Polymerizable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-11225606-B2
Application number	US-201916400647-A
Country	US
Kind code	B2
Filing date	May 1, 2019
Priority date	Jun 9, 2015
Publication date	Jan 18, 2022
Grant date	Jan 18, 2022

Abstract

The present invention relates to polymerizable compounds, to processes and intermediates for the preparation thereof, to liquid-crystal media comprising them, and to the use of the polymerizable compounds and liquid crystalline media for optical, electro-optical and electronic purposes, in particular in liquid crystalline displays, especially in liquid crystalline displays of the polymer sustained alignment type.

First claim

The invention claimed is:

1. A compound of formula I
P-Sp-Ar-R  I

wherein
Ar is

which is substituted by at least one group L a and optionally substituted by one or more groups L,
L a is an alkoxy group with 1 to 12 C atoms that is straight-chain or branched, with the proviso that L a is not fluorinated,
L is on each occurrence identically or differently F, Cl, —CN, P-Sp-, or straight chain alkyl having 1 to 25 C atoms, or branched or cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl, or L has the meaning of L a ,
P is a polymerizable group consisting of acrylate or methacrylate,
Sp is a spacer group that is a single bond,
R is P-Sp-, H or has one of the meanings given for L,
wherein, if Ar is one of Ar1 to Ar3, all groups P that are present in the compound have the same meaning.

2. The compound according to claim 1 , of the following subformulae

wherein P, L′, L a and Sp are as defined in claim 1 .

3. A liquid crystalline medium comprising one or more polymerizable compounds formula I as defined in claim 1 .

4. The liquid crystalline medium of claim 3 , comprising
a polymerizable component A) comprising one or more polymerizable compounds of formula I, and
a liquid-crystalline liquid crystalline component B) comprising one or more mesogenic or liquid-crystalline compounds.

5. The liquid crystalline medium of claim 3 , comprising one or more compounds of the formulae CY and/or PY:

in which the individual radicals have the following meanings:
a denotes 1 or 2,
b denotes 0 or 1,

denotes

R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or
CO—O— in such a way that 0 atoms are not linked directly to one another,
Z x denotes —CH═CH—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —O—, —CH 2 —, —CH 2 CH 2 — or a single bond, L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, CHF 2 .

6. The liquid crystalline medium according to claim 3 comprising one or more compounds of the following formulae:

in which the individual radicals, on each occurrence identically or differently, each, independently of one another, have the following meaning:

is

is

is

R A1 is alkenyl having 2 to 9 C atoms or, if at least one of the rings X, Y and Z denotes cyclohexenyl, also one of the meanings of R A2 ,
R A2 is alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that 0 atoms are not linked directly to one another,
Z x is —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond,
L 1-4 each, independently of one another, are H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 H,
x is 1 or 2,
z is 0 or 1.

7. The liquid crystalline medium according to claim 3 , comprising one or more compounds of the following formula:

in which the individual radicals have the following meanings:

denotes

denotes

R 3 and R 4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that 0 atoms are not linked directly to one another,
Z y denotes —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF— or a single bond.

8. The liquid crystalline medium according to claim 3 , wherein the polymerizable compounds of formula I are polymerized.

9. A process of preparing an liquid crystalline medium of claim 3 , comprising mixing one or more mesogenic or liquid-crystalline compounds with one or more compounds of formula I and optionally with further liquid-crystalline compounds and/or additives.

10. A liquid crystalline display comprising a liquid crystalline medium as defined in claim 3 .

11. The liquid crystalline display of claim 10 , which is a PSA display.

12. The liquid crystalline display of claim 11 , which is a PS-VA, PS-OCB, PS-IPS, PS-FFS, PS—UB-FFS, PS-posi-VA or PS-TN display.

13. The liquid crystalline display of claim 10 comprising two substrates, at least one which is transparent to light, an electrode provided on each substrate or two electrodes provided on only one of the substrates, and located between the substrates a layer of an liquid crystalline medium, wherein the polymerizable compounds are polymerized between the substrates of the display.

14. A process for the production of a liquid crystalline display according to claim 13 , comprising providing the liquid crystalline medium comprising one or more polymerizable compounds, as defined in claim 7 , between the substrates of the display, and polymerizing the polymerizable compounds.

15. A compound of the following formulae

which is substituted by at least one group L a ,
wherein
L is on each occurrence identically or differently F, Cl, —CN, P-Sp—, or straight

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Schwebel Nico
• Brocke Constanze
• Deing Kaja
• Vogt Julian
• Meyer Elisabeth

Classifications

• C09K19/04 Primary

  characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} · CPC title

• C09K2019/127

  Compounds containing phenylene-1,3-diyl · CPC title

• C09K2019/3425

  Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title

• C09K2019/2078

  Ph-COO-Ph-COO-Ph · CPC title

• C09K19/34

  containing at least one heterocyclic ring · CPC title