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US4943384A Expired / Lapsed US ⏱️ 0.0 years remaining

Cyclohexane derivatives

Assignee: Merck Patent GmbH
•
Filing: 1986-11-21
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Granted: 1990-07-24
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Expires: 2006-11-21
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Abstract

Abstract Cyclohexane derivatives 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 or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-groups, and/or --CO--O-- groups and/or --CH═CH-- groups, or are F, Cl, Br, CN or R 3 --A 3 --Z 2 --, A 1 is --A--, A 4 --Z o --A-- or --A--Z o --A 4 --, A is a trans-1,4-cyclohexylene or 1,4-cyclohexenylene group which is unsubstituted or is monosubstituted or polysubstituted in the 2-, 3-, 5- and/or 6-position by F and/or Cl and/or Br and/or CN and/or an alkyl group or a fluorinated alkyl group each of which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups, which trans-1,4-cyclohexylene or 1,4-cyclohexenylene group can optionally also be substituted in the 1-position and/or 4-position and one or two CH 2 groups therein are replaced by --CO--, or R 1 --A 1 -- is a cyclohexyl group which is substituted in the 3-position by an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH═CH-- groups, or is substituted in the 3-position by CN, in which cyclohexyl group one or two nonadjacent CH 2 groups can also be replaced by --O-- or --CO--, A 2 , A 3 and A 4 are each 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms and/or NO, or are 1,4-cyclohexylene wherein one or two non-adjacent CH 2 groups can also be replaced by 0 atoms, or are 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo(2,2,2)-octylene, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl groups or are --A--, Z o , Z 1 and Z 2 are each --CO--O--, --O--CO--, -- CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH 2 CO--, --COCH 2 --, --CH 2 CHCN--, --CHCNCH 2 -- or a single bond, and R 3 is H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH═CH-- groups, or is F, Cl, Br or CN, are suitable for use as components of liquid-crystal phases.

Inventors

  • 👤 Wolfgang Sucrow
  • 👤 Herbert Wolter
  • 👤 Rudolf Eidenschink

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-31 21:45
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07C; C07C13/00; C07C13/28; C07C255/00; C07C35/00; C07C35/21; C07C43/00; C07C43/02; C07C43/18; C07C43/184; C07C49/00; C07C49/385; C07C49/417; C07C49/587; C07C49/613; C07C49/657; C07C49/753; C07C69/00; C07C69/02; C07C69/12; C07C69/14; C07C69/22; C07C69/24; C07C69/74; C07C69/757; C07D319/00; C07D319/04; C07D319/06; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/08; C09K19/30; C09K19/3001; C09K19/3003; C09K19/3066; C09K19/3068; C09K19/3098; C09K19/34; C09K19/3402; C09K19/3441; C09K2019/3422

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 281 words
A liquid-crystal phase having at least two liquid crystal components, and comprising at least one transversely polarized 1,4-cyclohexylene compound 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 independently H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH═CH-- groups, or F, Cl, Br, CN or R 3 --A 3 --Z 2 --, A 1 is --A--, A 4 --Z 0 --A-- or --A--Z 0 --A 4 --, A is a group of formula (A) or (J): ##STR14## or the mirror image thereof, A 2 , A 3 and A 4 are each 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by M atoms and/or NO, or are 1,4-cyclohexylene wherein one or two non-adjacent CH 2 groups can also be replaced by 0 atoms, or are 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo-[2,2,2] octylene, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetra-hydronaphthalene-2,6-diyl groups or are --A--, Z 0 , Z 1 and Z 2 are each --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH 2 CO--, --COCH 2 --, --CH 2 CHCN--, --CHCNCH 2 -- or a single bond, and R 3 is H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH═CH-- groups, or is F, Cl, Br or CN.
Claim 2
Dependent Claim 281 words
A liquid-crystal phase having at least two liquid crystal components, and comprising at least one transversely polarized 1,4-cyclohexylene compound 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 independently H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH═CH-- groups, or F, Cl, Br, CN or R 3 --A 3 --Z 2 --, A 1 is --A--, A 4 --Z 0 --A-- or --A--Z 0 --A 4 --, A is a group of formula (A) or (J): ##STR14## or the mirror image thereof, A 2 , A 3 and A 4 are each 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by M atoms and/or NO, or are 1,4-cyclohexylene wherein one or two non-adjacent CH 2 groups can also be replaced by 0 atoms, or are 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo-[2,2,2] octylene, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetra-hydronaphthalene-2,6-diyl groups or are --A--, Z 0 , Z 1 and Z 2 are each --CO--O--, --O--CO--, --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --CH 2 CO--, --COCH 2 --, --CH 2 CHCN--, --CHCNCH 2 -- or a single bond, and R 3 is H or an alkyl group which has 1-10 C atoms and in which one or two non-adjacent CH 2 groups can also be replaced by 0 atoms and/or --CO-- groups and/or --CO--O-- groups and/or --CH═CH-- groups, or is F, Cl, Br or CN.
Claim 3
Dependent Claim 132 words
Phase according to claim 1 which contains at least one compound of the partial formulae Ia or Ib (having two rings) R.sup.1 --A--A.sup.2 --R.sup.2 Ia R.sup.1 --A--Z.sup.1 --A.sup.2 --R.sup.2 Ib Ic and Ii (having three rings) R.sup.1 --A.sup.4 --A--A.sup.2 --R.sup.2 Ic R.sup.1 --A--A.sup.4 --A.sup.2 --R.sup.2 Id R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2 Ie R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --R.sup.2 If R.sup.1 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3 Ig R.sup.3 --A.sup.3 --Z.sup.2 --A--Z.sup.1 --A.sup.2 --R.sup.2 Ih R.sup.1 --A--Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 Ii or Ij to Ip (having four rings) R.sup.1 --A.sup.4 --A--A.sup.2 --A.sup.3 --R.sup.3 Ij R.sup.1 --A--A.sup.4 --A.sup.2 --A.sup.3 --R.sup.3 Ik R.sup.3 --A.sup.3 --Z.sup.2 --A.sup.4 --A--A.sup.2 --R.sup.2 Il R.sup.3 --A.sup.3 --A.sup.4 --A--Z.sup.1 --A.sup.2 --R.sup.2 Im R.sup.1 --A--A.sup.4 --A.sup.2 --Z.sup.2 --A.sup.3 --R.sup.3 In R.sup.1 --A--A.sup.4 --Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3 Io R.sup.1 --A.sup.4 --A--Z.sup.1 --A.sup.2 --A.sup.3 --R.sup.3 Ip
Claim 4
Dependent Claim 19 words
Phase according to claim 1, wherein R 1 , R 2 and R 3 are alkyl, alkoxy or oxaalkyl.
Claim 5
Dependent Claim 29 words
Phase according to claim 1, wherein one of the radicals R 1 , R 2 and R 3 is --CO-alkyl, --O--CO-alkyl, --CO--O-alkyl or CN, and the other is alkyl.
Claim 6
Dependent Claim 33 words
Phase according to claim 1, wherein the alkyl radicals, can have a CH 2 group replaced by an 0 atom, are linear and have 2, 3, 4, 5, 6 or 7 C atoms.
Claim 7
Dependent Claim 24 words
Phase according to claim 1, wherein A 2 , A 3 and A 4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, pyrimidine-2,5-diyl, pyridazine-3,6-diyl, pyridine-2,5-diyl or pyrazine-2,5-diyl.
Claim 8
Dependent Claim 19 words
Phase according to claim 6, wherein A 2 , A 3 and A 4 are independently 1,4-phenylene or pyrimidine-2,5-diyl.
Claim 9
Dependent Claim 29 words
Phase according to claim 1, wherein Z 1 and Z 2 are --O--CO--, --CO--O--, --CH 2 CO--, --COCH 2-- , --CH 2 CH 2 -- or a single bond.
Claim 10
Dependent Claim 14 words
Phase according to claim 8, wherein Z 1 and Z 2 are single bonds.
Claim 11
Dependent Claim 12 words
Phase according to claim 1, wherein Z 0 is a single bond.
Claim 12
Dependent Claim 13 words
Phase according to claim 1, wherein A is a group of formula (A).
Claim 13
Dependent Claim 21 words
Phase according to claim 1 which contains at least compound of the following formulae: ##STR15## wherein r is 0 or 1.
Claim 14
Dependent Claim 50 words
Phase according to claim 1, wherein the substituents R 1 --, R 1 --A 4 --, R 2 --A 2 --Z 1 -- or R 2 --A 2 --Z 1 --A 4 in the 1-position and 4-position of the ring A are in the transconfiguration and assume the equatorial position.
Claim 15
Dependent Claim 52 words
Phase according to claim 1 which contains at least one cyclophexanone derivative of the formula II ##STR16## wherein R 1 is an alkyl group having 1-10 C atoms, q is 0 or 1 and A 4 , Z 1 , A 2 and R 2 have the meaning indicated in formula I.
Claim 16
Dependent Claim 21 words
In a liquid-crystal display device containing a liquid crystal phase, the improvement wherein the phase is one according to claim 1.
Claim 17
Dependent Claim 22 words
In an electrooptical display device containing a liquid crystal dielectric, the improvement wherein the dielectric is a phase according to claim 1.

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