Mitsubishi Gas Chemical Company, Inc.

Hiroshi Mineta

Tomoyuki Yui

Masahiro Johno

Yuki Motoyama

Takahiro Matsumoto

Maki Ito

Takakiyo Mine

Teruyo Tomiyama

Yoshihisa Arai

Masamichi Mizukami

Yoshihiro Gocho

Seiji Adachi

A fluorine-substituted compound of the following general formula (1) or (2), and a ferrielectric liquid crystal composition comprising the above compound and a specific ferrielectric liquid crystal compound,

Fluorine-substituted compounds and ferrielectric liquid-crystal composition containing the same

A process for the production of R-configuration or S-configuration optically active alcohol having the formula (1),

Process for the production of an optically active alcohol and a novel

A two-rings-containing phenyl ester compound of the following general formula (1), ##STR1## wherein R.sup.1 is a linear alkyl group having 5 to 12 carbon atoms, R.sup.2 is a linear alkyl group having 1 to 15 carbon atoms, X.sup.1 and X.sup.2 are both hydrogen atoms or one of X.sup.1 and X.sup.2 is a fluorine atom and the other is a hydrogen atom, Y.sup.1 and Y.sup.2 are both hydrogen atoms or one of Y.sup.1 and Y.sup.2 is a fluorine atom and the other is a hydrogen atom, and A.sup.1 is a hydrogen atom, --CH.sub.3 or --CF.sub.3, provided that when A.sup.1 is a hydrogen atom or --CH.sub.3, p is 0 and that when A.sup.1 is --CF.sub.3, p is 1 and q is an integer of 5 to 8, and an anti-ferroelectric liquid crystal composition containing at least one of two-rings-containing phenyl ester compounds of the above general formula (1) in claim 1 and either an anti-ferroelectric liquid crystal compound or a mixture of anti-ferroelectric liquid crystal compounds.

Two-rings-containing phenyl ester compound and anti-perroelectric liquid

A liquid crystal compound represented by the following general formula (1): ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms, X and Y are both a hydrogen atom, or one of them is a hydrogen atom and the other is a fluorine atom, m is an integer of 0 to 5, n is an integer of 1 to 5, and C* is an asymmetric carbon atom. Since the liquid crystal compounds of the present invention have an anti-ferroelectric phase or a ferrielectric phase and the anti-ferroelectric phase or a ferrielectric phase has a highly practical phase sequence and wide temperature range, they are of great industrial value.

Liquid crystal compound

A racemic compound of the formula (1) ##STR1## and an anti-ferroelectric liquid crystal composition consisting essentially of said racemic compound and one anti-ferroelectric liquid crystal compound of the formula (2) or a mixture of two or more compounds selected from anti-ferroelectric liquid crystal compounds of the formula (2), ##STR2## said composition having excellent steepness of threshold, having an anti-ferroelectric phase over a broad temperature range and having the performance of a high response speed and a high contrast.

Racemic compound and anti-ferroelectric liquid crystal composition

A swallow-tail-shaped liquid crystal compound of the following general formula (1), ##STR1## wherein A is --O--, --COO-- or a single bond (--), m is an integer of 4 to 12, and n is an integer of 2 to 4. The above swallow-tail-shaped liquid crystal compound of the present invention is a novel achiral anti-ferroelectric liquid crystal and can be converted to an optically active anti-ferroelectric liquid crystal by mixing it with an optically active compound as a chiral dopant.

Swallow-tail-shaped liquid crystal compound

Novel anti-ferroelectric liquid crystal compounds of the formula (1), ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms, X is a hydrogen atom or a fluorine atom, n is an integer of 2 to 7, p is an integer of 0 to 2 and C* is an asymmetric carbon atom. The above anti-ferroelectric liquid crystal compounds have an anti-ferroelectric phase in a broad temperature range and have a low melting point, so that they can be advantageously used as a main component for a practically valuable liquid crystal material or as a component for a liquid crystal composition.

Anti-ferroelectric liquid crystal compounds

A racemic compound of the formula (1) ##STR1## and an anti-ferroelectric liquid crystal composition consisting essentially of said racemic compound and one anti-ferroelectric liquid crystal compound of the formula (2) or a mixture of two or more compounds selected from anti-ferroelectric liquid crystal compounds of the formula (2), ##STR2## said composition having excellent steepness of threshold, having an anti-ferroelectric phase in a broad temperature range and having the performance of a high response speed and a high contrast.

A process for the production of an intermediate for a liquid crystal compound, which comprises reacting an alkyloxybiphenylcarboxylic acid with purified thionyl chloride substantially free of sulfuryl chloride, the thionyl chloride being obtained by adding phenol, etc., to thionyl chloride, heating the mixture and distilling the resultant mixture; and a process for the production of a liquid crystal compound from the above intermediate. According to the present invention, thionyl chloride can be easily purified, and a liquid crystal compound having a very high purity can be obtained by the use of the purified thionyl chloride.

Process for the production of intermediate for liquid crystal compound

�I! An optically active compound of the formula (1), ##STR1## wherein R.sup.1 is a linear alkyl group, each of X.sup.1 and X.sup.2 is a hydrogen atom or one of X.sup.1 and X.sup.2 is a hydrogen atom and the other is a fluorine atom, each of Y.sup.1 and Y.sup.2 is a hydrogen atom or one of Y.sup.1 and Y.sup.2 is a hydrogen atom and the other is a fluorine atom, m is an integer of 3 to 10, and C* is an asymmetric carbon atom, �II! an anti-ferroelectric liquid crystal composition consisting essentially of the optically active compound of the above formula (1) and a compound of the formula (2), ##STR2## and �III! a ferrielectric liquid crystal composition consisting essentially of the optically active compound of the formula (1) and a compound of the formula (3). ##STR3##

Optically active compound, liquid crystal compositions containing the

A liquid crystal compound of the formula (1) ##STR1## wherein R is a linear alkyl group having 6 to 12 carbon atoms,

Liquid crystal compound having ferrielectric phase and liquid crystal

An anti-ferroelectric liquid crystal compound of the following general formula (1), and an anti-ferroelectric liquid crystal composition containing it, ##STR1## wherein R is a linear alkyl group, A is --O-- or --COO--, m is an integer of 5 or greater, n is an integer of 1 to 3, each of X and Y is independently a hydrogen atom or a fluorine atom, and C* is asymmetric carbon.

Anti-ferroelectric liquid crystal compound and anti-ferroelectric liquid

A two-rings-containing phenyl ester compound of the following general formula (1), ##STR1## wherein R.sup.1 is a linear alkyl group having 5 to 12 carbon atoms, R.sup.2 is a linear alkyl group having 1 to 15 carbon atoms, X.sup.1 and X.sup.2 are both hydrogen atoms or one of X.sup.1 and X.sup.2 is a fluorine atom and the other is a hydrogen atom, Y.sup.1 and Y.sup.2 are both hydrogen atoms or one of Y.sup.1 and Y.sup.2 is a fluorine atom and the other is a hydrogen atom, and A.sup.1 is a hydrogen atom, --CH.sub.3 or --CF.sub.3, provided that when A.sup.1 is a hydrogen atom or --CH.sub.3, p is 0 and that when A.sup.1 is --CF.sub.3, p is t and q is an integer of 5 to 8, and an anti-ferroelectric liquid crystal composition containing at least one of two-rings-containing phenyl ester compounds of the above general formula (1) in claim 1 and either an anti-ferroelectric liquid crystal compound or a mixture of anti-ferroelectric liquid crystal compounds.

Two-rings-containing phenyl ester compound and anti-ferroelectric liquid

An antiferroelectric liquid crystal substance represented by the following general formula (1) ##STR1## wherein R represents a straight-chain alkyl group of 6-10 carbon atoms; X represents ##STR2## when X is ##STR3## Y is any of CH.sub.3, CF.sub.3 and C.sub.2 H.sub.5, L is 0 or an integer of 5 to 8, m is 0 or 1, and n is an integer of 1 to 10; when X is ##STR4## Y is any of CH.sub.3, CF.sub.3 and C.sub.2 H.sub.5, and (1) when Y is CH.sub.3, L is 0 or an integer of 5 to 8, m is 0 or 1, and n is an integer of 1 to 10, (2) when Y is CF.sub.3, L is an integer of 5 to 8, m is 1, and n is an integer of 1 to 10 and (3) when Y is C.sub.2 H.sub.5, L is 0, m is 0, and n is an integer of 4-10.

Dioxane type liquid crystal substance

An antiferroelectric liquid crystal compound which is a compound represented by ##STR1## wherein R denotes a linear aliphatic alkyl group having 6 to 14 carbon atoms; A denotes a single bond or an oxygen atom; X and Y independently denote a hydrogen atom or a fluorine atom but they are not hydrogen atoms at the same time; h and i are independently 1 or 2; m is an integer of 3 to 10; Z denotes CH.sub.3, C.sub.2 H.sub.5 or CF.sub.3 ; k is 0 or an integer of 5 to 8; l is 0 or 1; n is an integer of 1 to 6; W denotes CH.sub.3 or CF.sub.3 ; when W is CH.sub.3, p and q are both 0 and r is 8; when W is CF.sub.3, p is 5 to 8, q is 1 and r is 1 to 4; and C* denotes an asymmetric carbon atom, and a liquid crystal display device using same.

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Tsukuba, Japan

Hiroshi Mineta