is not blocked during exposure in a post-process, and can easily reach the EO layer, resulting in excellent curing characteristics. Examples of materials that can be used to form the transparent electrode film include indium tin oxide (ITO), gallium-doped zinc oxide (GZO), and aluminum-doped zinc oxide (GZO).

[0224] [Alignment Layer] The EO element may have an alignment layer. The alignment layer is preferably disposed in contact with the EO layer. For example, when the EO element is an optical modulation device having a ridge waveguide, an alignment layer may be disposed between the two electrodes disposed on the substrate and the EO material (EO layer) in the ridge waveguide. Furthermore, when the EO element is an optical modulation device having a slot waveguide, an alignment layer may be disposed in the slot portion. The alignment layer may be any layer that can achieve the desired alignment state for the liquid crystal compound contained in the EO layer. However, from the viewpoint of ease of control of the pretilt angle of the alignment layer, an alignment layer formed by rubbing treatment (rubbed alignment layer) is preferred, and from the viewpoint of uniformity of alignment, a photo-alignment layer formed by light irradiation is preferred.

[0225] The thickness of the alignment layer is preferably 0.001 to 1 μm, more preferably 0.1 to 1.0 μm. Here, the thickness of the alignment layer is calculated as the average value of measurements at any five points using a surface roughness meter (for example, P-10 (manufactured by TENCOR Corporation)).

[0226] The variation in thickness of the alignment layer is preferably greater than -5.0% and smaller than 5.0%, more preferably greater than -3.0% and smaller than 3.0%, and even more preferably greater than -2.0% and smaller than 2.0%, in order to facilitate uniform alignment of the liquid crystal compound. Here, the variation in thickness of the alignment layer is measured according to the method described in the Examples section below.

[0227] [Method for Manufacturing Electro-Optical Element] The method for manufacturing the present EO element is not particularly limited, but preferably includes the following steps. That is, one embodiment of the method for manufacturing the present EO element includes: a step of applying the present composition described above to form a coating film (hereinafter also referred to as the "coating film forming step"); a step of orienting the liquid crystal compound and the organic dye contained in the coating film to obtain an EO layer (hereinafter also referred to as the "alignment step"); a first curing step of curing the EO layer; and a second curing step of further curing the EO layer after the first curing step. An example embodiment is one in which the EO layer is subjected to a poling treatment after the first curing step and before the second curing step, or the curing treatment in the second curing step is performed together with the poling treatment. The present EO element is obtained through these steps. Each step is described in detail below.

[0228] [Coating film forming process] The coating film forming process is a process of forming a coating film by applying the above-mentioned present composition. The present composition can be easily applied by using the present composition containing the above-mentioned solvent or by using the present composition in a liquid form such as a molten liquid by heating or the like. Specific examples of the method for applying the present composition include known methods such as roll coating, gravure printing, spin coating, wire bar coating, extrusion coating, direct gravure coating, reverse gravure coating, die coating, spraying, and inkjet.

[0229] [Orientation Step] The orientation step is a step of orienting the organic dye and liquid crystal compound contained in the coating film. This results in an EO layer. The orientation step may include a drying treatment. Components such as the solvent can be removed from the coating film by the drying treatment. The drying treatment may be performed by leaving the coating film at room temperature for a predetermined time (e.g., natural drying), or by heating and / or blowing air. Here, the organic dye and liquid crystal compound contained in the present composition may be oriented by the above-mentioned coating film formation step or drying treatment. For example, in an embodiment in which the present composition is prepared as a coating liquid containing a solvent, the coating film is dried to remove the solvent from the coating film, thereby obtaining an EO layer.

[0230] The orientation step preferably includes a heat treatment. This allows the organic dye and liquid crystal compound contained in the coating film to be oriented, and the coating film after the heat treatment can be suitably used as an EO layer. From the viewpoint of manufacturability, the heat treatment is preferably performed at a temperature of 10 to 250°C, more preferably 25 to 190°C. The heating time is preferably 1 to 300 seconds, more preferably 1 to 60 seconds.

[0231] The orientation step may include a cooling treatment carried out after the heating treatment. The cooling treatment is a treatment in which the coated film after heating is cooled to about room temperature (20 to 25°C). This makes it possible to fix the orientation of the specific organic dye and liquid crystal compound contained in the coated film. The cooling method is not particularly limited and can be carried out by a known method.

[0232] [First curing step] The first curing step is carried out by heating and / or light irradiation (exposure) when the component contained in the EO layer (or the present composition) has a crosslinkable group (polymerizable group), for example. Among these, the first curing step is preferably carried out by light irradiation.

[0233] The conditions for the curing treatment in the first curing step are not particularly limited. When the curing treatment is carried out by light irradiation, it is preferable to carry out irradiation with light having a wavelength of 300 to 450 nm (high-pressure mercury lamp), for example.

[0234] When a component contained in the EO layer (or the present composition) has a crosslinkable group (polymerizable group), in the first curing step, it is preferable to perform heating and / or light irradiation (exposure) so that the reaction rate of all crosslinkable groups (polymerizable groups) is 5 to 20%. Here, the "reaction rate of crosslinkable groups (polymerizable groups)" refers to the proportion of all crosslinkable groups (polymerizable groups) in each component having a crosslinkable group (polymerizable group) contained in the EO layer (or the present composition) that are consumed by crosslinking (polymerization) in the curing treatment. For example, when the polymerizable group is a (meth)acryloyl group, this can be calculated by infrared spectroscopy (IR) measurement.

[0235] [Second curing step] The second curing step is a step of further curing the EO layer after the first curing step. This further improves the reaction rate, thereby improving stability over time. For example, when the component contained in the EO layer (or the present composition) has a crosslinkable group (polymerizable group), the second curing step is carried out by heating and / or light irradiation (exposure). Among these, the second curing step is preferably carried out by light irradiation.

[0236] The conditions for the curing treatment in the second curing step are not particularly limited. When the curing treatment is carried out by light irradiation, it is preferable to carry out irradiation with light having a wavelength of 300 to 450 nm from an ultra-high pressure mercury lamp, as in the curing treatment in the first curing step.

[0237] When a component contained in the EO layer (or the present composition) has a crosslinkable group (polymerizable group), in the second curing step, it is preferable to perform heating and / or light irradiation (exposure) so that the reaction rate of all crosslinkable groups (polymerizable groups) contained before the first curing step reaches 80 to 100%. Here, the "reaction rate of crosslinkable groups (polymerizable groups)" is as described above.

[0238] The method for producing an EO element may further include a curing step of subjecting the EO layer after the second curing step to a further curing treatment so that the reaction rate is 80 to 100%. The curing step after the second curing step can be carried out in the same manner as the second curing step.

[0239] In the manufacturing method of the present EO element, it is preferable to perform a poling treatment on the EO layer after the first curing step and before the second curing step, or to perform the curing treatment in the second curing step together with the poling treatment. In this way, the EO layer used in the present EO element can be formed. Here, the poling treatment is not particularly limited, and known poling treatments such as optical poling and electric field poling can be used. Among these, the electric field poling method is particularly preferable in terms of the simplicity of the apparatus and the high degree of orientation obtained. The electric field poling method can be broadly divided into a contact poling method in which a nonlinear optical material is sandwiched between a pair of electrodes and an electric field is applied, and a corona poling method in which corona discharge is performed on the surface of the nonlinear optical material on the substrate electrode and a charging electric field is applied.

[0240] [Method for manufacturing an electro-optical element using a transfer film] The method for manufacturing the present EO element is preferably carried out using a transfer film. One embodiment of the method for manufacturing the present EO element using a transfer film includes a step of laminating the EO layer of a transfer film having a temporary support, an alignment layer, and an EO layer in this order to a substrate, and then peeling off the temporary support. The present EO element is obtained through these steps.

[0241] The EO layer and alignment layer of the transfer film may be the same as those described in the EO element described above. The substrate may be the same as those described in the EO element described above. Electrodes may be disposed on the surface of the substrate. The electrodes may be the same as those described in the EO element described above.

[0242] The temporary support of the transfer film is a member that supports the alignment layer or EO layer and is removed, for example, after the production of the EO element. The temporary support may have either a single-layer structure or a multilayer structure. The temporary support is preferably a film, more preferably a polymer film. Furthermore, the temporary support is preferably a flexible polymer film that does not undergo significant deformation, shrinkage, or elongation under pressure or under pressure and heat, and is also preferably a polymer film that is free from deformation such as wrinkles and scratches. Examples of such polymer films include polymer films containing at least one selected from the group consisting of polypropylene (PP), polyethylene (PE), polyethylene terephthalate (PET), polyethylene naphthalate (PEN), and triacetyl cellulose (TAC), with polyethylene terephthalate film being preferred. The thickness of the temporary support is not particularly limited, but from the standpoint of ease of handling and versatility, it is preferably 5 to 200 μm, more preferably 5 to 150 μm, and even more preferably 5 to 100 μm. Here, the thickness of the temporary support is calculated as the average value when 100 points are measured at 1 cm intervals over an area of ​​10 cm × 10 cm using a pencil-type high-precision digital length measuring instrument PHA-13W manufactured by Tosei Engineering Co., Ltd., with an E-ST-100DB stand attached, and a MINICOM-M (Model E-M) as a display device.

[0243] When the EO layer of the present EO element is used as a core layer, the present EO element having an optical waveguide can be produced, for example, by laminating the EO layer of the above-mentioned transfer film to the lower clad layer, peeling off the temporary support, and then providing an upper clad layer.

[0244] The present invention will be described in more detail below with reference to examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the examples shown below.

[0245] Example 1 Formation of a Photo-Alignment Film The following alignment layer composition was applied by spin coating onto a glass substrate on which ITO had been sputtered, and dried at 100°C for 1 minute. After that, unpolarized ultraviolet light (10 mJ / cm) was applied from directly above the coating layer. ２ An alignment layer 1 (photo-alignment film) having a thickness of 0.5 μm was formed by irradiating the film with light from an ultra-high pressure mercury lamp.

[0246] ------------------------------------------------------------------ Composition for forming alignment layer -------------------------------------------------- Polymer PA1 (described below) 100.00 parts by mass Acid generator PAG-1 (described below) 8.00 parts by mass Acid generator CPI-110TF (described below) 0.005 parts by mass Xylene 1220.00 parts by mass Methyl isobutyl ketone 122.00 parts by mass

[0247]

[0248] The weight average molecular weight of the polymer PA1 is 19,000.

[0249] <Formation of EO Layer 1> The following EO layer-forming composition 1 was applied by spin coating onto the alignment layer 1 and aged at 130°C for 30 seconds to form an EO layer 1 (thickness 1.8 µm) in which the liquid crystal compound L2 and the organic dye E1 were vertically aligned. In this way, a laminate 1 was obtained in which the glass substrate, alignment layer, and EO layer 1 were arranged in this order. The laminate 1 can be used as an EO element.

[0250] ----------------------------------------------- EO layer forming composition 1 -------------------------------------------------- ・0.0917 parts by mass of liquid crystal compound L2 described below ・0.0100 parts by mass of organic dye E1 described below ・0.0010 parts by mass of alignment agent S1 described below ・0.8953 parts by mass of chloroform ・0.0020 parts by mass of ADEKA Arcles NCI-730 (manufactured by ADEKA Corporation, photopolymerization initiator) --------------------------------

[0251]

[0252] Liquid crystal compound L2 has a mass ratio of the constituent units, from top to bottom, of 80.0:3.0:17.0, and a weight average molecular weight of 8,000.

[0253]

[0254]

[0255] The alignment agent S1 has a mass ratio of the constituent units, from left to right, of 32.0:13.0:15.0:40.0, and a weight average molecular weight of 16,000.

[0256] The obtained laminate 1 was placed on a hot plate and treated by corona poling. Specifically, laminate 1 was held at 130°C for 10 minutes with a charging voltage of 6 kV applied at a distance of 10 mm from EO layer 1, and then air-cooled from that state to 23°C over 10 minutes while the charging voltage was still applied. After that, an exposure treatment (dye fixation) was performed in which light with a wavelength of 365 nm was irradiated onto the surface of EO layer 1 using a PLA-501F (exposure machine, ultra-high pressure mercury lamp, manufactured by Canon Inc.).

[0257] [Examples 2 to 4, Comparative Examples 1 to 3] Laminates of each of the Examples and Comparative Examples were obtained in the same manner as in Example 1, except that compositions were used in which the types of liquid crystal compound and organic dye contained in the EO layer-forming composition were changed as shown in Table 1. The structure of each component listed in Table 1 is shown below.

[0258] <Liquid crystal compound>

[0259]

[0260] The liquid crystal compound L1 has a mass ratio of the constituent units, from top to bottom, of 30.0:54.0:3.0:13.0, and a weight average molecular weight of 12,409.

[0261]

[0262] <Organic dye>

[0263]

[0264]

[0265] p-nitroaniline (paranitroaniline)

[0266] [Aspect Ratio, θes, and δp Value of Liquid Crystal Compound] The aspect ratio, θes, and δp value of each liquid crystal compound were measured by the method described above. The results are shown in Table 1 below.

[0267] [λmax, second-order molecular susceptibility, aspect ratio, and θeg of organic dyes] The λmax, second-order molecular susceptibility, aspect ratio, and θeg of each organic dye were measured by the methods described above. The results are shown in Table 1 below.

[0268] [Temperature range showing liquid crystallinity] The liquid crystal compound was heated on a hot stage and observed under a polarizing microscope to examine the liquid crystal phase transition behavior. The range showing liquid crystallinity refers to the temperature range in the nematic state. The results are shown in Table 1 below.

[0269] [Softening Point of EO Layer] The sample (EO layer) was melted at 200°C, cooled to 50°C, and then heated to 200°C to measure the temperature change in viscosity. The temperature decrease rate and temperature increase rate were both set at 5°C / min. Here, the viscosity was measured using Anton Paar rheometers MCR702 and DPP-25 under the measurement conditions of a gap of 0.6 mm, a shear strain of 0.1%, and an angular frequency of 10 rad / s. Based on the temperature change in the viscosity of the EO layer measured in this way, a graph was obtained in which the horizontal axis was plotted as temperature and the vertical axis was plotted as viscosity. Based on the obtained graph, the change in viscosity with respect to a small change in temperature was differentiated, and the point at which the viscosity suddenly decreased was determined as the softening point. The results are shown in Table 1 below.

[0270] [Viscosity of EO layer near softening point] When the viscosity of the EO layer is 10×10 ７ ~10 x 10 ８ It was determined whether the temperature range in which the viscosity of the EO layer was 10×10 mPa s was within a temperature range of ±30°C of the softening point of the EO layer. For the determination, the graph obtained in the above "Softening point of the EO layer" was used. ７ ~10 x 10 ８ The temperature range in which the viscosity reached mPa s was determined to be within ±30°C of the softening point of the EO layer, and the temperature range in which the viscosity reached mPa s was determined to be "○", and the temperature range in which the viscosity reached mPa s was not within ±30°C of the softening point of the EO layer was determined to be "×". The results are shown in Table 1 below.

[0271] [Orientation Degree of Organic Dye] The orientation degree of the organic dye in the EO layer was calculated by the following procedure. With a linear polarizer inserted on the light source side of an optical microscope (for example, an "ECLIPSE E600 POL" product manufactured by Nikon Corporation), the laminate of the example or comparative example was set on a sample stage, and the absorbance of the EO layer in the wavelength range of 380 nm to 780 nm was measured at 1 nm intervals using a multichannel spectrometer (manufactured by Ocean Optics, product name "QE65000"), and the orientation degree in the wavelength range of 400 nm to 700 nm was calculated using the following formula: Orientation Degree: S = ((Az0 / Ay0) - 1) / ((Az0 / Ay0) + 2) In the above formula, "Az0" represents the absorbance for polarized light in the absorption axis direction of the EO layer, and "Ay0" represents the absorbance for polarized light in the transmission axis direction of the EO layer.

[0272] [Orientation Degree of Components Derived from Liquid Crystal Compounds] The orientation degree of components derived from liquid crystal compounds in the EO layer refers to the degree of vertical orientation calculated by the following procedure. First, polarized ATR (Attenuated Total Reflectance)-IR (Infrared Spectroscopy) measurement (ATR crystal: Ge, incident angle: 45 degrees) was performed using a Fourier transform infrared spectrophotometer (VERTEX70 manufactured by Bruker) for the incident polarization (P / S) of the EO layer in the laminate of the Examples or Comparative Examples, and the three-dimensional absorption coefficient was determined. Note that the analysis was performed using the skeletal vibration mode of the aromatic ring, 1606 cm －１ Next, the degree of orientation in the z-axis direction, P, was calculated from the determined three-dimensional absorption coefficient using the following formula as the degree of orientation of the component derived from the liquid crystal compound in the EO layer. ２ｚ was calculated. ｘ , k ｙ , k ｚ and P respectively represent the refractive index in the x-axis direction, the y-axis direction, and the z-axis direction of the component derived from the liquid crystal compound. Note that since the component derived from the liquid crystal compound is isotropic, it is assumed that the refractive index is 1.5 and that it is uniaxially oriented in the z-axis direction. ２Ｚ = (k ｚ / k ｘ −1) / (k ｚ / k ｘ +2) k ｘ = k ｙ = 1.5

[0273] [Thickness of Alignment Layer and Thickness Variation of Alignment Film] The thickness of the alignment layer was calculated as the average value of measurements taken at any five points using a surface roughness meter (for example, P-10 (manufactured by TENCOR Corporation)). The results are shown in Table 1 below. The thickness variation of the alignment layer was evaluated using the following method and criteria. The results are shown in Table 1 below. <Measurement Method> The thickness was measured using a surface roughness meter P-10 (manufactured by TENCOR Corporation). <Criteria> The heights of 100 film surfaces at 1 cm intervals on the obtained alignment layer (11 cm x 11 cm) were measured using a three-dimensional surface structure analysis microscope (manufacturer: ZYGO Corporation, model: New View 5022), and the percentage variation of the maximum or minimum value relative to the average value was evaluated. C or higher is a practical level. A: The variation in thickness of the alignment film is less than ±2.0%, which is extremely good. B: The variation in the thickness of the alignment film is between ±2.0% and ±3.0%, which is good. C: The variation in the thickness of the alignment film is between ±3.0% and ±5.0%, which is fair. D: The variation in the thickness of the alignment film is between ±5.0% and ±5.0%, which is poor.

[0274] [Electro-optic constant (r0)] The electro-optic constant (hereinafter also referred to as "r value") was calculated by measuring the applied voltage dependency of the refractive index change at a wavelength of 1309 nm using a prism coupler device (Model 2010 / M manufactured by Metricon) and a coated prism (P-200C, a prism with a nickel-coated prism surface) for the laminate that had been subjected to the corona poling treatment. The obtained r value was designated as r0. Based on the r0 value, the value of the electro-optic constant was evaluated according to the following criteria. The results are shown in Table 1 below. The r value was calculated using the following formula (R). In the following formula (R), δn / δV is the slope of the applied voltage dependency of the refractive index change, d is the thickness (pm) of the laminate, and n ＴＭ represents the refractive index of the laminate with no voltage applied (laminate after corona poling treatment) when a TM wave is incident. r = {(δn / δV) × 2 × d} / (n ＴＭ ３ ) Formula (R)

[0275] (Evaluation criteria) S: 100 pm / V or more A: 80 pm / V or more, less than 100 pm / V B: 45 pm / V or more, less than 80 pm / V C: 25 pm / V or more, less than 45 pm / V D: 10 pm / V or more, less than 25 pm / V E: Less than 10 pm / V

[0276] [Change in Electro-Optic Constants Over Time (r1 / r0)] The following evaluation was carried out to examine the change in electro-optical constants over time. The laminate that had been subjected to the corona poling treatment was left at 85°C and 85% RH for 3 days, and the r value was calculated in the same manner as for r0, except that this was used. The resulting r value was designated as r1. The change in the electro-optical constants over time was evaluated based on the ratio of r1 to r0 (r1 / r0) according to the following criteria. The results are shown in Table 1 below.

[0277] <Evaluation criteria> A: 0.8 or more B: 0.5 or more and less than 0.8 C: Less than 0.5

[0278]

[0279] As shown in Table 1, when an EO layer containing an organic dye having a maximum absorption wavelength of 600 to 1200 nm is used and the degree of orientation of the component derived from the liquid crystal compound is 0.50 or more, an electro-optical element having an electro-optical layer with excellent stability over time of the electro-optical constants can be obtained (Examples 1 to 4). In contrast, when an EO layer is used that does not contain an organic dye having a maximum absorption wavelength of 600 to 1200 nm or in which the degree of orientation of the component derived from the liquid crystal compound is less than 0.50, the stability over time of the electro-optical constants of the EO layer is poor (Comparative Examples 1 to 3). It was confirmed that none of the liquid crystal compounds used in the examples exhibited ferroelectricity.

Claims

1. An electro-optical element having a substrate, an electro-optical layer, and electrodes, wherein the electro-optical layer is a layer formed by fixing the orientation state of an electro-optical layer-forming composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye whose maximum absorption wavelength is 600 to 1200 nm, and wherein the degree of orientation of the component derived from the liquid crystal compound in the electro-optical layer is 0.50 or more.

2. The electro-optical element according to claim 1, wherein the liquid crystal compound comprises at least one of a polymer liquid crystal compound having a repeating unit containing a mesogen group and a low molecular weight liquid crystal compound, and the aspect ratio of at least one of the repeating unit containing a mesogen group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound is 2.0 or greater.

3. The electro-optical element according to claim 1, wherein the liquid crystal compound comprises at least one of a polymer liquid crystal compound having a repeating unit containing a mesogen group and a low molecular weight liquid crystal compound, and the angle θes formed between the vector of the molecular long axis and the vector of the transition dipole moment in at least one of the repeating unit containing the mesogen group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound is 30.0° or less.

4. The electro-optical element according to claim 1, wherein the angle θeg formed between the vector of the molecular long axis and the vector of the transition dipole moment in said organic dye is 10.0° or less.

5. The electro-optical element according to claim 1, wherein the liquid crystal compound comprises at least one of a polymer liquid crystal compound having a repeating unit containing a mesogen group and a low molecular weight liquid crystal compound, and the polar term of the Hansen solubility parameter of at least one of the repeating unit containing a mesogen group of the polymer liquid crystal compound and the low molecular weight liquid crystal compound is 7.0 or more.

6. The electro-optical element according to claim 1, wherein the liquid crystal compound exhibits liquid crystallinity in a temperature range of 25 to 250°C, and the softening point of the electro-optical layer is 100°C or higher.

7. When the softening point of the electro-optical layer is X°C, the melt viscosity of the electro-optical layer is 10×10 in a specific temperature range from X-30°C to X+30°C. ７ ~10 x 10 ８ The electro-optical element according to claim 1 , wherein there is a temperature range in which the viscosity is mPa·s.

8. The electro-optical element according to claim 1, wherein the liquid crystal compound exhibits nematic liquid crystallinity or smectic liquid crystallinity.

9. The electro-optical element according to claim 1, wherein the electro-optical element has an alignment layer, the alignment layer being disposed in contact with the electro-optical layer.

10. The electro-optical element according to claim 9, wherein the thickness of the alignment layer is 0.001 to 1 μm.

11. The electro-optic element according to claim 9, wherein the variation in thickness of the alignment layer is greater than −5.0% and less than 5.0%.

12. The electro-optical element according to claim 1, wherein the composition for forming the electro-optical layer contains an alignment agent.

13. The electro-optical element according to claim 1, wherein the organic dye has a maximum absorption wavelength of 700 to 1200 nm.

14. The electro-optical element according to claim 1, wherein the electrodes are transparent electrode films.

15. The electro-optical element according to claim 1, wherein the electro-optical element is an optical modulation device having an optical waveguide.

16. The electro-optical element according to claim 15, wherein the optical waveguide has a core layer and a clad layer, and the electro-optical layer is used as the core layer.

17. The electro-optical element according to claim 15, wherein the optical waveguide is a slot waveguide or a ridge waveguide.

18. A method for producing an electro-optical element according to any one of claims 1 to 17, comprising a step of laminating the electro-optical layer of a transfer film having a temporary support, an alignment layer, and an electro-optical layer in this order to a substrate, and then peeling off the temporary support, wherein the electro-optical layer is a layer formed by fixing the alignment state of a composition for forming an electro-optical layer, the composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm, and wherein the degree of orientation of the component derived from the liquid crystal compound in the electro-optical layer is 0.50 or more.

19. A method for producing an electro-optical element according to any one of claims 1 to 17, comprising: a step of forming a coating film by applying a composition for forming an electro-optical layer, the composition containing a liquid crystal compound that does not exhibit ferroelectricity and an organic dye having a maximum absorption wavelength of 600 to 1200 nm; a step of orienting the liquid crystal compound and the organic dye contained in the coating film to obtain an electro-optical layer; a first curing step of curing the electro-optical layer; and a second curing step of further curing the electro-optical layer after the first curing step, wherein a poling treatment is performed on the electro-optical layer after the first curing step and before the second curing step, or the curing treatment in the second curing step is performed together with the poling treatment.

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