US4704227A
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Liquid crystal compounds
Assignee: Merck Patent GmbH
•
Filing: 1985-02-15
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Granted: 1987-11-03
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Expires: 2005-02-15
Abstract
Abstract Compounds of the formula I R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 I wherein R 1 and R 2 are each H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group with in each case 1-10 C atoms, F, Cl, Br, CN or R 3 --A 3 --Z 2 --, A 1 is --A--, --A 4 --A--or --A--A 4 --, A is a 1,3-dioxane-2,5-diyl or a 1,3-dithiane-2,5-diyl group, A 2 , A 3 are each a 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, and A 4 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl or 1,4-bicyclo(2,2,2)octylene group, or a 1,4-phenylene, pyrimidine-2,5-diyl or pyridazine-3,6-diyl group which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups, Z 1 and Z 2 are each --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O or a single bond and R 3 is H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group with in each case 1-10 C atoms, F, Cl, Br or CN, with the proviso that (a) at least one group A 2 , A 3 and/or A 4 contains lateral substituents, (b) 1,3-dioxane-2,5-diyl and 1,3-dithiane-2,5-diyl groups are not substituted by alkoxy, alkanoyl, alkanoyloxy, alkoxycarbonyl, F, Cl, Br, CN or R 3 --A 3 --Z 2 in the 2-position and piperidine-1,4-diyl groups are not substituted by these radicals in the 1-position, (c) Z 1 is not --CH 2 CH 2 --if A 1 is --A--and (d) Z 1 is not --CO--O--if A 1 is --A--A 4 --and --A 2 --R 2 is 3-chloro-4-cyanophenyl and (e) all lateral substituents on pyrimidine-2,5-diyl and pyridazine-3,6-diyl groups are attached to C-atoms, can be used as components of liquid crystal phases.
Inventors
- 👤 Joachim Krause
- 👤 Andreas Wachtler
- 👤 Reinhard Hittich
- 👤 Georg Weber
- 👤 Bernhard Scheuble
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 10:25
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; C07D319/00; C07D319/04; C07D319/06; C07D339/00; C07D339/08; C07D405/08; C07D405/10; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3402; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3466; C09K19/3491; C09K2019/3422
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
212 words
In a liquid crystalline phase comprising at least two components, the improvement wherein at least one component is a compound of the formula R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 wherein R 1 and R 2 each independently is H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group in each case of 1-10 C atoms, F, Cl, Br, CN or R 3 --A 3 --Z 2 --, A 1 is --A--, --A 4 --A-- or --A--A 4 --, A is 1,3-dioxane-2,5-diyl, A 2 , A 3 each independently is 1,4-cyclohexylene, 1,4-phenylene and A 4 or 1,4-phenylene, which is substituted by F, Z 1 and Z 2 each independently is --CO--O--, O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O or a single bond and R 3 is H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group in each case of 1-10 C atoms, F, Cl, Br or CN, with the proviso that (a) at least one group of A 2 , A 3 and A 4 contains a single lateral substituent, (b) 1,3-dioxane-2,5-diyl is not substituted by alkoxy, alkanoyl, alkanoyloxy, alkoxycarbonyl, F, Cl, Br, CN or R 3 --A 3 --Z 2 in the 2-position and (c) Z 1 is not --CH 2 CH 2 -- when A 1 is --A--.
Claim 2
Dependent Claim
212 words
In a liquid crystalline phase comprising at least two components, the improvement wherein at least one component is a compound of the formula R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --R.sup.2 wherein R 1 and R 2 each independently is H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group in each case of 1-10 C atoms, F, Cl, Br, CN or R 3 --A 3 --Z 2 --, A 1 is --A--, --A 4 --A-- or --A--A 4 --, A is 1,3-dioxane-2,5-diyl, A 2 , A 3 each independently is 1,4-cyclohexylene, 1,4-phenylene and A 4 or 1,4-phenylene, which is substituted by F, Z 1 and Z 2 each independently is --CO--O--, O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O or a single bond and R 3 is H, an alkyl, alkoxy, alkanoyl, alkanoyloxy or alkoxycarbonyl group in each case of 1-10 C atoms, F, Cl, Br or CN, with the proviso that (a) at least one group of A 2 , A 3 and A 4 contains a single lateral substituent, (b) 1,3-dioxane-2,5-diyl is not substituted by alkoxy, alkanoyl, alkanoyloxy, alkoxycarbonyl, F, Cl, Br, CN or R 3 --A 3 --Z 2 in the 2-position and (c) Z 1 is not --CH 2 CH 2 -- when A 1 is --A--.
Claim 3
Dependent Claim
20 words
A phase of claim 1 wherein at least one component is a compound of the formula R.sup.1 --A--Z.sup.1 --A.sup.2 --R.sup.2.
Claim 4
Dependent Claim
57 words
A phase of claim 1 wherein at least one component is a compound of the formula R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2 R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2 R.sup.1 --A--Z.sup.1 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --R.sup.2 R.sup.1 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.2 R.sup.1 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.2 --R.sup.2 R.sup.3 --A.sup.3 --A--Z.sup.1 --A.sup.2 --R.sup.2.
Claim 5
Dependent Claim
118 words
A phase of claim 1 wherein at least one component is a compound of the formula R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2 R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2 R.sup.1 --A.sup.4 --A--A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.1 --A--A.sup.4 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3 R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2 R.sup.3 --A.sup.3 --A--A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2 R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--A.sup.2 --R.sup.2 R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --A.sup.2 --R.sup.2.
Claim 6
Dependent Claim
48 words
A phase of claim 1 wherein at least one component is a compound of the formula R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --Z.sup.2 --A--A.sup.4 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --A.sup.4 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3 R.sup.3 --A.sup.3 --A--A.sup.4 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3.
Claim 7
Dependent Claim
24 words
A phase of claim 1 wherein at least one component is a compound wherein R 1 and R 2 each is alkyl or alkoxy.
Claim 8
Dependent Claim
27 words
A phase of claim 1 wherein at least one component is a compound wherein R 1 and R 2 each is CN, F, Cl, alkyl or alkoxy.
Claim 9
Dependent Claim
27 words
A phase of claim 1 wherein at least one component is a compound wherein A 2 , A 3 and A 4 each is 1,4-cyclohexylene or 1,4-phenylene.
Claim 10
Dependent Claim
27 words
A phase of claim 1 wherein at least one component is a compound wherein Z 1 and Z 2 each is --CO--O--, --O--CO-- or a single bond.
Claim 11
Dependent Claim
81 words
A phase of claim 1 wherein at least one component is a compound of the formula R.sup.1 --Dio--COO--Phe--R.sup.2 R.sup.1 --Dio--OCO--Phe--R.sup.2 R.sup.1 --Dio--Phe--OCO--Phe--R.sup.2 R.sup.1 --Dio--Phe--CH.sub.2 CH.sub.2 --Phe--R.sup.2 R.sup.1 --Dio--Phe--CH.sub.2 CH.sub.2 --Cy--R.sup.2 R.sup.1 --Dio--Phe--CH.sub.2 CH.sub.2 --Phe--Cy--R.sup.3 R.sup.1 --Dio--Phe--R.sup.2 R.sup.1 --Dio--Phe--Phe--R.sup.2 R.sup.1 --Dio--Phe--Phe--Cy--R.sup.3 R.sup.1 --Dio--Cy--Phe--R.sup.2 R.sup.1 --Cy--Dio--Phe--R.sup.2 R.sup.1 --Dio--CH.sub.2 CH.sub.2 --Phe--Phe--R.sup.2 R.sup.1 --Dio--CH.sub.2 CH.sub.2 --Phe--Phe--Cy--R.sup.2 R.sup.1 --Dio--CH.sub.2 CH.sub.2 --Phe--Cy--R.sup.2 wherein Cy is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl, Phe is 1,4-phenylene or is 1,4-phenylene with a single lateral substituent and each compound contains one lateral substituent.
Claim 12
Dependent Claim
33 words
A phase of claim 1 wherein at least one component is a compound of the formula R.sup.1 --Dio--A.sup.4 --CO--O--Q--CN wherein Dio is 1,3-dioxane-2,5-diyl, Q is 3-fluoro-1,4-phenylene and A 4 is 1,4-phenylene or 1,4-cyclohexylene.
Claim 13
Dependent Claim
21 words
In a liquid crystal display element, comprising a liquid crystal phase, the improvement wherein the phase is one of claim 1.
Claim 14
Dependent Claim
21 words
In an electrooptical display element comprising a liquid crystal dielectric, the improvement wherein the dielectric is a phase of claim 1.
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