JP2002179668A - Optically active compound, liquid crystal chiral agent, liquid crystal composition, liquid crystal color filter, optical film and recording medium - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an optically active compound (chiral agent) having large twisting power (twist angle) of a liquid crystal. SOLUTION: The optically active compound is expressed by formula (I) [R1 is a halogen atom, an aryl, an alkynyl, formyl, CH=CH-R3, C(R4)=CH2 OR CH=C(R5)2; R3 and R4 are each an aryl; R5 is an alkoxycarbonyl, an aryloxycarbonyl or cyano; R2 is an alkyl or an aryl; and binaphthyl group has (R) or (S) axial asymmetry].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel optically active compound, a liquid crystal chiral agent, a liquid crystal composition, a liquid crystal color filter, an optical film, and a recording medium.

[0002]

2. Description of the Related Art A liquid crystal phase containing a chiral compound often has excellent optical properties. For example, a cholesteric phase in which liquid crystal compound molecules have a helical arrangement can be formed by, for example, doping a nematic liquid crystal phase with a chiral compound. Such cholesteric phases often exhibit a colored interference effect due to the selective reflection of light of a certain wavelength in the helical liquid crystal structure. These colored cholesteric phases can be fixed, for example, by cooling below the glass transition temperature or by incorporation into a polymer network, whereby the colored coating of the phase or with interference pigments It becomes possible to use as.

For example, a color filter used for a color liquid crystal display or the like generally includes red (R), green (G), and blue (B) pixels, and a black matrix for improving display contrast in a gap between the pixels. Is formed. Conventionally, such a color filter is
The mainstream is a resin in which a pigment is dispersed or a dye is dyed, and the manufacturing method is also to apply a colored resin liquid onto a glass substrate by spin coating or the like to form a colored resist layer, In general, a method of forming a color filter pixel by performing patterning by a lithography method or printing a colored pixel directly on a substrate has been used.

However, for example, the manufacturing method by the printing method has a disadvantage that it is difficult to form a high-definition image pattern with low pixel resolution, and the manufacturing method by the spin coating method causes a large material loss and a large loss. There is a drawback that coating unevenness when coating on a substrate having a large area is large. Further, according to the production method by the electrodeposition method, it is possible to obtain a color filter having relatively high resolution and less unevenness of the colored layer, but has a disadvantage that the production process is complicated and liquid management is difficult.

[0005] As described above, as a process for producing a color filter, there has been a demand for a method capable of producing a high-quality color filter with high efficiency and efficiency with little material loss.

On the other hand, the performance of the color filter is as follows.
Transmittance, high color purity is required, in recent years, in the method using a dye, to optimize the type and dyeing resin of the dye, or in the method using a pigment, by using a finely dispersed pigment, Improvements have been made. However, in recent liquid crystal display (LCD) panels, there is an extremely high demand for the transmittance and color purity of the color filters.
And while it is difficult to achieve both color reproducibility, in the conventional manufacturing method, dyes are dyed in the resin, or the color filters manufactured by dispersing the pigment, because all are light absorption type color filters The improvement in color purity by further improving the transmittance has almost reached the limit.

[0007] Under such circumstances, a polarization type color filter mainly comprising cholesteric liquid crystal has been known. This color filter using polarized light reflects a certain amount of light and transmits the rest of the image to display an image.Therefore, the light use efficiency is high and the transmittance and color purity are superior to the light absorption type color filter. It has the performance which it did.
On the other hand, in the manufacturing method, from the viewpoint of obtaining a uniform thickness,
Although a method of forming a film on a substrate by using a spin coating method or the like has been generally performed, there is a problem that a material loss is large and disadvantageous in cost.

A method using a photoreactive chiral compound as a means for solving the above problems and ensuring uniformity of the color purity and the like of a color filter film and also realizing a reduction in the number of manufacturing steps. Useful. In this method, when a liquid crystal composition containing a photoreactive chiral compound is irradiated with light having a reaction wavelength of the chiral compound in a pattern, the reaction of the chiral compound proceeds in accordance with the intensity of the irradiation energy,
Since the helical pitch (helical twist angle) of the liquid crystal compound changes, the principle is used that a selective reflection color is formed for each pixel only by pattern exposure having a light amount difference. That is, there is an advantage that the number of times of patterning at the time of forming the color filter can be completed by one mask exposure using masks having different transmitted light amounts.

Therefore, a film functioning as a color filter can be formed by patterning by irradiating light imagewise and then fixing the patterned cholesteric liquid crystal compound. This can also be applied to optical films and image recording.

On the other hand, when the three primary colors of red (R), green (G), and blue (B) cannot be formed with good color purity by using only the photoreactive chiral agent, a chiral agent having no photoreactivity is added. It is necessary to adjust the selective reflection wavelength, compatibility with the liquid crystal, and the like. Numerous compounds have been disclosed as such chiral agents (for example, German Patent Application 43
42280). A suitable dopant should have a high torsional force so that a small amount of dopant is sufficient to induce a helical structure. Furthermore, the chiral dopant should have good compatibility with the liquid crystal compound. This allows for effective interaction between the components. With respect to this property, many of the chiral dopants known hitherto are not satisfactory.

For example, for a compound in which the hydroxyl group of 1,1'-bi-2-naphthol is cyclized with an alkylene group,
J. Am. Chem. Soc. , 1983, 105 , 7
318, which is used as a liquid crystal chiral agent, but is not sufficient in terms of torsional force. Also, 1,1 '
-Bi-2-naphthol is a compound in which a phthalic acid ester is used. Soc. Chim. Fr. <3
>, 1899, 21 , 656, a biphenyl carboxylate ester is described in Bull. Chem.
Soc. Jpn. , 1998, 61 , 3249, but those having substituents at the 6-position and 6'-position of the binaphthyl moiety are not known, and there is no example of use of the liquid crystal composition as a chiral agent. .

[0012]

SUMMARY OF THE INVENTION An object of the present invention is to solve the above-mentioned conventional problems and achieve the following objects. That is,

An object of the present invention is to provide an optically active compound having a large twisting power (twisting angle) of a liquid crystal. Secondly, it is an object of the present invention to provide a liquid crystal chiral agent which has a large twisting force of a liquid crystal, enables a wide range of selective reflection including three primary colors in a cholesteric liquid crystal phase, and can display three primary colors having high color purity. I do.

Third, it contains an optically active compound having a large twisting power of liquid crystal, exhibits a wide range of selective reflection colors including the three primary colors (B, G, R) by light irradiation, and has excellent color purity. It is an object to provide a liquid crystal composition capable of displaying.

A fourth object of the present invention is to provide a liquid crystal color filter having a high color purity and containing an optically active compound having a large liquid crystal twisting force. Fifth, it is an object to provide an optical film containing an optically active compound having a large twisting power of a liquid crystal, having a wide selective reflection region and a high color purity. Sixth, an object is to provide a recording medium that contains a large optically active compound having a large twisting power of liquid crystal and can form an image composed of a selective reflection color having a wide range and high color purity by changing the amount of light imagewise. I do.

[0016]

Means for solving the above problems are as follows. That is, <1> an optically active compound represented by the following general formula (I).

Embedded image [Wherein, R ¹ represents a halogen atom, an aryl group, an alkynyl group, a formyl group, —CH ＝ CH—R ² , —C (R ³ ) =
CH ₂ , —CH ＝ C (R ⁴ ) ₂ , where R ² and R ³
Represents an aryl group, and R ⁴ represents an alkoxycarbonyl group, an aryloxycarbonyl group, or a cyano group. L ¹ represents an alkylene group, alkenylene group, or arylene group. The binaphthyl moiety has either (R) or (S) axial asymmetry. <2> A liquid crystal chiral agent comprising an optically active compound represented by the following general formula (II).

Embedded image Wherein R ⁵ is a hydrogen atom, a halogen atom, an aryl group, an alkynyl group, a formyl group, —CH ＝ CH—R ⁶ ,
—C (R ⁷ ) ＝ CH ₂ , —CH ＝ C (R ⁸ ) ₂ , wherein R ⁶ and R ⁷ represent an aryl group, and R ⁸ represents an alkoxycarbonyl group, an aryloxycarbonyl group, or a cyano group. Represent. L ² represents an alkylene group, alkenylene group, or arylene group. The binaphthyl moiety has either (R) or (S) axial asymmetry. [3] A liquid crystal composition containing at least a liquid crystal compound and at least one chiral agent according to <2>. <4> A liquid crystal composition containing a liquid crystalline compound having at least one functional site capable of being polymerized, a photopolymerization initiator, and at least one chiral agent according to <2>. <5> a liquid crystalline compound having at least one ethylenic double bond capable of addition polymerization, a photopolymerization initiator, and the above <2>
A liquid crystal composition comprising at least one chiral agent according to item 1. <6> A liquid crystal color filter containing at least a liquid crystal compound and the chiral agent according to <2>. <7> An optical film containing at least a liquid crystal compound and the chiral agent according to <2>. <8> A recording medium containing at least a liquid crystalline compound and the chiral agent according to <2>.

DESCRIPTION OF THE PREFERRED EMBODIMENTS The details of the present invention will be described below in order, but the present invention is not limited to these.

<Optically Active Compound> The optically active compound of the present invention is a compound represented by the following general formula (I).

[0018]

Embedded image In the above formula, R ¹ is a halogen atom, an aryl group, an alkynyl group, a formyl group, —CH ＝ CH—R ² , —C (R ³ )
ＣＨCH ₂ , —CH ＝ C (R ⁴ ) ₂ , where R ² and R
³ represents an aryl group, and R ⁴ represents an alkoxycarbonyl group, an aryloxycarbonyl group, or a cyano group. L ¹ represents an alkylene group, alkenylene group, or arylene group. The binaphthyl moiety has either (R) or (S) axial asymmetry.

<Compound of the general formula (I)> The halogen atom represented by R ¹ is preferably a fluorine atom, a chlorine atom or a bromine atom, particularly preferably a bromine atom.

The aryl group represented by R ¹ may have a substituent or may be a heterocyclic ring, and is preferably an aryl group having 4 to 40 carbon atoms, particularly preferably an aryl group having 4 to 30 carbon atoms. Is preferred. Preferred examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group. Particularly, a halogen atom, an alkyl group, an alkenyl group, an alkoxy group and an acyloxy group are preferred. As the heterocyclic ring, for example, a pyridine ring, a pyrimidine ring, a furan ring, and a benzofuran ring are preferable, and a pyridine ring and a pyrimidine ring are particularly preferable.

Examples of such aryl groups include phenyl, β-naphthyl, 4-methylphenyl, 4-
Vinylphenyl group, 4-butyloxyphenyl group, 4-
Examples include a benzoyloxyphenyl group and a pyrimidin-2-yl group.

The alkynyl group represented by R ¹ may have a substituent, and is preferably an alkynyl group having 2 to 30 carbon atoms, particularly preferably an alkynyl group having 2 to 20 carbon atoms.
Examples of the substituent include a halogen atom, an aryl group,
Alkenyl groups, alkoxy groups, acyl groups, alkoxycarbonyl groups, aryloxycarbonyl groups, asiloxy groups, and cyano groups are preferred. Particularly, an aryl group and an acyloxy group are preferable.

Examples of such an alkynyl group include an ethynyl group, a phenylethynyl group and a 4-acetyloxyphenylethynyl group.

The aryl group represented by R ² may have a substituent or may be a heterocyclic ring, and is preferably an aryl group having 4 to 40 carbon atoms, particularly preferably an aryl group having 4 to 30 carbon atoms. Is preferred. Preferred examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group. Particularly, electron-withdrawing groups such as an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, and a cyano group are preferable. As the heterocyclic ring, for example, a pyridine ring, a pyrimidine ring, a furan ring, and a benzofuran ring are preferable, and a pyridine ring and a pyrimidine ring are particularly preferable.

Examples of such aryl groups include phenyl, 4-butoxycarbonylphenyl, 4-benzoylphenyl, 4-naphthyloxycarbonylphenyl, 6-methoxycarbonylnaphthalen-2-yl and the like. Can be

The aryl group represented by R ³ may have a substituent or may be a heterocyclic ring, and is preferably an aryl group having 4 to 40 carbon atoms, particularly preferably an aryl group having 4 to 30 carbon atoms. Is preferred. Preferred examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group. Particularly, an electron donating group such as an alkyl group, an alkenyl group and an alkoxy group is preferable. As the heterocyclic ring, for example, a pyridine ring, a pyrimidine ring, a furan ring, and a benzofuran ring are preferable, and a pyridine ring and a pyrimidine ring are particularly preferable.

Examples of such an aryl group include 4-
Examples include a methylphenyl group, a 4-vinylphenyl group, a 4-butyloxyphenyl group, and a 4-benzoyloxyphenyl group.

The alkoxycarbonyl group represented by R ⁴ may have a substituent, and is preferably an alkoxycarbonyl group having a total of 2 to 30 carbon atoms, particularly preferably an alkoxycarbonyl group having 2 to 20 carbon atoms. Preferred examples of the substituent include a halogen atom, an aryl group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group. Particularly, a halogen atom, an aryl group, an alkoxy group and an acyloxy group are preferred.

Examples of such an alkoxycarbonyl group include a methoxycarbonyl group, a decyloxycarbonyl group, a trifluoroethoxycarbonyl group, a methoxyethoxycarbonyl group, and an acetyloxyethoxycarbonyl group. ,

The aryloxycarbonyl group represented by R ⁴ may have a substituent or may be a heterocyclic ring, and is preferably an aryloxycarbonyl group having 5 to 40 carbon atoms. Up to 30 aryloxycarbonyl groups are preferred. Preferred examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group. In particular, a halogen atom, an alkyl group, an alkoxy group,
An arylcarbonyl group, an acyloxy group and a cyano group are preferred.

Examples of such an aryloxycarbonyl group include, for example, a phenoxycarbonyl group, a biphenyloxycarbonyl group, a β-naphthyloxycarbonyl group, a 4-phenoxycarbonylphenoxycarbonyl group, a methoxyphenoxycarbonyl group and the like.

In the above groups represented by R ¹ ,
A halogen atom, an alkynyl group and —C (R ³ ) ＝ CH ₂ are preferred, and a halogen atom and —C (R ³ ) ＝ CH ₂ are particularly preferred.

The alkylene group represented by L ¹ may have a substituent, and is preferably an alkylene group having 1 to 30 carbon atoms, particularly preferably an alkylene group having 2 to 20 carbon atoms. Examples of the substituent include a halogen atom, an aryl group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group,
An alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, and a cyano group are preferred. In particular, the following alkylene groups are preferred.

[0034]

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The alkenylene group represented by L ¹ may have a substituent, and is preferably an alkylene group having 2 to 30 carbon atoms, and more preferably an alkylene group having 2 to 20 carbon atoms.
Examples of the substituent include a halogen atom, an alkyl group,
Aryl group, alkynyl group, alkoxy group, acyl group,
An alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, and a cyano group are preferred. In particular, the following alkenylene groups are more preferred.

[0036]

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The arylene group represented by L ¹ may have a substituent or may be a heterocyclic ring, and is preferably an arylene group having 4 to 30 carbon atoms, particularly preferably an arylene group having 4 to 20 carbon atoms. Groups are preferred. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group,
Preferred are an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, an acylamino group, and a cyano group. Examples of the heterocycle include a pyridine ring, a pyrazine ring, a furan ring, and a benzofuran ring. Of these, the following arylene groups are preferred.

[0038]

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Particularly, the following arylene groups are most preferred.

[0040]

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An aryl group represented by R ¹ , an alkynyl group, an aryl group represented by R ² , an aryl group represented by R ³ , an alkoxycarbonyl group represented by R ⁴ , an aryloxycarbonyl group, and L ^The alkylene group, alkenylene group, and arylene group represented by ¹ may each be substituted with the following general formula (III).

[0042]

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<Compound of General Formula (II)> The chiral agent of the liquid crystal of the present invention comprises an optically active compound represented by the following general formula (II).

[0044]

Embedded image In the above formula, R ⁵ is a hydrogen atom, a halogen atom, an aryl group, an alkynyl group, a formyl group, —CH ＝ CH—R ⁶ ,
—C (R ⁷ ) ＝ CH ₂ , —CH ＝ C (R ⁸ ) ₂ , wherein R ⁶ and R ⁷ represent an aryl group, and R ⁸ represents an alkoxycarbonyl group, an aryloxycarbonyl group, or a cyano group. Represent. L ² represents an alkylene group, alkenylene group, or arylene group. The binaphthyl moiety has either (R) or (S) axial asymmetry.

The functional group represented by R ⁵ in the above general formula (II) is the same as each functional group represented by R ¹ in the above general formula (I) except that it further contains a hydrogen atom. It is.
The functional group represented by L ² in the general formula (II) is the same as each functional group represented by L ¹ in the general formula (I).

Hereinafter, specific examples of the optically active compound of the present invention represented by the general formula (I) will be described with reference to Exemplified Compounds 1-1 to 1
-20, but the present invention is not limited to these.

[0047]

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[0048]

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As specific examples of the optically active compound of the present invention represented by the general formula (II), in addition to the specific examples of the optically active compound represented by the general formula (I), the following exemplary compounds Although 2-1 to 2-11 are shown, the present invention is not limited to these.

[0050]

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(Production method) The optically active compound of the present invention can be produced, for example, by the method of the following reaction formula (1).

[0052]

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The compound A (binaphthols) is a commercially available product or Chem. Soc. Chem. Comm
un. (3), 1994, 249; Che
m. Soc. Perkin. Trans. l, (1
3), 1998, 2097 and the like. Compound B can be produced by converting a commercially available product or a corresponding carboxylic acid or carboxylic anhydride into an acid halide. The esterification of the compound A and the compound B can be performed by a known method, for example, see the Chemical Society of Japan, 4th edition, Experimental Chemistry Lectures, pages 22, 43-83 (Maruzen).

<Chiral Agent for Liquid Crystal> The chiral agent for the liquid crystal of the present invention comprises an optically active compound represented by the general formula (II), and imparts a helical twisting power (HTP: helical twisting power) to the liquid crystal. It has characteristics that can be given and changed. That is, it is a compound that imparts or changes the torsional force of the helical structure induced in a liquid crystal compound, preferably a nematic liquid crystal compound, and has a chiral site as a necessary site (molecular structural unit).

The HTP represents the twisting force of the helical structure of the liquid crystal, that is, HTP = 1 / (pitch × concentration of chiral agent [weight fraction]). For example, the helical pitch of liquid crystal molecules at a certain temperature ( One period of the helical structure; μm) is measured, and this value can be obtained by conversion [μm-1] from the concentration of the chiral agent.

The liquid crystal chiral agent represented by the general formula (II) can greatly change the twisting power of the helical structure of the liquid crystal, and one or more polymerizable bonding groups are introduced into the structure. In the case of such a structure, the heat resistance of a liquid crystal composition or a liquid crystal composition containing the same, for example, a liquid crystal color filter or an optical film can be improved.

The molecular weight of the liquid crystal chiral agent comprising the optically active compound represented by the general formula (II) is 40
0 or more is preferable. Further, those having high solubility with a liquid crystal compound described later are preferable, and those having a solubility parameter SP value close to that of the liquid crystal compound are more preferable.

The content of the chiral agent of the present invention in the liquid crystal composition is not particularly limited, but is preferably about 0.1 to 30% by mass, and is preferably selected so as to obtain desired selective reflection.

Further, it can be used in combination with a known chiral agent.
44451, Tokiohei 10-509726, WO98 / 0
0428, Tokio 2000-506873, Tokiohei 9-5
06088, “Liquid Crystals” (19
96, 21 , 327) and (1998, 24 , 219).
And the like.

Further, in the production of a liquid crystal color filter or the like, it can be used in combination with a photoreactive chiral agent as described below, if necessary.

<Liquid Crystal Composition> The liquid crystal composition of the present invention contains at least the optically active compound of the present invention, that is, a chiral agent, and further contains at least one liquid crystal compound, preferably a nematic liquid crystal compound. , As necessary, a photoreactive chiral agent, a polymerizable monomer, a polymerization initiator, a binder resin, a solvent, a surfactant, a polymerization inhibitor, a thickener, a dye, a pigment, an ultraviolet absorber, a gelling agent, and the like. And other components.

The liquid crystal composition of the present invention is preferably used in combination with a surfactant. For example, when a liquid crystal composition in a coating liquid is applied to form a layer, the alignment state at the air interface on the layer surface can be three-dimensionally controlled, and a selective reflection wavelength with higher color purity can be obtained.

(Liquid Crystal Compound) The liquid crystal compound is characterized in that its liquid crystal phase is fixed below the liquid crystal transition temperature, and has a refractive index anisotropy Δn of 0.1.
0 to 0.40 low-molecular liquid crystal compound, high-molecular liquid crystal compound,
Although it can be appropriately selected from polymerizable liquid crystal compounds, a nematic liquid crystal compound is preferable. While in the liquid crystal state at the time of melting, alignment can be performed using, for example, an alignment substrate that has been subjected to alignment processing such as rubbing. In the case where the liquid crystal state is fixed in a solid phase, a means such as cooling or polymerization can be used.

Specific examples of the liquid crystal compound include the following compounds. However, the present invention is not limited to these.

[0065]

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[0066]

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[0067]

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In the above formula, n represents an integer of 1 to 1000. In each of the above exemplified compounds, those in which the connecting group of the aromatic ring is changed to the following structure can also be mentioned as suitable compounds.

[0069]

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Of the above, from the viewpoint of ensuring sufficient curability and improving the heat resistance of the layer,
Liquid crystalline compounds having a polymerizable group or a crosslinkable group in the molecule are preferred. As the polymerizable group, an ethylenic double bond is preferable.

The content of the liquid crystal compound is preferably from 30 to 99.9% by mass, more preferably from 50 to 95% by mass, based on the solid content of the liquid crystal composition. The content is
If the amount is less than 30% by mass, the orientation is insufficient and a desired selective reflection color may not be obtained.

(Photoreactive Chiral Agent) In the liquid crystal composition of the present invention, a photoreactive chiral agent may be used in combination. The photoreactive chiral agent changes its structure when irradiated with light in a desired pattern and light amount, thereby changing the twisted structure of a coexisting liquid crystal compound, preferably a nematic liquid crystal compound, and A selective reflection color in a wavelength region can be developed. The content of the photoreactive chiral agent in the liquid crystal composition is not particularly limited and can be appropriately selected, but is preferably 0 to 20% by mass. Examples of the photoreactive chiral agent include Japanese Patent Application No. 2000-193142 and Japanese Patent Application No. 200-193142.
No. 0-193143.

(Polymerizable Monomer) A polymerizable monomer may be used in the liquid crystal composition of the present invention. When the polymerizable monomer is used in combination, the helical structure (selective reflectivity) can be fixed, and the strength of the liquid crystal composition after the fixing can be further improved. However, when the liquid crystal compound has a polymerizable group in the same molecule, it is not always necessary to add.

Examples of the polymerizable monomer include monomers having an ethylenically unsaturated bond, and specific examples include polyfunctional monomers such as pentaerythritol tetraacrylate and dipentaerythritol hexaacrylate.

Specific examples of the monomer having an ethylenically unsaturated bond include the following compounds. However, the present invention is not limited to these.

[0076]

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The amount of the polymerizable monomer to be added is preferably 0.5 to 50% by mass based on the weight of the solid content of the liquid crystal composition. When the addition amount is less than 0.5% by mass,
In some cases, sufficient curability cannot be obtained, and when it exceeds 50% by mass, the alignment of liquid crystal molecules is hindered, and sufficient color formation may not be obtained.

(Polymerization Initiator) To fix the helical structure and further improve the strength of the liquid crystal composition after the immobilization, a photopolymerization initiator is added for the purpose of accelerating the polymerization reaction by the polymerizable group. You can also.

The photopolymerization initiator can be appropriately selected from known ones, for example, p-methoxyphenyl-2,4-bis (trichloromethyl) -s-triazine, 2- (p-butoxy) (Styryl) -5-trichloromethyl-1,3,4-oxadiazole, 9-phenylacridine, 9,10-dimethylbenzphenazine, benzophenone / Michler's ketone, hexaarylbiimidazole / mercaptobenzimidazole, benzyldimethylketal, thioxanthone / Amines, triarylsulfonium hexafluorophosphate,
Bisacylphosphine oxides such as bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide described in JP-A-10-29997; Luci;
acyl phosphine oxides described in DE 4230555 of rin TPO and the like.

The amount of the photopolymerization initiator to be added is preferably 0.1 to 20% by mass, more preferably 0.5 to 5% by mass, based on the solid content of the liquid crystal composition. If the amount is less than 0.1% by mass, the curing efficiency at the time of light irradiation is low, so that it may take a long time. If the amount exceeds 20% by mass, the light transmittance from the ultraviolet region to the visible light region may be required. May be inferior.

(Other Components) Further, other components include a binder resin, a solvent, a surfactant, a polymerization inhibitor, a thickener,
Dyes, pigments, ultraviolet absorbers, gelling agents and the like can also be added.

Examples of the binder resin include polystyrene compounds such as polystyrene and poly-α-methylstyrene, cellulose resins such as methylcellulose, ethylcellulose and acetylcellulose, acidic cellulose derivatives having a carboxyl group in the side chain, polyvinylformal, and the like. Acetal resins such as polyvinyl butyral, JP-A-59-44615, JP-B-54-34327,
JP-B-58-12577, JP-B-54-25957
JP-A-59-53836, JP-A-59-7104
No. 8, methacrylic acid copolymer, acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, maleic acid copolymer, partially esterified maleic acid copolymer and the like.

The homopolymer of an alkyl acrylate and the homopolymer of an alkyl methacrylate are also exemplified. In these, the alkyl group is a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an iso-group.
-Butyl group, n-hexyl group, cyclohexyl group, 2-
Examples thereof include an ethylhexyl group.

In addition, a polymer having a hydroxyl group to which an acid anhydride is added, benzyl (meth) acrylate /
(Homopolymer of methacrylic acid) Examples include acrylic acid copolymers and multi-component copolymers of benzyl (meth) acrylate / (meth) acrylic acid / other monomers.

The content of the binder resin in the liquid crystal composition is preferably from 0 to 50% by mass, more preferably from 0 to 30% by mass. If the content exceeds 50% by mass, the orientation of the liquid crystal compound may be insufficient.

In the liquid crystal composition of the present invention, it is preferable to use a surfactant together with a chiral agent for liquid crystals and a liquid crystal compound. As the surfactant, a surfactant having an excluded volume effect is preferable. Here, exerting the excluded volume effect means, for example, when a layer containing a liquid crystal composition is formed by coating, three-dimensionally controlling the spatial alignment state at the air interface on the surface of the layer. Specifically, a nonionic surfactant is preferable, and a nonionic surfactant can be appropriately selected from known nonionic surfactants.

The polymerization inhibitor may be added for the purpose of improving the storage stability. Examples include hydroquinone, hydroquinone monomethyl ether, phenothiazine, benzoquinone, and derivatives thereof. The addition amount of the polymerization inhibitor is 0 to 1 with respect to the polymerizable monomer.
0 mass% is preferable, and 0 to 5 mass% is more preferable.

The liquid crystal composition of the present invention can be prepared by dissolving and dispersing each of the above-mentioned components in an appropriate solvent, and can be used by shaping it into an arbitrary shape or forming it on a support or the like. . Here, examples of the solvent include 2-butanone, cyclohexanone, methylene chloride, chloroform and the like.

When the chiral agent represented by the general formula (II) is used, an optical film such as a liquid crystal color filter, a circularly polarized light separating film, stereoscopic glasses, and a polarizing mask can be formed. Further, application to a broadband switchable mirror, an optical writing type recording medium, or the like is also possible. It is also possible to dope a ferroelectric liquid crystal, an antiferroelectric liquid crystal, and a TGB phase. Naturally, it can be used as an ordinary optically active compound, and can be applied to a helical structure inducing agent in an STN element or a TN element.

The liquid crystal composition of the present invention may also contain a non-chiral azo or styrene-based compound which isomerized by light, which further increases the rate of change of the helical pitch during light irradiation. There are things you can do.

Hereinafter, the liquid crystal color filter, the optical film, and the recording medium will be described in detail.

<Liquid Crystal Color Filter> The liquid crystal color filter of the present invention comprises at least the optically active compound of the above general formula (II), and further comprises a liquid crystal compound, preferably a nematic liquid crystal compound, and optionally a light-emitting compound. It comprises a reactive chiral agent, a polymerizable monomer, a photopolymerization initiator, other components listed in the liquid crystal composition of the present invention, a surfactant having an excluded volume effect, and the like.

Hereinafter, the liquid crystal color filter of the present invention will be described in detail through the description of the method of manufacturing the liquid crystal color filter.

The liquid crystal color filter of the present invention can be prepared from a composition containing the above-mentioned liquid crystal composition of the present invention and a chiral agent.

In this case, a sheet form composed of only the liquid crystal composition may be used, or a layer (liquid crystal layer) containing the liquid crystal composition is provided on a desired support or temporary support. An embodiment may be used, and another layer (film) such as an alignment film or a protective film may be further provided. In the latter case,
Two or more liquid crystal layers can be stacked, and in this case, the above-described exposure step described later is provided a plurality of times.

As the liquid crystal compound, photoreactive chiral agent, polymerizable monomer, photopolymerization initiator and other components, the same compounds as those usable in the liquid crystal composition of the present invention can be used. The amount, preferred range, and the like are the same as in the case of the liquid crystal composition. It is preferable to use a surfactant having an excluded volume effect in combination.

The content of the optically active compound represented by the general formula (II) in the liquid crystal composition constituting the liquid crystal color filter is the same as that of the liquid crystal composition of the present invention described above.

The liquid crystal color filter of the present invention can be preferably produced by using, for example, the liquid crystal composition of the present invention.

The method for producing a liquid crystal color filter is not particularly limited. For example, when a photoreactive chiral agent is not contained, blue (B) and green (G) are controlled by controlling the temperature of the liquid crystal phase. ) And red (R). This method can be referred to IDW'99 Abstracts pp. 379-381. or,
When a photoreactive chiral agent is contained, it can be produced by the following method. That is, a manufacturing method including at least one step of imagewise exposing to light with the first light and patterning, and then photopolymerizing and curing by the second light (hereinafter, sometimes referred to as “exposure step”). It may be a method. Further, depending on the manufacturing mode selected, a step of appropriately subjecting the liquid crystal composition to a contact surface with an alignment treatment (alignment treatment step), a step of transferring and forming a liquid crystal layer by adhesion and separation (transfer step), It may be formed through a step of applying and forming a liquid crystal layer (coating step). As a method for producing a liquid crystal color filter, a method including a photoreactive chiral agent in a liquid crystal composition is preferable.

Hereinafter, a specific embodiment will be described as an example of a manufacturing method including the above-described exposure step. -Exposure process-

In the exposure step, both patterning and fixing (polymerization curing) of the liquid crystal compound can be performed by light irradiation. That is, after the photoreactive chiral agent is imagewise exposed and patterned by the first light having a wavelength sensitive to the high sensitivity, the polymerization initiator is photopolymerized by the second light sensitive to the high sensitivity. After curing, the helical structure of the liquid crystal compound is fixed to a desired selective reflection color.

When the liquid crystal composition is irradiated with the first light, the co-existing photoreactive chiral agent responds to the illuminance to change the helical structure of the liquid crystal compound. An image-like pattern is formed showing the reflection color. Therefore, if light irradiation is performed with the irradiation intensity changed for each desired region, a plurality of colors are presented according to the irradiation intensity, for example,
By exposing through an exposure mask formed by changing the light transmittance like an image, it is possible to simultaneously form an image, that is, a colored region having different selective reflection by one light irradiation. Further, a liquid crystal color filter can be manufactured by irradiating a second light and curing (fixing) the second light.

The wavelength of the first light is preferably set in the light-sensitive wavelength region of the photoreactive chiral agent, particularly in the wavelength close to the light-sensitive peak wavelength, in that sufficient patterning sensitivity can be obtained. Also, as the wavelength of the second light,
It is preferable to set the polymerization initiator to a light-sensitive wavelength range, particularly to a wavelength close to the light-sensitive peak wavelength, in that sufficient photopolymerization sensitivity can be obtained.

The illuminance (irradiation intensity) of the first and second lights is not particularly limited, and can be appropriately selected depending on the material used so that sufficient photosensitivity can be obtained during patterning and polymerization curing. . As the light source used for the irradiation of the first and second lights, a light source that emits ultraviolet light is preferable in terms of high energy, structural change of the liquid crystal compound and rapid polymerization reaction, and examples thereof include a high-pressure mercury lamp and a metal halide lamp. , Hg-Xe lamps and the like. Also,
It is preferable to have a light quantity variable function.

More specifically, the manufacturing method according to the following first and second embodiments may be used, and the manufacturing method can be more suitably performed according to these two embodiments. [First Embodiment] (1) A step of providing a liquid crystal composition in a coating liquid state on a temporary support to form a transfer material having at least a liquid crystal layer.

The liquid crystal composition in the form of a coating liquid can be prepared by dissolving and dispersing each component in an appropriate solvent. Here, examples of the solvent include 2-butanone, cyclohexanone, methylene chloride, chloroform and the like.

A cushion layer containing a thermoplastic resin or the like is provided between the liquid crystal layer and the temporary support from the viewpoint of securing adhesion during transfer, for example, when there is a foreign substance or the like on the transfer target. The surface of the cushion layer or the like may be preferably subjected to an orientation treatment (orientation treatment step) such as a rubbing treatment. (2) a step of laminating the transfer material on a light transmissive substrate;

In addition to the light transmitting substrate, an image receiving material having an image receiving layer on a substrate may be used. Further, the liquid crystal composition may be applied directly on the substrate without using the transfer material (application step). Coating can be appropriately selected from known coating methods using a bar coater, a spin coater, or the like. However, the transfer method is preferable in terms of material loss and cost. (3) A step of removing the transfer material from the light-transmitting substrate and forming a liquid crystal layer on the substrate (transfer step).

The liquid crystal layer may be composed of a plurality of layers by further laminating after passing through the following (4). (4) a step of liquid crystal layer to form a pixel pattern illustrating the selective reflection color was irradiated with ultraviolet illuminance [nu ¹ imagewise through an exposure mask, to which further cure the layer by irradiation with ultraviolet illuminance [nu ² (Exposure step). [Second Aspect] (1) A step of providing a liquid crystal composition directly on a support constituting a color filter to form a liquid crystal layer.

Here, the liquid crystal layer can be formed by applying a liquid crystal composition prepared in a coating liquid in the same manner as described above by a known coating method using a bar coater, a spin coater or the like.

Further, between the liquid crystal layer and the temporary support,
An alignment film similar to the above may be formed. The surface of the alignment film or the like is preferably subjected to an alignment treatment (alignment treatment step) such as a rubbing treatment. (2) An exposure step similar to step (4) of the first embodiment.

The thickness of the liquid crystal layer (sheet-like liquid crystal composition) functioning as a liquid crystal color filter is 1.5 to 1.5.
4 μm is preferred.

Further description will be made below with reference to FIGS. 1 to 3 are schematic views showing one embodiment of a process for producing a liquid crystal color filter of the present invention.

First, the above-mentioned components are dissolved in an appropriate solvent to prepare a coating liquid cholesteric liquid crystal composition. Here, each component and solvent are as described above.

As shown in FIG. 1- (A), a support 10 (hereinafter also referred to as a “temporary support”) is prepared, and an acrylic resin, polyester, polyurethane, or the like is formed on the support 10 by coating. Cushion layer (thermoplastic resin layer) 12
And an alignment film 1 made of polyvinyl alcohol or the like.
4 is laminated. A rubbing process is performed on this alignment film as shown in FIG. This rubbing treatment is not always necessary, but the rubbing treatment can further improve the orientation.

Next, as shown in FIG. 1C, a liquid crystal composition in the form of a coating liquid is applied on the alignment film 14 and dried to form a cholesteric liquid crystal layer 16.
A transfer material is prepared by providing a cover film 18 on the top. Hereinafter, the transfer material is referred to as a transfer sheet 20.

On the other hand, as shown in FIG. 1- (D), another support 22 is prepared, an alignment film 24 is formed on the support in the same manner as described above, and the surface is rubbed. Hereinafter, this is referred to as a color filter substrate 26.

Next, after the cover film 18 of the transfer sheet 20 was peeled off, as shown in FIG. 2E, the surface of the liquid crystal layer 16 of the transfer sheet 20 and the alignment film 24 of the color filter substrate 26 were removed. The sheets are overlapped so that they come into contact with the surface, and are laminated through a roll rotating in the direction of the arrow in the figure. Thereafter, as shown in FIG. 1- (F), the transfer sheet 20 is peeled off between the alignment film 14 and the cushion layer 12, and the liquid crystal layer is transferred together with the alignment film 14 on the color filter substrate. In this case, the cushion layer 12
Need not necessarily be peeled off together with the temporary support 10.

After the transfer, as shown in FIG. 3G, an exposure mask 28 having a plurality of regions having different light transmittances is disposed above the alignment film 14, and the first exposure mask 28 is provided through the mask 28. Light is applied to the liquid crystal layer 16 in a pattern. The liquid crystal layer 16 contains a liquid crystal compound, a chiral compound, or the like so that the helical pitch varies depending on the amount of light irradiation, and a structure having a different helical pitch is provided for each pattern, for example, green (G).
Are reflected, blue (B) and red (R) are transmitted, blue (B) is reflected, green (G) and red (R) are transmitted, red (R) is reflected, and green ( G) and blue (B).

Next, as shown in FIG. 3H, the liquid crystal layer 16 is further irradiated with ultraviolet rays at an irradiation intensity different from the light irradiation in the step (G) to fix the pattern. Then, using 2-butanone, chloroform and the like,
By removing unnecessary portions on the liquid crystal layer 16 (for example, remaining portions such as a cushion layer and an intermediate layer, and unexposed portions), FIG.
As shown in (I), a liquid crystal layer having a BGR reflection region can be formed.

The method shown in FIGS. 1 to 3 is an embodiment of a method for manufacturing a color filter by a lamination method, but may be a method by a coating method in which a liquid crystal layer is directly formed on a substrate for a color filter. . In this case, when applied to the above embodiment, a liquid crystal layer is applied on the alignment film 24 of the color filter substrate 26 shown in FIG. 1- (D), dried, and then similar to FIGS. 3- (G) to (I). Are sequentially performed.

These steps and materials to be used, such as a transfer material and a support, are described in Japanese Patent Application Nos. 11-342896 and 11-343665 filed by the present inventors.
The details are described in each specification of the item.

As described above, when the liquid crystal composition containing the optically active compound represented by the general formula (II) is used, since the twisting power of the helical structure of the liquid crystal is large, blue (B) having excellent color purity, Green
A liquid crystal color filter consisting of three primary colors (G) and red (R) can be obtained.

<Optical Film> The optical film of the present invention comprises the optically active compound represented by the general formula (II) of the present invention, a liquid crystal compound, and if necessary, a photoreactive chiral agent. And other components enumerated in the liquid crystal composition of the present invention, such as a polymerizable monomer, a photopolymerization initiator, and a surfactant that exerts an excluded volume effect. It can be manufactured by irradiating light with a light amount.

The optical film of the present invention is prepared by appropriately selecting from the above-mentioned liquid crystal composition of the present invention and a known composition containing the optically active compound represented by the general formula (II). can do. Here, the form of the optical film is not particularly limited, and is a sheet form composed only of the liquid crystal composition, a form in which a layer (liquid crystal layer) containing the liquid crystal composition is provided on a desired support or temporary support. And other layers (films) such as an alignment film and a protective film.
May be provided.

As the liquid crystal compound, photoreactive chiral agent, polymerizable monomer, photopolymerization initiator and other components, the same compounds as those usable in the liquid crystal composition of the present invention can be used. The amount, preferred range, and the like are the same as in the case of the liquid crystal composition. Further, the content of the optically active compound represented by the general formula (II) in the liquid crystal composition constituting the optical film is also the same as that of the liquid crystal composition of the present invention described above.

The optical film of the present invention can be suitably produced by using, for example, the liquid crystal composition of the present invention.

Further, as a method for producing an optical film, it can be produced by a method substantially similar to that for the liquid crystal color filter, and may be a method comprising at least one exposure step. Further, depending on the manufacturing mode to be selected, it may be formed through steps such as the alignment treatment step, the transfer step, and the coating step.

More specifically, it can be manufactured in substantially the same manner as the manufacturing method of the first and second embodiments.

As described above, when the liquid crystal composition containing the optically active compound represented by the general formula (II) is used, since the twisting power of the helical structure of the liquid crystal is large, the color width of selective reflection of the liquid crystal is widened. An optical film having various selective reflection colors, an optical film of primary colors (B, G, R) having excellent color purity can be obtained.

<Recording Medium> The recording medium of the present invention comprises the optically active compound represented by the above general formula (II), and further comprises a liquid crystal compound, preferably a nematic liquid crystal compound, and if necessary, an optically active compound. Reactive chiral agent, polymerizable monomer,
The liquid crystal composition of the present invention includes other components such as a photopolymerization initiator and a surfactant that exerts an excluded volume effect.

The recording medium of the present invention is not limited in its form, and may be in the form of a sheet composed of only a liquid crystal composition, or a desired support or temporary support (hereinafter referred to as a “support or the like”). ) May be provided with a layer (liquid crystal layer) containing a liquid crystal composition containing a chiral agent.
Here, the liquid crystal composition can be appropriately selected from the above-described liquid crystal composition of the present invention and a known composition containing the compound represented by the general formula (II). Further, another layer (film) such as an alignment film or a protective film may be provided.

As the liquid crystal compound, photoreactive chiral agent, polymerizable monomer and photopolymerization initiator, and other components, the same compounds as those usable in the liquid crystal composition can be used. The preferable range and the like are the same as those of the liquid crystal composition. Further, the content of the optically active compound represented by the general formula (II) in the liquid crystal composition constituting the recording medium is the same as that of the liquid crystal composition of the present invention described above.

The recording medium of the present invention can be suitably prepared, for example, by providing the above-described liquid crystal composition of the present invention on a support or the like.

The method for providing the liquid crystal composition on a support or the like is as follows. (1) A transfer material in which a liquid crystal layer containing the liquid crystal composition of the present invention is provided on a temporary support is used. A method of transferring a liquid crystal layer, (2) a method of directly applying a liquid crystal composition prepared in a coating liquid state on a support, and the like are exemplified.

In the methods (1) and (2), the transfer material and the coating method are the same as those of the liquid crystal composition of the present invention (first and second embodiments) and FIGS. Can be adapted according to the description.

The recording medium of the present invention produced as described above is irradiated with light in a desired pattern and / or light amount appropriately selected, so that the recording medium has a selective reflection color determined by the twisting force of the liquid crystal. An image can be formed.
Moreover, when the optically active compound represented by the general formula (II) is used as the chiral agent, the helix width of the liquid crystal helical structure is large, so that the hue width at which the liquid crystal selectively reflects can be expanded, and the color purity can be increased. , A multicolor image with high image quality can be formed.

Also, for example, by using a polymerizable liquid crystal compound or a polymerizable monomer, the liquid crystal after patterning can be fixed, and an image having sufficient image stability can be formed.

As a light source for irradiating light, the same light source as that usable in the liquid crystal color filter of the present invention can be suitably used for optical recording. Also,
The same applies to the case of light irradiation for fixing the liquid crystal.

As described above, the use of the optically active compound represented by the general formula (II) as a chiral agent for inducing the helical structure of liquid crystal molecules increases the twisting power (twist angle) of the liquid crystal. Since it can change, the selective reflection wavelength range of the cholesteric liquid crystal is expanded, and as a result, the color purity of the three primary colors of BGR can be further increased. Therefore, the hue selectivity and vividness of the liquid crystal are improved, and in particular, in a liquid crystal color filter or an optical film, a clear and vivid color image can be displayed.
In a recording medium, the hue of an image to be formed can be diversified.

[0141]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. still,
“Parts” and “%” in the examples all represent “parts by mass” and “% by mass”.

First, a synthesis example of the optically active compound of the present invention represented by the general formula (II) will be described. The numbers in parentheses of the optically active compounds indicate the exemplary numbers of the optically active compounds exemplified in the above [Formula 15] to [Formula 17]. <Synthesis of Optically Active Compound (1-1)> (R) -6,6 ′
4 g of dibromo-1,1'-bi-2-naphthol (9 m
mol), 2.5 ml of triethylamine (18 mmo
l) and 20 ml of THF, and 1.4 ml (9.9 mmol) of phthalic dichloride in 10 ml of THF.
The solution was added dropwise. After stirring at room temperature for 30 minutes, the mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. Ethyl acetate is distilled off,
The residue was purified by column chromatography. 2.75 g (4.8 mmol) of compound (1-1) was obtained.
The yield was 53%. The results (data) of identifying the pale yellow powdery crystals obtained above are shown below. [α] _D ²⁵ -393 ° (c 0.10, CHCl ₃ ). ¹ H-NMR (CDCl ₃ ): δ (in ppm from tetrame)
thylsilane) 8.21-8.13 (2H, m), 8.0
3-7.85 (3H, m), 7.75-7.55 (3
H, m), 7.53-7.32 (4H, m), 7.19.
−7.10 (1H, m), 7.02-7.97 (1H,
m)

<Synthesis of Optically Active Compound (2-1)>
(R) -6,6'-Dibromo-1,1'-bi-2-naphthol was changed to (R) -1,1'-bi-2-naphthol except that the above optically active compound (1- Compound (2-1) was obtained in the same manner as in the synthesis of 1). The yield was 37%. [α] _D ²⁵ -515 ° (c 0.10, CHCl ₃ ). ¹ H-NMR (CDCl ₃ ): δ (TMS) 8.10
−7.93 (5H, m), 7.73-7.20 (10
H, m), 7.05-6.98 (1H, m)

<Synthesis of Optically Active Compound (2-2)>
1 g of 2'-biphenyldicarboxylic acid (4.1 mmol
l), 1 ml (12 mmol) of oxalyl chloride was added to a mixture of 10 ml of THF and a trace amount of DMF. After stirring at room temperature for 2 hours, the solvent was distilled off. The residue was (R) -1,
1.1 g of 1'-bi-2-naphthol (3.8 mmol
l), 2.5 ml (16 mmol) of triethylamine and 10 ml of THF. After stirring at room temperature for 30 minutes, the mixture was poured into diluted hydrochloric acid and extracted with chloroform.
After the chloroform layer was washed with a 5% aqueous potassium hydroxide solution, it was dried over magnesium sulfate, and chloroform was distilled off. Ethyl acetate was added to the residue, and the solid was separated by filtration to obtain 0.9 g (1.8 mmol) of compound (2-2).
The yield was 48%. [α] _D ²⁵ 94 ° (c 0.10, CHCl ₃ ). ¹ H-NMR (CDCl ₃ ): δ (TMS) 7.95
-7.85 (4H, m), 7.70 (2H, d), 7.
57 (3H, dd), 7.47-7.28 (8H,
m), 7.20 (2H, dd), 7.00 (2H, d)

<Synthesis of Optically Active Compound (2-3)>
Compound (2-3) was prepared in the same manner as in the synthesis of optically active compound (2-2), except that 2'-biphenyldicarboxylic acid was changed to trans-1,2-cyclohexanedicarboxylic acid.
I got The yield was 13%. [α] _D ²⁵ -94 ° (c 0.10, CHCl ₃ ). ¹ H-NMR (CDCl ₃ ): δ (TMS) 8.02
(2H, m), 7.92 (2H, d), 7.53 (2
H, d), 7.45 (2H, dd), 7.24 (2H,
dd), 7.02 (2H, d), 2.86-7.70.
(2H, m), 2.10-1.07 (8H, m)

(Example 1-1): Measurement of Helical Pitch 0.25 part of the chiral agent (exemplified compound 1-1) of the present invention synthesized by a method similar to the above-mentioned synthesis method was used in a cholesteric liquid crystal composition (ZLI- 1132, manufactured by Merck) 9
The mixture was mixed with 9.75 parts and injected into a wedge-type cell (glass thickness: 1.1 mm, blue plate) that had been subjected to a uniaxial alignment treatment with a polyimide alignment film. Here, when the helical pitch at room temperature was measured using a polarizing microscope, it was 5.0 μm. This is 80 μm ⁻¹ when converted to helical twisting power (HTP). When the direction of the twist was confirmed by the contact method, it was found that the twist was left.

(Example 1-2): Measurement of Helical Pitch 0.25 parts of the chiral agent (exemplified compound 2-1) of the present invention synthesized by a method similar to the above-mentioned synthesis method was used in a cholesteric liquid crystal composition (ZLI- 1132, manufactured by Merck) 9
The mixture was mixed with 9.75 parts and injected into a wedge-type cell (glass thickness: 1.1 mm, blue plate) that had been subjected to a uniaxial alignment treatment with a polyimide alignment film. Here, when the helical pitch at room temperature was measured using a polarizing microscope, it was 3.6 μm. This is 110 μm ⁻¹ when converted to helical twisting power (HTP). By the contact method,
When the direction of the twist was confirmed, the twist was left.

Example 2 Production of Broadband Circularly Polarized Reflector (1) Preparation of Substrate A polyimide alignment film (LX-1400,
After applying a coating solution by a spin coater and drying in an oven at 100 ° C. for 5 minutes,
The alignment film was formed by firing in an oven at 250 ° C. for 1 hour. Further, the surface of the film was subjected to an orientation treatment by a rubbing treatment to produce a glass substrate with an orientation film.

(2) Production A coating solution prepared according to the following formulation was applied on the alignment film of the glass substrate provided with the alignment film obtained above using a bar coater.
After being kept on a hot plate at 110 ° C. for 5 minutes, light irradiation was performed for 3 minutes with a super-high pressure mercury lamp at this temperature through a band-pass filter having a light source center wavelength of 365 nm.

Next, the sample was kept at 110 ° C. in a dark place for 5 minutes, then the bandpass filter was removed, and the whole surface was further irradiated with an irradiation energy of 500 mJ / cm ² by the same ultra-high pressure mercury lamp while blowing nitrogen gas. It was exposed and polymerized and cured. As described above, a circularly polarized light reflecting plate was produced.

[0151]

Embedded image

The circularly-polarized light reflecting plates obtained above were 470 to 7
It exhibited selective reflection in a wide wavelength range over 00 nm, and had sufficient band characteristics as a broadband circularly polarized light reflecting plate. In addition, the left circularly polarized light reflectance at a selective reflection wavelength of 550 nm was 95%.

Example 3 Preparation of Liquid Crystal Color Filter (1) Preparation of Filter Substrate

A polyimide alignment film (LX-
1400, manufactured by Hitachi Chemical DuPont Co., Ltd.) was applied by a spin coater, dried in a 100 ° C. oven for 5 minutes, and baked in a 250 ° C. oven for 1 hour to form an alignment film. Further, the surface of the film was subjected to an orientation treatment by a rubbing treatment to produce a glass substrate with an orientation film. (2) Formation of filter layer

On the alignment film of the glass substrate provided with the alignment film obtained above, a coating solution for a photosensitive resin layer prepared according to the following formulation was applied by a spin coater, and dried in an oven at 100 ° C. for 2 minutes. Thus, a photosensitive resin layer was formed.

[0156]

Embedded image

Then, the photosensitive resin layer was held on a hot plate at 100 ° C. for 5 minutes so as to be in contact with the surface of the glass substrate, so that the photosensitive resin layer was colored. Further, on the photosensitive resin layer, the transmittance is different in three stages (0%, 46%, 92%), and the respective regions are arranged corresponding to blue pixels, green pixels, and red pixels. An ultra-high pressure mercury lamp was arranged via a photomask and a band-pass filter having a center at 365 nm, and irradiation was performed with the ultra-high pressure mercury lamp through the photomask and the band-pass filter to perform patterning. The irradiation energy at this time was 300 mJ / for the red pixel.
cm ² , and the irradiation intensity was 30 mW / cm ² .

Next, the photomask and the band-pass filter were removed, and the irradiation energy was 500 mJ / cm by using the same ultra-high pressure mercury lamp while blowing nitrogen gas.
^The whole surface was further exposed by 2 and polymerized and cured. Further, in order to promote the degree of curing of the filter portion (photosensitive resin layer), 22
Baking was performed in an oven at 0 ° C. for 20 minutes to obtain a color filter on which a red pixel, a green pixel, and a blue pixel pattern were formed.

At the time of the above patterning, the helical pitch of the liquid crystal (the torsional force of the liquid crystal) can be greatly changed by irradiation, and a pixel pattern composed of red, green and blue with high color purity could be formed.

(Example 4): Preparation of optical compensation film for STN element

A polyethylene vinyl alcohol (PVA) film having a saponification degree of 99.5% was formed on triacetyl cellulose (TAC) having a thickness of 80 μm by a bar coating method, and heated at 110 ° C. for 3 minutes. A rubbing treatment was performed on the PVA film, and a coating solution prepared according to the following formulation was further heated and applied by a bar coater, and dried in an oven at 120 ° C. for 3 minutes to form a film.

[0162]

Embedded image

Next, at a temperature of 100 ° C., ultraviolet light was irradiated from above the film using a high-pressure mercury lamp (irradiation energy: 3).
00mJ / cm ² ) to polymerize and cure the film.
An optical compensation film for an element was manufactured (hereinafter referred to as “STN compensation film”).
Called. ). When the film thickness of the STN compensation film at this time was measured, it was 5.0 μm. Further, from the polarization transmission spectrum profile of the STN compensation film, it was found that the orientation (spiral structure) of the liquid crystal molecules was twisted in the film thickness direction at 240 degrees, and the twist angle (rotation angle) of the spiral was 240 degrees.

Also, an STN compensation film having a twist angle (-240 degrees) opposite to that of this film is prepared, and these films are superimposed so that the liquid crystal molecules of the matched portions are orthogonal to each other.
Inserted between two polarizing plates whose absorption axes are orthogonal to each other,
When observed visually, a good black color was shown. Therefore, the film formed as described above (STN compensation film)
It was confirmed that the film acted as an optical compensation film for an N element.

(Embodiment 5): Prevention of generation of reverse twist domain for TN element

A polyimide alignment film (LX-1400, manufactured by Hitachi Chemical DuPont) was applied on the ITO film of the glass substrate with the ITO film by a spin coater.
After drying in an oven at 100 ° C. for 5 minutes, it was baked in an oven at 250 ° C. for 1 hour to form an alignment film. Further, a rubbing treatment was performed on the surface of the film to perform an orientation treatment so that the rubbing angle was 90 degrees, thereby producing two glass substrates with an orientation film.

The glass substrates provided with the above-mentioned alignment films are arranged so that the alignment films face each other, and bonded together by a two-liquid epoxy resin adhesive mixed with spacer beads having a diameter of 6 μm.
A driving cell was formed. When the thickness of the cell was measured by an optical interference method, it was 5.4 μm.

A composition having the following composition was injected into the cell. [Composition] Cholesteric liquid crystal composition (ZLI-1132, manufactured by Merck) 99.9% Chiral agent of the present invention (Exemplified compound 2-3 described above) 1%

Next, when the driving cell after injection was inserted between two polarizing plates whose absorption axes were orthogonal to each other and observed visually, no generation of a reverse twist domain was observed. Therefore, there is no reduction in contrast due to the occurrence of reverse twist, and an image display excellent in contrast and color purity can be expected.

[0170]

The optically active compound of the present invention has a large twisting power (torsion angle) of liquid crystal and can be applied as an excellent chiral agent, and can also be used as a general optically active compound.

In the liquid crystal composition of the present invention, since the above-mentioned optically active compound is used, a large amount of HT can be obtained with a small amount of addition depending on the purpose or application of the liquid crystal composition.
P can be obtained.

Since the chiral agent of the present invention has a very slow photoreaction, desired performance can be satisfied when used in combination with a photoreactive chiral agent. Therefore, the present invention can be applied to a wide range of uses such as a liquid crystal color filter, a circularly polarized light separating film, stereoscopic glasses, an optical film such as a deflection mask, and a recording medium.

Further, since the liquid crystal color filter of the present invention uses the optically active compound as described above, the liquid crystal comprising the three primary colors of blue (B), green (G), and red (R) having excellent color purity. It can be a color filter.

Further, also in the optical film and the recording medium, by using the optically active compound as described above,
By appropriately selecting a liquid crystal compound or the like, an optical film or a recording medium having various characteristics can be obtained.

[Brief description of the drawings]

FIG. 1 is a schematic view showing a part of a process of manufacturing a liquid crystal color filter of the present invention.

FIG. 2 is a schematic view showing a part of a process for manufacturing a liquid crystal color filter of the present invention.

FIG. 3 is a schematic view showing a part of a step of manufacturing a liquid crystal color filter of the present invention.

[Explanation of symbols]

 Reference Signs List 10 support (temporary support) 12 cushion layer (thermoplastic resin layer) 14, 24 alignment film 16 liquid crystal layer (liquid crystal composition) 18 cover film 20 transfer sheet 22 substrate 26 color filter substrate 28 exposure mask

──────────────────────────────────────────────────の Continued on the front page (51) Int.Cl. ⁷ Identification FI FI Theme Court ゛ (Reference) G02F 1/13 500 G02F 1/13 500 // C07M 9:00 C07M 9:00 (72) Inventor Mitsuyoshi Ichihashi 200, Onakazato, Fujinomiya-shi, Shizuoka Prefecture Fuji Photo Film F-term (reference) 2H048 AA06 AA12 BA04 BA43 BA47 BA48 BA64 BB02 BB42 2H049 BA05 BA06 BA43 BC05 BC08 BC22 4C022 MA02 4H027 BA01 BD14 DH01 DH03 DH04 DH05

Claims (8)

[Claims] 1. An optically active compound represented by the following general formula (I). Embedded image [Wherein, R ¹ represents a halogen atom, an aryl group, an alkynyl group, a formyl group, —CH ＝ CH—R ² , —C (R ³ ) =
CH ₂ , —CH ＝ C (R ⁴ ) ₂ , where R ² and R ³
Represents an aryl group, and R ⁴ represents an alkoxycarbonyl group, an aryloxycarbonyl group, or a cyano group. L ¹ represents an alkylene group, alkenylene group, or arylene group. The binaphthyl moiety has either (R) or (S) axial asymmetry. ] 2. A liquid crystal chiral agent comprising an optically active compound represented by the following general formula (II). Embedded image Wherein R ⁵ is a hydrogen atom, a halogen atom, an aryl group, an alkynyl group, a formyl group, —CH ＝ CH—R ⁶ ,
—C (R ⁷ ) ＝ CH ₂ , —CH ＝ C (R ⁸ ) ₂ , wherein R ⁶ and R ⁷ represent an aryl group, and R ⁸ represents an alkoxycarbonyl group, an aryloxycarbonyl group, or a cyano group. Represent. L ² represents an alkylene group, alkenylene group, or arylene group. The binaphthyl moiety has either (R) or (S) axial asymmetry. ] 3. A liquid crystal composition comprising at least a liquid crystal compound and at least one chiral agent according to claim 2. 4. A liquid crystal composition comprising a liquid crystal compound having at least one polymerizable functional site, a photopolymerization initiator and at least one chiral agent according to claim 2. 5. A liquid crystal composition comprising a liquid crystalline compound having at least one ethylenic double bond capable of undergoing addition polymerization, a photopolymerization initiator and at least one chiral agent according to claim 2. 6. A liquid crystal color filter containing at least a liquid crystalline compound and the chiral agent according to claim 2. 7. An optical film containing at least a liquid crystalline compound and the chiral agent according to claim 2. 8. A recording medium containing at least a liquid crystalline compound and the chiral agent according to claim 2.