Fluorobenzene derivatives and liquid-crystalline medium
AssigneeMerck Patent GmbH
InventorsVolker Reiffenrath, Hans A. Kurmeier, Eike Poetsch, Herbert Plach, Ulrich Finkenzeller, Ekkehard Bartmann, Joachim Krause, Bernhard Scheuble
Life of this patent
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Abstract
Fluorobenzene derivatives of the formula I, ##STR1## R, A1, A2, S1, 22, L, m, Y, Q are as defined herein.
Claims36
A liquid-crystals medium comprising at least two liquid-crystalline components, wherein at least one component is a fluorobenzene compound of the formula I, ##STR276## in which R is H or allyl or 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN or CF.sub.3 and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR277## in such a manner that O atoms are not linked directly to one another, A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- wherein only one of A.sup.1 and A.sup.2 is Phe in which Phe is 1,4-phenylene which is unsubstituted or mono- or disubstituted by F or Cn, it being possible for the radicals (a) and (b) to be substituted by CN or fluorine,
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --,
- L is F,
- m is 0, 1 or 2,
- Y is F or Cl, and
- Q is a single bond;
- and
- wherein said medium contains 45-90 wt. % of compounds of formula I.
A fluorobenzene compound of formula Ii
- R--A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --A.sup.3 --Q--Y Ii,
- wherein
- R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN, CF.sub.3 or halogen and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR281## in such a manner that O atoms are not linked directly to one another;
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine,
- wherein only one of A.sup.1 and A.sup.2 is Phe in which Phe is 1,4-phenylene which is unsubstituted or mono- or disubstituted by F or CN:
- A.sup.3 is ##STR282## Z.sup.1 is --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, a single bond, --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --;
- L is F;
- Y is F or Cl;
- and
- Q is a single bond.
A fluorobenzene compound of formula Il
- R--A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --Q--YIl,
- wherein
- R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN, CF.sub.3 or halogen and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR283## in such a manner that O atoms are not linked directly to one another;
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine,
- wherein only one of A.sup.1 and A.sup.2 is Phe in which Phe is 1,4-phenylene which is unsubstituted or mono- or disubstituted by F or CN;
- A.sup.3 is ##STR284## Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--;
- --C.tbd.C-- or a single bond, one of the radicals Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --,
- L is F;
- Y is F or Cl;
- and
- Q is a single bond.
A fluorobenzene compound of the formula I, ##STR285## wherein R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN or CF.sub.3 and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR286## in such a manner that O atoms are not linked directly to one another;
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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, it being possible for the radicals (a) and (b) to be substituted by CN or fluorine, wherein at least one of A.sup.1 and A.sup.2 is 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, or 3,5-difluoro-1,4-phenylene, and wherein only one of A.sup.1 and A.sup.2 is Phe in which Phe is 1,4-phenylene which is unsubstituted or mono- or disubstituted by F or CN;
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 Ch.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of the radicals Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --;
- L is F;
- m is 0, 1 or 2;
- Y is F or Cl;
- and
- Q is a single bond.
A fluorobenzene compound of the formula I, ##STR287## wherein R is straight-chain oxaalkyl or 2-9 C atoms,
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine,
- wherein only one of A.sup.1 and A.sup.2 is Phe in which Phe is 1,4-phenylene which is unsubstituted or mono- or disubstituted by F or CN;
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 Ch.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of the radicals Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --Ch.dbd.CH--CH.sub.2 CH.sub.2 --;
- L is F;
- m is 0, 1 or 2;
- Y is F or Cl;
- and
- Q is a single bond.
A fluorobenzene compound of the formula I, ##STR288## wherein R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN, CF.sub.3 or halogen and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR289## in such a manner that O atoms are not linked directly to one another;
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine;
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of the radicals Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --, and at least one of Z.sup.1 and Z.sup.2 is --C.tbd.C--;
- L is F;
- m is 0, 1 or 2;
- Y is F or Cl;
- and
- Q is a single bond.
A liquid-crystalline medium comprising at least two liquid-crystalline components, wherein at least one component is a fluorobenzene compound of the formula I, ##STR290## in which R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN or CF.sub.3 and in which one or more CH.sub.2 groups can be replaced, in each case, independently of one another, by ##STR291## in such a manner that O atoms are not linked directly to one another, A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine,
- wherein at least one of A.sup.1 and A.sup.2 is trans-1,4-cyclohexylene in which one or more nonadjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 C.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --,
- L is F,
- m is 0, 1 or 2,
- Y is F or Cl, and
- Q is a single bond;
- and
- wherein said medium contains 45-90 wt. % of compounds of formula I.
A liquid-crystalline medium comprising at least two liquid-crystalline components, wherein at least one component is a fluorobenzene compound of the formula I, ##STR292## in which R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN or CF.sub.3 and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR293## in such a manner that O atoms are not linked directly to one another, A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine.
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --,
- L is F,
- m is 0, 1 or 2,
- Y is F or Cl, and
- Q is a single bond;
- and
- wherein said medium contains 45-90 wt. % of compounds of formula I.
A fluorobenzene compound of formula Ii
- R--A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --A.sup.3 --Q--Y Ii,
- wherein
- R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN, CF.sub.3 or halogen and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR294## in such a manner that O atoms are not linked directly to one another;
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine;
- A.sup.3 is ##STR295## Z.sup.1 is --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 13 , --CH.dbd.CH--, --C.tbd.C--, a single bond, --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --;
- L is F;
- Y is F or Cl;
- and
- Q is a single bond.
A fluorobenzene compound of formula I1
- R--A.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --Q--YI1,
- wherein
- R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN, CF.sub.3 or halogen and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR296## in such a manner that O atoms are not linked directly to one another;
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 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,
- it being possible for the radical (a) and (b) to be substituted by CN or fluorine;
- A.sup.3 is ##STR297## Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.CH--;
- --C.tbd.C-- or a single bond, one of the radicals Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --,
- L is F;
- Y is F or Cl;
- and
- Q is a single bond.
A fluorobenzene compound of the formula I, ##STR298## wherein R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN or CF.sub.3 and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR299## in such a manner that O atoms are not linked directly to one another;
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- (b) 1,4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 1,4-bicyclo(2.2.2)octylene, piperidine-1,4-diyl, napthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine, wherein at least one of A.sup.1 land A.sup.2 is 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, or 3,5-difluoro-1,4-phenylene;
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of the radicals Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --;
- L is F;
- m is 0, 1 or 2;
- Y is F or Cl;
- and
- Q is a single bond.
A fluorobenzene compound according to claim 52, wherein said compound is of formula Ife
- R--Phe--Phe--A.sup.3 --Q--Y
- wherein
- R is H or alkyl of 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN or CF.sub.3 and in which one or more CH.sub.2 groups can be replaced, in each case independently of one another, by ##STR300## in such a manner that O atoms are not linked directly to one another;
- Phe is 1,4-phenylene which is unsubstituted or mono- or disubstituted by F or CN;
- A.sup.3 is ##STR301## A is a single bond;
- L is F;
- and
- Y is F or Cl.
A fluorobenzene compound of the formula I, ##STR302## wherein R is straight-chain oxaalkyl of 2-9 C atoms,
- A.sup.1 and A.sup.2, in each case independently of one another, are a
- (a) trans-1,4-cyclohexylene in which one or more non-adjacent CH.sub.2 groups can also be replaced by --O-- and/or --S--,
- 1. 4-phenylene in which one or two CH groups can also be replaced by N,
- (c) 1,4-cyclohexenylene, 1,4-bicyclo(2.2.2)octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6idyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl,
- it being possible for the radicals (a) and (b) to be substituted by CN or fluorine;
- Z.sup.1 and Z.sup.2, in each case independently of one another, are --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.dbd.CH--, --C.tbd.C-- or a single bond, one of the radicals Z.sup.1 and Z.sup.2 can also be --(CH.sub.2).sub.4 -- or --CH.dbd.CH--CH.sub.2 CH.sub.2 --;
- L is F;
- m is 0, 1 or 2;
- Y is F or Cl, and
- Q is a single bond.
Dependencies are inferred from the claim text.