US4576732A
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Ferroelectric liquid crystal compounds and liquid crystal compositions
Assignee: HITACHI Ltd AND CHISSO CORP 7-3 MARUNOUCHI 2-CHOME CHIYODA-KU TOKYO JAPAN A CORP OF JAPAN
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Filing: 1983-11-28
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Granted: 1986-03-18
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Expires: 2003-11-28
Abstract
Abstract The present invention is characterized by a smectic liquid crystal compound represented by the following formula: <IMAGE> wherein R is selected from alkyl and alkoxy groups; X from <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> <IMAGE> +TR <IMAGE> m and n are natural numbers; and R* is an optically active group containing an asymmetric carbon atom, and a liquid crystal composition containing said compound as a component. This compound is excellent in optical stability and high-speed response.
Inventors
- 👤 Masato Isogai
- 👤 Shintaroo Hattori
- 👤 Kishiroo Iwasaki
- 👤 Teruo Kitamura
- 👤 Akio Mukoh
- 👤 Takashi Inukai
- 👤 Kenji Furukawa
- 👤 Kanetsugu Terashima
- 👤 Shinichi Saitoh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 08:27
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/10; C09K19/20; C09K19/2007; C09K19/2021; C09K19/12; C09K19/126; C09K19/22; C09K19/42; C09K19/48; C09K19/52; C09K19/60; C09K19/603
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
137 words
A ferroelectric liquid crystal compound selected from the group consisting of: 4-n-heptyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-pentyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-heptyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, p-n-pentyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-octyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecyloxybenzoic acid 4'-(2-methylvbutoxycarbonyl)-4-biphenylyl ester, p-n-hexylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, ' -n-decyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzoate, p-n-octyloxybenzyl S-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ether, and 4'-n-octyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzyl ether.
Claim 2
Dependent Claim
137 words
A ferroelectric liquid crystal compound selected from the group consisting of: 4-n-heptyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-pentyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-heptyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, p-n-pentyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-octyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecyloxybenzoic acid 4'-(2-methylvbutoxycarbonyl)-4-biphenylyl ester, p-n-hexylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, ' -n-decyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzoate, p-n-octyloxybenzyl S-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ether, and 4'-n-octyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzyl ether.
Claim 3
Dependent Claim
95 words
The ferroelectric liquid crystal compound as set forth in claim 1, wherein said compound is selected from the group consisting of: 4-n-heptyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-heptyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, p-n-pentyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-octyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, 4'-n-decyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzoate, p-n-octyloxybenzyl S-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ether, and ' -n-octyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzyl ether.
Claim 4
Dependent Claim
161 words
A ferroelectric liquid crystal composition containing as components thereof a mixture of a plurality of ferroelectric liquid crystal compounds, said ferroelectric liquid crystal compounds comprising at least one compound from the group consisting of: 4-n-heptyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-pentyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-heptyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, P0 4-n-nonyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, p-n-pentyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-octyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonyloxybenzoic acid 4'(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, ' -n-decyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzoate, p-n-octyloxybenzyl S-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ether, and 4'-n-octyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzyl ether.
Claim 5
Dependent Claim
161 words
A ferroelectric liquid crystal composition containing as components thereof a mixture of a plurality of ferroelectric liquid crystal compounds, said ferroelectric liquid crystal compounds comprising at least one compound from the group consisting of: 4-n-heptyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-pentyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-heptyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, P0 4-n-nonyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-undecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, p-n-pentyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-octyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonyloxybenzoic acid 4'(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-nonylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-decylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-undecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-dodecylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, ' -n-decyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzoate, p-n-octyloxybenzyl S-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ether, and 4'-n-octyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzyl ether.
Claim 6
Dependent Claim
101 words
The ferroelectric liquid crystal composition as set forth in claim 3, wherein said at least one compound from said group is selected from the subgroup consisting of: 4-n-heptyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyloxy-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-hexyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-heptyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-octyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-nonyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-decyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, 4-n-dodecyl-4'-biphenylcarboxylic acid p'-(2-methylbutoxycarbonyl)phenyl ester, p-n-pentyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-octyloxybenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-hexylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, p-n-heptylbenzoic acid 4'-(2-methylbutoxycarbonyl)-4-biphenylyl ester, 4'-n-decyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzoate, p-n-octyloxybenzyl S-4'-(2-methylbutoxycarbonyl)-4-biphenylyl ether, and ' -n-octyloxy-4-biphenylyl S-p-(2-methylbutoxycarbonyl)benzyl ether.
Claim 7
Dependent Claim
27 words
The ferroelectric liquid crystal composition as set forth in claim 4, wherein said plurality of ferroelectric liquid crystal compounds includes at least two selected from said sub-group.
Claim 8
Dependent Claim
34 words
The ferroelectric liquid crystal composition as set forth in claim 4, wherein said plurality of ferroelectric liquid crystal compounds includes at least one selected from said sub-group and a further ferroelectric liquid crystal compound.
Claim 9
Dependent Claim
26 words
The ferroelectric liquid crystal composition as set forth in claim 6, wherein said further ferroelectric liquid crystal compound is selected from the group consisting of: ##STR150##
Claim 10
Dependent Claim
22 words
The ferroelectric liquid crystal composition as set forth in claim 6, wherein said further ferroelectric liquid crystal compound is 2-methylbutyl p-alkyloxybenzylidene-p'-amino cinnamate.
Claim 11
Dependent Claim
27 words
The ferroelectric liquid crystal composition as set forth in claim 3, wherein said plurality of ferroelectric liquid crystal compounds includes at least two selected from said group.
Claim 12
Dependent Claim
34 words
The ferroelectric liquid crystal composition as set forth in claim 3, wherein said plurality of ferroelectric liquid crystal compounds includes at least one selected from said group and a further ferroelectric liquid crystal compound.
Claim 13
Dependent Claim
26 words
The ferroelectric liquid crystal composition as set forth in claim 10, wherein said further ferroelectric liquid crystal compound is selected from the group consisting of: ##STR151##
Claim 14
Dependent Claim
22 words
The ferroelectric liquid crystal composition as set forth in claim 10, wherein said further ferroelectric liquid crystal compound is 2-methylbutyl p-alkyloxybenzylidene-p'-amino cinnamate.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1989-03-17 | 1989-09-16 | 1990-03-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-03-17 | 1993-09-16 | 1994-03-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-03-17 | 1997-09-16 | 1998-03-18 | $7700.00 | Window Closed / Lapsed |