JPH0684357B2 - Optically active compound, liquid crystal composition containing the same, liquid crystal element having the same, display method and display device using the same - Google Patents

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel optically active compound, a liquid crystal composition containing the same, a liquid crystal device and a display device using the same, and more specifically, a novel liquid crystal having improved response characteristics to an electric field. The present invention relates to a composition, a liquid crystal display element using the same, a liquid crystal element used for a liquid crystal-optical shutter, and a display device using the liquid crystal element for display.

[0002]

2. Description of the Related Art Conventionally, liquid crystals have been applied as electro-optical elements in various fields. Most of the liquid crystal elements currently in practical use are, for example, M. Sch.
adt) and W. Helfri
ch) "Applied Physics Letters"
("Applied Physics Letter
s ") Vo.18, No.4 (1971.2.15)
P. 127-128 "Voltage Depend"
ent Optical Activity of a
Twisted Nematic liquid Cr
TN (Twisted Nem)
atic) type liquid crystal is used.

These are based on the dielectric alignment effect of liquid crystals, and utilize the effect that the average molecular axis direction is directed in a specific direction by an applied electric field due to the dielectric anisotropy of liquid crystal molecules. The optical response speed limit of these devices is said to be milliseconds, which is too slow for many applications.

On the other hand, in the application to a large flat panel display, the driving by the simple matrix system is the most effective in consideration of price, productivity and the like. The simple matrix method employs an electrode configuration in which a scan electrode group and a signal electrode group are arranged in a matrix, and in order to drive the scan electrode group, an address signal is sequentially and selectively selected and applied to the scan electrode group. Employs a time-division drive system in which a predetermined information signal is synchronized with an address signal and selectively applied in parallel.

However, when the above-mentioned TN type liquid crystal is adopted for the element of such a driving system, the scan electrode is selected and the signal electrode is not selected, or the scan electrode is not selected and the signal electrode is selected. An electric field is applied to a finite amount (so-called "half selection point").

If the difference between the voltage applied to the selection point and the voltage applied to the half selection point is sufficiently large and the voltage threshold value required to align the liquid crystal molecules perpendicularly to the electric field is set to an intermediate voltage value, The display element works normally,
When the number of scanning lines (N) is increased, the time (duty ratio) in which an effective electric field is applied to one selected point while scanning the entire screen (one frame) is reduced by 1 / N. Resulting in.

For this reason, the voltage difference as the effective value applied to the selected point and the non-selected point in the case of repeating scanning becomes smaller as the number of scanning lines increases, and as a result, the image contrast is lowered or Crosstalk is an inevitable drawback.

Such a phenomenon is caused by a liquid crystal having no bistability (a stable state in which liquid crystal molecules are aligned horizontally with respect to an electrode surface, and a vertical state only while an electric field is effectively applied). This is an essentially unavoidable problem that occurs when driving (that is, repeatedly scanning) using the temporal accumulation effect.

In order to improve this point, the voltage averaging method,
The two-frequency driving method and the multi-matrix method have already been proposed, but none of them is sufficient, and the increase in the screen size and the density of the display element is stopped because the number of scanning lines cannot be increased sufficiently. It is the current situation.

In order to improve the drawbacks of the conventional liquid crystal device, the use of a liquid crystal device having bistability is explained by Clark and Lagerwell.
11) (Japanese Patent Laid-Open No. 56-10721).
No. 6, the specification of US Pat. No. 4,367,924).

Bistable liquid crystals are generally chiral smectic C phase (SmC ^* phase) or H phase (SmH ^* phase).
A ferroelectric liquid crystal having is used.

This ferroelectric liquid crystal has a bistable state consisting of a first optical stable state and a second optical stable state with respect to an electric field, and therefore the optical modulation used in the above-mentioned TN type liquid crystal. Unlike the element, for example, the liquid crystal is oriented in the first optically stable state with respect to one electric field vector, and the liquid crystal is oriented in the second optically stable state with respect to the other electric field vector. Further, this type of liquid crystal has a property (bistability) of taking one of the two stable states described above in response to an applied electric field and maintaining that state when no electric field is applied.

In addition to the above-mentioned characteristic of having bistability, the ferroelectric liquid crystal has an excellent characteristic of high-speed response. This is because the spontaneous polarization of the ferroelectric liquid crystal and the applied electric field act directly to induce the transition of the alignment state.
It is 3 to 4 orders faster than the response speed due to the effect of the dielectric anisotropy and the electric field.

As described above, the ferroelectric liquid crystal potentially has extremely excellent characteristics, and by utilizing such characteristics, many of the problems of the conventional TN type element described above are solved. A fairly substantial improvement is obtained. In particular, it is expected to be applied to high-speed optical optical shutters and high-density, large-screen displays. For this reason, research has been conducted extensively on liquid crystal materials with ferroelectricity, but the ferroelectric liquid crystal materials developed to date have sufficient characteristics for use in liquid crystal elements, including low-temperature operating characteristics and high-speed response characteristics. It is hard to say that it has.

Between the response time τ, the magnitude Ps of spontaneous polarization and the viscosity η, the following formula [II]

[0016]

[Outside 7] (However, E is an applied electric field). Therefore, in order to increase the response speed, there are methods of (a) increasing the magnitude Ps of spontaneous polarization (b) decreasing the viscosity η (c) increasing the applied electric field E. However, the applied electric field has an upper limit because it is driven by an IC or the like, and it is desirable that the applied electric field be as low as possible. Therefore, it is actually necessary to reduce the viscosity η or increase the value of the spontaneous polarization magnitude Ps.

Generally, in a ferroelectric chiral smectic liquid crystal compound having a large spontaneous polarization, the internal electric field of the cell caused by the spontaneous polarization is also large, and there is a tendency that there are many restrictions on the device structure capable of assuming a bistable state. Further, even if the spontaneous polarization is unnecessarily increased, the viscosity tends to increase accordingly, and as a result, the response speed may not be so fast.

Further, when the temperature range used as an actual display is, for example, about 5 to 40 ° C., the response speed generally changes by about 20 times, which exceeds the limit of adjustment by the drive voltage and frequency. The current situation.

As described above, in order to put a ferroelectric liquid crystal device into practical use, it exhibits a chiral smectic phase which has a large spontaneous polarization and a low viscosity to provide a high-speed response and has a small temperature dependence of the response speed. A liquid crystal composition is required.

[0020]

SUMMARY OF THE INVENTION An object of the present invention is to make the above-mentioned ferroelectric liquid crystal device practical.
An optically active compound effective for increasing the response speed, a liquid crystal composition containing the same, particularly a liquid crystal composition exhibiting a ferroelectric chiral smectic phase, and a liquid crystal element and a display device using the liquid crystal composition are provided. To provide.

[0021]

Means for Solving the Problems and [Action] That is, the present invention is an optically active compound represented by the following general formula (I).

[0022]

[Outside 8] (R ₁ is an alkyl group or an alkoxy group having 1 to 18 carbon atoms, and R ₂ is an alkyl group having 1 to 12 carbon atoms. A is

[0023]

[Outside 9] Is. * Indicates that it is optically active. ), A liquid crystal composition containing at least one kind of the optically active compound, and a liquid crystal element and a display device in which the liquid crystal composition is disposed between a pair of electrode substrates. is there. In the compound represented by the general formula (I), R ₁ is preferably an alkyl group or an alkoxy group having 3 to 14 carbon atoms, and R ₂ is preferably an alkyl group having 4 to 8 carbon atoms. .

The compound represented by the general formula (I) of the present invention is characterized in that all three rings are bonded by a single bond. As a result, like the compound disclosed in JP-A-2-127, the electric field response is good, and the liquid crystal composition having the compound of the present invention not only has a high response speed, but also has a further temperature dependence. Effective in reducing the size.

The optically active compound represented by the general formula (I) is preferably applied by the present applicant (Japanese Patent Application No. 62-
183485 and Japanese Patent Application No. 63-37624), the optically active 3-trifluoromethyl-1-heptanoic acid of the following general formula (II), 3-trifluoromethyl-1-heptanol of the following general formula (III), and the like. Manufactured from the optically active intermediate.

[0026]

[Outside 10]

Next, an example of a general method for synthesizing the optically active compound represented by the above general formula (I) is shown below.

[0028]

[Outside 11] R ₁ , R ₂ and A are in accordance with the above general formula.

The specific structural formula of the optically active compound represented by the above general formula (I) is shown below.

[0030]

[Outside 12]

[0031]

[Outside 13]

[0032]

[Outside 14]

[0033]

[Outside 15]

[0034]

[Outside 16]

[0035]

[Outside 17]

[0036]

[Outside 18]

[0037]

[Outside 19]

[0038]

[Outside 20]

[0039]

[Outside 21]

[0040]

[Outside 22]

[0041]

[Outside 23]

The liquid crystal composition of the present invention can be obtained by mixing at least one kind of the optically active compound represented by the general formula (I) and one or more kinds of other liquid crystal compounds in an appropriate ratio.

The liquid crystal composition according to the present invention is preferably a liquid crystal composition exhibiting a chiral smectic phase.

Other liquid crystal compounds used in the present invention are represented by the following general formulas (III) to (XII).

[0045]

[Outside 24]

[0046]

[Outside 25]

[0047]

[Outside 26]

[0048]

[Outside 27]

[0049]

[Outside 28]

[0050]

[Outside 29]

[0051]

[Outside 30]

[0052]

[Outside 31]

[0053]

[Outside 32]

[0054]

[Outside 33]

[0055]

[Outside 34]

[0056]

[Outside 35]

[0057]

[Outside 36]

[0058]

[Outside 37]

[0059]

[Outside 38]

[0060]

[Outside 39]

[0061]

[Outside 40]

The proportion of the optically active compound of the present invention in the liquid crystal composition is 1 to 80% by weight, preferably 1 to 60% by weight, more preferably 1 to 40% by weight. desirable.

When two or more optically active compounds of the present invention are used, the proportion of the mixture of two or more optically active compounds of the present invention in the liquid crystal composition obtained by mixing is 1% by weight to 80%. % By weight, preferably 1% to 60% by weight,
More preferably, it is desirable to set it to 1% by weight to 40% by weight.

Further, the liquid crystal layer exhibiting the ferroelectricity in the ferroelectric liquid crystal device according to the present invention is obtained by using the liquid crystal composition exhibiting the chiral smectic phase prepared as described above in vacuum up to the temperature of the isotropic liquid. It is preferable that the liquid crystal layer is heated and sealed in an element cell and then gradually cooled to form a liquid crystal layer and returned to normal pressure.

FIG. 1 is a schematic cross-sectional view showing an example of a liquid crystal element having a chiral smectic liquid crystal layer of the present invention, for explaining the structure of a crystal element utilizing ferroelectricity.

In FIG. 1, reference numeral 1 is a chiral smectic liquid crystal layer, 2 is a glass substrate, 3 is a transparent electrode, 4 is an insulating alignment control layer, 5 is a spacer, 6 is a lead wire, 7 is a power source, 8 is a deflector plate, Reference numeral 9 indicates a light source.

The two glass substrates 2 were each provided with In ₂
A transparent electrode 3 made of a thin film of O ₃ , SnO ₂ or ITO (Indium Tin Oxide) is covered. An insulating alignment control layer 4 for arranging liquid crystals in the rubbing direction is formed on top of this by rubbing a polymer thin film such as polyimide with gauze or acetate flocking cloth. Also, as an insulating material,
For example, silicon nitride, silicon carbide containing hydrogen, silicon oxide, boron nitride, boron nitride containing hydrogen, cerium oxide, aluminum oxide, zirconium oxide, titanium oxide, magnesium fluoride, and other inorganic materials. Forming a material insulating layer, polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin, melamine resin on it. Organic insulating materials such as urea resin, acrylic resin and photoresist resin are used as the orientation control layer.
The insulating orientation control layer 4 may be formed of two layers, or may be an inorganic material insulating orientation control layer or a single organic material insulating orientation control layer. If this insulating orientation control layer is an inorganic type, it can be formed by a vapor deposition method or the like, and if it is an organic type, a solution in which an organic insulating material is dissolved or a precursor solution thereof (0.1 to 20% by weight in a solvent, preferably 0 .2 to 10% by weight) and applied by a spinner coating method, a dip coating method, a screen printing method, a spray coating method, a roll coating method or the like, and cured under predetermined curing conditions (for example, under heating) to form a film. be able to.

The layer thickness of the insulating orientation control layer 4 is usually 10Å
1 μm, preferably 10 Å to 3000 Å, more preferably 10 Å to 1000 Å are suitable.

The two glass substrates 2 are held by the spacer 5 at arbitrary intervals. For example, there is a method in which silica beads and alumina beads having a predetermined diameter are used as spacers and sandwiched between two glass substrates, and the periphery is sealed with a sealing material, for example, an epoxy adhesive material. Alternatively, a polymer film or glass fiber may be used as a spacer. A liquid crystal exhibiting ferroelectricity is enclosed between the two glass substrates.

The chiral smectic liquid crystal layer 1 in which the chiral smectic liquid crystal is enclosed is generally 0.5 to 20.
μm, preferably 1 to 5 μm.

The transparent electrode 3 is connected to an external power source 7 by a lead wire.

A polarizing plate 8 is attached to the outside of the glass substrate 2.

Since FIG. 1 is a transmission type, a light source 9 is provided.

FIG. 2 is a schematic drawing of an example of a cell for explaining the operation of a liquid crystal element utilizing ferroelectricity.
Reference numerals 21a and 21b respectively denote a substrate (glass plate) covered with a transparent electrode composed of a thin film of In ₂ O ₃ ; SnO ₂ or ITO (Indium Tin Oxide), and the liquid crystal molecular layer 22 is perpendicular to the glass surface therebetween. The liquid crystal of the SmC ^* phase or the SmH ^* phase, which is oriented so as to be formed, is enclosed. A thick line 23 represents a liquid crystal molecule, and this liquid crystal molecule 23 has a dipole moment (P⊥) 24 in a direction orthogonal to the molecule. Board 21a
When a voltage of a certain threshold value or more is applied between the electrodes on the electrodes 21 and 21b, the helical structure of the liquid crystal molecules 23 is unwound, and the orientation directions of the liquid crystal molecules 23 are changed so that all the dipole moments (P⊥) 24 are oriented in the electric field direction. be able to. Liquid crystal molecule 23
Has an elongated shape and exhibits refractive index anisotropy in the major axis direction and the minor axis direction thereof. Therefore, for example, if crossed Nicols polarizers are placed above and below the glass surface, the optical characteristics will change depending on the voltage application polarity. To become a changing liquid crystal optical modulator,
Easily understood.

The liquid crystal cell preferably used in the optical modulator of the present invention can be made sufficiently thin (for example, 10 μm or less). As shown in FIG. 3, as the liquid crystal layer becomes thinner, the helical structure of the liquid crystal molecules unwinds even when no electric field is applied, and the dipole moment Pa or Pb of the liquid crystal molecule is directed upward (34a) or downward (34b). Take either state. When an electric field Ea or Eb having a polarity different from a certain threshold value is applied to such a cell by the voltage applying means 31a and 31b as shown in FIG. 3, the dipole moment is directed upward corresponding to the electric field vector of the electric field Ea or Eb. 34a or the downward direction 34b, and the liquid crystal molecules corresponding to the first stable state 3
3a or the second stable state 33b.

As described above, there are two advantages of using such a ferroelectric liquid crystal element as an optical modulation element.

The first is that the response speed is extremely fast, and the second is that the alignment of the liquid crystal molecules has bistability. Explaining the second point further with reference to FIG. 3, for example, when the electric field Ea is applied, the liquid crystal molecules are aligned in the first stable state 33a, which is stable even when the electric field is cut off.
When an electric field Eb in the opposite direction is applied, the liquid crystal molecules are oriented in the second stable state 33b and change their orientation.
After all, it remains in this state even when the electric field is turned off. Also, unless the applied electric field Ea or Eb exceeds a certain threshold value,
Each is also maintained in the previous orientation.

By using the liquid crystal element of the present invention in the display panel section and taking the communication information synchronizing means by the data format as the image information having the scanning line address information and the SYNC signal shown in FIGS. 4 and 5, a liquid crystal display device is obtained. To realize.

In the figure, the symbols are as follows. 101 ferroelectric liquid crystal display device 102 graphic controller 103 display panel 104 scanning line driving circuit 105 information line driving circuit 106 decoder 107 scanning signal generating circuit 108 shift register 109 line memory 110 information signal generating circuit 111 driving control circuit 112 GCPU 113 host CPU 114 VRAM

The image information is generated by the graphics controller 102 on the main body side and transferred to the display panel 103 according to the signal transfer means shown in FIGS. The graphics controller 102 is a CP
U (central processing unit, hereinafter abbreviated as GCPU 112) and VRAM (memory for storing image information) 114 are used as cores for managing image information and communication between the host CPU 113 and the liquid crystal display device 101, and controlling the present invention. The method is mainly implemented on the graphics controller 102.

A light source is arranged on the back surface of the display panel.

The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples. In the following examples, all "parts" indicate "parts by weight".

[0083]

【Example】

Example 1 Production of Optically Active 2- [4- {4- (3-Trifluoromethylundecanoyloxy) phenyl} phenyl] -5-octyloxypyrimidine (Exemplified Compound 94) 2- [4- { 4- (3-trifluoromethylundecanoyloxy) phenyl} phenyl] -5
-Octyloxypyrimidine was prepared.

[0084]

[Outside 41]

0.38 g of 2- {4- (4-hydroxyphenyl) phenyl} -5-octyloxypyrimidine
(1 mmol), 0.27 g (1 mmol) of 3-trifluoromethylundecanoic acid, 0.21 g of N, N′-dicyclohexylcarbodiimide and 0.02 g of 4-pyrrolidinopyridine were dissolved in 12 ml of dichloromethane and stirred overnight at room temperature. After completion of the reaction, insoluble matter was removed by filtration,
It was purified by silica gel column chromatography (mobile phase, toluene). Further, recrystallization was performed with a mixed solvent of methanol and toluene to obtain 0.38 g of the title compound. 61% yield

[0086]

[Outside 42]

Example 2 Production of Optically Active 2- {4- (3-Trifluoromethylundecanoyloxy) phenyl} -5- (4-octyloxyphenyl) pyrimidine (Exemplified Compound 82) 2- {according to the following steps 4- (3-Trifluoromethylundecanoyloxy) phenyl} -5- (4-octyloxyphenyl) pyrimidine was prepared.

[0088]

[Outside 43] In the process shown in Example 1, 2- (4- (4-hydroxyphenyl) phenyl} -5-octyloxypyrimidine was replaced by 2- (4-hydroxyphenyl) -5.
The title compound was obtained by performing the same operation except using-(4-octyloxyphenyl) pyrimidine.
Yield 0.35 g (56% yield)

[0089]

[Outside 44]

Example 3 Production of Optically Active 2- {4- (3-Trifluoromethylnonanoyloxy) phenyl} -5- (4-octyloxyphenyl) pyrimidine (Exemplified Compound 84) It was produced according to the following steps.

[0091]

[Outside 45]

190 mg (0.84 mmo) of (+)-3-trifluoromethylnonanoic acid was placed in a 30 ml eggplant flask.
1) and 1 ml of thionyl chloride were added, and the mixture was heated at 90 ° C. for 1.5 hours. After completion of the reaction, thionyl chloride was removed by azeotropic distillation with benzene. 2 ml of dry tetrahydrofuran, 2- (4-hydroxyphenyl) -5-
(4-octyloxyphenyl) pyrimidine 263 mg
(0.70 mmol) and triethylenediamine 11
6 mg (1.1 mmol) of dry benzene solution was added. After stirring at room temperature for 30 minutes, the mixture was heated at 50 ° C. for 2 hours, again stirred at room temperature overnight, and then heated at 70 ° C. for 3 hours. After completion of the reaction, 2 ml of 3M hydrochloric acid and 10 ml of water were added, extracted with benzene, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and purification by thin layer chromatography (hexane / ethyl chloride = 3/1) was carried out to give 2- {4- (3-trifluororomethylnonanoyloxy) phenyl} -5- (4
-Octyloxyphenyl) pyrimidine yield 365 m
g (0.63mM) Yield 89.3%.

[0093]

[Outside 46]

Example 4 Production of optically active 2- [4- {4- (3-trifluoromethylnonanoyloxy) phenyl} phenyl] -5-octyloxypyrimidine (Exemplary compound 88)

[0095]

[Outside 47]

In the process shown in Example 3, 2- (4-
The title compound was obtained by performing the same operation except that 2- {4- (4-hydroxyphenyl) phenyl} -5-octyloxypyrimidine was used in place of hydroxyphenyl) -5- (4-octyloxyphenyl) pyrimidine. Obtained.

[0097]

[Outside 48]

Example 5 Optically active 2- {4- (3-trifluoromethylnonanoyloxy) phenyl} -5- (4-octylphenyl)
Production of pyrimidine (Exemplified compound 90)

[0099]

[Outside 49]

In the process shown in Example 3, 2- (4-
The title compound was obtained by performing the same operation except that 2- (4-hydroxyphenyl) -5- (4-octylphenyl) pyrimidine was used instead of hydroxyphenyl) -5- (4-octyloxyphenyl) pyrimidine. It was 69% yield

[0101]

[Outside 50]

Example 6 Production of optically active 2- {4- (3-trifluoromethylheptanoyloxy) phenyl} -5- (4-octyloxyphenyl) pyrimidine (Exemplary compound 85)

[0103]

[Outside 51]

The title compound was obtained by the same procedure as in Example 3 except that 3-trifluoromethylheptanoic acid was used instead of 3-trifluoromethylnonanoic acid. Yield 34%

[0105]

[Outside 52]

Example 7 Production of Optically Active 2- {4- (3-Trifluoromethylnonyloxy) phenyl} -5- (4-octyloxyphenyl) pyrimidine (Exemplified Compound 83) It was produced according to the following steps.

[0107]

[Outside 53]

Step 1 (+)-3-trifluoromethyl-1-nonanol 55
0 mg (2.6 mmol), pyridine 790 mg (10
P-toluenesulfonic acid chloride (500 mg, 2.62 mmol) was added to the mixture at room temperature.
Stir for hours. After completion of the reaction, the mixture was neutralized with 2M hydrochloric acid, extracted with methylene chloride, and 820 mg of 3-
Trifluoromethylnonyl tosylate was obtained.

Step 2 In a 30 ml round-bottomed flask, 0.188 g (0.50 mM) of 2- (4-hydroxyphenyl) -5- (4-octyloxyphenyl) pyrimidine was dissolved in dry tetrahydrofuran, and dry dimethylformamide 2
ml was added and stirred well. 60% sodium hydride 40
mg, and then (-)-3-trifluoromethylnonyl P-toluenesulfonate 0.183 g (0.5
(0 mM) was added dropwise, and the mixture was reacted at 130 ° C. for 6 hours. After adding distilled water, the mixture was extracted with ether and dried over anhydrous sodium sulfate. Purified by thin layer chromatography (developing solvent 1st time hexane: ethyl acetate = 3: 1, 2nd time hexane: ethyl acetate = 4: 1), 2- {4- (3-trifluoromethylnonyloxy) phenyl}- Yield of 5- (4-octyloxyphenyl) pyrimidine 0.13 g
(0.23 mM) with a yield of 46.0%.

[0110]

[Outside 54]

Example 8 Production of Optically Active 2- [4- {4- (3-Trifluoromethylnonyloxy) phenyl} phenyl] -5-octyloxypyrimidine (Exemplary Compound 39)

[0112]

[Outside 55]

In the process shown in Example 7, 2- (4-
The title compound was obtained by performing the same operation except that 2- {4- (4-hydroxyphenyl) phenyl} -5-octyloxypyrimidine was used in place of hydroxyphenyl) -5- (4-octyloxyphenyl) pyrimidine. Obtained. 24% yield

[0114]

[Outside 56]

Example 9 The following compounds were mixed in the following parts by weight to prepare a liquid crystal composition A.

[0116]

[Outside 57]

Further, the liquid crystal composition B was mixed with the exemplified compound 94 in the following parts by weight.
It was created.

[0118]

[Outside 58]

Example 10 Two 0.7 mm thick glass plates were prepared, an ITO film was formed on each glass plate, and voltage application electrodes were prepared.
Further, SiO ₂ was vapor-deposited on this to form an insulating layer. Silane coupling agent on glass plate [KB manufactured by Shin-Etsu Chemical Co., Ltd.
M-602] 0.2% isopropyl alcohol solution was rotated at a rotation speed of 2000 r. p. Apply for 15 seconds at m speed,
A surface treatment was applied. After that, a heat drying treatment was performed at 120 ° C. for 20 minutes.

Further, a polyimide resin precursor [Toray Industries, Inc. SP-
510] 1.5% dimethylacetamide solution was rotated at a rotation speed of 2000 r.p.m. p. m spinner for 15 seconds.
After the film formation, a heat condensation baking treatment was performed at 300 ° C. for 60 minutes. At this time, the film thickness of the coating film was about 250Å.

The film after firing was rubbed with an acetate flocked cloth, washed with an isopropyl alcohol solution, sprayed with alumina beads having an average particle diameter of 2 μm on one glass plate, and then rubbed. The axes were made parallel to each other, the glass plates were bonded together using an adhesive sealant [Rixon Bond (Chisso Corporation)], and dried by heating at 100 ° C. for 60 minutes to prepare a cell.

The liquid crystal composition B mixed in Example 9 was injected into this cell in an isotropic liquid state and gradually cooled from the isotropic phase to 25 ° C. at 20 ° C./h to obtain a ferroelectric liquid crystal element. Created. When the cell thickness of this cell was measured with a Beret phase plate, it was about 2 μm.

Using this ferroelectric liquid crystal device, the magnitude Ps of spontaneous polarization and the peak-to-peak voltage Vpp = 20.
The response speed (hereinafter referred to as optical response speed) was measured by detecting the optical response (change in transmitted light amount 0 to 90%) under the crossed Nicols by applying the voltage V. The results are shown below.

[0124]

[Outside 59]

Example 11 Exemplified compound 8 synthesized in Example 3 for liquid crystal composition A
4 was mixed in the following parts by weight to prepare a liquid crystal composition C.

[0126]

[Outside 60]

Example 1 except that the liquid crystal composition C was used.
A ferroelectric liquid crystal device was prepared in the same manner as in Example 0, and Example 1
The magnitude Ps of spontaneous polarization and the optical response speed were measured in the same manner as in Example 0. The measurement results are shown below.

[0128]

[Outside 61]

Example 12 Exemplified compound 8 synthesized in Example 4 for liquid crystal composition A
8 was mixed in the following parts by weight to prepare a liquid crystal composition D.

[0130]

[Outside 62]

Example 1 except that the liquid crystal composition D was used.
A ferroelectric liquid crystal device was prepared in the same manner as in Example 0, and Example 1
The magnitude Ps of spontaneous polarization and the optical response speed were measured in the same manner as in Example 0. The measurement results are shown below.

[0132]

[Outside 63]

Example 13 Exemplified compound 9 synthesized in Example 5 for liquid crystal composition A
0 was mixed in the following parts by weight to prepare a liquid crystal composition E.

[0134]

[Outside 64]

Example 1 except that the liquid crystal composition E was used.
A ferroelectric liquid crystal device was prepared in the same manner as in Example 0, and Example 1
The magnitude Ps of spontaneous polarization and the optical response speed were measured in the same manner as in Example 0. The measurement results are shown below.

[0136]

[Outside 65]

Comparative Example 1 A liquid crystal composition F was prepared by mixing the following compounds with the liquid crystal composition A in the following parts by weight.

[0138]

[Outside 66]

Example 1 except that the liquid crystal composition F was used.
A ferroelectric liquid crystal device was prepared in the same manner as in Example 0, and Example 1
The magnitude Ps of spontaneous polarization and the optical response speed were measured in the same manner as in Example 0. The measurement results are shown below.

[0140]

[Outside 67]

As is apparent from Comparative Example 1 and Examples 10 to 13, all three rings in the mesogenic skeleton of the present invention are bonded with a single bond, as compared with a liquid crystal composition containing a compound having an ester in the mesogenic skeleton. It can be seen that the liquid crystal composition containing the compound has a faster response speed and a smaller temperature dependence of the response speed.

[0142]

If the compound of the present invention exhibits a chiral smectic phase by itself, it becomes a material that can be effectively applied to a device utilizing ferroelectricity. Further, when the liquid crystal composition having the compound of the present invention exhibits a chiral smectic phase,
A device containing the liquid crystal composition can be operated by utilizing the ferroelectricity of the liquid crystal composition. Ferroelectric liquid crystal elements that can be used in this manner can be liquid crystal elements having good switching characteristics and improved low-temperature operating characteristics, and liquid crystal elements having reduced temperature dependence of response speed.

A display device in which the liquid crystal device of the present invention is used as a display device in combination with a light source, a drive circuit, etc. is a good device.

[Brief description of drawings]

FIG. 1 is a schematic cross-sectional view of an example of a liquid crystal element using a liquid crystal exhibiting a chiral smectic phase.

FIG. 2 is a perspective view schematically showing an example of an element cell for explaining the operation of a liquid crystal element utilizing the ferroelectricity of liquid crystal.

FIG. 3 is a perspective view schematically showing an example of an element cell for explaining the operation of a liquid crystal element utilizing the ferroelectricity of liquid crystal.

FIG. 4 is a block diagram showing a liquid crystal display device having a liquid crystal element utilizing ferroelectricity and a graphics controller.

FIG. 5 is a timing chart of image information communication between the liquid crystal display device and the graphics controller.

[Explanation of symbols]

 1 Liquid crystal layer having a chiral smectic phase 2 Glass substrate 3 Transparent electrode 4 Insulating orientation control layer 5 Spacer 6 Lead wire 7 Power source 8 Polarizing plate 9 Light source Io Incident light I Transmitted light 21a Substrate 21b Substrate 22 Having chiral smectic phase Liquid crystal layer 23 Liquid crystal molecule 24 Dipole moment (P⊥) 31a Voltage applying means 31b Voltage applying means 33a First stable state 33b Second stable state 34a Upward dipole moment 34b Downward dipole moment Ea Upward electric field Eb Downward electric field 101 Ferroelectric liquid crystal display device 102 Graphics controller 103 Display panel 104 Scan line drive circuit 105 Information line drive circuit 106 Decoder 107 Scan signal generation circuit 108 Shift register 109 Line memory 110 Information signal generation circuit 11 Drive control circuit 112 GCPU 113 host CPU 114 VRAM

Continuation of the front page (51) Int.Cl. ⁵ Identification number Reference number within the office FI Technical indication location G09F 9/35 305 7610-5G 335 7610-5G (72) Inventor Takao Takiguchi 3-30 Shimomaruko, Ota-ku, Tokyo No. 2 in Canon Inc. (72) Inventor Takashi Iwaki 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Inc. (72) Inventor Goji Kadano 3-30-2 Shimomaruko, Ota-ku, Tokyo Canon Within the corporation

Claims (30)

[Claims] 1. The following general formula (I): (R ₁ is an alkyl group or an alkoxy group having 1 to 18 carbon atoms, R ₂ is an alkyl group having 1 to 12 carbon atoms. A is Is. * Indicates that it is optically active. ) An optically active compound represented by: 2. The optically active compound represented by the general formula (I), wherein R ₁ is an alkyl group or an alkoxy group having 3 to 14 carbon atoms, and R ₂ is an alkyl group having 4 to 8 carbon atoms. The optically active compound according to claim 1. 3. The optically active compound according to claim 1, wherein the compound of the general formula (I) is a compound having a liquid crystal phase. 4. The optically active compound according to claim 1, wherein the compound of the general formula (I) is a compound exhibiting a chiral smectic phase. 5. A liquid crystal composition comprising at least one kind of the optically active compound according to claim 1. 6. The liquid crystal composition according to claim 5, wherein the optically active compound represented by formula (I) is contained in an amount of 1 to 80% by weight based on the liquid crystal composition. 7. The liquid crystal composition according to claim 5, which contains the optically active compound represented by the general formula (I) in an amount of 1 to 60% by weight based on the liquid crystal composition. 8. The liquid crystal composition according to claim 5, wherein the optically active compound represented by the general formula (I) is contained in an amount of 1 to 40% by weight based on the liquid crystal composition. 9. The liquid crystal composition according to claim 5, wherein the liquid crystal composition has a chiral smectic phase. 10. A liquid crystal device comprising the liquid crystal composition according to claim 5 disposed between a pair of electrode substrates. 11. The liquid crystal device according to claim 10, further comprising an alignment control layer provided on the electrode substrate. 12. The liquid crystal device according to claim 11, wherein the alignment control layer is a layer subjected to a rubbing treatment. 13. The liquid crystal device according to claim 10, wherein the pair of electrode substrates are arranged with a film thickness in which the spiral of liquid crystal molecules is released. 14. A display device comprising the liquid crystal element according to claim 10. 15. The display device according to claim 14, further comprising a drive circuit for the liquid crystal element. 16. The display device according to claim 15, further comprising a light source. 17. A display method using a liquid crystal composition containing at least one kind of an optically active compound represented by the following general formula (I). [Outside 3] (R ₁ is an alkyl group or an alkoxy group having 1 to 18 carbon atoms, R ₂ is an alkyl group having 1 to 12 carbon atoms. A is Is. * Indicates that it is optically active. ) 18. The optically active compound represented by the general formula (I), wherein R ₁ is an alkyl group or an alkoxy group having 3 to 14 carbon atoms, and R ₂ is an alkyl group having 4 to 8 carbon atoms. 18. The display method according to claim 17, which is provided. 19. The display method according to claim 17, wherein the compound of the general formula (I) is a compound having a liquid crystal phase. 20. The display method according to claim 17, wherein the compound of the general formula (I) is a compound exhibiting a chiral smectic phase. 21. The display method according to claim 17, wherein the optically active compound represented by the general formula (I) is contained in an amount of 1 to 80% by weight based on the liquid crystal composition. 22. The display method according to claim 17, wherein the optically active compound represented by the general formula (I) is contained in an amount of 1 to 60% by weight based on the liquid crystal composition. 23. The display method according to claim 17, wherein the optically active compound represented by the general formula (I) is contained in an amount of 1 to 40% by weight based on the liquid crystal composition. 24. The display method according to claim 17, wherein the liquid crystal composition has a chiral smectic phase. 25. The display method according to claim 17, wherein display is performed by electrically driving the liquid crystal composition. 26. A display method using a liquid crystal element in which a liquid crystal composition containing at least one liquid crystal compound represented by the following general formula (I) is arranged between a pair of electrode substrates. [Outside 5] (R ₁ is an alkyl group or alkoxy group having 1 to 18 carbon atoms, R ₂ is an alkyl group having 1 to 12 carbon atoms. A is Is. * Indicates that it is optically active. ) 27. The display method according to claim 26, further comprising an alignment control layer provided on the electrode substrate. 28. The display method according to claim 27, wherein the orientation control layer is a layer subjected to a rubbing treatment. 29. The display method according to claim 26, wherein the pair of electrode substrates are arranged with a film thickness in which the spiral of liquid crystal molecules is released. 30. The display method according to claim 26, wherein display is performed by electrically driving the liquid crystal composition.