JPH0616616A - Reactive liquid crystal compound, polymeric liquid crystal compound, liquid crystal composition and liquid crystal element - Google Patents

Abstract

PURPOSE:To provide a reactive liquid crystal compound excellent in the film- forming property, permitting to produce liquid crystal elements good in responding properties and having large areas, and capable of giving optoelectric thin films excellent in optical characteristics. CONSTITUTION:A compound of formula I (R<1> is H, alkyl, halogen; U, V, W, X, Y are single bond, -O-, -OCO-, -COO-; (a) is 0, 1; (b), (f) are 0-15; (c), (d), (e) are 0-2), e.g. a compound of formula II. The exemplified compound of formula II is obtained by reacting 6-chloro-hexanol with p-hydroxybenzoic acid and subsequently with acrylic acid and then reacting the produced p-(6- acryloyloxyhexyloxy)benzoic acid with 2,3-dicyano-p-hydroquinone. The compound of formula I and a reactive liquid crystal compound having a polymerizable functional group, e.g. a compound of formula III, are radical- or ionic-copolymerized to provide a polymeric liquid crystal compound.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel reactive liquid crystal compound, a polymer liquid crystal compound using the same, a polymer liquid crystal composition, and a liquid crystal device using them.

The reactive liquid crystalline compound, the polymer liquid crystal compound and the polymer liquid crystal composition of the present invention are used for displays and memories.
Can be used as optoelectronic materials, optical equipment materials and the like.

[0003]

2. Description of the Related Art As a conventional liquid crystal element, for example,
"Applied Physics" by M. Schadt and W. Helfrich
s Letters ") Volume 18, Issue 4 (Published February 15, 1971), pages 127-128," Voltage Dependant Optical Activity of a Twisted Nematic Liquid Crystal ". ("Voltage Dependent
Optical Activity of a Twi
Sted Nematic Liquid Crystal
al ”) shown in Twisted nematic (twi
A liquid crystal device using a liquid crystal is known. However, this TN liquid crystal has a problem that crosstalk occurs during time-division driving using a matrix electrode structure having a high pixel density, and thus the number of pixels is limited.

Further, the use as a display has been limited because of slow electric field response and poor viewing angle characteristics. In addition, the process of forming a thin film transistor in each pixel is extremely complicated, and it is difficult to form a large-area display element.

In order to improve the drawbacks of the conventional liquid crystal device, the use of a bistable liquid crystal device is disclosed by Clark and Lagerw.
all) proposed. (JP-A-56-107
216, US Pat. No. 4,367,924, etc.)
As the liquid crystal having this bistability, a ferroelectric liquid crystal having a chiral smectic C phase (Sm ^* C) or H phase (Sm ^* H) is generally used. Since the ferroelectric liquid crystal has spontaneous polarization, it has a very fast response speed and can exhibit a bistable state having a memory property. Furthermore, since it has excellent viewing angle characteristics, it is considered to be suitable as a material for a large-capacity, large-area display. However, when actually forming a liquid crystal cell, it is difficult to form a monodomain over a wide area, and there is a technical problem in producing a display device having a large screen.

Further, an example is known in which a polymer liquid crystal is used as a memory medium. For example, V. Shibayev (V.
Shibaev), S. Kostromin (S. Kost)
romin), N.Pla'te,
S. Ivaov, V. Vestrov, I. Yakovlev (I.
“Polymer Communications” by Yakovlev (“Polymer Communicatio”)
ns ") 24, pp. 364-365," Thermotropic Liquid Crystalline Polymers. 14 "
("Thermotropic Liquid Cry
tallline Polymers. 14 ") may be mentioned.

However, this method has not been put to practical use due to the problem that the contrast is poor because it utilizes the scattering of light for reading and the response speed is delayed due to the polymerization.

Attempts have also been made to produce a large-area liquid crystal device using polymer liquid crystals, but there is a drawback that the large area is hindered because the molecular weight is not sufficiently large.

On the other hand, attempts have been made to use polymer liquid crystals as optical thin films by utilizing the optical anisotropy of liquid crystals and the film properties of polymers. (Japanese Patent Laid-Open No. 63-303385, etc.) Also, from the same idea, attempts have been made to use a polymer liquid crystal as an alignment film for a liquid crystal element. (JP-A-2
However, in such an attempt, since the molecular weight of the polymer liquid crystal was not sufficiently large,
There is a drawback that the film property is not sufficient and the film is twisted or compatible with the liquid crystal.

In order to make up for such drawbacks, attempts have been made to use crosslinked polymer liquid crystals. [polymer
Science and Technology (Plenum) 198
5 years, 28, 275-368) However, since the structure of the cross-linking component is different from that of the liquid crystal, the liquid crystallinity is impaired.

[0011]

DISCLOSURE OF THE INVENTION The present invention has found a novel reactive liquid crystal compound which avoids the drawbacks of the conventional examples. A polymer liquid crystal compound or polymer composition using the compound, which is capable of forming a liquid crystal device having a large area, which is excellent in responsiveness and which is excellent in optical characteristics, can be obtained. It is intended to provide a liquid crystal element used.

[0012]

That is, the first invention of the present invention is a reactive liquid crystalline compound represented by the following general formula [1].

[0013]

[Chemical 4]

(In the formula, R ¹ represents a hydrogen atom, an alkyl group or a halogen group. U, V, W, X and Y are the same or different, single bond, --O--, --OCO-- or --COO--. A represents 0 or 1. b,
f represents the same or different integers from 0 to 15. c, d, and e are the same or different 0
Represents an integer from 1 to 2. )

The second invention of the present invention is the above-mentioned general formula [1].
Is a polymer liquid crystal compound having a reactive liquid crystal compound represented by A third invention of the present invention is a polymer liquid crystal composition containing the polymer liquid crystal compound of the second invention.

A fourth invention of the present invention is a liquid crystal device characterized by using a reactive liquid crystalline compound having a structure represented by the general formula [1], and a liquid crystal device represented by the general formula [1]. A liquid crystal device characterized by using a polymer liquid crystal compound or a polymer liquid crystal composition obtainable by using a liquid crystal compound having a structure according to claim 1.

The present invention will be described in detail below. The reactive liquid crystal compound of the first invention of the present invention has the above general formula [1].
It is a compound having a structure represented by. In the general formula [1], both ends are reactive functional groups, mesogen is present in the vicinity of the center, and a flexible spacer connects the mesogen and the reactive functional group. Specific examples of this reactive liquid crystal compound include compounds represented by the following structures.

[0018]

[Chemical 5]

[0019]

[Chemical 6]

[0020]

[Chemical 7]

[0021]

[Chemical 8]

Needless to say, the reactive liquid crystalline compound of the present invention is not limited to the above specific examples. A method for synthesizing a typical reactive liquid crystal compound of the present invention is shown below.

[0023]

[Chemical 9] DCC indicates dicyclocarboximide.

Next, the polymer liquid crystal compound of the second invention of the present invention is a polymer liquid crystal compound having a reactive liquid crystal compound having a structure represented by the general formula [1] as a polymerization component. The method for producing the polymer liquid crystal compound generally includes a method of polymerizing a reactive liquid crystal compound of another aspect of the present invention with another reactive liquid crystal compound. The specific manufacturing method includes the following methods, but is not limited to the following methods.

1) A method of obtaining a reactive liquid crystal compound having a polymerizable functional group and a compound having a structure represented by the general formula [1] by radical polymerization or ionic polymerization in a solution state. 2) A reactive liquid crystal compound having a functional group that reacts with the polymer compound having a main chain having a reactive site and a compound having a structure represented by the general formula [1] are graft-polymerized. To get the reaction. 3) A reactive liquid crystal compound having a polymerizable functional group and a compound having a structure represented by the general formula [1] are polymerized by UV irradiation in a liquid crystal state, a molten state, a solid state, or a solution state. How to get it.

In the polymer liquid crystal compound of the present invention, the reactive liquid crystallinity having the structure represented by the general formula [1] is used in an arbitrary ratio. Further, a reactive compound having no liquid crystallinity can also be copolymerized and used. It is also possible to copolymerize and use a functional compound such as a reactive dye.

Specific examples of the other reactive liquid crystal compounds used in the above-mentioned polymerization methods 1) to 3) include the following compounds, but of course, are not limited to the following compounds.

[0028]

[Chemical 10]

[0029]

[Chemical 11]

[0030]

[Chemical 12]

Specific examples of the polymer compound having a main chain having a reactive site used in the polymerization method 2) include the following compound having a repeating unit.

[0032]

[Chemical 13]

In the case of (E), it can be produced by reacting a liquid crystal compound having a vinyl group in a graft manner in the presence of a catalyst. Similarly, in the case of (F) and (G),
It can be produced by reacting a liquid crystal compound having a reactive functional group in a graft manner.

The number average molecular weight of the polymer liquid crystal compound of the present invention is 2,000 to 10,000,000, preferably 20,0 from the viewpoint of sufficient film property and stable film property.
It is from 00 to 10,000,000.

The third invention of the present invention is a polymer liquid crystal composition containing the polymer liquid crystal compound of the second invention. Examples of other components contained in the polymer liquid crystal composition include a low molecular weight compound, a low molecular weight liquid crystal compound, a polymer compound, and a polymer liquid crystal compound. Further, it may contain a dye, a stabilizer, a UV absorber and the like.

Specific examples of the low molecular weight liquid crystal compound include the following, but are not limited to the following.

[0037]

[Chemical 14]

[0038]

[Chemical 15]

[0039]

[Chemical 16]

[0040]

[Chemical 17]

[0041]

[Chemical 18]

[0042]

[Chemical 19]

[0043]

[Chemical 20]

[0044]

[Chemical 21]

(20) Merck Z-1625 nematic temperature range -10 to 60 ° C (21) BDH E-7 nematic temperature range -10 to 60 ° C (22) Roche R-200 nematic temperature range 0 to 65 ° C (23) Dainippon Ink and Electronics D-X01A Nematic temperature range -26 to 68 ° C (24) Merck ZLI-2008 Tcl =
64 ° C (25) Merck ZLI-1840 Tcl =
90 ° C (26) DIC TN403 Tcl =
82 ° C

Specific examples of the polymer liquid crystal compound of the present invention include the followings, but of course the invention is not limited to the followings.

(15> n in the following formulas (31) to (43)
≧ 1. )

[0048]

[Chemical formula 22]

[0049]

[Chemical formula 23]

(In the following equations (44) to (46), p = 5 to
1000, p ₁ + p ₂ = 5 to 1000, q = 1 to 1
6, q ₁ = _{1 to} 16, and q ₂ = _{1 to} 16. )

[0051]

[Chemical formula 24]

(In the formulas (45) and (46), R is 1 carbon atom.
Is an alkyl group or an alkoxy group of ~ 12. (In the formulas (47) to (75) below, * represents an asymmetric carbon center, and n = 5 to 1000.)

[0053]

[Chemical 25]

[0054]

[Chemical formula 26]

[0055]

[Chemical 27]

[0056]

[Chemical 28]

[0057]

[Chemical 29]

[0058]

[Chemical 30]

[0059]

[Chemical 31]

[0060]

[Chemical 32]

[0061]

[Chemical 33]

The content of the polymer liquid crystal compound in the polymer liquid crystal composition of the present invention is usually 5 wt% or more, preferably 10 wt% or more. If it is less than 5% by weight, sufficient film properties and stable film properties may not be obtained.

A polymer liquid crystal compound of the second invention of the present invention;
The polymer liquid crystal composition of the third invention, when exhibiting a nematic liquid crystal phase, can be used for a liquid crystal device using a switching mode similar to that of a conventional TN liquid crystal. Further, when it exhibits a chiral smectic liquid crystal phase, it can be used for a liquid crystal element using a ferroelectric switching mode having bistability. In addition, it can be used in or as a liquid crystal element as an electro-optic thin film having a nematic liquid crystal phase or a smectic liquid crystal phase electro-optical property by fixing the orientation.

A fourth invention of the present invention has a liquid crystal device using a reactive liquid crystal compound having a structure represented by the general formula [1], and a structure represented by the general formula [1]. It is a liquid crystal device using a polymer liquid crystal compound or a polymer liquid crystal composition which can be obtained by using a liquid crystal compound.

An example of the polymer liquid crystal device of the present invention is a method of coating the polymer liquid crystal compound or polymer liquid crystal composition of the present invention on a substrate made of any material such as glass, plastic or metal. Form a film, but on the substrate I
A transparent electrode such as a TO film or a patterned electrode can be formed.

1 (a) and 1 (b) show an example of the polymer liquid crystal device of the present invention. FIG. 1 (a) is a plan view of the polymer liquid crystal device of the present invention, and FIG. 1 (b) is its AA. It is a ′ line sectional view.
FIG. 1 shows an example in which the polymer liquid crystal compound of the present invention is applied to a display device.

In FIG. 1, the polymer liquid crystal device of the present invention comprises a pair of substrates 1 and 1'made of a glass plate or a plastic plate (at least one substrate has birefringence).
Have a cell structure in which the spacers 4 are held at a predetermined interval, and the pair of substrates 1 and 1 ′ are bonded with an adhesive 6 to seal the substrates. Further, a plurality of transparent electrodes 2 are provided on the substrate 1. An electrode group (for example, a scanning voltage applying electrode group in the matrix electrode structure) is formed in a predetermined pattern such as a strip pattern. Also, the substrate 1 '
An electrode group (for example, a signal voltage applying electrode group in the matrix electrode structure) composed of a plurality of transparent electrodes 2'intersecting the transparent electrode 2 is formed on the above.

Substrates 1 and 1'provided with such transparent electrodes 2 and 2'are, for example, silicon monoxide, silicon dioxide, aluminum oxide, zirconia, magnesium fluoride, cerium oxide, cerium fluoride and silicon nitride. Substances, inorganic insulating materials such as silicon carbide and boron nitride, polyvinyl alcohol, polyimide, polyamide imide, polyester imide, polyparaxylelline, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyamide, polystyrene, cellulose resin, melamine resin It is possible to provide the orientation control films 5 and 5'formed by coating with an organic insulating material such as urea resin or acrylic resin.

The alignment control films 5 and 5'are obtained by forming a film of the above-mentioned inorganic insulating material or organic insulating material and then rubbing the surface in one direction with velvet, cloth or paper. To be In another preferred embodiment of the present invention, an inorganic insulating material such as SiO or SiO ₂ is applied to the substrate 1,
Orientation control films 5 and 5'can be obtained by forming a film on 1'by an oblique vapor deposition method.

In another embodiment, the surface of the substrate 1, 1'made of glass or plastic or the substrate 1, 1 '.
After the above-mentioned inorganic insulating material or organic insulating material is formed as a film on the surface of the film, the surface of the film is etched by the oblique etching method, whereby the orientation control effect can be imparted to the surface.

It is preferable that the above-mentioned orientation control films 5 and 5'also function as insulating films at the same time. Therefore, the thickness of the orientation control film is generally set in the range of 100Å to 1 µm, preferably 500Å to 5000Å. can do. This insulating layer also has an advantage that it can prevent the generation of a current caused by a small amount of impurities contained in the polymer liquid crystal layer 3, and therefore does not deteriorate the liquid crystal compound even if the operation is repeated. .

Further, in the polymer liquid crystal device of the present invention, the orientation control film may be provided only on one side of the surface of the substrate 1 or the substrate 1 ′ which is in contact with the polymer liquid crystal layer containing the polymer liquid crystal compound.

The polymer liquid crystal compound and the composition thereof can obtain good alignment not only by the alignment method using an alignment film but also by the following alignment method. As a method for surely performing molecular alignment, a stretching method such as uniaxial stretching, biaxial stretching, inflation stretching, or rearrangement by shearing is preferable. If the film alone has no film property and is difficult to stretch, it can be co-stretched by sandwiching it in a film to obtain a desired orientation.

Next, examples of the polymer film which can be used as the substrates 1 and 1'include, but not limited to, those shown below. That is, low-density polyethylene film, high-density polyethylene film (Mitsui Toatsu Kagaku Hibron, etc.), polypropylene film (Toray Trefan, etc.), polyester film (DuPont Mylar, etc.), polyvinyl alcohol film (Nippon Synthetic Chemical Industry, Hycelon, etc.), polyamide Film (Toyo Gosei film, Reifan etc.),
Polycarbonate film (Teijin Teijin Panlite, etc.), polyimide film (DuPont KAPTON
Etc.), polyvinyl chloride film (Mitsubishi resin Hishirex etc.), polytetrafluoroethylene film (Mitsui Fluorochemical Teflon etc.), polyacrylic film (Sumitomo Bakelite Sumilite), polystyrene film (Asahi Dow Styrosheet), polyvinylidene chloride Examples include films (Asahi Dow Saran film), cellulose films, polyvinyl fluoride films (DuPont Tedlar), and the like.

In the present invention, a polarizing film, a polarizing beam splitter, or the like can be used as the polarizer 7, 7 '.

In the polymer liquid crystal display device of the present invention, a thermal head or a laser beam can be used when displaying is effected by heating.

As the laser light, gas lasers such as He-Ne gas laser, Ar ²⁺ gas laser and N ₂ gas laser, ruby laser, glass laser, YAG are used.
It is desirable to use a solid laser such as a laser or a semiconductor laser. Further, a semiconductor laser having a wavelength range of 600 nm to 1600 nm is preferably used. Particularly preferably, a semiconductor laser having a wavelength range of 600 to 900 nm is used. Further, the wavelength can be shortened by using the second and third harmonics of these laser lights.

When laser light is used, a light absorbing layer is provided separately, or is dispersed and dissolved in the display layer before use. In the case where the display surface is affected by the light absorbing layer or the light absorbing agent, it is desirable that the material does not absorb in the visible light region.

Examples of the laser light absorbing compound added to the polymer liquid crystal layer include azo compounds, bisazo compounds,
Trisazo compounds, anthraquinone compounds, naphthoquinone compounds, phthalocyanine compounds, naphthalocyanine compounds, tetrabenzoporphyrin compounds,
There are aminium salt compounds, diimonium salt compounds, metal chelate compounds, and the like.

Of the above-mentioned laser light absorbing compounds, the compounds for semiconductor lasers absorb in the near infrared region, are useful as stable light absorbing dyes, and have good compatibility or dispersibility with polymer liquid crystal compounds. In addition, some of them have dichroic properties, and if these dichroic compounds are mixed in the polymer liquid crystal, a thermally stable host-guest type memory and display medium can be obtained. . Further, the polymer liquid crystal compound may contain two or more kinds of the above compounds.

Further, the above compounds may be combined with other near infrared absorbing dyes or dichroic dyes. Representative examples of near-infrared absorbing dyes that can be suitably combined are cyanine, merocyanine, phthalocyanine, tetrahydrocholine, dioxazine, anthraquinone, triphenodithiazine, xanthene, triphenylmethane, pyrylium, croconium, azulene and triphenylamine. And the like.

The amount of the above compound added to the polymer liquid crystal compound is about 0.1 to 20% by weight, preferably 0.5 to 10%.

When the polymer liquid crystal device exhibits a nematic liquid crystal phase, it can use the same switching mode as that of the conventional TN type liquid crystal, and when it exhibits a chiral smectic liquid crystal phase, it has a bistable ferroelectric property. Switching mode can be used. When a ferroelectric switching mode is used in which a chiral smectic liquid crystal phase is exhibited, it is necessary to eliminate the helix in order to realize bistability in the device. For that purpose, it is necessary to make the film thickness sufficiently thin. is there. Specifically, it may be 10 μm or less.

Another typical example of the liquid crystal element of the fourth aspect of the present invention is a thin film using the electrical and optical anisotropy of which the orientation is fixed and the thin film is used. It is an element.

Such a thin film comprises, for example, a compound having a structure represented by the general formula [1] of the first invention of the present invention and a reactive liquid crystallinity such as a) to w) shown above. A liquid crystal composition containing a compound is used as a polyimide rubbing film or SiO ₂ film.
It can be obtained by applying it to a substrate having an orientation control film such as an oblique vapor deposition film, orienting it in a liquid crystal state, and then irradiating it with ultraviolet rays and polymerizing and curing it. Additives such as a photoinitiator, a dye, and an antioxidant can be added to the liquid crystal composition containing the compound having the structure represented by the general formula [1] and other reactive liquid crystal compounds.

Since such a thin film has a large birefringence due to the optical characteristics of the liquid crystal,
It can be used for a quarter-wave plate, an optical recording medium, and the like.
Patterning is possible by masking during exposure, and it can be used as an optical waveguide. Since the film thickness can be made extremely thin as compared with the commonly used optical thin film, it has an advantage that the transmittance is remarkably large, and the application range is very wide.

[0087]

The reactive liquid crystal compound having a structure represented by the general formula [1] of the present invention is a bifunctional, cross-linkable compound having a chemical structure with high liquid crystallinity, and has a long molecular axis. It has a large polar group of two cyano groups in the vertical direction. Therefore, when the reactive liquid crystal compound is used, cross-linking polymerization of the polymer liquid crystal compound can be achieved without impairing the liquid crystallinity. In addition, it is possible to easily produce an electro-optic thin film having excellent characteristics.

[0088]

EXAMPLES The present invention will now be described in more detail with reference to examples, but the present invention is not limited to the following examples.

Example 1

[0090]

[Chemical 34] Synthesis of

13.6 g of 6-chloro-hexanol
And 11.0 g of p-hydroxybenzoic acid were heated and refluxed with KOH in an ethanol aqueous solution for 10 hours. Dilute hydrochloric acid was added, and the precipitate was collected by filtration. Recrystallization from ethanol gave 9.5 g of p- (6-hydroxyhexyloxy) benzoic acid (a).

Sulfuric acid was added to 9.5 g of p- (6-hydroxyhexyloxy) benzoic acid (a) and 10.0 g of acrylic acid in toluene in the presence of hydroquinone to give 50.
Heated to reflux for hours. The solvent was distilled off, recrystallized, and p-
8.1 g of (6-acryloyloxyhexyloxy) benzoic acid (b) was obtained.

3.5 g of p- (6-acryloyloxyhexyloxy) benzoic acid (b) was heated under reflux in 5 ml of thionyl chloride and 20 ml of toluene for 2 hours in the presence of 2,6-di-t-butylphenol. To this, 10 ml of anhydrous THF and 1 ml of anhydrous pyridine were added, and the mixture was heated at 0-5 ° C.
A solution of 1.0 g of 2,3-dicyano-p-hydroquinone in anhydrous THF was added. 1 hour at 5 ° C, 1 hour at room temperature,
The mixture was stirred at 50 ° C for 15 hours. Dilute hydrochloric acid was added, and the mixture was continuously extracted with ethyl acetate. The solvent was distilled off, and the residue was purified by column chromatography to obtain 2.1 g of the desired compound (I). The IR spectrum of compound (I) is shown in FIG.

Example 2 0.046 g of the compound (I) obtained in Example 1 and 1.00 g of the compound (II) represented by the following structure were added to DMF.
At 55 ° C. for 40 hours, AIBN was used as a polymerization initiator for polymerization (II).

[0095]

[Chemical 35]

Reprecipitation was repeated in methanol to obtain 0.72 g of polymer (2a).

Mn = 26,300 Mw = 102,200 (measured by GPC) Phase transition temperature

[0098]

[Equation 1]

The ¹ H-NMR spectrum of the polymer (2a) is shown in FIG.

Example 3 0.057 g of compound (I) and 1.00 g of compound (II)
Was polymerized in the same manner as in Example 2. It was similarly purified to obtain 0.68 g of polymer (3a).

Mn = 31,600 Mw = 129,500 Phase transition temperature

[0102]

[Equation 2] The ¹ H-NMR spectrum of the polymer (3a) is shown in FIG.

Comparative Example 1 1.00 g of compound (II) was polymerized and purified in the same manner as in Example 2 to obtain polymer A.

Mn = 1,400 Mw = 21,000 Phase transition temperature

[0105]

[Equation 3]

Example 4 A 7 wt% DMF solution of polymers (2a) and (3a) was applied to a glass substrate with a polyimide rubbing film. 100
When dried and annealed at 40 ° C. for 40 hours, thin films having the polymers (2a) and (3a) uniformly oriented and having no unevenness were obtained.

Comparative Example 2 Polymer A was treated with 7 wt% DMF in the same manner as in Example 4.
The solution was applied to a glass substrate with a polyimide rubbing film.
When dried and annealed at 100 ° C for 40 hours,
Unlike the polymers (2a) and (3a), wrinkles were observed at several places.

Example 5 Each component below

[0109]

[Chemical 36]

[0110] was mixed and melted, and applied on a glass substrate with a polyimide rubbing film. It was held in the nematic liquid crystal state and uniaxially aligned. When a 150 W ultraviolet lamp was irradiated from a distance of 30 cm to polymerize and cure, a thin film having uniform uniaxial orientation was obtained.

Example 6 Polymer (2a) obtained in Example 2 and compound (II)
Were used to prepare the two compositions shown in Table 1 below.

[0112]

[Table 1]

Polymer (2a), three kinds of compounds of X and Y, and a composition were applied to an ITO transparent electrode substrate on which a polyimide rubbing alignment film was formed, and ITO was applied from the top.
A transparent electrode substrate was adhered to form a cell. When an AC electric field of 20 V / μm was turned on and off in the nematic phase, the response of the molecule following the electric field was observed under a polarizing microscope.

[0114]

As described above, according to the present invention, by using a novel reactive liquid crystal compound, a polymer liquid crystal compound using the compound, and a polymer composition, excellent film properties can be obtained. It is possible to realize a large-area liquid crystal element having excellent responsiveness, and it is possible to obtain an electro-optic thin film having excellent optical characteristics.

[Brief description of drawings]

1 shows an example of a polymer liquid crystal device of the present invention, and FIG.
1A is a plan view of a polymer liquid crystal device of the present invention, FIG.
Is a sectional view taken along the line AA ′.

FIG. 2 is an IR spectrum diagram of the compound (I) of Example 1.

FIG. 3 ¹ H-NMR of polymer (2a) of Example 2.
Is a diagram showing a (CDCl _3).

FIG. 4 ¹ H-NMR of polymer (3a) of Example 3
Is a diagram showing a (CDCl _3).

[Explanation of symbols]

 1,1 'Substrate 2,2' Transparent electrode 3 Polymer liquid crystal layer 4 Spacer 5,5 'Alignment control film 6 Adhesive 7,7' Polarizer

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification number Reference number within the agency FI Technical indication location G02F 1/1333 9225-2K (72) Inventor Takeo Eguchi 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Inc.

Claims (6)

[Claims] 1. A reactive liquid crystal compound represented by the following general formula [1]. [Chemical 1] (In the formula, R ¹ represents a hydrogen atom, an alkyl group or a halogen group. U, V, W, X and Y are the same or different, and each is a single bond, —O—, —OCO— or —COO—.
Represents a represents 0 or 1. b and f are the same or different integers from 0 to 15.
c, d, and e each represent the same or different integer from 0 to 2. ) 2. A polymer liquid crystal compound having a reactive liquid crystal compound represented by the following general formula [1] as a polymerization component. [Chemical 2] (In the formula, R ¹ represents a hydrogen atom, an alkyl group or a halogen group. U, V, W, X and Y are the same or different, and each is a single bond, —O—, —OCO— or —COO—.
Represents a represents 0 or 1. b and f are the same or different integers from 0 to 15.
c, d, and e each represent the same or different integer from 0 to 2. ) 3. A nematic polymer liquid crystal compound having a reactive liquid crystal compound represented by the following general formula [1] as a polymerization component. [Chemical 3] (In the formula, R ¹ represents a hydrogen atom, an alkyl group or a halogen group. U, V, W, X and Y are the same or different, and each is a single bond, —O—, —OCO— or —COO—.
Represents a represents 0 or 1. b and f are the same or different integers from 0 to 15.
c, d, and e each represent the same or different integer from 0 to 2. ) 4. A polymer liquid crystal composition containing the polymer liquid crystal compound according to claim 2. 5. A liquid crystal device using the compound according to any one of claims 1 to 3. 6. A liquid crystal device using the polymer liquid crystal composition according to claim 4.