Polymerizable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-11312909-B2
Application number	US-201615337456-A
Country	US
Kind code	B2
Filing date	Oct 28, 2016
Priority date	Oct 30, 2015
Publication date	Apr 26, 2022
Grant date	Apr 26, 2022

Abstract

Polymerizable compounds, to processes and intermediates for the preparation thereof, liquid-crystal (LC) media comprising them, and 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, or a stabilizers in LC media and LC displays.

First claim

The invention claimed is:

1. A compound of formula I
P-Sp-A 1 -(Z 1 -A 2 ) z -R  I

wherein individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
P a polymerizable acrylate or methacrylate group,
Sp a spacer group that is optionally substituted by one or more groups P or L a , or a single bond,

-A 1 -(Z 1 -A 2 ) z is

wherein the benzene rings are optionally substituted by one or more groups L, P-Sp-, L a or L a -Sp-
R P-Sp-,
L F, Cl, —CN, P-Sp-, L a , L a -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 P, F, Cl or L a -,
L a —C(R aa )(R bb )OH,
R aa , R bb straight-chain alkyl with 1 to 20 C atoms, branched alkyl with 3 to 20 C atoms, or cyclic alkyl with 3 to 12 C atoms, or R aa and R bb together with the C atom to which they are attached form a cyclic alkyl group with 3 to 12 C atoms, wherein in R aa and R bb 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,

wherein the compound of formula I contains at least one group L a or L a -Sp-.

2. The compound according to claim 1 , wherein R aa and R bb denote straight-chain alkyl with 1 to 12 C atoms or branched alkyl with 3 to 12 C atoms, or R aa and R bb together with the C atom to which they are attached form a cyclic alkyl group with 3 to 12 C atoms.

3. The compound according to claim 1 , wherein all groups P that are present in the compound have the same meaning.

4. The compound according to claim 1 , containing a group P-Sp- of the following formulae
P—CHL a -  SL1

P—(CH 2 ) cc —O-CHL a -  SL2

P—(CH 2 ) cc —CO—O-CHL a -  SL3

P—(CH 2 ) cc —CHL a -  SL4

cc is 1, 2, 3, 4, 5 or 6 and
L a is as defined in claim 1 .

5. The compound according to claim 1 , wherein A 1 -(Z 1 -A 2 ) z - is

wherein the benzene rings are optionally substituted by one or more groups L, P-Sp-, L a or L a -Sp-.

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

wherein
r1, r3, r7 are independently of each other 0, 1, 2 or 3,
r2 is 0, 1, 2, 3 or 4,
r4, r5, r6 are independently of each other 0, 1 or 2,
wherein r1+r7≥1, r1+r2+r3≥1, r4+r5≥1, r1+r3+r4≥1 and at least one of L denotes L a or L a -Sp-, and/or
wherein the compounds contain at least one group Sp that is substituted by L a .

7. A compound of the formula:

or a compound of formula I8-1 or I8-2 wherein P is replaced by Pg
Sp a spacer group that is optionally substituted by one or more groups P or L a , or a single bond,
P a polymerizable acrylate or methacrylate group,
Pg is —OH, a protected hydroxy group or a masked hydroxy group,
L F, Cl, —CN, P-Sp-, L a , L a -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 P, F, Cl or L a -,
L a —C(R aa )(R bb )OH,
R aa , R bb straight-chain alkyl with 1 to 20 C atoms, branched alkyl with 3 to 20 C atoms, or cyclic alkyl with 3 to 12 C atoms, or R aa and R bb together with the C atom to which they are attached form a cyclic alkyl group with 3 to 12 C atoms, wherein in R aa and R bb 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,
r1, r3, r7 are independently of each other 0, 1, 2 or 3,
r2 is 0, 1, 2, 3 or 4,
r4, r5, r6 are independently of each other 0, 1 or 2,
wherein R denotes H or Pg-Sp,
wherein r1+r7≥1, r1+r2+r3≥1, r4+r5≥1, r1+r3+r4≥1 and at least one of L denotes L a or L a -Sp-, and/or
wherein the compounds contain at least one group Sp that is substituted by L a .

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

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

10. The LC medium of claim 9 , wherein component B) comprises one or more compounds of formulae CY and/or PY:

in which
a denotes 1 or 2,
b denotes 0 or 1,

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 O 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 .

11. The LC medium according to claim 9 wherein component B) comprises 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:

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—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond,

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Haas Helga
• Hahn Alexander
• DEING Kaja Christina
• Marten Christoph

Classifications

• C09K2019/3425

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

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K19/3405

  the heterocyclic ring being a five-membered ring · CPC title

• C09K19/0403 Primary

  the structure containing one or more specific, optionally substituted ring or ring systems · CPC title

• C07C69/732 Primary

  of unsaturated hydroxy carboxylic acids · CPC title