# US 5,705,095 A · Partially fluorinated benzene derivatives

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- Number: US 5,705,095 A
- Document ID: US5705095A
- Status: Granted
- Kind: A
- Application number: 08/600,107
- Filed: 1996-02-12
- Granted: 1998-01-06
- Earliest claimed: 1995-02-11
- Assignees: Merck Patent GmbH
- Inventors: Ekkehard Bartmann; Ulrich Finkenzeller
- Web page: https://patentgrep.com/patent/US5705095A

## CPC

- C07C 43/174: containing six-membered aromatic rings
- C07C 43/1742: {with halogen atoms bound to the aromatic rings}
- C07C 43/1747: {containing six membered aromatic rings and other rings}
- C09K 19/0403: {the structure containing one or more specific, optionally substituted ring or ring systems}
- C09K 19/12: at least two benzene rings directly linked, e.g. biphenyls
- C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)}
- C09K 19/3028: {in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds}
- C09K 19/3098: {Unsaturated non-aromatic rings, e.g. cyclohexene rings}
- C09K 19/3444: {the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine}
- C09K 19/3469: {Pyrimidine with a specific end-group other than alkyl, alkoxy or -C*-}
- C07C 2601/14: The ring being saturated
- C07C 2601/16: the ring being unsaturated
- C09K 2019/0407: {containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone}
- 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}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

Compounds of the formula I ##STR1## in which R.sup.1, R.sup.2, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2, L.sup.1, L.sup.2, L.sup.3, m and n are as defined herein, are suitable as component of liquid-crystalline media.

## Claims

### Claim 1

A partially fluorinated benzene compound of the formula I ##STR448## in which R.sup.1 is H, an alkyl or alkenyl radical having 1 to 15 carbon which is unsubstituted, monosubstituted by CN or CF.sub.3, or monosubstituted to perhalo-substituted by halogen, where, optionally, one or more CH.sub.2 groups in these radicals may each independently of one another be replaced by --O--, --S--, ##STR449## --CO--, --CO--O--, --O--CO--or --O--CO--O in such a way that O atoms are not linked directly to one another,
A.sup.1 and A.sup.2 are each, independently of one another,
(a) a trans-1,4-cyclohexylene radical in which, optionally, one or more non-adjacent CH.sub.2 groups may be replaced by --O-- and/or --S--,
(b) a 1,4-phenylene radical in which, optionally, one or two CH groups may be replaced by N,
(c) a radical from the group consisting of 1,4-cyclohexenylene, 1,4-bicyclo›2.2.2!octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1, 2, 3, 4-tetrahydronaphthalene-2,6-diyl,
where the radicals (a) and (b) may further optionally be substituted by one or two fluorine atoms,
Z.sup.1 and Z.sup.2 are each, independently of one another, --CO--O--, --O--CO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --C.tbd.C--, --(CH).sub.4 --, --CH.dbd.CH--CH.sub.2 CH.sub.2 -- or a single bond,
m is 0, 1 or 2,
n is 0 or 1,
L.sup.1, L.sup.2 and L.sup.3 are each, independently of one another, H or F, and
R.sup.2 is an alkyl radical having 1 to 6 carbon atoms which is unsubstituted or substituted by one or more fluorine atoms.

### Claim 2 (depends on 1)

The compound of claim 1, which is a compound of the formula I1 ##STR450## wherein R.sup.1, L.sup.1, L.sup.2 and R.sup.2 are as defined.

### Claim 3 (depends on 1)

The compound of claim 1, which is a compound of the formula I3 ##STR451## wherein R.sup.1, L.sup.1, L.sup.2 and R.sup.2 are as defined.

### Claim 4 (depends on 1)

The compound of claim 1, which is a compound of the formula ##STR452## in which R.sup.1, R.sup.2, L.sup.1, L.sup.2 and L.sup.3 are as defined.

### Claim 5 (depends on 1)

A compound of claim 1, wherein R.sup.2 is --CF.sub.3, --CH.sub.2 CF.sub.3, --CH.sub.2 CHF.sub.2, --CH.sub.2 CH.sub.2 F, --CF.sub.2 CHF.sub.2, --CF.sub.2 CH.sub.2 F, --CHFCF.sub.3, --CF.sub.2 CF.sub.3, --CH.sub.2 --CF.sub.2 --CHF.sub.2, --CH.sub.2 C.sub.2 F.sub.5, --CHFCHF.sub.2, --C.sub.2 H.sub.5 or C.sub.3 H.sub.7.

### Claim 6 (depends on 1)

A liquid-crystalline medium comprising at least two liquid-crystalline components, wherein at least one component is a compound of the formula I of claim 1.

### Claim 7 (depends on 6)

A liquid-crystal display element, comprising a liquid-crystalline medium according to claim 6.

### Claim 8 (depends on 6)

A electrooptical display element, comprising, as dielectric, a liquid-crystalline medium according to claim 6.

### Claim 9 (depends on 7)

The liquid-crystal display element of claim 7, wherein the display is based on the principle of the twisted cell, the guest-host effect, the effect of deformation of aligned phases or the effect of dynamic scattering.

### Claim 10 (depends on 1)

A compound of claim 1 selected from one of the subformulae Ia to IK:
R.sup.1 --A.sup.2 --A.sup.4 --CHF--O--R.sup.2 Ia
R.sup.1 --A.sup.2 --Z.sup.2 --A.sup.4 --CHF--O--R.sup.2 Ib
R.sup.1 --A.sup.1 --A.sup.2 --A.sup.4 --CHF--O--R.sup.2 Ic
R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --A.sup.4 --CHF--O--R.sup.2Id
R.sup.1 --A.sup.1 --A.sup.2 --Z.sup.2 --A.sup.4 --CHF--O--R.sup.2Ie
R.sup.1 --A.sup.1 --A.sup.3 --A.sup.4 --CHF--O--R.sup.2 If
R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.3 --A.sup.4 --CHF--O--R.sup.2Ig
R.sup.1 --A.sup.1 --A.sup.2 --A.sup.3 --A.sup.4 --CHF--O--R.sup.2Ih
R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --A.sup.3 --A.sup.4 --CHF--O--R.sup.2Ii
R.sup.1 --A.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --A.sup.4 --CHF--O--R.sup.2Ij
R.sup.1 --A.sup.1 --Z.sup.1 --A.sup.2 --Z.sup.2 --A.sup.3 --A.sup.4 --CHF--O--R.sup.2 Ik
wherein R.sup.1, A.sup.1, A.sup.2, Z.sup.1, Z.sup.2 and R.sup.2 are defined,
A.sup.3 is ##STR453## A.sup.4 is ##STR454## where L.sup.1, L.sup.2 and L.sup.3 are as defined.

### Claim 11 (depends on 10)

A compound of claim 10, wherein A.sup.1 and A.sup.2 are each independently 1,4-cyclohexyl optionally mono- or di-substituted by F or CN, 1,4-cyclohexylene, 1,4-phenylene optionally mono- or di-substituted by F or CN, pyrimidine-2,5-diyl, pyridine-2,5-diyl or 1,3-dioxane-2,5-diyl.

### Claim 12 (depends on 1)

A compound of claim 1, wherein A.sup.1 and A.sup.2 are independently ##STR455##

### Claim 13 (depends on 1)

A compound of claim 1, wherein each of Z.sup.1 and Z.sup.2 are independently a single bond, --CO--O--, --O--CO-- or --CH.sub.2 CH.sub.2 --.

### Claim 14 (depends on 1)

A compound of claim 1, wherein m+n=1.

### Claim 15 (depends on 1)

A compound of claim 1, wherein R.sup.1 is alkyl or alkoxy of 2 to 7 carbon atoms.

### Claim 16 (depends on 6)

A medium of claim 6, wherein the medium contains 1 to 40% by weight of compounds of the formula I.

### Claim 17 (depends on 6)

A medium of claim 6, wherein the medium contains 45 to 90% by weight of compounds of the formula I.

### Claim 18

A compound of the formula ##STR456## in which Hal is Cl or Br,
X is Cl or F,
L.sup.2 is H or F, and
R.sup.2 is an alkyl radical having 1 to 6 carbon atoms which is unsubstituted or substituted by one or more fluorine atoms.