JPS63254182A - Ferroelectric liquid crystal element - Google Patents

Abstract

PURPOSE:To obtain the titled element having excellent low-temperature operat ing characteristics and high-speed response, comprising a novel liquid crystal composition containing a specific liquid crystal compound in a ferroelectric liquid crystal layer. CONSTITUTION:The aimed element containing one or more liquid crystal compounds shown by formula I {A1 and A2 are bifunctional six-membered ring which may contain substituent group; X is -(CH2)l -O- or -O-(CH2)m; land m are 1 or 2; at least one of R1 and R2 contains asymmetric carbon and when R1 and R2 are the same, R1 and R2 are group shown by formula II-IV [Y1-Y3 are single bond or -O-; n1 and n2 are 0-8; R3-R5 are replaceable 1-18C chain alkyl; Z1 is -(CH)n2-(n2 is 0 or 1) or carbonyl; Z2 is -CH3 or CN; Z3 is halogen] and further when R1 is different from R2, one of R1 and R2 is group shown by formula II-IV and the other is R3 or acyloxy} in a ferroelectric liquid crystal layer. A compound shown by formula V may be cited as the liquid crystal compound.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Application of the Invention] The present invention relates to a ferroelectric liquid crystal device, and more particularly to a ferroelectric liquid crystal device having a substrate, a voltage application means, an insulating alignment control layer, and a ferroelectric liquid crystal layer. In particular, the present invention relates to a ferroelectric liquid crystal element containing a specific liquid crystal compound in the ferroelectric liquid crystal layer.

[Prior art]

Liquid crystals have already been applied as various optical modulation elements, and in particular, have been put to practical use as display elements in watches, calculators, and the like.

This is because liquid crystal elements consume extremely little power and can be made thinner and lighter, and because the display element is a light-receiving element, it causes less eye fatigue even when used for long periods of time. It is something.

Most of the liquid crystal elements currently in practical use are, for example, M
, 5chadt and W. He1frich “Appl.
iedPhysics Letters ”Vo, 1
8. No. 4 (1971, 2, 15) P, 127
~128 “Voltage Dependent 0p
ticalActivity of a Twi
sted Nematic Liquid Crys
Twisted Nem
atic) type liquid crystal.

These are based on the dielectric alignment effect of liquid crystals, and utilize the effect that the average molecular axis direction is oriented in a specific direction by an applied electric field due to the dielectric anisotropy of liquid crystal molecules.

The limit of the optical response speed of these elements is several m s e
c, and is an obstacle to expanding the field of application of liquid crystal devices.

In order to take advantage of the features of liquid crystal elements such as low power consumption and light-receiving type, and to ensure responsiveness comparable to electroluminescent and other light-emitting elements, it is essential to develop a new liquid crystal element to replace the TN type liquid crystal element. One such attempt is the use of bistable liquid crystal elements.
1ark and Lagerwall (JP-A-56-107216, U.S. Patent No. 4,
367.924 specification, etc.).

As the bistable liquid crystal, a ferroelectric liquid crystal having a chiral smectic C phase (SmC* phase) or H phase (SmH*) 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. Also,
This type of liquid crystal has a property (bistability) of taking 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.

As described above, ferroelectric liquid crystals potentially have extremely excellent properties, and by utilizing these properties, many of the problems of conventional TN type liquid crystal elements mentioned above can be solved.
A fairly substantial improvement can be obtained.

In particular, it is expected to respond to high-speed optical shutters and high-density, large-screen displays.

For this reason, extensive research has been carried out on liquid crystal materials with ferroelectric properties used in ferroelectric liquid crystal elements, but the ferroelectric liquid crystal elements that have been reported up to now have various characteristics such as low temperature operation characteristics and high speed response. Very few have reached a level of satisfaction, and there are no ferroelectric liquid crystal devices that have been put to practical use.

[Problem that the invention seeks to solve]

SUMMARY OF THE INVENTION It is an object of the present invention to provide a ferroelectric liquid crystal element which eliminates the above-mentioned drawbacks or disadvantages.

Another object of the present invention is to provide a novel ferroelectric liquid crystal composition.

[Means to solve the problem]

This object of the present invention is represented by the following general formula (1).

This is achieved by a ferroelectric liquid crystal element having a ferroelectric liquid crystal layer containing a compound.

General formula (1) R1A 1 X A2 R2 [wherein X is -C
H20-, ÷CH2 arrow 20-, -0CH2-.

-0Mo CH2 Arrow 2 selected.

R,, R2 may be the same or different, and at least one of them has an asymmetric carbon.

When R1 and R2 are the same, R1 and R2 are represented by the following general formula (2
).

Indicated by (3) or (4).

General formula (2) %Formula% (However, in the formula, Y1 is a single bond, -o-, -c-, -oc-
.

1j1 -CH2CH2C〇- or -CH=CHC0-1n1 represents an integer from 0 to 8, zl represents (CH2)- or -C-, n2 represents O or 1
shows. ), R3 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms which may have a substituent, and preferred specific examples include methyl, ethyl, butyl, pentyl, hexyl, octyl, Examples include barrel, isopropyl, etc.

), *marks indicate asymmetric carbons. )-Y2 child CH2 sho-CH
-R4 n3* -CH2CH2C〇- or -CH-CHCO-1n3 represents an integer from 0 to 8, Z2 represents -CH3, CN.

R4 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms which may have a substituent, and preferred specific examples include methyl, ethyl, butyl, pentyl, hexyl, octyl, barrel, isopropyl, etc. can be given. )
, * indicates an asymmetric carbon. )-Y3 child CH2'+-CH
-R5 n4* n4 represents an integer from θ to 8, Z3 represents a halogen atom, and preferred specific examples include:
Examples include fluorine, chlorine, and bromine.

R5 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms which may have a substituent, and preferred specific examples include methyl, ethyl, butyl, pentyl, hexyl, octyl, barrel, isopropyl, etc. can be given. )
, the xylem exhibits asymmetric carbon. ) Also, when R1 and R2 are different, one of R1 and R2 is represented by the following general formula (2),
(3) or (4), -Y1 child CH2:) -CH-Z, -OR3nl* -Co-, -0CO-, -CH20-, -CH2CH2
0-.

selected from O -C112CH2C〇- or -CH=CHC0-, nl represents an integer from 0 to 8, Zl represents (:CH23- or -C-, (n2 represents O or 1) R3 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms which may have a substituent, and * represents an asymmetric carbon.) General formula (3) % formula % (However, in the formula Y2 is a single bond, -O-, -C-, ~OC-
.

O0 -CO-, -0CO-, -CH20-, -CH2CH2
0-.

o　　　　　　o　’.

II 11 ll-CH20
(, -, -CH2CH20C-, -CH2Co-.

selected from -CH2CH2C〇- or -CH-CHC〇-, n3 represents an integer from θ to 8, and Z2 represents -CH3 or CN. ) R4 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms which may have a substituent, and the mark * represents an asymmetric carbon. ) General formula (4) % Formula % selected from -CH2CH2Co- or -CH=CHC0-, n4 represents an integer from 0 to 8, Z3 represents a halogen atom, R5 has a substituent, represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms, and the * mark represents an asymmetric carbon. ) The other of R1 and R2 is a branched or straight alkyl group having 1 to 18 carbon atoms which may have a substituent, or a branched or straight alkyl group having 1 to 18 carbon atoms which may have a substituent. Indicates an acyl group, acyloxy group, alkoxy group, alkoxycarbonyl group, or alkoxycarbonyloxy group having an alkyl group in the chain.

Preferred specific examples include methyl, ethyl, propyl,
Alkyl groups such as butyl, pentyl, hexyl, isopropyl, acetyl, propionyl, butynyl, valeryl,
Acyl groups such as valmitoyl, 2-methyl-propionyl, acetyloxy, propionyloxy.

Acyloxy groups such as butynyloxy, 2-methyl-propionyloxy, alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, 2-methyl-butoxy, alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl, butoxycarbonyl, 2-methyl-butoxycarbonyl, etc. group, alkoxycarbonyloxy groups such as methoxycarbonyloxy, ethoxycarbonyloxy, butoxycarbonyloxy, and 2-methyl-butoxycarbonyloxy.

At this time, as further substituents for the group represented by R, R2,
Halogen atoms such as fluorine, chlorine, and bromine, and methyl.

Alkyl groups such as ethyl, propyl, butyl, pentyl,
Examples include alkoxy groups such as methoxy, propoxy, butoxy, trifluoromethyl, and cyano groups.

AI + A2 represents a divalent ring group which may have a substituent, and preferred specific examples thereof are as follows.

In general formula (1), when at least one of R1 and R2 has general formula (2) or (4), A1°A2 is represented by general formula (5).

General formula (5) Child A3 A4 Te (In the formula, A3 and A4 are preferably selected from those that may have a substituent, and p and q are represented by 0.1 or 2.) General formula In (1), when at least one of R8 and R2 has general formula (3), A2 is represented by general formula (6).

General formula (6) 壬A5arrow (A6arrow (in the formula, A5 and A6 may be the same or different, and A5.
A6 is selected from those which may have a substituent.

However, when A5 and A6 are different, either one may be one point. r and s are 0, 1 or 2. ) Also, A
3. Further substituents for the group represented by A4 include halogen atoms such as fluorine, chlorine, and bromine, and methyl.

Alkyl groups such as ethyl, propyl, butyl, methoxy,
Examples include alkoxy groups such as ethoxy and propoxy, trifluoromethyl, and cyano groups.

Representative examples of compounds having general formula (2) are listed below.

H3 C2H5, -@-0CH2 (X defense 0CH2CHOC3H
7* H3 ■ c 4H9-@-CH□(T)◎-@-OCH2CHO
C15H.

*H3 Cs H17% OCH2 buildings 0CI(2CI(OC2H
5* H3 ■ 012H25-o-o-OCH2-@r-OCH2CI
]0C3H5*H3? C16H33-@-@-CH20 (■0CH2CHOC
6H13* H3 ■C4H90sha0CH2-@F@-OC■]2CHOC2
2H25* H3 ■ O〒H3 C8H1□CO-@l-CH20-@1-@1-ocI
]2cHoc4H9* * CH3 ■ 1- (25)? H3C8H1□0
-@-CH20 color X defense O child CH2 arrow. CHOC5Hn* TeH3 C8H1□o(YnaCH20(filter0CHCH2QC2H
5* CH3 * Not* T.

Cs + CH20m OCH2CHOCa Hl□* * 2- (49) CH
3* * CH3 Not* CH3CH3 C■13 CH3 λT II C6H130 Color Fna CH2 (T) Minute CH2O-CH2C
HOC8I]17* 2-(8”)(?1□3 C6HI3-■-@-CH20-◎riI(2CI]2O
-CH2CHOC8IJ17* Representative examples of compounds having general formula (3) are listed below.

Compound No.

3- (3) 〒■13 C8I] I?埒8 柒 0CH3-忰0CHCa H+3* 3-(4)ocH3 II 1 CI2 H25 埒8) OCH2-sha C0CH2CHC2H
5* 3-(5) CH3 CI6' 33埒；pcH20-忰OC■]2CHC
2H5* * Book* * * * * * * * * * Not* * * Not N N NotφNot* ~ H3 λ■1 T.

C6H13o(TSUKASHIFCH2(g)忰CH2O-CH2C
HC2H5* Representative examples of compounds having general formula (4) are listed below.

Compound no.

4-(1)F C2H5-4 or OCH2% OCH2CHC4H9* C41-19-忰C1(20-@-@-CCI(2CI
(C51(,.

*C8■]1□(ka(sawa0CH2-忰0CH2C11C6
H33* ■ CI2 H25% OCH2 ((filtration OC ■ (2CI-I
C7H75* ■ C,6H33-@-+filtration CH2o (filtration 0CH2CHC8
■(17* ■ C4H9-@-OCH2-@-@-OCH2CHC, o
H2゜* ■ C6H130-@/-CH2 Chinkaya Oki CH2CHC6H
33* * Cto H210+ OCH2M OCH2CHCe
H13* No 1] 1 c, 6H320C-@-ocr-■2-@-@-OC
H2CHCH2CH (CT-I 3) 2* Non-CI-I3 0 02F■5C1-■ClI20C (filter ocn2-4 or one @-OCH2CH-C3H7* Book 4~ (28) * 4-(3)) * * * 081 ,.O-@)-@)-CH20(masu CH2CHC
6H13* 4~ (37) Book * * * 0 (J! 08HI7 (SIΣOCH2 0% CH2).cHc
2H5* * 4-(55)F 4,-(57) 4,-(64) 113F Honsho hT ICI ■ WT 1st Ce H+30@1-o-CH20-忰CH2CH20
CH2Cl-IC6H13* Next, a typical synthesis example of the liquid crystal compound used in the present invention will be described below.

Synthesis Examples 1 to 1 (Synthesis of Exemplary Compound No. 2-7)
In a 30 ml eggplant flask, add the following alcohol derivative 1,
Og (3.05 mmoA) was added thereto, 3 m of thionyl chloride, ff was added under cooling, and the temperature was raised to room temperature while stirring.Furthermore, a cooling tube was attached, and heating and reflux was performed at an external bath temperature of 7000 to 80°C for 4 hours. After the reaction, excess thionyl chloride was distilled off to obtain a chloride. This was dissolved in 15 mA of toluene.

Next, 0.31 g of 60% oily sodium hydride was placed in a 200 m jl' three-necked flask, washed several times with dry n-hexane, and then 0.60 g of the following phenol derivative (3
,05mmon)HO()OC6H13 in THF solution (15m), f2 was lowered to the bottom of room temperature, and then D
20rrl of MSO was added and stirred for 1 hour. To this, the toluene solution of the chloride mentioned above was slowly added dropwise, and after the dropwise addition was completed, stirring was continued for 16 hours at room temperature.

Approximately 200 mj after the reaction is completed! The organic layer was separated, and the aqueous layer was extracted twice with 50 m 12 of benzene, and the organic layer was extracted with 5% aqueous hydrochloric acid for 2
After washing twice, once with ion-exchanged water, and then with 5% NaOH.
The organic layer was washed once with an aqueous solution, and then the organic layer was washed with ion-exchanged water until the pH value of the aqueous layer became neutral.

The organic layer was removed and dried using magnesium sulfate.
The solvent was distilled off to obtain a crude product. This was purified by silica gel column chromatography using a developing solution of n-hexane/dichloromethane, 3/10.

The crystals obtained by distilling off the solvent were recrystallized using n-hexane to obtain the purified target product. Further, drying was performed under reduced pressure at room temperature to obtain 0.45 g of the final purified target product.

The yield was 29.3%.

CHN analysis value (W t%) CHN calculated value 78.53 8.79 0 Measured value 78.96 8.95 0.02 Phase transition temperature IR spectrum 2970, 2930, 2855, 1
610°1515, 1400. 1385. 1,2
90°1275, 1240. 1220. 1120
゜1020, 830.825 cm' Synthesis Synthesis-1
(Synthesis of Exemplified Compound No. 2-28) 1.25 g of the following alcohol derivative (4,
01mmoA) and, under cooling, thionyl chloride 4.
m 12 was added, the temperature was raised to room temperature while stirring, a cooling tube was attached, and heating and reflux was performed at an external temperature of 708C to 80C for 4 hours. After the reaction, excess thionyl chloride is distilled off,
Obtained chloride. This is 15mj of toluene? dissolved in.

Next, 0.31 g of 60% oily sodium hydride was placed in a 200 m jl' three-necked flask, washed several times with dry n-hexane, and then 0.79 g of the following phenol derivative (4,
01 mmol of THF solution 15 mjl! The temperature was lowered to room temperature, and 20 mA of DMSO was added thereto, followed by stirring for 1 hour. To this, the toluene solution of the chloride mentioned above was slowly added dropwise, and after the dropwise addition was completed, stirring was continued for 16 hours at room temperature.

After the reaction was completed, the organic layer was poured into ice water at about 200 mA, the organic layer was separated, and the aqueous layer was extracted twice with 50 μm of benzene. After washing with the previously separated organic layer twice with 5% aqueous hydrochloric acid solution, the ions were extracted. After washing once with exchanged water and once with 5% NaOH aqueous solution, the organic layer was washed with ion-exchanged water until the pH value of the aqueous layer became neutral.

The organic layer was taken out, dried using magnesium sulfate, and the solvent was distilled off to obtain a crude product. Add this to the developing solution n-hexane/
Purification was performed by silica gel column chromatography using dichloromethane, 3/1O.

The crystals obtained by distilling off the solvent were recrystallized using n-hexane to obtain the purified target product. Further, the product was dried under reduced pressure at room temperature to obtain 0.51 g of the final purified target product.

The yield was 26.0%.

CHN analysis value (w t%) CHN calculated value 78.33 8.63 0.00 Theoretical value
78.62 8.86 0.02 phase dislocation S2+”3 unidentified IR spectrum 2975. 2925,2850.
1610°1510, 1470. 1380. 1
295°1280, 1240. 1220. 113
0°1020, 1000.810 cm' Synthesis Example 1-3 (Synthesis of Exemplary Compound No. 2-59) 30
m A 1.0 g of the following alcohol derivative in an eggplant flask
(3,57 mmoj!), add 3 m 41' of thionyl chloride under cooling, raise the temperature to room temperature while stirring, and then attach a cooling tube and reduce the external temperature to 70°C to 80°C.
The mixture was heated under reflux for 4 hours. After the reaction, excess thionyl chloride was distilled off to obtain a chloride. This was dissolved in 15 mA of toluene.

Next is 200mI! Put 0.32 g of 60% oily sodium hydride into a three-necked flask, wash it several times with dry n-hexane, and then add 1.11 g (3,57 g) of the following phenol derivative.
mmoj? ) of THF solution 15 m I! was lowered to room temperature, and then added 20 mI! of DMSO! The mixture was added and stirred for 1 hour. To this, the toluene solution of the chloride mentioned above was slowly added dropwise, and after the dropwise addition was completed, stirring was continued for 16 hours at room temperature.

Approximately 200 m after the completion of the reaction! The mixture was poured into ice water, the organic layer was separated, and the aqueous layer was extracted twice with 50 mA' of benzene. After washing with the previously separated organic layer twice with a 5% aqueous hydrochloric acid solution, it was extracted once with ion-exchanged water. times, and an additional 5% NaO
After washing once with an aqueous H solution, the organic layer was washed with ion-exchanged water until the pH value of the aqueous layer became neutral.

The organic layer was taken out, dried using magnesium sulfate, and the solvent was distilled off to obtain a crude product. Add this to the developing solution n-hexane/
Purification was performed by silica gel column chromatography using dichloromethane, 3/10.

The crystals obtained by distilling off the solvent were recrystallized using n-hexane to obtain the purified target product. Further, the product was dried under reduced pressure at room temperature to obtain 0.39 g of the final purified target product.

The yield was 18.9%.

CHN analysis value (wt%) CHN calculated value 77.319.47 4.87 measured value 77
．． 92 9.53 4.90 Regarding exemplified compounds other than the synthesis examples, compounds having general formula (2) can be easily produced using the same method.

Synthesis Example 2-1 (Synthesis of Exemplified Compound No. 3-28) The following alcohol derivative 1.
0 g (4.81 mmoA), 3 ml of thionyl chloride was added under cooling, the temperature was raised to room temperature while stirring, a cooling tube was attached, and the mixture was heated under reflux at an external temperature of 70°C to 80°C for 4 hours. Ta. After the reaction, excess thionyl chloride was distilled off to obtain a chloride. This was dissolved in 15 mA' of toluene.

Next is 200mI! 0.35 g of 60% oily sodium hydride was placed in a three-necked flask, washed several times with dry n-hexane, and then 1.36 g of the following phenol derivative (4,81
A THFHF solution of mmoA) was lowered to a temperature of 15°C, and 20 mR of DMSO was added thereto, followed by stirring for 1 hour. To this, the aforementioned toluene solution of chloride was slowly added dropwise, and after the dropwise addition was completed, stirring was continued for 16 hours at room temperature.

After the reaction was completed, the mixture was poured into ice water at about 200 mA, the organic layer was separated, and the aqueous layer was extracted twice with 50 mI of benzene.
The previously separated organic layer was washed twice with a 5% aqueous hydrochloric acid solution, then once with ion-exchanged water, and then once with a 5% aqueous NaOH solution, and then washed with ion-exchanged water until the pH value of the aqueous layer became neutral. The organic layer was washed with water.

The organic layer was taken out, dried using magnesium sulfate, and the solvent was distilled off to obtain a crude product. Add this to the developing solution n-hexane/
Purification was performed by silica gel column chromatography using dichloromethane, 3/1O.

The crystals obtained by distilling off the solvent were recrystallized using n-hexane to obtain the purified target product. Further, the product was dried under reduced pressure at room temperature to obtain 0.51 g of the final purified target product.

The yield was 22.6%.

Elemental analysis value (wt%) CHN Calculated value 75.91 8.07 5.90 Measured value 7
6.23 8.39 6.16 Synthesis Example 2-2 (Synthesis of Exemplified Compound No. 3-40) 1.0 g of the following alcohol derivative (3.38 m
moA) was added thereto, 3 mR of thionyl chloride was added under cooling, and the temperature was raised to room temperature while stirring.Furthermore, a cooling tube was attached, and heating and reflux was performed at an external temperature of 70°C to 80°C for 4 hours. After the reaction, excess thionyl chloride was distilled off to obtain a chloride. This was dissolved in 15 mA' of toluene.

Next 200 m I! Put 0.35 g of 60% oily sodium hydride into a three-neck flask, wash it several times with dry n-hexane, and then add 0.61 g of the following phenol derivative (
3,38m mo ji! ) of THFHF solution (15 cm) was added dropwise under heating, and then 20 mjl of DMSO was added! The mixture was added and stirred for 1 hour. To this, the toluene solution of the chloride mentioned above was slowly added dropwise, and after the dropwise addition was completed, stirring was continued for 16 hours at room temperature.

After the reaction was completed, the organic layer was poured into ice water at about 200 mA, the organic layer was separated, and the aqueous layer was mixed with benzene at 50 m, f! After extracting twice with 5% NaO and washing with 5% aqueous hydrochloric acid solution together with the previously separated organic layer, once with ion-exchanged water and then with 5% NaO
After washing once with an aqueous H solution, the organic layer was washed with ion-exchanged water until the pH value of the aqueous layer became neutral.

The organic layer was taken out, dried using magnesium sulfate, and the solvent was distilled off to obtain a crude product. Add this to the developing solution n-hexane/
Purification was performed by silica gel column chromatography using dichloromethane, 3/10.

The crystals obtained by distilling off the solvent were recrystallized using n-hexane to obtain the purified target product. Further, the product was dried under reduced pressure at room temperature to obtain 0.37 g of the final purified target product.

The yield was 23.8%.

Elemental analysis value (wt%) CHN Calculated value 78.67 8.80 6.12 Measured value
79.18 8.98 6.32 Compounds other than the synthesis examples are generally synthesized by the general formula (
3) can be easily produced.

Synthesis Example 3-1 (Synthesis of Exemplary Compound No. 4-7)
30+r+42 Add the following alcohol derivative 1 to an eggplant flask.
．． 0 g (4.81 mmoA) was added thereto, 3 ml of thionyl chloride was added under cooling, the temperature was raised to room temperature while stirring, a cooling tube was attached, and the mixture was heated under reflux at an external temperature of 70° C. to 80° C. for 4 hours. After the reaction, excess thionyl chloride was distilled off to obtain a chloride. This was dissolved in 15 ml of toluene.

Next, 0.33 g of 60% oily sodium hydride was placed in a 200 ml three-necked flask, washed several times with dry n-hexane, and 1.52 g of the following phenol derivative (4,
81m mo 1! ) THF solution 15mj? was added dropwise at room temperature, and further 20 mjl' of DMSO was added and stirred for 1 hour. To this, the toluene solution of the chloride mentioned above was slowly added dropwise, and after the dropwise addition was completed, stirring was continued for 16 hours at room temperature.

Approximately 200 mj after the reaction is completed? Pour into ice water, separate the organic layer, and add 50 m of benzene to the aqueous layer! ! After extraction was performed twice with the previously separated organic layer, the pH of the aqueous layer was The organic layer was washed with ion-exchanged water until the value showed neutrality.

The organic layer was taken out, dried using magnesium sulfate, and the solvent was distilled off to obtain a crude product. This was purified by silica gel column chromatography using a developing solution of n-hexane/dichloromethane, 3/10.

The crystals obtained by distilling off the solvent were recrystallized using n-hexane to obtain the purified target product. Further, the product was dried under reduced pressure at room temperature to obtain 69 g of the final purified target product.

The yield was 28.5%.

Elemental analysis value (wt%) CHN Calculated value 78.33 8.57 0.00 Measured value
78.96 8.69 0.02 Phase rearrangement synthesis example 3-2 (synthesis of exemplified compound No. 4-58)
1.0 of the following alcohol derivative in a 30 mA' eggplant flask.
g (3.94 mmojl!), added 3 m12 of thionyl chloride under cooling, and raised the temperature to room temperature while stirring.Furthermore, a cooling tube was attached, and heating and reflux was performed for 4 hours at an external temperature of 70 ° C to 80 ° C. . After the reaction, excess thionyl chloride was distilled off to obtain a chloride. Add this to 15ml of toluene! dissolved in.

Next, 0.31 g of 60% oily sodium hydride was placed in a 200 ml three-necked flask, washed several times with dry n-hexane, and then 1.18 g (3.94 m
mo j! ) THF solution 15 ml! The temperature was lowered to room temperature, and DMSO was further added at 20 mA and stirred for 1 hour.

To this, the aforementioned toluene solution of chloride was slowly added dropwise, and after the dropwise addition was completed, stirring was continued for 16 hours at room temperature.

Approximately 200 m after the completion of the reaction! The organic layer was separated, and the aqueous layer was extracted twice with 50 ml of benzene. The organic layer was washed with 5% aqueous hydrochloric acid twice, then once with ion-exchanged water, and then the organic layer was extracted twice with 50 ml of benzene. 5% NaOH
After washing once with an aqueous solution, the organic layer was washed with ion-exchanged water until the pH value of the aqueous layer became neutral.

The organic layer was taken out, dried using magnesium sulfate, and the solvent was distilled off to obtain a crude product. Add this to the developing solution n-hexane/
Purification was performed by silica gel column chromatography using dichloromethane, 3/10.

The crystals obtained by distilling off the solvent were recrystallized using n-hexane to obtain the purified target product. Further, the product was dried under reduced pressure at room temperature to obtain 0.51 g of the final purified target product.

The yield was 24.3%.

Elemental analysis value (wt%) CHN Calculated value 78.43 9.21 5.23 Measured value 7
8.92 9.42 Compounds other than those on the 5,46 phase transition temperature synthesis side are also generally converted into halides or torsicates of alcohol derivatives by a conventional method, and then reacted with the corresponding alcohol derivative in the presence of an alkali to form the general formula. A compound having (4) can be easily produced.

The ferroelectric liquid crystal layer in the ferroelectric element according to the present invention is prepared by mixing one or more liquid crystal compounds represented by the general formula (1) with one or more other ferroelectric liquid crystal compounds in an appropriate ratio. It is preferable to heat the material in vacuum to an isotropic liquid temperature, encapsulate it in an element cell, gradually cool it to form a liquid crystal layer, and return it to normal pressure.

Other ferroelectric liquid crystal compounds used in the present invention include the following compounds.

(1) CH3 cover (2) cI (3 ■ C9H390, -@-COOshao-cH2cHc2H5
* (3) CH3 C3゜H2,0-o-COO@-o-cH2cHc2H
5* (4) CH3 (5) , CH3(
6)〒I]3 C1゜H2, o-@-coo-@-o-e CH2E)
-3CHC2H6* ■ (8) CH3 C2H50CI (C■1□o-@-coo -@-@-
cooc,. ■(2, * (9) CH3 C31, □0CHCH20-@-COO-qdeath@-co
oc 61, 3* (10)〒H3 c 8H, □0CHCH20-@-Coo -@-@-
C00C, oH□.

*c, oH2□O-@-COO ocn 2CHOC2
H5* (12) TeI]3c, oH2,
o$ CH=N-@)-CH=CH-C00CH2CH
C2H5* (14) CH3 c 2H5cH-+ CH2E)-3-@-@-COO
C7H15CH3 The compounding ratio of the liquid crystal compound represented by the general formula (1) of the present invention and one or more of the above-mentioned ferroelectric liquid crystal compounds (hereinafter abbreviated as ferroelectric liquid crystal material) is 100% of the ferroelectric liquid crystal material. It is preferable that the amount of the liquid crystalline compound of the present invention is 1 to 500 parts by weight per part by weight.

Furthermore, when using two or more types of liquid crystal compounds of the present invention, the blending ratio with the ferroelectric liquid crystal material is such that a mixture of two or more types of liquid crystal compounds of the present invention is used per 100 parts by weight of the above-mentioned ferroelectric liquid crystal material. 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 display element having a ferroelectric liquid crystal layer, for explaining the structure of the ferroelectric liquid crystal element. In FIG. 1, number 1 is a ferroelectric liquid crystal layer, 2 is a glass substrate, 3 is a transparent electrode, 4 is an insulating alignment control layer, and 5 is a ferroelectric liquid crystal layer.
is a spacer, 6 is a lead wire, 7 is a power supply, 8 is a polarizing plate,
9 indicates a light source.

The two glass substrates 2 are each made of In2O3.

SnO2 or ITO (Indium-Tin
It is coated with a transparent electrode made of a thin film such as (Oxide) or the like. 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. Also,
Examples of insulating layers include silicon nitride, hydrogen-containing silicon carbide, silicon oxide, boron nitride, hydrogen-containing boron nitride, cerium oxide, aluminum oxide, zirconium oxide, titanium oxide, and magnesium fluoride. An inorganic material insulating layer of polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyparaxylene, polyester, polycarbonate, polyvinyl acecool, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin is formed on the inorganic material insulating layer. An insulating orientation control layer may be formed of two layers, using an organic insulating material such as melamine resin, yurya resin, acrylic resin, or photoresist resin as the orientation control layer, or an insulating orientation control layer of an inorganic material or an organic insulating material. It may be a single layer of material insulating orientation control layer. If this insulating alignment control film is inorganic, it can be formed by a vapor deposition method, or if it is organic, it can be formed in a solution of an organic insulating substance or its precursor solution (0.1 to 20% by weight in a solvent, preferably 0.1 to 20% by weight in a solvent). 2~IO
% by weight) by a spinner coating method, dip coating method, screen printing method, spray coating method, roll coating method, etc., and can be cured and formed under predetermined curing conditions (for example, heating).

The thickness of the insulating orientation control layer is usually 50 to 1 μm, preferably 100 to 5,000, and more preferably 500 to 3,000. , These two glass substrates 2 are kept hidden for an arbitrary period of time by spacers 5. For example, there is a method in which silica beads or alumina beads having a predetermined diameter are used as spacers and are sandwiched between two glass substrates, and the periphery is sealed using a sealing material such as an epoxy adhesive. In addition, a polymer film, glass fiber, or the like 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 encapsulated generally has a thickness of 0.5 to 20μ, preferably 1μ to 5μ.

The transparent electrode 3 is connected to an external power source 7 by a lead wire. Further, a polarizing plate 8 is pasted on the outside of the glass substrate 2. Since the device shown in FIG. 1 is of a transmission type, 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 respectively ■n203. SnO2 or ITO (In
A substrate (glass plate) coated with a transparent electrode made of a thin film such as dium-Tin oxide), between which a liquid crystal layer of SmC* layer or SmH* layer is oriented so that the liquid crystal molecular layer 22 is perpendicular to the glass surface. is included. A thick line 23 represents a liquid crystal molecule, and this liquid crystal molecule 23 has a dipole moment (P±) 14 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 liquid crystal molecules 2
The helical structure of 3 unravels, and the dipole moment (P soil) 2
4 are all oriented in the direction of the electric field (so that the liquid crystal molecules 23 can change their orientation direction.The liquid crystal molecules 23 have an elongated shape, and have refractive index anisotropy in the long axis direction and the short axis direction. Therefore, it is easy to understand that, for example, if crossed nicol 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 thickness of the liquid crystal cell preferably used in the optical modulation element of the present invention can be made sufficiently thin (for example, 10μ or less).As the liquid crystal layer becomes thinner in this way, as shown in FIG. Even when no electric field is applied, the helical structure of the liquid crystal molecules unravels, and the dipole moment Pa or pb takes either an upward (34a) or downward (34b) state. When an electric field Ea or Eb of different polarity above a certain threshold value is applied by the voltage applying means 31a and 31b as shown in FIG. Accordingly, the liquid crystal molecules are oriented to either the first stable state 33a or the second stable state 33b.

As mentioned earlier, 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, for example with reference to FIG. 2, the electric field Ea
When the voltage is applied, the liquid crystal molecules are aligned in a first stable state 33a, and this state remains stable even when the electric field is turned off. Further, when an electric field Eb in the opposite direction is applied, the liquid crystal molecules are oriented to the second stable state 23b and change their orientation, but they remain in this state even after the electric field is turned off. Also, the electric field E
As long as a or Eb does not exceed a certain threshold, the respective previous orientations are maintained.

The compounds of 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 1-1 Two glass plates with a thickness of 0.7 m were prepared, an ITO film was formed on each glass plate, a voltage application electrode was created, and SiO2 was further deposited on this to form an insulating layer. . Silane coupling agent [KBM-60 manufactured by Shin-Etsu Chemical ■] on the glass plate
2] A 0.2% isopropyl alcohol solution was applied for 15 seconds at a rotational speed of 200 Or, p, m for surface treatment. Thereafter, a heat drying treatment was performed at 120° C. for 20 minutes.

Furthermore, a polyimide resin precursor [Toshishiku ItO8P-51012%
The dimethylacetamide solution was rotated at 200 rpm.

It was applied for 15 seconds using a spinner. 60 minutes after film formation,
A heating condensation firing treatment was performed at 300°C. At this time, the thickness of the coating film was about 700.

This fired coating was rubbed with acetate flocked cloth, then washed with isopropyl alcohol solution, and alumina beads with an average particle size of 2 μm were sprinkled on one glass plate, so that the rubbing axes of each plate were aligned with each other. The glass plates were glued together using an adhesive sealant [Rixon Pond (Chisso)] and dried by heating at 100°C for 60 minutes to create a cell. Approximately 2μ when measured with a plate
It was m.

Next, the above Exemplary Compound No. 2-7 and the ferroelectric liquid crystal compound shown in the following structural formula in parts by weight Exemplary Compound No. 2-710 (hereinafter, the * mark indicates an asymmetric carbon) were combined in the following parts by weight. The mixture was mixed in a uniformly mixed liquid state under the Tokichi phase and vacuum injected into the cell prepared by the method described above. From Tokichi phase, 0.5°C/h
A ferroelectric liquid crystal element was prepared by slowly cooling the mixture to 25°C.

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

15°C20°C40°C 360μsec 310μsec 205
p sec Example 1-2 Example 1-2 except that each part by weight of a ferroelectric liquid crystal compound represented by the following structural formula was used in place of the two ferroelectric liquid crystal compounds used in Example 1-1. A ferroelectric liquid crystal element was prepared in the same manner as in Example 1-1, and the optical response speed was measured in the same manner as in Example 1-1. The results are shown below.

15°C25°C35°C50°C 860μsec 560μsec 325μs
ec 95 μsec Example 1-3 Example 1-3 except that each part by weight of a ferroelectric liquid crystal compound represented by the following structural formula was used in place of the two ferroelectric liquid crystal compounds used in Example 1-1. A ferroelectric liquid crystal element was prepared in the same manner as in Example 1-1, and the optical response speed was measured in the same manner as in Example 1-1. The results are shown below.

10°C25°0 35°C 4500 μsec 2600 μsec 1
900, czsec Example 1-4 In place of the two ferroelectric liquid crystal compounds used in Example 1-1, each part by weight of a ferroelectric liquid crystal compound represented by the following structural formula was used. A ferroelectric liquid crystal element was prepared in the same manner as in Example 1-1, and the optical response speed was measured in the same manner as in Example 1-1. The results are shown below.

Weight part 100 55°C65°C75°C lO3μsec 90 psec 75
p sec Example 1-5 Example 1-5 except that each part by weight of a ferroelectric liquid crystal compound represented by the following structural formula was used in place of the two ferroelectric liquid crystal compounds used in Example 1-1. A ferroelectric liquid crystal element was prepared in the same manner as in Example 1-1, and the optical response speed was measured in the same manner as in Example 1-1. The results are shown below.

25°C35°C45°C l350μsec 1100μsec 750
μsec Example 1-6 Example 1-1 except that each part by weight of a ferroelectric liquid crystal compound represented by the following structural formula was used in place of the two ferroelectric liquid crystal compounds used in Example 1-1. A ferroelectric liquid crystal element was prepared in the same manner as in Example 1-1, and the optical response speed was measured in the same manner as in Example 1-1. The results are shown below.

0°C5°C20°C 910μsec 780μsec 435
μsec Example 1-7 Polyimide resin precursor 2% dimethylacetamide solution used in Example 1-1 was replaced with polyvinyl alcohol resin [PUA-11732% aqueous solution made by Kuraray Kyoku Co., Ltd.]. A dielectric liquid crystal element was prepared, and its optical response speed was measured in the same manner as in Example 1-1. The results are shown below.

15°C20°C40°C 365μsec 315μsec 220
μsec Example 1-8 A ferroelectric liquid crystal element was fabricated in the same manner as in Example 1-1, except that the insulating alignment control layer was made only of polyimide resin without using the SiO2 used in Example 1-1. was prepared, and the optical response speed was measured in the same manner as in Example 1-1. The results are shown below.

15°C20°C4o0C 350μsec 295μsec 200μ
sec Examples 1-9 to 1-29 In place of Exemplified Compound No. 2-7 used in Example 1-2, the liquid crystal compound of Exemplified Compound No. shown in Table 1 was used in the parts by weight shown in Table 1. A ferroelectric liquid crystal element was prepared in exactly the same manner as in Example 1-2 except for the above, and the optical response speed was measured. The results are shown in Table 1.

Table 1 Example 2-1 Exemplary compound No. of Example 1-1, No. 2-7, No. 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

15°C20°C4,0°C 360μsec 315μsec 215
μsec Example 2-2 Example compound No. 2-7 of Example 1-2, No. 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

15℃ 25℃35℃50℃930μse
c 570 μsec 340 μsec 12
5 μsec Example 2-3 Exemplary compound No. 12-7 of Example 1-3 was used as No. 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

15°C25°C45°C 5100μsec 2750 μsec 1200
μsec Example 2-4 Exemplary compound No. of Example 1-4, No. 2-7, 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

55°C65°C75°C 115μsec 98μsec 80μsec
Example 2-5 Example compound No. 2-7 of Example 1-5, No. 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

25°C35°C45°C 1480μsec 1050μsec 85
0 p see Example 2-6 Exemplary compound No. of Example 1-6, No. 2-7, No. 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

0℃ 5℃2o0C 890μsec 650μsec 420μs
ec Example 2-7 Example compound No. 2-7 of Example 1-7, No. 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

15°C20°C40°C 355μsec 300μsec 20
0 μSeC Example 2-8 Example compound No. 2-7 of Example 1-8, No. 3-2
A ferroelectric liquid crystal element was prepared using the same weight parts except that the ferroelectric liquid crystal compound represented by No. 8 was used, and the optical response speed was measured.

The results are shown below.

15°0 20°C 40°C350μs
ec 290 μsec 190 B sec
Examples 2-9 to 2-31 Except that the compound No. 3 shown in Table 2 was used in the parts by weight shown in Table 2 in place of Exemplary Compound No. 3-28 used in Example 2-2. A ferroelectric liquid crystal device was prepared in exactly the same manner as in Example 2-2, and its optical response speed was measured. The results are shown in Table 2.

Table 2 Example 3-1 Example compound No. 2-7 of Example 1-1, No. 4-7
A ferroelectric liquid crystal element was prepared using the same parts by weight except that the ferroelectric liquid crystal compound represented by was used, and the optical response speed was measured.

The results are shown below.

15°C20°C40°C 340 μsec 290 p sec 195
μsec Example 3-2 Example compound No. 2-7 of Example 1-2 No. 4-7
A ferroelectric liquid crystal element was prepared using the same parts by weight except that the ferroelectric liquid crystal compound represented by was used, and the optical response speed was measured.

The results are shown below.

15°C25°C35°C50'C 830p sec 530 μsec 295 μ
sec 100 μsec Example 3-3 Example compound No. 2-7 of Example 1-3 No. 4-7
A ferroelectric liquid crystal element was prepared using the same parts by weight except that the ferroelectric liquid crystal compound represented by was used, and the optical response speed was measured.

The results are shown below.

15℃ 25℃ 35℃33007z
sec 2250μsec 1650μsec
Example 3-4 Example compound No. 2-7 of Example 1-4 No. 4-7
A ferroelectric liquid crystal element was prepared using the same parts by weight except that the ferroelectric liquid crystal compound represented by was used, and the optical response speed was measured.

The results are shown below.

55°C65°C 75°C 100μsec, 80μsec 65μsec
Example 3-5 Example compound No. 2-7 of Example 1-5 No. 4-7
A ferroelectric liquid crystal element was prepared using the same parts by weight except that the ferroelectric liquid crystal compound represented by was used, and the optical response speed was measured.

The results are shown below.

25°C35°0 45°C l250 μsec 1050 μsec 8
50 p sec Example 3-6 Exemplified compound N082-7 of Example 1-6 as No. 4-7
A ferroelectric liquid crystal element was prepared using the same parts by weight except that the ferroelectric liquid crystal compound represented by was used, and the optical response speed was measured.

The results are shown below.

0°C5°C20°C 795μsec 580μsec 39
0 μsec Example 3-7 Exemplary compound No. of Example 1-7, 2-7 as NOo, 4-
A ferroelectric liquid crystal device was prepared using the same parts by weight except that the ferroelectric liquid crystal compound shown in No. 7 was used, and the optical response speed was measured.

The results are shown below.

15°0 20°C 40
°C330p sec 285 μsec
190 p sec Example 3-8 Example compound No. 2-7 of Example 1-8 No. 4-7
A ferroelectric liquid crystal element was prepared using the same parts by weight except that the ferroelectric liquid crystal compound represented by was used, and the optical response speed was measured.

The results are shown below.

15°C20°C400C 325p sec 280 μsec 185
p sec Examples 3-9 to 3-30 In place of Exemplified Compound No. 4-7 used in Example 3-2, a liquid crystal compound of Exemplified Compound No. shown in Table 3 was used in the parts by weight shown in Table 3. A ferroelectric liquid crystal device was prepared in exactly the same manner as in Example 3-2, except that the device was used, and the optical response speed was measured. The results are shown in Table 3.

Table 3 Comparative Example 1 A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that the exemplified compounds No. 7 used in Example 1 were not contained in the ferroelectric liquid crystal layer, and the optical response was The speed was measured. The results are shown below.

20°C30°C40°C 4,20 μsec 380 μsec 325
μsec Comparative Example 2 A ferroelectric liquid crystal element was prepared in the same manner as in Example 2, except that the exemplified compound No. 7 used in Example 2 was not contained in the ferroelectric liquid crystal layer, and the same as in Example 1. The optical response speed was measured using the method described above. The results are shown below.

20°C 25°C 35°G 50°C 60
°C80℃1100μsec 730μsec 5
10μsec 230μsec 170μsec
100 μsec Comparative Example 3 A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that the exemplified compound No. 7 used in Example 3 was not contained in the ferroelectric liquid crystal layer, and the same method as in Example 1 was made. The optical response speed was measured using the method described above. The results are shown below.

20°C25°C35°C45°C 5400 μsec 3600 μsec 290
0 μsec 1800 μsec Comparative Example 4 A ferroelectric liquid crystal element was prepared in the same manner as in Example 4, except that the exemplified compound NO67 used in Example 4 was not included in the ferroelectric liquid crystal layer, and the same method as in Example 1 was made. The optical response speed was measured using the method described above. The results are shown below.

75°C 100 μsec Comparative Example 5 A ferroelectric liquid crystal element was prepared in the same manner as in Example 5, except that the exemplified compound N007 used in Example 5 was not included in the ferroelectric liquid crystal layer. Optical response speed was measured in a similar manner. The results are shown below.

35°C45°C5o°C 1500 psec 1000 μsec 80
0 μsec Comparative Example 6 A ferroelectric liquid crystal element was prepared in the same manner as in Example 6, except that the exemplified compound No. 7 used in Example 6 was not included in the ferroelectric liquid crystal layer. Optical response speed was measured in a similar manner. The results are shown below.

5°0 20℃ 35℃900 ps
As is clear from the results of ec 560 μsec 480 μsec or more, it is clear that the compound according to the present invention is effective as a liquid crystal compound capable of improving low-temperature operating characteristics and high-speed response.

〔Effect of the invention〕

As is clear from the embodiments described above, according to the present invention, a ferroelectric liquid crystal element with improved low-temperature operating characteristics and high-speed response can be realized.

[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 Figure 1, 1 ・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
......Ferroelectric liquid crystal layer 2...
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・Glass substrate 3・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・Transparent electrode 4 ・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
......Insulating alignment control film 5...
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・Spacer 6 ・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・Lead wire 7・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・Power supply 8・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・Polarizing plate 9・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・Light source Io
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・Incoming light I...
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・Transmitted light 2nd
In the figure, 21a ・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・ Board 2
1b ・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・ Board 2
2・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・・・・
...... Ferroelectric liquid crystal layer 23 ......
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
・・・・・・Liquid crystal molecule 24・・・・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・Dipole moment (P±) In Figure 3,

Claims (8)

[Claims] (1) A ferroelectric liquid crystal element containing at least one liquid crystal compound represented by the following general formula (1) R_1-A_1-X-A_2-R_2. [However, in the formula, A_1 and A_2 represent a divalent six-membered ring group which may have a substituent, and X is -(CH_2)-_lO-, -O-
(CH_2)-_m, where l and m represent 1 or 2. R_1 and R_2 may be the same or different,
At least one of them has an asymmetric carbon. R_
When 1 and R_2 are the same, R_1 and R_2 are represented by any of the following general formulas (2), (3), or (4). General formula (2) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the formula, Y_1 is 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.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2O-, -CH_2C
H_2O-, ▲ There are mathematical formulas, chemical formulas, 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. ▼ or ▲ Mathematical formulas, There are chemical formulas, tables, etc. Selected from ▼, n_1
represents an integer from 0 to 8, Z_1 represents -(CH_2)-_n_2 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, (n_2 represents 0 or 1.) R_3 has a substituent. represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms, and the * mark represents an asymmetric carbon. ) General formula (3) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the formula, Y_2 is 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.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2O-, -CH_2C
H_2O-, ▲ There are mathematical formulas, chemical formulas, 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. ▼ or ▲ Mathematical formulas, There are chemical formulas, tables, etc. Selected from ▼, n_3
represents an integer from 0 to 8, and Z_2 represents -CH_3 or CN. ) R_4 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms which may have a substituent, and the mark * represents an asymmetric carbon. ) General formula (4) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the formula, Y_3 is 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.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2O-, -CH_2C
H_2O-, ▲ There are mathematical formulas, chemical formulas, 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. ▼ or ▲ Mathematical formulas, There are chemical formulas, tables, etc. Selected from ▼, n_4
represents an integer from 0 to 8, Z_3 represents a halogen atom, R_5 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms, which may have a substituent, and * indicates an asymmetric carbon shows. ) Also, when R_7 and R_2 are different, either R_1 or R_2 is represented by one of the following general formulas (2), (3), or (4), and the general formula (2) ▲Mathematical formula, chemical formula , tables, etc. ▼ (However, in the formula, Y_1 is a single bond, -O-, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas, tables, etc. There are▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2O-, -CH_2C
H_2O-, ▲ There are mathematical formulas, chemical formulas, 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. ▼ or ▲ Mathematical formulas, There are chemical formulas, tables, etc. Selected from ▼, n_1
represents an integer from 0 to 8, Z_1 represents -(CH_2)_n_2- or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, (n_2 represents 0 or 1.) R_3 has a substituent. represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms, and the * mark represents an asymmetric carbon. ) General formula (3) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the formula, Y_2 is 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.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2O-, -CH_2C
H_2O-, ▲ There are mathematical formulas, chemical formulas, 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. ▼ or ▲ Mathematical formulas, There are chemical formulas, tables, etc. Selected from ▼, n_3
represents an integer from 0 to 8, and Z_2 represents -CH_3 or CN. ) R_4 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms which may have a substituent, and the mark * represents an asymmetric carbon. ) General formula (4) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the formula, Y_3 is 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.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2O-, -CH_2C
H_2O-, ▲ There are mathematical formulas, chemical formulas, 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. ▼ or ▲ Mathematical formulas, There are chemical formulas, tables, etc. Selected from ▼, n_4
represents an integer from 0 to 8, Z_3 represents a halogen atom, R_5 represents a branched or straight-chain alkyl group having 1 to 18 carbon atoms, which may have a substituent, and * indicates an asymmetric carbon shows. ) The other of R_1 and R_2 is a branched or straight chain alkyl group having 1 to 18 carbon atoms which may have a substituent or a branched or straight chain having 1 to 18 carbon atoms which may have a substituent. represents an acyl group, acyloxy group, alkoxy group, alkoxycarbonyl group, or alkoxycarbonyloxy group having an alkyl group. ] (2) In the general formula (1) described in claim 1, at least one of R_1 and R_2 corresponds to the general formula (2)
or (4), when A_1 and A_2 have the following general formula (5
) A ferroelectric liquid crystal element according to claim 1, characterized in that the ferroelectric liquid crystal element is represented by: General formula (5) -(A_3)-_p-(A_4)-_q (However, A_3 and A_4 in the formula are ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
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. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas, There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, It is a six-membered ring-containing group that may have a substituent represented by the following, and p and q are represented by 0, 1, or 2. ) (3) When at least one of R_1 and R_2 in general formula (1) described in claim 1 has general formula (3), A_1 and A_2 are represented by the following general formula (6). A ferroelectric liquid crystal device according to claim 1. General formula (6) -(A_5)-_r-(A_6)-_s (In the formula, A_5 and A_6 may be the same or different, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
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. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas, There are tables, etc. ▼, It is a six-membered ring-containing group that may have a substituent represented by. However, when A_5 and A_6 are different, either one may be ▲There is a mathematical formula, chemical formula, table, etc.▼. r and s are indicated by 0, 1 or 2. ) (4) General formulas (1) and (2) described in claim 1
), general formula (2) when R_1 and R_2 are different
, (3) or (4), the substituent for R_1 or R_2 is selected from a halogen atom, an alkoxy group, a trifluoromethyl, and a cyano group. Ferroelectric liquid crystal element. (5) The ferroelectric liquid crystal element according to claim 1, wherein in the general formula (4) described in claim 1, Z is selected from fluorine and chlorine. (6) A claim characterized in that in the general formula (1) described in claim 1, the substituents A_1 and A_2 are selected from a halogen atom, an alkyl group, an alkoxy group, trifluoromethyl, and a cyano group. The ferroelectric liquid crystal device according to item 1. (7) The ferroelectric liquid crystal device according to claim 1, wherein the ferroelectric liquid crystal device according to claim 1 is a liquid crystal optical modulation device. (8) The ferroelectric liquid crystal device according to claim 1, wherein the ferroelectric liquid crystal device according to claim 1 is a liquid crystal display device.