Polymerizable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-9594283-B2
Application number	US-201514833464-A
Country	US
Kind code	B2
Filing date	Aug 24, 2015
Priority date	Aug 25, 2014
Publication date	Mar 14, 2017
Grant date	Mar 14, 2017

Abstract

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

First claim

The invention claimed is:

1. A compound of formula I

wherein
R denotes P-Sp b -, H or has one of the meanings given for L,
Sp a , Sp b denote, on each occurrence identically or differently, a spacer group or a single bond,
P denotes, on each occurrence identically or differently, a polymerizable group,
L F, Cl, CN, or straight chain, branched or cyclic alkyl having 1 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,
r is 0, 1, 2, 3 or 4,
s is 0, 1, 2 or 3,
wherein at least one of the groups Sp a and Sp b is a single bond and at least one of the groups Sp a and Sp b is different from a single bond.

2. The compound of claim 1 , wherein R is H or P-Sp b .

3. The compound of claim 1 , of the formula:

4. The compound according to claim 1 , of the formula:

wherein Sp 1 is a spacer group.

5. The compound according to claim 1 , wherein P is an acrylate, methacrylate or oxetane.

6. The compound according to claim 1 , wherein Sp 1 , and Sp a and Sp b if not a single bond, are —(CH 2 ) a —, —(CH 2 ) a —O—, —(CH 2 ) a —CO—O—, or —(CH 2 ) a —O—CO—, wherein a is 2, 3, 4, 5 or 6, and the O-atom or the CO-group, respectively, is connected to the aromatic ring.

7. A liquid crystal (LC) medium comprising one or more polymerizable compounds formula I as defined in claim 1 .

8. The LC medium of claim 7 , comprising
a polymerizable component A) comprising one or more polymerizable compounds of formula I, and
a liquid-crystalline LC component B) comprising one or more mesogenic or liquid-crystalline compounds.

9. The LC medium of claim 7 , comprising one or more compounds of the formulae CY and/or PY:

wherein
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—, —OCO— or —OCO— in such a way that O atoms are not linked directly to one another,
Z x and Z y each, independently of one another, denote —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, and
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, CHF 2 .

10. The LC medium according to claim 7 , comprising one or more compounds of the following formulae:

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

R A1 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 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 O atoms are not linked directly to one another,
Z x —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —O 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond,
L 1-4 each, independently of one another, H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 H,
x 1 or 2, and
z 0 or 1.

11. The LC medium according to claim 7 , comprising one or more compounds of the following formula:

in which 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 O 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 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O— or a single bond.

12. The LC medium according to claim 7 , wherein the polymerizable compounds of formula I are polymerized.

13. A process of preparing an LC medium of claim 7 , 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.

14. An LC display comprising one or more compounds of formula I as defined in claim 1 .

15. The LC display of claim 14 , which is a PSA display.

16. The LC display of claim 15 , which is a PS-VA, PS-OCB, PS-IPS, PS-FFS, PS-UB-FFS, PS-posi-VA or PS-TN display.

17. The LC display of claim 15 , 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 LC medium, comprising one or more polymerizable compounds of formula I, wherein the polymerizable compounds are polymerized between the substrates of the display.

18. A process for the production of an LC display according to claim 17 , comprising providing an LC medium, comprising one or more polymerizable compounds, of formula I, between the substrates of the display, and polymerizing the polymerizable compounds.

19. A compound according to claim 1 , of formula II

R′ denotes H or Pg-Sp b , and Pg denotes OH, a protected hydroxyl group or a masked hydroxyl group.

20. A process for preparing a compound of formula I of claim 1 , wherein P denotes acrylate or methacrylate, by esterification of a compound of formula II

wherein Pg denotes OH, and R′ denotes H or Pg-Sp b using corresponding acids, acid derivatives, or halogenated compounds containing a group P, in the presence of a dehydrating reagent.

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Schwebel Nico
• Baron Eveline
• Marten Christoph

Classifications

• G02F1/1333

  Constructional arrangements; {Manufacturing methods}(G02F1/135, G02F1/136 take precedence) · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K2019/0448

  the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate · CPC title

• C09K2019/0481

  Phenylene substituted in meta position · CPC title

• G02F1/137 Primary

  characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering · CPC title