Partially fluorinated benzene derivatives

• US 5,571,449 A
• Filed: 01/19/1995
• Issued: 11/05/1996
• Est. Priority Date: 05/19/1993
• Status: Expired due to Term

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Plach, Herbert, Eidenschink, Rudolf, Bartmann, Ekkehard
• Primary Examiner(s): KELLY, CYNTHIA HARRIS
• Application Number:
  US08/373,283
• Time in Patent Office: 656 Days
• Field of Search: 252/299.63, 252/299.66, 252/299.6, 252/299.62, 252/299.61, 252/299.65, 252/299.67, 570/144, 560/63, 560/102, 560/108, 568/647, 546/339, 544/224, 544/298
• US Class Current: 252/299.6
• CPC Class Codes: C07C 22/08 containing fluorine
• CPC Class Codes: C07C 25/18 Polycyclic aromatic halogenated hydrocarbons
• CPC Class Codes: C07D 213/26 Radicals substituted by halogen atoms or nitro radicals
• CPC Class Codes: C07D 239/30 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 319/06 not condensed with other rings
• CPC Class Codes: C09K 19/0403 the structure containing one or more specific, optionally substituted ring or ring systems
• CPC Class Codes: C09K 19/12 at least two benzene rings directly linked, e.g. biphenyls
• CPC Class Codes: C09K 19/14 linked by a carbon chain
• 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 19/3402 having oxygen as hetero atom sugars C09K19/0422
• CPC Class Codes: C09K 19/3444 the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
• CPC Class Codes: C09K 19/3469 Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-
• 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
• CPC Class Codes: C09K 2019/3021 Cy-Ph-Ph-Cy
• CPC Class Codes: C09K 2019/3422 the heterocyclic ring being a six-membered ring

Abstract

Partially fluorinated benzene derivatives of the formula I ##STR1## in which R, A¹, A², Z¹, Z², L¹, L² and m are as defined in claim 1, are suitable as components of liquid-crystalline media.

Claims

1. A partially fluorinated benzene compound of formula I ##STR350## wherein R is H, alkyl having 1 to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF₃ or at least monosubstituted by halogen, wherein one or more CH₂ groups can be replaced, in each case independently of one another by --O--, --S--, ##STR351## --CO--, --CO--O--, --O--CO-- or --O--CO--O--, without O atoms being linked directly to one another, or alkenyl having 1 to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF₃ or at least monosubstituted by halogen, wherein one or more CH₂ groups can be replaced, in each case independently of one another, by --O--, --S--, ##STR352## --CO--, --CO--O--, --O--CO-- or --O--CO--O--, without O atoms being linked directly to one another;

A¹ and A² are each, independently of one another,

(a) trans-1,4-cyclohexylene radical in which one or more nonadjacent CH₂ groups can each be replaced by --O-- or --S--,

(b) 1,4-phenylene in which one or two CH groups can 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 radicals of (a) and (b) can be substituted by one or two fluorine atoms;

Z¹ and Z² are each, independently of one another, --CO--O--, --O--CO--, --CH₂ O--, --CH₂ CH₂ --, --CH═

CH--, --C≡

C-- or a single bond, and one of Z¹ and Z² can also be --(CH₂)₄ -- or --CH═

CH--CH₂ CH₂ --;

m is 0, 1 or 2; and

L¹ and L² are each, independently of one another, H or F.

2. A compound according to claim 1, wherein said compound is of the formula ##STR353## in which R, L¹ and L² are as defined.

3. A compound according to claim 1, wherein said compound is of the formula ##STR354## in which R, L¹ and L² are as defined.

4. A compound according to claim 1, wherein said compound is of the formula I6 ##STR355## in which R is as defined.

5. A compound according to claim 1, wherein said compound is of the formula I7 ##STR356## in which R is as defined.

6. A compound according to claim 1, wherein said compound is of the formula I9 ##STR357## in which R is as defined.

7. In a liquid-crystalline medium having at least two liquid-crystalline compounds, the improvement wherein said medium contains at least one compound according to claim 1.

8. In a liquid-crystal display element containing a liquid-crystalline medium, the improvement wherein said display element contains a medium according to claim 7.

9. In an electrooptical display using a liquid-crystal display element, the improvement wherein said display element contains, as a dielectric, a liquid-crystalline medium according to claim 7.

10. A compound according to claim 1, wherein one of Z¹ and Z² is --(CH₂)₄ -- or --CH═

CH--CH₂ CH₂ -- and the other is a single bond.

11. A compound according to claim 1, wherein L¹ and L² are each H.

12. A compound according to claim 1, wherein L¹ is F and L² is H.

13. A compound according to claim 1, wherein L¹ and L² are each F.

14. A compound according to claim 1, wherein said compound is of the formula I12 ##STR358## in which R is as defined.

15. A compound according to claim 1, wherein said compound is of the formula I25 ##STR359## in which R is as defined.

16. A liquid-crystalline medium according to claim 7, wherein said medium contains 1-40 wt. % of compounds of formula I.

17. A liquid-crystalline medium according to claim 7, wherein said medium contains 45-90 wt. % of compounds of formula I.

18. A compound according to claim 1, wherein

A¹ and A² are each independently 1,4-cyclohexylene which is unsubstituted or mono- or disubstituted by F or CN, 1,4-cyclohexenylene, 1,4-phenylene which is unsubstituted or mono- or disubstituted by F or CN, pyrimidine-2,5-diyl, pyridine-2,5-diyl or 1,3-dioxane-2,5-diyl;

Z¹ and Z² are each independently a single bond, --CO--O--, --O--CO-- or --CH₂ CH₂ --; and

R is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, tridecyl, tetradecyl, pentadecyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy, tetradecoxy, vinyl, prop-1-enyl, prop-2-enyl, but-1-enyl, but-2-enyl, but-3-enyl, pent-1-enyl, pent-2-enyl, pent-3-enyl, pent-4-enyl, hex-1-enyl, hex-2-enyl, hex-3-enyl, hex-4-enyl, hex-5-enyl, hept-1-enyl, hept-2-enyl, hept-3-enyl, hept-4-enyl, hept-5-enyl, hept-6-enyl, oct-1-enyl, oct-2-enyl, oct-3-enyl, oct-4-enyl, oct-5-enyl, oct-6-enyl, oct-7-enyl, non-1-enyl, non-2-enyl, non-3-enyl, non-4-enyl, non-5-enyl, non-6-enyl, non-7-enyl, non-8-enyl, dec-1-enyl, dec-2-enyl, dec-3-enyl, dec-4-enyl, dec-5-enyl, dec-6-enyl, dec-7-enyl, dec-8-enyl or dec-9-enyl.