# US 6,723,866 B2 · Liquid-crystalline compounds

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- Number: US 6,723,866 B2
- Document ID: US6723866B2
- Status: Granted
- Kind: B2
- Application number: 10/202,633
- Filed: 2002-07-25
- Published: 2003-11-20
- Granted: 2004-04-20
- Earliest claimed: 2001-07-25
- Assignees: Merck Patent GmbH
- Inventors: Peer Kirsch; Michael Heckmeier; Joachim Krause; Marc Lenges; Gerald Unger
- Web page: https://patentgrep.com/patent/US6723866B2

## CPC

- C09K 19/0403: {the structure containing one or more specific, optionally substituted ring or ring systems}
- C07D 319/06: not condensed with other rings
- C09K 19/20: linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters {or ethers}
- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K 19/322: {Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring}
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- 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}
- C09K 2019/0466: {the linking chain being a -CF2O- chain}
- C09K 2019/326: {containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to liquid-crystalline compounds of the formula I in which R1, A1, A2, Z1, Z2, a, b, L1, L2 and L3 are as defined in claim 1, and to liquid-crystalline media comprising at least compound of the formula I and to electro-optical displays containing a liquid-crystalline medium of this type.

## Claims

### Claim 1

A liquid-crystalline compound of the formula I
in which
R1 is an alkyl radical having from 1 to 15 carbon atoms which is unsubstituted, monosubstituted by CN or CF3 or mono-to per halo-substituted by halogen, where one or more CH2 groups in these radicals are optionally replaced by —O—, —S—, —CH═CH—, —C≡C—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
A1 and A2 are each, independently of one another,
a) a 1,4-cyclohexenylene or 1,4-cyclohexylene radical, in which one or two non-adjacent CH2 groups are optionally replaced by —O— or —S—,
b) a 1,4-phenylene radical, in which one or two CH groups are optionally replaced by N,
c) a radical selected from the group consisting of piperidine-1,4-diyl, 1,4-bicyclo[2.2.2]octylene, phenanthrene-2,7-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,
where the radicals a), b) and c) are optionally monosubstituted or polysubstituted by halogen atoms,
Z1 and Z2 are each, independently of one another, —CO—O—, —O—CO—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CH2CH2—, —(CH2)4—, —C2F4—, —CH2CF2—, —CF2CH2—, —CF═CF—, —CH═CH—, —C≡C— or a single bond, with the proviso that at least one of Z1 and Z2 is —CF2O— or —OCF2—,
a is 0, 1 or 2,
b is 1 or 2, and
L1, L2 and L3 are each, independently of one another, H, F or Cl.

### Claim 2 (depends on 1)

A liquid-crystalline compound according to claim 1, wherein R1 is a straight-chain alkyl radical having from 1 to 10 carbon atoms or an alkenyl radical having from 2 to 10 carbon atoms.

### Claim 3 (depends on 1)

A liquid-crystalline compound according to claim 1, wherein a+b=1 or 2.

### Claim 4 (depends on 2)

A liquid-crystalline compound according to claim 2, wherein a+b=1 or 2.

### Claim 5 (depends on 1)

A liquid-crystalline compound according to claim 1, wherein L1 is fluorine and L2 is fluorine or hydrogen.

### Claim 6 (depends on 2)

A liquid-crystalline compound according to claim 2, wherein L1 is fluorine and L2 is fluorine or hydrogen.

### Claim 7 (depends on 3)

A liquid-crystalline compound according to claim 3, wherein L1 is fluorine and L2 is fluorine or hydrogen.

### Claim 8 (depends on 5)

A liquid-crystalline compound according to claim 5, wherein L2 and L3 are fluorine.

### Claim 9 (depends on 1)

A liquid-crystalline compound of claim 1, which is of one of the formulae I1 to I94:
in which
R1 is as defined in claim 1 and (F) is fluoro or hydrogen.

### Claim 10 (depends on 1)

A liquid-crystalline medium comprising at least two mesogenic compounds, wherein at least one compound is of the formula I according to claim 1.

### Claim 11 (depends on 10)

An electro-optical liquid-crystal display containing a liquid-crystalline, medium according to claim 10.

### Claim 12 (depends on 1)

A compound of claim 1, wherein a=o.

### Claim 13 (depends on 1)

A compound of claim 1, wherein one of Z1 and Z2 is —CF2O— or —OCF2— and the other is a single bond.

### Claim 14 (depends on 10)

A liquid-crystalline medium of claim 10, which exhibits a nematic phase range from −20° C. to above 100° C., a dielectric anisotropy, Δε, ≧4.

### Claim 15 (depends on 10)

A liquid-crystalline medium of claim 10, wherein the proportion of compounds of the formula I is from 5-95% by weight.

### Claim 16 (depends on 1)

A compound of claim 1, wherein R1 is ethyl or propyl.