JP2002179681A - Optically active compound, photoreactive chiral agent, liquid crystal composition, liquid crystal color filter, optical film and recording medium, method for changing helical structure of liquid crystal and method for fixing helical structure of liquid crystal - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an optically active compound (a photoreactive chiral agent) having photosensitivity and capable of greatly changing the helical pitch (twisting power) of a liquid crystal with light. SOLUTION: This optically active compound is represented by formula (1) or (2) [wherein, R1 and R2 are each hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group or cyano group; L1 to L3 are each a halogen atom, an alkyl group, an alkoxy group, cyano group or nitro group; (l) and (m) are each 0-2; and (n) is 0-3].

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an optically active compound having photosensitivity, a photoreactive chiral agent for causing a change in the structure of a liquid crystal, a liquid crystal composition containing the same, an optical film, a liquid crystal color filter and a recording medium, Also, the present invention relates to a method for changing or fixing a helical structure of a liquid crystal.

[0002]

2. Description of the Related Art In recent years, liquid crystal materials have attracted attention. For example, cholesteric liquid crystal compounds having a helical structure and exhibiting a variety of selective reflection colors due to the twisting force (twist angle) of the helical structure have been developed. Because of its excellent color purity of reflected light, it is widely used for optical films, liquid crystal color filters, recording media, and the like. As a specific example, a color filter will be described below as an example.

For example, a color filter used in 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 has been
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 and photolithography. In general, a color filter pixel is formed by patterning by a method, or a colored pixel is directly printed on a substrate.

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. As described above, as a process for manufacturing a color filter, there has been a demand for a manufacturing method capable of easily and easily manufacturing a high-quality color filter with little material loss.

On the other hand, the performance of a color filter is required to be high in transmittance and color purity. In recent years, the method using a dye has optimized the type of dye and the dyeing resin. The use of finely dispersed pigments has improved the above requirements. However, in recent liquid crystal display (LCD) panels, the requirements for the transmittance and color purity of color filters are extremely high. Particularly, in color filters for reflective LCDs, white display of paper white, contrast, and color reproducibility are both compatible. Is difficult, but in the conventional manufacturing method,
Color filters manufactured by dyeing a dye in a resin or dispersing a pigment are all light-absorbing color filters, so the improvement in color purity by further improving transmittance is almost at its limit. Had reached.

In view of the above situation, a polarization type color filter having a cholesteric liquid crystal as a main component is known. This polarization-based color filter reflects a certain amount of light and transmits the rest to display an image, so it has high light use efficiency and is superior to the light absorption type color filter in terms of transmittance and color purity. It has the performance which it did. On the other hand, in the manufacturing method, from the viewpoint of obtaining a uniform thickness, a method of forming a film on a substrate by using a spin coating method or the like has been generally performed. Was disadvantageous.

A photoreactive chiral compound (chiral compound) has been proposed as a means for solving the above problems, ensuring uniformity of the color purity and the like of the color filter film, and realizing a reduction in the number of manufacturing steps. Is 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 according to the intensity of the irradiation energy, and Since the helical pitch (helical twist angle) changes, the principle is used that a selective reflection color is formed for each pixel only by pattern exposure with 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 immobilizing the patterned cholesteric liquid crystal compound after patterning by imagewise light irradiation. This can be applied to optical films, image recording, and the like.

In particular, when a color filter is produced by a single mask exposure, B (blue), G (green),
It is desired that three primary colors (red) can be formed with high color purity by one exposure. However, when the rate of change of the twist of the liquid crystal is small, sufficient color purity cannot be obtained. Therefore, from the viewpoint of displaying three primary colors having high color purity in one exposure, practically, as a photoreactive chiral compound to be used, the twisting force of the helical structure of the liquid crystal compound can be greatly changed. It is necessary to use a chiral compound (chiral agent) having a large value. That is, by using a chiral compound having a large twist change rate, the width of the hue selectively reflected by the change in the amount of light can be widened.

Japanese Patent Application Laid-Open No. H11-248943 discloses that a polymerizable mesogen compound having an isosorbide skeleton in a chiral mother nucleus is used as a chiral compound constituting a broadband reflective polarizing plate. This polymerizable mesogen compound can change the helical structure of the liquid crystal by acting on the liquid crystal compound. However, the reflection wavelength band of the polarizing plate described in the publication, that is, the helical structure of the liquid crystal (helical twisting force).
Is changed so as to exhibit a desired selective reflection, the change is adjusted by the mesogen compound and the achiral compound (liquid crystal).
The amount of light and the amount of light are not involved at all. That is, the publication does not suggest that the helical structure of the liquid crystal (helical twisting force) is changed by a change in the amount of light, and the compounds exemplified in the publication are useful in terms of the rate of change of the twisting force with respect to light. No suggestion is made.

[0010]

As described above, the present invention has a photoreactivity capable of changing the alignment structure such as the helical pitch (twisting force and helical twist angle) of the liquid crystal depending on the amount of light to be irradiated. In the case of a cholesteric liquid crystal phase containing a compound, the wavelength range in which selective reflection is possible is wide, and various selective reflections are exhibited. In particular, it is possible to display the three primary colors (B, G, R) with high color purity, and the spiral. At present, a photoreactive chiral agent capable of greatly changing the pitch (twisting force) has not yet been provided.

An object of the present invention is to solve the above conventional problems and achieve the following objects. That is, an object of the present invention is, first, to provide a novel optically active compound which has photosensitivity and can undergo structural change by isomerization by light. Second, the orientation of the liquid crystal compound can be controlled, and the rate of change in the helical pitch (twisting force) of the liquid crystal due to light (hereinafter, sometimes referred to as the “twist change rate”) is large. In this case, the three primary colors (B, G,
It is an object of the present invention to provide a photoreactive chiral agent capable of performing selective reflection in a wide range including R) and displaying three primary colors having high color purity. Third, optical properties include a photoreactive chiral agent that can change the helical pitch (twisting force) of the liquid crystal by light and has a large rate of change in twist, and greatly controls the orientation state of liquid crystal molecules by light. In the case of a cholesteric liquid crystal, for example, in the case of a cholesteric liquid crystal, a wide range of selective reflection colors including three primary colors can be exhibited by light irradiation, and a liquid crystal composition capable of displaying three primary colors with excellent color purity is provided. The purpose is to.

Fourth, the present invention provides a liquid crystal composition comprising a photoreactive chiral agent having a large twist change rate, which is irradiated with light to greatly change the helical pitch (twist force) of the liquid crystal. It is an object to provide a method for changing the structure. Fifth, a liquid crystal composition containing a photoreactive chiral agent having a large twist change rate can be immobilized in a state in which a patterned helical pitch is maintained without loss after being imagewise exposed, and in particular, a liquid crystal phase can be obtained. In the case of a cholesteric liquid crystal phase, an object of the present invention is to provide a method for fixing a helical structure of a liquid crystal, which can fix a helical structure of a liquid crystal to a desired selective reflection color and obtain a hue with high color purity. I do.

A sixth object of the present invention is to provide a liquid crystal color filter having a high color purity, which contains a photoreactive chiral agent capable of greatly changing the helical pitch (twisting force) of the liquid crystal by light irradiation. I do. Seventh, a non-light-absorbing optical film containing a photoreactive chiral agent that can significantly change the twisting force of the liquid crystal by light irradiation, for example, in the case of a cholesteric liquid crystal phase, the selective reflection area is wide and the color purity is high. It is intended to provide an optical film. Eighth, a recording medium that contains a photoreactive chiral agent that can greatly change the twisting force of liquid crystal by light irradiation and that can form a clear image by changing the amount of light in an image-like manner, such as a cholesteric liquid crystal phase In the case of (1), an object is to provide a recording medium capable of forming an image composed of a selective reflection color having a wide hue and a high color purity.

[0014]

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

Embedded image

[In the general formula (1), R ¹ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl Group,
Represents an acyloxy group or a cyano group, and L ¹ and L ² are each independently a halogen atom, an alkyl group, an alkoxy group,
Represents a cyano group or a nitro group. l and m each independently represent 0, 1, and 2. ]

<2> An optically active compound represented by the following general formula (2).

Embedded image

[In the general formula (2), R ² represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl Group,
L ³ represents a halogen atom, an alkyl group, an alkoxy group, a cyano group, or a nitro group; n represents 0, 1, 2, and 3. ]

<3> A photoreactive chiral agent comprising the optically active compound described in <1> or <2>. Also,
The helical pitch of the liquid crystal can be changed by light irradiation. <4> A liquid crystal composition containing at least a liquid crystal compound and at least one selected from the optically active compounds described in <1> and <2>.

<5> A liquid crystal composition comprising a liquid crystal compound having at least one polymerizable group, at least one selected from the optically active compounds described in <1> and <2>, and a photopolymerization initiator. Things. <6> The liquid crystal composition according to <5>, wherein the optically active compound and the photopolymerization initiator according to <1> or <2> have different photosensitive wavelength ranges.

<7> The liquid crystal composition according to any one of <4> to <6> is irradiated with light to change the structure of the optically active compound represented by the general formula (1) or (2). ,
This is a method of changing the helical structure of the liquid crystal. <8> The liquid crystal composition according to any one of the above <4> to <6> is imagewise exposed to light in the photosensitive wavelength region of the optically active compound represented by the general formula (1) or (2). After irradiation
This is a method for fixing a helical structure of a liquid crystal, comprising a step of performing photopolymerization by irradiating light in a photosensitive wavelength region of a photopolymerization initiator.

<9> A liquid crystal color filter including at least a liquid crystal compound and at least one selected from the optically active compounds described in <1> and <2>. <10> An optical film including at least a liquid crystal compound and at least one selected from the optically active compounds described in <1> and <2>. <11> A recording medium including at least a liquid crystal compound and at least one selected from the optically active compounds described in <1> and <2>.

[0022]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in order. <Optically Active Compound> The optically active compound of the present invention is an isosorbide derivative represented by the following general formula (1) or (2). The compound itself undergoes trans-cis isomerization by light and undergoes a structural change. First, the compound represented by the following general formula (1) will be described.

[0023]

Embedded image

In the general formula (1), R ¹ is a hydrogen atom,
Halogen atom, alkyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, alkoxy group, acyl group,
Represents an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, or a cyano group.

As the halogen atom, a fluorine atom,
A chlorine atom is preferred, and a fluorine atom is particularly preferred.

The alkyl group may be unsubstituted or substituted with a substituent, and is preferably an alkyl group having 1 to 30 carbon atoms, and particularly preferably an alkyl group having 1 to 20 carbon atoms. Examples of the substituent when substituted 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,
A cyano group is preferred, and among them, a halogen atom, an alkoxy group and an acyloxy group are particularly preferred.

Specific examples of the alkyl group include a methyl group, a pentyl group, a cyclohexyl group, a trifluoromethyl group, a benzyl group, an allyl group, a methoxyethyl group and an acetyloxymethyl group.

The aryl group and the heterocyclic group may be unsubstituted or substituted with a substituent, and have 4 to 4 carbon atoms in total.
An aryl group or a heterocyclic group having 0 carbon atoms is preferable,
An aryl group and a heterocyclic group of 0 are particularly preferred. As the substituent when substituted, for example, 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 are preferable. Particularly preferred are a halogen atom, an alkyl group, an alkenyl group, an alkoxy group and an acyloxy group.

Specific examples of the aryl group include phenyl, β-naphthyl, 4-methylphenyl, 4-vinylphenyl, 4-butyloxyphenyl, 4-benzoyloxyphenyl, pyrimidine-2-yl. And an yl group. Further, specific examples of the heterocyclic group include:
For example, a pyridine ring, a pyrimidine ring, a furan ring, a benzofuran ring and the like are preferable, and a pyridine ring and a pyrimidine ring are particularly preferable.

The alkenyl group may be unsubstituted or substituted with a substituent, and is preferably an alkenyl group having 2 to 30 carbon atoms, particularly preferably an alkenyl group having 2 to 20 carbon atoms. As the substituent in the case of being substituted, for example, a halogen atom, an aryl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group are preferable. And acyloxy groups are preferred. Specific examples of the alkenyl group include a vinyl group, a phenylethenyl group, a 4-pentyloxyphenylethenyl group, and a methoxyvinyl group.

The alkynyl group may be unsubstituted or substituted with a substituent, and is preferably an alkynyl group having 2 to 30 carbon atoms, and particularly preferably an alkynyl group having 2 to 20 carbon atoms. As the substituent when substituted, for example, a halogen atom, an aryl group, an alkenyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group are preferable. Acyloxy groups are preferred. Specific examples of the alkynyl group include an ethynyl group, a phenylethynyl group, and a 4-acetyloxyphenylethynyl group.

The alkoxy group may be unsubstituted or substituted with a substituent, and is preferably an alkoxy group having 1 to 30 carbon atoms, particularly preferably an alkoxy group having 1 to 20 carbon atoms. As the substituent when substituted, for example, 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, and a cyano group are preferable. Preferred are a halogen atom, an aryl group, an alkoxy group and an acyloxy group. Specific examples of the alkoxy group include a methoxy group, a butyloxy group, a benzyloxy group, a methoxyethoxyethoxy group, an acetyloxyhexyloxy group, and a benzoyloxidedecyloxy group.

The acyl group (RCO-) may be unsubstituted or substituted with a substituent, and has 2 to 4 carbon atoms in total.
An acyl group of 0 is preferable, and an acyl group having a total of 2 to 30 carbon atoms is particularly preferable. R may be a heterocyclic ring and may include a carbon-carbon double bond or a carbon-carbon triple bond.
When substituted, the substituent is preferably, for example, a halogen atom, an alkoxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, or a cyano group, particularly preferably a halogen atom, an alkoxy group, or an acyloxy group. Specific examples of the acyl group include an acetyl group, a benzoyl group, a cinnamoyl group, a trifluoroacetyl group, a methoxyacetyl group, and a 5-cyclohexylcarbonyloxyhexanoyl group.

The alkoxycarbonyl group may be unsubstituted or substituted with a substituent and has a total carbon number of 2 to 2.
30 alkoxycarbonyl groups are preferred and the total number of carbon atoms is 2
~ 20 alkoxycarbonyl groups are particularly preferred. As the substituent when substituted, for example, 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 are preferable. Groups, alkoxy groups and acyloxy groups are particularly preferred. Specific examples of the alkoxycarbonyl group include a methoxycarbonyl group, a decyloxycarbonyl group, a trifluoroethoxycarbonyl group, a methoxyethoxycarbonyl group, and an acetyloxyethoxycarbonyl group.

The aryloxycarbonyl group may be unsubstituted or substituted with a substituent, and is preferably an aryloxycarbonyl group having 5 to 40 carbon atoms.
An aryloxycarbonyl group having a total of 5 to 30 carbon atoms is particularly preferred, and the aryl moiety may be a heterocyclic ring.
As the substituent when substituted, for example, 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 are preferable. Preferred are a halogen atom, an alkyl group, an alkoxy group, an aryloxycarbonyl group, an acyloxy group, and a cyano group.

Specific examples of the aryloxycarbonyl group include a phenoxycarbonyl group, a biphenyloxycarbonyl group, a β-naphthyloxycarbonyl group,
Phenoxycarbonyl phenoxycarbonyl group, methoxyphenoxycarbonyl group and the like.

The acyloxy group may be unsubstituted or substituted with a substituent, and is preferably an acyloxy group having 2 to 40 carbon atoms, particularly preferably an acyloxy group having 2 to 30 carbon atoms. It may contain a carbon-carbon double bond or a carbon-carbon triple bond. Examples of the substituent when it is substituted include, for example,
A halogen atom, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, and a cyano group are preferable, and among them, a halogen atom, an alkoxy group, and an acyloxy group are particularly preferable.

Specific examples of the acyloxy group include an acetyloxy group, a benzoyloxy group, an acryloyloxy group, and a 4-benzoyloxybenzoyloxy group.

The alkyl group, aryl group, alkenyl group, alkynyl group, alkoxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group and acyloxy group represented by R ¹ may not be particularly substituted. May be substituted with the following groups.

[0040]

Embedded image

Among the above R ¹ , a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkoxy group, an aryloxycarbonyl group, an acyloxy group and a cyano group are preferred, and a hydrogen atom, a halogen atom, an alkenyl group and an alkoxy group are more preferred. preferable.

In the general formula (1), L ¹ and L ² each independently represent a halogen atom, an alkyl group, an alkoxy group,
Represents a cyano group or a nitro group. The halogen atom, alkyl group and alkoxy group represented by L ¹ or L ² have the same meanings as those in R ¹ described above, and their substituents and preferred embodiments are also the same. Among them, L ¹ and L ² are a halogen atom,
Alkyl groups and alkoxy groups are preferred. Also, l in the equation
And m each independently represent 0, 1, 2;
Or 1 is preferred.

In the general formula (1), “—C ₆ H _4-l (L ¹ ) _l
-C ₆ H _4-m (L ² ) _m -R ¹ ”is preferably a group selected from the following structures,

Embedded image

Among them, the following groups are particularly preferred.

Embedded image

Hereinafter, specific examples (exemplified compounds 1-1 to 1-31) of the optically active compound represented by the general formula (1) are shown. However, the present invention is not limited to these.

[0046]

Embedded image

[0047]

Embedded image

[0048]

Embedded image

[0049]

Embedded image

Next, the compound represented by the following formula (2) will be described.

Embedded image

In the above formula, R ² is a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group. Represents a cyano group. Details of the halogen atom, alkyl group, aryl group, heterocyclic group, alkenyl group, alkynyl group, alkoxy group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, and acyloxy group (specific examples, substitution when substituted) Group, and preferred embodiments) are the same as those of the compound represented by the general formula (1).
^It is the same as the case in ¹ . Among the above R ² , a hydrogen atom, a halogen atom, an alkyl group, an alkenyl group, an alkoxy group, an aryloxycarbonyl group, an acyloxy group, and a cyano group are preferable, and a hydrogen atom, a halogen atom, an alkenyl group, and an alkoxy group are more preferable.

L ³ in the formula (2) represents a halogen atom, an alkyl group, an alkoxy group, a cyano group or a nitro group, and details of the halogen atom, the alkyl group and the alkoxy group (specific examples, Substituents and preferred embodiments, etc.) have the same meanings as in L ¹ or L ² of the compound represented by formula (1). Also, n in the formula
Represents 0, 1, 2, or 3, and particularly preferably 0 or 1.

In the general formula (2), the moiety containing R ² and (L ³ ) _n as terminal groups in the naphthalene ring is preferably a group selected from the following structures.

Embedded image

Among them, the following groups are particularly preferred.

Embedded image

Hereinafter, specific examples (exemplified compounds 2-1 to 2-36) of the optically active compound represented by the general formula (2) will be shown. However, the present invention is not limited to these.

[0056]

Embedded image

[0057]

Embedded image

[0058]

Embedded image

[0059]

Embedded image

[0060]

Embedded image

[0061]

Embedded image

The synthesis of the optically active compound represented by the above general formula (1) or (2) is carried out by (1) a method of esterifying isosorbide and the corresponding carboxylic acid chloride under basic conditions; The corresponding carboxylic acid was DCC
And (3) Mitsunobu reaction between isosorbide and the corresponding carboxylic acid. Isosorbide and the corresponding carboxylic acid chloride can be obtained by reacting the carboxylic acid with oxalyl chloride, thionyl chloride, and the like. Hydrolysis after reaction, or Wittig reaction with carbomethoxymethylenetriphenylphosphorane or the like, or a method by Heck reaction between an aryl halide such as the corresponding aryl bromide and acrylic acid or an acrylate ester, or the like. .

<Photoreactive Chiral Agent> The photoreactive chiral agent of the present invention comprises the optically active compound represented by formula (1) or (2) and can control the alignment structure of the liquid crystal compound. At the same time, it has a characteristic that the helical pitch of the liquid crystal, that is, the helical twisting power (HTP) of the helical structure can be changed by structural isomerization by light irradiation. That is, it is a compound that causes a change in the twisting force of a helical structure induced in a liquid crystal compound, preferably a nematic liquid crystal compound, by light irradiation (ultraviolet light to visible light to infrared light). It has a site (chiral site) and a site that undergoes a structural change by light irradiation.

In addition, the photoreactive chiral agent represented by the general formula (1) or (2) can greatly change the HTP of liquid crystal molecules, in particular. Therefore, for example, in the case of a cholesteric liquid crystal (liquid crystal phase) using a nematic liquid crystal compound as a liquid crystal compound, B (blue), G (green),
Selective reflection over a wide wavelength range including the three primary colors of R (red) is possible. That is, the selective reflection characteristic of the light wavelength is
It is determined by the twist angle of the helical structure of the liquid crystal molecules, and the more the angle changes, the wider the color width of the selective reflection becomes, which is useful.

When the photoreactive chiral agent represented by the general formula (1) or (2) has a structure in which one or more polymerizable bonding groups are introduced in the same molecule, The heat resistance of a liquid crystal composition containing a photoreactive chiral agent, for example, a liquid crystal color filter, an optical film, or the like can be improved.

The molecular weight of the photoreactive chiral agent represented by formula (1) or (2) is preferably 300 or more. 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 HTP represents the twisting force of the helical structure of the liquid crystal, that is, HTP = 1 / (pitch × concentration of chiral agent [mass fraction]). For example, the helical pitch of the liquid crystal molecules at a certain temperature (HTP) One cycle of the helical structure; μm) is measured, and this value can be calculated by converting [μm ⁻¹ ] from the concentration of the chiral agent. When a selective reflection color is formed by the illuminance of light with a photoreactive chiral agent, the change rate of the HTP (= H before irradiation)
(TP / HTP after irradiation) is preferably 1.5 or more when HTP becomes smaller after irradiation.
It is more preferably 5 or more, and when the HTP becomes larger after irradiation, it is preferably 0.7 or less, more preferably 0.4 or less.

The photoreactive chiral agent of the present invention can be used in combination with a known chiral agent having no photoreactivity, such as a chiral compound having a large temperature dependence of the torsional force. Known chiral agents having no photoreactivity include, for example, JP-A-20
00-44451, Tokiohei 10-509726, W
O98 / 00428, JP-T-2000-506873,
Tokuhyo Hei 9-5060888, Liquid Cryst
als (1996, 21, 327), Liquid C
crystall (1998, 24, 219) and the like.

<Liquid Crystal Composition> The liquid crystal composition of the present invention is selected from at least one liquid crystalline compound (preferably a nematic liquid crystal compound) and the above-mentioned optically active compound of the present invention (that is, a photoreactive chiral agent). And the liquid crystal compound may or may not have a polymerizable group. Also, if necessary, other components such as 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, and a gelling agent. May be included. In the liquid crystal composition of the present invention, it is particularly preferable to use a surfactant in combination. For example, in the case of applying a liquid crystal composition in the form of a coating liquid to form a layer, the orientation of liquid crystal molecules at the air interface on the layer surface can be three-dimensionally controlled, and in particular, in the case of a cholesteric liquid crystal phase, selection with higher color purity The reflection wavelength can be obtained.

(Optically Active Compound) As the optically active compound, a photoreactive chiral agent may be used as described in the above general formula (1).
Or a liquid crystal compound, preferably a nematic liquid crystal, which contains an optically active compound represented by (2), controls the alignment structure of liquid crystal molecules three-dimensionally, and irradiates light with a desired pattern and light amount. Changes the helical structure of a compound. The optically active compound (photoreactive chiral agent)
The content of is not particularly limited and can be appropriately selected,
The content is preferably about 0.1 to 30% by mass of the total solid content (mass) of the liquid crystal composition.

(Liquid Crystal Compound) The liquid crystal compound includes
The refractive index anisotropy Δn can be appropriately selected from a liquid crystal compound having a refractive index anisotropy of 0.10 to 0.40, a polymer liquid crystal compound, and a polymerizable liquid crystal compound. For example, a smectic liquid crystal compound, a nematic liquid crystal compound, etc. can be mentioned, and among them, a nematic liquid crystal compound is preferable. For example, a cholesteric liquid crystal composition (cholesteric liquid crystal phase) can be obtained by using a nematic liquid crystal compound as a liquid crystal compound and using the optically active compound represented by the general formula (1) or (2) in combination with the nematic liquid crystal compound. it can. The liquid crystal compound can be aligned while in a liquid crystal state at the time of melting, for example, by using an alignment substrate that has been subjected to an alignment process such as a rubbing process. In the case where the liquid crystal state is solid phase and immobilized, means such as cooling and polymerization can be used.

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

[0073]

Embedded image

[0074]

Embedded image

[0075]

Embedded image

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.

[0077]

Embedded image

Among 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.

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 total solids (mass) of the liquid crystal composition. The content is
If the amount is less than 30% by mass, the orientation may be insufficient, and particularly in the case of a cholesteric liquid crystal, a desired selective reflection color may not be obtained.

(Photopolymerization Initiator) The liquid crystal composition of the present invention may contain a photopolymerization initiator. The polymerization reaction of the polymerizable group is promoted by using the photopolymerization initiator in combination, and the liquid crystal composition is irradiated by light. By fixing the helical structure after changing the helical pitch (twisting force), the strength of the liquid crystal composition after the fixing can be further improved. When a polymerization reaction by a polymerizable liquid crystal compound is used to fix the helical structure of the liquid crystal, it is preferable to add a photopolymerization initiator. For example, when the liquid crystal phase is a cholesteric liquid crystal phase, a desired helical pitch can be stably obtained, and a selective reflection color with high color purity can be secured.

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, etc., and bis (2,4,6-trimethylbenzoyl)-
JP-A-10-2999 such as phenylphosphine oxide
No. 7, the bisacylphosphine oxides described in
acylphosphine oxides described in DE 4230555 of ucirin TPO and the like.

The addition amount of the photopolymerization initiator is preferably from 0.1 to 20% by mass, more preferably from 0.5 to 5% by mass, based on the total solids (mass) of the liquid crystal composition. When the addition 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,
When the ratio exceeds the above range, the light transmittance from the ultraviolet region to the visible light region may be inferior.

As described above, the liquid crystal composition of the present invention contains both the optically active compound represented by the general formula (1) or (2) and a photopolymerization initiator, and the optically active compound is It can change the helical pitch of the liquid crystal by isomerization (trans-cis) by light, and the photopolymerization initiator can promote the polymerization reaction of the polymerizable group by light. It is preferable that the photopolymerization initiator has a different photosensitive wavelength range from the light source wavelength. Here, having different photosensitive wavelengths means that the photosensitive central wavelengths of the two do not overlap, for example, during image-like exposure or polymerization curing, to the extent that hue purity does not decrease due to image display characteristics or selective reflection. This means that the liquid crystal alignment is not changed. To prevent the photosensitive center wavelengths from overlapping,
In addition to relying on the molecular structures of both, it can also be performed by controlling the wavelength of irradiation light through a band-pass filter or the like.

By sensitizing the liquid crystal molecules to light having different wavelengths from each other, the liquid crystal molecules are illuminated imagewise to orient the liquid crystal molecules in a pattern, and then affect the helical pitch of the liquid crystal aligned in the pattern. It can be fixed without giving, and an image having a desired spiral pitch can be obtained. For example, when the liquid crystal phase is a cholesteric liquid crystal phase, a selective reflection color having a desired helical pitch is exhibited, and a hue excellent in color purity can be obtained.

(Polymerizable Monomer) The liquid crystal composition of the present invention has the following properties for the purpose of improving the degree of curing such as film strength.
A polymerizable monomer may be used in combination. When the polymerizable monomer is used in combination, the helical structure (selective reflectivity) is fixed after changing (patterning) the torsional force of the liquid crystal due to light irradiation (for example, after forming the distribution of the selective reflection wavelength). The strength of the liquid crystal composition after the formation 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.

The polymerizable monomer includes, for example, a monomer having an ethylenically unsaturated bond, and specifically, a polyfunctional monomer such as pentaerythritol tetraacrylate and dipentaerythritol hexaacrylate. Specific examples of the monomer having an ethylenically unsaturated bond include the following compounds, but are not limited to these in the present invention.

[0087]

Embedded image

The amount of the polymerizable monomer to be added is preferably 0.5 to 50% by mass based on the total solid content (mass) of the liquid crystal composition. If the addition amount is less than 0.5% by mass, sufficient curability may not be obtained,
If it exceeds 50% by mass, the alignment of the liquid crystal molecules is hindered, and sufficient coloring may not be obtained.

(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, polystyrene compounds such as poly-α-methylstyrene, cellulose resins such as methyl cellulose, ethyl cellulose and acetyl cellulose, acidic cellulose derivatives having a carboxyl group in a side chain, polyvinyl formal, polyvinyl butyral, and the like. Acetal resin of JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, JP-B-54-25957,
Methacrylic acid copolymers and acrylic acid copolymers described in JP-A-59-53836 and JP-A-59-71048;
Examples include an itaconic acid copolymer, a crotonic acid copolymer, a maleic acid copolymer, a partially esterified maleic acid copolymer, and the like.

Homopolymers of alkyl acrylates and homopolymers of alkyl methacrylates are also mentioned. In these, alkyl groups are methyl, ethyl, n-propyl, n-butyl, iso-
-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, a benzyl (meth) acrylate / (homopolymer of methacrylic acid) acrylic acid copolymer or benzyl (meth) acrylate / (meth) acrylic acid / other monomer And the like.

The content of the binder resin in the liquid crystal composition is preferably from 0 to 50% by weight, more preferably from 0 to 30% by weight. When the content exceeds 50% by weight, 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 the photoreactive chiral agent and the 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% by weight is preferable, and 0 to 5% by weight 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 molding 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.

<Method of Changing the Helical Structure of Liquid Crystal> As described above, the liquid crystal composition of the present invention contains a photoreactive chiral agent (optically active compound of the present invention). In the changing method, the liquid crystal composition of the present invention is irradiated with light in a desired pattern at a desired amount of light to change the helical pitch (twisting force) of the liquid crystal, and the helical structure of the liquid crystal, that is, Thus, regions having different degrees of twisting of the spiral (twisting force; HTP) can be formed.

When the liquid crystal phase is a cholesteric liquid crystal phase, the selective reflection color of the liquid crystal can be arbitrarily changed according to the twisting force. When the change rate of the twisting force (torsion change rate) is large, the color width of the selective reflection color that the liquid crystal can selectively reflect is widened, and the selective reflection in a wide wavelength range including the three primary colors (B, G, R) is performed. This is particularly important in that the three primary colors of BGR can be displayed with high color purity. In this respect, the optically active compound represented by the above-mentioned general formula (1) or (2) can significantly change the twisting power of the helical structure of the liquid crystal, and therefore contains the compound (chiral agent). By using a liquid crystal composition, a wide range of hues including the three primary colors of blue (B), green (G), and red (R) can be displayed, and three primary colors having excellent color purity can be obtained. .

Specifically, it can be performed as follows. That is, when a liquid crystal composition is irradiated with light having a certain wavelength, a photoreactive chiral agent (general formula (1)) which coexists depending on the irradiation intensity.
Alternatively, the optically active compound (2) is exposed to light and changes the helical structure (twist angle) of the liquid crystal to form an image-like pattern (patterning). Cholesteric liquid crystal compositions exhibit different selective reflection colors due to this structural change. Therefore, if light irradiation is performed while changing the irradiation intensity for each desired region, the light is oriented according to the irradiation intensity (presents a plurality of colors),
For example, by exposing through an exposure mask formed by changing the light transmittance like an image, an image can be simultaneously formed by a single light irradiation, for example, a colored region having different selective reflection.

Furthermore, since it depends on the optically active compound represented by the general formula (1) or (2), the helical pitch of the liquid crystal can be largely changed, and in the case of the cholesteric liquid crystal composition, the formed color The region shows a wide range of selective reflection colors, and can form three primary colors of BGR having excellent color purity. This light irradiation can be performed without any particular limitation as long as the irradiation intensity can be changed for each desired region, in addition to the method using an exposure mask. Liquid crystal color filter described later,
When forming an optical film or the like, after patterning by exposing the light of a certain wavelength imagewise as described above,
Further, the polymerizable groups in the liquid crystal composition are photopolymerized and cured by light irradiation, and the helical structure of the liquid crystal is fixed to a desired selective reflection color. These forming methods will be described in detail below as “method for fixing the helical structure of the liquid crystal”.

The light source used for light irradiation is preferably a light source that emits ultraviolet light because it has a high energy and can rapidly change the structure of a liquid crystal compound and rapidly perform a polymerization reaction. And the like. Further, it is preferable to have a light quantity variable function.

As described above, when the optically active compound represented by the general formula (1) or (2) is contained in the liquid crystal composition as a chiral agent, the helical pitch (twisting force) of the liquid crystal with respect to the amount of light greatly changes. Can be done. Therefore,
For example, in the case of a cholesteric liquid crystal phase using a nematic liquid crystal compound as a liquid crystal compound, the color width of the selective reflection color that can be exhibited by the liquid crystal is widened, and blue (B) and green having excellent color purity are obtained.
(G) and red (R) can be obtained.

As described above, when the optically active compound represented by the general formula (1) or (2) is used, the change rate of the helical pitch induced in the liquid crystal by light irradiation due to the compound is large. Utilizing that, liquid crystal color filters,
An optical film such as 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. By doping the ferroelectric liquid crystal, the antiferroelectric liquid crystal, and the TGB phase, patterning of a polarization state and patterning of a helical pitch can be performed. 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. Further, the liquid crystal composition of the present invention may contain a non-chiral azo or styrene-based compound which isomerized by light, thereby further increasing the rate of change of the helical pitch during light irradiation. There is.

<Method for Immobilizing the Helical Structure of Liquid Crystal> As described above, the optically active compound (photoreactive chiral agent) represented by the general formula (1) or (2) is irradiated with light having a specific wavelength. Thereby, the helical structure can be changed by changing the twisting force of the coexisting liquid crystal. According to one embodiment, the liquid crystal composition of the present invention includes a liquid crystal compound having a polymerizable group, a photopolymerization initiator, and at least one of the optically active compounds represented by Formulas (1) and (2). It becomes. In the method for fixing a helical structure of a liquid crystal according to the present invention, the changed helical structure can be fixed by polymerizing the liquid crystalline compound, and the strength of the liquid crystal composition after the fixing is improved. Can be further improved. It is preferable that the photopolymerization initiator and the optically active compound have different photosensitive wavelength ranges.

Specifically, it can be performed as follows. That is, first, similarly to the patterning described in the above “method of changing the helical structure of liquid crystal”, light in the photosensitive wavelength region of the optically active compound in the liquid crystal composition is irradiated imagewise. By this light irradiation, the optically active compound is exposed to light and changes the helical structure of the liquid crystal to form an image-like pattern (patterning). After this patterning, light in the photosensitive wavelength region of the photopolymerization initiator in the liquid crystal composition is irradiated. Then, the liquid crystal compound is polymerized by the photopolymerization initiator, and is fixed while maintaining the changed helical structure. Before this step, for example, a step such as nitrogen substitution may be provided.

When the photosensitive wavelength region of the optically active compound is different from the photosensitive wavelength region of the photopolymerization initiator, the irradiation of light for changing HTP and the irradiation of light for photopolymerization do not affect each other. . Therefore, when imagewise exposed to change the HTP, photopolymerization does not proceed, so that patterning with the HTP change rate as set becomes possible, while photopolymerization to fix the helical structure is performed. The optically active compound does not react to light, and the formed HTP change pattern can be reliably immobilized.

In the case of forming a liquid crystal color filter, an optical film or the like to be described later, after light having a wavelength sensitive to the optically active compound is imagewise exposed and patterned as described above, a photopolymerization initiator is further added. The liquid crystal composition is irradiated with light having a wavelength to be sensitized to photopolymerize and cure the polymerizable group in the liquid crystal composition, thereby fixing the helical structure of the liquid crystal to a desired selective reflection color. Details of these forming methods will be described later.

The light source used for light irradiation is the same as the light source exemplified in the above-mentioned “method for changing the helical structure of liquid crystal”.

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 contains at least a liquid crystal compound and at least one kind of the optically active compound of the present invention, and a nematic liquid crystal compound is most preferable as the liquid crystal compound. If necessary, the composition further contains a polymerizable monomer, a photopolymerization initiator, other components listed in the liquid crystal composition of the present invention, and a surfactant that exerts an excluded volume effect. For example, it can be manufactured by irradiating light with a desired pattern and light amount appropriately selected based on the above-mentioned “method of changing the helical structure of liquid crystal” and “method of fixing the helical structure of liquid crystal”.

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 is appropriately selected from the above-described liquid crystal composition of the present invention, and a known composition containing the optically active compound represented by the general formula (1) or (2). Can be manufactured. In this case, the liquid crystal composition may be in the form of a sheet composed only of the liquid crystal composition, or in a mode in which a layer (liquid crystal layer) containing the liquid crystal composition is provided on a desired support or temporary support. And another layer (film) such as an alignment film or a protective film may be provided. In the latter case, two or more liquid crystal layers can be laminated, and in this case, the exposure step described later is provided a plurality of times.

As the nematic liquid crystal compound, polymerizable monomer, photopolymerization initiator and other components, the same ones as those usable in the liquid crystal composition of the present invention can be used.
The content, 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. Further, the content of the optically active compound represented by the general formula (1) or (2) 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 includes, for example,
The liquid crystal composition of the present invention can be suitably manufactured. The method for producing the liquid crystal color filter is not particularly limited. For example, a step of patterning by imagewise exposing with the first light, followed by photopolymerization with the second light and curing (hereinafter, referred to as “ The exposure method may be at least one step. That is, the “method of fixing the spiral structure of the liquid crystal” of the present invention may be applied. In addition, 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 / peeling (transfer step), and a cholesteric liquid crystal composition according to a selected production mode. May be formed through a step of applying a liquid crystal layer to form a liquid crystal layer (coating step).

A specific embodiment using a cholesteric liquid crystal composition will be described below as an example of a production method including the above-mentioned exposure step. -Exposure Step-In the exposure step, both patterning and fixing (polymerization curing) of the liquid crystal compound are performed by light irradiation. That is, after an optically active compound (hereinafter, sometimes referred to as a “photoreactive chiral agent”) is imagewise exposed and patterned with a first light having a wavelength capable of responding with high sensitivity, the polymerization initiator becomes high. The polymer is cured by photopolymerization with the second light capable of responding to the sensitivity, and 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 is exposed to light and the helical structure of the liquid crystal compound changes according to the illuminance. 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 second light and curing (fixing) the second light.

It is preferable that the wavelength of the first light be set in a photosensitive wavelength region of the photoreactive chiral agent, particularly a wavelength close to the photosensitive peak wavelength, in that sufficient patterning sensitivity can be obtained. Further, it is preferable that the wavelength of the second light is set in a photosensitive wavelength region of the polymerization initiator, in particular, a wavelength close to the photosensitive peak wavelength, from the viewpoint of obtaining sufficient photopolymerization sensitivity. Also, the illuminance (irradiation intensity) of the first and second light
Is not particularly limited, and can be appropriately selected depending on the material to be 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, the same light sources as those usable for the light irradiation of the liquid crystal composition can be used.

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 coating liquid can be prepared by dissolving and dispersing each component in an appropriate solvent. Here, as the solvent,
For example, 2-butanone, cyclohexanone, methylene chloride, chloroform and the like can be mentioned. In the production of a liquid crystal color filter, a cholesteric liquid crystal composition is preferred. Between the liquid crystal layer and the temporary support, a cushion layer containing a thermoplastic resin or the like may be provided from the viewpoint of ensuring adhesion during transfer, such as when there is a foreign substance or the like on the transfer target. It is also preferable that the surface of the cushion layer or the like is 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 base 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 peeling the transfer material from the light-transmitting substrate to form a cholesteric liquid crystal layer on the substrate (transfer step). The liquid crystal layer may be formed of a plurality of layers by further laminating after the following (4). (4) the cholesteric liquid crystal layer via the exposure mask is irradiated with ultraviolet illuminance [nu ¹ imagewise to form a pixel pattern illustrating the selectively reflected color, this further curing the layer by irradiation with ultraviolet illuminance [nu ² Step (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 as 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, an alignment film similar to the above may be formed between the cholesteric liquid crystal layer and the temporary support. 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 4
μm is preferred.

Further, an example will be described below with reference to FIGS. 1 to 3 are schematic views showing one embodiment of a process for manufacturing a liquid crystal color filter of the present invention. First, the components described above 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 applied and formed on the support 10. 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, FIG.
As shown in (C), a coating liquid cholesteric liquid crystal composition is applied on the alignment film 14 and dried to form a cholesteric liquid crystal layer 16, and a cover film 18 is provided on the cholesteric liquid crystal layer 16. Create a transfer material. 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 subjected to a rubbing treatment. 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 cholesteric liquid crystal layer 16 of the transfer sheet 20 and the alignment film 24 of the color filter substrate 26 were removed. Are laminated so that they come into contact with the surface of each other, and laminated through a roll rotating in the direction of the arrow in the figure. Thereafter, as shown in FIG. 1- (F), the alignment film 14 of the transfer sheet 20 and the cushion layer 1 are formed.
2 and the cholesteric liquid crystal layer is transferred together with the alignment film 14 on the color filter substrate. In this case, the cushion layer 12 does not necessarily have to 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 arranged above the alignment film 14, and the first exposure mask 28 is provided through the mask 28. Is applied to the cholesteric liquid crystal layer 16 in a pattern. The cholesteric 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 reflects green (G) for each pattern, Blue (B)
And a region that transmits red (R), a region that reflects blue (B), a region that transmits green (G) and red (R), and a region that reflects red (R) to reflect green (G) and blue (B). It is formed so as to form an area to be transmitted.

Next, as shown in FIG. 3H, the cholesteric 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. Thereafter, unnecessary portions (for example, remaining portions of the cholesteric liquid crystal layer 16 such as a remaining portion such as a cushion layer and an intermediate layer and unexposed portions) are removed by using 2-butanone, chloroform, or the like, so that the structure shown in FIG. As shown, a cholesteric 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 formed directly on a color filter substrate. . In this case, when applied to the above embodiment, a cholesteric 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. The steps shown in ()) 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 (1) or (2) is used,
Since the rate of change of the twisting force of the helical structure of the liquid crystal with respect to the amount of light is large, the color width of the selective reflection color that can be exhibited by the liquid crystal is widened, and three colors of blue (B), green (G), and red (R) excellent in color purity are obtained. A liquid crystal color filter consisting of primary colors can be obtained.

<Optical Film> The optical film of the present invention contains at least a liquid crystal compound and at least one kind of the optically active compound of the present invention, and has an optical wavelength arbitrarily set from a wide wavelength range. If necessary, a polymerizable monomer, a photopolymerization initiator, and other components enumerated in the liquid crystal composition of the present invention, such as a surfactant that exerts an excluded volume effect, and the like are appropriately selected from desired components. It can be manufactured by irradiating light with a pattern and light amount. For example, it can be manufactured based on the above-mentioned “method of changing the helical structure of liquid crystal” and “method of fixing the helical structure of liquid crystal”.

The optical film of the present invention is suitably selected from the above-mentioned liquid crystal compositions of the present invention and those comprising a known composition containing the optically active compound represented by the general formula (1) or (2). It can be selectively manufactured. 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 further provided.

As the liquid crystal compound, 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 same applies to the case of the liquid crystal composition. Further, the content of the optically active compound represented by the general formula (1) or (2) in the liquid crystal composition constituting the optical film is 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 prepared, for example, using the liquid crystal composition of the present invention. In addition, as a method for producing an optical film, it can be produced by a method substantially similar to the liquid crystal color filter,
The method may include at least one exposure step. That is, the aforementioned “method of fixing the spiral structure of the liquid crystal” may be applied. 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, the first
And the manufacturing method of the second embodiment.

As described above, when the liquid crystal composition containing the optically active compound represented by the general formula (1) or (2) is used,
It is possible to obtain a non-light-absorbing optical film capable of greatly changing the helical pitch of the liquid crystal with respect to the amount of light. For example, when the liquid crystal phase is a cholesteric liquid crystal phase, the color width of selective reflection of the liquid crystal is widened, an optical film composed of various selective reflection colors, and primary colors (B, G,
The optical film of R) can be obtained.

<Recording Medium> The recording medium of the present invention contains a liquid crystalline compound and at least one kind of the optically active compound of the present invention. If necessary, a polymerizable monomer, a photopolymerization initiator, and an exclusion agent may be used. Such as a surfactant that exerts a volume effect,
The liquid crystal composition of the present invention contains the other components listed in the liquid crystal composition.

The recording medium of the present invention is not limited in its form, and may be in the form of a sheet comprising only a liquid crystal composition, or may have a desired support or temporary support (hereinafter referred to as “support etc.”). ) May be provided with a layer (liquid crystal layer) containing a liquid crystal composition containing a photoreactive chiral agent. Here, the liquid crystal composition is appropriately selected from the above-described liquid crystal composition of the present invention and a known composition containing the optically active compound represented by the general formula (1) or (2). it can. Further, another layer (film) such as an alignment film or a protective film may be provided.

As the liquid crystal compound, the polymerizable monomer and the photopolymerization initiator, and other components, the same compounds as those usable in the liquid crystal composition can be used.
Preferred ranges and the like are the same as in the case of the liquid crystal composition. In addition, the content of the optically active compound represented by the general formula (1) or (2) 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 of providing the liquid crystal composition on a support or the like includes (1) using a transfer material in which a liquid crystal layer containing the liquid crystal composition of the present invention is provided on a temporary support, and then forming the liquid crystal layer on the support. Transfer method, (2) on a support,
A method of directly applying a liquid crystal composition prepared in a coating liquid state,
And the like. In the methods (1) and (2),
With respect to the transfer material and the method of coating, the embodiments exemplified in the liquid crystal composition of the present invention (first and second embodiments)
It can be applied according to the description of FIGS.

The recording medium of the present invention manufactured as described above is irradiated with light in a desired pattern and light amount appropriately selected, so that an image, particularly a cholesteric liquid crystal, can be formed in accordance with the change rate of the twisting force of the liquid crystal. In the case of (1), a colored image composed of selective reflection colors determined by the change rate of the helical pitch can be formed. The image may be formed based on, for example, the above-described “method of changing the helical structure of liquid crystal” and “method of fixing the helical structure of liquid crystal”. Moreover, when the optically active compound represented by the general formula (1) or (2) is used as a chiral agent for changing the liquid crystal structure, the rate of change of the twisting force of the liquid crystal helical structure with respect to the amount of light is large. In particular, in the case of a cholesteric liquid crystal, the hue width at which the liquid crystal is selectively reflected can be widened, and a multicolor image with high color purity can be formed. In addition, the large change rate of the torsional force means higher sensitivity (higher speed) during image formation.
Also greatly contributes. Further, 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 the light source for irradiating light, the same light sources as those usable in the liquid crystal composition of the present invention can be suitably used for optical recording. The same applies to the case of light irradiation for fixing the liquid crystal.

As described above, the use of an optically active compound represented by the above general formula (1) or (2) as a chiral agent for changing the helical structure of liquid crystal molecules allows the twisting force (twisting) of liquid crystal to be improved. Angle) can be greatly changed. In particular, in the case of a cholesteric liquid crystal using a nematic liquid crystal compound, the selective reflection wavelength range obtained by light irradiation is expanded, and as a result, the color purity of the three primary colors of BGR can be further increased. Therefore, the selectivity and vividness of the hue of the liquid crystal are improved, and particularly in the case of a liquid crystal color filter or an optical film, a clear and vivid color image can be displayed. Can be

[0139]

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”.

Example 1 << Synthesis of Optically Active Compound (Exemplified Compound 1-1) Represented by General Formula (1) >> 1.97 g of isosorbide (13.5 m)
mol), 30 ml of ethyl acetate and 9.7 ml of pyridine
(0.12 mol) and 4-dimethylaminopyridine 10
mg and cooled in an ice bath. To this mixture was added 6.72 g (30 mmol) of 4-phenylcinnamic acid and 7.2 of 4-phenylcinnamic acid chloride prepared from oxalyl chloride.
8 g were added. After stirring at room temperature for 8 hours, the mixture was poured into dilute hydrochloric acid, and the resulting solid was collected by filtration. After purification by column chromatography, the product was recrystallized from chloroform / methanol to give 2.37 g of the above-mentioned exemplified compound 1-1.
(4.2 mmol, 31% yield).

The results (data) of identifying the crystals obtained above are shown below. [α] _D ²⁵ -194 ° (c 0.10, CHCl ₃ ). ¹ H-NMR (CDCl ₃ ): δ (in ppm from tetrame)
thylsilane) 7.80 (1H, d), 7.75 (1H,
d), 7.70-7.56 (12H, m), 7.52-
7.35 (6H, m), 6.56 (1H, d), 6.4
8 (1H, d), 5.40 (1H, s), 5.36 (1
H, ddd), 5.00 (1H, dd), 4.63 (1
H, d), 4.18-3.85 (4H, m).

Example 2 << Synthesis of Optically Active Compound (Exemplary Compound 1-9) Represented by General Formula (1) >> 0.69 g of isosorbide (4.7 mm)
ol), 5 ml of methylene chloride and 5 ml of pyridine were added thereto, and while stirring, 2.96 g (10 mmol) of 4- (4-butoxyphenyl) cinnamic acid and 4- (4-butoxyphenyl) cinnamic acid prepared from oxalyl chloride 3.15 g of acid chloride were added. After stirring at room temperature for 10 hours, the mixture was poured into diluted hydrochloric acid, and the resulting solid was collected by filtration. After purification by column chromatography, the product was recrystallized from DMAc / methanol to give 1.2 g of Exemplified Compound 1-9 (1.7 g).
mmol, yield 36%).

The results (data) of identifying the crystals obtained above are shown below. [α] _D ²⁵ -178 ° (c 0.10, CHCl ₃ ). ¹ H-NMR (CDCl ₃ ): δ (in ppm from tetrame)
thylsilane) 7.80 (1H, d), 7.73 (1H,
d), 7.65-7.50 (10H, m), 7.03-
6.97 (4H, m), 6.55 (1H, d), 6.4
7 (1H, d), 5.40 (1H, s), 5.36 (1
H, ddd), 5.00 (1H, dd), 4.63 (1
H, d), 4.20-3.90 (8H, m), 1.90
-1.70 (4H, m), 1.60-1.42 (4H,
m), 1.05-0.90 (3H, m).

Example 3 << Synthesis of Optically Active Compound (Exemplified Compound 2-7) Represented by General Formula (2) >> 0.66 g of isosorbide (4.5 mm)
ol), 10 ml of acetonitrile and 3.2 m of pyridine
l (40 mmol) and 4-dimethylaminopyridine 10
mg and cooled in an ice bath. The mixture was added to 3- (6
-Methoxynaphthalen-2-yl) acrylic acid 2.28
g (10 mmol) and oxalyl chloride
2.47 g of (6-methoxynaphthalen-2-yl) acrylic acid chloride were added. After stirring at room temperature for 10 hours, the mixture was poured into diluted hydrochloric acid, and the resulting solid was collected by filtration. Purification by column chromatography gave 70 mg (0.12 mmol, 2.7 yield) of Exemplified Compound 2-7 as a white solid.
%)Obtained.

The results (data) of identifying the crystals obtained above are shown below. [α] _D ²⁵ -202 ° (c 0.10, CHCl ₃ ). ¹ H-NMR (CDCl ₃ ): δ (in ppm from tetrame)
7.95-7.58 (10H, m), 7.
21-7.10 (4H, m), 6.62-6.43 (2
H, m), 5.40 (1H, s), 5.36 (1H, d
dd), 5.00 (1H, dd), 4.63 (1H,
d), 4.20-4.05 (3H, m), 4.00-
3.90 (7H, m).

(Example 4): Measurement of change in helical pitch due to light irradiation 0.5 part of the exemplified compound 1-1 (optically active compound of general formula (1) (photoreactive chiral agent)) obtained above was used. Nematic liquid crystal composition (ZLI-1132, manufactured by Merck) 99.5
And then injected into a wedge-type cell (glass thickness: 1.1 mm, blue plate) that had been subjected to uniaxial orientation treatment with a polyimide orientation film. Here, when the helical pitch at room temperature was measured using a polarizing microscope, it was 3.40 μm. When this is converted into helical twisting power (HTP), 6
0 μm ⁻¹ .

Next, the above wedge type cell was irradiated with ultraviolet rays from a high pressure mercury lamp at an irradiation intensity of 300 mW / cm ² for 3 minutes. After irradiation, the helical pitch at room temperature was measured in the same manner as above, and it was found to be 15.8 μm. This is 13 μm ⁻¹ when converted to HTP. Therefore, the HTP change rate was 4.6. As described above, the helical torsional force (HTP) could be greatly changed by the irradiation of the ultraviolet rays. In addition, when the direction of the twist before and after the irradiation of the ultraviolet rays was confirmed by the contact method, the twist was right before and after the irradiation.

(Example 5): Measurement of change in helical pitch due to light irradiation 1.0 part of Exemplified Compound 2-7 (optically active compound of general formula (2) (photoreactive chiral agent)) obtained above was used. The mixture was mixed with 99 parts of a nematic liquid crystal composition (ZLI-1132, manufactured by Merck) and injected into a wedge-type cell (glass thickness: 1.1 mm, blue plate) that had been subjected to uniaxial alignment treatment with a polyimide alignment film. Here, when the helical pitch at room temperature was measured using a polarizing microscope, it was 2.55 μm. When this is converted into helical twisting power (HTP), 40
μm ⁻¹ .

Next, the above wedge-type cell was irradiated with ultraviolet rays from a high-pressure mercury lamp at an irradiation intensity of 300 mW / cm ² for 3 minutes. After irradiation, the helical pitch at room temperature was measured in the same manner as described above, and it was found to be 10.1 μm. This is 10 μm ⁻¹ when converted to HTP. Therefore, the HTP change rate was 4.0. As described above, the helical torsional force (HTP) could be greatly changed by the irradiation of the ultraviolet rays. In addition, when the direction of the twist before and after the irradiation of the ultraviolet rays was confirmed by the contact method, the twist was right before and after the irradiation.

Example 6 Preparation 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 5 minutes with an ultra-high pressure mercury lamp at this temperature through a band-pass filter having a light source center wavelength of 365 nm. Then held in the dark in a state maintained at 110 ° C. 5 min, then remove the band-pass filter, further exposing the entire surface irradiation energy 500 mJ / cm ² by the same ultra-high pressure mercury lamp and the while blowing nitrogen gas,
Polymerized and cured. As described above, a circularly polarized light reflecting plate was produced.

[0152]

Embedded image

The circularly-polarized light reflecting plate obtained above was 460-6
It exhibited selective reflection in a wide wavelength range over 60 nm, and had sufficient band characteristics as a broadband circularly polarized light reflecting plate. Moreover, the right circularly polarized light reflectance at a selective reflection wavelength of 550 nm was 98%.

Example 7 Preparation of Broadband Circularly Polarized Light Reflecting Plate The procedure of Example 6 was repeated, except that the formulation of the coating solution used for preparing the circularly polarized light reflecting plate was changed to the following formulation. Thus, a circularly polarized light reflecting plate was produced.

[0155]

Embedded image

The circularly-polarized light reflecting plates obtained above were 470 to 6
It exhibited selective reflection in a wide wavelength range over 70 nm, and had sufficient band characteristics as a broadband circularly polarized light reflector. Moreover, the right circularly polarized light reflectance at a selective reflection wavelength of 550 nm was 98%.

Example 8: Preparation of Liquid Crystal Color Filter (1) Preparation of Filter Substrate A polyimide alignment film (LX-1400, manufactured by Hitachi Chemical DuPont) was applied on a glass substrate by a spin coater. After drying in an oven at 100 ° C for 5 minutes, 2
It was baked in an oven at 50 ° C. 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 the coating solution was heated to 110 ° C. For 2 minutes to form a photosensitive resin layer.

[0159]

Embedded image

Next, the photosensitive resin layer was held on a hot plate at 110 ° 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 is arranged via a photomask and a bandpass filter centered at 365 nm,
Irradiation was performed with an ultra-high pressure mercury lamp through this photomask and bandpass filter to perform patterning. The irradiation energy at this time was 300 mJ / cm ² for the red pixel.
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 ² by the same ultra-high pressure mercury lamp while blowing nitrogen gas.
The entire surface was further exposed and polymerized and cured. Furthermore, in order to promote the degree of curing of the filter portion (photosensitive resin layer), the
For 20 minutes to obtain a color filter on which red, green, and blue pixel patterns were formed. At the time of the patterning, the helical pitch of the liquid crystal (twisting force of the liquid crystal) can be largely changed by irradiation,
A pixel pattern composed of red, green, and blue with high color purity could be formed.

(Example 9): Preparation of liquid crystal color filter In Example 8, the formulation of the photosensitive resin layer coating solution used for forming the photosensitive resin layer was changed to the following formulation.
A liquid crystal color filter was produced in the same manner as in Example 8.

[0163]

Embedded image

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 10): Preparation of optical compensation film for STN element A polyethylene vinyl alcohol (PVA) film having a saponification degree of 99.5% was formed by bar coating on triacetyl cellulose (TAC) having a thickness of 80 μm. And 110 ° C
Heated under 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.

[0166]

Embedded image

Next, at a temperature of 100 ° C., ultraviolet irradiation (irradiation energy 1) was performed from above the film using a high-pressure mercury lamp.
2,000 mJ / cm ² ) to polymerize and cure the film.
An optical compensation film for an N element was produced (hereinafter, referred to as "STN compensation film"). 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 the film is prepared, and these films are overlapped so that the liquid crystal molecules in the matched portion are orthogonal to each other, and the absorption axes are orthogonal to each other. It was inserted between two polarizing plates and visually observed, and showed a good black color. Therefore, it was confirmed that the film (STN compensation film) formed as described above functions as an optical compensation film for an STN element.

(Example 11): Preparation of optical compensation film for STN element In Example 8, the same procedure as in Example 10 was repeated except that the formulation of the coating solution used for forming the film was changed to the following. An optical compensation film was produced.

[0169]

Embedded image

When the film thickness of the produced STN compensation film 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. Further, this film has a twist angle (-240 degrees) opposite to that of the film.
A TN compensating film was prepared, these were overlapped so that the liquid crystal molecules in the matched portions were orthogonal, and inserted between two polarizing plates whose absorption axes were orthogonal to each other. . Therefore, it was confirmed that the film (STN compensation film) formed as described above functions as an optical compensation film for an STN element.

(Example 12): Prevention of generation of reverse twist domain for TN element A polyimide alignment film (LX-1400, Hitachi Chemical DuPont Co., Ltd.) was formed on an ITO film of a glass substrate having an ITO film.
Coating solution was applied by a spin coater, dried in an oven at 100 ° C for 5 minutes, and then dried in an oven at 250 ° C.
After firing for an hour, an alignment film was formed. 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 with the alignment films were arranged so that the alignment films faced each other, and bonded with a two-liquid epoxy resin adhesive mixed with spacer beads having a diameter of 6 μm to form driving cells. 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]-Nematic liquid crystal composition ... 99.9% (ZLI-1132, manufactured by Merck)-Photoreactive chiral agent of the present invention (the above-mentioned exemplified compound 1-9) ... 0.1%

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.

(Example 13): Prevention of generation of reverse twist domain for TN device In Example 12, the photo-reactive chiral agent used in the preparation of the composition injected into the cell was replaced with the compound of Example 2 described above.
Example 12 except that 7 (photoreactive chiral agent) was used.
Visual observation was carried out in the same manner as in the above. As a result, generation of a reverse twist domain was not recognized. 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.

[0175]

According to the present invention, it is possible to provide a novel optically active compound which has photosensitivity and can undergo structural change by isomerization by light. According to the present invention, the orientation of the liquid crystal compound can be controlled, and the rate of change in the helical pitch (twist force) of the liquid crystal due to light (the rate of change in twist) is large. A photoreactive chiral agent capable of performing selective reflection over a wide range including the primary colors (B, G, R) and displaying three primary colors with high color purity can be provided.
According to the present invention, the helical pitch (twisting force) of the liquid crystal by light
And a liquid crystal composition containing a photoreactive chiral agent having a large twist change rate, and capable of controlling the alignment state of liquid crystal molecules three-dimensionally by light to change optical characteristics. For example, in the case of a cholesteric liquid crystal, it is possible to provide a liquid crystal composition which exhibits a wide range of selective reflection colors including the three primary colors by light irradiation and can display the three primary colors with excellent color purity.

According to the present invention, a liquid crystal composition containing a photoreactive chiral agent having a large twist change rate is irradiated with light to change the helical pitch (twist force) of the liquid crystal, thereby changing the helical structure of the liquid crystal. A method can be provided. According to the present invention, a liquid crystal composition containing a photoreactive chiral agent having a large twist change rate can be immobilized in a state where the patterned helical pitch is maintained without loss after imagewise exposure.
Particularly, when the liquid crystal phase is a cholesteric liquid crystal phase, a method for fixing the spiral structure of the liquid crystal, which can fix the spiral structure of the liquid crystal to a desired selective reflection color and obtain a hue with high color purity. Can be.

According to the present invention, it is possible to provide a liquid crystal color filter having high color purity, which contains a photoreactive chiral agent capable of largely changing the helical pitch (twisting force) of the liquid crystal by light irradiation. ADVANTAGE OF THE INVENTION According to this invention, the non-light-absorbing optical film containing the photoreactive chiral agent which can change the twisting force of a liquid crystal greatly by light irradiation can be provided. For example, when a cholesteric liquid crystal phase is used, an optical film having a wide selective reflection region and high color purity can be provided. According to the present invention, it is possible to provide a recording medium that includes a photoreactive chiral agent that can greatly change the twisting force of liquid crystal by light irradiation, and that can form a clear image by changing the amount of light imagewise. . For example, when a cholesteric liquid crystal phase is used, it is possible to provide a recording medium capable of forming an image composed of a selective reflection color having a wide hue and high color purity.

[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 of manufacturing a liquid crystal color filter of the present invention.

FIG. 3 is a schematic view showing a part of a process 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 substrate for color filter 28 exposure mask

 ──────────────────────────────────────────────────続 き Continued on the front page F term (reference) 4C071 AA01 BB01 CC12 EE05 FF15 HH05 JJ01 LL05 4H027 BA13 BE01 DH01 DH03 DH05 DN01 DN03 DN05

Claims (11)

[Claims] 1. An optically active compound represented by the following general formula (1). Embedded image [In the general formula (1), R ¹ represents a hydrogen atom, a halogen atom,
Alkyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, a cyano group, L ¹ and L ² are halogen independently Represents an atom, an alkyl group, an alkoxy group, a cyano group, or a nitro group. l and m are each independently 0, 1, 2
Represents ] 2. An optically active compound represented by the following general formula (2). Embedded image [In the general formula (2), R ² represents a hydrogen atom, a halogen atom,
Represents an alkyl group, an aryl group, a heterocyclic group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyloxy group, a cyano group, and L ³ represents a halogen atom, an alkyl group, an alkoxy group. Represents a group, a cyano group, or a nitro group. n represents 0, 1, 2, and 3. ] 3. A photoreactive chiral agent comprising the optically active compound according to claim 1. 4. A liquid crystal compound according to claim 1,
And a liquid crystal composition containing at least one selected from the optically active compounds described in 2. 5. A liquid crystal composition comprising a liquid crystal compound having at least one polymerizable group, at least one selected from the optically active compounds according to claim 1 and 2, and a photopolymerization initiator. 6. The liquid crystal composition according to claim 5, wherein the optically active compound and the photopolymerization initiator according to claim 1 have different photosensitive wavelength ranges. 7. A liquid crystal helix which irradiates the liquid crystal composition according to claim 4 with light to change the structure of the optically active compound represented by the general formula (1) or (2). How to change the structure. 8. The liquid crystal composition according to claim 4, which is irradiated imagewise with light in the photosensitive wavelength range of the optically active compound represented by formula (1) or (2). And then irradiating light in the photosensitive wavelength region of the photopolymerization initiator to carry out photopolymerization, which comprises fixing the helical structure of the liquid crystal. 9. At least a liquid crystal compound and a liquid crystal compound
3. A liquid crystal color filter comprising at least one selected from the optically active compounds described in 2. and 2. 10. An optical film comprising at least a liquid crystalline compound and at least one selected from the optically active compounds according to claim 1. 11. A recording medium comprising at least a liquid crystalline compound and at least one selected from the optically active compounds according to claim 1.