Naphthalene compounds for liquid-crystalline mixtures

Patent metadata

Field	Value
Publication number	US-10723951-B2
Application number	US-201615781602-A
Country	US
Kind code	B2
Filing date	Nov 24, 2016
Priority date	Dec 9, 2015
Publication date	Jul 28, 2020
Grant date	Jul 28, 2020

Abstract

The invention relates to compounds of the formula I,

in which

R, A, Z, m, L 1 , L 2 , L 3 and X have the meanings indicated in Claim 1 , to a process for the preparation thereof, and 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.

First claim

The invention claimed is:

1. Compounds of the formula I,

in which
X denotes Cl,
R denotes a halogenated or unsubstituted alkyl radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in the halogenated or unsubstituted alkyl radical having 1 to 15 C atoms may each be replaced, independently of one another, by —C≡C—, —CH═CH—, —(CO)O—, —O(CO)—, —(CO)— or —O— in such a way that O atoms are not linked directly to one another, or a polymerisable radical,
A denotes
a) trans-1,4-cyclohexylene or cyclohexenylene, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and in which H may be substituted by F,
b) 1,4-phenylene, in which one or two CH groups may be replaced by N and in which, in addition, one or more H atoms may be replaced by Br, Cl, F, CN, methyl, methoxy or a mono- or polyfluorinated methyl or methoxy group,

Z denotes a single bond, —CH 2 O—, —(CO)O—, —CF 2 O—, —CH 2 CH 2 CF 2 O—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C— wherein the asymmetrical definitions for Z may be oriented to any of both possible directions,
L 1 , L 2 and L 3 ,
independently of one another, denote H or F, and

m denotes 0 or 1.

2. Compounds according to claim 1 , characterised in that
L 3 denotes F.

3. Compounds according to claim 1 , characterised in that
R denotes alkyl, alkoxy, alkenyl or alkenyloxy having up to 8 carbon atoms or a polymerisable group.

4. Compounds according to claim 1 , characterised in that L 1 denotes fluorine and L 2 denotes H.

5. Compounds according to claim 1 , characterised in that L 1 and L 2 denote H.

6. Compounds according to claim 1 selected from the formulae:

in which R has the meanings indicated in claim 1 .

7. Process for the preparation of compounds of the formula I according to claim 1 , including a process step in which a boronic acid of the formula IIA or an open-chain or cyclic boronic acid ester of the formula IIB,

in which X, L 1 , L 2 and L 3 are defined as in claim 1 , and
R 3 , R 4 denote alkyl having 1-12 C atoms or R 3 +R 4 together also denote alkylene or 1,2-phenylene,
where phenylene, R 3 , R 4 and R 3 +R 4 may also be substituted,

is reacted with a compound of the formula III

in which
Y denotes a group R-(A-Z) m — or OH,
in which R, A, Z and m independently are defined as for formula I and
Hal denotes O(SO 2 )CF 3 , Cl, Br or I,
in the presence of a transition-metal catalyst.

8. The method comprising:
preparing a liquid-crystalline medium comprising at least one compound of the formula I according to claim 1 .

9. A liquid-crystalline medium comprising at least two mesogenic compounds, characterised in that it comprises at least one compound of the formula I according to claim 1 .

10. A method comprising including the liquid-crystalline medium according to claim 9 in an electro-optical device.

11. Electro-optical liquid-crystal display containing a liquid-crystalline medium according to claim 9 .

12. Compounds of the formula I,

in which
X denotes F or Cl,
R denotes a halogenated or unsubstituted alkyl radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in the halogenated or unsubstituted alkyl radical having 1 to 15 C atoms may each be replaced, independently of one another, by —C≡C—, —CH═CH—, —(CO)O—, —O(CO)—, —(CO)— or —O— in such a way that O atoms are not linked directly to one another, or a polymerisable radical,
A denotes
a) trans-1,4-cyclohexylene or cyclohexenylene, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and in which H may be substituted by F,
b) 1,4-phenylene, in which one or two CH groups may be replaced by N and in which, in addition, one or more H atoms may be replaced by Br, Cl, F, CN, methyl, methoxy or a mono- or polyfluorinated methyl or methoxy group,

Z denotes a single bond, —CH 2 O—, —(CO)O—, —CF 2 O—, —CH 2 CH 2 CF 2 O—, —CF 2 CF 2 —, —CH 2 CF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CH═CH—, —CH═CF—, —CF═CF— or —C≡C—, wherein the asymmetrical definitions for Z may be oriented to any of both possible directions,
L 1 , L 2 and L 3 ,
independently of one another, denote H or F, and

m denotes 0 or 1, and
wherein the compounds have liquid crystalline temperature range of at least 146 degrees C.

13. Compounds according to claim 12 , wherein the compounds have an optical anisotropy Δn of at least 0.322.

Assignees

• Merck Patent Gmbh

Inventors

• Jasper Christian
• Gunst Susann
• Haensel Helmut
• Schuler Brigitte

Classifications

• G02F1/13

  based on liquid crystals, e.g. single liquid crystal display cells · CPC title

• C09K19/322 Primary

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K19/12

  at least two benzene rings directly linked, e.g. biphenyls · CPC title

• C09K2019/122

  Ph-Ph · CPC title