Lactic acid derivative, liquid crystal composition containing same and liquid crystal device

Claim 2

An optically active lactic acid derivative represented by the following formula (I): wherein R is a saturated or unsaturated hydrocarbon group of a linear, branched or cyclic structure having 4 to 20 carbon atoms; Ra is -CO-Rb or -CH 2 -Rc wherein Rb is a releasable chemically active group, and Rc is a releasable chemically active group; and C with * represents an asymmetric carbon atom.

Claim 3

A lactic acid derivative according to claim 1 wherein Ra is -CO-Rb, and Rb is hydroxy group, halogen atom or phenoxy group.

Claim 4

A lactic acid derivative according to claim 1 wherein Ra is -CH 2 -Rc, and Rc is hydroxy group, halogen atom, phenoxy group, toluenesulfonic acid group,

Claim 7

A lactic acid derivative according to any preceding claim wherein R is a linear, branched or cyclic saturated or unsaturated hydrocarbon group having 6-16 carbon atoms.

Claim 8

A lactic acid derivative according to any preceding claim wherein R is a group selected from linear alkyls, branched alkyls, cycloalkyls, linear alkenyls, branched alkenyls, cycloalkenyls, linear alkadienyls, branched alkadienyls, cycloalkadienyls, linear alkatrienyls, branched alkatrienyls, cycloalkatrienyls, linear alkynyls, branched alkynyls, and cycloalkynyls.

Claim 9

A lactic acid derivative according to claim 1 selected from ethyl-2-butoxypropionate, ethyl-2-pentyloxypropionate, ethyl-2-hexyloxy- propionate, ethyl-2-heptyloxypropionate, ethyl-2-octyloxypropionate, ethyl-2-nonyloxypropionate, ethyl-2-decyloxypropionate, ethyl-2-undecyloxy- propionate, ethyl-2-dodecyloxypropionate, ethyl-2- tridecyloxypropionate, ethyl-2-tetradecyloxy- propionate, ethyl-2-pentadecyloxypropionate, ethyl-2-hexadecyloxypropionate, ethyl-2-octadecyloxy- propionate, ethyl-2-nonadecyloxypropionate, ethyl-2-eicosyloxypropionate, 2-butoxypropionic acid, 2- heptyloxypropionic acid, 2-butoxypropanol, 2-pentyloxypropanol, 2-hexyloxypropanol, 2- heptyloxypropanol, 2-octyloxypropanol, 2-nonyloxy- propanol, 2-decyloxypropanol, 2-undecyloxypropanol, 2-dodecyloxypropanol, 2-tridecyloxypropanol, 2-tetradecyloxypropanol, 2-pentadecyloxypropanol, 2-hexadecyloxypropanol, 2-octadecyloxypropanol, 2- nonadecyloxypropanol, and 2-eicosyloxypropanol.

Claim 10

A lactic acid derivative according to any preceding claim which is a mesomorphic compound.

Claim 11

A liquid crystal composition, containing a lactic acid derivative according to any preceding claim.

Claim 12

A lactic acid derivative having an optically active group represented by the following formula (A) or (B): and wherein R A and R B are respectively a saturated or unsaturated hydrocarbon group of a linear, branched or cyclic structure having 1 to 20 carbon atoms and C with * represents an asymmetric carbon atom.

Claim 13

A lactic acid derivative having an optically active group represented by the following formula (A) or (B): and wherein R A and R B are respectively a saturated or unsaturated hydrocarbon group of a linear, branched or cyclic structure having 1 to 20 carbon atoms and C with * represents an asymmetric carbon atom.

Claim 14

A lactic acid derivative according to claim 9 wherein the groups R A and R B are respectively a group selected from linear alkyls, branched alkyls, cycloalkyls, linear alkenyls, branched alkenyls, cycloalkenyls, linear alkadienyls, branched alkadienyls, cycloalkadienyls, linear alkatrienyls, branched alkatrienyls, cycloalkatrienyls, linear alkynyls, branched alkynyls, and cycloalkynyls.

Claim 15

A lactic acid derivative according to claim 9 or claim 10 wherein said optically active group is incorporated into a compound selected from azo derivatives, azoxy derivatives, ring-assembly hydrocarbon derivatives, condensed polycyclic hydrocarbon derivatives, heterocyclic derivatives, condensed heterocyclic derivatives, and ring-assembly heterocyclic derivatives.

Claim 16

A lactic acid derivative according to any of claims 9 to 11 wherein said optically active group is incorporated into a compound selected from azobenzene derivatives, azoxybenzene derivatives, biphenyl derivatives, terphenyl derivatives, phenylcyclohexane derivatives, benzoic acid derivatives, pyrimidine derivatives, pyrazine derivatives, pyridine derivatives, stilbene derivatives, tolan derivatives, chalcone derivatives, bicyclohexane derivatives, and cinnamic acid derivatives.

Claim 17

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (1): wherein R 1 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 18

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (2): wherein R 2 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 19

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (3): wherein R 3 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 20

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (4): wherein R 4 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms m and n are respectively 1 or 2, and C with * represents an asymmetric carbon atom.

Claim 21

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (5): wherein R 5 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, m and n are respectively 1 or 2, and C with * represents an asymmetic carbon atom.

Claim 22

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (6): wherein R 6 is an alkyl or alkoxy group having 1-20 carbon atoms, R B is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 23

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (7): wherein R 7 is an alkyl or alkoxy group having 1-20 carbon atoms, R B is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 24

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (8): wherein R 8 is an alkyl or alkoxy group having 1-20 carbon atoms, R B is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 25

A lactic acid derivative according to claim 9 selected from 4'-hexyl-4-α-butoxy- propanoyloxyazo-benzene, 4'-heptyl-4-α-butoxy- propanoyloxyazo-benzene, 4'-octyl-4-d-butoxy- propanoyloxyazo-benzene, 4'-hexyl-4-α-butoxy- propanoyloxyazo-benzene, 4'-octyl-4-J-heptyloxy- propanoyloxyazo-benzene, 4'-hexyloxy-4-α-heptyloxy- propanoyloxyazo-benzene, 4'-hexyloxy-4-d-butoxy- propanoyloxyazoxy-benzene, 4'-octyl-4-d-heptyloxy- propanoyloxyazoxy-benzene, 4'-hexyloxy-4-α-heptyl- oxypropanoyloxyazoxy-benzene, 5-decyl-2-(4'-α-pentyloxypropanoyloxyphenyl)-pyrimidine, 4-octyloxybenzoic acid(4'-α-octadecyloxy-propanoyl- oxyphenyl)ester, 4-octyloxybenzoic acid(4'-α-dodecyloxypropanoyloxyphenyl)ester, 4-heptylbi- phenylcarboxylic acid(4"-α-heptyloxypropanoyloxyphenyl)ester, 4-octyloxybiphenylcarboxylic acid (4'-(4"-α-octyloxypropanoyloxybenzoyloxy)phenyl) ester, 4-pentyloxybenzoic acid (4'-(4"-α-nonyloxy- propanoyloxybiphenylcarboxyl)phenyl)ester,4-heptyl- biphenylcarboxylic acid(4'-(4"-e(-dodecyloxy- propanoyloxybenzoyloxy)phenyl)ester, 4-heptylbiphenyl- carboxylic acid(4'-(4"-α-pentyloxypropanoyl- oxybiphenylcarboxyl)phenyl)ester, 5-nonyl-2-(α-propyloxyphenyl)pyrimidine, 4-pentylbiphenyl- carboxylic acid(4'-(4"-α-ethoxypropanoyloxybenzoyl- oxy)phenyl)ester, heptyloxypropyl-4'-octyloxybiphenyl-4-carboxylate, butoxypropyl-4'-octyloxybiphenyl-4-carboxylate, 4-[5-(4'-butylphenyl)pyridine-2-yl]-benzoic acid-2'-dodecyloxypropyl ester, 4-(5-heptylpyridine-2-yl)benzoic acid-2'-decyloxypropyl ester, α-propyloxypropyl-4'-heptyl-terphenylcarboxylate, [5-(4'-pentyleyclo- hexyl)pyrimidine-2-yl]benzoie acid-2'-ethoxypropyl ester, and α-octadecyloxypropyl-4'-heptylbiphenyl-4-carboxylate.

Claim 26

A lactic acid derivative according to any of claims 9 to 21 which is a mesomorphic compound.

Claim 27

A lactic acid derivative according to claim 9 which is a compound represented by the following formula (Q): wherein R C is an alkyl group having 1-20 carbon atoms; R D is an alkyl or alkoxy group having 4 to 20 carbon atoms; 1, m and n are respectively 0 or an integer satisfying the relationship: 3 ≥ 1 + m + n ≥ 1; and are respectively a 1,4-substituted 6-member ring group.

Claim 28

A lactic acid derivative according to claim 23 wherein and are respectively a 1,4-substituted hydrocarbon ring group.

Claim 29

A lactic acid derivative according to claim 24 wherein said 1,4-substituted hydrocarbon ring group is a 1,4-substituted aromatic ring group.

Claim 30

A lactic acid derivative according to claim 25 wherein the 1,4-substituted aromatic ring group is 1,4-phenylene group.

Claim 31

A lactic acid derivative according to claim 23 wherein and are respectively a 1,4-substituted heterocyclic group.

Claim 32

A lactic acid derivative according to claim 27 wherein the 1,4-substituted heterocyclic group is 1,4-pyrimidinylene group.

Claim 33

A liquid crystal composition, comprising 0.1 to 100 parts by weight of a lactic acid derivative according to any of claims 9 to 28, and 100 parts by weight of another liquid crystal component.

Claim 34

A liquid crystal composition according to claim 29 wherein said another liquid crystal component is selected from a Schiff base-type ferroelectric liquid crystal compound, an ester-type ferroelectric liquid crystal compound, an azoxy-type ferroelectric liquid crystal compound, a biphenyl-type ferroelectric liquid crystal compound, a liquid crystal material showing cholesteric phase, and a liquid crystal material showing a chiral smectic phase.

Claim 35

A liquid crystal composition according to claim 30 wherein said chiral smectic phase is chiral smectic C phase.

Claim 36

A liquid crystal device, comprising a pair of base plates, and a liquid crystal material showing a smectic phase and a higher temperature phase, said liquid crystal material comprising a mesomorphic compound having an optically active group represented by the formula (A) or (B) shown below or a liquid crystal composition containing the mesomorphic compound, said liquid crystal material being in the smectic phase formed by phase transition from the higher temperature phase: and wherein R A and R B are respectively a saturated or unsaturated hydrocarbon group of a linear, branched or cyclic-structure having 1 to 20 carbon atoms and C with * represents an asymmetric carbon atom.

Claim 37

A liquid crystal device, comprising a pair of base plates, and a liquid crystal material showing a smectic phase and a higher temperature phase, said liquid crystal material comprising a mesomorphic compound having an optically active group represented by the formula (A) or (B) shown below or a liquid crystal composition containing the mesomorphic compound, said liquid crystal material being in the smectic phase formed by phase transition from the higher temperature phase: and wherein R A and R B are respectively a saturated or unsaturated hydrocarbon group of a linear, branched or cyclic-structure having 1 to 20 carbon atoms and C with * represents an asymmetric carbon atom.

Claim 38

A liquid crystal device according to claim 32 wherein at least one of said pair of base plates has a surface having an effect of orienting the direction of the molecular axes of liquid crystal molecules constituting the liquid crystal material contacting the surface preferentially in one direction.

Claim 39

A liquid crystal device according to claim 33 wherein said effect has been imparted by rubbing.

Claim 40

A liquid crystal device according to claim 33 wherein said effect has been provided with a film formed by oblique vapor deposition.

Claim 41

A liquid crystal device according to any of claims 32 to 35 wherein said higher temperature phase is isotropic phase, cholesteric phase or nematic phase.

Claim 42

A liquid crystal device according to any of claims 32 to 36 wherein said liquid crystal material causes successive phase transition of isotropic phase, cholesteric phase, smectic A phase and a chiral smectic phase in the order named on temperature decrease.

Claim 43

A liquid crystal device according to any of claims 32 to 36 wherein said liquid crystal material causes successive phase transition of isotropic phase, cholesteric phase and chiral smectic phase in the order named on temperature decrease.

Claim 44

A liquid crystal device according to any of claims 32 to 36 wherein said liquid crystal material causes successive phase transition of isotropic phase, smectic A phase and a chiral smectic phase in the order named on temperature decrease.

Claim 45

A liquid crystal device according to any of claims 32 to 39 wherein the groups R A and R B are respectively selected from linear alkyls, branched alkyls, cycloalkyls, linear alkenyls, branched alkenyls, cycloalkenyls, linear alkadienyls, branched alkadienyls, cycloalkadienyls, linear alkatrienyls, branched alkatrienyls, cycloalkatrienyls, linear alkynyls, branched alkynyls, and cycloalkynyls.

Claim 46

A liquid crystal device according to any of claims 32 to 40 wherein said optically active group is incorporated into a compound selected from azo derivatives, azoxy derivatives, ring-assembly hydrocarbon derivatives, condensed polycyclic hydrocarbon derivatives, heterocyclic derivatives, condensed heterocyclic derivatives, and ring-assembly heterocylic derivatives.

Claim 47

A liquid crystal device according to any of claims 32 to 41 wherein said optically active group has been introduced into a compound selected from the group consisting of azobenzene derivatives, azoxybenzene derivatives, biphenyl derivatives, terphenyl derivatives, phenylcyclohexane derivatives, benzoic acid derivatives, pyrimidine derivatives, pyrazine derivatives, pyridine derivatives, stilbene derivatives, tolan derivatives, chalcone derivatives, bicyclohexane derivatives, and cinnamic acid derivatives.

Claim 48

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (1): wherein R 1 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 49

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (2): wherein R 2 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 50

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (3): wherein R 3 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 51

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (4): wherein R 4 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms m and n are respectively 1 or 2, and C with * represents an asymmetric carbon atom.

Claim 52

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (5): wherein R 5 is an alkyl or alkoxy group having 1-20 carbon atoms, R A is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, m and n are respectively 1 or 2, and C with * represents an asymmetric carbon atom.

Claim 53

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (6): wherein R 6 is an alkyl or alkoxy group having 1-20 carbon atoms, R B is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 54

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (7): wherein R 7 is an alkyl or alkoxy group having 1-20 carbon atoms, R B is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 55

A liquid crystal device according to claim 32 wherein said mesomorphic compound is a compound represented by the following formula (8): wherein R 8 is an alkyl or alkoxy group having 1-20 carbon atoms, R B is a saturated or unsaturated linear, branched or cyclic hydrocarbon group having 1-20 carbon atoms, and C with * represents an asymmetric carbon atom.

Claim 56

A liquid crystal device according to any of claims 32 to 50 which comprises a plurality of picture elements arranged in a plurality of rows, each picture element comprising a pair of oppositely spaced electrodes and said liquid crystal material disposed between the pair of electrodes, and is adapted for a line-by-line driving scheme wherein a writing signal is applied to said plurality of picture elements row by row in a writing cycle, and the thus written states of a particular row of picture elements are retained until a fresh writing signal is applied to the particular row of picture elements in the subsequent writing cycle.

Claim 57

A liquid crystal device containing a liquid crystal composition according to any of claims 8 or 29 to 31.