Polymerizable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-9567526-B2
Application number	US-201414314470-A
Country	US
Kind code	B2
Filing date	Jun 25, 2014
Priority date	Jun 25, 2013
Publication date	Feb 14, 2017
Grant date	Feb 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 PSA (“polymer sustained alignment”) type.

First claim

The invention claimed is:

1. A polymerizable compound according to the following formula
P 1 -(A 1 -Z 1 ) m -A 2 -(CO—O) y -Sp 2 -P 2   I

wherein
Sp 2 is a spacer group which is optionally substituted by P 1 —Sp′-,
Sp′ is alkylene with 1 to 12 C atoms,
P 1 and P 2 independently of each other are each a polymerizable group,
A 1 , A 2 independently of each other, and on each occurrence identically or differently, are each an aryl, heteroaryl alicyclic or heterocyclic group having 4 to 25 C atoms, optionally containing fused rings, and which is unsubstituted or mono- or polysubstituted by L,
Z 1 is, on each occurrence identically or differently, —O—, —S—, —CO—, —CO—O—, —O—CO——O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n —, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—,—C≡C—, —CH═CH—CO—O—, —O—CO—CH═CH—, —CH 2 —CH 2 —CO—O—,—O—CO—CH 2 —CH 2 —, —CR 00 R 000 —, or a single bond,
L is P 1 -, P 1 -Sp 1 -(O—CO) x —F, Cl, Br, I,—CN,—NO 2 ,—NCO,—NCS, —OCN, —SCN, —C(═O )N(R x ) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 2 , optionally substituted silyl, optionally substituted aryl or heteroaryl having 5 to 20 ring atoms, or straight -chain or branched alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH 2 groups are each optionally replaced, independently of one another, by —C(R 00 )═C(R 000 )—, —C≡C—, —N(R 00 )—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms are each optionally replaced by F, Cl, CN, P 1 , P 1 -Sp 1 - or P 1 -Sp 1 (O—CO) x —,
Sp 1 is a spacer group which is optionally substituted by P 1 -Sp'- or is a single bond,
R 00 and R 000 are each, independently of one another, H or alkyl having 1 to 12 C atoms,
Y 1 is halogen,
R x is P 1 , P 1 -Sp 1 -, P 1 -(Sp 1 —O—CO) x —, H, halogen, straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are each optionally replaced by —O—, —S—,—CO—, —CO—O—,—CO—, or —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, Cl, P 1 -, P 1 -Sp 1 - or P 1 -(Sp 1 —O—CO) x —, optionally substituted aryl, aryloxy, heteroaryl or heteroaryloxy having 5 to 20 ring atoms,
m is 1, 2, 3 or 4,
n is 1, 2, 3 or 4,
x is 0 or 1, and
y is 1;
with at least one of the following provisos:
(a) at least one of A 1 and A 2 is substituted by a group L denoting P 1 -Sp 1 —(O—CO) x—,
(b) Sp 2 is substituted by P 1 -Sp 1 -,
(c) m is 2, 3, or 4, and/or
(d) P l and P 2 are selected from acrylate and methacrylate.

2. A polymerizable compound according to claim 1 , wherein A 1 and A 2 are each, independently of one another, 1,4-phenylene, 1,3-phenylene, or 1,2-phenylene, which in each case is unsubstituted or mono- or polysubstituted by L.

3. A polymerizable compound according to claim 1 , wherein
Sp 1 is selected from —(CH 2 ) p1 —, —(CH 2 ) p2 —O—(CH 2 p3 —, —(CH 2 ) p1 —O—, —O—(CH 2 ) p1 —,and

 and
Sp 2 is selected from —(CH 2 ) p1 ,—,—(CH 2 ) p2 —O—(CH 2 ) p3 —, and

in which p 1 is an integer from 1 to 6, and
p2 and p3 are independently of each other 1, 2 or 3
provided that, in a group Sp 1 —(O—CO) x —, if x is 1 then Sp 1 is not —(CH 2 ) p1 —O—or —O—(CH 2 ) p1 —.

4. A polymerizable compound according to claim 1 , wherein P l and P 2 are independently of each other selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxide.

5. A polymerizable compound according to claim 1 , wherein said compound is selected from the following sub-formulae:

wherein r is 0, 1, 2, 3 or 4.

6. A liquid crystalline (LC) medium comprising
a polymerizable component A) comprising one or more polymerizable compounds according to claim 1 , and
a liquid crystalline component B) comprising one or more compounds selected from mesogenic or liquid crystalline compounds.

7. The liquid crystalline medium according to claim 6 ,
wherein component B comprises one or more compounds of 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 are each optionally 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, and
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 .

8. The liquid crystalline medium according to claim 6 , wherein component B comprises 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 are each optionally 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, and
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.

9. The liquid crystalline medium according to claim 6 , wherein component B comprises one or more compounds comprising an alkenyl group, which is stable to a polymerization reaction under the conditions used for the polymerization of the polymerizable compounds.

10. The liquid crystalline medium according to claim 6 , wherein the polymerizable compounds are polymerized.

11. A method of generating an electro-optical effect comprising applying a voltage to a liquid crystalline medium containing a polymerizable compound according to claim 1 , in a liquid crystalline display.

12. A method of generating an electro-optical

Assignees

• Merck Patent Gmbh

Inventors

• Engel Martin
• Baron Eveline
• Brocke Constanze
• Haas Helga
• Derow Stephan
• Marten Christoph
• Tong qiong

Classifications

• C09K19/12

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

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K2019/0448

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

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K2019/122

  Ph-Ph · CPC title