CA1341098C - Liquid crystal composition and use thereof - Google Patents

Abstract

The present invention is directed to a liquid crystal composition which comprises at least one liquid crystalline compound having an optically active .gamma.-lactone ring of the formula (A):
wherein R1 is a group selected from the group consisting of

Description

'!34 1090 LIQUIL> CRYSTAL COMPOSITION AND USE THEREOF
This i.nventi.on relates to a liquid crystal composition useful as an element for display devices or an element for opt:o-elec;tronics devices.
Liquid crystals have widely been used as a material for display devices, where a TN (Twist;ed Nematic) type display system is usually employed. Advantages of this TN
display system include less electric consumption, less eye fatigue because it is a receptor type, and the like. On the other hand, this system is disadvantageous in that the driving force is very weak as it is driven mainly on the basis of anisotropy of relative dielectric constant and is slow in response speed. Hence, this system cannot be applied to devices which require high response speed.
A liquid crystal having ferr~electricity were first found by Ft. H. Meyer et al. in 1975 (cf. J. Physique, 36, L-69, 1975. This liquid crystal is driven by a comparatively large force derived from spontaneous polarization, shows extremely high response speed and has good memory. Owing to such excellent properties, the ferroelectric liquid crystal has been noticed as a new type of display element. In order to exhibit the ferro-electricity, tree liquid crystalline compounds should show chiral smectic: C phase (SmC* phase) and thus should contain at least one asymmetric carbon atom in the molecule. It is also necessary to have a dipole morr~ent in the direction vertical to the long axis of the molecule.
A ferroelectric liquid crystal DOBAMBC synthesized by Meyer et a~_. has the following formula:
iH3 C10H210~~CH=N ~ ~ CH=CH-C'02CH2-~H-CH2CH3 and satisfies the above conditions, but it contains a Schiff base and hence' is chemically unstable and show a spontaneous pola.rizatic~n as low as 3 x 10 9 C/czn2. Since then, there have been synthesized many ferroelectric liquid crystalline compounds, but any practically useful compound having sufficently high response speed has yet to be ~ found.
Amon<~ the ~;nown ferroelectric liquid crystalline compounds, DOBA-1-MBC which has the asymmetric carbon atom at the position nearer to the carbonyl group than in DOHAMBC
and has the following formula:
iH3 C10H210~~CFi=N ~ ~ CH=CH-C:OZ~H-C3H~
shows a spontaneous polarization of 5 x 10 8 C/cm2 which is larger than that of DOBAMBC. It is, assumed that this is caused by t:he following difference. The asymmetric carbon atoms and the dipole which are important factors for the appearance of ferroelectricity are positioned close to each other, and thereby, the free rotation of the dipole moiety of molecule is restricted and then the orientation of the dipole is increased. Thus, it is assumed that the known ferroelectric liquid crystalline compounds cannot give satisfactory spontaneous polarization and high respor.,se speed because the asymmetric carbon atom having an inhit~itory action of the free rotation of molecule is present on the linear chain in the known ferroelectric .LO liquid crystalline compounds and hence the free rotation of molecule cannot completely be inhibited and the dipole moiety cannot be fixed.
The present inventors have studied intensively the .L5 inhibition of free rotation of dipole moiety in the conventional ferroelectric liquid crystalline compounds and have found that: the free rotation can be inhibited by providing a compound wherein the asymmetric carbon atom is contained in a 5-membered lactone ring, by which there can :?0 be obtained a chemically stable liquid crystalline compound having ferroelectricity. The present inventors have already filed a patent application for said liquid crystalline compound, Thug;, an object of the present invention is to provide a novel liquid crystal composition which comprises 25 at least one of said liquid crystalline compounds, i.e.
compounds having an optically active Y-lactone ring in the mo~~ecule 'wherein one or two asymmetric carbon atoms are present in the 5-membered lactone ring, or compounds having a specific substituent on the phenyl ring of the above compounds. Another object of the invention is to provide an elemen~ for opto-electronic devices comprising saicz liquid crystal composition. These and other objects and advantages of the invention will be apparent to those skilled in the art from the following description.
In drawings which are directed to preferred embodiments of the present invention:
Fig. ~_ shows a graph of the relationship between the relative d__electric constant and temperature in the liquid crystal composition prepared in Example 1.
Fig. ? shows a graph of the relationship between the relative d:_elect~ic constant and temperature in the liquid crystal composition prepared in Example 2.
Fig. :3 shows a graph of the relationship between the relative dielectric constant and temperature in the liquid crystal compo:~ition prepared in Example 5.
Fig. ~~ show;s a graph of the relationship between the relative dielectric constant and temperature in the liquid crystal composition prepared in Example 8.
The liquid crystal composition of this invention comprises at least o;ne liquid crystalline compound having an optically active Y-lactone ring and having the following formula (A):

R 1-0~~\\* R 2 (A) wherein Rl is ~3 group selected from the group consisting of X Y X Y
N
R3--f0 n / \ ~~- and R3--f0 n / ~~ / \ / \
~N
n and a are each independently 0 or 1; R3 is an alkyl group having 1 to 15 carbon atoms; X and 5.' are each independently a group selected frorn the group con:;isting of a hydrogen atom, a h a 1 o g a n atan and a cyano group; R 2 i s a g r o a p o f t h a f o r mu 1 a : - ( CO ) rn-R 4 ; m i s 0 o r 1; R 4 i s a hydrogen at~n or an alkyl group ha~~ing 1 to 15 carbon atoms; and the symbol * is an asymmetric carbon atom, and a chiral or non-chiral liquid crystal.
In the specification, the germ "alkyl group" for R3 and R4 includea methy:L, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-hepvyl, n--octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, isopropyl, t-butyl, 2-metlzylpropyl, 1-methylpropyl, 3-methylbutyl, 2-methylbutyl, 1-methy:Lbutyl, 4-methy7.pentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 5-methylhexyl, 4-methyl-hexyl, 3-methy:Lhexyl, 2-methylhexyl, 1-methylhexyl, 6-methylheptyl, '~-methylheptyl, 4-methylheptyl, 3-methyl-heptyl, 2-meth:~lheptyl, 1-methylhept:yl, 7-methyloctyl, 6-methyloctyl, 5-methy:Loctyl, 4-methyl.octyl, 3-methyloctyl, 2--s-13~ 1098 methyloctyl, 1--methy'~octyl, 8-methylnonyl, 7-methylnonyl, 6-methylnonyl, 5--methy7.nonyl, 4-methylnonyl, 3-methylnonyl, 2-methylnonyl, 1--methy~nonyl, 3,7-dimethyloctyl, 3,7,11-tri-methyldodecyl, and the like.
The compounds of this invention contain a carbonyl group within a 5-membered ring and one or two asymmetric carbon atoms on the ring as a moiety having a dipole moment as an origin oi= ferroelectricity, anal hence, the free rotation at this moiety is inhibited. and thereby the dipole moiety is directed to one direction, which is effective to enlarge the spontaneous polarization and to increase the response speed. In the liquid crystalline compounds (A) of this invent:LOn, when the benzene rings) in R1 has a substituent of a halogen atom or cya.no group, the compound has a reduced meltin<~ point, a widen temperature range of chiral smectic C phase which broadens to a low-temperature side and a larder ti:Lt angle effective to increase spontaneous po:Larization. Further, the introduction of cyano group provides a compound having a large negative dielectric anisotropy, which negative dielectric anisotropy is necessary fc~r driving the ferroelectric liquid crystal.
When R2 is a hydrogen atcan, only one asymmetric carbon atom is contained, but when RZ is a group other than hydrogen, two asymmetric carhon atoms are contained in the Y-lactone ring and hence there are present two kinds of diastereomer.
These are all ;~uitab:Le for inhibition of free rotation of the dipole moiety, anal they are used as a liquid crystal alone or in a rr~ixture~ of two or more thereof. The liquid crystalline compound used in this invention includes not only the compound which is in the liquid crytalline state alone but also the campound which does not take the liquid crystalline form by itself but still is useful as a component of a liquid; crystal composition.
The compounds (A) of the invention can be prepared by a process which comprises reacting an optically active lp glycidyl ether of the formula (B):
*
Rl- ~\ (B) wherein R1 and the symbol * are the same as R1 and * in the formula (A), with a s-ketoester of the formula (C) or a 1'.~ malonate of they formula (D), respectively:
o a 9./ V I \ 5 R OR (C) _ 0 O
5 ~f ~~ 5 2 0 R t) OR ( D ) Rf wherein R4 is hydrogen atom or an alkyl group having 1 to 15 carbon atoms and R5 i.s a lower alkyl group having 1 to 4 carbon atoms, i.n the presence of a base in an organic solvent.

- g _ The desired compound (A) of this invention can be prepared by reacting under reflux t:he compound (B) with 1 to equivalents of the compound (C) or the compound (D) in the presence of 1 to 5 Equivalents of a base in an organic 5 solvent for 1.5 to ;?4 hours. The base used therein includes alkali metal <ilkoxid es (e. g. sodium methoxide, sodium ethoxide, pot<~ssium t-butoxide, etc.), alkali metal hydrides (e. g. sodium llydridE~, lithium hydride, etc.), and alkyl alkali metals (e. g. n-butyllithium, etc.), and the organic solvent includes alcohols (e. g. methanol, ethanol, t-butyl alcohol, etc.~, ethers (e. g. tetrahydrofuran, diethyl ether, dimethoxyethane, diEethylene glycol dimethyl ether, dioxane, etc.), aprotic~ polar solvents (e.g. dimethylformamide, di-methylsulfoxide, hexamethylphosphoric triamide, etc.), and a mixture of these so:Lvents.
In the above process, when R4 in the compound (D) is a hydrogen a.tcxn, t~.e final compound prepared by the above process is mixed with an inorganic salt (1 to 10 equivalents) and waiver under neutral conditions and then is refluxed in a polar solvent to give the desired compound (A). The solvent used therein includes polar solvents, e.g.
dimethylformamide, dimethylacetamide, dimethylsulfoxide, hexamethylpho:~phoric triamide, diet:hylene glycol dimethyl ether, dioxanc~, and the like. The inorganic salt includes alkali metal or alkaline earth metal halides, e.g.
lithium chloride, sodium chloride, potassium chloride, _ g _ lithium bromide, sodium bromide, potassium bromide, lithium iodide, sodium iodide, potassium iodide, magnesium chloride, calcium chloride, strontium chloride, barium chloride, magnesium bromide, calcium bromide, barium bromide, magnesium iodide, calcium iodide, barium iodide, and the like. Water is preferably used in an amount of 5 to 50 equivalents. The reaction is completed in 1 to 15 hours.
The starting optically active glycidyl ether (B) can be prepared by a process as shown in the following reaction scheme:
*/ 'C1 ~/
0~
RlOH -~ R1-O
Ease O
wherein R1 anc~ the symbol * are the same as R1 and * in the formula (A).
That is, a phenol derivative of the formula R10H is reacted with am optically active epichlorohydrin in the presence of a base. The optically active epichlorohydrin is preferably used in an amount of 1 to 10 equivalents to the phenol derivative, a,nd the base is preferably used in an amount of 1 tt~ 5 equivalents to the phenol derivative. The base includes alkali. metal hydroxides or alkoxides, e.g.
sodium hydroxide, potassium hydroxide, potassium t-butoxide, and the like. The above reaction proceeds smoothly without any catalyst, but may be carried out in the presence of a catalyst. The catalyst includes quaternary ammonium halides, e.g. ber~zyltriethylammonium chloride, benzyl-triethylammoni.um bromide, benzyltrimethylammonium chloride, benzyltrimeth~~lammonium bromide, etc. and is used in an amount of 0.01. to 0.1 equivalent to the phenol derivative.
An excess amount of the optically active epichlorohydrin may be used as the solvent, but there is preferably used a suitable polar solvent, e.g. dimethylformamide, dimethyl-sulfoxide, dimethylacetamide, acetonitrile, t-butyl alcohol, and water. The reaction is usually carried out at a temperature of: 50 to 80°C for 0.5 to 3 hours.
Alternatively, the optically active glycidyl ether (B) may also be prepared by reacting the phenol derivative of the formula R10H with an optically active epichlorohydrin in the presence of a n amine (e. g. morpholine, piperidine, pyridine, etc") of 0.1 to 0.5 equivalent to the phenol derivative an~i subjecting the resulting optically active chlorohydrin derivative to cyclizat.ion reaction with 1 to 5 equivalents of. a base, for example an alkali metal hydroxide, carbonate or alkoxi<ie (e. g. sodium hydroxide, potassium hydroxide, potassium carbonate, sodium carbonate, potassium t-butoxide, et:c.). The latter process is carried out in two steps but is advantageous in that the extraction of the product can easily be done. This reaction is usually carried out at: a temperature of 50 to 80°C for 3 to 24 hours.

When a racemic epichlorohy~irin is used in the above reaction, there is obtained a glycidyl ether in the form of a racemic mixture. ~Che starting optically active epichloro-hydrin can be prepared in high purity by the processes as described in United States Patent No. 4,840,907 (as to R isomer) and by the procesa as described in Japanese Patent Application No. 28:3393/1987 (as to S isomer).
Besides, the starting phenol derivative used for the preparation of the compound (B) can be prepared by the processes as shown in the following Reaction Schemes-I to -VI, wherein R'; is the same as R3 in the formula (A), R3 is hydrogen atom or an alkyl group having a carbon atom one smaller than that in R3, Ph means phenyl, and R' is a lower alkyl group having 1 to 4 carbon atoms.
That is, 4-(4-trans-alkylcyclohexyl)phenols, 4-(4-alkyloxyphenyl;ipheno:Ls and 4-(4-alkylphenyl)phenols are prepared by the' known processes as shown in Reaction Schemes-I, -II and -III, respectively.

- is -Reaction Scheme-I
R3~COC1 ~ W
R3 CO-~,, ~-C1 -j R3 CO /
A1C13 ' A1C13 NHZNH2~H20 R3'CH2 / \
A1C13 ~, CH3COC1 1) H202, HC02H
R3 CH2~~~ OH ~2) H O+ R3 CH2 ~ ~ -COCH3 Reaction Scheme-II

CH3C02 ~ ~ ~~ 3 ~. CH3C02 / ~' ~ ~ COCH3 y H30+
HO / ~ / ~ COCH3 R30 / \ ~ ~ 'OH ~ H202' HC02H R30 / ~ / \ COCH
c. ) H30+ 3 Reaction Scheme-III
R~~COC1 CH3C02 / ~ ~_~ - ~. CH3C02 ~ ~ / ~ COR3 NH2NH2~H20 H0~ ~ ~ / ~ -CH2R3 Also . 4--(5-alkyl-2-pyrimidinyl)phenols and 4-(5-alkyloxy-2-pyrimidinyl)phenols are prepared by the processes as shown in the following Reaction Schemes-IV and -V, respectively, which are disclosed in Japanese Patent First Publication (Rokai) Nos. 189274/1986 and DE 144,409.
Reaction Scheme-IV
3 (CH3)2NCH0 3 ~CHN(CH3)2 R CH2CH(OC2H5)2 -~ R C~ \

1) C2H50H, HC1 ~NH
HO ~ ~ -CN -~ HO ~ ~ -C~ ~ HC 1 2) NH3 ~~NH2 ~ NaOC2H5 R3-(' N> / ~ -OH
~N
H2 '~ Pd-C
Cl R 3 / N~ / ~ -OH

R3CH(C02C2H5)2 i ~POC13 Rj N\ ~ ~ OH
N

Reaction Scheme-V
R30H + HrCH2C~:f(OC2H5)2 ~ R30CH2CH(OC2H5)2 (CH3)2NCH0 - POC13 ~ /NH
HO-C/ '>-C~ ~HC1 ,,~~JJ \
R30~N\~ / ~ ~OH .~ NH2 R30C~CHN ( CH3 ) 2 N~ NaOC2H5 ECHO
Morecwer, 4-(5-(4-alkyloxyphenyl)-2-pyrimidinyl]-phenols and 4-~[5-(4-~alkylphenyl)-2-pyrimidinyl]phenols are prepared by the proc:esses as shown in the following Reaction Scheme-VI.
Reaction Scheme-VI
HO ~ ~ -CN HO / \ -CF:(2COZH R3 / \ -COCH3 ~~ PhCH2C7. R' OH ~~ H+~ S
N
PhCH20 / ~ -CtJ HO / \ -CH2C02R' R3 / \ -CH2C02H
1 ) C2Hc~OH, HC:I R3X ,y ~ R' OH, H+
2) NH3 ,NH R30 ~ \ C~:(2C02R' R3 / ~ -CH2C02R' PhCH20 ~ ~ -C~~ ~HCl ~NH2 OR' (E) /OR\ 0=C\
0=C ~ OR
FOR' R3~~~ n / \ _CH ( C02R' ) 2 NaOC2H5 - ~ (F) n = 0 (G) n = 1 R3~0 n / \ ~~N~ /-~ OCH2Ph -N
0 ~ H POC13 N
R3--i,C1 n / ~ / ~ / ~ OCH2Ph -N

H2 y Pd-C
R3~~~ n / \ ~N / \ OH
N
(H) n = 0 (I) n = 1 13~ 1098 According t.o the process of Reaction Scheme-VI, Compound (E) i.s prepared by protecting the hydroxy group of p-hydroxybenzoni.trile with benzyl group and converting the cyano group thereof into amidine hydrochloride in a usual manner. Separately,. p-hydroxyphenylacetic acid is esteri-fied with a lower alcohol, and the phenolic hydroxy group is alkylated with an a:Lkylating agent, e.g. an alkyl halide, an alkyl p-to:Luenesu:Lfonate or an alkyl methanesulfonate, followed by reaction with diethyl carbonate in the presence of a base to ~3ive diethyl malonate derivative (G).
The ;amidine hydrochloride (E) is condensed with the diethyl malon,ate derivative (G) in the presence of a base for example, alkali metal alkoxides (e.<~. sodium ethoxide, sodium methoxide, etc.), followed by reaction with phosphorus oxy-chloride in the presence of a base, for example, organic amines (e. g. N,N-diethylaniline, pyridine, 4-(N,N-dimethylamino)-pyridine, etc.). and the resulting compound is reduced with hydrogen gas in the presence of Pd-C catalyst to give the desired 4-[5-(4-alkyloxyphenyl)-2-pyrimidinyl]phenol (I).
In the above process, when a diethyl p-alkylphenyl-malonate (F) is used instead of the diethyl malonate derivative (C~) and the compound (E) and the compound (F) are reacted as in the reaction of the compound (E) and the compound (G),. there is prepared 4-[5-(4-alkylphenyl)-2-PYrimidinyl]phenol (H).
The diethyl p-alkylphenyl.malonate (F) can be prepared by subjecting a p-alkylacetophenone to Willgerodt reaction, esterifying the resulting phenylacetic acid derivative with a lower alcohol, and condensing the resultant proc.uct with diethyl carbonate.
Moreover, among the starting phenol derivatives used for the preparation of the compound (B), the phenol derivative wherein the benzene ring is substituted with a halogen atom or cyano group, can be prepared by the processes as shown in the following Reaction Schemes-VII to -XI, wherein R3, R3 and X are the same as defined in the above Reaction Schemes-I to VI and Ts means p-toluene-sulfonyl group.
That is, 4-(4-alkylphenyl)-2-halogenophenols and 4-(4-alkylphenyl)-2-cyanophenols are prepared by the process as shown in Reaction Scheme-VII.
Reaction Scheme-VII
X X X
CH3I 1) Mg HO / \ -Br --~ CH30 / \ Br - -~ CH30 / \
2) ~0 Chloranyl X
CH30 / \ /-\
R3~COC1~

X !~X
/ \ / \,_ 3 ~ NaBH4 / \ / \ 3' ~, HBr X CN
Cu2(CN)2 HO / \ ~ \ -C:H2R3 ~ HO / \ ./ \ -CH2R3 Besides, 4-(4-alkoxyphenyl)-2-halogenophenols and 4-(4-alkoxyphenyl)-2-cyanophenols are prepared by the known process as shown in the following Reaction Scheme-VIII, which is disclcsed Japanese Patent First Publication (Kokai) No. 166646/1985.
Reaction Scheme-VIII
Br Br2 R30 / ~ / ~ C~H -_ ~ R3p ~ ~ / ~ OH
dioxane Cu2(CN)2 ~, CN
R30 ~ ~ / ~ OH
Moreover, 4-(4-alkoxy-3-fluorophenyl )phenols are prepared by the known process as shown in the following Reaction Scheme-IX, which is disclosed in Abstract of the 12th Liquid Crystal Symposium, Nagoya, Japan, No.2, F18, 1986.
Reaction Scheme-IX
F F F
HO / ~ -Br R3x~ R3~, / ~ Br 1 ) Mg R30 2) ~~I' PdCl2 F F
R3C~ / ~ -~~OH 1~0+ R3p / ~ / ~ COCH3 2) H30 Besides, 4-(4-alkoxy-3-brorn.ophenyl)phenols and 4-(4-alkoxy-3-cyanophenyl)phenols are prepared by the known process as shown in t:he following Reaction Scheme-X, which is disclosed in Japanese Patent First Publication (Kokai) No. 166646/198G~.
Reaction Scheme-X
Br R30 / \ / \ OH T-~1R30 / \ / \ C.TS B~ R30 / \ / \ -OTs CN Br R30 ~~\~ / \ OH ~ ( CN ) 2 R3p / \ ~ \ OH
~J
Moreo«er, 4--(4-alkyl-2-pyrimidinyl)-2-halogeno-phenols and 4-(5-alkyl-2-pyrimidinyl)-2-cyanophenols are prepared by the' known process as shown in the following Reaction Scheme'-XI, which is disclosed in Abstract of the 13th Liquid Crystal Symposium, Fukuoka, Japan, 1Z 06, 1987.
Reaction Scheme'-XI
X X X
CFi3I
HO / \ Br ~ CH30 ~ ~ Br -~ CH30 '/ \ CN
1) HC1-CH30H
2) NH3-C2H50H
~CHN(CH3)2 X Ft'3 -C X
N~ ECHO NH2 CH30 ~ \ ~ ~-R3 ~ . CH30 /-~ ~HC1 NJJ NH
,~ HBr X CN
OH-% \ ~~ \ R:3 Cu 2 { C~ HO ,~ ~%N \ R3 N ~ ~~N

13~ 1098 Besides, 4-(4-alkylphenyl)-2-cyanophenols are prepared by the' known process as shown in the following Reaction Scheme-XII, which is disclosed in Japanese Patent First Publication (Kokai) No. 165331/1988.
Reaction Scheme-XII
~ 1) BC1 , CH SCN CN
R3 / \ ~OH 3 3 R3 \~ ~ ~ OH
2) NaOH aq.
The liquid crystal composition of this invention may be obtained by mixing at least one of the compound (A) as prepared above with a chiral or non-chiral liquid crystal.
The chiral or non-chiral liquid crystal employed in the liquid cry~;tal composition of this invention is not particularly limited but may be any conventional chiral or non-chiral liquid crystal which shows chiral smectic C phase after mixing with the compound (A).
A typi~~al example of the above chiral or non-chiral liquid crystal includes the compound of the general formula (J):
R ~ -W~~K-,~--~L-f-~~-~-M-R1, ( J ) wherein E, F and G are each independently a 6-membered ring selected from t:he group consisting of:
\ ~ I N~~.~ ~~Dl ~ / ~N~ , ',N~ ~ %-N~
~,N
N~ O~ O
and ~~-, the hydrogen atoms) ~~-N _ 0' O .

in the 6-membered ring being optionally substituted with a halogen atom, c~yano group or nitro group; a and b are each 0, 1 or 2 and c' is 1 or 2, but a+b+c = 2 to 4; W and M are each a single t~ond or a group selected from the group II II il II
consisting of -~C-, -C:-0-, -0-C-, -0-C-O-, -O-, -S-, II fl -CH=CH-C-O-, -O-C-CH=CH-, -CH20- and -OCH2-; K and L are each independer..tly a single bond or a group selected from 1. 0 O 0 II II
the group consisting of -C-0-, -0-C-, -CH20-, -OCH2-, O
II
-CH2CH2-, -CH=N-, -N=CH-, -CH=CH-, -C=C-, -CH=CH-C-O- and O
II
15 -O-C-CH=CH-, provided. that K is a single bond when a=0, and L is a single t~ond when b=0; R~ and R~~ are each independently a.n alkyl group having 1 to 15 carbon atoms, which may contain one or more asymmetric carbon atoms.
Particularly suitable examples of the chiral or 20 non-chiral liquid crystal are a compound of the formula (J-1):
N
R ~ ~~~ y / \ R.... ( J_1 ) N
wherein R "' and. R"" are the same or different and are each a 25 straight chain or branched chain alkyl group having 1 to 15 carbon atoms or a straight chain or branched chain alkoxy group having 1 to 15 carbon atoms, said alkyl and alkoxy groups having optionally one or more asymmetric carbon atoms, and a compound of the formula (J-2):

II II
wherein R "' and R"" are as defined above, A is -C-O- or -O-C-, and k and Q are independently 0 or 1, but k + ~, ~ 2.
The liquid crystal composition of this invention is useful for preparing a liquid crystal cell of an electric-ally controlled birefrigence mode or guest-host mode, which is prepared by attaching a transparent electrode to the liquid crystal composition of this invention, sandwiching the resultant electrode-attached liquid crystal composition with two sheets of glass plate which is surface-treated for orientation with a polymer (e. g. polyethylene, polyester, nylon, polyvinyl alcohol, polyimide, etc.), and providing a polarizer. The thus prepared liquid crystal cell can be used as an element for display devices or an element for opto-electronic devices.
The liquid crystalline comp~~unds (A) of this invention may be obtained in the form of a racemic mixture when a racemic epichlorohydrin is used as the starting material, and the racemic compounds may be added to other optically active liquid crystalline compounds in order to regulate the helical pitch thereof. The liquid crystalline compound (A) of this invention has excellent heat stability and light stability, and the liquid crystal composition comprising the liquid crystalline compound (A) shows a x c a 11 a n t p r op a r t i a s a s a f erroelectri.c liquid crystal . The liquid crystal composition comprising the liquid crystalline compound (A) of this invention and nematic liquid crystal is also useful for the following utilities.
(1) Liquid crystal composition of TN (Twisted Nematic) type or STN (Super Twisted Nematic) type liquid crystals wherein the compound (A) is effective to inhibit occurrence of reverse domain.
(2) Display element utilizing cholesteric -nematic phase transfer effects (cf. J.J. Wysoki, A. Adams and W. Haas; Ph.ys. Rev. Lett., 20, 1024, 1968).
(3) Display element utilizing White-Taylor type guest-host effects (cf. D.L. White and G.N. Taylor; J. Appl.
Phys., 45, 4718, 1974).
(4) notch filter or band-pass filter utilizing selective scattering effects by fixing the cholesteric phase in matrix (cf. F.J. Kahn; Appl. Phys. Lett., 18, 231, 1971).

(5) Circularly polarized light beam splitter utilizing circularly polarized light characteristics of the cholesteric phase (cf. S.D. Jacob; SPIE. 37, 98, 1981).
As mer,,tioned above, the liquid crystal composition of this invention comprises the optically active Y-lactone liquid crystalline compound, and due to a large spontaneous polarization arid chemical stability of said compound, shows a more rapid response speed and higher chemical stability than those of the conventional liquid crystal composition.
This invention is illustrated by the following Preparations, Examples and Comparati~~e Example, but should not be construed to be limited thereto.
In Examples, the positions of R and S in the optically active compounds (A) of this invention are shown by the position numbers in the following formula:

R1-O/ .~ *R2 G
(A) 1~0 The phase transfer temperature in Examples was measured by DSC (Differential Scanning Colorimetry) and a polarizing microscope. Besides, the symbols in the phase :l5 transfer temperature mean as follows:
C: Crystalline phase SmA: Smectic A phase SmC: Smectic C phase SmC*: Chiral smectic C phase ;0 Sml: Non-identified smectic phase other than SmA, SmC and SmC*.
N: Nematic phase N*: Chiral nematic phase I: Isotropic liquid ~!5 The chiral smectic C phase (SmC*) was further confirmed by measuring relative dielectric constant thereof.

[Preparation of phenol derivatives]
Preparation 1.
Preparation of 4-[5-(4-n-octyloxyphenyl)-2-pyrimidinyl]phenol:
i) Preparation of 4-benzyloxyphenylamidine hydro-chloride:
4-Cyar"ophenol (95.2 g), benzyl chloride (127 g) and potassium carbonate (138 g) were refluxed in acetone (160 ml) for 5 hours. The product was separated by filtration, concentrated under reduced pressure, and benzene was added thereto. The n~ixture~was washed with water, and benzene was distilled off L,nder reduced pressure to give 4-benzyloxy-benzonitrile (1.41.38 g). The 4-benzyloxybenzonitrile (141 g) was dissolved in benzene (338 ml), ethanol (270 ml), was added thereto, and the mixture wa:~cooled to 0°C. Into the resulting ~;lurry was bubbled hydrogen chloride gas (36 liters) with stirring, and thereafter, the temperature was raised to 25°C, and the mixture allowed to stand for 2 days. The reaction mixture was concentrated under reduced pressure until 1/3 volume, and to the concentrated mixture ether was added. The precipitated crystals were separated by suction filtration tc> give an imide ester (183 g).
The above-of>tained imide ester ( 183 g ) was mixed with ethanol (~!70 ml) to give a slurry, and thereto ~wasadded a solution of ammonia (60.75 g) in ethanol (405 ml). After allowing the mixture t:o stand at rocm temperature for 2 days, the solvent;aas distilled off under reduced pressure to give 4-benzyloxyphenylamidine hydrochloride (164.5 g).
NMR (DMSO-d6) 6: 5.19 (2H, s), 7.17 (2H, d, J=9.0 Hz), 7.35 (5H, s), 7.86 (2H, d) ii) Preparation of diethyl 4-n-octyloxyphenyl-malonate:
4-Hydroxyphenylacetic acid (50.0 g)was dissolved in ethanol (400 ml) and conc. sulfuric acid (0.5 ml) was added thereto. The mixture was refluxed with stirring, and ethanolwas distilled off to give eth~tl 4-hydroxyphenyl-acetate (60 g).
The ethyl 4-hydroxyphenylacetate (59 g) and sodium ethoxide (22.4 g)~~rere dissolved in ei:hanol (150 ml) and n-oct~Zl bromide (63.5 g) was added thE:reto. The mixture was refluxed for 3 hours and concentrated under reduced pressure. Ethyl acetate was added thereto to dissolve the oily substance. The mixture was washE~d with water, dried over anhydrous magneisum sulfate, distilled under reduced pressure to remove ethyl acetate, and further distilled :20 under reduced pressure to give ethyl 4-n-octyloxyphenyl-acetate (79.6 g, b.p. 179°C/0.1 mmHg).
The obtained ethyl 4-n-octy:Loxyphenylacetate (79 g), ethanol (140 ml), diethyl carbonate (300 ml) and sodium ethoxide (19.3 g)were mixed, and the mixture washeated with 'S stirring while ethanolwas distilled off. The reaction mixture wastransferred into ice water and acidified with hydrochloric acid. The organic layer wasseparated and the 13~ 1098 solvent distilled off to give diethyl 4-n-octyloxyphenyl-malonate (91.6 g).
NMR (CDC13) 6: 0.5-2.0 (21H, m), 3.90 (2H, t, J=6.0 Hz), 4.16 (4H, q, J=-7.2 Ha:), 4.52 (1H, s), 6.80 (2H, d, J=9.0 Hz), 7.26 (2H, d, J=~~.0 Hz) iii) Preparation of 4-[5-(4-n-octyloxyphenyl)-2-pyrimidinyl]phenol:
4-Ben~:yloxyphenylamidine hydrochloride (65.6 g) and diethyl 4-n-oct:yloxyphenylmalonate (91.0 g)were dissolved in methanol (500 ml) and sodium methox_Lde (44.8 g) was added thereto, The mixture was refluxed with stirring for 9 hours. After c:oolinc~, the reaction mixture was acidified with sulfuric acid, and the precipitated crystals were separated by suction filtration to give yellow crystals J.5 (77.7 g).
The above yellow crystals (77 g), phosphorus oxy-chloride (310 ml) and N,N-diethylaniline (46.5 ml)were mixed and refluxed with stirring for 26 hours. The excess phosphorus oxyc;hloride wasdistilled off under reduced ~:0 pressure, and t:he residue was transferred into ice-water and extracted with ether,. The extractwaswashed with water and distilled to remove ether to give a crude product (70 g).
The product way recrystallized from ether to give a compound (21 g) of the following formula:
25 n-C8H7_7C~~~~N\~ OCH2Ph (Ph: phenyl) NMR (CDC13) d: 0.4-2.:L (15H, m), 3.9!~ (2H, t, J=6.0 Hz), 5.09 (2H, s), 6"7-7.5 (11H, m), 8.38 (2H, d, J=9.0 Hz) The co:Lorless crystals obtained above (19.8 g), ethanol (757 ml;~, magnesium oxide (1:L.4 g), water (57 ml) and 10 % Pd-C (~~ g)were heated with stirring at 60°C under hydrogen atmosphere until a theoretical amount of hydrogen was absorbed. The reaction mixture wasfiltered with suction, and the filtratf~ was concentrated to give the desired 4-[5-(4-n-octyloxyphE~nyl)-2-pyrimidinyl]phenol (7.7 g) of the following formu:La:
N
n_C8H1,~C~~N / ~ pH
m.p. 137°C
NMR (CDC13) d: 0.5-2.1 (15H, m), 4.00 (2H, t, J=6.0 Hz), 6.92 (2H, d, J=!3.0 Hz), 7.01 (2H, d, J=9.0 Hz), 7.50 (2H, d, J=9.0 Hz), 8.30 (2H, d, J=9.0 Hz), 8.94 (2H, S) [Preparation of the compounds (B)]:
The starting optically active epichlorohydrins were prepared by the: processes as disclosed in U.S. Patent 4,840,907 and in Japanese Patent First Publication (Kokai) No. 230,567/1989 (published on September 14, 1989). These were R--(-)- and S-(+)-epichlorohydrins which have a chemical purity of 98.5 % or more (measured by gas chromatographic analysis) and an optical purity of 99 % or more: [the specific rotation, [a]D5 - -34.0°, +34.0°, c = 1.2, methanol, respectively].

~3~~o9e Preparation 2 To a suspension of 4-(4-n-octylphenyl)phenol (2.82 g) in 1, 2-dich_Loroethane ( 40 ml ) was added a 2M borone trichloride - :L,2-dic:hloroethane solution (6 ml) under ice cooling, and meahyl t:hiocyanate (O.s32 ml) and aluminum chloride (1.33 g) were added thereto. The mixture was stirred at roorn temperature untilthE~ aluminum chloride dissolved, and further stirred at 80°C for 3 hours.
After cooling, 4N aqueous sodium hydroxide solution (33 ml) :LO was added to thE: reaction mixture, and the mixture was stirred at 75 - 80°C for 30 minutes. After cooling, the reaction mixture waswashed with methylene chloride, and the aqueous layer was adjusted to pH 2 with 6N hydrochloric acid and then extracted with ether.. The extract w;~s dried and then ether :L5 was distilled oi:f under reduced pressure. The crude crystal thus obtained waspurified by silica gel column chromato-graphy to give 4-(4-n-octylphenyl)-2-cyanophenol (2.03 g) of the following i:ormula:
CN
n-CBH:.7 ~ \ / \ pH
a.0 m.p. 93°C
1H-NMR (CDC13) d: 0.88 (3H, t, J=6.8 Hz), 1.27-1.32 (lOH, m), 1.60-1.71 I;2H, m), 2.64 (2H, t, J=7.7 Hz), 6.24 (1H, broad s), 7.02--7.70 (7H, m) 25 IR (KBr): 3288 cm 1 (v~-H), 2240 cm 1 (vC=N) Preparation 3.
The above R-(-)-epichlorohydrin (4.25 g), the starting phenol derivative (2.50 g) of the following formula:
n C8H17 ~ \,~/~OH
and benzyltriethylammonium chloride (20 mg)were dissolved in dimethylformamide (3 ml) and thereto was added dropwise 24 wt.% aqueous sodium hydroxide (1.2 equivalent) at 60°C.
After reacting at the same temperature for 40 minutes, the reaction mixture wascooled to room temperature and extracted with ether. The extract was distilled under reduced pressure to remove the solvent. The residue was purified by silica gel chromatography to give S isomer ~~f a glycidyl ether (1.62 g) of the following formula:
n-C8H17 ~~''% \ 0 ., m.p. 90°C
[a]D5= +4.44° (c = 1.01, CH2C12) NMR (CDC13) 6: 0.50-3.00 (19H, m), 3.10-3.50 (1H, m), 3.80-4.30 (2H, m), 6.75-7.60 (8H, m) Preparation 4, The starting phenol derivative (13 g) of the following formula:
n-C6H13 / \ ~ / \ -OH
and the same R-(-)-epichlorohydrin (13.2 g) as used in -3~- ~3~r1098 Preparation 3, potas~~ium t-butoxide (8.8 g) and t-butyl alcohol (80 ml;~-,aere mixed and stirred at 60°C for 2 hours.
After the reaction mixture was concentrated, chloroform was added to the cone:entrate~ and the resultant= product was washed with a saturated saline solution and dried over anhydrous magnesium sulfate. Chloroform was distilled away under reduced pressure to give a crude product. The crude product was purified by si7.ica gel column chromatography to give S
isomer of a glycidyl ether (14.2 g) of the following formula:
n-C6H7.3 /
H C
m.p. 90°C
[aJDO= +4.78° I;c = 1.082, CH2C12) NMR (CDC13) d: 0.88-=!.0 (15H, m), 3.10-3.50 (1H, m), 3.80-4.40(2H, m), 6,.85-7.fi0 (8H, m) Preparation 5 The procedures of Preparation 4 were repeated except that the starting phenol derivative of the following formula:

n_C12E~25~\ / ~ pH
J
was employed an<i the above S-(+)-epichlorohydrin was employed in place of R-i;-)-epichlorohydrin to give R isomer of a glycidyl ether of the' following formula:
n C12Fi25~ J /
H CI

13~r 1098 m.p. 91°C
[a]D5= -3.59° (c = 1.07, CH2C12) NMR (CDC13) b: 0.85-2.93 (27H, m), 3.34-3.40 (1H, m), 3.97-4.27 (2H, m), 6.94-7.53 (SH, m) Preparation 6 The starting phenol derivative (10.0 g) of the following formula:
n-C8H170~~ ~ ~ OH
.LO and the same R-(-)-epichlorohydrin (18.6 g) as used in Preparation 3, piperidine (367 ml) and dimethylformamide (1 ml) were mixed and stirred at 60°C f or 10 hours. The reaction mixture wasdistilled under reduced pressure to remove the soljTent, acetone (5 ml) was added thereto and 7.5 further 24 wt.'o aqueous sodium hydroxide (1.2 equivalent)~;~ras added dropwise~. with stirring at room temperature . The mixture was reacted for 30 minutes. The reaction mixture was adjusted to pH 7 with 2N hydrochloric acid and extracted with ethyl acetate. The extract was dried over anhydrous 20 magnesium sulfate and. distilled under reduced pressure to remove the solvent. The residue was purified by silica gel chromatography to give S isomer of a glycidyl ether (1.58 g) of the following formula:
2;5 n C8H170~/ /

m.p. 131°C
[a]D7= +3.03° (c = 0.55, CH2C12) NMR (CDC13) d: 0.70-2.20 (17H, m), 2.55-3.00 (2H, m), 3.15-3.45 (1H, m), 3.75-4.20 (2H, m), 6.89 (2H, d, J=9.0 Hz), 6.92 {2H, d, J=8.4 Hz), 7.43 (4H, d, J=9.0 Hz) Preparation 7 A mixture of the starting phenol derivative (10 g) of the following formula:
N
n-C8H170~ ~ ~ ~ OH, N
the same R-(-)-epichlorohydrin (16.07 g) as used in Preparation 3, 20 wt.a aqueous sodium hydroxide (7.33 g) and dimethylformamide (20~ ml)was heated with stirring at 60-70°C
for one hour. The reaction mixture was cooled and water was added thereto. The mixture was extracted with dichloromethane to obtain a crude product (11.67 g). The crude product was Purified by silica gel column chromatography to give S
isomer of a glycidyl ether (9.07 g) of the following formula:
n-C H 0 ~ r'~ ~ ~ 0 8 1.7 ~ ri>~

m.p. 74°C
(~]D4= +1.66° (c = 1.02, CH2C12) NMR (CDC13) d: 0.5-2.2 (15H, m), 2.6-3.0 (2H, m), 3.1-3.7 (1H, m), 3.8-4.4 (4H, m), 6.95 (2H, d, J=9.0 Hz), 8.26 (2H, d, J=9.0 Hz), FI.36 (2H, s) Pr- epanation 8 A mixture of: the starting phenol derivative (7.44 g) of the following formula:

n C8H7.70~\ /-N~~OH
N
as prepared in Preparation 1, the same R-(-)-epichlorohydrin (9.16 g) as used in F>reparation 3, 50 wt.~ aqueous sodium hydroxide (1.71 g) and dimethylformamide (77 ml)was stirred at 60-70°C for 3 hour's. The reaction mixture was cooled and water was added thereto. The mixture was extracted with dichloromethane. The' extracted product was purified by silica gel column chromatography to give S isomer of a glycidyl ether (6.90 g) of the following formula:
N
n-C H,, O-\ ~~~ ~ ~ ~ 0 8 ._7 N~ H /'?~
m.p. 198°C
[a]D5= +0.95° ~;c = 1..04, CH2C12) NMR (CDC13) b: 0.6-2..1 (15H, m), 2.6-3.0 (2H, m), 3.2-3.5 (1H, m), 3.8-4..5 (2H,, m), 6.99 (4H, d, J=9.0 Hz), 7.50 (2H, d, J=9 . 0 Hz ) , f3 . 40 ( 2 H, d, J=9 . 0 Hz ) , 8 . 90 ( 2H, s ) Preparation 9 The si:arting phenol derivative (1.01 g) of the following formula:
n C8H:L7~N\~ / \ OH' N~
the same R-(-)~-epich:Lorohydrin (2.01. g) as used in Preparation 3 and benzyltriethylammonium chloride (16 mg) were mixed and heated at 70°C, and 24 wt.~ aqueous sodium hydroxide (650 mg) was dropwise added thereto. The mixture was stirred at 70°C for 2 hours. The reaction mixture was left to cool to room temperature and extracted three times with chloroform. The extractwas dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was recrystallized from hexane to give S isomer of a glycidyl ether (380 mg) of the following formula:
n_C8H1,~ ~~ / ~\ -p~~7 H b m.p. 65°C
[a]D5= +1.90° (c = 0.46, CH2C12) NMR (CDC13) s: 0.6-3.0 (19H, m), 3.2-3.6 (1H, m), 3.9-4.5 (2H, m), 6.99 (2H, d, J=9.0 Hz), 8.36 (2H, d, J=9.0 Hz), 8.55 (2H, s) Preparation 10 A mixture of the starting phenol derivative (3.12 g) of the following formula:
N
n C10H21~ ~' / ~ OH, N
the same R-(-)-epichlorohydrin (4.627 g) as used in ;z0 Preparation 3, 50 wt.o aqueous sodiunn hydroxide (0.88 g) and dimethylformamide (30 ml) was heated ~~uith stirring at 60°C
for 2.5 hours. The reaction mixture was cooled and distilled under reduced pressure to remove the solvent. The product was purified by silica gel column chr~~matography to give S
isomer of a glycidyl ether (2.96 g) ~af the following formula:

_ ' N \ /
n C10H21~~N/~ C ~°c.~
H Q
m.p. 65°C
[a]D7= +2.47° (c = 1.02, CH2C12) NMR (CDC13) &: 0.6-2.0 (19H, m), 2.4-3.0 (4H, m), 3.2-3.5 (1H, m), 3.8-4.5 (2H, m), 6.98 (2H, d, J=9.0 Hz), 8.33 (2H, d, J=9.0 Hz), 8.53 (2H, s) [Preparation of Compound (A)]
Preparation 11 To a solution of 4-(4-n-oct:~lphenyl)-2-cyanophenol (1.9 g) prepared in Preparation 2 in t-butyl alcohol (40 ml) was added potassium t-butoxide (832 mg). After a short period of time, R-(-)-epichlorohydrin (2.5 ml) and 4-(N,N-dimethylamino)pyridine (100 mg) were added to the mixture, 7.5 and the mixture wasstirred at room temperature for 2 days.
The reaction mixture was concentrated under reduced pressure, and to the residue wa:; added water . 'rhe mixture was extracted with ether, the extract dried and distilled to remove ether. The crude product thus obtained waspurified by 2p silica gel column chromatography to give S isomer of a glycidyl ether (750 mg) of the following formula:
CN
n C8H17 / ~ ~ / ~ C~7 m.p. 54°C
2.5 [a]D3= +7.88° (c = 1.01, CH2C12) NMR (CDC13) d: 0.88 (3H, t, J=6.6 Hz), 1.20-1.42 (lOH, m), 1.55-1.67 (2H, m), 2..64 (2H, t, J=7.7 Hz), 2.84-2.97 (2H, m), 3.39-3.43 (1H, m), 4.12-4.45 (2H, m), 7.05-7.77) (7H, m) IR (KBr): 2224 cm 1 ~(vC=N) Prepay=ation 12 The S isomer of glycidyl ether prepared in Preparation 3 (370 mg), diethyl n-propylmalonate (442 mg), potassium t-bui=oxide (134 mg) and t-butyl alcohol (3 ml) were mixed, and the mixturewas refluxed with stirring for 10 hours. The re<~ction mixture was cooled to room temperature and thereto was added dropwise 4N hydrochloric acid until pH
1. The mixture waswashed with water' and methanol to give white crystals. The product was separated and purified by silica gel column chromatography to give Y-lactone derivatives, (2S, 4S) isomer (240 md) and (2R, 4S) isomer (140 mg) of the following formulae:
(2S, 4S) isomer:
n-C H / \~ ~/ \ p ~ C3H7-n 8 .17 ~%~ H
H C--Phase transfer temperature:
C ~ I
_~15°C
(a]D6= +32.67° (c = 1.081, CH2C12) NMR (CDC13) d: 0.70-3.00 (27H, m), 1.00-4.25 (2H, m), 4.40-4.85 (1H, m), 6.60-7.60 (8H, m) IR (KBr): 1762 cm 1 (2R~ 4S) isomer:
n-C H / ~~ / \ C ~ ,/C3H7-n 8 17~~
H b-Phase transfer temperature:
C ~I
117°C
[a]D6= +22.50° (c = 0.504, CH2C12) NMR (CDC13) 5: 0.70-3.00 (27H, m), 4.00-4.25 (2H, m), 4.50-5.00 (1H, m), 6.60-7.60 (8H, m) IR (KBr): 1762 cm 1 Pre aration 13 The S isomer of glycidyl ether prepared in Prepara-tion 4 (365 mg), dimethyl malonate (232 mg), potassium t-butoxide (138 mg) and t-butyl alcohol (2 ml) were mixed, and the mixture wasrefluxed with stirring for 2 hours. The reaction mixture wascooled to room temperature and 4N hydro-chloric acid was added dropwise thereto to pH 1. The mixture was extracted three times with chloroform, and the 1.~ extractwas washed with a saturated saline solution, dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue waspurified by silica gel column chromatography to give 4S isomer of a 2-(methoxycarbonyl)-Y-lactone derivative (226 mg) of the 2~~ following formula:
/ \ / ~ 0 02CH3 n C6H13 IR (KBr): 1740, 1768 cm 1 The above Y-lactone derivative (200 mg), magnesium 2'> chloride (232 m.g), dimethylacetamide (1.5 ml) and water (0.5 ml) were mixed and the mixture was refluxed with stirring for 134 10~J8 hours. The reaction mixture was cooled to room tempera-ture and extracted twice with chloroform. The extract was washed with a saturated saline solution, dried over anhydrous magnesium sulfate and distilled under reduced 5 pressure to remove the solvent. The residue was purified by silica gel column chromatography to give 4S isomer of a Y-lactone derivative (145 mg) of the following formula:
n_C6H13 H
O
Phase transfer temperature:
C -~ I
138°C
[a]DO= +19.16° (c = 1.03, CH2C12) NMR (CDC13) d: 0.80-1.75 (11H, m), 2.15-2.85 (6H, m), 4.05-4.30 (2H, m), 4.75-4.95 (1H, m), 6.85-7.60 (8H, m) IR (KBr): 1764 cm 1 Preparation 14 The procedures of Preparation 12 were repeated except that the R isomer of glycidyl ether as prepared in Preparation 5w<is employed as the optically active glycidyl ether and dimethyl n-~butylmalonate wasemployed in place of diethyl n-propylmalon.ate to give Y-lactone derivatives, (2R, 4R) isomer and (2S, 2R) isomer of the following formulae:
(2R, 4R) isomer:
1 , C4H9-n n_C12~r25~/ / ~ 0 ,. ., -, H 0- ~~H
2s Phase transfer temperature:
C -~ I
130"C

[a]D = -28.56° (c = 1.06, CH2C12) NMR (CDC13) d: 0.85-2.69 (37H, m), 4.15-4.18 (2H, m), 4.71-4.77 (1H, m), 6.95-7.53 (8H, m) IR (KBr): 1764 cm 1 (2S, 4R) isomer:
~~ / ~ YC4H9-n n C12H25~~0 ,.:
0_--~ H

Phase transfer temperature:
C --~ I
128"C
[a]D4= -22.98° (c = 1.07, CH2C12) NMR (CDC13) d: 0.85-2.85 (37H, m), 4.08-4.21 (2H, m), 4.81-4.86 (1H, m), 6.93-7.52 (8H, m) IR (KBr): 1760 cm 1 Pr_ eparation 15 The S isomer of glycidyl ether prepared in Preparation 6 (260 mg), dimethyl n-o~~tylmalonate (269 mg), potassium t-butoxide (90 mg) and t-butyl alcohol (2 ml) were mixed, and the mixture was refluxed with stirring for 13 hours. After the reaction, the reaction mixture was treated in the same manner as described in Preparation 12 to give white crystals. The product was separated and purified by silica gel column chromatography to ~~ive a Y-lactone derivative, (2S, 4S) isomer (43 mg) ~~f the following formula:

93~ 1098 n-C H 0 /~\N~~~-0~ ~~~ C8H17-n 8 17 ~/
H (5----y0 H
Phase transfer temperature:
C ~ I
139°C
[a]DO= +28.59° (c = 0.674, CH2C12) NMR (CDC13) 8: 0.70-2:.95 (37H, m), 3.80-4.20 (4H, m), 4.45-4.90 (1H, m), E~.90 (4H, d, J=9.0 Hz), 7.42 (4H, d, J=9.0 Hz) IR (KBr): 1760 cm 1 Preparation 16 The S isomer of glycidyl ether prepared in Preparation 8 (518 mc~), dimethyl p-pentylmalonate (970 mg) and potassium t:-buto~:ide ( 269 mg ) were dissolved in dimethyl-formamide (5 ml.) and t-butyl alcohol (5 ml) and the mixture was heated with stirring at 90°C for 5 hours. After the reaction, the reaction mixture was treated in the same manner as described in Preparation 12 to give a Y-lactone derivative of t:he fo:Llowing formula. The obtained compound was a mixture o1. diastereccners, from which the ( 2R, 4S ) isomer is separated b~~ silica gel column chromatography.
( 2R, 4S) isome:_ n-C8H:170 / \~ / N~ / \ O '~~, C5H11-n ~J ~ N
H O
U
Phase transfer temperature:
138°C 145''C 201"C 202°C
C ~ Sml ~~ SmC* ~~ N* ~ I
134°C 145'°C 201"C 202°C

NMR (CDC13) d: 0.4-3.0 (29H, m), 3.7-4.3 (4H, m), 4.82 (1H, m), 7.00 (4H, d, J=9.0 Hz), 7.50 (2H, d, J=9.0 Hz), 8.39 (2H, d, J=9.0 Hz), 8.85 (2H, s) IR (Nujol*) : 1778 cm 1 Preparation 17 The S isomer of glycidyl ether prepared in Preparation 9 (320 mg), dimethyl n-hexylmalonate (406 mg) and potassium t-butoxide (116 mg) we~_e dissolved in t-butyl alcohol (3.5 ml), and the mixture wa:~refluxed with stirring for 6 hours. After the reaction, the reaction mixture was treated in the same manner as described in Preparation 12 to give a mixture of diastereomers of a Y-lactone derivative (270 mg, (2S, 4S)/(2R, 4S) - 9/1).
(2S, 4S) isomer:
/ N~~ ~ ~ ~~ 6H13-n n-C8H17~ /
'-N H p --~0 H
(2R, 4S) isomer:
/ N~, / ~ ~~~~ ,, C6H13-n n_C8H17~N/~0 ~ ~,'~i H ~ 0 Physical properties of the mixture:
Phase transfer temperature:
C ---~ I
116°C
[a)D5= +37.93° (c = 1.024, CH2C12) NMR (CDC13) d: 0.50-2.80 (33H, m), 4.10-4.25 (2H, m), 4.45-4.85 (1H, m), 6.95 (2H, d, J=9.0 Hz), 8.34 (2H, d, J=9.0 Hz), 8.52 (2H, s) IR (Nujol) ~ 1778 cm-1 *Trade mark Prepac~ation 18 In they same manner as described in Preparation 17 except that they S isomer of glycidyl ether prepared in Preparation 10 was used as the optically active glycidyl ether and dimet.hyl n--dodecylmalonate Was used in place of dimethyl n-butylmalonate, therewere prepared Y-lactone derivatives, (1S, 4S) isomer and (2R, 4S) isomer.
(2S, 4S) isomer:
n_C10~:~21 / /~ / \ C
~rl\ ~ ,~~ ~C12H25-n H ~---~b H
Phase transfer temperature:
C ~ I
127°C
[a]D1= +26.01° (c = 1..062, CH2C12) NMR (CDC13) d: 0.5-2.9 (49H, m), 4.19 (2H, m), 4.82 (1H, m), 6.95 (2H, d, J=~9.0 Hz;), 8.32 (2H, d, J=9.0 Hz), 8.52 (2H, s) IR (Nujol): 1778 cm 1.~ (2R, 4S) isomer: , r1 ~ ~C12H25-n n-C10~~21~ ~ / \ _p DI H C_ 'H
b Phase transfer temperature:
C -~ I
89°C
2() (a]D1= +17.12° (c = C1.398, CH2C12) NMR (CDC13) 6: 0.5-2.9 (49H, m), 4.19 (2H, m), 4.81 (1H, m), 6.95 (2H, d, J=~9.0 H2;), 8.32 (2H, d, J=9.0 Hz), 8.52 (2H, s) IR (Nujol) : 17 7 8 cm 1-Preparation 19 2y The S isomer of glycidyl ether prepared in Preparation 8 (518 mg), dimethyl n-undecylmalonate (1.37 g) and potassium t-butoxide (269 mg)werE: dissolved in dimethyl-formamide (5 ml) and t-butyl alcohol (5 ml) and the mixture was heated with stirring at 90°C for 3 hours. After the reaction, the reaction mixture was treated in the same manner as described in Preparation 12 to give a Y-lactone derivative of the following formula (733 mg). The obtained compound was a mixture of diastere~ners, from which the (2S, 4S) isomer and (2R, 4S) isomer were separated by silica gel column chromatography.
(2S, 4S) isomer:
n-C H 0 / \~ ~~ / \ O~'/~ ~11H23-n 8 17 ~ ~ N -~ - ~H
;3 O--~0 Phase transfer temperature:
150°C 155°C 183°C
C ~ Sml ~ SmC* ~ I
t c 147°C 155°C 180°C
[aJDl+20.93° (c = 1.116, CHC13) NMR (CDC13) d: 0.4-3.0 (41H, m), 3.7-4.3 (4H, m), 4.71 {1H, m), 7.00 (4H, d, J=9.0 Hz), 7.50 (2H, d, J=9.0 Hz), 8.39 (2H, d, J=9.0 Hz), 8.89 (2H, s) IR (Nujol) : 1778 cm 1 (2R, 4S) isomer:
n-C H 0 ~ '~ / N~~ / \~_0~ ; C11H23-n 8 17 ~~~N~ °'~~H

O
Phase transfer temperature:
2y 120°C 133°C 195°C
C ~ Sml ~ SmC* ~ I
114°C 131°C 192°C

NMR (CDC13) s: 0.4-3.0 (41H, m), 3.7-4.3 (4H, m), 4.83 (1H, m), 7.00 (4H, d, J=9.0 Hz), 7.50 (2H, d, J=9.0 Hz), 8.39 (2H, d, J=9.0 Hz), 8.89 (2H, s) IR (Nujol) : 1778 cm 1 Preparation 20 The S isomer of glycidyl et:ner prepared in Prepara-tion 7 (1.00 g), dimethyl methylmalo:nate (677 mg) and potassium t-butoxide (630 mg) were dissolved in dimethylform-amide (10 ml) and t-butyl alcohol (10 ml) and the mixture was heated with stirring at 90°C for 2 hours. After the reaction, the reaction mixture was treated in the same manner as described in Preparation 12 to give a Y-lactone derivative of the following formula (810 mg). The obtained compound was a mixture of d_iasterecaner~:, from which the ( 2S, 4Sj isomer and (2R, 4S) isomer were separated by silica gel column chromatography.
(2S, 4S) isomer:
n_C8H170 / Nv ~ ~ iI' _ _ 'CH3 rl~ H
H 0-~0 Phase transfer temperature:
159°C
C ~ I:
NMR (CDC13) d: 0.5-3.0 (21H, m), 3.9-4.3 (4H, m), 4.65 (1H, m), 6.93 (2H, d, J=9.0 Hz), 8.25 (2H, d, J=9.0 Hz), 8.37 (2H, s) IR (Nujol) : 17E~0 cm 134 ~ogg (2R, 4S) isomer:
n-C$H170J~N~ / \ ~~/ ~~~-~H3 N H 0_ '0 Phase transfer temperature:
115°C
C ~ I
NMR (CDC13) d: 0.5-3.0 (21H, m), 3.9-4.3 (4H, m), 4.75 (1H, m), 6.93 (2H, d, J=9.0 Hz), 8.25 (2H, d, J=9.0 Hz), 8.37 (2H, s) IR (Nujol): 1780 cm 1 Preparation 21 A mixture of the S isomer of glycidyl ether (363 mg) obtained in Preparation 11, diethyl n-propylmalonate (303 mg), potassium t-butoxide (157 :mg) and t-butyl alcohol (10 ml) was refluxed with stirring for 6 hours. The reaction mixture was cooled to room temperature and water was added thE.reto.. The mixture was adjusted to pH 2 with 4N hydrochloric acid and extracted with chloroform. The extract was distilled and the resulting oily substance purified by silica gel column chromatography to give (2S, 4S) isomer (33 mg) and (2R, 4f.) isomer (25 mg) of a Y-lactone of the following formulae.
(2S, 4S) isomer:
/ \ ~CN~~ C3H7-n n C8H17 0 H
H 0 ---~
O
'S Phase transfer temperature:

8E.°C
C ~ I
[a]D3 - +31.83° (c = 1.09, CH2C12) NMR (CDC13) d: 0.88 (3H, t, J=6.6 Hz), 0.97 (3H, t, J=7.1 Hz), 1.25-1.32 (lOH, m), 1.41-1.58 (3H, m), 1.59-1.66 (2H, m), 1.85-2.07 (2H, m), 2.55-2.78 (4H, m), 4.31 (2H, d, J=4.3 Hz), 4.74-4.83 (1H, m), 7.00-7.77 (7H, m) IR (KBr): 2232 cm 1 (vC-N), 1768 cm 1 (vC=O) (2R, 4S) isomer:
CN ~y C H -n n-C H ~ \ ~ \ -O~%'~ 3 7 8 1. 7 O
Phase transfer temperature:
80°C
C ~ I
[a]D3 - +18.26° (c = 0.87, CH2C12) NMR (CDC13) d: 0.88 (3H, t, J=6.8 Hz), 0.98 (3H, t, J=7.1 Hz), 1.25-1.27 (12H, m), 1.45-1.56 (2H, m), 1.60-1.62 (1H, m), 1.85-1.95 (1H, m), 2.12-2.22 (1H, m), 2.56-2.67 (3H, m), 3~05-3.10 (1H, m), 4.19 (1H, dd, J=3.3, 10.3 Hz), 4.37 (1H, dd, J=3.3, 10... Hz), 4.84-4.89 (1H, m), 7.00-7.77 (7H, m) IR (KBr): 2232 cm 1 (vC=N), 1768 cm 1 (vC=O) [Liquid crystal. compositions containing the compound (A) and physical properties thereof]
Example 1 The (~!S, 4S) isomer of the Y-lactone derivative prepared in Preparati.an 12 of the following formula:

/;~~~ ~ 0~~~~C3H7-n n C8H1.7~
H p---~O H
and a compound of the' following formula (1):
Nv n C8H1.7~~n /_\ OC8H17-n ( 1 ) were mixed together at: a weight ratio of 1 . 15.6 to give a liquid crystal composition.
The obtained liquid crystal composition was subjected to a DSC measurement, observation with a polarization mi.croscc>pe and a measurement of the relative dielectric con~;tant by a bridge method wherein the liquid crystal composition was sealed in a cell made of glass (thickness of ;pacer: 22 um) and the cellwas charged with alternating current (70 Hz, 1 V). As a result, the composition was prove:nto have the following phase transfer temperature:
31°C 61.°C 65°C 68°C
C ~ ~ SmC* ~~ SmA ~~ N* ~ I
27°C 55°C 63°C 67°C
Fig. 1. show; the result of the measurement for the relative dielectric constant of the composition.
Itw~ proven that the above (2S, 4S) isomer of the Y-lactone derivative alone does not show the ferro-electricity but. shows the ferroelectricity when it is mixed with another liquid crystalline compound.

_ t, 8 _ Example 2 The (2R,. 4S) :isomer of the Y-lactone derivative prepared in Preparation 12 of the following formula:
\ C3H~-n n - C 8 H 1 ~ _ ~~ O/// aI
~ ~'H
H O
O
and the compound (1) used in Example 1 were mixed together at a weight ratio of. 1 . :18.0 to give a Liquid crystal composition.
The phase transfer temperature of the obtained composition was measured in the same m,~nner as described in Example 1. As a result=, the composition shows the following phase transfer tE:mperature.
31°C 63°C 64°C 68°C
C ~ SmC* - ~ SmA ~ N* ~ I
E; - E -26°C 53°C 63°C 66°C
Fig. 2 :shows i=he result of the measurement for the relative dielectric constant of the composition.
It was proven 1_hat the above ( 2R, 4S) isomer of the Y-lactone derivative alone does not show the ferro-electricity but shows the ferroelectricity when it is mixed with another liquid crystalline c~~mpound.
Example 3 The (4S; isomer of the Y-lactone derivative prepared in Preparation 13 of the fol.Lowing formula:
/~
n_C6H13_ /~/ \ O/

and a compound of the following formula (2):
~ N, n-C8H1~~- ~,-~/ \ -OC10H21 n ( 2 ) ~N
were mixed together at a weight ratio of 1 . 19 to give a liquid crystal composition.
The obtained liquid crystal composition was measured for the response speed. As a result., it wasfound that the composition showed a response speed as high as 490 usec (40°C). The response speed was measured in the following manner:
the above composition was sealed in a cell (thickness of spacer: 2 um) surface-treated with an aligning agent and change in strength of transmitted lic3ht was measured when the cell was charged with a voltage of Vp._p = 20 V with use of crossed nicols, wherein PET (polyethylene terephthalate) film as the spacer, polyimide film as the aligning agent and ITO (indium-tin oxide) electrode were employed and the rubbing was made in parallel direction.
Ex- ample 4 The (2R, 4R) isomer of the ~Y-lactone derivative prepared in Preparation 14 of the following formula:
~,,~~'', 4 9 n-C H / \\ / \ 0 C H -n 12 2 5 ~~~~ \ H
H O-O
and the compound of the formula (2) used in Example 3 were mixed together at a weight ratio of 1 . 19 to give a liquid crystal composition.

The obtained composition was measured for the response speed in the same manner as described in Example 3. The result;showed a response speed as high as 75 usec (40°C).
Exam le 5 The (2S, 4S) isomer of the r-lactone derivative prepared in Preparation 15 of the following formula:
n-C H 0 / ~~ / ~ C!~~ C8H17-n 8 17 ~~ ~ ~H

and the compound of the formula (1) used in Example 1 were mixed together at a weight ratio of 1 . 15.9 to prepare a liquid crystal composition. The phase transfer temperature of the obtained composition was measured in the same manner as described in. ExamF~le 1. As a result, it was shown that the composition. had the following phase transfer temperature:
31°C 58~°C 66°C 71°C
C ~ SmC* ~ SmA '~ N* I
-- ~ E_ 25°C 58°C 63°C 68°C
Fig~ ='~ showy; the result of the measurement for the relative dielectric constant of the composition.
It was found that the above r-lactone derivative alone does not show ferroelectricity but it shows ferroelectricit:y when it is mixed with another liquid crystalline compound.
Examp7.e 6 and Comparative Example 1 The (2S, 4S) isomer of the Y-lactone derivative 13~ 1098 prepared in Pre~paratian 15 of the following formula:
1 %~ ~ ~ ~C8H17-n n-C8H170~ ~,~-0 H ~---~,0 H
and the smectic liquid crystal components as shown in Table 1 were mixed together to prepare a liquid crystal composition.
The obtained liquid crystal composition was measured for the respon_=,e speed in the same manner as described in Example 3. As a result, it wasfound that the liquid crystal 7.0 composition comprising the Y-lactone derivative of this invention (Example 6) shows an extremely high response speed as compared to that of: the liquid crystal composition without the r-l.actone derivative (Comparative Example 1).

Table 1 ( wt o ) Liquid crystalline compound Ex. 6 Comp. Ex.
( li ' ~ ~ C8H17--n i ~n C8H170 i \ ~~pi ~i~ 10.0 - i I i w H
j H b ~ , i , n C8H17J~ N~~~~OC10H21 n , 18.2 i 20.2 .-N i i , O
~

17.1 19.0 i II ~
n C8H170~~C 0 \~OC5H11-n ~

I

' II ~ 14.8 16.4 i I, n C7H150 s~~:~ C O~\ \ OC5H11-n , ' ' ~n-C H O-~~ O-C l \ Ji~ \ -~~\'~*~\ ~ 20. 6 i 23. 0 j 8 17 U ~ ~ , N
n-C H ~ ~ ~ \~- */\ ~ 19.3 21.4 8 17~N>~~
Response speed (usec) 50 ~ 1800 I(56°C) ' (50°C) Example 7 The (2R, 4S) isomer of the ~r-lactone derivative prepared in Preparation 16 of the following formula:
n-C H 0 ~ '\~N~ r \ 0~~ C5H11-n 8 17 ~ ~
/ ~ N' '-=J ~, ~i la O
O
and the compound of the formula (1) used in Example 1 were mixed together at a weight ratio of 1 . 8.4 to prepare a liquid crystal composition.

The phase transfer temperature of the obtained composition was measured in the same manner as described in Example 1. As a result, it was shown that the composition had the following phase transfer temperature:
31°C 70°C 72°C 77°C
C ~ SmC* ~ SmA ~ N* ~ I
27°C 60°C 71°C 77°C
The above compound of the f~~rmula (1) had the following phase transfer temperature:
29°C 56°C 62°C 68°C
C E-j SmC ~-------~ SmA ~ ~ N ~~ I
Therefore, by mixing the above (2R, 4S) isomer of the Y-lactone derivative with other liquid crystalline compound showing no ferroelectricity, ferroelectricity was produced, and in addition, the obtained temperature range showing ferroelectricity wasmuch wider than that of the original SmC pr.ase.
The same measurement was conducted on the (2S, 4S) isomer of the Y-lactone derivative which was separated concurrently with the (2R, 4S) isomer of the Y-lactone derivative, and as a result, a similar effectwas shown.
Ex- ample 8 The diastere~ner mixture of the Y-lactone derivative prepared in Preparation 17 ((2S. 4S)/(2R, 4S) - 9/1) of the following formulae:
(2S, 4S) isomer:
n-C H / N~. / ~ 0!//~~~C6H13 n 8 i_7~N~~ H
H 0 -~~

(2R, 4S) isomer:
n-C H ~N\\~/~-0~~~ ~C6H13-n N H 0- , H
O
was mixed with the compound of the formula (1) used in Example 1 at a weight ratio of 1 . 9.7 to prepare a liquid crystal composition.
The phase transfer temperature of the obtained composition was measured in the same manner as described in Example 1. As a result, it is shown that the composition has the following phase transfer temperature:
24°C 58°C 64°C 67°C
C ~ ~ SmC * ~~ SmA ~ ~ N * ~'-'~ I
Fig. 9 shows. the result of the measurement for the relative dielectric canstant of the composition.
It was found that the above Y-lactone derivative alone does not show ferroelectricity but it shows ferroelectricit:y when mixed with another liquid crystalline compound.
- Exampl.e 9 The (~!S, 4S) isomer of the Y-lactone derivative prepared in Pre~parati.on 18 of the following formula:
r1~ C12H25-n n-C10~i21 / \ ~ ~ 0~/~
~~I~~~ H
H 0-y and the compound of t:he formula (2) used in Example 3 were mixed together at a weight ratio of 1 . 19 to prepare a liquid crystal composition.

The obtained composition wasmeasured for response speed in the same manner as described in Example 3, and as a result, it showed a response speed as high as 300 usec (40°C).
Exam les 10 and 11 Using the (2S, 4S) isomer of the Y-lactone derivative prepared in Preparation 19 of the following formula:
n C8H170~~~ \~ ~/ ~ 0~ C11H23-n N H O~b H
and the Y-lactone derivatives prepared in Preparation 20 as a mixture of (2S, 4S) isomer . (2R, 4S) isomer = 1 . 1 of the following formulae:
(2S, 4S) isomer:
, n-C H 0~~~~~ 0 ~ CH3 8 1. 7 1\I H ~ _~O H
(2R, 4S) isomer:
rl ~ ~CH3 n C8H1.70~ ~
r1~ ~ 'H
H b-b liquid crystal compos~itionsw~'e prepared comprising the components as ~~hown i.n Table 2.
The obtained compositions w,~e measured on the phase transfer temperature and the response speed in the same manner as described in Example 3.
When t:he Y-7_actone derivative of this invention was not contained ~_n the liquid crystal composition, the response speed was as slow as usec (50C) as shown in Comparative Example 1.
On the contrary, the liquid crystal composition comprising the Y-lactone derivative of this invention shows a much Faster response speed, which proves that the liquid crystal composition of this invention is extremely useful as an element for display devices or an element for opto-electronics devices.

Table (wt o) Liquid crystalline compound ~Ex. 10 Ex. 11 j ~Y-Lactone 11.6 deriv. ~ -(2S, I
4S) isomer (Prep.
19) ~

Y-Lactone 4.9 i deriv. i (2S, 4S) isomer (Prep.
20) i, -~

"
(2R, 4S) "
'~
;
-I
4.9 n C8H17-~
>-~
~-OC10H21 n j 17.8 ~
18.2 -N
-i i O

II
16.8 ~
17.1 H
-n ~OC
0-C>
C
O
n'C
H

~

g p '~
' I
i II
14.5 14.8 /
\
/'~C-~~
/
\
OC
H
-n n C
H

i O

p *
\
i 20.4 ( 20.8 /
~
/
\

~~O
O-.C
~
~n-C8H170 .~l ' I I
-N
~
*
I
~
v /
~

18.9 19.3 O
n-C
H

C

'N

Temperature 28-68 range (SmC*
phase)(C) Response I
speed (asec) ~(60C) (30C) Example 12 The (2S, 4S) isomer of the optically active Y-lactone derivative prepared in Preparation 21 and a compound of the formula:
N
n C9g19~~> / ~ -OC8H17 ( 3 ) were mixed together at a weight ratio of 1 . 19 to prepare a liquid crystal composition.
By measuring in the same manner as described in Example 1, the liquid crystal composition thus obtained had the following phase transfer temperature:
30°C 57°C 72°C
C ~ SmC * -'~ SmA - ~ I
22°C 56°C 71°C
It was prove:nthat the above (2S, 4S) isomer of the optically active Y-lactone derivative alone does not show ferroelectricity but shows ferroelectricity when mixed with another liquid crystalline compound.
The above composition was measured for the response speed in the same manner as described in Example 3, and as a result, it showed a response speed ,as high as 128 usec (40°C).
Example 13 The (2R, 4S) isomer of the optically active Y-lactone derivative prepared in Preparation 21 and the 25 compound of the formula (3) used in Example l2were mixed at a weight ratio of 1 . 19 to prepare a liquid crystal compo-sition.
By measuring in the same manner as described in Example 1, the liquid. crystal composition thus obtained had the following phase transfer temper;~ture:
30.7°f. 55.3°C 71.2°C
C ~' SmC * -~ SmA --"~ I
X22°C ~ 53.8°C ~ 70.4°C
Itwas proven that the above (2R, 4S) isomer of the optically active Y-lactone derivative alone does not showferroelectricity but shows ferroelectricity when mixed with another liquid crystalline compound.
The above composition wasmeasured for the response speed in the same manner as described in Example 3, and as a result, it showed a response speed as high as 98 usec (40°C).

Claims (4)

1. A liquid crystal composition which comprises at least one liquid crystalline compound having an optically active .gamma.-lactose ring of the formula (A):
wherein R1 is a group selected from the group consisting of wherein n and e are each independently 0 or 1; R3 is an alkyl group having 1 to 15 carbon atoms; X and Y are each independently a group selected from the group consisting of a hydrogen atom, a halogen atom anal a cyano group; R2 is a group of the formula: -(CO)m -R4; m is 0 or 1; R4 is a hydrogen atom or an alkyl group having 1 to 15 carbon atoms;
and the symbol * is an asymmetric carbon atom, and a chiral or non-chiral liquid crystal compound of the formula (J) wherein E, F and G are each independently a 6-membered ring selected from the group consisting of or these 6-membered rings having a substituent selected from the group consisting of a halogen atom, a cyano group, or a nitro group; a and b are each 0, 1 or 2, and c is 1 or 2, but a+b+c - 2 to 4; W
and M are each a single bond or a group selected from the group consisting of -O-, -S-, -CH2O-, and -OCH2-; K and L are each independently a single bond or a group selected from the group consisting of , -CH2O-, -OCH2-, -CH2-CH2-, -CH=N-, -N=CH-, -CH=CH-, -C=C-, and , provided that K is a single bond when a = 0, and L is a single bond when b - 0; R' and R" are each independently an alkyl group having 1 to 15 carbon atoms which may contain one or more asymmetric carbon atoms.

2. The composition according to claim 1, wherein the chiral or non-chiral liquid crystal to be mixed with the comnpound of the formula (A) is at least one of th members selected from the group consisting of a compound of the formula (J-1) wherein R "' and R"" are the same or different and are each a straight chain or branched chain alkyl group having 1 to 15 carbon atoms or a straight chain or branched chain alkoxy group having 1 to 15 carbon atoms, wherein the alkyl and alkoxy groups may have one or more asymmetric carbon atoms, and a compound of the formula (J-2):
wherein R' " and R"" are each as defined above, A is or , and k and l are independently 0 or 1, but k + 1 ~ 2.

3. The composition according to claim 1, wherein the compound of the formula (A) is in the forth of a racemic mixture.

4. An element for opto-electronic devices comprising the liquid crystal composition as set forth in claim 1, 2 or 3.