# US 7,744,968 B2 · Cyclobutane and spiro[3.3]heptane compounds

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- Number: US 7,744,968 B2
- Document ID: US7744968B2
- Status: Granted
- Kind: B2
- Application number: 12/067,220
- Filed: 2006-08-16
- Published: 2008-08-28
- Granted: 2010-06-29
- Earliest claimed: 2005-09-19
- Assignees: Merck Patent GmbH
- Inventors: Volker Reiffenrath; Matthias Bremer; Melanie Klasen-Memmer
- Web page: https://patentgrep.com/patent/US7744968B2

## CPC

- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K 19/30: containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K 2019/327: {containing a spiro ring system}
- C09K 2323/00: Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The present invention relates to cyclobutane and spiro[3.3]heptane compounds, to a process for the preparation thereof, to the use thereof as components in liquid-crystalline media, and to electro-optical display elements which contain these liquid-crystalline media.

## Claims

### Claim 1

A compound of formula I
in which, in each case independently of one another, identically or differently,
R1 is a group of the formula
R2 is hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl having up to 15 carbon atoms which is unsubstituted or mono- or polysubstituted by F, in which one or more CH2 groups are optionally replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —(CO)O—, —O(CO)— or —O(CO)—O— in such a way that heteroatoms are not linked directly, or a group of the formula
A1, A2, A3 and A4 denote 1,4-cyclohexylene, in which one or two CH2 are optionally replaced by O, 1,4-phenylene, which may be unsubstituted or mono- or disubstituted by F, or a group of the formula
Z1, Z2, Z3 and Z4 denote a single bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —(CO)O—, —O(CO)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
a, b, c and d denote 0, 1 or 2, and
n and m denote 0 or 1.

### Claim 2

A compound of formula I
in which, in each case independently of one another, identically or differently,
R1 and R2 are hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl having up to 15 carbon atoms which is unsubstituted or mono- or polysubstituted by F, in which one or more CH2 groups are optionally replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —(CO)O—, —O(CO)— or —O(CO)—O— in such a way that heteroatoms are not linked directly, or a group of the formula
A1, A2, A3 and A4 denote 1,4-cyclohexylene, in which one or two CH2 are optionally replaced by O, 1,4-phenylene, which may be unsubstituted or mono- or disubstituted by F, or a group of the formula
Z1, Z2, Z3 and Z4 denote a single bond, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
a, b, c and d denote 0, 1 or 2, wherein the sum of a+b+c+d is 1, 2 or 3,
n is 1, and
m is 0 or 1,
wherein at least one of A1, A2, A3 and A4 is a group of the formula

### Claim 3 (depends on 1)

A compound according to claim 1, wherein m and n are 1.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein m and n are 0.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein c and d are 0.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein R2 denotes C1-8-alkoxy or alkenyloxy.

### Claim 7 (depends on 1)

A compound according to claim 1, wherein Z1, Z2, Z3 and Z4, independently of one another, denote a single bond, —CH2O— or —OCH2—.

### Claim 8 (depends on 1)

A process for preparing a compound according to claim 1, comprising converting a terminal alkene at the double bond using trichloroacetyl chloride into a 2,2-dichlorocyclobutan-1-on-3-yl compound.

### Claim 9 (depends on 1)

A liquid-crystalline medium having at least two liquid-crystalline compounds, which comprises at least one compound according claim 1.

### Claim 10 (depends on 9)

An electro-optical display element containing a liquid-crystalline medium according to claim 9.

### Claim 11 (depends on 2)

A compound according to claim 2, wherein c and d are 0.

### Claim 12 (depends on 2)

A compound according to claim 2, wherein R2 denotes C1-8-alkoxy or alkenyloxy.

### Claim 13 (depends on 2)

A compound according to claim 2, wherein Z1, Z2, Z3 and Z4, independently of one another, denote a single bond, —CH2O— or —OCH2—.

### Claim 14

A compound of formula I
in which, in each case independently of one another, identically or differently,
R1 is hydrogen, an alkanyl, alkoxy, alkenyl or alkynyl having up to 15 carbon atoms which is unsubstituted or mono- or polysubstituted by F, in which one or more CH2 groups are optionally replaced, independently of one another, by —O—, —S—, —SO2—, —CO—, —(CO)O—, —O(CO)— or —O(CO)—O— in such a way that heteroatoms are not linked directly, or a group of the formula
R2 is C1-8-alkoxy or alkenyloxy
A1, A2, A3 and A4 denote 1,4-cyclohexylene, in which one or two CH2 are optionally replaced by O, 1,4-phenylene, which may be unsubstituted or mono- or disubstituted by F, or a group of the formula
Z1, Z2, Z3 and Z4 denote a single bond, —CF2O—, —OCF2—, —CH2CH2—, —CF2CF2—, —CF2CH2—, —CH2CF2—, —CHF—CHF—, —(CO)O—, —O—(CO)—, —CH2O—, —OCH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH═CH— or —C≡C—,
a and b denote 0, 1 or 2,
c and d denote 0,
n is 0 or 1, and
m is 0,
wherein at least one group from R1 and R2 denotes a structural element of the formula
or
at least one group from A1, A2, A3 and A4 denotes a structural element of the formula
and
wherein the total number of rings from R1, R2, A1, A2, A3 and A4 is 2, wherein each spiro[3.3]heptane group counts as one ring.

### Claim 15 (depends on 14)

A compound according to claim 14, wherein n is 1.

### Claim 16 (depends on 14)

A compound according to claim 14, wherein n is 0.

### Claim 17 (depends on 14)

A compound according to claim 14, wherein Z1, Z2, Z3 and Z4, independently of one another, denote a single bond, —CH2O— or —OCH2—.

### Claim 18 (depends on 2)

A liquid-crystalline medium having at least two liquid-crystalline compounds, which comprises at least one compound according claim 2.

### Claim 19 (depends on 14)

A liquid-crystalline medium having at least two liquid-crystalline compounds, which comprises at least one compound according claim 14.