# US 8,465,672 B2 · Tetrahydropyran compounds

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- Number: US 8,465,672 B2
- Document ID: US8465672B2
- Status: Granted
- Kind: B2
- Application number: 12/377,820
- Filed: 2007-07-17
- Published: 2011-10-20
- Granted: 2013-06-18
- Earliest claimed: 2006-08-18
- Assignees: Merck Patent GmbH
- Applicants: Lars Lietzau; Markus Czanta; Atsutaka Manabe
- Inventors: Lars Lietzau; Markus Czanta; Atsutaka Manabe
- Web page: https://patentgrep.com/patent/US8465672B2

## CPC

- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C07D 309/04: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K 2323/03: Viewing layer characterised by chemical composition
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The invention relates to mesogenic tetrahydropyran compounds having at least four rings, of the formula I in which R1, A1, A2, X1, L1, L2, m and n have the meanings indicated in Claim 1, and to a process for the preparation thereof, to the use thereof in liquid-crystalline media, to liquid-crystalline media comprising at least one compound of the formula I, and to electro-optical displays containing a liquid-crystalline medium of this type.

## Claims

### Claim 1

A tetrahydropyran compound of formula I
in which
R1 and X1 denote H, an unsubstituted or mono- or poly-halogen-sub-stituted alkyl or alkoxy radical having 1 to 15 carbon atoms or alkenyl or alkenyloxy radical having 2 to 15 carbon atoms, in which one or more CH2 groups are optionally each, independently of one another, replaced by —C≡C—, —CH═CH—, —CF═CF—, —O —, —(CO)O—or —O(CO)— in such a way that O atoms are not linked directly to one another; or one of the radicals R1 and X1 also denotes F, Cl, CN, NCS or SF5,
rings A1 and A2 denote, independently of one another, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-cyclohexadienylene, which are unsubstituted or substituted by 1 to 3 F,
L1 and L2 denote, independently of one another, H or F,
m denotes 0 or 1 and
n denotes 1, 2 or 3,
where m+n is≧2.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein rings A1 and A2, independently of one another, denote 1,4-cyclohexylene or 1,4-cyclohexenylene.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein n denotes 1.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein R1 denotes alkyl, alkoxy, alkenyl or alkenyloxy having up to 8 carbon atoms.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein X1 denotes F, Cl, CN, NCS, SF5, a halogenated alkyl radical, halogenated alkoxy radical, halogenated alkenyl radical or halogenated alkenyloxy radical, each having up to 7 C atoms.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein L1 denotes fluorine and L2 denotes fluorine or hydrogen.

### Claim 7 (depends on 1)

A compound according to claim 1, wherein L1 and L2 denote fluorine.

### Claim 8 (depends on 1)

A compound according to claim 1, which is one of formulae I1 to I30
where
R1 denotes H, F, Cl, CN, NCS or SF5, or an unsubstituted or mono- or poly- halogen-substituted alkyl or alkoxy radical having 1 to 15 carbon atoms or alkenyl or alkenyloxy radical having 2 to 15 carbon atoms, in which one or more CH2 groups are optionally each, independently of one another, replaced by —C≡C—, —CH═CH—, —CF═CF—, —O—, —(CO)O— or —O(CO)—in such a way that O atoms are not linked directly to one another.

### Claim 9 (depends on 1)

A compound according to claim 1, wherein the substituents on the tetrahydropyran ring in the 1,4-position are in the trans-position to one another.

### Claim 10 (depends on 1)

A process for preparing a compound according to claim 1, comprising reacting a cyclohexanone of formula II
in which
R1, A1, A2 and m are as defined in formula I, and
p denotes 0, 1 or 2,
with an arylmetal compound of formula III
in which
L1, L2 and X1 are as defined in formula I, and
M denotes Li, MgCI or MgBr.

### Claim 11 (depends on 1)

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

### Claim 12 (depends on 11)

An electro-optical device, containing a liquid-crystalline medium according to claim 11.

### Claim 13 (depends on 11)

An electro-optical liquid-crystal display, containing a liquid-crystalline medium according to claim 11.

### Claim 14 (depends on 13)

A method of generating an electro-optical effect comprising applying a voltage to a display according to claim 13.

### Claim 15 (depends on 12)

A method of generating an electro-optical effect comprising applying a voltage to a device according to claim 12.

### Claim 16 (depends on 1)

A compound according to claim 1, which is

### Claim 17 (depends on 1)

A compound according to claim 1, which is a compound of the following formula
wherein
R1
X1
L1
L2
H
F
H
H
CH3
F
H
H
C2H5
F
H
H
n-C3H7
F
H
H
n-C4H9
F
H
H
n-C5H11
F
H
H
n-C6H13
F
H
H
H
F
F
H
CH3
F
F
H
C2H5
F
F
H
n-C3H7
F
F
H
n-C4H9
F
F
H
n-C5H11
F
F
H
n-C6H13
F
F
H
H
F
F
F
CH3
F
F
F
C2H5
F
F
F
n-C3H7
F
F
F
nC4H9
F
F
F
n-C5H11
F
F
F
n-C6H13
F
F
F
H
OCF3
H
H
CH3
OCF3
H
H
C2H5
OCF3
H
H
n-C3H7
OCF3
H
H
n-C4H9
OCF3
H
H
n-C5H11
OCF3
H
H
n-C6H13
OCF3
H
H
H
OCF3
F
H
CH3
OCF3
F
H
C2H5
OCF3
F
H
n-C3H7
OCF3
F
H
n-C4H9
OCF3
F
H
n-C5H11
OCF3
F
H
n-C6H13
OCF3
F
H
H
OCF3
F
F
CH3
OCF3
F
F
C2H5
OCF3
F
F
n-C3H7
OCF3
F
F
nC4H9
OCF3
F
F
n-C5H11
OCF3
F
F
n-C6H13
OCF3
F
F
H
CN
H
H
CH3
CN
H
H
C2H5
CN
H
H
n-C3H7
CN
H
H
n-C4H9
CN
H
H
n-C5H11
CN
H
H
n-C6H13
CN
H
H
H
CN
F
H
CH3
CN
F
H
C2H5
CN
F
H
n-C3H7
CN
F
H
n-C4H9
CN
F
H
n-C5H11
CN
F
H
n-C6H13
CN
F
H
H
CN
F
F
CH3
CN
F
F
C2H5
CN
F
F
n-C3H7
CN
F
F
nC4H9
CN
F
F
n-C5H11
CN
F
F
n-C6H13
CN
F
F
H
OCHF2
H
H
CH3
OCHF2
H
H
C2H5
OCHF2
H
H
n-C3H7
OCHF2
H
H
n-C4H9
OCHF2
H
H
n-C5H11
OCHF7
H
H
n-C6H13
OCHF7
H
H
H
OCHF2
F
H
CH3
OCHF2
F
H
C2H5
OCHF2
F
H
n-C3H7
OCHF2
F
H
n-C4H9
OCHF2
F
H
n-C5H11
OCHF2
F
H
n-C6H13
OCHF2
F
H
H
OCHF2
F
F
CH3
OCHF2
F
F
C2H5
OCHF2
F
F
n-C3H7
OCHF2
F
F
nC4H9
OCHF2
F
F
n-C5H11
OCHF2
F
F
n-C6H13
OCHF2
F
F
H
CF3
H
H
CH3
CF3
H
H
C2H5
CF3
H
H
n-C3H7
CF3
H
H
n-C4H9
CF3
H
H
n-C5H11
CF3
H
H
n-C6H13
CF3
H
H
H
CF3
F
H
CH3
CF3
F
H
C2H5
CF3
F
H
n-C3H7
CF3
F
H
n-C4H9
CF3
F
H
n-C5H11
CF3
F
H
n-C6H13
CF3
F
H
H
CF3
F
F
CH3
CF3
F
F
C2H5
CF3
F
F
n-C3H7
CF3
F
F
nC4H9
CF3
F
F
n-C5H11
CF3
F
F
n-C6H13
CF3
F
F
H
CH3
F
F
CH3
CH3
F
F
C2H5
CH3
F
F
n-C3H7
CH3
F
F
nC4H9
CH3
F
F
n-C5H11
CH3
F
F
n-C6H13
CH3
F
F
H
CH3
F
H
CH3
CH3
F
H
C2H5
CH3
F
H
n-C3H7
CH3
F
H
nC4H9
CH3
F
H
n-C5H11
CH3
F
H
n-C6H13
CH3
F
H
H
CH3
H
H
CH3
CH3
H
H
C2H5
CH3
H
H
n-C3H7
CH3
H
H
nC4H9
CH3
H
H
n-C5H11
CH3
H
H or
n-C6H13
CH3
H
H
or
a compound of the following formula
where
R1
X1
L1
L2
H
F
H
H
CH3
F
H
H
C2H5
F
H
H
n-C3H7
F
H
H
n-C4H9
F
H
H
n-C5H11
F
H
H
n-C6H13
F
H
H
H
F
F
H
CH3
F
F
H
C2H5
F
F
H
n-C3H7
F
F
H
n-C4H9
F
F
H
n-C5H11
F
F
H
n-C6H13
F
F
H
H
F
F
F
CH3
F
F
F
C2H5
F
F
F
n-C3H7
F
F
F
nC4H9
F
F
F
n-C5H11
F
F
F
n-C6H13
F
F
F
H
OCF3
H
H
CH3
OCF3
H
H
C2H5
OCF3
H
H
n-C3H7
OCF3
H
H
n-C4H9
OCF3
H
H
n-C5H11
OCF3
H
H
n-C6H13
OCF3
H
H
H
OCF3
F
H
CH3
OCF3
F
H
C2H5
OCF3
F
H
n-C3H7
OCF3
F
H
n-C4H9
OCF3
F
H
n-C5H11
OCF3
F
H
n-C6H13
OCF3
F
H
H
OCF3
F
F
CH3
OCF3
F
F
C2H5
OCF3
F
F
n-C3H7
OCF3
F
F
nC4H9
OCF3
F
F
n-C5H11
OCF3
F
F
n-C6H13
OCF3
F
F
H
CN
H
H
CH3
CN
H
H
C2H5
CN
H
H
n-C3H7
CN
H
H
n-C4H9
CN
H
H
n-C5H11
CN
H
H
n-C6H13
CN
H
H
H
CN
F
H
CH3
CN
F
H
C2H5
CN
F
H
n-C3H7
CN
F
H
n-C4H9
CN
F
H
n-C5H11
CN
F
H
n-C6H13
CN
F
H
H
CN
F
F
CH3
CN
F
F
C2H5
CN
F
F
n-C3H7
CN
F
F
nC4H9
CN
F
F
n-C5H11
CN
F
F
n-C6H13
CN
F
F
H
OCHF2
H
H
CH3
OCHF2
H
H
C2H5
OCHF2
H
H
n-C3H7
OCHF2
H
H
n-C4H9
OCHF2
H
H
n-C5H11
OCHF2
H
H
n-C6H13
OCHF2
H
H
H
OCHF2
F
H
CH3
OCHF2
F
H
C2H5
OCHF2
F
H
n-C3H7
OCHF2
F
H
n-C4H9
OCHF2
F
H
n-C5H11
OCHF2
F
H
n-C6H13
OCHF2
F
H
H
OCHF2
F
F
CH3
OCHF2
F
F
C2H5
OCHF2
F
F
n-C3H7
OCHF2
F
F
nC4H9
OCHF2
F
F
n-C5H11
OCHF2
F
F
n-C6H13
OCHF2
F
F
H
CF3
H
H
CH3
CF3
H
H
C2H5
CF3
H
H
n-C3H7
CF3
H
H
n-C4H9
CF3
H
H
n-C5H11
CF3
H
H
n-C6H13
CF3
H
H
H
CF3
F
H
CH3
CF3
F
H
C2H5
CF3
F
H
n-C3H7
CF3
F
H
n-C4H9
CF3
F
H
n-C5H11
CF3
F
H
n-C6H13
CF3
F
H
H
CF3
F
F
CH3
CF3
F
F
C2H5
CF3
F
F
n-C3H7
CF3
F
F
nC4H9
CF3
F
F
n-C5H11
CF3
F
F or
n-C6H13
CF3
F
F.

### Claim 18 (depends on 1)

A compound according to claim 1, wherein n denotes 2.

### Claim 19 (depends on 1)

A compound according to claim 1, wherein n denotes 3.