US5045229A
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Difluoromethylene compounds
Assignee: Merck Patent GmbH
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Filing: 1990-03-16
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Granted: 1991-09-03
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Expires: 2010-03-16
Abstract
Abstract Difluoromethylene compounds of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --Q--CF.sub.2 --(A.sup.3 --Z 2 ) n --A 4 --R 2 I in which R 1 , R 2 , A 1 , A 2 , A 3 , A 4 , Z 1 , Z 2 , m and n are as defined herein and Q is --CO--, --O-- or --S--, can be used as components of liquid-crystalline media for liquid-crystal and electrooptical display elements.
Inventors
- 👤 Ekkehard Bartmann
- 👤 Reinhard Hittich
- 👤 Hans-Adolf Kurmeier
- 👤 Eike Poetsch
- 👤 Herbert Plach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 18:10
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3469; C07; C07C; C07C255/00; C07C255/01; C07C255/16; C07C255/49; C07C255/56; C07C323/00; C07C323/01; C07C323/02; C07C323/03; C07C323/07; C07C323/50; C07C323/51; C07C323/60; C07C43/00; C07C43/02; C07C43/20; C07C43/225; C07C45/00; C07C45/45; C07C45/46; C07C49/00; C07C49/76; C07C49/80; C07C49/813; C07C49/84; C09K19/08; C09K19/10; C09K19/12; C09K19/20; C09K19/2007; C09K19/28; C09K19/30; C09K19/3001; C09K19/3003; C09K19/3066; C09K19/3068; C09K19/3087; C09K19/3402; C09K2019/0444; C09K2019/0448; C09K2019/3422
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
202 words
A difluoromethylene compound of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --S--CF.sub.2 --R.sup.2 in which R 1 is alkyl or alkenyl of up to 15 C atoms, in each case optionally unsubstituted, monosubstituted by CN or CF 3 , or mono- or poly-substituted by halogen, or optionally having one or two CH 2 groups, in each case independently of one another, replaced by --O--, ##STR41## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in a manner such that O atoms are not linked directly to one another, R 2 is F, Cl or --CN, A 1 and A 2 independently of one another, are (a) trans-1,4-cyclohexylene in which, optionally one or two non-adjacent CH 2 groups may be replaced by --O-- and/or --S--, (b) 1,4-phenylene, in which, optionally, one or two CH groups may be replaced by N, or (c) a radical which is 1,4-cyclohexenylene, 1,3-cyclobutylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, where radicals (a) and (b) may be substituted by one CN or up to four fluorine, A 1 can also be a single bond, Z 1 is --CO--O--, --O--CO--, CH 2 O--, --OCH 2 --, --CH 2 CH 2 --, --CH═CH--, --C═C-- or a single bond, and m is 1, 2 or 3.
Claim 2
Dependent Claim
202 words
A difluoromethylene compound of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --S--CF.sub.2 --R.sup.2 in which R 1 is alkyl or alkenyl of up to 15 C atoms, in each case optionally unsubstituted, monosubstituted by CN or CF 3 , or mono- or poly-substituted by halogen, or optionally having one or two CH 2 groups, in each case independently of one another, replaced by --O--, ##STR41## --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in a manner such that O atoms are not linked directly to one another, R 2 is F, Cl or --CN, A 1 and A 2 independently of one another, are (a) trans-1,4-cyclohexylene in which, optionally one or two non-adjacent CH 2 groups may be replaced by --O-- and/or --S--, (b) 1,4-phenylene, in which, optionally, one or two CH groups may be replaced by N, or (c) a radical which is 1,4-cyclohexenylene, 1,3-cyclobutylene, 1,4-bicyclo(2,2,2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, where radicals (a) and (b) may be substituted by one CN or up to four fluorine, A 1 can also be a single bond, Z 1 is --CO--O--, --O--CO--, CH 2 O--, --OCH 2 --, --CH 2 CH 2 --, --CH═CH--, --C═C-- or a single bond, and m is 1, 2 or 3.
Claim 3
Dependent Claim
18 words
A difluoromethylene compound of claim 1, wherein A 1 and A 2 , independently are trans-1,4-cyclohexylene or 1,4-phenylene.
Claim 4
Dependent Claim
25 words
A difluoromethylene compound of claim 1, wherein Z 1 and Z 2 , independently are --CH 2 CH 2 --, --C.tbd.C-- or a single bond.
Claim 5
Dependent Claim
17 words
A liquid-crystalline medium having at least two liquid-crystalline components, comprising at least one compound of claim 1.
Claim 6
Dependent Claim
21 words
In a liquid-crystal display element comprising a liquid crystal medium, the improvement wherein the liquid-crystalline medium is one of claim 4.
Claim 7
Dependent Claim
22 words
In an electrooptical display element comprising a liquid crystal dielectric, the improvement wherein the dielectric is a liquid-crystalline medium of claim 4.
Claim 8
Dependent Claim
30 words
A difluoromethylene compound according to claim 1 of the formulae Ia or Ib: R.sup.1 --A.sup.1 --A.sup.2 --X--R.sup.2 Ia R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --X--R.sup.2 Ib wherein X is S--CF 2 .
Claim 9
Dependent Claim
42 words
A difluoromethylene compound according to claim 1 of the formulae R.sup.1 --A.sup.1 --A.sup.1 --A.sup.2 --X--R.sup.2 Id R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --X--R.sup.2Ie R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --A.sup.2 --X--R.sup.2If or R.sup.1 --A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --X--R.sup.2Ig wherein X is S--CF 2 .
Claim 10
Dependent Claim
81 words
A difluoromethylene compound according to claim 1 of the formulae R.sup.1 --A.sup.1 --A.sup.1 --A.sup.1 --A.sup.2 --X--R.sup.2Il R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --A.sup.1 --A.sup.2 --X--R.sup.2Im R.sup.1 --A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --A.sup.2 --X--R.sup.2In R.sup.1 --A.sup.1 --A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --X--R.sup.2Io R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --A.sup.2 --X--R.sup.2 Ip R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --X--R.sup.2 Iq R.sup.1 --A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --X--R.sup.2 Ir or R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --Z.sup.1 --A.sup.1 --Z.sup.2 --A.sup.2 --X--R.sup.2 Is wherein X is S--CF 2 .
Claim 11
Dependent Claim
66 words
A difluoromethylene compound according to claim 7 of the formulae R.sup.1 --Phe--Phe--X--R.sup.2 Iaa R.sup.1 --Phe--Cyc--X--R.sup.2 Iab R.sup.1 --Dio--Phe--X--R.sup.2 Iac R.sup.1 --Pyr--Phe--X--R.sup.2 Iad R.sup.1 --Pyd--Phe--X--R.sup.2 Iae R.sup.1 --Cyc--Phe--X--R.sup.2 Iaf R.sup.1 --Cyc--Cyc--X--R.sup.2 Iag or R.sup.1 --Che--Phe--X--R.sup.2 Iah wherein Phe is unsubstituted 1,4-phenylene or 1,4-phenylene which mono- or disubstituted by F or CN, Cyc is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl, Pyd is pyridine-2,5-diyl, Pyr is pyrimidine-2,5-diyl and Che is 1,4-cyclohexenylene.
Claim 12
Dependent Claim
107 words
A difluoromethylene compound according to claim 7, of the formulae R.sup.1 --Phe--CH.sub.2 CH.sub.2 --Phe--X--R.sup.2 Iba R.sup.1 --Phe--OCH.sub.2 --Phe--X--R.sup.2 Ibb R.sup.1 --Cyc--CH.sub.2 CH.sub.2 --Phe--X--R.sup.2 Ibc R.sup.1 --Cyc--CH.sub.2 --CH.sub.2 --Cyc--X--R.sup.2 Ibd R.sup.1 --Cyc--COO--Phe--X--R.sup.2 Ibe R.sup.1 --Cyc--COO--Cyc--X--R.sup.2 Ibf R.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --Phe--X--R.sup.2 Ibg R.sup.1 --A.sup.1 --CH.sub.2 CH.sub.2 --Cyc--X--R.sup.2 Ibh R.sup.1 --A.sup.1 --CH.sub.2 O--Phe--X--R.sup.2 Ibi R.sup.1 --A.sup.1 --OCH.sub.2 --Phe--X--R.sup.2 Ibj R.sup.1 --A.sup.1 --COO--Phe--X--R.sup.2 Ibk R.sup.1 --A.sup.1 --OCO--Phe--X--R.sup.2 Ibl or R.sup.1 --Che--CH.sub.2 CH.sub.2 --Phe--X--R.sup.2 Ibm wherein X is S--CF 2 , Phe is unsubstituted 1,4-phenylene or 1,4-phenylene which mono- or disubstituted by F or CN, Cyc is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl, Pyd is pyridine-2,5-diyl, Pyr is pyrimidine-2,5-diyl and Che is 1,4-cyclohexenylene.
Claim 13
Dependent Claim
85 words
A difluoromethylene compound to claim 8 of the formulae R.sup.1 --Phe--Phe--Phe--X--R.sup.2 Ida R.sup.1 --Phe--Phe--Cyc--X--R.sup.2 Idb R.sup.1 --Phe--Dio--Phe--X--R.sup.2 Idc R.sup.1 --Cyc--Cyc--Phe--X--R.sup.2 Idd R.sup.1 --Cyc--Cyc--Cyc--X--R.sup.2 Ide R.sup.1 --Pyd--Phe--Phe--X--R.sup.2 Idf R.sup.1 --Pyr--Phe--Phe--X--R.sup.2 Idg R.sup.1 --Phe--Pyr--Phe--X--R.sup.2 Idh R.sup.1 --Cyc--Phe--Phe--X--R.sup.2 Idi R.sup.1 --Cyc--Phe--Cyc--X--R.sup.2 Idj R.sup.1 --Dio--Phe--Phe--X--R.sup.2 Idk R.sup.1 --Che--Phe--Phe--X--R.sup.2 Idl or R.sup.1 --Phe--Che--Phe--X--R.sup.2 Idm wherein X is S--CF 2 , Phe is unsubstituted 1,4-phenylene or 1,4-phenylene which mono- or disubstituted by F or CN, Cyc is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl, Pyd is pyridine-2,5-diyl, Pyr is pyrimidine-2,5diyl and Che is 1,4-cyclohexenylene.
Claim 14
Dependent Claim
14 words
A difluoromethylene compound according to claim 7 in which X--R is --S--CF 3 .
Claim 15
Dependent Claim
15 words
A difluoromethylene compound according to claim 7 in which X--R 2 is --S--CF 2 --Cl.
Claim 16
Dependent Claim
15 words
A difluoromethylene compound according to claim 7 in which X--R 2 is --S--CF 2 --CN.
Claim 17
Dependent Claim
30 words
A difluoromethylene compound according to claim 1 of the formulae ##STR42## in which alkyl- and alkoxy are in each case alkyl or alkoxy groups having 1 to 12 C atoms.
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