Composition for forming electro-optical layer, electro-optical layer, and laminate

Abstract

The present invention addresses the problem of providing: a composition for forming an electro-optical layer, said composition exhibiting a high electro-optical constant and being capable of forming an electro-optical layer that reduces transmission losses; an electro-chemical layer; and a laminate. This composition for forming an electro-optical layer contains a liquid crystal compound, an organic dye having a secondary molecular sensitivity of 400,000 × 10-33 esu or more, and a surfactant.

Description

Composition for forming electro-optical layer, electro-optical layer and laminate

[0001] The present invention relates to a composition for forming an electro-optical layer, an electro-optical layer, and a laminate.

[0002] In recent years, organic electro-optic (EO) materials have been attracting attention as materials that can be used in optical control elements (optical elements) such as optical modulators, optical switches, and optical interconnects, from the perspective of realizing ultrafast optical communications.

[0003] For example, Patent Document 1 discloses a nonlinear optical element obtained by orienting a nonlinear optical material containing a polymer liquid crystalline compound and a nonlinear optical compound, and describes that the oriented nonlinear optical material is used in an electro-optical layer such as an optical waveguide.

[0004] Japanese Unexamined Patent Publication No. 2-029721

[0005] The present inventors evaluated an electro-optical layer formed using a nonlinear optical material such as that described in Patent Document 1 and found that the electro-optical layer had a low electro-optical constant and a large transmission loss.

[0006] Therefore, an object of the present invention is to provide a composition for forming an electro-optical layer, an electro-optical layer, and a laminate that can form an electro-optical layer that exhibits a high electro-optical constant and has low transmission loss.

[0007] As a result of extensive research aimed at solving the above-mentioned problems, the present inventors have found that an electro-optical layer having a high electro-optical constant and low transmission loss can be formed by using a composition for forming an electro-optical layer containing a liquid crystal compound, an organic dye exhibiting a predetermined second-order molecular susceptibility, and a surfactant, and have thus completed the present invention. That is, the present inventors have found that the above-mentioned problems can be solved by the following configuration.

[0008] [1] Liquid crystal compound with a second-order molecular susceptibility of 400,000 x 10 －３３esu or more, and a surfactant. [2] The composition for forming an electro-optical layer according to [1], wherein the organic dye has a molecular aspect ratio of 2.0 or more. [3] The composition for forming an electro-optical layer according to [1] or [2], wherein the organic dye has an angle θeg formed by the vector of the molecular long axis and the vector of the transition dipole moment of 10.0° or less. [4] The composition for forming an electro-optical layer according to any one of [1] to [3], wherein the organic dye is a compound represented by formula (E1) described below. In the formula (E1) described below, R represents a hydrogen atom, or an alkyl group, an aryl group, or a heterocyclic group, each of which may have a substituent; ２ - may be substituted with a divalent substituent, and when n is 2 or more, two or more R may be the same or different and may be bonded to each other to form a ring containing E1, E1 represents an oxygen atom, a sulfur atom, or a nitrogen atom, and A1 is -C(R Ａ１ ) = C(R Ａ２ )-, or an arylene group or a heterocyclic group which may have a substituent, 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, and A1 is -C(R Ａ１ ) = C(R Ａ２ )-, then R Ａ１ and R may be bonded to form a ring containing E1, A2 represents a single bond, or an arylene group or heterocyclic group which may have a substituent, and when m is 2 or more, two or more A2 may be the same or different, 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-, when n1 or m is 2 or more, two or more L1s may be the same or different, when n2 is 2 or more, two or more L2s may be the same or different, when n1 is 2 or more, adjacent L1s may be bonded to each other to form a ring, when n2 is 2 or more, adjacent L2s may be bonded to each other to form a ring, when L1 and L2 are adjacent, adjacent L1 and L2 may be bonded to each other to form a ring, R 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, and multiple R Ｌ５ each independently represents a hydrogen atom, an alkyl group, or a phenyl group; ２ is -C(R Ｅ２１ ) (R Ｅ２２ )-, -C(=O)-, -C(=S)-, or -C(=NR Ｅ４ )-, R Ｅ２１ and R Ｅ２２ 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, and —CH 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; R 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, ３ is -O-, -S-, -N(R Ｅ５ )- or -S(=O)-, R Ｅ５represents a hydrogen atom, or an optionally substituted 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; n represents an integer of 1 or 2; n1 represents an integer of 0 to 3; n2 represents an integer of 0 to 3; and m represents an integer of 0 to 4. [5] An electro-optical layer formed using the composition for forming an electro-optical layer according to any one of [1] to [4], wherein the organic dye contained in the electro-optical layer is aligned. [6] The electro-optical layer according to [5], wherein the degree of alignment of the organic dye is greater than 0.3. [7] A laminate comprising an alignment layer and the electro-optical layer according to [5] or [6], disposed on the alignment layer.

[0009] According to the present invention, it is possible to provide a composition for forming an electro-optical layer, an electro-optical layer, and a laminate, which are capable of forming an electro-optical layer that exhibits a high electro-optical constant and has low transmission loss.

[0010] The present invention will be described in detail below. The following description of the constituent elements may be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits.

[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, for each component, a substance corresponding to the component may be used alone or in combination of two or more. Here, when two or more substances for each component are used in combination, 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, "(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".

[0014] Furthermore, unless otherwise specified, the bonding direction of divalent groups represented in this specification is not limited. For example, when Y is -C(O)-O- in a compound represented by the formula "X-Y-Z", Y may be -C(O)-O- or -O-C(O)-. Furthermore, the compound may be "X-C(O)-O-Z" or "X-O-C(O)-Z".

[0015] [Substituent W] The substituent W used in this specification represents the following group. Examples of the substituent W include 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 alkylcarbonyl group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 1 to 10 carbon atoms, an alkylcarbonyloxy group having 1 to 10 carbon atoms, an alkylamino group having 1 to 10 carbon atoms, an alkylaminocarbonyl group, 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 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 aryl Oxycarbonyloxy group, amino group (including 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. The substituent W may be a group represented by the following formula (W1):

[0016]

[0017] In formula (W1), LW represents a single bond or a divalent linking group, SPW represents a divalent spacer group, Q represents a crosslinkable group, and * represents a bonding position.

[0018] The divalent linking group represented by LW includes —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. LW may be a group formed by combining two or more of these groups (hereinafter also abbreviated as "LC").

[0019] The divalent spacer group represented by SPW includes a linear, branched, or cyclic alkylene group having 1 to 50 carbon atoms, or a heterocyclic group having 1 to 20 carbon atoms. The carbon atoms of the alkylene group and heterocyclic group may be —O—, —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)=N-, -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-, -C(S)-, -S(O)-, -SO ２ The hydrogen atoms of the alkylene groups and the heterocyclic groups may be substituted with a halogen atom, a cyano group, -Z Ｈ , —OH, —OZ Ｈ , -COOH, -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’’ , -SH, -SZ Ｈ , -C(S)Z Ｈ , -C(O)SZ Ｈ , -SC(O)Z Ｈ (hereinafter, also abbreviated as "SP-H"). 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 those of LW and SPW described above. In -L-CL, CL represents a crosslinkable group. Specific examples of the crosslinkable group include crosslinkable groups represented by the following formulas (P1) to (P30).

[0020]

[0021] In formulas (P-1) to (P-30), R Ｐ is 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 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 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.

[0022] [Composition for forming electro-optical layer] The composition for forming an electro-optical layer of the present invention (hereinafter also referred to as "the composition") contains a liquid crystal compound and a compound having a second-order molecular susceptibility of 400,000×10 －３３ The composition contains an organic dye (hereinafter also referred to as "specific organic dye") of 0.1 sq. m or more and a surfactant. This composition allows the formation of an electro-optical layer (hereinafter also referred to as "EO layer") that exhibits a high electro-optical constant and low transmission loss. While the details of this are unclear, it is generally assumed as follows: The specific organic dye contained in this composition has a high second-order molecular susceptibility, which is presumed to increase the electro-optical constant of the EO layer formed using this composition. Furthermore, the surfactant contained in this composition acts to reduce surface irregularities of the EO layer formed using this composition, suppressing light scattering and thereby reducing transmission loss in the EO layer.

[0023] [Liquid Crystal Compound] The composition contains a liquid crystal compound. As the liquid crystal compound, either a polymer liquid crystal compound or a low molecular weight liquid crystal compound can be used, with a polymer liquid crystal compound being preferred due to its ability to increase the degree of alignment. Furthermore, as the liquid crystal compound, a polymer liquid crystal compound and a low molecular weight liquid crystal compound may be used in combination. Here, "polymer liquid crystal compound" refers to a liquid crystal compound having a repeating unit in its chemical structure. Furthermore, "low molecular weight liquid crystal compound" refers to a liquid crystal compound without a repeating unit in its chemical structure. 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 low molecular weight liquid crystal compounds include the liquid crystal compounds described in paragraphs

[0072] to

[0088] of JP 2013-228706 A, with liquid crystal compounds exhibiting smectic properties being preferred. Examples of such liquid crystal compounds include those described in paragraphs

[0019] to

[0140] of WO 2022 / 014340, the disclosures of which are incorporated herein by reference.

[0024] The polymer liquid crystal compound is preferably a side-chain polymer liquid crystal compound, since it can achieve a higher degree of orientation. A side-chain polymer liquid crystal compound is a liquid crystal compound having a repeating unit. Suitable examples of the side-chain polymer liquid crystal compound include liquid crystal compounds having a repeating unit represented by the following formula (1), which is described in paragraph

[0014] of WO 2018 / 199096:

[0025] In the above formula (1), R １ represents a hydrogen atom or a methyl group, L １ and L ２ each independently represents a single bond or a divalent linking group; M １ represents a mesogen group represented by formula (1-1) described below, T １ represents a terminal group.

[0026] Furthermore, suitable examples of the low molecular weight liquid crystal compound include the compound represented by the following formula (2) described in paragraph

[0074] of JP-A No. 2013-228706: １ -V １ -W １ -X １ -Y １ -X ２ -Y ２ -X ３ -W ２ -V ２ -U ２ (2) In formula (2), X １ , X ２ and X ３ each independently represents an optionally substituted 1,4-phenylene group or an optionally substituted cyclohexane-1,4-diyl group, provided that X １ , X ２ and X ３ At least one of the groups is a 1,4-phenylene group which may have a substituent. The -CH2- constituting the cyclohexane-1,4-diyl group which may have a substituent may be replaced by -O-, -S- or NR-. R is an alkyl group having 1 to 6 carbon atoms or a phenyl group. Y １ and Y ２ are each independently —CH ２ CH ２-, -CH ２ O-, -COO-, -OCOO-, single bond, -N=N-, -CR ａ =CR ｂ -, -C≡C- or CR ａ =N-. ａ and R ｂ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. １ represents a hydrogen atom or a polymerizable group. ２ represents a polymerizable group. １ and W ２ each independently represents a single bond, —O—, —S—, —COO— or OCOO—. １ and V ２ each independently represents an alkanediyl group having 1 to 20 carbon atoms which may have a substituent, and —CH ２ - may be replaced by -O-, -S- or -NH-.

[0027] From the viewpoint of increasing the degree of alignment, the liquid crystal compound preferably has at least one group selected from the group consisting of a fluorine atom, a cyano group, a trifluoromethyl group, and a nitro group.

[0028] The content of the liquid crystal compound is preferably 40 to 95 parts by mass, more preferably 50 to 90 parts by mass, per 100 parts by mass of the specific organic dye.

[0029] The weight-average molecular weight (Mw) of the polymer liquid crystal compound is preferably 1,000 to 500,000, more preferably 2,000 to 300,000, from the viewpoint of achieving superior effects of the present invention. When the Mw of the polymer liquid crystal compound is within the above range, the polymer liquid crystal compound is easy to handle. In particular, from the viewpoint of suppressing cracking during application, the weight-average molecular weight (Mw) of the polymer liquid crystal compound is preferably 10,000 or more, more preferably 10,000 to 300,000. Furthermore, from the viewpoint of the temperature latitude of the degree of orientation, the weight-average molecular weight (Mw) of the polymer liquid crystal compound is preferably less than 100,000, more preferably 2,000 or more but less than 100,000. Here, the weight-average molecular weight of the polymer liquid crystal compound is a value measured by gel permeation chromatography (GPC). Solvent (eluent): N-methylpyrrolidone Apparatus name: TOSOH HLC-8220GPC Column: Three TOSOH TSKgel Super AWM-H (6 mm x 15 cm) 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.

[0030] [Specific organic dye] The composition contains a specific organic dye. The second-order molecular susceptibility of the specific organic dye is 400,000×10 －３３ esu or more, and the electro-optical constant is superior, so 1,000,000×10 －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 specific 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 specific organic dye refers to a value calculated by the density functional method using the quantum scientific 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

[0031] The specific organic dye is preferably a compound represented by the following formula (E1), in terms of further improving the degree of orientation.

[0032]

[0033] 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 the substituent that the alkyl group, aryl group, and heterocyclic group in R may have include the above-mentioned SP-H, among which -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’’ is as defined above. When n is 2 or more, 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.

[0034] 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.

[0035] 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 the above-mentioned SP-H, and among them, -Z Ｈ , —OH, —OZ Ｈ , -NZ Ｈ Z Ｈ’ , -SH, -SZ Ｈ , is preferred. Ｈ and Z Ｈ’ The definition is as above.

[0036] -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 the above-mentioned L-C, among which -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)-, and -(O)S(O)O- are preferred. The definitions of Z and Z' are as described above.

[0037] 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).

[0038]

[0039] 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.

[0040] 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.

[0041]

[0042] 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 the above-mentioned SP-C, among which, -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-, and -SC(O)- are preferred. Specific examples of the monovalent substituent include the above-mentioned SP-H, and among these, halogen atoms (particularly fluorine atoms and chlorine atoms), cyano groups, -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 the above SP-C, among which -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.

[0043] 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 the above-mentioned SP-H, and among these, -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.

[0044] 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.

[0045] In the above formula (E1), n1 represents an integer of 0 to 3, and preferably an integer of 0 to 2.

[0046] In the above formula (E1), n2 represents an integer of 0 to 3, and an integer of 0 to 3 is preferred.

[0047] In the above formula (E1), m represents an integer of 0 to 4, and preferably an integer of 1 to 3.

[0048] The above formula (E1) is preferably a compound represented by the following formula (E1-1) or a compound represented by the following formula (E1-2), and more preferably a compound represented by the following formula (E1-1), in terms of better effects of the present invention.

[0049]

[0050] The definitions of the groups in formula (E1-1) and formula (E1-2) are the same as those in formula (E1) above.

[0051] Specific examples of the specific organic dye are shown below, but the specific organic dye is not limited to these.

[0052]

[0053]

[0054] The aspect ratio of the molecules of the specific organic dye is preferably 1.6 or more, more preferably 2.0 or more, even more preferably 2.2 or more, and particularly preferably 2.3 or more, from the viewpoint of further improving the degree of orientation of the specific organic dye. The aspect ratio of the molecules of the specific organic dye 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 degree of orientation. The aspect ratio of the molecules of the specific organic dye refers to the ratio (L / D) of the length (L) to the diameter (D) of the smallest diameter cylinder inscribed in the molecule of the specific organic dye, and the larger the aspect ratio, the more elongated the molecular shape. The aspect ratio of the molecules of the specific organic dye is calculated using the simulation software Winmostar V11.4.3 (manufactured by CrossAbility) after determining the most stable three-dimensional structure of the specific organic dye under the following conditions using Winmostar V11.4.3 (manufactured by CrossAbility). Hamiltonian: AM1 Method: EF MM: MMOK GNORM: 0.05

[0055] The length (L) of the cylinder is preferably 15.0 to 50.0 Å, more preferably 18.0 to 41.0 Å, and even more preferably 21.0 to 38.0 Å, from the viewpoint of further improving the degree of orientation of the specific organic dye. The diameter (D) is preferably 5.0 to 16.5 Å, more preferably 5.5 to 14.5 Å, and even more preferably 6.5 to 13.5 Å, from the viewpoint of further improving the degree of orientation of the specific organic dye.

[0056] As a method for increasing the molecular aspect ratio of the specific organic dye, 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.

[0057] The angle θeg between the vector of the molecular long axis of the specific organic dye and the vector of the transition dipole moment 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 specific organic dye. The lower limit of θeg is 0°. θeg is calculated as the angle between the vector of the molecular long axis in the most stable conformation and the vector of the transition dipole moment using the simulation software Winmostar V11.4.3 (manufactured by CrossAbility) after determining the most stable conformation of the specific organic dye under the same conditions as in the calculation of the aspect ratio described above. When multiple transition dipole moments are present, the vector of the transition dipole moment with the largest absorption wavelength is used to calculate θeg. If the calculated angle exceeds 90°, the calculated angle is subtracted from 180° to adjust the angle so that it is in the range of 0° or more and less than 90°, and this value is taken as θeg. A specific example of a method for adjusting θeg to the above range is to Ｌ１ ~R Ｌ４ , R Ｅ２１ , R Ｅ２２ , and R Ｅ４As an example, a method of introducing a group that is neither a strong electron donating group nor an electron withdrawing group can be mentioned.

[0058] The content of the specific organic dye is preferably 1 to 80% by mass, more preferably 2 to 70% by mass, and even more preferably 4 to 60% by mass, based on the total mass of the liquid crystal composition. When the content of the specific organic dye is 1% by mass or more, the electro-optical constant is further improved. Furthermore, when the content of the specific organic dye is 80% by mass or less, the degree of orientation of the specific organic dye is further improved.

[0059] [Surfactant] The present composition contains a surfactant. As described above, the inclusion of a surfactant in the present composition can reduce transmission loss. In addition, the surfactant acts to improve the alignment of the liquid crystal compound in the EO layer, thereby increasing the degree of alignment of the specific organic dye aligned with the liquid crystal compound.

[0060] The surfactant may be either a low molecular weight surfactant or a polymeric surfactant. Furthermore, a polymeric surfactant and a low molecular weight surfactant may be used in combination. Here, the term "polymeric surfactant" refers to a surfactant having a repeating unit in its chemical structure. Furthermore, the term "low molecular weight surfactant" refers to a surfactant having no repeating units in its chemical structure.

[0061] 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").

[0062] <First structural unit> (Repeating unit F-1)

[0063]

[0064] 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).

[0065]

[0066] 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.

[0067] In formula (F-1), LF1 represents a single bond or a divalent linking group, and more specific examples thereof include a group represented by -LW-SPW- in formula (W1) 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 it is preferable that the group has -O-, -C(O)-O-, -C(O)-NH-, or -O-C(O)-.

[0068] (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.

[0069]

[0070] In formula (4), Rf ａ is a group represented by the above formula (1), (2) or (3).

[0071] 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:

[0072] - (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)

[0073] 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.

[0074] 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:

[0075] - (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)

[0076] In formula (4), R ２ is a hydrogen atom or a methyl group.

[0077] (b) Repeating unit having a perfluoropolyether group In the above formula (F-1), RF1 also preferably 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 structure, a branched structure, or a cyclic structure, and is preferably a linear structure or a branched structure, and more preferably a linear structure.

[0078] 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).

[0079]

[0080] 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 ２ Rf 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.

[0081] R １２represents 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.

[0082] (d) A group represented by formula (1-d)

[0083]

[0084] 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.

[0085] 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 , -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 ' is preferred, and a hydrogen atom, a fluorine atom, -ZＨ , 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.

[0086] 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, or —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)acrylic 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.

[0087] (Repeating Unit F-2) The repeating unit F-2 is a repeating unit represented by the following formula (F-2).

[0088]

[0089] 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.

[0090] 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.

[0091] 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.

[0092] SP21 and SP22 each independently represent a spacer group, and examples thereof include SPW in the above formula (W1). SP21 and SP22 are preferably a single bond or a linear, branched, or cyclic alkylene group having 1 to 10 carbon atoms. Here, the carbon atom of the alkylene group may be substituted with -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.) In addition, a hydrogen atom of the alkylene group may be substituted with a fluorine atom or a fluoroalkyl group.

[0093] 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)acrylic 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] (Repeating Unit S) The repeating unit S is a repeating unit represented by the following formula (S).

[0098]

[0099] 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.

[0100] 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. ３３may 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.

[0101] In formula (S), R ２１ and R ２２ R each independently represents a hydrogen atom or an alkyl group. ２１ and R ２２ Examples of the alkyl group represented by one embodiment of the formula (1) include a linear alkyl group having 1 to 18 carbon atoms, and a branched or cyclic alkyl group having 3 to 18 carbon atoms. Specific examples include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, a tert-butyl group, and a cyclohexyl group. ２１ and R ２２ is preferably a hydrogen atom.

[0102] 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). ２３is 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.

[0103] 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.

[0104] In formula (S), L Ｓ２ 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 structural formulae K-1-L, K-2-L, and K-3-L are shown below. In the structural 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.

[0105]

[0106] (Repeating Unit A) The repeating unit A is a repeating unit represented by the following formula (A).

[0107]

[0108] In formula (A), R ２１ , R ２２ , and R ２３ are each defined as the same symbol in formula (S).

[0109] 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 formed by a combination of two or more thereof. １ ~R ５ each 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.

[0110] 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.

[0111] In formula (A), L Ａ２ represents a single bond or a na+1-valent linking group. Ａ２Examples 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.

[0112] 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 from 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 formulas (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 formulas), and therefore fall under the category of a specific alkyl group.

[0113]

[0114] 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).

[0115] Examples of the first constitutional unit are shown below, but the first constitutional unit is not limited to the examples below.

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] 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.

[0123] <Second Structural Unit> (Repeating Unit M) The repeating unit M is a repeating unit represented by the following formula (M).

[0124]

[0125] 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.

[0126] 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.

[0127] In formula (M), LX represents a single bond or a divalent linking group, and more specific examples include a group represented by -LW-SPW- in formula (W1) 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.

[0128] 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.

[0129] TX represents a group represented by formula (M1) or a group represented by formula (M2).

[0130]

[0131] In the above formulas (M1) and (M2), * represents a linking site with SPX.

[0132] 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 represents —COOH, —NR Ｍ１ R Ｍ２ is preferred.

[0133] 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 a group represented by -LW-SPW- in the above formula (W1), and when m2 is 2 or more, multiple LM2 may be the same or different, and TM2 represents a terminal group.

[0134] 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. From the viewpoint 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).

[0135]

[0136] In formulas (II-1) to (II-4), D １ is —S—, —O—, or NR １１ represents -, and R１１ 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 １３ each 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.

[0137] 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 ２But, -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.

[0138] 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 ３H), and other known substituents. Details of the substituents are described in paragraph

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

[0139] LM2 represents a single bond or a divalent linking group, more specifically, a group represented by -LW-SPW- in the above formula (W1), among which, 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.

[0140] 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.

[0141] Examples of the second constitutional unit are shown below, but the second constitutional unit is not limited to the examples below.

[0142]

[0143] 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.

[0144] <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.

[0145]

[0146] 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.

[0147] The content of the surfactant (particularly, a 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 specific organic dye. If the content of the surfactant is 0.10 parts by mass or more, the effect of reducing transmission loss is further improved, and the degree of orientation is further improved. If the content of the surfactant is 30.0 parts by mass or less, the electro-optic constant can be further increased.

[0148] 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.

[0149] [Solvent] From the viewpoint of workability, the present composition preferably contains a solvent. Examples of the solvent include ketones (e.g., acetone, 2-butanone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone), ethers (e.g., dioxane, tetrahydrofuran, tetrahydropyran, dioxolane, tetrahydrofurfuryl alcohol, and cyclopentyl methyl ether), aliphatic hydrocarbons (e.g., hexane), alicyclic hydrocarbons (e.g., cyclohexane), aromatic hydrocarbons (e.g., benzene, toluene, xylene, and trimethylbenzene), halogenated carbons (e.g., dichloromethane, trichloromethane (chloroform), dichloroethane, dichlorobenzene, and chlorotoluene), and the like. Examples of suitable solvents include organic solvents such as benzene, esters (e.g., methyl acetate, ethyl acetate, butyl acetate, diethyl carbonate, etc.), alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol, 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, etc.), as well as water. These solvents may be used alone or in combination of two or more. Among these solvents, organic solvents are preferred because they provide better effects of the present invention, and halogenated carbons or ketones are more preferred.

[0150] 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.

[0151] [Other Components] The composition may contain components other than the liquid crystal compound, specific organic dye, surfactant, and solvent (hereinafter also referred to as "other components"). Examples of the other components include a polymerization initiator and an adhesive agent.

[0152] [Electro-optical Layer] The electro-optical layer (hereinafter also referred to as "EO layer") of the present invention is an EO layer formed using the present composition described above, and the specific organic dye contained in the EO layer is oriented.

[0153] In the present invention, the degree of orientation of the specific organic dye contained in the EO layer is preferably 0.20 or more, more preferably 0.21 or more, even more preferably 0.30 or more, and particularly preferably 0.40 or more, because this reduces power consumption. While there is also a method of increasing the degree of orientation to 0.95 or more by crystallizing the specific organic dye, the crystallization of the specific organic dye causes light scattering from the fine particles, reducing the light transmission rate within the fiber. Therefore, the degree of orientation of the specific organic dye contained in the EO layer is preferably 0.99 or less, more preferably 0.98 or less, and even more preferably 0.95 or less. When the specific organic dye is not crystallized, there is no upper limit to the degree of orientation, but it is typically 0.99 or less. The degree of orientation of the specific organic dye is measured according to the method described in the Examples section below.

[0154] The orientation state of the specific organic dye and the liquid crystal compound 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 and the long axis direction of the specific organic dye or liquid crystal compound are parallel. 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 specific organic dye or liquid crystal compound 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 and the long axis direction of the specific organic dye or liquid crystal compound are perpendicular. 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 specific organic dye or liquid crystal compound and the major surface of the EO layer is 80 to 90°.

[0155] The surface roughness Ra of the EO layer is preferably 10 nm or less, more preferably 7 nm or less, and even more preferably 5 nm or less, in order to reduce transmission loss. The lower limit of the surface roughness Ra of the EO layer is not particularly limited, but is preferably 0.5 nm or more. The surface roughness Ra of the EO layer is measured according to the method described in the Examples section below.

[0156] The thickness of the EO layer is preferably 0.3 to 5.0 μm, and more preferably 1.0 to 3.0 μm, and 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)).

[0157] The method for forming the EO layer is not particularly limited, but an example is a method including, in this order, a step of applying the above-mentioned composition onto an alignment layer to form a coating film (hereinafter also referred to as the "coating film forming step"), and a step of orienting the liquid crystal compound and specific organic dye contained in the coating film (hereinafter also referred to as the "orientation step"), because this will result in a higher degree of orientation of the liquid crystal compound and specific organic dye in the resulting EO layer.

[0158] [Alignment Layer] The alignment layer may be any layer as long as it can achieve the desired alignment of the specific organic dye contained in the EO layer. Methods for forming the alignment layer include, for example, rubbing an organic compound (preferably a polymer) onto the film surface, oblique vapor deposition of an inorganic compound, formation of a layer with microgrooves, and accumulation of an organic compound (e.g., ω-tricosanoic acid, dioctadecylmethylammonium chloride, methyl stearate, etc.) by the Langmuir-Blodgett method (LB film). Furthermore, alignment layers that exhibit alignment function upon application of an electric field, a magnetic field, or light irradiation are also known.

[0159] The thickness of the alignment layer is not particularly limited, but is preferably 0.01 to 2.0 μm, and more preferably 0.01 to 1.0 μm. The thickness of the alignment 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)).

[0160] In the present invention, an alignment layer formed by rubbing treatment (rubbed alignment layer) is preferred from the viewpoint of ease of control of the pretilt angle of the alignment layer, and a photo-alignment layer formed by light irradiation is preferred from the viewpoint of uniformity of alignment.

[0161] <Rubbing Treatment Alignment Layer> Polymer materials used for the alignment layer formed by rubbing treatment are described in many literatures, and many commercially available products are available. In the present invention, polyvinyl alcohol or polyimide, and derivatives thereof are preferably used. For details of the alignment layer, please refer to the description on page 43, line 24 to page 49, line 8 of WO 2001 / 88574 A1.

[0162] <Photo-alignment layer> Photo-alignment compounds used in the alignment layer formed by light irradiation are described in many documents, etc. In the present invention, for example, azo compounds described in JP-A Nos. 2006-285197, 2007-76839, 2007-138138, 2007-94071, 2007-121721, 2007-140465, 2007-156439, 2007-133184, 2009-109831, Japanese Patent Nos. 3883848 and 4151746, azo compounds described in JP-A No. 2002-229039, Preferred examples include aromatic ester compounds described in JP-A Nos. 2002-265541 and 2002-317013, maleimide and / or alkenyl-substituted nadimide compounds having a photo-alignable unit, photo-crosslinkable silane derivatives described in Japanese Patent Nos. 4205195 and 4205198, and photo-crosslinkable polyimides, polyamides, or esters described in Japanese Patent Publication Nos. 2003-520878, 2004-529220, or Japanese Patent No. 4162850. More preferred are azo compounds, photo-crosslinkable polyimides, polyamides, or esters.

[0163] Among these, it is preferable to use a photosensitive compound having a photo-alignment group that undergoes at least one of dimerization and isomerization under the action of light as the photo-alignment compound.In addition, as the photo-alignment group, for example, a group having a cinnamic acid (cinnamoyl) structure (skeleton), a group having a coumarin structure (skeleton), a group having a chalcone structure (skeleton), a group having a benzophenone structure (skeleton), and a group having an anthracene structure (skeleton) can be mentioned.Among these groups, a group having a cinnamoyl structure and a group having a coumarin structure are preferred, and a group having a cinnamoyl structure is more preferred.

[0164] The photosensitive compound having the photoalignable group may further have a crosslinkable group. The crosslinkable group is preferably a thermally crosslinkable group that undergoes a curing reaction under the action of heat, or a photocrosslinkable group that undergoes a curing reaction under the action of light, and may be a crosslinkable group having both a thermally crosslinkable group and a photocrosslinkable group. Examples of the crosslinkable group include an epoxy group, an oxetanyl group, -NH-CH ２ Examples of the group include at least one selected from the group consisting of a group represented by -O-R (R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), a group having an ethylenically unsaturated double bond, and a blocked isocyanate group. Among these, an epoxy group, an oxetanyl group, and a group having an ethylenically unsaturated double bond are preferred. A three-membered cyclic ether group is also called an epoxy group, and a four-membered cyclic ether group is also called an oxetanyl group. Specific examples of the group having an ethylenically unsaturated double bond include a vinyl group, an allyl group, a styryl group, an acryloyl group, and a methacryloyl group, with an acryloyl group or a methacryloyl group being preferred.

[0165] A photo-alignment layer formed from the above materials is irradiated with linearly polarized or non-polarized light to produce a photo-alignment layer. In this specification, "linearly polarized light irradiation" and "non-polarized light irradiation" refer to operations for causing a photoreaction in the photo-alignment material. The wavelength of the light used varies depending on the photo-alignment material used, and is not particularly limited as long as it is the wavelength necessary for the photoreaction. The peak wavelength of the light used for photoirradiation is preferably 200 nm to 700 nm, and ultraviolet light with a peak wavelength of 400 nm or less is more preferred.

[0166] Examples of light sources used for light irradiation include commonly used light sources, such as lamps such as tungsten lamps, halogen lamps, xenon lamps, xenon flash lamps, mercury lamps, mercury xenon lamps, and carbon arc lamps, various lasers [e.g., semiconductor lasers, helium-neon lasers, argon ion lasers, helium-cadmium lasers, and YAG (yttrium aluminum garnet) lasers], light-emitting diodes, and cathode ray tubes.

[0167] As a means for obtaining linearly polarized light, a method using a polarizing plate (e.g., an iodine polarizing plate, a dichroic dye polarizing plate, and a wire grid polarizing plate), a method using a prism element (e.g., a Glan-Thompson prism) or a reflective polarizer utilizing the Brewster angle, or a method using light emitted from a polarized laser light source can be employed. Alternatively, a filter or a wavelength conversion element may be used to selectively irradiate only light of a required wavelength.

[0168] When the light to be irradiated is linearly polarized light, a method is adopted in which the light is irradiated from the top or back surface of the alignment layer perpendicularly or obliquely to the surface of the alignment layer. The incident angle of the light varies depending on the photo-alignment material, but is preferably 0 to 90° (perpendicular), and more preferably 40 to 90°. When the light is non-polarized light, the alignment layer is irradiated with non-polarized light obliquely. The incident angle is preferably 10 to 80°, more preferably 20 to 60°, and even more preferably 30 to 50°. The irradiation time is preferably 1 to 60 minutes, and more preferably 1 to 10 minutes.

[0169] When patterning is required, a method of irradiating light using a photomask the number of times required to form a pattern, or a method of writing a pattern by laser beam scanning can be used.

[0170] [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 state such as a molten liquid by heating or the like. Specific examples of the coating method of 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.

[0171] [Orientation Step] The orientation step is a step of orienting the specific 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 specific organic dye and liquid crystal compound contained in the composition may be oriented by the above-mentioned coating film formation step or drying treatment. For example, in an embodiment in which the 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.

[0172] The orientation step preferably includes a heat treatment. This allows the specific 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.

[0173] 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.

[0174] [Other Steps] The method for forming an EO layer may include a step of curing the EO layer (hereinafter also referred to as a "curing step") after the alignment step. For example, when a component contained in the EO layer (or the present composition) has a crosslinkable group (polymerizable group), the curing step is performed by heating and / or light irradiation (exposure). Among these, the curing step is preferably performed by light irradiation. The method for forming an EO layer may also include a step of performing a poling treatment after the alignment step (or the curing step). 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 is particularly preferred in terms of the simplicity of the apparatus and the high degree of alignment obtained. The electric field poling method is 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 a nonlinear optical material on a substrate electrode and a charging electric field is applied.

[0175] [Laminate] The laminate of the present invention has an alignment layer and an EO layer disposed on the alignment layer, and a substrate may be disposed on the surface of the alignment layer opposite to the EO layer. Hereinafter, each member constituting the laminate of the present invention will be described.

[0176] [Substrate] The substrate is not particularly limited, and examples thereof include a resin substrate, a semiconductor substrate, an inorganic substrate (e.g., a glass substrate), and a metal substrate, and these substrates may have a conductive film formed on the surface thereof.

[0177] [Electro-Optical Layer] The EO layer has been described above, and therefore a detailed description thereof will be omitted.

[0178] [Alignment Layer] The alignment layer is as described above, and therefore a description thereof will be omitted.

[0179] [Uses] The laminate of the present invention can be used as an optical element. Specific examples of optical elements include wavelength conversion elements, photorefractive elements, and electro-optical elements. Among these, it is preferable to use the laminate in electro-optical elements such as optical switches, optical modulators, and phase shifters that operate based on the electro-optical effect.

[0180] The present invention will be described in more detail below with reference to examples. The materials, amounts used, ratios, treatment details, and treatment procedures 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.

[0181] [Example 1] <Formation of Alignment Layer> The following alignment layer composition 1 was applied by spin coating onto a glass substrate on which ITO had been sputtered, and dried at 100°C for 1 minute to form an alignment layer 1 having a thickness of 0.5 µm.

[0182] ------------------------------------------------------------------ Alignment layer forming composition 1 -------------------------------------------------- Polyvinyl alcohol (Poval 3-88; manufactured by Kuraray) 2.1 parts by mass Methanol 44.4 parts by mass Distilled water 53.5 parts by mass ------------------------------------------------------------------

[0183] <Formation of EO layer 1> The following composition for forming an electro-optical layer 1 was applied by spin coating onto the alignment layer 1 and aged for 30 seconds at 130°C to form an EO layer 1 (thickness 1.8 µm) in which the liquid crystal compound L1 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.

[0184] ----------------------------------------------- Electro-optical layer forming composition 1 ------------------------------------------------------------------ 0.0917 parts by mass of liquid crystal compound L1 shown below 0.0100 parts by mass of organic dye E1 shown below 0.0010 parts by mass of surfactant S1 shown below 0.8973 parts by mass of chloroform

[0185]

[0186] The liquid crystal compound L1 has a mass ratio of the constituent units, from left to right, of 72.0:18.0:10.0, and a weight average molecular weight of 18,000.

[0187]

[0188]

[0189] The surfactant 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.

[0190] The obtained laminate 1 was placed on a hot plate and subjected to corona poling treatment. Specifically, the 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 the EO layer 1. From that state, the laminate 1 was air-cooled to 23°C over 10 minutes while the charging voltage was still applied, and then the charging voltage was removed.

[0191] [Examples 2 to 8, Comparative Examples 1 and 2] Laminates of each of the Examples and Comparative Examples were obtained in the same manner as in Example 1, except that compositions for forming an electro-optical layer having the compositions shown in Table 1 were used instead of the composition for forming an electro-optical layer 1. The structure of each component shown in Table 1 is shown below.

[0192]

[0193] Liquid crystal compound L1 has a mass ratio of the constituent units, from left to right, of 72.0:18.0:10.0, and a weight-average molecular weight of 18000. Liquid crystal compound L2 has a mass ratio of the constituent units, from left to right, of 75.0:25.0, and a weight-average molecular weight of 25000.

[0194]

[0195] The liquid crystal compound L3 is a mixture of three low molecular weight liquid crystal compounds, and the mixing ratio (mass ratio) of the compounds is 82.0:15.0:3.0 from top to bottom.

[0196]

[0197] The second-order molecular susceptibility, L / D ratio (aspect ratio), and θeg of each organic dye were measured by the methods described above. The results are shown in Table 1 below.

[0198]

[0199] The surfactant 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 16000. The surfactant S2 has a mass ratio of the constituent units, from left to right, of 37.0:12.0:13.0:38.0, and a weight-average molecular weight of 18000.

[0200] Example 9 A laminate of Example 9 was obtained in the same manner as in Example 2, except that alignment layer 2 prepared as follows was used instead of alignment layer 1. <Formation of alignment film> The alignment layer composition 2 described below 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 applied layer. ２ An alignment layer 2 having a thickness of 0.5 μm was formed by irradiating the film with light from a super-high pressure mercury lamp.

[0201] ------------------------------------------------------------------ Alignment layer forming composition 2 -------------------------------------------------- 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

[0202]

[0203] The weight average molecular weight of the polymer PA1 is 19,000.

[0204] [Evaluation] <Orientation Degree> The orientation degree of the organic dye 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 electro-optical 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 electro-optical layer, and "Ay0" represents the absorbance for polarized light in the transmission axis direction of the electro-optical layer.

[0205] <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)

[0206] (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

[0207] <Change in electro-optic constants over time (r1 / r0)> The following evaluation was carried out to examine the change in electro-optic constants over time. The laminate that had been subjected to the corona poling treatment was left at room temperature (23°C) for one day, and the r value was calculated in the same manner as for r0, except that this was used. The obtained r value was designated as r1. The change in the electro-optic 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.

[0208] (Evaluation criteria) A: 0.8 or more B: Less than 0.8

[0209] <Unevenness> The surface of the EO layer of the laminate that had been subjected to the corona poling treatment was observed at three arbitrary locations over an area of ​​620 μm x 465 μm at a resolution of 640 x 480 pixels using a Bartscan 2.0 (model number: R5300H) manufactured by Ryoka Systems Co., Ltd., and the surface roughness Ra of the three locations was measured. The unevenness of the surface of the EO layer was evaluated based on the arithmetic mean value of the surface roughness Ra of the three locations. The results are shown in Table 1 below. Note that the smaller the Ra value, the less unevenness there is on the surface of the EO layer, and therefore the lower the transmission loss due to the EO layer. (Evaluation criteria) A: The arithmetic mean value of Ra is 10 nm or less B: The arithmetic mean value of Ra is greater than 10 nm

[0210]

[0211] As shown in Table 1, the use of this composition allows the formation of an EO layer exhibiting a high electro-optic constant, and the reduced surface roughness of the EO layer results in reduced transmission loss (Examples). Comparison of Examples 1 to 9 demonstrated that the degree of orientation of the organic dye was superior when the aspect ratio of the organic dye molecules was 2.0 or greater and / or θeg was 10.0° or less (Examples 1 to 5, Examples 7 to 9). In particular, the degree of orientation of the organic dye was particularly superior when both the aspect ratio of the organic dye molecules was 2.0 or greater and θeg was 10.0° or less (Examples 1 to 3, Examples 7 to 9).

[0212] In contrast, without surfactant, the second-order molecular susceptibility is 400,000 × 10 －３３ When a composition containing an organic dye less than esu is used, an EO layer with a low electro-optic constant is formed, and the surface roughness of the EO layer is large, which can be said to result in large transmission loss (Comparative Example 1).When a composition containing no surfactant is used, the surface roughness of the EO layer is large, which can be said to result in large transmission loss (Comparative Example 2).

Claims

1. Liquid crystal compound with a second-order molecular susceptibility of 400,000 x 10 －３３ A composition for forming an electro-optical layer, comprising: an organic dye having a molecular weight of esu or more; and a surfactant.

2. The composition for forming an electro-optical layer according to claim 1, wherein the organic dye has a molecular aspect ratio of 2.0 or more.

3. The composition for forming an electro-optical layer according to claim 1, wherein the angle θeg 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.

4. The composition for forming an electro-optical layer according to claim 1, wherein the organic dye is a compound represented by the following formula (E1): In the formula (E1), R represents a hydrogen atom, or an alkyl group, an aryl group, or a heterocyclic group, each of which may have a substituent; ２ - may be substituted with a divalent substituent, when n is 2 or more, two or more R may be the same or different and may be bonded to each other to form a ring containing E1, E1 represents an oxygen atom, a sulfur atom, or a nitrogen atom, A1 represents -C(R Ａ１ ) = C(R Ａ２ )-, or an optionally substituted arylene group or heterocyclic group, 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, and A1 is -C(R Ａ１ ) = C(R Ａ２ )-, then R Ａ１ and R may be bonded to form a ring containing E1; A2 represents a single bond, or an arylene group or a heterocyclic group which may have a substituent; when m is 2 or more, two or more A2 may be the same or different; 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-, when n1 or m is 2 or more, two or more L1s may be the same or different, when n2 is 2 or more, two or more L2s may be the same or different, when n1 is 2 or more, adjacent L1s may be bonded to each other to form a ring, when n2 is 2 or more, adjacent L2s may be bonded to each other to form a ring, when L1 and L2 are adjacent, adjacent L1 and L2 may be bonded to each other to form a ring, R Ｌ１ , R Ｌ２ , and R Ｌ４ each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, an alkyl group having 1 to 15 carbon atoms, an aryl group having 6 to 20 carbon atoms, —O—Si(R Ｌ５ ) ３ or a group formed by combining two or more of these groups; ２ - may be substituted with a divalent substituent, and multiple R Ｌ５ each independently represents a hydrogen atom, an alkyl group, or a phenyl group; ２ is -C(R Ｅ２１ ) (R Ｅ２２ )-, -C(=O)-, -C(=S)-, or -C(=NR Ｅ４ )-, R Ｅ２１ and R Ｅ２２ 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, and -CH ２ - may be substituted with a divalent substituent, the hydrogen atoms of the alkyl group and the aryl group may be substituted with a monovalent substituent, R 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, ３ is -O-, -S-, -N(R Ｅ５ )- or -S(=O)-, R Ｅ５ represents a hydrogen atom, or an optionally substituted 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; n represents an integer of 1 or 2; n1 represents an integer of 0 to 3; n2 represents an integer of 0 to 3; and m represents an integer of 0 to 4.

5. An electro-optical layer formed using the composition for forming an electro-optical layer according to any one of claims 1 to 4, wherein an organic dye contained in said electro-optical layer is oriented.

6. The electro-optic layer of claim 5, wherein the degree of orientation of said organic dye is greater than 0.

3.

7. A laminate comprising an alignment layer and an electro-optic layer according to claim 5 disposed on said alignment layer.

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