US4510069A
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Cyclohexane derivatives
Assignee: Merck Patent GmbH
•
Filing: 1983-08-26
•
Granted: 1985-04-09
•
Expires: 2003-08-26
Abstract
Abstract Cyclohexane derivatives of formula I R.sup.1 --(A.sup.1).sub.m --Z.sup.1 --A--Z.sup.2 --(A.sup.2).sub.n --R 2 I wherein R 1 and R 2 are each H, an alkyl group which has 1-10 C atoms and in which one or two CH 2 groups can also be replaced by O atoms, F, CL, Br, CN or --O--COR, A 1 and A 2 are each 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo(2,2,2)-octylene or pyrimidine-2,5-diyl groups which are unsubstituted or substituted by 1-4 F atoms, A is a 1,4-cyclohexylene group which is substituted in the 1-position and/or 4-position by alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, each of which has 1-5 C atoms, F, Cl, Br and/or CN and which can also carry 1 or 2 further F, Cl or Br atoms 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, R is an alkyl group which has 1-5 C atoms, m is 1 or 2 and n is 0 or 1, it being possible, where m=2, for the two groups A 1 to be identical or different from one another; and the acid addition salts of those compounds which are basic, are suitable for use as components of liquid-crystal dielectrics.
Inventors
- 👤 Rudolf Eidenschink
- 👤 Gunther Haas
- 👤 Ludwig Pohl
- 👤 Michael Romer
- 👤 Bernhard Scheuble
- 👤 Georg Weber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 15:59
CPC Classifications
C; C07; C07C; C07C255/00; C07C255/01; C07C255/24; C07C255/28; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C13/00; C07C13/28; C07C17/00; C07C17/07; C07C17/08; C07C17/093; C07C17/18; C07C23/00; C07C23/18; C07C43/00; C07C43/02; C07C43/18; C07C43/184; C07C43/20; C07C43/21; C07C43/225; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/10; C07D211/14; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C09K19/32; C09K19/321; C09K19/34; C09K19/3402; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3469; C09K19/3483; C07C2601/00; C07C2601/12; C07C2601/14; C09K2019/3422
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
227 words
A liquid-crystal dielectric useful for electrooptical display elements and comprising at least two liquidcrystal components, wherein at least one of said components is a compound of the formula R.sup.1 --(A.sup.1).sub.m --Z.sup.1 --A--Z.sup.2 --(A.sup.2).sub.n --R.sup.2 wherein R 1 and R 2 are each independently H; alkyl of 1-10 C atoms; alkyl of 1-10 C atoms in which one or two CH 2 groups is optionally replaced by 0 atoms; F; Cl; Br; CN; or --O--COR; A 1 and A 2 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo(2,2,2)octylene or pyrimidine-2,5-diyl, each of which is unsubstituted or substituted by 1-4 F atoms; A is 1,4-cyclohexylene which is substituted in the 1-position, the 4-position or the 1,4-positions by alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, each of 1-5 C atoms, F, Cl, Br, CN or a combination thereof and which is optionally also substituted by 1 or 2 of F, Cl, Br or CN or a combination thereof; Z 1 and Z 2 are each independently --CO--O, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O or a single bond; R is alkyl of 1-5 C atoms; m is 1 or 2 and n is 0 or 1, wherein when m is 2, the two A 1 groups are identical or different from one another; or an acid addition salt thereof for those compounds which are basic.
Claim 2
Dependent Claim
227 words
A liquid-crystal dielectric useful for electrooptical display elements and comprising at least two liquidcrystal components, wherein at least one of said components is a compound of the formula R.sup.1 --(A.sup.1).sub.m --Z.sup.1 --A--Z.sup.2 --(A.sup.2).sub.n --R.sup.2 wherein R 1 and R 2 are each independently H; alkyl of 1-10 C atoms; alkyl of 1-10 C atoms in which one or two CH 2 groups is optionally replaced by 0 atoms; F; Cl; Br; CN; or --O--COR; A 1 and A 2 are each independently 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo(2,2,2)octylene or pyrimidine-2,5-diyl, each of which is unsubstituted or substituted by 1-4 F atoms; A is 1,4-cyclohexylene which is substituted in the 1-position, the 4-position or the 1,4-positions by alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy, each of 1-5 C atoms, F, Cl, Br, CN or a combination thereof and which is optionally also substituted by 1 or 2 of F, Cl, Br or CN or a combination thereof; Z 1 and Z 2 are each independently --CO--O, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O or a single bond; R is alkyl of 1-5 C atoms; m is 1 or 2 and n is 0 or 1, wherein when m is 2, the two A 1 groups are identical or different from one another; or an acid addition salt thereof for those compounds which are basic.
Claim 3
Dependent Claim
20 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --A.sup.1 --Z.sup.1 --A--Z.sup.2 --R.sup.2.
Claim 4
Dependent Claim
21 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --A.sup.1 --Z.sup.1 --A--Z.sup.2 --A.sup.2 --R.sup.2.
Claim 5
Dependent Claim
20 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --(A.sup.1).sub.2 --Z.sup.1 --A--Z.sup.2 --R.sup.2.
Claim 6
Dependent Claim
21 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --(A.sup.1).sub.2 --Z.sup.1 --A--Z.sup.2 --A.sup.2 --R.sup.2.
Claim 7
Dependent Claim
61 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Dio--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Pip--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Bic--Z.sup.1 --A--Z.sup.2 --R.sup.2 or R.sup.1 --Pyr--Z.sup.1 --A--Z.sup.2 --R.sup.2 wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, and Dio is 1,3-dioxane-2,5-diyl, Bic is bicyclo(2,2,2)-octylene, Pip is piperidine-1,4-diyl and Pyr is pyrimidine-2,5-diyl.
Claim 8
Dependent Claim
39 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2 or R.sup.1 --Dio--Z.sup.1 --A--Z.sup.2 --R.sup.2 wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, and Dio is 1,3-dioxane-2,5-diyl.
Claim 9
Dependent Claim
91 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --Phe--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2 R.sup.1 --Dio--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2 R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2 R.sup.1 --Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2 R.sup.1 --Phe--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Phe--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Cy--Phe--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Cy--Cy--Z.sup.1 --A--Z.sup.2 --R.sup.2 R.sup.1 --Phe--Phe--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2 R.sup.1 --Phe--Phe--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2 R.sup.1 --Phe--Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2 R.sup.1 --Phe--Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2 R.sup.1 --Cy--Phe--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2 R.sup.1 --Cy--Phe--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2 R.sup.1 --Cy--Cy--Z.sup.1 --A--Z.sup.2 --Phe--R.sup.2 or R.sup.1 --Cy--Cy--Z.sup.1 --A--Z.sup.2 --Cy--R.sup.2 wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, and Dio is 1,3-dioxane-2,5-diyl.
Claim 10
Dependent Claim
18 words
A dielectric of claim 1 wherein R 1 and R 2 independently are each alkyl or oxa-containing alkyl.
Claim 11
Dependent Claim
18 words
A dielectric of claim 1 wherein A 1 and A 2 , independently, are each 1,4-cyclohexylene or 1,4-phenylene.
Claim 12
Dependent Claim
14 words
A dielectric of claim 1 wherein A is 1,4-cyclohexylene substituted only in the 1-position.
Claim 13
Dependent Claim
21 words
A compound of claim 11 wherein the 1- substituent is --CN, --CH 3 , CH 3 O-- or --CF 3 .
Claim 14
Dependent Claim
15 words
A dielectric of claim 1 wherein Z 1 and Z 2 are each single bonds.
Claim 15
Dependent Claim
13 words
A dielectric of claim 1 wherein m is 1 and n is 0.
Claim 16
Dependent Claim
78 words
A dielectric of claim 1 wherein said at least one compound of the formula is R.sup.1 --Phe--A--R.sup.2 R.sup.1 --Phe--CO--O--A--R.sup.2 R.sup.1 --Phe--O--CO--A--R.sup.2 R.sup.1 --Phe--CH.sub.2 CH.sub.2 --A--R.sup.2 R.sup.1 --Phe--O--CH.sub.2 --A--R.sup.2 R.sup.1 --Phe--CH.sub.2 --O--A--R.sup.2 R.sup.1 --Cy--A--R.sup.2 R.sup.1 --Cy--CO--O--A--R.sup.2 R.sup.1 --Cy--O--CO--A--R.sup.2 R.sup.1 --Cy--CH.sub.2 CH.sub.2 --A--R.sup.2 R.sup.1 --Cy--O--CH.sub.2 --A--R.sup.2 R.sup.1 --Cy--CH.sub.2 --O--A--R.sup.2 R.sup.1 --Dio--A--R.sup.2 R.sup.1 --Pip--A--R.sup.2 R.sup.1 --Bic--A--R.sup.2 R.sup.1 --Pyr--A--R.sup.2 R.sup.1 --Phe--Phe--A--R.sup.2 or wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl, Bic is bicyclo(2,2,2)octylene, Pip is piperidine-1,4-diyl and Pyr is pyrimidine-2,5-diyl.
Claim 17
Dependent Claim
53 words
A dielectric of claim 1 wherein the groups R 1 --(A 1 ) m --Z 1 -- and --Z 2 --(A 2 ) n --R 2 are in the trans-position in relation to one another, and the 1- substituent on A is in the cis-position in relation to the group opposite to it.
Claim 18
Dependent Claim
7 words
The dielectric of claim 1 including r-1-cyano-1-pentyl-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane.
Claim 19
Dependent Claim
20 words
In an electro-optical display element comprising a liquid crystalline dielectric, the improvement wherein the dielectric is that of claim 1.
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