JP2958410B2 - Liquid crystal / polymer composite material, electro-optical element, and method for producing them - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a liquid crystal / polymer composite material on a substrate and an electro-optical element using the same. More specifically, display elements such as displays, dimming elements,
As a light modulation element, an optical shutter and a memory element,
The present invention relates to a liquid crystal / polymer composite material that can be widely applied, an electro-optical element using the same, and a method for manufacturing the same.

[0002]

2. Description of the Related Art Low molecular weight liquid crystal materials are widely used for flat panel displays and the like. For example, TN type liquid crystal display elements such as clock faces and STN type liquid crystal display elements for portable computers and portable word processors. Widely used for such applications. These control the transmission / non-transmission (ON / OFF) of light by utilizing the property that the polarization plane of the light passing through the liquid crystal layer changes according to the applied voltage, so that a total of two sheets are provided on both sides of the liquid crystal layer. A polarizing plate is required. In addition, it is indispensable to perform an alignment film treatment for the liquid crystal layer to assume a specific alignment state. In recent years, a liquid crystal display device in which a low-molecular liquid crystal compound is dispersed or microencapsulated and held in a polymer binder has been proposed. For example, Japanese Patent Publication No. 58-50163
No. 1 discloses a film in which nematic liquid crystal droplets encapsulated in polyvinyl alcohol are dispersed. When no voltage is applied, this film scatters light incident on the film because the nematic liquid crystal in the liquid crystal droplets is aligned along the capsule wall surface, while the voltage is applied. It is considered that the nematic liquid crystal takes two states of scattering and transmission in which light incident on the film is transmitted because the nematic liquid crystal is oriented in the direction of the electric field.

Further, JP-T-61-502128 and JP-A-62-2231 disclose that a polymerizable composition of a polymerizable compound such as epoxy and a low-molecular liquid crystal compound is polymerized by applying ultraviolet light or heat. Patent Document 1 discloses that a liquid crystal element having a configuration in which liquid crystal droplets are dispersed and held in a polymer binder is produced by polymerizing a hydrophilic composition to cause phase separation. Further, JP-A-2-55787 discloses that
In the above-described phase separation method by ultraviolet polymerization, a liquid crystal element capable of lowering a driving voltage by increasing the ratio of a low-molecular liquid crystal compound used is disclosed. The liquid crystal / polymer composite materials disclosed in the above publications do not require a polarizing plate, which was indispensable for a liquid crystal display device, so that bright display is possible and an alignment film and a rubbing treatment are not required. . Therefore, it is easy to increase the area of the element, and it is also advantageous in terms of manufacturing cost.

[0004]

However, a conventional liquid crystal having a low molecular weight liquid crystal material held in a polymer binder has a disadvantage.
When an element made of a polymer composite material is applied to a display element, generally, the steepness of the change in transmittance with respect to an applied voltage is low, and it is difficult to drive a simple matrix like an STN type liquid crystal element, and a TFT (thin film transistor) is driven. Need. However, the conventional liquid crystal / polymer composite material has a problem that the driving voltage is generally as high as several tens of volts, and it is difficult to apply it to TFT driving, and even if possible, the display contrast is low. Furthermore, there is a problem that the display characteristics are deteriorated during use and the characteristics are deteriorated due to heat. Accordingly, an object of the present invention is to provide a liquid crystal / polymer composite material which is drivable by a TFT element and has a low driving voltage of 10 V or less, high display contrast, excellent durability and heat resistance, and an electro-optical element comprising the same. Is to do. Another object of the present invention is to provide a method for producing the liquid crystal / polymer composite material and the electro-optical element.

[0005]

That is, the liquid crystal / polymer composite material of the present invention comprises a low molecular weight liquid crystal compound and a high molecular weight compound capable of repeating a cloudy state and a transparent state by controlling an electric field or a magnetic field. Is present in a phase-separated state, and the polymer compound is at least acrylic acid 2
-Butoxyethyl ester and polyfunctional acrylic acid ester
It is a polymer of a polymerizable composition containing a tellurium. The above-mentioned liquid crystal / polymer composite material of the present invention comprises a composition comprising at least a low molecular liquid crystal compound, a polymerizable composition containing 2-butoxyethyl acrylate and a polyfunctional acrylate , and a composition comprising a polymerization initiator on two substrates. It is manufactured by pouring in between and polymerizing by application of heat, light or electron beams. The electro-optical element of the present invention is provided with a liquid crystal / polymer composite material in which a low-molecular liquid crystal compound and a high-molecular compound are present in a phase-separated state between two substrates. , At least acrylic acid 2
-Butoxyethyl ester and polyfunctional acrylic acid ester
It is a polymer of a polymerizable composition containing a tellurium. The electro-optical element of the present invention comprises at least a low-molecular liquid crystal compound, acrylic acid 2-butoxyethyl ester and
A composition comprising a polymerizable composition and a polymerization initiator containing polyfunctional acrylate and a polymerization initiator is injected between two substrates having a polymerizable group formed on the opposite inner surface thereof, and heat, light or electron beam is applied. It can be produced by polymerizing and bonding the polymerizable group to a polymer compound in the composite material by a chemical reaction.

Hereinafter, the present invention will be described in detail. The liquid crystal / polymer composite material applied to the electro-optical element of the present invention exhibits its function when the low-molecular liquid crystal compound and the high-molecular compound are phase-separated from each other. The form of the phase separation may be such that each liquid crystal droplet is dispersed and held, or a plurality of liquid crystal droplets may be aggregated. The shape of the liquid crystal droplet may be spherical or polyhedral as in the case where the polymer compound forms a thin film-like wall. Further, the liquid crystal may form a continuous phase.

The microstructure (phase-separated structure) of the liquid crystal / polymer composite material can be variously changed depending on the properties (thermodynamic properties and chemical properties) and the mixing ratio of the low-molecular compound and the high-molecular compound used. An example is shown in the schematic diagram of FIG. FIG. 1 (A)
Is an example in which the high molecular compound 2 is used in excess of the low molecular liquid crystal compound 1, and illustrates a liquid crystal / polymer composite material 3 in which the low molecular liquid crystal compound 1 is dispersed in the polymer compound 2 in the form of microdroplets. Is shown. FIG. 1B shows an example in which low-molecular liquid crystal compound 1 and high-molecular compound 2 are used in substantially equal amounts, and illustrates a liquid crystal-polymer composite material 3 in which sponge-like phase separation is performed. FIG. 1C is an example in which the low-molecular liquid crystal compound 1 is used in excess of the high-molecular compound 2, and the liquid crystal / polymer film in which the high-molecular compound 2 is separated into a fibrous phase in the low-molecular liquid crystal compound 1 3 is illustrated. In these descriptions, the description was made based on the mixed amount of the low-molecular liquid crystal compound and the high-molecular compound. However, as described above, the properties of the low-molecular liquid crystal compound and the high-molecular compound (thermodynamic properties) And chemistry) affect its microstructure.

The low-molecular liquid crystal compound constituting the liquid crystal / polymer composite material of the present invention is used as a general display material such as a nematic liquid crystal, a cholesteric liquid crystal, a smectic liquid crystal, and a ferroelectric liquid crystal, or as an electric field driven display material. Various liquid crystal materials used can be used.
Specifically, biphenyl-based, phenylbenzoate-based,
Various liquid crystal compounds such as cyclohexylbenzene, azoxybenzene, azobenzene, azomethine, terphenyl, biphenylbenzoate, cyclohexylbiphenyl, phenylpyrimidine, cyclohexylpyrimidine, and cholesterol are exemplified. These low-molecular liquid crystal compounds need not be a single composition, as in the case of commonly used liquid crystal materials, and may be a composition composed of a plurality of components. Further, when the purpose is display by an electric field, it is preferable to use a liquid crystal compound having a positive dielectric anisotropy among the above low-molecular liquid crystal compounds. Depending on the liquid crystal, when the frequency of the applied voltage becomes larger than a certain value (crossover frequency), the dielectric anisotropy changes from positive to negative. However, the liquid crystal can be used for two-frequency driving. Needless to say.

A feature of the present invention is that the polymer compound forming the liquid crystal / polymer composite material is at least 2- butyl acrylate.
It consists of a polymer of a polymerizable composition containing toxic ethyl ester and polyfunctional acrylate .

[0010] The polymerizable composition used in the present invention comprises the above-mentioned acrylic acid 2-butoxyethyl ester and a polyfunctional compound.
Contains acrylic acid ester as an essential component, but also various other polymerizable compounds (hereinafter referred to as monomers)
Can be used. For example, (meth) acrylic acid alkyl ester, (meth) acrylic acid ester derivative containing hetero ring or aromatic ring, (meth) acrylamide, (meth) acrylic acid hydroxyethyl ester, (meth) acrylic acid, vinylpyrrolidone, styrene And its derivatives, and monofunctional monomers such as acrylonitrile, vinyl chloride, vinylidene chloride, ethylene, butadiene, isoprene, and vinylpyridine .

The polymerization composition according to the present invention comprises acrylic acid
Including 2-butoxy-ethyl ester and polyfunctional acrylic acid esters may be further blended acrylic acid alkyl ester in the composition. In these cases, the mixing ratio of the monofunctional monomer containing 2-butoxyethyl acrylate to the polyfunctional acrylate is 10
It is preferably selected from the range of 0: 1 to 1: 2.

Next, a method for producing a liquid crystal / polymer composite material will be described. A composition in which a low-molecular liquid crystal compound, a polymerizable compound, and a polymerization initiator are mixed in advance (hereinafter, referred to as a polymerizable composition) is prepared. The mixing ratio of the low-molecular liquid crystal compound and the polymerizable compound in the polymerizable composition is selected from the range of 20: 1 to 1:10 by weight, more preferably 10: 1 to 1: 1. . As the polymerization initiator, a thermal polymerization initiator such as an azo compound or a peroxide, or a photopolymerization initiator represented by a phenyl ketone-based compound is used. The amount of the polymerization initiator to be added is preferably in the range of 1/1000 to 1/10 by weight relative to the polymerizable composition. A liquid crystal / polymer composite material is prepared by applying the above composition on a base material or injecting the composition between two substrates and polymerizing the composition by applying heat, light or an electron beam.

Next, an electro-optical element using the liquid crystal / polymer composite material of the present invention will be described. As a form of the electro-optical element, a configuration in which the liquid crystal / polymer composite material is sandwiched between two substrates with electrodes is preferably applied. An example is shown in FIG. 2, which has a configuration sandwiched between two substrates 4 and 5 with electrodes, like a normal liquid crystal element. In FIG.
Voltage is applied to the substrates 4 and 5 with electrodes from the composite material 3
When the low-molecular liquid crystal compound 1 in the state is oriented in the electric field direction (1
FIG. When this voltage is applied, light incident on the composite material 3 is transmitted without being scattered.

As the substrate with electrodes in the above-mentioned electro-optical element, for example, a so-called transparent conductive glass in which an ITO (indium-tin oxide) film or a tin oxide film is provided on a glass base material, or an ITO film on a polyester film is provided. A conductive polyethylene terephthalate (PET) film or the like is used. In addition, as one of the substrates with electrodes, an aluminum-deposited film, a gold-deposited film, a silver-deposited film, an aluminum plate, a copper plate, or the like is used. In addition, in order to adjust the thickness of the composite material layer, it is preferable to use a conventionally used appropriate spacer material such as glass particles, resin particles, alumina particles, glass fibers, and films.

Further, as the above-mentioned substrate with electrodes, it is preferable to use a substrate having a polymerizable group formed on the substrate surface. In this case, a composition containing a low-molecular liquid crystal compound is injected between substrates having a polymerizable group formed on the opposite inner surface thereof, and heat,
By polymerizing by applying light or electron beam,
This is because the surface of the base material and the polymer compound in the liquid crystal / polymer composite material are directly bonded, and excellent durability, thermal stability, and high display characteristics can be obtained. As a method of forming a polymerizable group on the substrate surface, a method of applying a polymer compound having a polymerizable group to the substrate surface, a surface treatment of the substrate surface or a coating of a reactive polymer compound on the substrate surface may be used. After a reactive group is formed, a low molecular compound having a polymerizable group is bonded to the reactive group.

Examples of the polymer compound having a polymerizable group applied to the substrate surface include various polymers having a polymerizable group such as a vinyl group or a (meth) acryloyl group in a main chain or a side chain. These polymer compounds can be easily prepared by adding a compound having a polymerizable group such as a vinyl group or a (meth) acryloyl group to the polymer compound. For example, in a reactive polymer compound having a reactive group such as a hydroxyl group, a carboxyl group, an amino group, or a thiol group in a side chain, a polymer group such as a vinyl group or a (meth) acryloyl group and a group bonding to the reactive group in the polymer Such as a vinyl-containing silane coupling agent, a (meth) acryloyl-containing silane coupling agent and a (meth) containing silane coupling agent.
It is easily achieved by reacting an acryloyl group isocyanate compound or the like. As the polymer compound having a polymerizable group used in the present invention, specifically,
Polyvinyl alcohol and polyhydroxyethyl (meth)
Partial (meth) acryloyl products of acrylate, partially vinylated products of polyvinyl alcohol and polyhydroxyethyl (meth) acrylate, and the like can be given. The thickness of the polymer compound layer having a polymerizable group is 0.01 μm to 1 μm.
A range of 0 μm is preferred.

Next, after a reactive group is formed on the substrate surface by surface treatment of the substrate surface or application of a high molecular compound to the substrate surface, a low molecular compound having a polymerizable group is reacted with the reactive group. Next, a method of forming a polymerizable group on the substrate surface will be described. In this method, it is necessary to form a reactive group by applying an appropriate treatment to the substrate surface in advance. As the reactive group in this case, a reactive group such as a hydroxyl group, a carboxyl group, an amino group or a thiol group is preferably applied in view of the bonding strength. As a method of forming such a reactive group on the substrate surface, in the case of surface treatment of the substrate surface, the substrate is heated to a high temperature in an active oxygen or water vapor atmosphere, plasma treated, or the substrate is treated with an alkali or an acid. By immersion, various reactive groups such as hydroxyl groups can be formed on the substrate surface. When a polymer compound having a reactive group is applied, the reactive group is applied to the surface of the substrate by applying a polymer compound having a reactive group such as a hydroxyl group, a carboxyl group, an amino group or a thiol group on a side chain. Can be formed. Specific examples of the polymer compound having a reactive group used in the present invention include polyvinyl alcohol, partially saponified polyvinyl acetate, hydroxyethyl poly (meth) acrylate, and alkyl- (meth) acrylate- (meth) acrylate. A) acrylic acid copolymer, alkyl (meth) acrylate-hydroxyethyl (meth) acrylate copolymer and the like.

Next, the reactive group formed on the substrate surface by such a surface treatment or the application of the reactive polymer compound has a functional group and a polymerizable group which can be bonded to the reactive group in one molecule. By reacting the molecular compound, a low molecular compound having a polymerizable group can be formed on the substrate surface. In that case, after providing a reactive group on the substrate surface by using a low molecular compound having a polymerizable group by a vapor deposition method, a coating method, an adsorption method, an LB film method, a self-organizing method, or the like, an appropriate method such as heating is performed. They can be combined by performing processing. As the low-molecular compound having a polymerizable group used in this case, a vinyl-containing silane coupling agent, a (meth) acryloyl-containing silane coupling agent, a (meth) acryloyl-containing isocyanate compound and the like can be used. Examples thereof include triethoxyvinylsilane, divinyldichlorosilane, allylmethyldichlorosilane, dimethylvinylchlorosilane, allyldimethylchlorosilane, methoxydimethylvinylsilane, trimethoxyvinylsilane, diallyldichlorosilane, ethoxydimethylvinylsilane, diethoxymethylvinylsilane, and diethoxy. Divinylsilane, 3- (vinylbenzylaminopropyl) trimethoxysilane, 3- (vinylbenzylaminopropyl) triethoxysilane, N- (3
-(Meth) acryloxy-2-hydroxypropyl)-
3-aminopropyltriethoxysilane, 3- (meth)
Acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropyldimethoxymethylsilane, 3
-(Meth) acryloxypropylmethyldichlorosilane and 3- (meth) acryloxypropyltrichlorosilane. The thickness of the layer formed using the low molecular compound having a polymerizable group is 1 molecular layer to 10 layers.
The range of μm is preferred.

The liquid crystal / polymer composite material of the present invention can be applied as a display element or a light modulation element even if it comprises only two components, a low molecular liquid crystal compound and a high molecular compound.
Further, various compounds can be added for the purpose of improving contrast and stability. For example, various dichroic dyes such as anthraquinone type, styryl type, azomethine type and azo type can be used for the purpose of improving the contrast. In that case, it is preferable that the dichroic dye is basically compatible with the low-molecular liquid crystal compound in the composite material and is incompatible with the high-molecular compound. In addition, antioxidants,
UV absorbers, various plasticizers, and the like are also preferably used from the viewpoint of improving stability and durability. The liquid crystal / polymer composite material of the present invention and the electro-optical element using the same can realize excellent display characteristics and low voltage driving by using a specific polymerizable composition. Further, it is a useful electro-optical element that exhibits excellent display characteristics, durability, and thermal stability by being manufactured using a substrate on which a polymerizable group is formed, and is a display element, a dimming element, and a light modulation element. It is an excellent thing that can be widely applied as a light shutter or a light shutter.

[0020]

EXAMPLES Next, examples will be described, but the present invention is not limited to these examples. [Evaluation Method] The electro-optical properties of the prepared samples were evaluated by the following methods. While the white light from the 50 W halogen lamp is made into parallel light through a lens and made perpendicular to the sample, an AC voltage of 100 Hz and a rectangular wave is applied to the sample, and the maximum spread angle transmitted through the sample while changing the applied voltage. The transmitted light intensity of about ± 10 ° was measured. The following parameters were determined from the obtained applied voltage-transmitted light intensity curve (FIG. 3). Driving voltage: V90 = voltage when transmitted light intensity changes by 90% of total change amount Contrast: CR = Tmax / Tmin Here, Tmax and Tmin indicate maximum and minimum values of transmittance. Further, some of the samples were evaluated as changes in electro-optical characteristics before heating and after heating at 100 ° C. and left for 5 minutes.

[0021]

Example 1 3 parts by weight of 2-butoxyethyl acrylate, 1 part by weight of 1,6-hexanediol diacrylate, and Darocure 1173 (manufactured by MERCK) as a photopolymerization initiator.
08 parts by weight to prepare a polymerizable composition. Further, as 2 parts by weight of the polymerizable composition and a low-molecular liquid crystal compound,
8 parts by weight of E8 (manufactured by MERCK) were mixed to prepare a polymerizable composition. Two glass substrates with ITO 10 μm
Using the resin spacer of
Was sealed with an adhesive to produce a cell. Polymerizable in this cell
The composition was injected, and a high-pressure mercury lamp (15 mW / cm ² , 36
(5 nm) for 1 minute to polymerize. The obtained electro-optical element was visually uniformly clouded. Also,
Observation with a polarizing microscope revealed that the low-molecular liquid crystal compound formed fine domains separated from each other.

Example 2 3 parts by weight of 2 -butoxyethyl acrylate, 3 parts by weight of butyl acrylate, 2 parts by weight of 1,6-hexanediol diacrylate and Darocure 1 as a photopolymerization initiator
173 (manufactured by MERCK) was mixed to prepare a polymerizable composition. Further, 2 parts by weight of the polymerizable composition and E8 (manufactured by MERCK) as a low-molecular liquid crystal compound were used.
8 parts by weight were mixed to prepare a polymerizable composition. This polymerizable composition was injected into a cell in the same manner as in Example 1 and polymerized.
The obtained electro-optical element was visually uniformly clouded.
Further, when observed with a polarizing microscope, the low-molecular liquid crystal compound formed fine domains separated from each other.

[0024] Example 3 2-butoxyethyl acrylate, 3 parts by weight of 2-ethylhexyl acrylate, 3 parts by weight of 1,4 porcine Nji O <br/> Darocure 1173 as diacrylate 1.5 part by weight of photopolymerization initiator ( (MERCK) 0.16 parts by weight was mixed to prepare a polymerizable composition. Further, 2 parts by weight of the polymerizable composition and E8 (ME
8 parts by weight (manufactured by RCK) were mixed to prepare a polymerizable composition. This polymerizable composition was injected into a cell in the same manner as in Example 1 and polymerized. The obtained electro-optical element was visually uniformly clouded. Further, when observed with a polarizing microscope, the low-molecular liquid crystal compound formed fine domains separated from each other.

Example 4 A glass substrate provided with an ITO (indium tin oxide) film as a transparent conductive layer was treated with a 1% aqueous solution of NaOH.
% Aqueous hydrochloric acid. Through this process, hydroxyl groups were formed on the ITO surface. A 1% chloroform solution of 3-acryloxypropyltrichlorosilane was applied on the substrate and dried, and then reacted at a temperature of 60 ° C. for 2 hours under nitrogen substitution to form an acryloyl group as a polymerizable group on the surface. Using this substrate, a cell was produced in the same manner as in Example 1. The polymerizable composition used in Example 3 was injected into a cell in the same manner and polymerized. The obtained electro-optical element was visually uniformly clouded. Further, when observed with a polarizing microscope, the low-molecular liquid crystal compound formed fine domains separated from each other.

Comparative Example 1 A polymerizable composition was prepared by mixing 3 parts by weight of butyl acrylate, 1 part by weight of 1,6-hexanediol dialactate, and 0.08 part by weight of Darocur 1173 (manufactured by MERCK) as a photopolymerization initiator. Was prepared. Further, 2 parts by weight of the polymerizable composition and E8 (MERC) as a low-molecular liquid crystal compound were used.
8 parts by weight (manufactured by K Company) were mixed to prepare a polymerizable composition.
This polymerizable composition was injected into a cell in the same manner as in Example 1 and polymerized. The obtained electro-optical element was visually uniformly clouded. Further, when observed with a polarizing microscope, the low-molecular liquid crystal compound formed fine domains separated from each other.

Comparative Example 2 3 parts by weight of 2-ethylhexyl acrylate and 1,4
-1 part by weight of butanediol diolate and Darocure 1173 (MERCK) 0.1 as a photopolymerization initiator
6 parts by weight were mixed to prepare a polymerizable composition. Further, 2 parts by weight of this polymerizable composition and E8 as a low-molecular liquid crystal compound were used.
8 parts by weight (manufactured by MERCK) were mixed to prepare a polymerizable composition. This polymerizable composition was injected into a cell in the same manner as in Example 1 and polymerized. The obtained electro-optical element was visually uniformly clouded. Further, when observed with a polarizing microscope, the low-molecular liquid crystal compound formed fine domains separated from each other.

COMPARATIVE EXAMPLE 3 3 parts by weight of 2-ethylhexyl acrylate, 1 part by weight of trimethylolpropane triacrylate and 0.1 of Darocure 1173 (manufactured by MERCK) as a photopolymerization initiator.
6 parts by weight were mixed to prepare a polymerizable composition. Further, 2 parts by weight of the polymerizable composition and E as a low molecular weight liquid crystal compound
7 (manufactured by MERCK) was mixed with 8 parts by weight to prepare a polymerizable composition. This polymerizable composition was injected into a cell in the same manner as in Example 1 and polymerized. The obtained electro-optical element was visually uniformly clouded. Further, when observed with a polarizing microscope, the low-molecular liquid crystal compound formed fine domains separated from each other.

[Evaluation Results] Table 1 shows the evaluation results of the electro-optical elements made of the liquid crystal / polymer composite materials produced in Examples 1 to 4 and Comparative Examples 1 to 3.
In the table, A indicates before heating and B indicates after heating.

[Table 1]

As is clear from Table 1, the driving voltage (V90) is lower and the contrast is higher in the sample of the embodiment than in the comparative example. Further, from the comparison of Example 3, 4, without any change in the electro-optical properties before and after heating in Example 4, it can be seen that the excellent thermal stability. From the above evaluation results, the electro-optical element of the present invention is useful and excellent in display characteristics and thermal stability, and is not only applicable to a TET drive display element, but also widely used as a dimming element and a light modulation element. It can be seen that the liquid crystal / polymer composite material and the electro-optical element are useful and applicable.

[0031]

According to the liquid crystal / polymer composite material of the present invention, excellent display characteristics and low voltage driving can be realized by using the above specific polymerizable composition. That is, there are excellent effects of 1) high contrast, 2) low drive voltage, 3) applicable to TET drive display elements, and 4) high thermal stability. Therefore, the electro-optical element of the present invention, particularly, an electro-optical element manufactured using a substrate on which a polymerizable group is formed exhibits excellent display characteristics, durability, and thermal stability. Further, since the electro-optical element of the present invention does not require a polarizing plate, a bright display can be performed, and the electro-optical element can be used as a large-screen display element. Furthermore, it is an excellent device that can be widely applied as a light control element, a light modulation element, an optical shutter, and the like.

[Brief description of the drawings]

FIG. 1 is a schematic view of a liquid crystal / polymer composite film according to the present invention.

FIG. 2 is a schematic configuration diagram of an electro-optical element using a liquid crystal / polymer composite film according to the present invention.

FIG. 3 is a graph showing the relationship between applied voltage and transmittance of a liquid crystal / polymer composite film.

[Explanation of symbols]

DESCRIPTION OF SYMBOLS 1 ... Low molecular liquid crystal compound, 2 ... High molecular compound, 3 ... Composite material, 4 and 5 ... Substrate with electrodes, 6 ... Power supply.

────────────────────────────────────────────────── ─── Continuation of front page (56) References JP-A-5-117324 (JP, A) JP-A-6-324313 (JP, A) JP-A-5-148482 (JP, A) JP-A-5-148482 203930 (JP, A) JP-A-6-3651 (JP, A) JP-A-6-27441 (JP, A) JP-A-6-27443 (JP, A) JP-A-6-59246 (JP, A) JP-A-6-123866 (JP, A) JP-A-6-208107 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) G02F 1/1333 G02F 1/137 G02F 1/13 500 C09K 19/52

Claims (5)

(57) [Claims] 1. A liquid crystal / polymer composite material in which a low-molecular liquid crystal compound and a high-molecular compound are present in a phase-separated state, wherein the low-molecular liquid crystal compound and the high-molecular compound are capable of repeating a cloudy state and a transparent state by controlling an electric field or a magnetic field. When the molecular compound is at least acrylic acid 2-butoxyethyl ester and polyfunctional acrylic
A liquid crystal / polymer composite material, which is a polymer of a polymerizable composition containing a luic ester . 2. The liquid crystal / polymer composite material according to claim 1, wherein the polymerizable composition contains 2-butoxyethyl acrylate, alkyl acrylate and polyfunctional acrylate. . Wherein at least a low molecular liquid crystal compound, 2-butoxy ethyl esters, and polyfunctional acrylate acrylate
Production of a liquid crystal / polymer composite material characterized by injecting a composition comprising a polymerizable composition containing an ester and a polymerization initiator between two substrates and polymerizing the composition by applying heat, light or an electron beam. Method. 4. An electro-optical element provided with a liquid crystal / polymer composite material in which a low-molecular liquid crystal compound and a high-molecular compound are present in a phase-separated state between two substrates, wherein the high-molecular compound is at least acrylic. Acid 2-butoxyethyl ester
And a polymer of a polymerizable composition containing a polyfunctional acrylate . 5. At least a low-molecular liquid crystal compound, 2-butoxyethyl acrylate and polyfunctional acrylic acid
Injecting a composition comprising a polymerizable composition containing an ester and a polymerization initiator between two substrates having polymerizable groups formed on their opposing inner surfaces, and polymerizing by applying heat, light or an electron beam. And bonding the polymerizable group to a polymer compound in the composite material by a chemical reaction.