# US 10,501,691 B2 · Piperidine derivatives and liquid-crystalline medium

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,501,691 B2
- Document ID: US10501691B2
- Status: Granted
- Kind: B2
- Application number: 15/668,962
- Filed: 2017-08-04
- Published: 2018-02-08
- Granted: 2019-12-10
- Earliest claimed: 2016-08-05
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Achim Goetz; Rocco Fortte; Martin Engel; Sabrina Maag; Thorsten Kodek
- Web page: https://patentgrep.com/patent/US10501691B2

## CPC

- C09K 19/54: Additives having no specific mesophase {characterised by their chemical composition}
- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C09K 19/3098: {Unsaturated non-aromatic rings, e.g. cyclohexene rings}
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- 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

Disclosed are compounds of the formula I, liquid-crystalline media comprising the compounds of formula I, and the use of these liquid-crystalline media in liquid-crystal displays.

## Claims

### Claim 1

A compound of formula I
where
Sp1 and Sp2 are each independently a flexible linking or bridging group, which does not contain a —CO—group,
A and B are each independently:
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4′-bicyclohexylene, in which one or two nonadjacent CH2 groups are optionally replaced by —O—and/or —S—and in which one or more hydrogen atoms are optionally replaced by F, or
b) 1,4-phenylene or 1,3-phenylene, in which one or two nonadjacent CH groups are optionally replaced by N and in which one or more hydrogen atoms are optionally replaced by L, or
c)
in which one or more hydrogen atoms are optionally replaced by L, and/or one or more double bonds are optionally replaced by single bonds, and/or one or more CH groups are optionally replaced by N,
i and j are each independently 0 or 1,
Z0 is a single bond, —CH2—, —CF2—, —CO—, —O—, —NH—, —NH—(CO)—, —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —COO—, —OCO—, —C2F4—or —CF═CF—,
and
L is the same or different at each instance and is F, Cl, CN or a straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, arylalkyl or alkylarylalkyl having 1 to 15 carbon atoms, in which one or more nonadjacent CH2 groups are optionally replaced by —O—and/or —S—,
with the proviso that the following compound is not included

### Claim 2

A compound of formula I
where
Sp1 and Sp2 are each independently alkylene having 1 to 12 carbon atoms which is optionally mono or polysubstituted by F, Cl or CN, and in which one or more nonadjacent CH2 groups are optionally each independently replaced by —O—, —S—, —NH, —COO—, —OCO—, —OCO—O—, —CH═CH—or —C≡C—,
A and B are each independently:
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4′-bicyclohexylene, in which one or two nonadjacent CH2 groups are optionally replaced by —O—and/or —S—and in which one or more hydrogen atoms are optionally replaced by F, or
b) 1,4-phenylene or 1,3-phenylene, in which one or two nonadjacent CH groups are optionally replaced by N and in which one or more hydrogen atoms are optionally replaced by L, or
c)
in which one or more hydrogen atoms are optionally replaced by L, and/or one or more double bonds are optionally replaced by single bonds, and/or one or more CH groups are optionally replaced by N,
i and j are each independently 0 or 1,
Z0 is a single bond, —CH2—, —CF2—, —CO—, —O—, —NH—, —NH—(CO)—, —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —COO—, —OCO—, —C2F4—or —CF═CF—,
and
L is the same or different at each instance and is F, Cl, CN or a straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, arylalkyl or alkylarylalkyl having 1 to 15 carbon atoms, in which one or more nonadjacent CH2 groups are optionally replaced by —O—and/or —S—,
with the proviso that the following compound is not included

### Claim 3 (depends on 1)

The compound according to claim 1 which is of formula I-A
where
Sp1 and Sp2 are each independently a flexible linking or bridging group, which does not contain a —CO—group,
and
L1 to L4 are each independently H, F or straight-chain or branched, in each case optionally fluorinated alkyl having 1 to 7 carbon atoms, in which one or more nonadjacent CH2 groups are optionally replaced by —O—.

### Claim 4 (depends on 1)

A method for stabilization of a liquid-crystalline medium, comprising adding to said liquid-crystalline medium the compound according to claim 1.

### Claim 5 (depends on 1)

A process for preparing the compound according to claim 1, comprising a reaction of 4-hydroxy-2,2,6,6-tetramethylpiperidinyloxyl.

### Claim 6 (depends on 1)

A liquid-crystalline medium comprising
a) or more compounds according to claim 1 and
b) one or more mesogenic compounds.

### Claim 7 (depends on 6)

The liquid-crystalline medium according to claim 6, wherein b) comprises one or more compounds of formulae II-1 to II-4
where
R21 is an unsubstituted alkyl radical having 1 to 7 carbon atoms,
R22 is an unsubstituted alkyl radical having 1 to 7 carbon atoms or an unsubstituted alkoxy radical having 1 to 6 carbon atoms,
and
m, n and o are each independently 0 or 1.

### Claim 8 (depends on 6)

The liquid-crystalline medium according to claim 6, which additionally comprises one or more compounds of formula III-3 and/or formula IV
where
Alkoxy, Alkoxy' are independently an alkoxy radical having 1 to 5 carbon atoms,
R41 is an unsubstituted alkyl radical having 1 to 7 carbon atoms or an unsubstituted alkenyl radical having 2 to 7 carbon atoms,
and
R42 is an unsubstituted alkyl radical having 1 to 7 carbon atoms, an unsubstituted alkoxy radical having 1 to 6 carbon atoms or an unsubstituted alkenyl radical having 2 to 7 carbon atoms.

### Claim 9 (depends on 6)

The liquid-crystalline medium according to claim 6, wherein the total concentration of the one or more compounds of the formula I in the overall medium is 5000 ppm or less.

### Claim 10 (depends on 6)

An electrooptical display or electrooptical component comprising a liquid-crystalline medium according to claim 6.

### Claim 11 (depends on 1)

The compound according to claim 1, where B is trans-1,4-cyclohexylene in which one or more nonadjacent CH2 groups are optionally replaced by —O—and/or —S—and in which one or more hydrogen atoms are optionally replaced by F, or 1,4-phenylene in which one or two nonadjacent CH groups are optionally replaced by N and in which one or more hydrogen atoms are optionally replaced by L.

### Claim 12 (depends on 1)

The compound according to claim 1, where Z0 is a single bond, —CF2O—or —COO—.

### Claim 13 (depends on 1)

The compound according to claim 1, where Sp1 and Sp2, in each case independently, are, for example, —(CH2)p1—, —(CH2CH2O)q1—CH2CH2—, —CH2CH2—S—CH2CH2—or —CH2CH2—NH—CH2CH2—, in which p1 is an integer from 1 to 12, and q1 is an integer from 1 to 3.

### Claim 14 (depends on 1)

The compound according to claim 1, which is one of the following compound of formulae I-1 to I-12:

### Claim 15 (depends on 1)

The compound according to claim 1, where i and j are each 0.

### Claim 16 (depends on 1)

The compound according to claim 1, where i and j are each 1.

### Claim 17 (depends on 1)

The compound according to claim 1, where one of i and j is 0 and the other of i and j is 1.

### Claim 18 (depends on 1)

The compound according to claim 1, Sp1 and Sp2 are each independently alkylene having 1 to 12 carbon atoms which is optionally mono or polysubstituted by F, CI or CN, and in which one or more nonadjacent CH2 groups are optionally each independently replaced by —O—, —S—, —NH—, —CH═CH—or —C≡C—.

### Claim 19 (depends on 1)

The compound according to claim 1, where the grouping
is not —C(O)-alkyl-C(O)—.