JPH02272088A - Liquid crystal composition and liquid crystal element containing the same - Google Patents

Abstract

PURPOSE:To provide the subject novel composition containing a liquid crystal compound having a specific structure, exhibiting quick response, having decreased temperature dependency of the response speed and useful as a liquid crystal display element, a liquid crystal optical shutter, etc. CONSTITUTION:The objective composition contains a crystalline compound of formula I [R1 and R2 are (substituted) 1-16C alkyl; X1 is single bond or -O-: X2 is single bond, group of formula II, etc.; A is cis-1,4-cyclohexylene; Y is group of formula II, -CH2O-, etc.; A' is -A1- or -A1-A2- (A1 and A2 are group of formula III, IV, etc.)]. The composition is preferably compounded with a liquid crystal compound of formula V, etc., in combination with the crystalline compound of formula I. The amount of the compound of formula I is preferably 1-500 pts.wt. per 100 pts.wt. of the above liquid crystal composition.

Description

[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a liquid crystal composition used for liquid crystal elements used in liquid crystal display elements, liquid crystal-light shutters, etc. More specifically, the present invention relates to a liquid crystal composition that has improved response characteristics to an electric field. , all related to novel liquid crystal compositions.

[Conventional technology]

Conventionally, liquid crystals have been applied as electro-optical elements in various fields. Most of the liquid crystal elements that are currently in practical use are described in "Applied Physics Letters" by M. Schatt and W. Helfrich, for example.
ysics Letters'') Vo, 18. N
o, 4 (1971°2.15) P, 127-128
“Voltage Dependent Optica
l AeHvity of a Twisted
This uses a TN (Twisted Nematic) type liquid crystal shown in Nematic Liquid Crystal.

These are based on the dielectric alignment effect of liquid crystals, and due to the dielectric anisotropy of liquid crystal molecules, the average molecular ring direction is oriented in a specific direction by an applied electric field. It is said that the limit of the optical response speed of an element is milliseconds, which is too slow for many applications.On the other hand, for applications in large flat displays, considering cost, productivity, etc., a simple matrix method is recommended. In the simple matrix method, an electrode configuration in which scanning electrode groups and signal electrode groups are arranged in a matrix is adopted, and in order to drive the scanning electrode group, an address signal is sent periodically to the scanning electrode group. A time division driving method is adopted in which a predetermined information signal is selectively applied in parallel to the signal electrode group in synchronization with an address signal.

However, if the above-mentioned TN type liquid crystal is adopted as an element of such a driving method, there will be an area where the scanning electrode is selected and the signal electrode is not selected, or an area where the scanning electrode is not selected and the signal electrode is selected (so-called A finite electric field is also applied to the “half-selected point”.

If the difference between the voltage applied to the selected point and the voltage applied to the half-selected point is sufficiently large, and the voltage threshold required to align the liquid crystal molecules perpendicular to the electric field is set to an intermediate voltage value,
Although the display element operates normally, the number of scanning lines (N
), the time during which an effective electric field is applied to one selected point (duty ratio) while scanning the entire screen (one frame) decreases by 1/N.

For this reason, when repeated scanning is performed, the effective voltage difference between selected points and non-selected points becomes smaller as the number of scanning lines increases (resulting in lower image contrast and crosstalk). This is an unavoidable drawback.

This phenomenon is caused by liquid crystals that do not have bistability (the stable state is when the liquid crystal molecules are aligned horizontally with respect to the electrode surface, and they are aligned vertically only while an electric field is effectively applied). )
This is essentially an unavoidable problem that arises when driving using the temporal accumulation effect (that is, repeatedly scanning).

In order to improve this point, voltage averaging method, dual frequency driving method, multiple matrix method, etc. have already been proposed, but all of these methods are insufficient, and it is necessary to increase the screen size and density of display elements. Currently, the number of scanning lines has reached a plateau due to the inability to increase the number of scanning lines sufficiently.

To improve the drawbacks of conventional liquid crystal devices, the use of bistable liquid crystal devices has been proposed by Clark (C1a
rk) and Lagerwall (Japanese Unexamined Patent Publication No. 56-107216, US Pat. No. 4,367.924, etc.).

As the bistable liquid crystal, a ferroelectric liquid crystal having a chiral smectic C phase (SmC* phase) or H phase (S m H* phase) is generally used.

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

In addition to the above-mentioned feature of bistability, ferroelectric liquid crystals have the excellent feature of high-speed response. This is because the spontaneous polarization of the ferroelectric liquid crystal and the applied electric field directly act to induce a transition in the orientation state, which is 3 to 4 orders of magnitude faster than the response speed due to the effect of the dielectric anisotropy and the electric field.

In this way, ferroelectric liquid crystals potentially have extremely excellent properties, and by utilizing these properties, many of the problems of the conventional TN type elements mentioned above can be overcome. In particular, it is expected to be applied to high-speed optical shutters and high-density, large-screen displays.

For this reason, extensive research has been conducted on liquid crystal materials with ferroelectric properties, but the ferroelectric liquid crystal materials developed to date have sufficient characteristics for use in liquid crystal devices, including low-temperature operation characteristics and high-speed response. It is hard to say that it is equipped with the following.

The following equation exists between the response time τ, the magnitude of spontaneous polarization Ps, and the viscosity η: [nl η τ=[■]5−E (where E is the applied electric field). Therefore, to increase the response speed, (
There is a method of (a) increasing the magnitude of spontaneous polarization Ps, (b) decreasing the viscosity η, and (ii) increasing the applied electric field E. The applied electric field has an upper limit because it is driven by an IC or the like, and it is desirable that it be as low as possible.

Therefore, it is actually necessary to reduce the viscosity η or increase the value of the spontaneous polarization Ps.

In general, in ferroelectric chiral smectic liquid crystal compounds with large spontaneous polarization, the internal electric field of the cell caused by the spontaneous polarization is large, and there tends to be more restrictions on device configurations that can take a bistable state.

Furthermore, even if the spontaneous polarization is unnecessarily increased, the viscosity tends to increase accordingly, and as a result, it is conceivable that the response speed will not become very fast.

Furthermore, if the actual operating temperature range for a display is, for example, 5 to 40 degrees Celsius, the response speed will generally vary by a factor of 20, which is currently beyond the limits of adjustment by drive voltage and frequency. be.

As mentioned above, in order to put ferroelectric liquid crystal elements into practical use, a ferroelectric chiral smectic liquid crystal composition that has low viscosity (high speed response) and small temperature dependence of response speed is required. Ru.

(Problems to be Solved by the Invention) An object of the present invention is to create a liquid crystal composition that has a high response speed (and also reduces the temperature dependence of the response speed) in order to make a ferroelectric liquid crystal element practical. The object of the present invention is to provide a liquid crystal composition, particularly a ferroelectric chiral smectic liquid crystal composition, and a liquid crystal element using the liquid crystal composition.

[Means for Solving the Problem] and [Operation] That is, the first invention of the present invention has the following general formula (1) % formula % [] (wherein R1 and R2 each have a substituent) is an optional alkyl group having 1 to 16 carbon atoms, Xl represents a single bond or 10-, and X2 is a hydrogen atom, F, C1, Br, CH3, CN or CF.
3, and Z represents 10- or -8-. ) The present invention relates to a ferroelectric chiral smectic liquid crystal composition containing at least one type of liquid crystal compound represented by the following.

A second invention relates to a liquid crystal element using the liquid crystal composition, specifically a ferroelectric liquid crystal element in which the liquid crystal composition is disposed between a pair of electrode substrates.

is -A1- or -A, -A2-, and has the general formula (I)
In the liquid crystal compound represented by, Xl is preferably a single bond, X2 is preferably a single bond, and when -A'- is one, to one is selected from the following (i) to (iv). It will be done.

(i) ct to C16 n-alkyl group, more preferably C8 to C14 n-alkyl group -8-A, - when A2 - is preferably , then X2 is preferably a single bond, -0 - (However, m is an integer of 1 to 6, and n is an integer of 2 to 8. Also, it may be optically active.) (However, r is an integer of θ to
It is an integer of 6, and S is 0 or 1. Also, t is 1
~12 integer.

Moreover, it may be optically active. ) (iv) CH2CHCx H2! +1* The present inventors have achieved high-speed response by using the above liquid crystal composition and a liquid crystal element using the same.

It has been discovered that the display characteristics can be improved by reducing the temperature dependence of the response speed, and that good display characteristics can be obtained.

The present invention will be explained in detail below.

Examples of specific structural formulas of the liquid crystalline compound represented by the general formula (I) are shown below.

(However, X is an integer from 1 to 14.) CH3 H3 CH3 CH3 C) i3 CH.

CI■3 U H3 The ferroelectric chiral smectic liquid crystal composition of the present invention contains at least one liquid crystalline compound represented by the general formula (1) above.
It can be obtained by mixing the seeds and one or more other liquid crystal compounds in appropriate proportions.

Specific examples of other liquid crystal compounds used in the present invention are listed below.

Compound no.

H3 C1-1゜ CH3 CH8 CH3 CH3 H3 CH3 CH3 vinegar CH3 CH.

CH3 C) I 3 H3 CH9 H3 H3 H3 CH3 CH.

CH3 Bone CH3 CtoH21o-@-+CH2)g Cosha OCR, C
H.O.C., H.

11* CH.

CH.

CH8 CH.

CH3 (ios) vinegar l Ci! I I e C! r r vinegar CF3 CF3 vinegar CF3 CF3 C.F.

N N N N N c , H, (4 units C6HI3 C7°H210 units CH, O units QC, H pupils) Furthermore, the following trans-cyfurohexane derivatives can be used as other liquid crystalline compounds. .

Liquid crystal compound of the present invention and one or more other liquid crystal compounds,
Alternatively, the blending ratio with a liquid crystal composition containing it (these may be ferroelectric liquid crystal compounds and ferroelectric liquid crystal compositions. Hereinafter, these are abbreviated as ferroelectric liquid crystal materials) is ferroelectric. The amount of the liquid crystalline compound according to the present invention is preferably 1 to 500 parts by weight per 100 parts by weight of the liquid crystal material.

Furthermore, when two or more liquid crystal compounds of the present invention are used, the blending ratio with the ferroelectric liquid crystal material is such that the mixture of two or more liquid crystal compounds of the present invention is mixed with the ferroelectric liquid crystal material per 100 parts by weight of the ferroelectric liquid crystal material described above. The amount is preferably 1 to 500 parts by weight.

FIG. 1 is a schematic cross-sectional view of an example of a liquid crystal element having a ferroelectric liquid crystal layer according to the present invention, for explaining the structure of the ferroelectric liquid crystal element.

In FIG. 1, the symbol l is a ferroelectric 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 polarizing plate, 9 indicates a light source.

The two glass substrates 2 are each made of In2O3゜SnO.
2 or ITO (Indium-Tin Oxid
A transparent electrode made of a thin film such as e) is coated. On top of this, a thin film of a polymer such as polyimide is rubbed with gauze or acetate flocked cloth to form an insulating alignment control layer that aligns the liquid crystals in the rubbing direction. Insulating materials such as silicon nitride, hydrogen-containing silicon carbide, silicon oxide, boron nitride, hydrogen-containing boron nitride, cerium oxide, aluminum oxide, zirconium oxide, titanium oxide, and fluoride An inorganic insulating layer such as magnesium is formed, and then polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyvaraxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin , an organic insulating material such as melamine resin, Yulia resin, acrylic resin or photoresist resin as an orientation control layer.
The insulating orientation control layer may be formed of two layers (or may be a single layer of an insulating orientation control layer of an inorganic material or an insulating orientation control layer of an organic material. If it is organic, it can be formed by a vapor deposition method, etc., and if it is organic, it can be formed by a solution in which an organic insulating material is dissolved or its precursor solution (0.1 to 20% by weight, preferably 0.2 to 10% by weight in a solvent).
) using a spinner coating method, dip coating method, screen printing method, spray coating method, roll coating method, etc.
It can be cured and formed under predetermined curing conditions (for example, under heating).

The thickness of the insulating orientation control layer is usually 30 to 1 μm, preferably 30 to 3000, more preferably 50 to 1 μm.
000 people are being treated.

These two glass substrates 2 are kept at an arbitrary distance by a spacer 5. For example, using silica beads or alumina beads with a predetermined diameter as spacers, the glass substrate 2
There is a method in which the substrate is held between two sheets and the periphery is sealed using a sealing material such as an epoxy adhesive. In addition, a polymer film or glass fiber may be used as a spacer.

A ferroelectric liquid crystal is sealed between these two glass substrates.

The ferroelectric liquid crystal layer in which the ferroelectric liquid crystal is sealed is generally 0.5 to 20 μm, preferably 1 to 5 μm.

Further, it is desirable that this ferroelectric liquid crystal has an SmCmC phase inversion irradial smectic phase in a wide temperature range including room temperature (particularly on the low temperature side) and has high-speed response. Furthermore, it is desired that the temperature dependence of the response speed be small and that the driving voltage margin be wide.

In addition, especially when used as an element, in order to exhibit good homogeneous orientation and obtain a monodomain state, the ferroelectric liquid crystal has to be changed from the tokiyoshi phase to the ch phase (cholesteric phase) to the SmA phase (smectic phase) -8mC*. It is desirable to have a phase transition series called phase (chiral smectic C phase).

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

Further, a polarizing plate 8 is bonded to the outside of the glass substrate 2.

The device shown in FIG. 1 is of a transmission type, so it is equipped with a light source 9.

FIG. 2 schematically depicts an example of a cell for explaining the operation of a ferroelectric liquid crystal element. 21a and 21b are In203, SnO2 or ITO (fn
A substrate (glass plate) coated with a transparent electrode made of a thin film such as dium-Tin Oxide), between which a liquid crystal of SmC* phase or SmH* phase is oriented so that the liquid crystal molecular layer 22 is perpendicular to the glass surface. It 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 perpendicular to the molecule. When a voltage higher than a certain threshold is applied between the electrodes on the substrates 21a and 21b, the helical structure of the liquid crystal molecules 23 is unraveled, and the dipole moment (P±)
24 are all oriented in the direction of the electric field (so that the liquid crystal molecules 23 can change the orientation direction. The liquid crystal molecules 23 have an elongated shape and exhibit refractive index anisotropy in the long axis direction and the short axis direction, Therefore, it is easy to understand that, for example, if cross-niffle polarizers are placed above and below a glass surface, a liquid crystal optical modulation element whose optical characteristics change depending on the polarity of applied voltage can be obtained.

The liquid crystal cell preferably used in the optical modulation element of the present invention can have a sufficiently thin thickness (for example, 10 μm or less). As the liquid crystal layer becomes thinner in this way, the helical structure of the liquid crystal molecules unwinds even when no electric field is applied, as shown in Figure 3, and the dipole moment Pa or pb is directed upward (34a) or downward (34b). ). Such a cell 1. ,, an electric field Ea or Eb of different polarity above a certain threshold as shown in FIG.
is applied by the voltage applying means 31a and 31b, the dipole moment changes its direction to upward direction 34a or downward direction 34b corresponding to the electric field vector of electric field Ea or Eb, and accordingly, the liquid crystal molecules change from the first stable state 33a to the downward direction 34b. Alternatively, it is oriented in one of the second stable states 33b.

As mentioned above, there are two advantages to using such ferroelectricity as an optical modulation element.

The first is that the response speed is extremely fast, and the second is that the alignment of liquid crystal molecules has bistability. To further explain the second point with reference to FIG. 3, for example, when the electric field Ea is applied, the liquid crystal molecules are oriented in a first stable state 33a, and this state remains stable even when the electric field is turned off. Moreover, when an electric field Eb in the opposite direction is applied, the liquid crystal molecules enter the second stable state 3.
3b and changes the orientation of the molecule, but it remains in this state even after the electric field is turned off. Further, as long as the applied electric field Ea or Eb does not exceed a certain threshold value, the previous orientation state is maintained.

EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples.

Example 1 Cis-4-pentyl dichlorohexanecarboxylic acid 4-(5
-Synthesis of undecyl-2-pyrimidinyl)phenyl (exemplified compound No. 1-6) 3.29 g (10.1 mmole) of 4-(5-undecyl-2-pyrimidinyl)phenol and cis-4-pentylcyclohexanecarboxylic acid (Kanto Dissolve 2.00 g (10.1 mmole) of a chemical product (cis content 67.3%) in 100 mf of dichloromethane, and add N, N' under stirring at room temperature.
-dicyclohexylcarbodiimide 2.08g (10
, 1 mmole).

0.015 g of 4-pyrrolidinopyridine was successively added, followed by stirring at room temperature overnight. N precipitates after the reaction is completed,
N'-dicyclohexylurea was filtered off, and the filtrate was dried under reduced pressure. The residue was purified by silica gel column chromatography using benzene as a developing solvent, and then recrystallized from ethanol to obtain cis-4-pentylcyclohexanecarboxylic acid 4-
(5-undecyl-2-pyrimidyl)l phenyl 0.8
1 g (yield 15.8%) was obtained.

Phase transition temperature Cryst, lso, ('C)6
3.4 Example 2 Cis-4-pentylcyclohexanecarboxylic acid 4-(2
'-Fluorooctyloxy)phenyl (Exemplary Compound N
o,! -8) Synthesis of 4-(2'-fluorooctyloxy)phenol o,
50 g (2,08 mmole) and cis-4-pentylcyclohexanecarboxylic acid (I67 containing cis monomer, manufactured by Kanto Kagaku Co., Ltd.)
．． 3%) 0.42 g (2,12 mmole) was dissolved in 30 ml of dichloromethane, and 0.44 g (2,13
mmole) and 0.05 g of 4-pyrrolidinol pyridine were sequentially added, followed by stirring at room temperature for 5 hours. After the reaction is completed, the precipitated N,N'-dicyclohexylurea is filtered off, and the filtrate is dried under reduced pressure. The residue was purified by silica gel column chromatography using toluene as a developing solvent to obtain 0.19 g of 4-(2'fluorooctyloxy)phenyl cis-4pentylcyclohexanecarboxylate (yield 21.7%).

Phase transition temperature Example 3 Cis-4-pentylcyclohexanecarboxylic acid 2°3-
Dicyano-4-hexyloxyphenyl (Exemplary Compound N
Synthesis of 2.3-dicyano-4-hexyloxyphenol 0.
50 g (2,05 mmole) was dissolved in a mixed solvent of 4 ml of dichloromethane and 20 mf of tetrahydrofuran, and 0.41 g (2,05 mmole) of cis-4-pentyl-cyclohexanecarboxylic acid, N, N'-
Dicyclohexylcarbodiimide 0.42 g (2,
06m mole), 4-pyrrolidinopyridine 0.0
5 g was added and stirred at room temperature overnight. After completion of the reaction, the precipitated N,N'-dicyclohekidylinol was filtered off, and the filtrate was dried under reduced pressure. The residue was purified by silica gel column chromatography using benzene as a developing solvent, and recrystallized from ethanol to obtain cis-4-pentylcyclohexanecarboxylic acid 2.
,3-dicyano-4-hexyloxyphenyl 0.37
g (yield 42.5%) was obtained.

Phase transition temperature Example 4 The following exemplified compounds were mixed in the following parts by weight to form a liquid crystal composition A.
It was created.

Exemplified Compound No. Structural Formula Parts by Weight F Furthermore, the following exemplary compounds were mixed with the liquid crystal composition A in the weight parts shown below to prepare a liquid crystal composition B.

Exemplary Compound No. Structural Formula Weight Part Next, two 0.7 mm thick glass plates were prepared, an lT10 film was formed on each glass plate, a voltage application electrode was created, and SiO2 was vapor-deposited to form an insulating layer. A silane coupling agent [KBM-602 manufactured by Shin-Etsu Chemical ■] 0.2% isopropyl alcohol solution was placed on a glass plate using a spinner with a rotation speed of 2000 r, p, m for 15 minutes.
It was applied for a few seconds and surface treated.

Thereafter, a heat drying treatment was performed at 120° C. for 20 minutes.

Furthermore, 1.5% polyimide resin precursor [Toshi ■ 5P-510] was applied on a glass plate with an ITO film that was surface-treated.
The dimethylacetamide solution was rotated at 200 Or, p, m.
After forming the film 3, which was applied for 15 seconds using a spinner, a heating condensation baking process was performed at 300° C. for 60 minutes. The thickness of the coating film at this time was approximately 250.

After firing, the film was rubbed with acetate flocked cloth, then washed with isopropropylene and bil alcohol, and alumina beads with an average particle size of 2 μm were sprinkled on one glass plate, and each rubbed axis so that they are parallel to each other, and apply adhesive sealant [Rixon Pond (
Glass plates were glued together using Nisso (Japanese) and dried by heating at 100° C. for 60 minutes to create a cell. The cell thickness of this cell was measured using a Bereck phase plate and was approximately 2μ.
It was m.

By injecting liquid crystal composition B in an isotropic liquid state into this cell and slowly cooling it from the Tokichi phase to 25°C at a rate of 20°C/h,
A ferroelectric liquid crystal device was created.

Using this ferroelectric liquid crystal element, the optical response (transmitted light amount change 0~90%) under crossed Nicols is detected by applying a voltage of peak-to-peak voltage Vpp = 20V, and the response speed (hereinafter referred to as optical response) is detected. speed) was measured. The results are shown below.

15℃ 25℃ 35℃ Response speed 119 μsec 81 μsec
67 μsec Comparative Example 1 A ferroelectric liquid crystal element was prepared in the same manner as in Example 4 except that the liquid crystal composition A mixed in Example 4 was injected into the cell, and the optical response speed was measured.

The results are shown below.

15℃ 26℃ 35℃Response speed 155 μSec 1004. sec
80 μsec Example 5 Exemplary compound 1-2 used in Example 4. 1-6゜1-
In place of No. 55, the following exemplified compounds were mixed in the weight parts shown below to prepare a liquid crystal composition C.

Exemplified Compound No. Structural Formula 1 part Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was determined in the same manner as in Example 4. It was measured.

The measurement results are shown below.

15°C 25°C 35°C Response speed 122 μ5ec 78μ5ec 64μsec Example 6 Exemplary compound used in Example 4! -2,1-6゜1-5
In place of No. 5, the following exemplified compounds were mixed in the weight parts shown below to prepare a liquid crystal composition.

Exemplified Compound No. Structure 2 parts 1 part Ferroelectric liquid crystal elements were prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was determined in the same manner as in Example 4. It was measured.

The measurement results are shown below.

15°C 25°C 35°C Response speed 117μ5ec 76μ5ec 63μsec Example 7 Exemplary compound 1-2 used in Example 4. 1-6゜1-
In place of No. 55, the following exemplary compounds were mixed in the weight parts shown below to prepare liquid crystal composition E.

Exemplary Compound NO8 Structural Formula Part by weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 4. .

The measurement results are shown below.

15°C 25°C 35°C Response speed 1.04 p 5ec 71μ5ec 57μC Example 8 Exemplary compound 1-2 used in Example 4. 1-61-5
Liquid crystal composition F was prepared by mixing the following exemplified compounds in the weight parts shown below in place of No. 5.

Exemplary compound No. Structural formula Part by weight All except for using this liquid crystal composition did.

The measurement results are shown below.

15°C 25°C 35°C Response speed 1184 sec 78 μ5 ec d μsec Example 9 In place of Exemplified Compounds 1-2 and 161-55 used in Example 4, the following exemplified compounds were mixed in the following parts by weight to prepare a liquid crystal composition. Object G was created.

Exemplary compound No. Structural formula Heavy 1
A ferroelectric liquid crystal device was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 4.

The measurement results are shown below.

15°C 25°C 35°C Response speed 115μ5ec 75μ5ec 62μsec Example 10 The following exemplified compounds were mixed in the following parts by weight to form a liquid crystal composition H.
It was created.

Exemplified Compound No. Structural Formula Parts by Weight H3 H3 H3 H3 Furthermore, the following exemplary compounds were mixed with the liquid crystal composition H in the weight parts shown below to prepare a liquid crystal composition I.

Exemplary compound No. Structural formula Part by weight All except for using this liquid crystal composition The switching state, etc., were observed.

The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 372 μsec 2326 se
c 175 μsec Comparative Example 2 A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that the liquid crystal composition H mixed in Example 10 was injected into the cell, and the optical response speed was measured. .

The results are shown below.

15℃ 25℃ 35℃Response speed 450 μsec 270 μsec
1951t see Example 11 Exemplary compound 1-1 used in Example 1O. In place of 1-20° and 1-33, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition J.

Exemplary Compound No. Structure 2 Parts by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was determined in the same manner as in Example 4. Measurements were taken to observe the switching state, etc.

The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.

The measurement results are shown below.

Example 12 Exemplary compound 1-1 used in Example 1O. Liquid crystal composition K was prepared by mixing the following exemplified compounds in the weight parts shown below instead of 1-20° and 1-33.

Exemplary compound No. Structural formula Weight part 15°C 25°C 35°C Response speed 362 p sec 229 μ
sec 174 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 4 and the switching state etc. .

The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.

The measurement results are shown below.

Example 13 Exemplary compound 1-1 used in Example io. In place of 1-20° and 1-33, the following exemplified compounds were mixed in the weight parts shown below to prepare a liquid crystal composition.

Exemplary compound No. Structure 2 Part by weight 15°C 25°C 35°C Response speed 376 μsec 233 μsec
c 177 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 4 and the switching state etc. .

The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.

The measurement results are shown below.

Example 14 Exemplary compound 1-1, 1-20゜1 used in Example 10
In place of -33, the following exemplified compounds were mixed in the weight parts shown below to prepare a liquid crystal composition.

Exemplary compound No. Structural formula Weight part 15°C 25°C 35°C Response speed 359 μsec 225 μsec
170 p sec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that the liquid crystal composition was used. The optical response speed was measured in the same manner as in Example 4, and the switching state, etc., was observed. did.

The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.

The measurement results are shown below.

Example 15 Exemplary compound 1-1.1-20゜1 used in Example 1O
Liquid crystal composition M was prepared by mixing the following exemplified compounds in the weight parts shown below in place of -33.

Exemplary compound No. Structural formula Weight part 15°C 25°C 35°C Response speed 302 μsec 187 μs
ee 1421t sec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 4 and the switching state etc. .

The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.

The measurement results are shown below.

Example 16 Exemplary compound 1-1, 1-20゜1 used in Example 1O
Liquid crystal composition N was prepared by mixing the following exemplified compounds in the weight parts shown below in place of -33.

Exemplary compound No., Structural formula Heavy]
Part 15°C 25°C 35°C Response speed 363 p see 230
μsec 172 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 4 and the switching state etc. .

The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 379μsec 231 p se
c 177 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

Example 17 In place of the 1.5% dimethylacetamide solution of the polyimide resin precursor used in Example 4, a 2% aqueous solution of polyvinyl alcohol resin [PUA-117 manufactured by Kuraray ■] was used. A dielectric liquid crystal element was prepared, and the optical response speed was measured in the same manner as in Example 4.

The results are shown below.

15℃ 25℃ 35℃113
μsec 76 μsec 64 μs
ec Example 18 A ferroelectric liquid crystal element was created in the same manner as in Example 4, except that the alignment control layer was created only with polyimide resin without using 5i02 used in Example 4. The optical response speed was measured in the same manner.

The results are shown below.

15℃ 25℃ 35℃111
μsec 75 μsec 64 μs
ec [Effects of the Invention] A device containing the ferroelectric liquid crystal composition of the present invention has good switching characteristics, a liquid crystal device with improved low-temperature operation characteristics, and a liquid crystal device with reduced temperature dependence of response speed. It can be done.

\) Example 17. As is clear from Example 18, even when the device configuration is changed, the device containing the ferroelectric liquid crystal composition according to the present invention has significantly improved low-temperature operating characteristics and a response speed of Dependency has been reduced.

[Brief explanation of drawings]

FIG. 1 is a schematic cross-sectional view of an example of a liquid crystal element using ferroelectric liquid crystal. 2 and 3 are perspective views schematically showing an example of an element cell for explaining the operation of a ferroelectric liquid crystal element. In FIG. 1, 1 . . . Ferroelectric liquid crystal layer 2 .
......Glass substrate 3...
・・・・・・・・・Transparent electrode 4 ・・・・・・・・・・・・
・・Insulating orientation control layer 5・・・・・・・・・・・・・・
・Spacer 6 ・・・・・・・・・・・・・・・ Lead wire 7 ・・・・・・・・・・・・・・・・ Power supply 8 ・
・・・・・・・・・・・・・・・Polarizing plate 9・・・・・・
・・・・・・・・・・・・Light source 10 ・・・・・・・・・
・・・・・・Incoming light I・・・・・・・・・・・・・・・
...Transmitted light in Figure 2, 1b 24... In Figure 3, 1a 1b 3a 3b 34a...34b...... a b Substrate ferroelectricity Liquid crystal layer Liquid crystal molecule dipole moment (on P) Voltage application means Voltage application means First stable state Second stable state Upward dipole moment Downward dipole moment I・Upward electric field Downward electric field

Claims (2)

[Claims] (1) The following general formula (I) R_1-X_1-A-Y-A'-X_2-R_2[ I
] (In the formula, R_1 and R_2 are each an alkyl group having 1 to 16 carbon atoms which may have a substituent, and X_
1 indicates a single bond or -O-, X_2 indicates a single bond, -O
−, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. A is cis-1,4-cyclohexylene, and Y represents ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2O- or -OCH_2-. A' is -A_1- or -A_1-A_2-, and A_1 and A_2 are respectively ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ ▲There are mathematical formulas, chemical formulas, tables, etc. ▼、▲Mathematical formula, chemical formula,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
Indicates ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. Here, X_3 and X_4 are hydrogen atoms, F, Cl, and
Br, CH_3, CN or CF_3, and Z is -O
- or -S-. ) A ferroelectric chiral smectic liquid crystal composition containing at least one liquid crystal compound represented by the following. (2) A liquid crystal device comprising the ferroelectric chiral smectic liquid crystal composition according to claim 1 disposed between a pair of electrode substrates.