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US5709820A Expired / Lapsed US ⏱️ 0.0 years remaining

Alkenyl cyclohexane derivatives and liquid crystal compositions

Assignee: JNC Corp
•
Filing: 1996-05-31
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Granted: 1998-01-20
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Expires: 2016-05-31
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Abstract

Abstract Liquid crystalline alkenyl cyclohexane compounds of formula (I) having a nematic phase over a broad temperature range, a higher elastic constant ratio K 33 /K 11 and a lower viscosity, liquid crystal compositions comprising the above compounds and liquid crystal display elements using the liquid crystal compositions. ##STR1## wherein R 1 is an alkyl group of 1-15 carbons, an alkenyl group of 2-15 carbons or an alkyl or alkenyl group in which at least one of non-adjacent methylene groups (--CH 2 --) is replaced by --O--, --S--, --C.tbd.C-- or --COO--; R 2 is a hydrogen atom or an alkyl group of 1-10 carbons; m is 0-5; when m is 2 or more, any one methylene group in --(CH 2 ) m -- may be replaced by --O--; and the rings A 1 , A 2 and A 3 are independently a 1,4-cyclohexylene, a cyclohexene-1,4-diyl or a 6-membered ring group, one or two --CH 2 -- groups in said rings optionally replaced by --O-- or --S--.

Inventors

  • 👤 Takashi Kato
  • 👤 Shuichi Matsui
  • 👤 Kazutoshi Miyazawa
  • 👤 Yasuko Sekiguchi
  • 👤 Etsuo Nakagawa

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 12:57
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3402; C07; C07C; C07C13/00; C07C13/28; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/162; C07C43/18; C07C43/188; C09K19/08; C09K19/30; C09K19/3001; C09K19/3003; C09K19/3491; C09K19/42; C09K19/44; C09K19/46; C07C2601/00; C07C2601/12; C07C2601/14; C09K2019/0444; C09K2019/0448; C09K2019/0451; C09K2019/3422

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 166 words
A liquid crystalline compound of formula (I) ##STR1965## wherein R 1 is an alkyl group of 1-15 carbons, an alkenyl group of 2-15 carbons or an alkyl or alkenyl group in which one or plural non-adjacent methylene groups (--CH 2 --) is or are replaced by --O--, --S--, --C.tbd.C--! or --COO--, R 2 is a hydrogen atom or an alkyl group of 1-10 carbons; m is 0-5; when m is 2 or more, one methylene group or plural non-adjacent methylene groups in --(CH 2 ) m -- may be replaced by --O--; and the rings A 1 , A 2 and A 3 are independently a 1,4-cyclohexylene group, a cyclohexene-1,4-diyl group a 1,3-dioxane-2,5, diyl group, a tetrahydropyrane-2,5, diyl group, a 1,3-dithian-2,5-diyl group or a tetrahydrothiopyrane-2,5-diyl group, provided A 3 is not a 1,3-dioxane-2,5-diyl group when A 2 is a 1,4-cyclohexylene group and no methylene group in --(CH 2 ) m -- may be replaced by --O-- when rings A1, A2 and A3 are all 1,4-cyclohexylene groups.
Claim 2
Dependent Claim 166 words
A liquid crystalline compound of formula (I) ##STR1965## wherein R 1 is an alkyl group of 1-15 carbons, an alkenyl group of 2-15 carbons or an alkyl or alkenyl group in which one or plural non-adjacent methylene groups (--CH 2 --) is or are replaced by --O--, --S--, --C.tbd.C--! or --COO--, R 2 is a hydrogen atom or an alkyl group of 1-10 carbons; m is 0-5; when m is 2 or more, one methylene group or plural non-adjacent methylene groups in --(CH 2 ) m -- may be replaced by --O--; and the rings A 1 , A 2 and A 3 are independently a 1,4-cyclohexylene group, a cyclohexene-1,4-diyl group a 1,3-dioxane-2,5, diyl group, a tetrahydropyrane-2,5, diyl group, a 1,3-dithian-2,5-diyl group or a tetrahydrothiopyrane-2,5-diyl group, provided A 3 is not a 1,3-dioxane-2,5-diyl group when A 2 is a 1,4-cyclohexylene group and no methylene group in --(CH 2 ) m -- may be replaced by --O-- when rings A1, A2 and A3 are all 1,4-cyclohexylene groups.
Claim 3
Dependent Claim 11 words
The liquid crystalline compound of claim 1 wherein m is 0.
Claim 4
Dependent Claim 11 words
The liquid crystalline compound of claim 1 wherein m is 2.
Claim 5
Dependent Claim 14 words
The liquid crystalline compound of claim 2 wherein R 1 is an alkenyl group.
Claim 6
Dependent Claim 14 words
The liquid crystalline compound of claim 3 wherein R 1 is an alkenyl group.
Claim 7
Dependent Claim 22 words
A liquid crystal composition which comprises at least one of the liquid crystalline compounds set forth in any one of claims 1-5.
Claim 8
Dependent Claim 122 words
A liquid crystal composition which comprises: (i) as a first component, at least one of the liquid crystalline compounds set forth in any one of claims 1-5, and (ii) as a second component, at least one compound selected from the group consisting of the compounds of formulae (II-a), (II-b) and (II-c) ##STR1966## wherein R 3 is an alkyl group of 1-10 carbons, X 1 is F, Cl, OCF 3 , OCF 2 H, CF 3 , CF 2 H or CFH 2 , L 1 , L 2 , L 3 and L 4 are independently H or F, Z 1 and Z 2 are independently --(CH 2 ) 2 --, --CH═CH-- or a covalent bond and a is 1 or 2.
Claim 9
Dependent Claim 543 words
A liquid crystal composition which comprises: (i) as a first component, at least one of the liquid crystalline compounds set forth in any one of claims 1-5, (ii) as a second component, at least one compound selected from the group consisting of the compounds of formulae (III-a), (III-b), (III-c), (III-d) and (III-e) ##STR1967## wherein R 4 is F, an alkyl group of 1-10 carbons or an alkenyl group of 2-10 carbons, the methylene group (--CH 2 --) in said alkyl or alkenyl group may be replaced by an oxygen atom (--O--) provided that two or more methylene groups in series are not replaced by an oxygen atom, the ring A is a trans-1,4-cyclohexylene, 1,4-phenylene, pyrimidine-2,5-diyl or 1,3-dioxane-2,5-diyl group, the ring B is a trans-1,4-cyclohexylene, 1,4-phenylene or pyrimidine-2,5-diyl group, the ring C is a trans-1,4-cyclohexylene or 1,4-phenylene group, Z 3 is --(CH 2 ) 2 --, --COO-- or a covalent bond, L 5 and L 6 are independently H or F, and b and c are independently 0 or 1, ##STR1968## wherein R 5 is an alkyl group of 1-10 carbons, L 7 is H or F and d is 0 or 1, ##STR1969## wherein R 6 is an alkyl group of 1-10 carbons, the rings D and E are independently a trans-1,4-cyclohexylene or 1,4-phenylene group, Z 4 and Z 5 are independently --COO-- or a covalent bond, Z 6 is --COO-- or --C.tbd.C--, L 8 and L 9 are independently H or F, X 2 is F, OCF 3 , OCF 2 H, CF 3 , CF 2 H or CFH 2 , provided that when X 2 is OCF 3 , OCF 2 H, CF 3 , CF 2 H or CFH 2 , both L 8 and L 9 represent a hydrogen atom, and e, f and g are independently 0 or 1, ##STR1970## wherein R 7 and R 8 are independently an alkyl group of 1-10 carbons or an alkenyl group of 2-10 carbons, the methylene group (--CH 2 --) in said alkyl or alkenyl group may be replaced by an oxygen atom (--O--) provided that two or more methylene groups in series are not replaced by an oxygen atom, the ring G is a trans-1,4-cyclohexylene, 1,4-phenylene or pyrimidine-2,5-diyl group, the ring H is a trans-1,4-cyclohexylene or 1,4-phenylene group, Z 7 is --C.tbd.C--, --COO--, --(CH 2 ) 2 --, --CH═CH--C.tbd.C-- or a covalent bond, and Z 8 is --COO or a covalent bond, ##STR1971## wherein R 9 and R 10 are independently an alkyl group of 1-10 carbons or an alkenyl group of 2-10 carbons, the methylene group (--CH 2 --) in said alkyl or alkenyl group may be replaced by an oxygen atom (--O--) provided that two or more methylene groups in series are not replaced by an oxygen atom, the ring I is a trans-1,4-cyclohexylene, 1,4-phenylene or pyrimidine-2,5-diyl group, the ring J is a trans-1,4-cyclohexylene group, a 1,4-phenylene or pyrimidine-2,5-diyl group in which one or more hydrogen atoms on the ring may be substituted by F, the ring K is a trans-1,4-cyclohexylene or 1,4-phenylene group, Z 9 and Z 11 are independently --COO--, --(CH 2 ) 2 --, or a covalent bond, Z 10 is --CH═CH--, --C.tbd.C--, --COO-- or a covalent bond and h is 0 or 1.
Claim 10
Dependent Claim 98 words
The liquid crystal composition of claim 8, further comprising at least one compound selected from the group consisting of the compounds of formulae II-a, II-b and II-c: ##STR1972## wherein R 3 is an alkyl group of 1-10 carbons, X 1 is F, Cl, OCF 3 , OCF 2 H, CF 3 , CF 2 H, or CFH 2 , L 1 , L 2 , L 3 and L 4 are independently H or F, Z 1 and Z 2 are independently --(CH 2 ) 2 --, --CH═CH-- or a covalent bond and a is 1 or 2.
Claim 11
Dependent Claim 18 words
A liquid crystal display element comprising the liquid crystal compound set forth in any one of claims 1-5.
Claim 12
Dependent Claim 15 words
A liquid crystal display element comprising the liquid crystal composition set forth in claim 7.
Claim 13
Dependent Claim 15 words
A liquid crystal display element comprising the liquid crystal composition set forth in claim 8.
Claim 14
Dependent Claim 15 words
A liquid crystal display element comprising the liquid crystal composition set forth in claim 9.
Claim 15
Dependent Claim 27 words
The liquid crystal compound of claim 1, wherein rings A 1 , A 2 and A 3 cannot each be a 1,4-cyclohexylene group at the same time.

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