Liquid-crystalline compounds

• US 5,837,162 A
• Filed: 01/30/1997
• Issued: 11/17/1998
• Est. Priority Date: 02/12/1991
• Status: Expired due to Fees

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Hittich, Reinhard, Poetsch, Eike, Pauluth, Detlef, Reiffenrath, Volker, Weber, Georg, Plach, Herbert, Bartmann, Ekkehard, Geelhaar, Thomas
• Primary Examiner(s): Kelly, C. H.
• Application Number:
  US08/790,803
• Time in Patent Office: 656 Days
• Field of Search: 252/299.01, 252/299.63, 252/299.66, 570/144
• US Class Current: 252/299.63
• CPC Class Codes: C07C 17/263 by condensation reactions
• CPC Class Codes: C07C 17/2632 involving an organo-magnesium compound, e.g. Grignard synthesis
• CPC Class Codes: C07C 17/2635 involving a phosphorus compound, e.g. Wittig synthesis
• CPC Class Codes: C07C 17/269 of only halogenated hydrocarbons
• CPC Class Codes: C07C 17/354 by hydrogenation
• CPC Class Codes: C07C 21/18 containing fluorine
• CPC Class Codes: C07C 25/18 Polycyclic aromatic halogenated hydrocarbons
• CPC Class Codes: C07C 25/24 Halogenated aromatic hydrocarbons with unsaturated side chains
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 39/42 containing six-membered aromatic rings and other rings
• CPC Class Codes: C07C 43/1747 containing six membered aromatic rings and other rings
• CPC Class Codes: C07C 43/192 containing halogen
• CPC Class Codes: C07C 43/225 containing halogen
• CPC Class Codes: C07C 63/72 Polycyclic acids
• CPC Class Codes: C07C 69/76 Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C09K 19/12 at least two benzene rings directly linked, e.g. biphenyls
• CPC Class Codes: C09K 19/3003 Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
• CPC Class Codes: C09K 19/3028 in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
• CPC Class Codes: C09K 19/3048 in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
• CPC Class Codes: C09K 2019/0407 containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
• CPC Class Codes: C09K 2019/0444 : characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group

Abstract

Liquid-crystalline compounds of the formula I ##STR1## R is H, an alkyl or alkylene radical, Z¹ and Z are each, independently of one another, --CH₂ CH₂ --, --CH═CH--,--C.tbd.C-- or a single bond, and one of the radicals Z¹ and Z is alternatively --(CH₂)₄ -- or --CH═CH--CH₂ CH₂ --,

A is trans-1,4-cyclohexylene in which, in addition, one or two non-adjacent CH₂ groups may be replaced by --O--,

A¹ is trans-1,4-cyclohexylene in which, in addition, one or two non-adjacent CH₂ groups may be replaced by --O--, or is 1,4-phenylene which is unsubstituted or monosubstituted or disubstituted by fluorine and/or Cl atoms and in which, in addition, one or two CH groups may be replaced by N,

W is --O--,

Q is a single bond,

m, o, s, r and t are as defined below,

Y is F, Cl, OCF₃, CHF₂, OCHF₂ or OCHF, and can be CF₃,

are suitable as components for liquid-crystalline media.

Claims

1. Liquid-crystalline compounds of the formula ##STR525## in which R is H, an alkyl or alkylene radical having 1 to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF₃ or at least monosubstituted by halogen, it also being possible for one or more CH₂ groups in these radicals each to be replaced, independently of one another, by --O--, --s--, --⋄

--, --CO--, --CO--O--, --O--CO-- or --O--CO--O-- in such a way that oxygen atoms are not linked directly to one another,

Z¹ and Z are each, independently of one another, --CH₂ CH₂ --, --CH═

CH--, --C.tbd.C-- or a single bond, and one of the radicals Z¹ and Z is alternatively --(CH₂)₄ -- or --CH═

CH-- CH₂ CH₂ --,

A is trans-1,4-cyclohexylene in which, in addition, one or two non-adjacent CH₂ groups may be replaced by --O--,

A¹ is trans-1,4-cyclohexylene in which, in addition, one or two non-adjacent CH₂ groups may be replaced by --O--, or is 1,4-phenylene which is unsubstituted or monosubstituted or disubstituted by fluorine and/or Cl atoms and in which, in addition, one or two CH groups may be replaced by N,

m is 0, 1, 2or 3,

o and s are each 0, 1 or 2, where (s+o) is≧

2,

W is --O--,

Q is a single bond,

r is 1 to 7,

t is 0 to 7, and

Y is F, Cl, OCF₃, CHF₂, OCHF₂ or OCHF, and where r+t≧

2, Y can be CF₃.

2. Compounds of the formula IA ##STR526## in which n is 0 to 7, D is --O--, --CH═

CH-- or a single bond, a is 1 to 5, b is 0 and Z, A, o, r and s are as defined in claim 1.

3. Compounds of the formula Ia ##STR527## in which a is 1 to 5, b is 0, s is 1 or 2, and A, Z, o and r are as defined in claim 1.

4. Compounds of the formula Ib ##STR528## in which n is 1 to 7, s is 1 or 2, b is 0, and A, Z, o and r are as defined in claim 1.

5. Compounds of the formula Ib according to claim 4, characterized in that s=2 and Z is a single bond.

6. Compounds of the formula Ib according to claim 4, characterized in that Z is a single bond.

7. Compounds of the formula Ib according to claim 5, characterized in that Z is --(CH₂)₂ --.

8. Compounds of the formula Ib according to claim 5, characterized in that Z is --(CH₂)₄ --.

9. A method of using compounds of formula I of claim 1 which comprises incorporating a compound of formula I as a component of liquid-crystalline media.

10. Liquid-crystalline medium having at least two liquid-crystalline components, characterized in that it contains at least one compound of the formula I of claim 1.

11. Liquid-crystal display elements, characterized in that it contains a liquid-crystalline medium according to claim 10.

12. Electro-optical display element, characterized in that it contains, as dielectric, a liquid-crystalline medium according to claim 10.