Patent EP0267585A2 successfully refreshed from Google Patents.
EP0267585A2
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Fluoroalkane derivative, its composition and liquid crystal device using same
Assignee: Canon Inc
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Filing: 1987-11-10
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Granted: —
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Expires: 2007-11-10
Abstract
Abstract A liquid crystal composition, comprising: at least one optically active mesomorphic compound having an asymmetric carbon atom to which a fluorine atom is directly bonded, and at least one mesomorphic compound having an optically active group represented by the following formula (1): wherein R 1 denotes a linear or branched alkyl group having 1 - 18 carbon atoms, x is 0 or 1, y is an integer of 0 - 8, and C* denotes an asymmetric carbon atom.
Inventors
- 👤 Hiroyuki Nohira
- 👤 Masano Kamei
- 👤 Shinichi Nakamura
- 👤 Kazuharu Katagiri
- 👤 Masahiro Terada
- 👤 Masataka Yamashita
- 👤 Yoko Canon-Ryo Yamada
- 👤 Kenji Canon-Ryo Shinjo
- 👤 Takashi Honatsugi Inoue Bldg. Iwaki
- 👤 Chieko Hioki
- 👤 Akio Yoshida
- 👤 Toshiharu Canon-Ryo Uchimi
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-08 17:48
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/42; C09K19/46; C07; C07C; C07C327/00; C09K19/06; C09K19/08; C09K19/10; C09K19/20; C09K19/2007; C09K19/2021; C09K19/2028; C09K19/28
Claims Analysis
Total Claims: 65
Claim 1
Independent Claim
79 words
A liquid crystal composition, comprising: at least one optically active mesomorphic compound having an asymmetric carbon atom to which a fluorine atom is directly bonded, and at least one mesomorphic compound having an optically active group represented by the following formula (1): wherein R 1 denotes a linear or branched alkyl group having 1 - 18 carbon atoms, x is 0 or 1, y is an integer of 0 - 8, and C * denotes an asymmetric carbon atom.
Claim 2
Dependent Claim
79 words
A liquid crystal composition, comprising: at least one optically active mesomorphic compound having an asymmetric carbon atom to which a fluorine atom is directly bonded, and at least one mesomorphic compound having an optically active group represented by the following formula (1): wherein R 1 denotes a linear or branched alkyl group having 1 - 18 carbon atoms, x is 0 or 1, y is an integer of 0 - 8, and C * denotes an asymmetric carbon atom.
Claim 3
Dependent Claim
113 words
A composition according to Claim 1, wherein said mesomorphic compound having the optically active group represented by the formula (1) is a mesomorphic compound represented by the following formula (2): wherein X 1 and X 2 respectively denote a single bond, Y 1 denotes a single bond, or A 1 and A 2 denote a divalent group containing a 6-membered ring and capable of having a substituent; R 2 and R 1 denote a linear or branched alkyl group having 4 - 16 carbon atoms and 1 - 18 carbon atoms, respectively; y is an integer of 0 - 8, x is 0 or 1, and C * denotes an asymmetric carbon atom.
Claim 4
Dependent Claim
105 words
A composition according to Claim 1 or 2, wherein said mesomorphic compound having an asymmetric carbon atom to which a fluorine atom is directly bonded is a mesomorphic compound represented by the following formula (3): wherein Y 2 denotes or X 3 denotes a single bond, X 4 denotes are respectively R 3 and R 4 respectively denote a linear or branched alkyl, alkoxyalkyl or halogenated alkyl group having 1 - 16 carbon atoms capable of including an asymmetric carbon atom; a, b, c and d are respectively 0, 1 or 2; e is 0 or 1; and C * denotes an asymmetric carbon atom.
Claim 5
Dependent Claim
42 words
A composition according to Claim 2, wherein the substituent held by A 1 and A 2 is alkyl group, alkoxy group, halogen atom of chlorine, bromine or fluorine, or cyano group, and the divalent group containing a 6- membered ring is or
Claim 6
Dependent Claim
63 words
A composition according to Claim 1, wherein at least one of the mesomorphic compounds has a spontaneous polarization P s (as measured at a temperature 15°C below the upper limit temperature of its chiral smectic phase) of 8 nC/cm 2 or above, and another at least one of the mesomorphic compounds has a spontaneous polarization P s of -8 nC/cm 2 or below.
Claim 7
Dependent Claim
199 words
A composition according to Claim 5, which comprises at least one optically active mesomorphic compound represented by the formula (2): wherein X 1 and X 2 respectively denote a single bond, Y 1 denotes a single bond, or A 1 and A 2 respectively denote a divalent 6-membered ring-containing group of each capable of having a substitutent of alkyl group, alkoxy group, halogen atom of chlorine, bromine or fluorine, or cyano group; R 2 and R 1 denote a linear or branched alkyl group having 4 - 16 carbon atoms and 1 - 18 carbon atoms, respectively; y is an integer of 0 - 8, x is 0 or 1, and C * denotes an asymmetric carbon atom; and at least one mesomorphic compound represented by the formula (3): wherein Y 2 denotes or X 3 denotes a single bond, or X 4 denotes are respectively R 3 and R 4 respectively denote a linear or branched alkyl, alkoxyalkyl or halogenated alkyl group having 1 - 16 carbon atoms capable of including an asymmetric carbon atom; a, b, c and d are respectively 0, 1 or 2; e is 0 or 1; and C" denotes an asymmetric carbon atom.
Claim 8
Dependent Claim
24 words
A liquid crystal device, comprising a pair of electrode plates, and a liquid crystal composition according to Claim 1 disposed between the electrode plates.
Claim 9
Dependent Claim
114 words
A liquid crystal device according to Claim 7, wherein said mesomorphic compound having the optically active group represented by the formula (1) is a mesomorphic compound represented by the following formula (2): wherein X 1 and X 2 respectively denote a single bond, Y 1 denotes a single bond or A 1 and A 2 denote a divalent group containing a 6-membered ring and capable of having a substituent; R 2 and R 1 denote a linear or branched alkyl group having 4 - 16 carbon atoms and 1 - 18 carbon atoms, respectively; y is an integer of 0 - 8, x is 0 or 1, and C" denotes an asymmetric carbon atom.
Claim 10
Dependent Claim
108 words
A liquid crystal device according to Claim 7 or 8, wherein said mesomorphic compound having an asymmetric carbon atom to which a fluorine atom is directly bonded is a mesomorphic compound represented by the following formula (3): wherein Y 2 denotes or X 3 denotes a single bond, or X 4 denotes are respectively R 3 and R 4 respectively denote a linear or branched alkyl, alkoxyalkyl or halogenated alkyl group having 1 - 16 carbon atoms capable of including an asymmetric carbon atom; a, b, c and d are respectively 0, 1 or 2; e is 0 or 1; and C * denotes an asymmetric carbon atom.
Claim 11
Dependent Claim
43 words
A liquid crystal device according to Claim 8, wherein the substituent held by A 1 and A 2 is alkyl group, alkoxy group, halogen atom of chlorine, bromine or fluorine, or cyano group, and the divalent group containing a 6-membered ring is or
Claim 12
Dependent Claim
69 words
A liquid crystal composition, comprising: at least one mesomorphic compound (A) in the form of an ester having an optically active asymmetric carbon atom to which a fluorine atom is directly bonded in its carboxylic acid moiety, and at least one mesomorphic compound (B) in the form of an ester having an optically active asymmetric carbon atom to which a fluorine atom is directly bonded in its alcohol moiety.
Claim 13
Dependent Claim
69 words
A liquid crystal composition, comprising: at least one mesomorphic compound (A) in the form of an ester having an optically active asymmetric carbon atom to which a fluorine atom is directly bonded in its carboxylic acid moiety, and at least one mesomorphic compound (B) in the form of an ester having an optically active asymmetric carbon atom to which a fluorine atom is directly bonded in its alcohol moiety.
Claim 14
Dependent Claim
65 words
A composition according to Claim 11, wherein the mesomorphic compound (A) is represented by the formula (4): wherein R 5 and R 6 denote a linear or branched alkyl group having 1 - 16 carbon atoms; C * denotes an asymmetric carbon atom; X 5 denotes a single bond, and A3 and A4 denote a group containing a 6-membered ring capable of having a substituent.
Claim 15
Dependent Claim
41 words
A composition according to Claim 12, wherein A3 and A 4 denote a group represented by the formula (4a): wherein Y 3 denotes a single bond, -CH = CH-, or -CH 2 CH 2 -, and ℓ is 1 or 2.
Claim 16
Dependent Claim
70 words
A composition according to Claim 11, wherein the mesomorphic compound (B) is represented by the formula (5): wherein R 7 and R 8 denote a linear or branched alkyl group having 1 - 16 carbon atoms; C* denotes an asymmetric carbon atom; X 6 denotes a single bond, -O-, or X 7 denotes and As and A 6 denote a group containing a 6-membered ring capable of having a substituent.
Claim 17
Dependent Claim
45 words
A composition according to Claim 14, wherein A 5 and A 6 in the formula (5) are a group represented by the formula (5a): wherein Y 4 denotes a single bond, -CH = CH-or -CH 2 CH 2 -, and n is 1 or 2.
Claim 18
Dependent Claim
59 words
A composition according to Claim 11, wherein at least one of the mesomorphic compounds has a spontaneous polarization (as measured at a temperature 15°C below the upper limit temperature of its chiral smectic phase) of 8 nC/cm 2 or above, and another at least one of the mesomorphic compounds has a spontaneous polarization of -8 nC/cm 2 or below.
Claim 19
Dependent Claim
219 words
A composition according to Claim 16, which comprises: at least one mesomorphic compound (A) represented by the formula (4): wherein R 5 and R 6 denote a linear or branched alkyl group having 1 - 16 carbon atoms; C * denotes an asymmetric carbon atom; X 5 denotes a single bond, and A3 and At denote a group represented by the formula (4a): wherein Y 3 denotes a single bond, -CH=CH-, or -CH 2 CH 2 , and ℓ is 1 or 2; and at least one mesomorphic compound (B) represented by the formula (5): wherein R 7 and R 8 denote a linear or branched alkyl group having 1 - 16 carbon atoms; C" denotes an asymmetric carbon atom; X 6 denotes a single bond, -O-, or X 7 denotes and A 5 and A 6 denote a group represented by the formula (5a): wherein Y 4 denotes a single bond, -CH = CH-or -CH 2 CH 2 -, and n is 1 or 2; wherein at least one of the mesomorphic compounds has a spontaneous polarization (as measured at a temperature 15°C below the upper limit temperature of its chiral smectic phase) of 8 nC/cm 2 or above, and another at least one of the mesomorphic compounds has a spontaneous polarization of -8 nC/cm 2 or below.
Claim 20
Dependent Claim
24 words
A liquid crystal device, comprising a pair of electrode plates, and a liquid crystal composition according to Claim 11 disposed between the electrode plates.
Claim 21
Dependent Claim
68 words
A liquid crystal device according to Claim 18, wherein the mesomorphic compound (A) is represented by the formula (4): wherein R 5 and R 6 denote a linear or branched alkyl group having 1 - 16 carbon atoms; C * denotes an asymmetric carbon atom; X 5 denotes a single bond, and A 3 and A4 denote a group containing a 6-membered ring capable of having a substituent.
Claim 22
Dependent Claim
42 words
A liquid crystal device according to Claim 19, wherein A3 and A4 denote a group represented by the formula (4a): wherein Y 3 denotes a single bond, -CH = CH-, or -CH 2 CH 2 , and t is 1 or 2.
Claim 23
Dependent Claim
71 words
A liquid crystal device according to Claim 18, wherein the mesomorphic compound (B) is represented by the formula (3): wherein R 7 and R 8 denote a linear or branched alkyl group having 1 - 16 carbon atoms; C" denotes an asymmetric carbon atom; X 6 denotes a single bond, -0-, or X; denotes and As and A 6 denote a group containing a 6-membered ring capable ot having a substituent.
Claim 24
Dependent Claim
43 words
A liquid crystal device according to Claim 21, wherein A 5 and A 6 in the formula (5) are a group represented by the formula (5a): wherein Y 4 denotes a single bond, -CH = CH-or -CH2CH2-, and n is 1 or 2.
Claim 25
Dependent Claim
67 words
A ferroelectric liquid crystal composition, comprising at least one mesomorphic compound (C) showing a chiral smectic phase with a spontaneous polarization P s (at a temperature 15°C below the upper limit temperature of the chiral smectic phase) of 8 nC/cm 2 or above, and at least one mesomorphic compound (D) showing a chiral smectic phase with a spontaneous polarization P s of -8 nC/cm 2 or below.
Claim 26
Dependent Claim
67 words
A ferroelectric liquid crystal composition, comprising at least one mesomorphic compound (C) showing a chiral smectic phase with a spontaneous polarization P s (at a temperature 15°C below the upper limit temperature of the chiral smectic phase) of 8 nC/cm 2 or above, and at least one mesomorphic compound (D) showing a chiral smectic phase with a spontaneous polarization P s of -8 nC/cm 2 or below.
Claim 27
Dependent Claim
27 words
A composition according to Claim 23, wherein the mesomorphic compound (C) and the mesomorphic compound (D) provide mutually reverse helical twist directions in their chiral smectic phases.
Claim 28
Dependent Claim
21 words
A composition according to Claim 23, which shows chiral smectic C phase, H phase, F phase, I phase or G phase.
Claim 29
Dependent Claim
26 words
A ferroelectric liquid crystal device, comprising a pair of electrode plates, and a ferroelectric liquid crystal composition according to Claim 23 disposed between the electrode plates.
Claim 30
Dependent Claim
27 words
A device according to Claim 26, wherein the mesomorphic compound (C) and the mesomorphic compound (D) provide mutually reverse helical twist directions in their chiral smectic phase.
Claim 31
Dependent Claim
26 words
A device according to Claim 26, wherein the ferroelectric liquid crystal composition shows chiral smectic C phase, H phase, F phase, I phase or G phase.
Claim 32
Dependent Claim
90 words
A fluoroalkane derivative represented by the formula (I): wherein Rio denotes an alkyl group having 1 - 16 carbon atoms; C* denotes an asymmetric carbon atom; R 11 denotes an alkyl group having 1 - 16 carbon atoms; Z denotes -0-or -S-; X 10 denotes a single hand, -O-, or A 10 and A 11 denote a phenylene group a cyclohexylene group or a pyrimidinylene group n2 is 1 or 2; t2 and m2 are 0 or a positive integer satisfying the relation t2 + m2 = 1 or 2.
Claim 33
Dependent Claim
90 words
A fluoroalkane derivative represented by the formula (I): wherein Rio denotes an alkyl group having 1 - 16 carbon atoms; C* denotes an asymmetric carbon atom; R 11 denotes an alkyl group having 1 - 16 carbon atoms; Z denotes -0-or -S-; X 10 denotes a single hand, -O-, or A 10 and A 11 denote a phenylene group a cyclohexylene group or a pyrimidinylene group n2 is 1 or 2; t2 and m2 are 0 or a positive integer satisfying the relation t2 + m2 = 1 or 2.
Claim 34
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-heptyloxyphenyl p-2-fluorohexylox- ybenzoate.
Claim 35
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-hexyloxycarbonylphenyl p-2-fluorohex- yloxybenzoate.
Claim 36
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-dodecyloxyphenyl p-2-fluoroheptylox- ybenzoate.
Claim 37
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p"-n-heptylphenyl p'-2-fluoroheptyloxybiphenyl-p-carboxylate.
Claim 38
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-(p"-n-octyloxyphenyl)-phenyl p-2-fluoroheptyloxybenzoate.
Claim 39
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is S-p'-n-dodecyloxyphenyl p-(2-fluorohep- tyloxy)thiobenzoate.
Claim 40
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-octyloxyphenyl p-2-fluorooctyloxyben- zoate.
Claim 41
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is 5-n-nonyl-2-[p-(p'-fluorooctyloxyben- zoyloxy)phenyl]pyridine.
Claim 42
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-(p"-n-octyloxycarbonyl)biphenyl p-2-fluorooctyloxybenzoate.
Claim 43
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is trans-p'-(p"-n-octylphenyl)cyclohexyl p-2-fluorooctyloxybenzoate.
Claim 44
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is S-p'-n-octylphenyl p-(2-fluorooctyloxy)-thiobenzoate.
Claim 45
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-decyloxyphenyl p-2-fluorononylox- ybenzoate.
Claim 46
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-(trans-p"-heptylcyciohexyl)phenyl p-2-fluorononyloxybenzoate.
Claim 47
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p"-n-pentyloxyphenyl p'-2-fluorodecyloxybiphenyl-p-carboxylate.
Claim 48
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-octyloxyphenyl p-2-fluorodecyloxyben- zoate.
Claim 49
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is S-p'-n-octyloxyphenyl p-(2 fluorodecyloxy)-thiobenzoate.
Claim 50
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is 5-n-octyl-2-[p-(p'-2-fluorodecyloxyben- zoyloxy)phenyl]pyrimidine.
Claim 51
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-(p"-n-heptyloxycarbonyl)biphenyl p-2-fluorodecyloxybenzoate.
Claim 52
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is trans-p'-(trans-p"-n-octylcyclohexyl)-cyclohexyl p-2-fluorodecyloxybenzoate.
Claim 53
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is S-p'-n-heptyloxyphenyl p-(2-fluoroun- decyloxy)thiobenzoate.
Claim 54
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-(n-dodecyloxycarbonyl)phenyl p-2-fluoroundecyloxybenzoate.
Claim 55
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-n-tetradecyloxyphenyl p-2-fluorododecyloxybenzoate.
Claim 56
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p-n-nonyloxyphenyl p-2-fluorododecylox- ybenzoate.
Claim 57
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is S-p'-n-dodecyloxyphenyl p-(2-fluorododecyloxy)thiobenzoate.
Claim 58
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is trans-p"-n-propylcyclohexyl p'-2-fluorododecyloxybiphenyl-p-carboxylate.
Claim 59
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-butyloxyphenyl p-2-fluorothiodecylox- ybenzoate.
Claim 60
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-(p"-decyloxycarbonyl)biphenyl p-2-fluorotridecyloxybenzoate.
Claim 61
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p'-n-heptyloxyphenyl p-2-fluorotetradecyloxybenzoate.
Claim 62
Dependent Claim
11 words
A fluoroalkane derivative according to Claim 29, which is p"-n-hexylphenyl p'-2-fluorohexadecyloxybiphenyl-p-carboxylate.
Claim 63
Dependent Claim
12 words
A fluoroalkane derivative according to Claim 29, which is p'-n-hexyloxyphenyl p-2-fluorohex- adecyloxybenzoate.
Claim 64
Dependent Claim
13 words
A liquid crystal, containing at least one fluoroalkane derivative according to Claim 29.
Claim 65
Dependent Claim
19 words
A liquid crystal device, comprising a pair of electrode plates and a liquid crystal composition according to Claim 60.
References Cited (Backward Citations)
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