JPH0372466A - Liquid crystalline compound, liquid crystal composition containing the same and liquid crystal element using the same - Google Patents

Abstract

NEW MATERIAL:A liquid crystalline compound of formula I (R1 and R2 are straight chain or branched alkyl which may have a 1-16C substituent; Y1 is COO, OCO, CH2O or OCH2; Z1 is single bond, O, COO, OXO or OCOO; X is halogen, CN or CH3). EXAMPLE:Trans-4-n-propylcyclohexanecarboxylic acid-[2-fluoro-4-(5-decyl-2- pyrimidinyl)phenyl] ester. USE:A component for a liquid crystal composition having a high response rate and reduced in the temperature dependency of the response rate, especially for a ferromagnetic chiral smectic liquid crystal. PREPARATION:For example, a compound of formula II or III is reacted with a compound of formula IV to provide the compound for formula I wherein Y1 is COO.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel liquid crystal compound, a liquid crystal composition containing the same, and a display element using the same. The present invention relates to a novel liquid crystal composition, and a liquid crystal element using the same for use in liquid crystal display elements, liquid crystal-optical shutters, and the like.

[Conventional technology]

Conventionally, liquid crystals have been applied as electro-optical elements in various fields. Most of the liquid crystal elements currently in practical use are based on, for example, "Applied Physics Letters" by M. Chadt and W. Helfrich.
hysics Letters') Vo, 18.
No. 4 (1971°2.15) P. 127-12
8'Voltage Dependent Optic
al Activity of a Twisted
This uses a TN (Twisted Nematic) type liquid crystal shown in "Nematic Liquid Crystal".

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

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

If the difference between the voltage applied to the selected point and the voltage applied to the half-selected point is sufficiently large, and the voltage threshold required to align the liquid crystal molecules perpendicular to the electric field is set to an intermediate voltage value,
Although the display element operates normally, the number of scanning lines (N
), the time during which an effective electric field is applied to one selected point (duty ratio) decreases by 17N while scanning the entire screen (1 frame).

For this reason, when repeated scanning is performed, the effective voltage difference between selected points and non-selected points becomes smaller as the number of scanning lines increases, resulting in a decrease in image contrast and crosstalk. This is a drawback that is difficult to avoid.

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

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

Clark (C1
ark) and Lagerwall (Japanese Unexamined Patent Publication No. 107216/1983,
(U.S. Pat. No. 4,367.924, etc.).

Chiral smectic C is generally used as a bistable liquid crystal.
A ferroelectric liquid crystal having a phase (SmC* phase) or an H phase (S m H phase) is used.

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

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

In this way, ferroelectric liquid crystals potentially have extremely excellent properties, and by utilizing these properties,
Significant substantial improvements are obtained over many of the problems of conventional TN type devices mentioned above. In particular, it is expected to be applied to high-speed optical shutters and high-density, large-screen displays. For this reason, extensive research has been conducted on liquid crystal materials with ferroelectric properties, but the ferroelectric liquid crystal materials developed to date have sufficient characteristics for use in liquid crystal devices, including low-temperature operation characteristics and high-speed response. It is hard to say that it is equipped with the following.

The following relationship exists between the response time τ, the magnitude of spontaneous polarization Ps, and the viscosity η as shown in the following equation [11 (where E is the applied electric field). Therefore, to increase the response speed, (
There is a method of (a) increasing the magnitude of spontaneous polarization Ps, (b) decreasing the viscosity η, and (ii) increasing the applied electric field E. The applied electric field has an upper limit because it is driven by an IC or the like, and it is desirable that it be as low as possible.

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

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

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

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

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

[Problem to be solved by the invention]

An object of the present invention is to provide a liquid crystal composition, particularly a ferroelectric chiral smectic liquid crystal composition, which has a high response speed and reduced temperature dependence of the response speed, in order to make a ferroelectric liquid crystal element practical. , and to provide a liquid crystal element using the liquid crystal composition.

[Means to solve the problem]

The present invention is based on the following general formula (I) (wherein R1e R2 is a linear or branched alkyl group which may have a substituent having 1 to 16 carbon atoms.Y
l is -COO--0CO-, -CH2O--OCH2-
and zl is a single bond, -o--co.

-oco-, -ocoo-. Moreover, X is a halogen, cyano, or methyl group. ), a liquid crystal composition containing at least one liquid crystal compound represented by the general formula (I), and at least one liquid crystal compound represented by the general formula (I); Formula (If) (However, Rs and R4 represent a linear or branched alkyl group having 1 to 1.8 carbon atoms.These are substituents such as
It may have an alkoxy group having 1 to 12 carbon atoms. However, it is non-optically active.

So, z6 is -0CH2+, -COOCH,+, -oco
--〇+CH2+T-0-CH,-. -(9-
is 1. ), and the liquid crystal composition contains at least one liquid crystal compound represented by the general formula (I
I) (However, R, has 1 to 1 carbon atoms, which may have a substituent.
18 linear or branched alkyl groups. Y2 is a single bond, -coo+, -0CO-, -cos--8CO-
, -CH20-, -OCH,-, -CH=CH-COO
-, z4 is a single bond, -o--coo-, -oco
-Also, l is an integer of 1-12, and k is an integer of 1-4. The present invention provides a liquid crystal composition further containing at least one liquid crystal compound represented by the following formula, and a liquid crystal element in which the liquid crystal composition is disposed between a pair of electrode substrates.

Among the liquid crystalline compounds represented by the general formula (1), preferred compounds include compounds represented by the following formulas (I-a) to (I-b).

(i) n-alkyl group H3 having 1 to 16 carbon atoms (ii) -G CH2)mcH-CnH2n++
(However, m is an integer of 1 to 7, and n is an integer of 2 to 9, but within the range of 3≦m and n≦14.Also, it may be an optically active group.) R1+ R2+ XT
Z H is as described above) Among formulas (I-a) to (1-b), a particularly preferred compound is a compound represented by the following formula (I-c).

Furthermore, among the liquid crystalline compounds represented by general formula (I), R1
is preferably (i), and R2 is preferably 0→~(
iv) selected from.

(However, r is an integer from 0 to 7, and S is O or l
It is. Also, t is an integer from 1 to 14, but 1≦r+s
+t≦14. It may also be optically active. ) (iv) CH2CHCx H2X+1 (However, X is an integer of !-14.) In addition, in the liquid crystal compound represented by formula (I), preferable examples of A fluorine atom is particularly preferred.

Further, in the liquid crystal compound represented by the general formula (I), a preferable example of zl is a single bond.

is a single bond, -0-.

Furthermore, among the compounds represented by the aforementioned general formula (II),
Preferred examples of compounds include the following formulas (II-a) to
Examples include compounds represented by (ne).

Ra z24 lying z3R4 R3-Z 2-@-@-z 3-R4 R3-22<71-@-o-23-R4R3-22g>
o-z 3-R4 R322 and Z3R4 (R3+ R4+ Z21 Z s is as mentioned above)
('n -a) (n -b) (II -c) (n -d) (It -e) Furthermore, as a preferable example of Z2+23 in the above formulas (II a) to (II-e), ( II-i)~
(II-viii) can be mentioned.

(II-i) Z2 is a single bond, z3 is a single bond (II-ii) Z2 is a single bond, z3 is -〇-(II-iii) Z 2 is a single bond, Z3
is -0C-j (II-iv) Z2 is a single bond, Z3 is -
CO-1 (Il -v) Z 2 is -0-1Z, is
Single bond (II-vi) Z2 is -0-1z3 is 10-(I
I-vii) Z2 is 10-1Z3 is -OC-1 In addition, R in the above formulas (II-a) to (II-e) is preferably a linear chain having 4 to 14 carbon atoms or It is a branched alkyl group, and these may have an alkyl group having 1 to 12 carbon atoms as a substituent, and R8*
A more preferable example of R4 is the following (II-ix)
~(II-xi) can be mentioned.

(II-ix) RS # R4 is independently an n-alkyl group having 4 to 14 carbon atoms (II-x) R8 is an n-alkyl group having 4 to 14 carbon atoms.

(U is 0 to 7, R6 is a linear or branched alkyl group) (II-xi) R@ is an n-alkyl group.

(y is 0 to 7, U is 0 or 1. R is a linear or branched alkyl group) Also, among the compounds represented by the above general formula (IN),
Preferred examples of compounds include the following formulas (II-a) to (
Examples include compounds represented by III-f).

(R6* z4+ Z Ss j! is as described above)
Further, among the compounds represented by the above formulas (II-a) to (If), particularly preferred compound examples include the formula (DI-
a), formula (m-b), and formula (Ill-c).

Furthermore, z4. in the above formulas (nI-a) to (m-f). As a preferable example of zls, the following (m - i)
~(In-v) can be mentioned.

(II-i) Z4 is a single bond, 2. is -0-CH2
-(n[-1i) Z4 is a single bond, 2. Ga-Coo
-CH2-(I[-1ii) Z4 is a single bond, z8 is 1000-(III-iv) Z4 is 10-28 10-
CM 2-(II[-v) Z4 is 10 -2, is -C
OOCR2-[Detailed Description of the Invention] A typical synthetic route for the liquid crystalline compound represented by the general formula (R) is shown below.

i) If Y is -Coo-, -CH2O- (7) then R1@scream R, □RanH 1f) Y is 10CO- 0CR - in case of -5 -6 -9 The above general formula () of the liquid crystalline compound represented by Specific compound examples are shown below.

-1 -2 -3 -4 -10 -11 -12 -13 -14 1-15 1-16 -17 -18 -19 -25 -26 -27 -28 -29 -20 -21 -22 -23 -24 -30 -31 -32 -33 -34 r l-35 1-36 -37 -38 -39 -45 -46 -47 -48 -49 r 0 -41 -42 3 4 -50 -51 -52 -53 - 54 l-55 1-56 -57 -58 -59 -65 -66- 67-6 -69 -60 -61 -62 -63 -64 -70 -71 -72 -73 -74 r r l-75 1- 76 7- 7 -79 -85 -86 -87 -88 9 -80 -81 -82 -83 -84 -90 -91 -92 -93 -94 l-95 1-96 -97 -98 r -99 -105 -106 -107 -108 -109 -100 -101 -102 -103 -104 -110 -111 -112 -113 -114 1-115 The compound represented by the general formula (II) is, for example,
5892 (1973), Patent Publication Sho 62-5434
(1987).

Further, for example, the compound represented by -116 can be synthesized by the following synthetic route.

(R3゜R4゜q in the formula is as described above) A typical synthesis example of the compound represented by the general formula (n) is shown below.

Synthesis Example 1, (Synthesis of compound No. 2-54) Pyridine 5mj! 5-methoxyhexanol dissolved in
．． 06 g (8.0 mmol) of p-)luenesulfonic acid chloride 1.83 g (
9.6 mmol) was added dropwise to the mixture at 5° C. or lower in ice water. After stirring at room temperature for 6 hours, the reaction mixture was poured with 100 mf of cold water.
injected into. After making the mixture acidic with 6N hydrochloric acid, the mixture was extracted with isopropyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off to obtain 5-methoxyhexyl-p-)luenesulfonate.

Dimethylformamide 10mj! 5-decyl-2-(
p-hydroxyphenyl)pyrimidine 2.0g (6,4
1 m m o 1 ) and 0.61 g of potassium hydroxide were added thereto, and the mixture was stirred at 100°C for 40 minutes. Add to this the 5 you got earlier.
-Methoxyhexyl-p-toluenesulfonate was added, and the mixture was heated and stirred at 100°C for 4 hours. After the reaction was completed, the reaction mixture was poured into 100 ml of cold water and extracted with benzene. After washing with water, it was dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain a pale yellow oil.

Karamkron The general formula (n) of the liquid crystalline compound represented by Dographie (Silica gel-ethyl acetate/benza Specific compound examples are shown below.

= 179) After purification by recrystallized from hexane 5-decyl-2- (4- (5' Ichime Toxyhexy (2-1) (Ruoxy) phenyl) 1.35 g of pyridine was obtained.

Phase transition temperature (2-2) (2-3) (2-4) (2-5) (2-10) (2-6) (2-11) (2-7) (2-12) (2 -8) (2-13) (2-9) (2-14) (2-15) (2-16) (2 17) (2-18) (2-19) (2 25) (2 26) (2-27) (2-28) (2-29) (2-20) (2-21) (2-22) (2-23) (2-24) (2-30) (2-31) (2-32) (2-33) (2-34) (2-35) (2-36) (2-37) (2-38) (2-39) (2-45) (2-46) (2-47) (2-48) (2-49) (2-40) (2-41) (2-42) (2-43) (2-44) (2-50) (2-51) (2-56) (2-57) (2-58) (2-59) (2-65) (2 65) (2 66) (2-67) (2-68) Soot υ (2-60) (2-61) (2-62) (2-63) (2-64) (2-69) (2-70) (2-71) (2-72) (2-73) Suriri (2- 74) (2-75) (2-76) (2-77) (2-78) (2-84) (2-85) (2-86) (2-87) (2-88) υ Suυ υ υ υ υ (2-79) (2-80) (2-81) (2-82) (2-83) (2-89) (2-90) (2-91) υ υ υ υ (2-95) (2-96) (2-97) (2-98) (2-104) (2 105) (2-106) (2-107) (2-108) (2-99) ( 2-100) (2-101) (2-102) (2-103) (2-109) (2-110) (2-111) (2-112) (2-113) (2-114) ( 2-115) (2-116) (2-117) (2-118) υ The compound represented by the general formula (1) is
It can be obtained by the methods described in JP-A-22042, JP-A-63-122651, and the like.

Typical synthesis examples are shown below.

Synthesis Example 2 (Synthesis of Compound No. 3-28) p-2-fluorooctyloxyphenol 1. OOg (4, 16m
M) was dissolved in 10 ml of pyridine, 11 ml of toluene, and 1,30 g of trans-4-n-pentylcyclohexanecarboxylic acid chloride (6,00 m M
) dissolved in 5 ml of toluene was heated at 5°C or less for 20
It was added dropwise over a period of ~40 minutes. After the dropwise addition, the mixture was stirred at room temperature overnight to obtain a white precipitate.

After the reaction was completed, the reaction product was extracted with benzene, and the benzene layer was further washed with distilled water, and then the benzene layer was dried over magnesium sulfate, and the benzene was distilled off. It was further purified using silica gel column chromatography and recrystallized from ethanol/methanol.
n-pentylcyclohexanecarboxylic acid p-2-fluorooctyloxyphenyl ester 1, 20 g
(2.85mM) was obtained. (Yield 68.6%) NMR data (ppm) 0.83-2.83ppm (34H, m) 4.00-
4.50ppm (2H,q)7,llppm
(4H, 5) IR data (cm-') 3456, 2928° 1470, 1248° 854° Phase transition temperature (℃) 1742, 1508° 2852° 1166, 1132° 1200° (here, Sll* s4.S5 *s, is SmC
*Indicates a phase with a higher degree of order. ) Synthesis Example 3 (Synthesis of Compound No. 3-85) In a container that was sufficiently purged with nitrogen, 0.40 g (3.0 mmol) of C-')-2-fluoroheptanol and 1.0 g (3.0 mmol) of dry pyridine were added. o
Og (13 mmol) was added and stirred for 30 minutes under water cooling. Add 0.69 of P-)luenesulfonic acid chloride to the solution.
g (3.6 mmol) was added thereto, and stirring was continued for 5 hours. After the reaction is completed, 1NHcj 10mj! was added and extracted twice with 10mf of methylene chloride, and the extract was poured into 10mj of distilled water! Washed once with After appropriately adding anhydrous sodium sulfate to the obtained methylene chloride solution and drying, the solvent was distilled off to give 0.59 g (2.0 m
m o 1 ) was obtained.

Yield is 66%. The specific rotation of the product and! The R data is as follows.

Specific optical rotation [(l] F + 2.59° (c=IS
CHC13).

Specific optical rotation [alW+s, sso (c=1. CHCj
! s).

IR(am-'): 2900, 2850, 1600, 1450.13
50, 1170, 1090, 980.810,
660, 550° 0.43 g (1,5
m mol ) and 5-octyl-2-(4-hydroxyphenyl)pyrimidine OJ8g (1,0mmol
) was added with 0.2 mj+ of 1-butanol and stirred well.

Add 1.0 mj of l-butanol to the solution in advance. An alkaline solution prepared by dissolving 0.048 g (1.2 mmo+) of sodium hydroxide in the solution was immediately poured into the solution, and the mixture was heated under reflux for 5 hours. Distilled water 10r+1 after completion of reaction
was added and extracted once with 10 ml and 5 ml of benzene, respectively, and the extract was dried by appropriately adding anhydrous sodium sulfate. After drying, the solvent was distilled off and the desired product (+) was collected using a silica gel column (chloroform).
-5-octyl-2-[4-(2-fluorohebutyloxy)phenylcopyrimidine 0.17g
mof) was obtained.

The yield was 43%, and the specific rotation and IR were as follows:
The data was obtained.

Specific optical rotation [α]! 7' + 0.44' (c =
1.CHCj! 3).

Specific optical rotation [α] +4.19' (c = 1, C
HCl! 3).

IR(am-'): 2900.2850.1600.1580.1420.
1250.1160.800.720.650.550
0 Specific compound examples of the liquid crystal compound represented by the general formula (III) are shown below.

(3-1) (3-2) (3-4) (3-5) (3-10) (3-6) (3-1'l) (3-7) (3-12) (3- 8) (3-13) (3-9) (3-14) (3-15) (3-16) (3-17) (3-18) (3-19) (3-25) (3- 26) (3-27) (3-28) (3-29) (3-20) (3-21) (3-22) (3-23) (3-24) (3-30) (3- 31) (3-32) (3-32) (3-33) (3-34) (3-35) (3-36) (3-37) (3-38) (3-44) (3- 45) (3-46) (3-47) (3-48) (3-39) (3-40) (3-41) (3-42) (3-43) (3 49) (3-50 ) (3-52) (3-53) (3-54) (3-55) (3-56) (3-57) (3-58) (3-59) (3-65) (3-66 ) (3-67) (3-68) (3-69) (3-60) (3-61) (3-62) (3-63) (3-64) (3-70) (3-71 ) (3-72) (3-73) (3-74) (3-75) (3-76) (3-77) (3-78) (3-79) (3-85) (3-86 ) (3-87) (3-88) (3-89) (3-80) (3-81) (3-82) (3-83) (3-84) (3-90) (3-91 ) (3-92) (3-93) (3-94) (3-95) p (3-96) (3-97) (3-98) (3-99) (3-105) (3- 106) (3-107) (3-108) (3-109) (3-100) (3-101) (3-102) (3-103) (3-104) (3-110) (3- 111) (3-112) (3-113) The liquid crystal composition of the present invention comprises at least one liquid crystal compound represented by the general formula (I) and one or more other liquid crystal compounds in an appropriate ratio. It can be obtained by mixing.

Further, the liquid crystal composition according to the present invention is preferably a ferroelectric liquid crystal composition, particularly a ferroelectric chiral smectic liquid crystal composition.

The above-mentioned (I), (IF), (m
) Specific examples of other liquid crystal compounds that can be mixed are listed below.

Compound no.

(5) (6) CH.

(12) (lO) CH3 (11) 〒H3 c 16 H, O-@-C3-@-OCH2CHC3H
71* CH3 H3 (22) (34) (27) CH3 CM 3 (28) CH3 (29) Cs Hts + oc(H CH, CHC, H.

11* '(36) CH.

vinegar (37) CH3 ■ (38) CH3 CH.

0 (46) (48) (61) CH3 CH.

(67) CH3 cloudy (68) CH3 (69) CH3 (71) CH3 (83) CH3 υ (74) CH3 (76) CH.

(77) CHa C1゜H21←O→CH2)2 CO-@-OCH2C
HOC2H, s11* (84) CH3 Su (87) CH3 Back (102) 0 Su CI! (108) (109) (110) (112) I II l l 0 (116) (117) CF.

” (126) (127) (131) (120) CF a c , H, O-@-@-COCHC6Htjl,! i
* (132) (133) (134) (135) (136) (137) (138) (139) (140) (141) (142) (143) (150) (151) (152) (153) ( 154) (155) υ (144) (145) (146) (147) (148) (149) (156) (157) (158) (159) (160) (161) C1□H260 (Decision CH2o-@ -oc, H,3(
162) 0 (163) (164) (165) (166) (167) The liquid crystal compound represented by the general formula (I) of the present invention and one or more of the other liquid crystal compounds mentioned above, or liquid crystal composition (Hereinafter abbreviated as liquid crystal material) The compounding ratio of the liquid crystalline compound represented by the general formula (R) of the present invention is 1 to 300 parts by weight, preferably 2 to 200 parts by weight, per 100 parts by weight of the liquid crystal material. This is desirable.

Furthermore, even when two or more types of liquid crystalline compounds represented by the general formula (1) of the present invention are used, the blending ratio with the liquid crystal material is as follows: It is desirable that the amount of the mixture of two or more types of compounds is 1 to 500 parts by weight, preferably 2 to 200 parts by weight.

Furthermore, the compounding ratio of each of the liquid crystal compounds represented by the general formula (I) and the general formula (n) or the general formula (I) and the general formula (III) of the present invention and the liquid crystal material is 100 parts by weight of the liquid crystal material. 1 to 300 parts by weight, preferably 2 to 200 parts by weight of each of the liquid crystalline compounds represented by the general formula (I) and the general formula (If), or the general formula (I) and the general formula (m) of the present invention. It is desirable to do so.

Furthermore, general formula (I) and general formula (II) of the present invention,
Alternatively, when using one or more of the liquid crystal compounds represented by the general formula (I) and the general formula (■), the compounding ratio with the liquid crystal material is based on the general formula of the present invention per 100 parts by weight of the liquid crystal material. (I) and general formula (n), or general formula (
It is desirable that the mixture of two or more of one or both of 1) and the liquid crystal compound represented by general formula (m) be 1 to 500 parts by weight, preferably 2 to 200 parts by weight.

Furthermore, the compounding ratio of each of the liquid crystalline compounds represented by the general formula (I), general formula (n), and general formula (III) of the present invention and the liquid crystal material is as follows: Formula (I), general formula (II), and general formula (m)
It is desirable that the amount of each of the liquid crystalline compounds represented by the following is 1 to 300 parts by weight, more preferably 2 to 200 parts by weight.

Furthermore, even when using two or more of the liquid crystalline compounds represented by the general formula (i), general formula (n), and general formula (m) of the present invention, the blending ratio with the liquid crystal material is as follows: Per 100 parts by weight of the liquid crystal material, the general formula (I
), general formula (II), and general formula (I
It is preferable to use parts by weight.

Furthermore, the ferroelectric liquid crystal layer in the ferroelectric liquid crystal element according to the present invention can be obtained by heating the ferroelectric liquid crystal composition prepared as described above to an isotropic liquid temperature in vacuum, and placing it in the element cell. It is preferable to encapsulate it, gradually cool it to form a liquid crystal layer, and return it to normal pressure.

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

In FIG. 1, the symbol l is a ferroelectric liquid crystal layer, 2 is a glass substrate, 3 is a transparent electrode, 4 is an insulating alignment control layer, 5 is a spacer, 6 is a lead wire, 7 is a power source, 8 is a polarizing plate, 9 indicates a light source.

The two glass substrates 2 are each made of In2O3゜SnO.
□Or ITO (indium tin oxide;
A transparent electrode 3 made of a thin film such as Indium-Tin Oxide (Indium-Tin Oxide) is coated thereon. On top of this, a thin film of a polymer such as polyimide is rubbed with gauze or acetate flocked cloth to form an insulating alignment control layer that aligns the liquid crystals in the rubbing direction. Insulating materials such as silicon nitride, hydrogen-containing silicon carbide, silicon oxide, boron nitride, hydrogen-containing boron nitride, cerium oxide, aluminum oxide, zirconium oxide, titanium oxide, and fluoride Form an insulating layer of inorganic material such as magnesium, and then apply polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyparaxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin. 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 layer is inorganic, it can be formed by a vapor deposition method, or if it is organic, it can be formed by a solution containing an organic insulating material or its precursor solution (0.1 to 20%
% by weight, preferably 0.2 to 10% by weight) by a spinner coating method, dip coating method, screen printing method, spray coating method, roll coating method, etc., and under predetermined curing conditions (for example, under heating). ) can be cured and formed.

The thickness of the insulating orientation control layer is usually 50 to 1 μm, preferably 100 to 3000 μm, and more preferably 100 to 1000 μm.

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

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

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

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

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

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

FIG. 2 schematically depicts an example of a cell for explaining the operation of a ferroelectric liquid crystal element. 21a and 21b are In2O3, 5n02 or ITO (Indiu
It is a substrate (glass plate) coated with a transparent electrode made of a thin film such as (m-Tin Oxide), and a liquid crystal of SmC phase or SmH main phase with the liquid crystal molecular layer 22 oriented perpendicular to the glass surface is sealed between the substrates. has been done. A thick line 23 represents a liquid crystal molecule, and this liquid crystal molecule 23
is the dipole moment (P soil) in the direction perpendicular to the molecule
It has 24. When a voltage equal to or higher than a certain threshold is applied between the electrodes on the substrates 21a and 21b, the helical structure of the liquid crystal molecules 23 is unraveled, and the liquid crystal molecules 23 are aligned in the direction such that the dipole moment (on P) 24 is all directed in the direction of the electric field. can be changed. The liquid crystal molecules 23 have an elongated shape and exhibit refractive index anisotropy in the long axis direction and short axis direction. Therefore, for example, if crossed Nicol polarizers are placed above and below the glass surface, the polarity of the applied voltage will change depending on the voltage applied polarity. It is easily understood that this results in a liquid crystal optical modulation element whose optical properties change.

The liquid crystal cell preferably used in the optical modulation element of the present invention can have a sufficiently thin thickness (for example, 1Oμ or less). As the liquid crystal layer becomes thinner in this way, the helical structure of the liquid crystal molecules unwinds even when no electric field is applied, as shown in Figure 3, and the dipole moment Pa or pb is directed upward (34a) or downward (34b).
). In such a cell, an electric field Ea or E of different polarity above a certain threshold value is applied as shown in FIG.
When b is applied by the voltage applying means 31a and 31b, the dipole moment changes its direction upward 34a or downward 34b in accordance with the electric field vector of the electric field Ea or Eb, and accordingly, the liquid crystal molecules are moved to the first stable state. It is oriented to either the state 33a or the second stable state 33b.

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

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

The present invention will be explained in more detail with reference to Examples below.

Example 1 The above compound, trans-4-n-propylcyclohexanecarboxylic acid-[2-fluoro-4-(5-decyl-2
-pyrimidinyl)phenyl]ester (Example Compound 1-
2) Synthesis of 2-fluoro-4-(5-decyl-2-pyrimidinyl)
Phenol 0.50g (1.52mM)
It was dissolved at 0 mA and stirred under a water bath. To this, 0-34 g (1,82 mmol) of trans-4-n-propylcyclohexanecarboxylic acid chloride was added dropwise, and the mixture was stirred in a water bath for 5 hours.

The reaction mixture was drained, acidified with concentrated hydrochloric acid, extracted with methylene chloride, further washed with water, dried over sodium sulfate, and then distilled off.

This was purified by silica gel column chromatography using a mixed solvent of toluene/ethyl acetate, and recrystallized from a mixed solvent of ethanol/ethyl acetate.
, 92mM) was obtained. (Yield 60.3%) Phase transition temperature (°C) 42.4 Example 2 υ The above compound, trans-4-n-pentylcyclohexanecarboxylic acid-[2-fluoro-4-(5-decyl-2
-pyrimidinyl)phenyl]ester (Example Compound 1-
8) Synthesis of 2-fluoro-4-(5-decyl-2-pyrimidinyl)
Phenol 0.50g (1.52mM)
0.39 g of trans-4-n-pentylcyclohexanecarboxylic acid chloride (1,80 mM
) was added dropwise under a water bath. After the dropwise addition, the water bath was removed, and the mixture was stirred at room temperature for 30 minutes and then in a 40-50°C water bath for 2 hours.

After the reaction, 100mj of ice water! The precipitated crystals were filtered out. The crystals were dissolved in ethyl acetate, washed with 2N hydrochloric acid and water, dried over sodium sulfate, and evaporated.

This was purified by silica gel column chromatography in toluene solvent, recrystallized from the freezer in ethanol solvent,
0.45g (0.88mM) of the target product was obtained.

(Yield 58.2%) Phase transition temperature (°C) 42.8 87.0 155.
1 Example 3 The following exemplified compounds were mixed in the following parts by weight to prepare liquid crystal composition A.
It was created.

Exemplary Compound No. Structural Formula Parts by Weight Exemplary Compound No.

Further, to this liquid crystal composition A, the following exemplified compounds were mixed in the weight parts shown below to prepare a liquid crystal composition B.

Exemplary Compound No. Structural Formula Weight Parts 5 Next, two 0.7 mm thick glass plates were prepared, an ITO film was formed on each glass plate, a voltage application electrode was created, and SiO2 was deposited on top of this to form an insulating layer. Silane coupling agent [Shin-Etsu Chemical ■] on the glass plate
KBM-602] A 0.2% isopropyl alcohol solution was applied for 15 seconds using a spinner with a rotational speed of 200 Orr, p, m for surface treatment.

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

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

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. Glue the glass plates together using adhesive sealant [Rixon Bond (Chisso ■)] so that they are parallel to each other for 60 minutes.
A cell was prepared by heating and drying at 100°C. The cell thickness of this cell was measured using a Bereck phase plate and was approximately 2 μm.
Met.

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

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

The results are shown below.

15℃ Muscle ℃35℃ Response speed 134 μsec 89 μs
ec 74 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

Comparative Example 1 A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that the liquid crystal composition A mixed in Example 3 was injected into the cell, and the optical response speed was measured.

The results are shown below.

Example 4 In place of Exemplified Compound 1-2 used in Example 3, the following exemplary compounds were mixed in the weight parts shown below to prepare a liquid crystal composition C.

Exemplary compound No. Structural formula Weight part 15'IC raw temperature 35°C Response speed 155 p sec 100
μsec 80 psec As is clear from Example 3 and Comparative Example 1, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved response speed. Temperature dependence is also reduced.

A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3.

The measurement results are shown below.

15'IC2fc35℃ Response speed 132μsec 88μsec
Example 5 In place of Exemplified Compound 1-8.1-37 used in Example 4, the following exemplary compounds were mixed in the weight parts indicated below to prepare a liquid crystal composition.

Exemplary Compound No. Structural Formula Weight Parts Also, clear switching action was observed during driving,
Bistability was also good when voltage application was stopped.

As is clear from Example 4 and Comparative Example 1, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3.

The measurement results are shown below.

15℃ 256C35℃ Response speed 128μsec 86μs
ec 71 μsec Example 6 Exemplary Compounds 1-17 used in Example 5. In place of 1-61°1-45, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition E.

Exemplary Compound No. Structural Formula Weight Parts Also, clear switching action was observed during driving,
Bistability was also good when voltage application was stopped.

As is clear from Example 5 and Comparative Example 1, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3.

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 119 μsec 79 μ
sec 65 p sec Example 7 Exemplary compound 1-11 used in Example 6. In place of 1-49° and 1-55, the following exemplified compounds were mixed in the weight parts shown below to prepare a liquid crystal composition F.

Exemplary Compound No. Structural Formula Weight Parts Also, clear switching action was observed during driving,
Bistability was also good when voltage application was stopped.

As is clear from Example 6 and Comparative Example 1, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

0 A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3.

The measurement results are shown below.

15℃ part℃35℃ Response speed 131 B sec 90
p sec 71 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example G47 and Comparative Example 1, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of response speed. has been done.

Example 8 Exemplary compound 1-20.1-72゜1 used in Example 7
Liquid crystal composition G was prepared by mixing the following exemplified compounds in the weight parts shown below in place of -80.

Exemplified Compound No. Structural Formula Parts by Weight 1 A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was determined in the same manner as in Example 3. It was measured.

The measurement results are shown below.

15℃ 25'0 35℃ response speed
131 p sec 894 sec
70 p sec Example 9 The following exemplified compounds were mixed in the following parts by weight to prepare liquid crystal composition H.
It was created.

Exemplary Compound No. Structural Formula Weight Parts Also, clear switching action was observed during driving,
Bistability was also good when voltage application was stopped.

As is clear from Example 8 and Comparative Example 1, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

Exemplary compound no.

Structural Formula Further, the following exemplified compounds were mixed with this liquid crystal composition H in the weight parts shown below to prepare a liquid crystal composition (2).

Exemplary Compound No. Structural Formula Weight Parts 59 0 -13 6.75 Su-7 18,75 0 A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that this liquid crystal composition was used. The optical response speed was measured in the same manner as in Example 3, and the switching state was observed.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 390 B sec 251
μsec 192 μsec Comparative Example 2 A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that the liquid crystal composition H mixed in Example 9 was injected into the cell, and the optical response speed was measured.

The results are shown below.

15℃ 25℃ 35℃Response speed 450 psec 270 μs
ec 1951t sec Example 9 and Comparative Example 2
As is clearer, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of the response speed.

Example 1O Exemplary compound 1-2.1-16゜1- used in Example 9
In place of No. 34, the following exemplified compounds were mixed in the weight parts shown below to prepare Liquid Crystal Composition J.

A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that the liquid crystal composition of Exemplified Compound No. and Structural Formula (parts by weight) was used, and the optical response speed was determined in the same manner as in Example 3. Measurements were taken to observe the switching state, etc.

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

The measurement results are shown below.

1 dead part'0 35℃ Response speed 395 μsec 242
p sea 183 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 1O and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence and migration of response speed. has also been reduced.

Round Example 11 Exemplary compound 1-6 used in Example 1O. -1-33.
.

Liquid crystal composition K was prepared by mixing the following exemplified compounds in the weight parts shown below in place of 1-64.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 388 μsec 241
μsec 185 psec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 11 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

Example 12 In place of Exemplified Compounds 1-48.1-53°1-71 used in Example 11, the following exemplary compounds were mixed in the weight parts indicated below to prepare a liquid crystal composition.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 366 μsec 244
μsec 187 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 12 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

9 Example 13 Exemplary compounds 1-4 used in Example 12. 1-8゜1
-49.1-63.1-86, the following exemplary compounds were mixed in the weight parts shown below to form a liquid crystal composition M.
It was created.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 374 μsec 247
μsec 190 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 13 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

9 Example 14 Exemplary compound 1-1.1-41゜1 used in Example 13
In place of -57.1-66, the following exemplary compounds were mixed in the weight parts shown below to prepare a liquid crystal composition N.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

15℃ 2 generations 35℃ Response speed 3846 sec 244
μsec 186 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 14 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

Nail Example 15 Exemplified compound 1-2.1-7゜1- used in Example 14
In place of 38.1-54.1-87, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 0.

Exemplary Compound No. Structural Formula Parts by weight 2 A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was determined in the same manner as in Example 3. The switching state was observed.

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

The measurement results are shown below.

l ■ Part ℃ 35℃ Response speed 315 p sec 203
B sec 152 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 15 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

Example 16 Instead of Exemplified Compound 1-49.1-71 used in Example 15, the following exemplary compounds were mixed in the weight parts shown below to prepare a liquid crystal composition P.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 374 μsec 246
μsec 189 μsec Also, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 16 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

Example 17 Exemplary compound 1-2.1-21゜1 used in Example 16
In place of -90.1-94, the following exemplified compounds were mixed in the weight parts shown below to prepare a liquid crystal composition Q.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

1511C test 35℃ Response speed 366 p sec 243
p sec 184 μsec Further, clear switching behavior was observed during driving, and good bistability was observed when voltage application was stopped.

As is clear from Example 17 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. It has been reduced.

0 Example 18 In place of the 1.5% dimethylacetamide solution of the polyimide resin precursor used in Example 3, a 2% aqueous solution of polyvinyl alcohol resin [PVA-117 manufactured by Kuraray ■] was used. A dielectric liquid crystal element was prepared, and the optical response speed was measured in the same manner as in Example 3.

The results are shown below.

15℃ 25℃ 35℃ 128 μsec 85 μsec 70
p sec Example 19 A ferroelectric liquid crystal element was created in the same manner as in Example 3, except that the alignment control layer was created only with polyimide resin without using the Sing used in Example 3. The optical response speed was measured in the same manner as in Example 3.

The results are shown below.

15℃ 35℃ 125 B sec 83 μsec 68
μsec Example 18. As is clear from Example 19, even when the device configuration is changed, the device containing the ferroelectric liquid crystal composition according to the present invention has greatly improved low-temperature operating characteristics and a response speed of Dependency has been reduced.

Examples 20 to 22 Trans-4-n-propylcyclohexanecarboxylic acid-[2-
Fluoro-4-(5-octyl-2-pyrimidinyl)phenyl]ester (Example 20. Exemplary compound 1-104
), trans-4-n-propylcyclohexanecarboxylic acid-[2-fluoro-4-(5-undecyl-2-pyrimidinyl)phenyl]ester (Example 21. Exemplary compound 1-3), trans-4-n -Pentylcyclohexanecarboxylic acid-[2-fluoro-4-(5-undecyl-2-pyrimidinyl)phenyl]ester (Example 2)
2. Exemplified Compound 1-107) was obtained.

The phase transition temperature of each compound is shown below.

(Example 21. Exemplified Compound 1-3) 3 (Example 22, Exemplified Compound 1-107) (Example 20,
Exemplary compound t-104) S4◆--S.

22 Example 23 The following exemplified compounds were mixed in the following parts by weight to prepare liquid crystal composition R.
It was created.

Exemplified Compound No. Structural Formula Parts by weight Furthermore, the following exemplary compounds were mixed with the liquid crystal composition R in the weight parts shown below to prepare liquid crystal composition 23-
I created R.

Exemplary Compound No. Structural Formula Parts by Weight Exemplary Compound No.

Structural Formula A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used.The optical response speed was measured in the same manner as in Example 3, and the switching state was observed. did.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 115μsec 80μsec
68 μsec Comparative Example 3 Liquid crystal composition 23-R was prepared by using the same parts by weight without using only the exemplified compound 1-2.1-109 used when mixing liquid crystal composition 23-R in Example 23. A ferroelectric liquid crystal device was prepared in the same manner as in Example 3 except that Rh was mixed and injected into the cell, and the optical response speed was measured.

The results are shown below.

15°C part 35°C Response speed 132 μsec 87 p
sec 71 p sec As is clear from Example 23 and Comparative Example 3, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures, and also has a faster response speed. Temperature dependence is also reduced.

Example 24 Exemplary compound 1-2.1-109゜2-16.2-24.2-54.2-67 used in Example 23 and liquid crystal composition R were mixed in the parts by weight shown below, Liquid crystal composition 24
-R was created.

Exemplary compound No., parts by weight -2 -109 -16 -24 -54 -67 Liquid crystal composition R 3,5 1,5 6,5 6,5 3,5 3,5 75,0 Using this liquid crystal composition Except for the above, a ferroelectric liquid crystal element was prepared in the same manner as in Example 3, the optical response speed was measured in the same manner as in Example 3, and the switching state was observed.

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

The measurement results are shown below.

1 death A℃ 3 death response speed 205 μsec 141 μ
sec 114 p sec Comparative Example 4 A liquid crystal composition was prepared in which only the exemplified compound 1-2.1-109 used when mixing the liquid crystal composition 24-R in Example 24 was used, and the other components were the same in weight parts. A ferroelectric liquid crystal device was prepared in the same manner as in Example 3 except that compound 24-Rb was mixed and injected into the cell, and the optical response speed was measured.

The measurement results are shown below.

15℃ A℃35℃ jelJM 235μsec 158μsec
119 μsec As is clear from Example 24 and Comparative Example 4, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. has also been reduced.

Example 25 Exemplary compound 1-2.1-109 used in Example 24 and liquid crystal composition R were mixed in the weight parts shown below to prepare liquid crystal composition 25-R.

Exemplary compound No., parts by weight 1-2 3.51-
109...1.5 Liquid crystal composition R95,0 A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used. The optical response speed was measured and the switching state was observed.

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

The measurement results are shown below.

1 death Muscle °C Part °C Response speed 275 μsec 180 μ
sec 155 μsec Comparative Example 5 Except for injecting into the cell the liquid crystal composition R used when mixing liquid crystal composition 25-R in Example 25 <Example 3
A ferroelectric liquid crystal device was fabricated using the same method as described above, and the optical response speed was measured.

The results are shown below.

1 generation 25℃ 35℃ Response speed 315 p sec 213
μsec 159 g sec As is clear from Example 25 and Comparative Example 5, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has better operating characteristics at low temperatures.
High-speed response has been improved, and the temperature dependence of response speed has also been reduced.

Example 26 Exemplary compound 1-2 used in Example 23. 1-109
゜2-16.2-24.2-54.2-67, 3-69
．． Liquid crystal composition 26-R was prepared by mixing the following exemplified compounds in the weight parts shown below in place of No. 3-94.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 265 μsec 179 μ
sec 148 μsec Example 26 and Comparative Example 5
As is clearer, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of the response speed.

Liquid crystal composition R 匍, O Example 27 Exemplary compound 1-2 used in Example 23. 1-109
゜2-16.2-24.2-54.2-67, 3-69
．． Liquid crystal composition 27-R was prepared by mixing the following exemplified compounds in the weight parts shown below in place of No. 3-94.

Exemplary Compound No. Structural Formula Parts by Weight Exemplary Compound No.

Structural Formula A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used.The optical response speed was measured in the same manner as in Example 3, and the switching state was observed. .

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

The measurement results are shown below.

15℃ Part℃ 3-death response speed 200 μsec 1341
sec 112 p sec Comparative Example 6 Exemplary compound 1-17.1-61.1-45 used when mixing liquid crystal composition 27-R in Example 27 was not used, but the others were of the same weight. Part of liquid crystal composition 27-Rh
A ferroelectric liquid crystal device was prepared in the same manner as in Example 3 except that the mixture was mixed and injected into the cell, and the optical response speed was measured.

The results are shown below.

1 dead part °C 3 generations response speed 228 μsec 154 p
sec 115μ As is clear from Example 27 and Comparative Example 6, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and Dependency has also been reduced.

Example 28 Exemplary compound 1-2 used in Example 23. l-109
゜2-16.2-24.2-54.2-67, 3-69
．． Liquid crystal composition 28-R was prepared by mixing the following exemplified compounds in the weight parts shown below in place of No. 3-94.

Example Compound No., Structural Formula: Part by Weight Exemplary Compound No., Structural Formula: Part by Weight υ A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used. The optical response speed was measured in the same manner as above, and the switching state was observed.

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

The measurement results are shown below.

15@c Pit 3 Death Deception Crossing Zoo μsec 72 p sec
58 p sec Comparative Example 7 Exemplary compound 1-11 used when mixing liquid crystal composition 28-R in Example 28. Instead of using only 1-49.1-55, liquid crystal composition 28-R was used in the same weight parts.
A ferroelectric liquid crystal device was prepared in the same manner as in Example 3 except that h was mixed and injected into the cell, and the optical response speed was measured.

The measurement results are shown below.

15'C25@C35'C Response speed 1151 sec 76 B
sec 60 B sec Liquid Crystal Composition R Boiling As is clear from Example 28 and Comparative Example 7, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures. , the temperature dependence of the response speed is also reduced.

Example 29 Exemplary compounds used in Example 23 1-2.1-109°2-16.2-24.2-54.2-67, 3-69.
Liquid crystal composition 29-R was prepared by mixing the following exemplified compounds in the weight parts shown below in place of No. 3-94.

Exemplified Compound No. Structural Formula Weight Parts -18 Exemplified Compound No.

Structural Formula A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3 and the switching state was observed. .

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

The measurement results are shown below.

15℃ Part'0 35℃ Response speed 112 p sec 76 μs
ec 65 p sec Comparative Example 8 Exemplary compound 1-20 used when mixing liquid crystal composition 29-R in Example 29. 1-72. Instead of using only 1-80, liquid crystal composition 29-80 was used in the same weight parts.
All except mixing Rb and injecting it into the cell <Example 3>
A ferroelectric liquid crystal device was created using the same method as described above, and the optical response speed was measured.

The results are shown below.

1st death 25℃ 3rd death Response speed 130 psec 89 μs
ec 68 μsec Liquid Crystal Composition R 6 As is clear from Example 29 and Comparative Example 8, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures; The temperature dependence of response speed is also reduced.

Example 30 The following exemplified compounds were mixed in the following parts by weight to prepare liquid crystal composition S.
It was created.

Exemplified Compound No. Structural Formula Parts by Weight 30 Exemplified Compound No.

Structural Formula Further, the following exemplified compounds were mixed with the liquid crystal composition S in the weight parts shown below to obtain a liquid crystal composition 30.
-8 was created.

Exemplified Compound No. Structural Formula Weight Parts 59 Add-15 Exemplified Compound No.

Liquid Crystal Composition S Structural Formula A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. I observed the condition.

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

The measurement results are shown below.

05℃ Raw temperature 35℃ Response speed 335 p sec 215
μsec 178 μsec Comparative Example 9 Exemplary compound 1-2 used when mixing liquid crystal composition 30-8 in Example 30. 1-9. 1-16. 1-3
Instead of using only 4, liquid crystal composition 3O-3b was mixed in the same weight parts and injected into the cell.
A ferroelectric liquid crystal device was produced in the same manner as in Example 3, and its optical response speed was measured.

The measurement results are shown below.

15℃ 25''c35'C Response speed 385 μsec 231 μ
sec 180μ As is clear from Example 30 and Comparative Example 9, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures, and Dependency has also been reduced.

Example 31 Exemplary compound 1-2.1-9゜1- used in Example 30
16.1-34.2-15.2-19.2-25.2-
29 and Liquid Crystal Composition S were mixed in the weight parts shown below to prepare Liquid Crystal Composition 31-3.

Exemplary compound no.

-2 -9 -16 -34 -15 -19 -25 -29 Liquid crystal composition S A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that this liquid crystal composition was used. The optical response speed was measured in the same manner as in Example 3, and the switching state was observed.

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

The measurement results are shown below.

16℃ 25℃ 35℃ Response speed 595 μsec 4054
sec 285 μsec Comparative Example 1O Exemplary compound 1-2 used when mixing liquid crystal composition 31-8 in Example 31. 1-9. 1-16. 1-3
Instead of using only 4, liquid crystal compositions 3l-8b were mixed in the same weight parts and injected into the cell.
A ferroelectric liquid crystal device was produced in the same manner as in Example 3, and its optical response speed was measured.

The measurement results are shown below.

15℃ 2g'c A℃ response speed
685μsec 466μsec
2914 secAs is clear from Example 31 and Comparative Example 1O, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. Sexuality has also been reduced.

Example 32 Exemplary compound 1-2.1-9゜1- used in Example 30
16.1-34 and Liquid Crystal Composition S were mixed in the weight parts shown below to prepare Liquid Crystal Composition 32-8.

Exemplary Compound No. Parts by Weight -2 -9 -16 -34 Liquid Crystal Composition S A ferroelectric liquid crystal device was produced in the same manner as in Example 3 except that this liquid crystal composition was used. The optical response speed was measured in the same manner as above, and the switching state was observed.

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

The measurement results are shown below.

15℃ A'Ic 35℃ Sarobatsuwatari 735
B sec 500 p sec 360
μsec Comparative Example 11 Except for injecting the liquid crystal composition S used when mixing liquid crystal composition 32-8 in Example 32 into the cell, all <Example 3
A ferroelectric liquid crystal device was created using the same method as described above, and the optical response speed was measured.

The results are shown below.

15℃ Pile part℃ Response speed 905 μsec 611 μ
sec 381 p sec As is clear from Example 32 and Comparative Example 11, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has better operating characteristics at low temperatures.
High-speed response has been improved, and the temperature dependence of response speed has also been reduced.

Example 33 Exemplary compound 1-2.1-9゜1- used in Example 30
16. l-34, 2-15, 2-19, 2-25, 2
In place of -29°3-7.3-13.3-92, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 33-8.

Exemplified Compound No. Structural Formula Weight Parts υ Liquid Crystal Composition S A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used. The optical response speed was measured and the switching state was observed.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 740 μsec 495 B
sec 345 μsec As is clear from Example 33 and Comparative Example 5, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and Dependency has also been reduced.

Example 34 Exemplary compound 1-2 used in Example 30. 1-9゜1
-16.1-34.2-15.2-19.2-25.2
In place of -29°3-7.3-13.3-92, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 34-8.

Exemplified Compound No. Structural Formula Parts by Weight -7 Exemplified Compound No.

Structural formula exemplified compound No. Structural formula: Parts by weight - 113 Except for using this liquid crystal composition, a ferroelectric liquid crystal element was prepared in the same manner as in Example 3, and the optical response speed was measured in the same manner as in Example 3. The switching state was observed.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 593 μsec 403 μ
sec 283 μsec Comparative Example 12 Exemplary Compound 1-48. used when mixing liquid crystal composition 34-S in Example 34. 1-53. 1-71
A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that liquid crystal composition 34-Sb was mixed in the same weight parts and injected into the cell. , the optical response speed was measured.

The results are shown below.

1 death 25℃ 3 death response speed 695 p sec 4753
sec 287μ formula Example 34 and Comparative Example 12
As is clearer, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of the response speed.

Example 35 Exemplary compound 1-2.1-9゜1- used in Example 30
16.1-34.2-15.2-19.2-25.2-
In place of 29°3-7.3-13.3-92, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 35-8.

Exemplary Compound No. Structural Formula Parts by Weight Exemplary Compound No.

Structural formula % Formula % Structural formula weight part -70 -1 -16 -20 -41 -61 Liquid crystal composition S All except that this liquid crystal composition was used.A ferroelectric liquid crystal element was prepared in the same manner as in Example 3. was prepared, the optical response speed was measured in the same manner as in Example 3, and the switching state was observed.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 313 p sec 205
p sec 172 μsec Comparative Example 13 Exemplary Compound 1-4 used when mixing liquid crystal composition 35-8 in Example 35. 1-8.1-49. , 1-63
Ferroelectric composition was prepared in the same manner as in Example 3 except that liquid crystal composition 35-5b was mixed with liquid crystal composition 35-5b in the same weight parts and injected into the cell. We created a liquid crystal device and measured its optical response speed.

The results are shown below.

15℃ Raw temperature 35℃ Response speed 362 μsec 233 μ
sec 178 μsec Example 35 and Comparative Example 1
As is clear from No. 3, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of the response speed.

Example 36 Exemplary compound 1-2.1-9゜1- used in Example 30
16.1-34.2-15.2-19.2-25.2-
In place of 29°3-7.3-13.3-92, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 36-8.

Exemplary Compound No. Structural Formula Part by Weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3. and observed the switching state.

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

The measurement results are shown below.

15℃ 25℃ 3511c response speed
718Bsec 487μsec
365 μsec As is clear from Example 36 and Comparative Example 5, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. Sexuality has also been reduced.

υ Liquid crystal composition S 9 Example 37 Exemplary compound 1-2.1-9゜1- used in Example 30
16.1-34.2-15.2-19.2-25.2-
In place of 29°3-7.3-13.3-92, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 37-8.

Exemplary Compound No. Structural Formula Parts by Weight Exemplary Compound No.

-2 -7 Structure Construction formula %formula% formula Weight part Exemplary compound no.

Structural Formula A ferroelectric liquid crystal element was prepared in the same manner as in Example 3 except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 3 and the switching state was observed. .

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

The measurement results are shown below.

15 degrees Celsius Celsius response speed 555 μsec 381 p
sec 283 μsec Comparative Example 14 Exemplary compound 1-2.1-7.1-38 used when mixing liquid crystal composition 37-8 in Example 37. 1-54° and 1-87, and the same weight parts of liquid crystal composition 37-8b were mixed and injected into the cell. We created a ferroelectric liquid crystal device and measured its optical response speed.

The results are shown below.

15℃ 25℃ 35℃ Response speed 645 p sec 429
μsec 286 μsec As is clear from Example 37 and Comparative Example 14, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has better operating characteristics at low temperatures.
High-speed response has been improved, and the temperature dependence of response speed has also been reduced.

Example 38 Exemplary compound 1-2.1-9゜1- used in Example 30
16.1-34.2-15.2-19.2-25.2-
In place of 29°3-7.3-13.3-92, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 38-8.

Exemplified Compound No. Structural Formula Weight Parts-6 Su-17 Exemplified Compound No.

Structural formula exemplified compound No. Structural formula Parts by weight -62 A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that this liquid crystal composition was used, and an optical The response speed was measured and the switching state was observed.

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

The measurement results are shown below.

15℃ Evil℃ A℃Response speed
250 psec 176 psec
130 g sec Comparative Example 15 A liquid crystal composition was prepared without using only Exemplified Compound 1-49.1-71, which was used when mixing Liquid Crystal Composition 38-8 in Example 38, and using the same weight parts of each other. A ferroelectric liquid crystal device was prepared in the same manner as in Example 3 except that 38-3b was mixed and injected into the cell, and the optical response speed was measured.

The results are shown below.

1 death Muscle temperature 35°C Response speed 360 p sec 245
p sec 165 μsec Example 39 Exemplary compound 1-2 used in Example 30. l-9゜1-16.1-34.2-15.2-19.2-25.
In place of 2-29°3-7.3-13.3-92, the following exemplified compounds were mixed in the weight parts shown below to prepare liquid crystal composition 39-8.

Exemplary Compound No. Structural Formula Part by weight As is clear from Example 3B and Comparative Example 15, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures. , the temperature dependence of the response speed is also reduced.

Exemplary compound no.

Structural formula % Formula % Structural formula weight part -82 Su-102 Liquid crystal composition S 1 A ferroelectric liquid crystal element was produced in the same manner as in Example 3 except that this liquid crystal composition was used. The optical response speed was measured in the same manner as in Example 3, and the switching state was observed.

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

The measurement results are shown below.

15℃ 25℃ 35℃ Response speed 321 μsec 207 p
sec 175 μsec Comparative Example 16 Exemplary Compound 1-2 used when mixing liquid crystal composition 39-8 in Example 39. 1-21. 1-90. 1-
A ferroelectric liquid crystal element was prepared in the same manner as in Example 3, except that liquid crystal composition 39-3b was mixed with the liquid crystal composition 39-3b in the same weight parts and injected into the cell. was created and the optical response speed was measured.

The measurement results are shown below.

15℃ 25℃ Sting response speed 369 μsec 230 μ
sec 178 μsec As is clear from Example 39 and Comparative Example 16, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures, and Dependency has also been reduced.

〔Effect of the invention〕

As explained above, a device using a ferroelectric liquid crystal composition containing a liquid crystal compound of the present invention has good switching characteristics, a liquid crystal device with improved low-temperature operation characteristics, and a temperature dependence of response speed. It is possible to obtain a liquid crystal element with reduced .

[Brief explanation of drawings]

FIG. 1 is a schematic cross-sectional view of an example of a liquid crystal element using ferroelectric liquid crystal. 2 and 3 are perspective views schematically showing an example of an element cell for explaining the operation of a ferroelectric liquid crystal element. In Figure 1, l・・・・・・・・・・・・・・・・・・・・・
...... ...... Ferroelectric liquid crystal layer 2
・・・・・・・・・・・・・・・・・・・・・Track song・Glass substrate between songs 3・・・・・・・・・・・・・・・・・・
...... Song... Song...
...Song...Song transparent electrode 4...
・・・・・・・・・・・・・・・・・・・・・・・・
...Insulating orientation control layer 5 ......
··············· ···while····
・・・・ Spacer 6 ・・・・・・・・・・・・
・・・・・・・・・・・・・・・・・・・・・・・・
...Lead wire 7... ...
・・・Song ・・・Song 11 Source 8・・・・・・・・・・・・
... Polarizing plate 9 ...
... Light source IO incident light!・・・・・・・・ In the transmitted light figure 2, 21a ・・・・・・・・・・・・・・・・・・
...Song Substrate Substrate Ferroelectric liquid crystal layer Liquid crystal molecule dipole moment (on P) In Fig. 3, 1a tb 3a 3b 4a 4b a b Voltage application means Voltage application means First stable state Second stable state State Upward dipole moment Downward dipole moment Upward electric field Downward electric field

Claims (1)

[Claims] (1) The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (However, R_1 and R_2 are straight lines that may have a substituent having 1 to 16 carbon atoms. It is a chain or branched alkyl group. Y_1 is -COO-, -OCO-, -CH_2O-, -
OCH_2-, Z_1 is a single bond, -O-, -CO
O-, -OCO-, -OCOO-. Moreover, X is a halogen, cyano, or methyl group. ) A liquid crystalline compound represented by (2) A liquid crystal composition containing at least one kind of the liquid crystal compound according to claim 1. (3) The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (However, R_1 and R_2 are linear or branched structures that may have substituents having 1 to 16 carbon atoms. It is an alkyl group. Y_1 is -COO-, -OCO-, -CH_2O-, -
OCH_2-, Z_1 is a single bond, -O-, -CO
O-, -OCO-, -OCOO-. Moreover, X is a halogen, cyano, or methyl group. ) and the following general formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) (However, R_3 and R_4 are linear or branched compounds having 1 to 18 carbon atoms. represents an alkyl group. These may have an alkoxy group having 1 to 12 carbon atoms as a substituent. However, they are non-optically active. Z_2 and Z_3 are single bonds, -O-, ▲ formula, chemical formula, table, etc. ▼, ▲ mathematical formula, chemical formula, table, etc. ▼, where p and q are 0, 1, or 2). A liquid crystal composition. (4) The following general formula (I
II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) (However, R_5 is a carbon number of 1 which may have a substituent.
~18 linear or branched alkyl groups. Y_2
is a single bond, -COO-, -OCO-, -COS-, -S
CO-, -CH_2O-, -OCH_2-, -CH=C
H-COO-, Z_4 is a single bond, -O-, -CO
O-, -OCO-, Z_5 is -OCH_2-, -CO
OCH_2-, -OCO-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas There are tables, etc. ▼. Further, l is an integer of 1 to 12, and k is an integer of 1 to 4. 3. The liquid crystal composition according to claim 2, further comprising at least one liquid crystal compound represented by: (5) A liquid crystal element, characterized in that the liquid crystal composition according to claim 2 is disposed between a pair of electrode substrates. (6) A liquid crystal element, characterized in that the liquid crystal composition according to claim 3 is disposed between a pair of electrode substrates. (7) A liquid crystal element, characterized in that the liquid crystal composition according to claim 4 is disposed between a pair of electrode substrates.