JPH0348220A - Ferroelectric liquid crystal element - Google Patents

Abstract

PURPOSE:To obtain the ferroelectric liquid crystal element which exhibits a wide operating temp. range, good orientability and memory property and exhibits high-speed responsiveness at room temp. by incorporating a specific ferroelectric liquid crystal compsn. into a ferroelectric liquid crystal layer. CONSTITUTION:The ferroelectric liquid crystal contains at least >=1 kinds of the compds. having the optically active group expressed by formula I and at least one kind of the compds. having the direction of the spiral pitches induced in a nematic phase reverse from the direction of the spiral pitches of the compds. having the optically active group expressed by the formula I and is so formed as to exhibit at least a smectic C phase, a smectic A phase and the nematic phase of >=20mum spiral pitches. The ferroelectric liquid crystal element which has the good orientability, is bright with a high contrast, is wide in the operating temp. range and has the large capacity is obtd. in this way.

Description

DETAILED DESCRIPTION OF THE INVENTION (a) Field of Industrial Application The present invention relates to a ferroelectric liquid crystal device, and more particularly to a substrate. Voltage application means. This invention relates to a ferroelectric liquid crystal element having an alignment control layer and a ferroelectric liquid crystal layer, in which a specific ferroelectric liquid crystal composition is contained in the ferroelectric liquid crystal layer. (b) Prior art Currently, the most widely used liquid crystal display element is one that utilizes the nematic phase. 100
The drawback is that it is difficult to display large amounts of data such as the 0 line. For example, in a normal twisted nematic (TN) type liquid crystal display element, the contrast decreases as the number of lines increases, so a 1000 x 1000
It is virtually impossible to create large capacity display elements such as lines. In order to improve the drawbacks of this TN type liquid crystal display element, super twisted nematic (STN) type liquid crystal display elements and double super twisted nematic (DST) type liquid crystal display elements were developed.
N) type liquid crystal display elements have been developed, but they have the disadvantage that contrast and response speed decrease as the number of lines increases, and currently the display capacity is limited to about 400 x 720 lines. On the other hand, thin film transistors (
An active matrix type liquid crystal display element has also been developed, and it is technically possible to display a large capacity such as 1000 x 1000 lines, but the manufacturing process is long and the yield is low, so the manufacturing cost is extremely high. It has the disadvantage of being expensive.

Ferroelectric liquid crystal elements (NA.
Clark et al. , Appl. Phys.
．． L-ett. , deaf. 899 (see I980))
It is. This display method utilizes ferroelectric liquid crystals such as chiral smectin C phase and chiral smectin 2 phase. Since it is a method that utilizes memory properties, it is possible to increase the display capacity by improving response speed, and since it does not require active elements such as thin film transistors, manufacturing costs do not increase. Ferroelectric liquid crystal elements also have the advantage of wide viewing angles, and are considered very promising as elements for large-capacity displays such as 1000 x 1000 lines.

(c) Problems to be Solved by the Invention In the ferroelectric liquid crystal display using the above-mentioned smectic C phase, the liquid crystal material used therein needs to exhibit the smectic C phase in a wide temperature range centered around room temperature. Of course, it is also necessary to satisfy various other conditions. First, high-speed response is required as a device characteristic for large-capacity display, and from this perspective, liquid crystal materials are required to have high spontaneous polarization and low viscosity. In addition, when applied to a liquid crystal cell, it is necessary to obtain good conformation and bistability, and in addition, it is necessary to obtain good conformation and bistability.
A large value is also desired for the tilt angle, which is related to brightness.

However, it is currently impossible to satisfy all of the desired conditions with a single compound, and usually a mixture of multiple compounds is applied to devices as a liquid crystal composition. In order to create a liquid crystal composition that satisfies practical conditions, a large number of single liquid crystal compounds with diverse properties are required.
In some cases, compounds that do not themselves exhibit liquid crystal properties may be useful as components of liquid crystal compositions.

The present invention was made under these circumstances, and it is an object of the present invention to provide a ferroelectric liquid crystal element that has a wide operating temperature range, exhibits good alignment and memory properties, and exhibits high-speed response at room temperature.

(2) Means and operation for solving the problems An object of the present invention is to provide an alignment control layer on at least one of a pair of substrates each provided with a voltage application means, and to provide a ferroelectric liquid crystal layer between the pair of substrates. In the ferroelectric liquid crystal element, the ferroelectric liquid crystal contains at least one compound having an optically active group represented by the following formula (I), and the direction of the helical pinch induced in the nematic phase is represented by the formula (I). It contains at least one compound that is the opposite of the compound having an optically active group represented by, and at least a smectic C phase, a smectic A phase. This is achieved by a ferroelectric liquid crystal element characterized by exhibiting a nematic phase with a helical pitch of 20 μm or more.

(In addition, since the chiral smectic C phase and the non-chiral smectic C phase are thermodynamically considered to be the same, in the present invention, the smectic C phase is not distinguished between the two.
It shall be written as phase. Similarly, the chiral nematic phase and the non-chiral nematic phase are considered to be thermodynamically the same, so in the present invention they will be referred to as the nematic phase without distinguishing between them). (Left space below) (In formula (!), * indicates that the carbon atom is an asymmetric carbon atom.) The optically active group represented by formula (I) has cis form and trans form, Either can be used in the present invention, and both may be used in combination.

As the compound having an optically active group represented by general formula (I), a compound such as general formula (II) can be used. (II) (In general formula (If), A I , A ! and A3 represent a six-membered ring group which may have a substituent, and X is 10-
, -coo-, -oco- also represents a single bond, and Y1 and Yz are -COO-, -OCO- . -OCHz
．． -CHzO-, -CHzClh- . -CH
=CH-, -C301 or a single bond, Rl and R! represents a linear or branched alkyl group having 1 to 15 carbon atoms, and p. q and r are O or 1, and * indicates that the carbon atom is an asymmetric carbon atom. ) above formula (n
), R1 and R2 are methyl, ethyl. provil,
i-provil, butyl, i-butyl. Pentyl. l- or 2-methylbutyl. Hexyl, 1- or 3-methylpentyl, hebutyl, 1- or 4-methylhexyl, octyl, 1-methylheptyl, nonyl, 1- or 6-methyloctyl. Decyl, 1-methylnonyl, undecyl. 1
-Methyldecyl, dodecyl. Includes 1-methylundecyl. These alkyl groups may contain an asymmetric carbon atom in the carbon chain.

AI, At, and A3 of general formula (n) include a benzene ring,
Pyridine ring. Pyridazine ring, pyrazine ring, pyridazine ring, biperazine ring, cycloxane ring, dioxacyclohexane ring, bicyclo [2, 2. 2] Six-membered ring-containing groups such as octane rings and naphthalene rings are included, and one or more hydrogen atoms of these six-membered ring groups are fluorine atoms, chlorine atoms. Bromine atom, cyano group, nitro group. It may be substituted with a methyl group, methoxy group, etc.

Preferred examples of the compound represented by the above general formula (n) include a group of compounds represented by the following general formula. In the general formula below, e and f are each independently O or 1
and X1 is a halogen atom or a cyano group.

(The following is a blank space) Further, as a compound having an optically active group represented by the general formula (I), a compound such as the following general formula (■') can be used.

, X2 represents 101 or a single bond, RIG and R'' each independently represent an alkyl group having 1 to 15 carbon atoms or an alkenyl group having 2 to 15 carbon atoms, and d and f each independently represent O or l, and * indicates that the carbon atom is an asymmetric carbon atom.) The above general formula (n)-1 to (I
Typical examples of compounds of f)-7 and general formula (■') are shown in Tables 1 and 2.

In Tables 1 and 2, mp indicates the phase transition temperature, and the numerical value indicates C-I.

Note that the symbols for phase transition temperature indicate the following phases.

C: Crystalline phase 'SLII^: Smectisoc A phase SmC'': Chiral smectic C phase N: Nematic phase ■ Isotropic liquid phase SmX: Unidentified phase SmC: Smectisoc C phase (hereinafter blank) In the above general formula (II) Other examples of the represented compounds include the following general formulas (n)-8 and (II)-9.

(In general formulas (n)-8 and (n)-9, Rl, R
2 and X are R l , R ! of general formula (n). and has the same meaning as X) Specific examples of the above general formula (n)-8 include the following.

Further, specific examples of -a formula (II)-9 include the following.

Other specific examples of compounds that do not belong to the above general formula (II) or (■') and have an optically active group represented by formula (I) of the present invention include the following compounds. Other examples of compounds having an optically active group represented by formula (I) include general formulas (n) and (■') as well as azo. Examples include azoxy derivatives, fused polycyclic hydrocarbon derivatives, fused heterocyclic derivatives, chalcone derivatives, and cinnamic acid derivatives.

Among the compounds containing an optically active group represented by formula (I), the optically active compound represented by formula (II) is, for example, A′=
@． A2=@, x=single bond, YI=single bond,
Y! = single bond, p=i. Taking a compound where q=t, r=Q as an example, optically active epichlorohydrin and phenols are reacted in the presence of a base to obtain a compound of formula (Vl), which is then converted into a compound of formula (■>R'-CH(COOR).') g
(■) (In the formula, R l and R R have the same meaning as defined in the general formula (If), and R6 represents a lower alkyl group such as methyl or ethyl.) It can be obtained by the following reaction.

The method for producing the optically active compound represented by the above general formula (II) is described in detail in Japanese Patent Application No. 63-223345. Among the optically active compounds represented by the formula (I), the optically active compound represented by the general formula This can be achieved by reacting dianions of phenylacetic acid derivatives and then intramolecular cyclization.The synthesis method of the above general formula (■') is described in detail in Japanese Patent Application No. 1-42535.

Now, a compound containing an optically active group represented by formula (I) and an optically active compound represented by general formula (n) or (■') do not necessarily exhibit a liquid crystal phase. Further, even when shown, the temperature range of the phase series and Smectisocyan C phase is not necessarily practical. Therefore, it is much more preferable to use these compounds in combination with other compounds than to use them alone.

Compounds containing an optically active group represented by formula (I) and optically active compounds represented by general formula (n) or (■') are non-chiral smectic liquid crystal compounds or compositions, or chiral smectic liquid crystal compounds or compositions. By adding an appropriate amount to a compound, the spontaneous polarization of the compound can be increased and the response of the ferroelectric liquid crystal composition can be sped up. However, if the amount of these compounds added is large, the added compounds may crystallize in the ferroelectric liquid crystal composition, resulting in S
Since practical problems such as a decrease in the mC-=SmA transition temperature often occur, the amount added is preferably 0.1 to 20%, and more preferably about 0.5 to 10%. Now, as compounds containing an optically active group represented by formula (I) and compounds to be combined with the optically active compound represented by general formula (n) or (■'), the following general formulas (■) to
Compounds such as (X) can be used.

R'-Z'-B'-D'-8"-Z"-R@(■〉R'
-Z'-8'-D'-8"-D"-8"-Z"-R"
(IX) (hereinafter blank) (In the formula, B', B". and B3 are each independently,
Benzene ring, cyclohexane ring, bicyclo [2. 2
．． 2] Indicates a six-membered ring group such as an octane ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a piperazine ring, a dioxacyclohexane ring, and a naphthalene ring, and the hydrogen atom in these six-membered ring groups is fluorine. atom. chlorine atom,
Bromine atom, cyano group, nitro group. May be substituted with methyl group, methoxy group, etc. DI and D! are, respectively,
Single bond, or -COO-, -OCO-, -C}
I=CH-. -CmiC- , -C}I=CH-CO
O-, 10CO-(I{=CI-, -CHzCHt-
．． -OCHz, -CHZO-. -COS- or -SCO- represents a group. zl and Z2 are each a single bond or -coo-, -oco- . -o-
, -s- . -ocoo- or -CO- group. R7 and R@ each independently represent a linear or branched alkyl group having 1 to 15 carbon atoms, and an asymmetric carbon may be contained in the alkyl group. S represents an integer of 1 or 2. ) When using these compounds to prepare a material, it is necessary to synthesize various physical properties and characteristics of the ferroelectric liquid crystal composition so that good characteristics can be obtained when applied to a ferroelectric liquid crystal element. The author must take this into consideration. In the present invention, the liquid crystal temperature range. Tilt angle. In order to obtain a ferroelectric liquid crystal element that not only has good response characteristics but also particularly good coordination and memory properties, the ferroelectric liquid crystal should have at least a smectic C phase, a smectic A phase, and a helical pitch of 20 μm or more. It was prepared to exhibit a nematic phase. When a ferroelectric liquid crystal composite is produced to have such a phase series, when the ferroelectric liquid crystal element is produced and then cooled from an isotropic liquid state, the helical pitch in the nematic phase is 20 μm or more. The cell thickness of ferroelectric liquid crystal devices is usually 1. 5 to 8 μm>, uniform orientation can be easily obtained. When uniform orientation is obtained in the nematic phase, uniform orientation of the smectic A phase can be easily obtained when the device is further cooled, and good orientation of the smectic C phase can be obtained by further cooling. When good orientation is obtained, memory properties are also good.

In order to produce a ferroelectric liquid crystal composition exhibiting such a smectic C phase, a smectic A phase, and a nematic phase with a helical pitch of 20 μm or more, the direction of the helical pinch induced in the nematic phase must be determined by the formula (I ) or an optically active compound having the opposite orientation to the optically active compound represented by general formula (II) or (■'), as shown in formula -(
A compound containing an optically active group represented by I) or the general formula (
This can be achieved by using a combination of optically active compounds represented by n) or <■') in an appropriate ratio. Various methods can be used for mixing, including a method of repeating trial and error so that the helical pitch of the nematic phase becomes 20 μm or more. Next, an example will be shown. It is known that there is a linear addition law such as equation (XI) regarding the pitch of the nematic phase (J.E. Adams and W.E.
L. lass. Mol. Cryst.
Liq. Cryst. +lfi+ 33 (I97
2)).

1/P=Σ (Ci/Pi) (XI)
(However, ΣCi=L P is the pitch of the mixed liquid crystal, and Ci is the weight concentration of each component with a unique pitch Pi.) Therefore, first, various optically active substances are added to the liquid crystal compound or composite compound exhibiting the nematic phase. is added to measure the pinch of the nematic phase, estimate the characteristic pitch Pi of each component, and then use this value to create a ferroelectric liquid crystal U with a pitch of nematic phase of 20 μm or more. The concentration of each power was adjusted as follows. Examples of optically active compounds used for such pitch adjustment include general formula (■). (IX) and (X
) of the compounds represented by R? A compound having an optically active group in either or both of , Rl can be used. In addition, when using these compounds, if possible, the direction of the spontaneous polarization induced in the smectic C phase should be determined by the formula (
A compound containing an optically active group represented by I) or the general formula (
It is preferable that it is the same as the optically active compound represented by II) or (■') and has a large value. This is because it is generally said that the larger the spontaneous polarization value of a ferroelectric liquid crystal composition, the faster the response. From this point of view, the spontaneous polarization induced in the smectic C phase for a compound containing an optically active group represented by formula (I) or an optically active compound represented by general formula (n) or (■') An example of a compound in which the directions of the helical pitch are the same and relatively large, and the direction of the helical pitch induced in the nematic phase is opposite is a compound having an optically active group represented by the general formula (III).

-Z-CH-R'' (I[I) G (In general formula (III), Z is -coo-, -oco-.
-o-. -co-, -OCHg-. -OCHgCHg
one or a single bond, R3 is a phenyl group having an alkyl substituent having 1 to 15 carbon atoms, or each has 1 to 15 carbon atoms.
represents a group selected from linear or branched alkyl groups, alkyloxy groups, and acyloxy groups, and the alkyl in the above alkyl group, alkyloxy group, and acyloxy group has a halogen atom or a cyano group as a substituent. It may contain -o-, -coo-, double bond or triple bond, and may further contain asymmetric carbon. G is a halogen atom, -CN-. -CH
s-,-CH! F. -CHFt or -CF3, *
indicates that the carbon atom is an asymmetric carbon atom. ) As a preferable example of the compound having an optically active group represented by the above general formula (I[[), an optically active compound represented by the following general formula (XII) can be mentioned. Compounds that can be made are not limited to these compounds.

R'X'- (A'-Y') a- (A'-Y')
b- (A') c-Z-CI-R3(X II )G (in general formula (Xn), Z, R'.G and *c general formula (I
II) Z, R3. Indicates the same meaning as G and *, and A
4, A% and A1 represent a six-membered ring group or a five-membered ring group which may have a substituent, and X3 is -o-, -oco-
or a single bond, Y3 and Y4 are -coo-, -o
co-, -OCHz-, -CHtO-, -CH=CII
-, -CEC-, -CHZCHZ represents one or a single bond,
R9 represents a linear or branched alkyl group having 1 to 15 carbon atoms, and a, b and C are 0 or 1. ) Above A4, AS. The six-membered ring-containing group of Ah is represented by the general formula (■). B' of (IX). Groups similar to BtomiB3 can be mentioned, and examples of the five-membered ring group include, for example, the above general formula (
Preferred examples of the compound represented by XI) include compounds represented by the following general formula. In the general formula below, e and f are 0 or 1, and h is 1 or 2.

(XII)-1 Specific example R' = n-C. H. ．． , f=l, e=Q, G=CH3
, R3=n C6 Hl3 compound R9=n-Cs
Hl,. f=1, e=1, G=CF:+, R”=
Compound R9=n-C.CHz COOCt HS. Hl
? , f-1, e=1, G=CF3, R'=n C
h Compound R' of Hl3 = n-C+oHz+, f=o
, e=1, G=CF3, R'=n Cb Hl3
The compound R' = n Cm H171 f = 1
, e = 1, G = CHFz , R3 = n Ca
Hat's compound R""n Cll Hl? l
f=L 6=l, G-CHz F,R'”
n Cm Hat compound (X. Yoshino, e
tal. , J. Appl. Phys. ．． 26,L77
(I987) and Suzuki et al., 15th LCD Symposium, 3A.
17 (I989))q (XII)-2 Specific example R""n C? HIS, f=1, e=1, G=C
H3, R' = n Cl, HI: Compound of l (XI
I) -3 Specific example R' =n C6 H+? ．． f=1, e=o. h=2
．． 0”CH3 .R” = Ct Hs compound R9 =
n-CIIHZ31 G=CH. , R'=C, R"=n Cll Hl?, G=CH3
, R'=C, f=1, e=0. H5 compound f=0, e=l. H, a compound of h=2. h-1. G (XII)-4 (I. Sage, et al., Ferroelect
rics, 85+351 (I988)) Specific example R9=n-CIIH11 f=1. G=CH,,R3=
Compound R' of n CB Hlv -n C g H l 9 1 f = 1
+ G = C N + R3 = CH (CH3)z Compound G (Xn)-5 Specific example R9 C8 Hl7+ f =0, G = CH. Compound q (XI[) 6 with R3 = n C4 H9 Specific example R9 = n − C, H17, f=1, G=CH. R3'' C z H5 compound q (XI)-7 Specific example R9 = n Cs HI?+ f=0, G=CH1 R”=n C6 Hl3 compound (Xn) -8 Specific example R'1 = n- C, H1h f = 1, e = 1, G's C H 3 R3 = n-C6 Hl3 compound R9 = n-C, H1,, f = 1, e = 0. G= * (T.Sakurai, et al., J.Che+w.Soc..Con+mun+
978 (I986)) (X II) 9 (E: H, F) Specific example R” =n-C@Hl?+ f = 1, G=
CH3 *R' =n Cb H+s compound G (XI[) Specific example R'' =C6 FtsCHt CHz ,G=CH,,
R3=n-C. H, compound (XII)-11 (E:H, F, Cl, Br, CN) (
Z''' :-O-.-Co〇1) (X.Te
rashin+a,et at. +Mol. Cryst
+Liq. Cryst. +Top 41. 237 (I98
6). Ichihashi, et al., Proceedings of the 13th LCD Symposium, 50 (I987)
)K. Furufawa+et al. , Ferroelectrics+cause, 451 (I988)) Specific example R" =n C+oHz+. E=H, Z
Compound F (Xll) -12 (J. Bmelburg, et al.. 12th Int. LC Con f. FB-18 (I988)) ()i3 (XII) -13 of 3' = COO- R3 = n C6 I11. (A, Yoshizawa, et al. + J. Appl. Phys.. 28, L1269 (I989)) Specific example R9 = n-(:, @ Hl71 R3 C6 HI3 compound (XII) 1 4 (E: H, Br, CN) (Yoshida, et al., 15th Liquid Crystal Symposium. IAOI (I989)) (XII)-15 (Miyazawa, et al., Proceedings of the 14th Liquid Crystal Symposium. 52 (I988)) Specific example R' = Compound α (Xll) l 6 of n − C, Hl3・R3 = n Ca H, (C.73 (hierske, et al.. 2nd Int. Conf. FLC. p-83 (I989)) Specific example R9 = n -C, H l?
I988)) Specific example R9? n C l O H! ■ R3 =n-C. Compound (XI)-18 of H9 (M. Koden, et al,, Mol.C
ryst. Liq. Lett. ．． 6 +197(
I989)) Specific example R' =n Cs Hut R3' =n Cl
1 }{l? The ferroelectric liquid crystal compound of the present invention has the above general formula (II
In addition to the compound having an optically active group represented by I), optically active compounds represented by the following general formula can be used in combination.

(XII[) (In the above general formula (XI[[), R3, R',
ZIA'l^5, A', Y'+Y', a, b+c and *
have the same meanings as those in the general formula (XI[) above.
) Examples of the optically active compound represented by the above general formula (XII[) include compounds represented by the following general formula.

(XI[I)-1 is shown. 〉 (DM, Walha, et.al., J.Aa+.Che+s.Soc..110.8686 (I988)) Specific example z=-oco- R3 Demand n-C5 1"III compound Z=-OCR ! R3=n C5 Ht+ compound (X ■) (In the general formula (X rV), Y3 represents -COO,
Y4 is -Coo, OCO, OCHz-
and y' is -coo-. -o-, E, H
, denotes CI. ) (J. Nakauchi, et al,, J. App
l. Phys. , 2B, L1258 (I989) ,
Ikemoto, et al. 15th LCD Symposium. IAO5 (I989
)) Specific example R" -n C+oHz+.Y" = Coo
,E=H. Y' − OCHt +, Y'
"COO-R3"n Compound of C & Hl3 In the ferroelectric liquid crystal composition of the present invention, a compound having an optically active group represented by general formula (I) and a compound represented by general formula (n) or (■') optically active compound and the general formula (III
) and a compound having an optically active group represented by the general formula (X
Examples of compounds that can be combined with the optically active compound represented by n) include compounds represented by the following general formula (IV) and compounds having a fluoroalkyl group represented by the general formula (V). can. (In the general formula (I'/), R4.R% each has 1 carbon number
~15 linear or branched alkyl groups or alkyloxy groups. ) (CHz) - CI%Fz-t (V
) (In general formula (V), m is 1 or 2, and n is 2-1
It is an integer of 2. ) The above general formula (rV). The compound represented by (V) is known as a precept for controlling liquid crystals, and there are various compounds as shown in Examples. In addition to the compounds used in the Examples, the compounds having a fluoroalkyl group represented by the general formula (V) include the following compounds. Clh CI{3 Next, the ferroelectric liquid crystal element of the present invention will be explained. FIG. 1 is a sectional view showing an example of a liquid crystal element using the ferroelectric liquid crystal composition of the present invention.

FIG. 1 shows an example of a transmissive display element, and 1 and 2 are insulating substrates. 3 and 4 are conductive films. 5 is an insulating film. 6 is an alignment control layer, 7 is a sealant, 8 is a ferroelectric liquid crystal, and 9 is a polarizing plate.

Transparent substrates are used as the insulating substrates 1 and 2, and usually glass substrates are used. Insulating substrates 1 and 2 contain I n O:l and S n 02., respectively. I.T.
A transparent electrode 3.4 in a predetermined pattern is formed of a conductive thin film such as O (Indium-Tin Oxide).

An insulating film 5 is usually formed thereon, but this can be omitted in some cases. The insulating film 5 is, for example, S i
Ot. S i N X, A I! Inorganic thin films such as 03. Borii ξ de. Photoresist resin. Organic thin films such as polymeric liquid crystals can be used.

When the insulating film 5 is an inorganic thin film, it may be formed using a vapor deposition method, a sputtering method, or a chemical vapor deposition method (CVD).
Formation can be determined using the method such as Deposition method or solution application method. In addition, when the insulating film 5 is an organic thin film, a spinner coating method may be applied using a solution containing an organic substance or a precursor solution thereof. Dip coating method, screen printing method. A method in which it is applied using a roll coating method, etc., and then cured and shaped under predetermined curing conditions (heating, light irradiation, etc.). Alternatively, it may be formed by vapor deposition, sputtering, CVD, etc.
It can also be expressed using the B (Langus+uir-Blodgett) method. An orientation control layer 6 is formed on the insulating film 5. However, if the insulating film 5 is omitted, the conductive films 3 and 4
An orientation control layer 6 is formed directly on top of the film. The orientation control layer may be an inorganic layer or an organic layer. When using an inorganic orientation control layer, oblique vapor deposition of silicon oxide is a commonly used method. Alternatively, methods such as rotary evaporation can also be used. When using an organic orientation control layer, nylon, polyvinyl alcohol, polyester, etc. can be used, and this is usually rubbed. Also, polymer liquid crystal. Orientation using LB film,
Orientation due to magnetic field. Orientation using the spacer edge method is also possible. Also, S i O z + S I N
x etc. by vapor deposition method. Subatta method. It is also possible to form a shape by CVD method or the like and rub it on top. Next, two insulating substrates are bonded together and liquid crystal is injected to form a ferroelectric liquid crystal element.

Although the ferroelectric liquid crystal and liquid crystal element of the present invention are described above as a switching element with one pixel in FIG. As shown in the figure, the wiring on the upper and lower substrates is combined in a matrix pattern. Such matrix-type liquid crystal elements can be manufactured using various driving methods that have been proposed so far (
For example, Wakita, Uemura, Onishi, Ohba, Furubayashi, and Ota. Na
tional Technical Report, 3
3. 44 (see I987)), the S section can be changed. (E) Example of combining a compound having the formula (I) 5.55 g of R- (-) one epichlorohydrin (optical purity of 99% or more) and 4-(trans-4- n-pentylcyclohexyl)phenol2.
46g of benzyltriethylammonium chloride and 0.04g of benzyltriethylammonium chloride was stirred at 60°C while adding an aqueous solution of sodium hydroxide (NaOH O.45g.Water 15mJ!)
was added dropwise over 20 minutes, and the mixture was further refluxed for 1 hour. The reaction solution was cooled to room temperature, extracted with ether twice, washed once with saturated brine, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain (S)-2,3-epoxyprobyl 4-(
1.8 g of trans-4-n-pentylcyclohexyl) phenyl ether was obtained.

(α) 3' +4.4 4° (C=1.36, CJ
Cl! 2) NMR (C D C I 3 ) δ
: 0.4 5 ~ 2.5 0 (2 1 H,
m) 2.5 0 ~ 3.0 0 (2H. m) 3
．． 1 5 ~ 3.5 0 (I H. m) 3.7
0 ~ 4.30 (2H, m) 6.79
(2H, d, J = 9.0Hz) 7.09 (
2H. d, J = 9.0 Hz) 224 mg of 50% by weight sodium hydride suspended in mineral oil was dissolved in dry ether.
After washing twice, 10 ml of dry tetrahydrofuran was added. While stirring this suspension at 40°C, 1.07 g of dimethyl n-butylmalonate was added dropwise and stirred for 5 minutes. 1.41 g of 4-n-pentylcyclohexyl) phenyl ether was added dropwise, followed by centrifugal stirring for 20 hours. After returning the reaction solution to room temperature, 4N hydrochloric acid was added dropwise until the pH reached 1. After that, ether extraction was performed twice, and saturated brine was added for 1 hour.
After washing twice, the solvent was distilled off under reduced pressure. The residue was separated and purified by silica gel column chromatography to obtain 500 mg each of (2S,4S) and (2R.4S) T-lactone derivatives represented by the following chemical formulas. 440 mg was obtained.

Among these, the properties of the (23.4S) body are as follows. (23, 4S) Body phase transition temperature (α)i! '+33.45° (C=0.6 5 8.C
HgClz) NMR (CDCl3) δ: 0.88 to 1.98 (30H.
m) 2.3 8 to 2.6 7 (3H, m)
4.0 7-4.1 3 (2 H, m) 4.6
7 ~ 4.7 3 (I H, m) 6.8 3
(2H, d, J = 8.3H
2)? ．． 1 2 (2H, d, J
=8.3HZ)IR (KBr) 17
62 cm-' Elemental analysis (as C z h Ha. O) C H Theoretical value (%) 77.95 10.07 Actual value (%') 77.91 10.12 Synthesis example 2 The following is the raw material phenol derivative Compound represented by the chemical formula 2. 50 g, same R-(-)-epichlorohydrin as in Example 14.
25g and penzyltriethylammonium chloride 2
Dissolve 0 mg in 3 ml of dimethylformamide,
A 24% by weight aqueous sodium hydroxide solution (1.2 equivalents) was added dropwise at 0°C. After reacting at the same temperature for 40 minutes, the reaction solution was returned to room temperature, then extracted with ether, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.62 g of S-glycidyl ether represented by the following chemical formula.

mp 90℃ (α) W + 4.4 4” (C= 1.0
1. CHzClt) NMR (CD C i'
3) δ: 0.5 0 to 3.0 0 (I 9
H, m) 3.1 0 to 3.5 0 (I H,
m) 3.8 0 to 4.3 0 (2H, m) 6
．． 75 to 7.60 (8 H.m) 370 mg of the S-form glycidyl ether obtained above, 442 mg of diethyl n-propylmalonate. Potassium t-butoxide 1 3 4 mg and t-butyl alcohol 3 m
The mixture was stirred under reflux for 10 hours. The reaction solution was returned to room temperature and 4N hydrochloric acid was added to adjust the pH to 1, followed by washing with water and methanol to obtain white crystals. This was separated and purified by silica gel chromatography to obtain 240 mg of the (2S.4S) form of the γ-lactone derivative represented by the following formula and (2R
, 4S) body (140 mg) was obtained.

Among these, the properties of the (2S.4S) body are as follows.

(2S, 4S) body U phase transition temperature 2C [α)o+32.67 ° (C=1.081.NMR
(CDCls) δ: 0.70 to 3.00 (27H.
m)? HCl,) 4.0 0~4.2 5 (2H, m) 4.4
0 ~ 4.8 5 (l H, m) 6.6 0 ~
7.6 0 (8H, m)IR (KBr)
1762cm -1 (C-0) Combined example 3
~6 In the same manner as in Example 2, each of the following chemical formulas (23.
43) A T-lactone derivative of the compound was obtained. Combination Example 7 1.01 g of the compound represented by the following chemical formula as a raw material phenol derivative, R- (1) monochlorohydrin 2. Same as Combination Example 1.
01g and penzyltriethylammonium chloride 1
Mix 5 mg and heat to 70°C, add 24% by weight to this.
650 mg of an aqueous sodium hydroxide solution was added dropwise. 7
After stirring at 0°C for 2 hours, the reaction solution was allowed to reach room temperature, then extracted three times with chloroform and dried over anhydrous magnesium sulfate. The residue obtained by evaporating the solvent under reduced pressure was recrystallized from hexane to obtain 380 mg of S-form glycidyl ether represented by the following chemical formula. mp 65℃ (α)F+1.90°(C-0.46.CHx Cl
t>NMR(CDCl3)δ:
0.6 ~ 3.0 (I9H, m) 3.2
~3.6 (IH, m) 3.9~4.5 (2H, m) 6.99 (2H, d, J=9.0
Hz) 8.36 (2H. d, J=
9.0Hz) 8.55 (2H, s) 320mg of the S-form glycidyl ether obtained above, n
-dimethyl hexylmalonate 406 mg. potassium t-
6 mg of ptoxide 1 1 6 mg tert-butyl alcohol 3.
The solution was dissolved in 5 mj and stirred under reflux for 6 hours.

The treatment after the reaction was the same as in Example 2, and a mixture of diastereomers of T-lactone derivatives ((2S,4S)/
(2R.4S)=9/1) 270 mg was obtained. This mixture was further purified to obtain 210 mg of a (2S.4S) T-lactone derivative.

(2S, 4S) body N M R ( C D C 1 s ) δ: 0.
8 5 ~ 0.9 0 (6 H, m) 1.2
7~1.6 4 (2 1 H.m) 1.82~
1.95 (2H, m) 2.4 7 ~ 2.7 0 (4H. m) 4.1
3-4.2 5 (2 H, m) 4.7 0
~4.7 7 (L H, m)6.9 9
(2H, d, J=9.1Hz)8.
37 (2H, d, J=8.9
Hz) 8.57 (2H, s) IR (Nujol) 1778 cm-' Synthesis Example 8 4-(4-n-octylphenyl>phenol 2.8
2 g of boron trichloride and 40 mf of 1.2-dichloroethane were added to a suspension consisting of 40 mf of 1.2-dichloroethane and 6 ml of a 2M solution of boron trichloride in 1.2-dichloroethane under water cooling, followed by 0.82 ml of methyl thiocyanate and 1.2 mf of aluminium chloride. 33 g was added. The mixture was stirred at room temperature until the aluminum chloride was dissolved, and then stirred at 80°C for 3 hours. After cooling, add 3 ml of 4N aqueous sodium hydroxide solution to 75-80°C.
The mixture was stirred for 30 minutes. After cooling, the reaction solution was washed with methylene chloride, and the aqueous layer was adjusted to pH=2 with 6N hydrochloric acid, and extracted with ether. After drying the extract, the ether was distilled off under reduced pressure, and the obtained crude crystals were purified by silica gel column chromatography to obtain 4-(4-n-octylphenyl>-2-cyanophenol) represented by the following chemical formula. 0.3 g was obtained.

mp 93℃ NMR (CDC 1z) δ: 0.8 8 (3H, t,
J=6.811z) 1.2 7~1.3 2 (I
0 H, m) 1.6 0 ~ 1.7 1 (2
H, m)2.6 4 (2H, t
, J=7.7Hz)6.24 (IH
, broad S) 7.02 ~ 7.70
(7H.m)1. R(KBr) 3288cm-'
(νO-H)2 2 4 0 cm-' (νC=N)
To a solution consisting of 1.9 g of the above 4(4-n-octylphenyl)-2cyanophenol and 40 ml of t-butyl alcohol, 832 mg of potassium t-butoxide was added.
and then add R-(-)epichlorohydrin 2. as in Example 1. 5 ml and 100 mg of 4-(N,N-dimethylano-pyridine) were added and stirred at room temperature for 2 days.The mixture was concentrated under reduced pressure, water was added to the residue, extracted with ether, and the extract was dried. The crude product obtained by distilling off the ether from the extract was purified by silica gel column chromatography to obtain 750 mg of S-form glycidyl ether represented by the following chemical formula.

mp 54℃ [α) B' + 7. 8 8 ° NMR (C D C l s δ : O.SS 1.20-1642 1.5 5-1.67 (C=1.0 1, CHz Clt)) (3H, t, J=6.6Hz ) (IOH, m) (2H, m) 2.64 (2H, t, J=7.7H
z) 2.8 4 ~ 2.9 7 (2 H, m)
3.3 9 to 3.4 3 (I H, m)4.
1 2 ~ 4.4 5 (2 H, m) 7.0
5 ~7.7 7 (7H, m)IR (K
Br) 2224 cm-' (νc=N) 363 mg of the above S-form glycidyl ether, 30 3 mg of n-probyl diethyl malonate, 15 potassium t-butoxide
Mix 7mg and 10mf of t-butyl alcohol and make 6
Stir at reflux for an hour. Return the reaction solution to room temperature, add water and dilute with 4N
After adjusting the pH to 2 with hydrochloric acid, the mixture was extracted with chloroform. The oily substance obtained from the extract was separated and purified by silica gel chromatography to obtain 33 mg of (2S,4S) form and 25 mg of (2R,4S) form of γ-lactone derivatives represented by the following formulas.

(Left below) (2S. 4S) Body 0 Phase transition temperature 86℃ C I (α) g' + 3 1.8 3 ” (C= 1
．． 0 9, CHtCIZ) NMR (CDCl,
) δ: o. sa (3H, t, J=6.6Hz
)0.9 7 (3H, t, J=T
．． IHz) 1.2 5-1.3 2 (I 0H,
m) 1.4 1 to 1.5 8 (3H, m)
1.59 ~ 1.66 (2H, m) 1.8 5 ~ 2.0 7 (2H, m) 2.5
5 ~ 2.7 8 (4H, m) 4.31
(2H, d, J=4.3Hz) 4.7 4-4
．． 8 3 (I H, m) 7.0 0 ~ 7.7
7 (7 H.m)IR (KBr)
2232cm-' (νc=N)1 7 6 8 cm
-'<v C=O) (2R, 48 bodies) O Phase transition temperature 80℃ C I (cr)? +' + 1 8.2 6' (C=
0.8'7, Cl{2(JZ)NMR (CD
Cl,) δ: 0.88 (3H, t, J=6.8Hz
)0.98 (3H, t, J=7.1Hz)
1.2 5 to 1.2 7 (I2H, m)1.
45~1.56 (2H, m) 1.6 0~1.6 2 (IH, m) 1.8
5-1.9 5 (I H, m) 2.1 2
~2.2 2 (L H, m)2.5 6~2.
6 7 (3 H, m) 3.0 5 ~ 3.1
0 (I H, m)4.19 (I
H, dd, J=3.3Hz, 10.3Hz) 4.3 7 (I H, dd d,
J = 3.311z, 10.3Hz) 4.8 4 - 4.8 9 (I H, m>7.
0 0 ~ 7.7 7 (7 H, m) I R
(KB r) 2 2 3 2 cm-' (
y C=N)1 7 6 8 cm-' (νC=O
) (blank below) Example 9 Benzyl 4- (4' -n-octyloxyphenyl)-2-fluorophenyl ether 5 g, 5% Pd-C
(52% water content) 2.5g and ethyl acetate 209m
A mixture of N was heated under a hydrogen atmosphere at room temperature at 2 kg/cm
Shake for hours. After completion of the process, the solid was separated, the solvent was distilled off from the liquid, and the obtained solid was recrystallized from benzene-hexane to obtain n-octyloxyphenyl)-2-fluorophenol represented by the following chemical formula.3. 71 g was obtained.

F mp 115.5°C NMR (CDC Qs) δ: 0.89 (3H, t, J=
6.8Hz) 1.2 ~ 1.5 (I 0H,
m) 1.7 to 1.8 5 (2H, m)3.
9 8 (2H, t, J=6.6H
z) 5.1 8 (IH, d, J-
3.9}1z) 6.9~7.4 (7H, m) I R (KB r) 3 5 4 4 c
m-'(J'OIl) above 4- (4' -n-octyloxyphenyl)=2-fluorophenol 2.
68 g and 60 mj of t-butyl alcohol!
potassium t-poxide in a solution consisting of 1. 1 2
Then, 3.3 ml of R-(-)-epichlorohydrin and 50 mg of 4-(N.N-dimethylano)pyridine were added, and the mixture was stirred at 40°C for 1 day. did. The mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with chloroform. After washing and drying the extract, chloroform was distilled off, and the obtained crude bottom material was purified by silica gel column chromatography, and the S-glycidyl ether represented by the following chemical formula was extracted from the dichloromethane eluate. 17 g was obtained.

mp 96℃ [α] So+4. 6 5” (C÷1.0 0, CHz Cl!) N M R
(C D C l s ) δ: 0.8 9
(3H, t, J = 6.8Hz)1.
2 ~1.55 (I0H.m) 1.7 4 ~1
．． 8 5 (2H, m) 2.78
(IH, dd, J=2.8.5.0 Hz) 2.9 1 (IH, t, J=5.0
Hz) 3.3 b~3.4 2 (IH, m)
3.98 (2H, t, J=6.6H
z) 4.08 (IH.dd, J=5.5
, 11.3Hz) 4.31 , (IH, dd, J=
3.3.11.3Hz) 6.9 ~7.45 (7H, m) MS (
El) m/z 372 (M”) 650 mg of the above S-form glycidyl ether, 529 mg of n-probylmalonate diethyl, 274 mg of t-butoxide, and 2Qmj of t-butyl alcohol!
The mixture was stirred at reflux for 1.5 hours. The reaction solution was returned to room temperature, water was added and the pH was adjusted to 3 with 2N hydrochloric acid, and the precipitated solid was collected. Washed with water and dried. This product was separated and purified by silica gel column chromatography followed by normal phase silica gel high performance liquid chromatography to obtain T
- 10 mg of (2S.43) form and 10 2 mg of (2R.43) form of -lactone derivatives were obtained.

(2S, 4S) body υ phase transition temperature [α) g' + 3 8. 3 5 @(C”1.0
2. CH! Clt) NMR (C D C
1 s ) δ : 0.8 9 (3
H, t, J=6.7Hz) 0.9 7
(3H, t, J-7.1Hz) 1.2
~1.6 (I3H, m)1.7
4-2.0 (4H, m) 2.4 5-2.6
(I H, m)2.6~2.7 5 (
I H, m) 3.9 9 (2H,
t, J-6.6Hz) 4.1 5 ~ 4.3
(2H, m) 4.7 ~ 4.8 (L
H, m) 6.8-7.5 (7H, m)I
R (KBr) 1764cm-' (νc=
o) MS (El) m/z 456
(M”) (2R, 43 bodies) U Phase transition temperature 1 0 0℃ C ■ [α) g'+21.51 ・ (C=0.7 9. CHt C It) NMR
(CDClz) δ: 0.8 9 (3 H, t,
J-6.8Hz) 0.98 (3H,
t, J=7, IHz) 1.2 ~ 1.55
(I3H.m) 1.7 5-1.9 (3H,
m)2.0 5-2.2 (IH, m)2
．． 4 5 ~ 2.5 6 (L H, m) 2.8
5 ~ 2.9 5 (L H. m) 3.99
(2H, t, J=6.6Hz)4
．． 15 (IH. dd. J=3.
5.10.3Hz) 4.26 (IH. dd. J=3
．． 5.10.3Hz) 4.7 5 ~ 4.8 5 (I H, m) 6.
9 ~7.4 (7H, m)IR (K
Br) 1770cm-' (νc=o)M
S (El) m/z 456 (M”
) Synthesis Example 10 Synthesis of (S)-n-hexyl glycidyl ether 40 g of 50% caustic soda, (S)-(+)-epichlorohydrin (optical purity of 99% or more) 24 g and tetrabutylammonium hydrogen sulfate 400 mg of the mixture was cooled to 20-25°C - hexanol 6
ml was added dropwise. After the reaction solution was further stirred at the same temperature for 3 hours, water was added and the raw bottom material was extracted with ether. (S)-n-hexyl glycidyl ether by rectifying the extract under reduced pressure3. 20 g was obtained. [α) p 2.45° (C-1.0 0 5.CH
t C1t) bp 52℃/ 4 mm H gN
MR (CDC1,) δ: 0.89 (3H, m) 1.2 ~ 1.4 (6H, m) 1.58
(2H, m) 2.58 (IH, dd) 2.77 (IH, dd) 3.12 (IH, m) 3.36 (IH. dd) 3.48
(2H, m) 3.70 (IH, dd) 4 (4'-
n-heptyl〉-biphenylacetic acid combination 4-acetyl-4/-n-heptylbiphenyl 10.8
5g, sulfur 2. 3 6 g to 20 ml of morpholine
The mixture was refluxed under stirring for 9 hours. Caustic soda 29% in the reaction solution
．． 5g. 80ml of water and 100ml of ethanol! After stirring for 9 hours, the reaction solution was transferred to water and acidified with hydrochloric acid, and the precipitated solid was collected by filtration to obtain the crude product 13.51.
I got g. The crude product was purified by silica gel column chromatography to obtain the desired product 8. 29 g was obtained. mp 154-162℃ IR (Nugeol) 1724cm-'N M R
(C D C l s ) δ: 0.8 B
(3H, m) 1.2~1.4 (8H.m
) 1.64 (2H, m) 2.63 (2H, t) 3.68
(2H,s) 7.23 (2H,d) 7.33 (2H,d) 7.48 (2H.d) 7.54 (2H,d) Diisoprobylamine cooled to -78°C 50 5m
g and 15% n in a solution of 10 ml of tetrahydrofuran.
3 ml of a hexane solution of -butyllithium was added dropwise, the temperature was gradually raised to 0° C., and the mixture was stirred for 1 hour. A solution of 682 mg of 4-(4'-n-heptyl)monobiphenylacetic acid and 3 ml of tetrahydrofuran was added dropwise to this reaction solution and stirred for 1 hour. The reaction solution was cooled to -78°C, and the above-mentioned combined (S) 1 n-hexyl glycidyl ether 4 4 5 mg and tetrahydrofuran lmj? solution was added dropwise. After the temperature of the reaction solution was gradually raised to room temperature and stirred for 6 hours, water was added, the solution was further acidified with hydrochloric acid, and the raw bottom material was extracted with chloroform. Dry benzene and a catalytic amount of concentrated sulfuric acid were added to the extract, and the mixture was heated and stirred for 6 hours while allowing the benzene to flow out little by little. After cooling, benzene was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain a T-lactone derivative (2S,
4R) and (2R,4R), respectively, at 401 mg and 4
6 5 mg was obtained.

(2S. 4R) Body O Phase transition temperature [α]”: −2.1 7 @(C=1.0 7.NM
R (CDC1s) δ: 0.86-0.9l 1.29-1.61 2.28-2.42 2.6 1-2.76 (6H,m) (I8H.m) (IH,m) (3H.m) C Hz C l z) 3.52 3.6 1~3.75 3.92 4.6 2~4.67 7.24 7.35 7.48 7.57 (2R, 4R) body (2H.t.J=6.6011z)(2H.m
) (IH, dd, J=9.16 Hz, 1 2. 0 9 Hz) (IH, m) (2H, d, J=8.0 611z) (2H,
d, J=8.4211z) (2 H, d,
J = 8.4 21lz) (2H, d, J
=8.0 611z) Phase transition temperature 22 [α), -37.95' (C=1.0 0 3,
NMR (CDClz) δ: 0.8 6-0.9 0 (6 H. m
) CH2 C12 ) 1.2 9 to 1.6 0 (I 8 H, m)
2.4 5 to 2.5 7 (I H. m)2.
6 1 ~ 2.7 4 (3H. m) 3.51
(2H, t, J=6.68H
z) 3.6 0 to 3.7 5 (2H. m)4.
0 9 (I H, t, J=9
．． 35Hz) 4.74~4.78 (IH,
m)? ．． 24 (2H, d,
J=8.06}1z)7.33 (
2H. d. J=8.43tlz)7.48
(2H, d, J=8.43Hz)
7.57 (2H, d, J=8
．． 06Hz) Synthesis Example 11 (Synthesis of compound having formula (nI)) Preparation of (R)-4'-n-octyloxy-biphenyl-4-carboxylic acid-1-trifluoromethylnonyl ester 4'-n -0.5 g (I.5 mmol) of octyloxy-biphenyl-4-carboxylic acid and 4 g (I.5 mmol) of phosphorus pentachloride.
9 mmol) and heated to react.

POC&'! by vacuum distillation! and remove excess phosphorus pentachloride 4 / n-octyloxy-biphenyl 4
-Carboxylic acid chloride was obtained. Dissolve this in pyridine, add 0.30 g (R)-1-}refluoromethylnonanol (I.5≧limole), and dissolve at room temperature for 12
After standing for a while, the mixture was heated to 80° C., kept as it was for 3 hours, and then cooled to obtain a reaction mixture. The reaction mixture was poured into aqueous HCl and extracted with diethyl ether. The diethyl ether layer was washed with an aqueous NaHCO3 solution, then with water, and dried over Na, SO4. The diethyl ether was distilled off, and the residue was purified by column chromatography (solvent: chloroform) to obtain a liquid object. Obtained something ([α)
"=-2 1.8" (CHCl, )).

The compound having an optically active group represented by formula (I) obtained in the above Synthesis Example 1-1 0 is used as compound N in the following examples.
It was used as al~Ilh6, Ilh36~42. In addition, the compound having an optically active group represented by the formula (I[[) obtained in Kwei Example 11 was used as compound 11kL43. (F) Examples Example 1 A nematic liquid crystal composition (I) having the composition shown in Table 1 was prepared. A Cano-type wedge-shaped cell was created using two glass substrates that had been subjected to horizontal alignment treatment and their surfaces were rubbed in opposite directions, and the thickness of each part of the cell was measured. A Nematisoku liquid crystal composition was prepared by adding about 1% by weight of each of the compounds shown in Table 2 to the liquid crystal composition (I),
It was injected into a Cano-type wedge-shaped cell. This cell is installed between two polarizing plates whose polarization directions are orthogonal to each other,
Observe the disclination line. The helical pitch of the injected nematic liquid crystal composition was determined based on the value of the cell thickness at the position where the disclination line appeared. (X) Using the relationship of formula, 1/P of each compound
It was converted into an estimated value of i.

These values are shown in Table 2.

Example 2 30 of each of the compounds shown in Table 3 was added to liquid crystal composition (I).
A liquid crystal composition exhibiting a nematic phase was prepared by adding % by weight of the compound.

Table 1: Nematic liquid crystal composition (I) The compounds shown in Table 3 are compounds for which the direction of the helical pitch of the nematic phase is already known. On the other hand, 1 to 30% by weight of each of the compounds shown in Table 2 was added to the liquid crystal compound (I).
We have also created a liquid crystal composite that exhibits a nematic phase by adding it. Nematic liquid crystal compounds made from the compounds in Table 3 and the second
Liquid crystals prepared from the compounds shown in the table were brought into contact with each other on a slide, and this was observed using a polarizing microscope. The direction of the helical pitch induced in the nematic phase by the compounds in Table 2 was determined by whether or not a schlieren structure, which appears only when the helical pitch is very long, appeared in the area where the two were in contact. The results are shown in Table 2.

Example 3 A liquid crystal assembly (2) shown in Table 4 was prepared.

This liquid crystal composition (2) is a non-chiral smectic C liquid crystal Ml composition containing no optically active compound. To this liquid crystal composition (2), 2% by weight of each of the compounds shown in Table 2 was added to prepare a Chiral Smectifuku C liquid crystal composition.

An ITO film is formed on two glass substrates, and a Sin
．． A PVA film was applied and rubbed. Next, these two glass substrates were bonded together with a cell thickness of 2 μm. Next, the previously prepared chiral smectic C liquid crystal composite was injected. When this liquid crystal cell was placed between two orthogonal polarizers and a voltage was applied, changes in transmitted light intensity were observed. Spontaneous polarization (Ps
) was determined. The results are shown in Table 2.

Example 4 Using the compounds shown in Table 2 and the compounds shown in Table 5, ferroelectric liquid crystal magnets 30 to 35 shown in Table 6 were prepared. These Mi precepts are Sumekchisoku C phase. It was controlled so that it showed a smectic phase A phase and a nematic phase, and the helical pinch of the nematic phase was 20 μm.

(Left below) ? Table 7 shows the transition temperature and the helical pitch of the nematic phase calculated using formula (X).

A Cano type wedge-shaped cell similar to that used in Example 1 was prepared. However, the thick part of the cell should be
It was set to μm. Compositions 11m30-35 were each injected into this cell. No disclination line was observed in any of them, and it was confirmed that the helical pitch of the nematic phase of these assemblies was 20 μm or more.

Example 5 ITO film was formed on two glass substrates, and SiO
A PVA film was applied and rubbed. Next, these two glass substrates were bonded together with a cell thickness of 2 μm so that the rubbing directions were the same, and the ferroelectric liquid crystal composite produced in Example 4 was injected into each substrate. After injection, the cell was heated to a temperature at which the liquid crystal composition changed to an isotropic liquid, and then cooled to room temperature at 1° C./min to obtain a ferroelectric liquid crystal element with good orientation.

This ferroelectric liquid crystal element was placed between two orthogonal polarizers, a voltage was applied, and its characteristics were evaluated. (Left below) Table 7 shows the evaluation conditions and characteristics obtained. (G) Effects of the Invention As can be seen from the above examples, the ferroelectric liquid crystal device using the ferroelectric liquid crystal composition of the present invention has good coordination, high contrast, brightness, wide operating temperature range, and large size. A capacitive ferroelectric liquid crystal element can be obtained.

[Brief explanation of drawings]

FIG. 1 is a sectional view for explaining the structure and manufacturing method of a ferroelectric liquid crystal element using the ferroelectric liquid crystal assembly of the present invention. FIG. 2 is a diagram schematically showing a method for controlling a large capacity ferroelectric liquid crystal device using the ferroelectric liquid crystal device of the present invention. 1. 2... Insulating substrate 3.4... Conductive film 5
... Insulating film 6 ... Orientation control layer 7 ... Sealing agent 8 ... Ferroelectric liquid crystal 9 ... Polarizing plate

Claims (1)

[Claims] 1. In a ferroelectric liquid crystal element having an alignment control layer provided on at least one of a pair of substrates each provided with a voltage applying means, and a ferroelectric liquid crystal layer between the pair of substrates, At least one compound in which the dielectric liquid crystal has an optically active group represented by the following formula (I), and a compound having an optically active group in which the direction of the helical pitch induced in the nematic phase is represented by the formula (I) contains at least one compound that is the opposite of smectic C.
A ferroelectric liquid crystal element characterized by exhibiting a smectic A phase and a nematic phase with a helical pitch of 20 μm or more. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In formula (I), * indicates that the carbon atom is an asymmetric carbon atom.) 2. Optically active group represented by formula (I) The ferroelectric liquid crystal device according to claim 1, wherein the compound having the formula (II) is an optically active compound represented by the following general formula (II). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) (In the general formula (II), A^1, A^2, and A^3 represent a six-membered ring-containing group that may have a substituent, X is -O-, -
COO-, -OCO- or a single bond, Y^1 and Y
^2 is -COO-, -OCO-, -OCH_2, -CH
_2O-, -CH_2CH_2-, -CH=CH-, -
C≡C- or a single bond, R^1 and R^2 represent a linear or branched alkyl group having 1 to 15 carbon atoms, and p
, q and r are 0 or 1, and * indicates that the carbon atom is an asymmetric carbon atom. ) 3. Claim 2, wherein the optically active compound represented by the general formula (II) is a compound selected from the group consisting of optically active compounds represented by the following general formulas (II)-1 to (II)-7. The ferroelectric liquid crystal element described above. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II)-1 ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II)-2 ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II)-3 ▲Mathematical formulas, chemical formulas, There are tables, etc.▼(II)-4 ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II)-5 ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II)-6 ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II)-7 (In the above formulas (II)-1 to (II)-7, R^1, R^2 and * have the same meaning as R^1, R^2 and * in general formula (II) , e and f are 0 or 1, and X^1 represents a halogen atom or a cyano group.) 4. A compound having an optically active group represented by formula (I) has the following general formula (II') The ferroelectric liquid crystal device according to claim 1, which is an optically active compound represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II') (In the general formula (II'), A^7 indicates ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ , X^2 represents -O- or a single bond, and R^1^0 and R^1^1 are an alkyl group having 1 to 15 carbon atoms or an alkyl group having 2 carbon atoms.
-15 alkenyl groups, d and f are 0 or 1, and * indicates that the carbon atom is an asymmetric carbon atom. ) 5. A compound in which the direction of the helical pitch induced in the nematic phase is opposite to that of a compound having an optically active group represented by formula (I) has an optically active group represented by the following general formula (III). Claims 1-1 characterized in that it is a compound.
4. The ferroelectric liquid crystal device according to any one of 4. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (In the general formula (III), Z is -COO-, -OCO-, -
O-, -CO-, -OCH_2-, -OCH_2CH_
2- or a single bond, and R^3 is a phenyl group having an alkyl substituent having 1 to 15 carbon atoms, or a phenyl group having 1 to 15 carbon atoms, respectively.
Indicates a group selected from 15 linear or branched alkyl groups, alkyloxy groups, and acyloxy groups, and the alkyl in the above alkyl group, alkyloxy group, and acyloxy group has a halogen atom or a cyano group as a substituent. It may contain -O-, -COO-, a double bond or a triple bond, and it may further contain an asymmetric carbon. G is a halogen atom, -CN-, -CH_
3, -CH_2F, -CHF_2 or -CF_3, * indicates that the carbon atom is an asymmetric carbon atom. 6. The ferroelectric liquid crystal device according to claim 5, wherein the compound having an optically active group represented by the general formula (III) is an optically active compound represented by the following general formula (XII). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(XII) (In the general formula (XII), Z, R^3, G and * are the general formula (
Indicates the same meaning as Z, R^3, G and * in III), and A
^4, A^5 and A^6 represent a six-membered ring group or a five-membered ring group which may have a substituent, and X^3 is -O-, -OC
O- or a single bond, Y^3 and Y^4 are -COO-
, -OCO-, -OCH_2-, -CH_2O-, -C
H=CH-, -C≡C-, -CH_2CH_2- or a single bond, R^9 represents a linear or branched alkyl group having 1 to 15 carbon atoms, and a, b and c are 0 or 1 It is. ) 7. Claim 6, wherein the optically active compound represented by the general formula (XII) is a compound selected from the group consisting of optically active compounds represented by the following general formulas (XII)-1 to (XII)-4. The ferroelectric liquid crystal element described above. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(XII)-1 ▲There are mathematical formulas, chemical formulas, tables, etc.▼(XII)-2 ▲There are mathematical formulas, chemical formulas, tables, etc.▼(XII)-3 ▲Mathematical formulas, chemical formulas, There are tables, etc.▼(XII)-4 (In general formulas (XII)-1 to (XII)-4, R^3, R^
9, G and * are R^3, R^9, G in general formula (XII)
and * have the same meaning, e and f are 0 or 1,
h is 1 or 2. ) 8. Claims 1 to 8, wherein the ferroelectric liquid crystal contains at least one compound represented by the following general formula (IV).
7. The ferroelectric liquid crystal device according to any one of 7. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(IV) (In the general formula (IV), R^4 and R^5 each represent a linear or branched alkyl group or an alkyloxy group having 1 to 15 carbon atoms. 9. The ferroelectric liquid crystal according to any one of claims 1 to 8, characterized in that the ferroelectric liquid crystal contains at least one compound having a fluoroalkyl group represented by the following general formula (V). element. ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) (In the general formula (V), m is 1 or 2, and n is 2 to 12
is an integer. )