Polymerisable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-10669483-B2
Application number	US-201515544157-A
Country	US
Kind code	B2
Filing date	Dec 17, 2015
Priority date	Jan 19, 2015
Publication date	Jun 2, 2020
Grant date	Jun 2, 2020

Abstract

The present invention relates to polymerisable compounds, to processes and intermediates for the preparation thereof, to liquid-crystal (LC) media comprising them, and to the use of the polymerisable 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 liquid-crystal medium comprising one or more compounds of formula I
P-Sp-(A 2 -Z 2 -A 1 ) m1 -Z 1 -T  I

wherein the individual radicals, independently of each other, and on each occurrence identically or differently, have the following meanings
-(A 2 -Z 2 -A 1 ) m1 - is a single bond or is selected from the following formulae

r is 0, 1, 2, 3 or 4,
s is 0, 1, 2 or 3,
t is 0, 1 or 2,
u is 0, 1, 2, 3, 4 or 5,
T is a group selected from the following formulae 1, 2, 3 and 4,

R a-f are, each independently, straight chain or branched alkyl with 1 to 10 C atoms,
R g is H or straight chain or branched alkyl with 1 to 10 C atoms, or benzyl,
P is vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane or epoxy,
Sp is a spacer group or a single bond,
Z 1 is —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, with the proviso that, if -(A 2 -Z 2 -A 1 ) m1 - is a single bond and Sp is a single bond, Z 1 is a single bond,
R 00 , R 000 is H or alkyl having 1 to 12 C atoms,
L is P-Sp-, 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, Cl or P-Sp-, or L is a group selected from formula 1, 2, 3 and 4, and
n is 1, 2, 3 or 4.

2. The LC medium of claim 1 , wherein R a-d are selected, independently of each other, from methyl, ethyl, n-propyl, isopropyl, n-butyl, and t-butyl.

3. The LC medium according to claim 1 , wherein the one or more compounds of formula I are selected from the following formulae

wherein
P, Sp, R a-f , Z 1 , and L are as defined for the compound of formula I,
r is 0, 1, 2, 3 or 4 and
s is 0, 1, 2 or 3.

4. The LC medium according to claim 1 , wherein Z 1 denotes —CO—O—, —O—CO— or a single bond.

5. The LC medium according to claim 1 , wherein P is acrylate or methacrylate.

6. The LC medium according to claim 1 , wherein Sp is a single bond.

7. The LC medium according to claim 1 , which additionally comprises one or more polymerisable compounds that are different from formula I.

8. The LC medium of claim 7 , which comprises
a polymerisable component A) comprising one or more polymerisable compounds of formula I, and optionally one or more polymerisable compounds different from formula I, and
a liquid-crystalline LC component B) comprising one or more mesogenic or liquid-crystalline compounds.

9. The LC medium according to claim 7 , wherein the said polymerisable compounds that are different from formula I are selected from the following formulae

in which the individual radicals have the following meanings:
P 1 , P 2 , P 3 each, independently of one another, denote an acrylate or methacrylate group,
Sp 1 , Sp 2 , Sp 3 each, independently of one another, denote a single bond or a spacer group,
R aa denotes H, F, Cl, CN or straight-chain or branched alkyl having 1 to 25 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —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 one or more H atoms may be replaced by F, Cl, CN or P 1 —Sp 1 -,
R 0 , R 00 each, independently of one another and identically or differently on each occurrence, denote H or alkyl having 1 to 12 C atoms,
R y and R z each, independently of one another, denote H, F, CH 3 or CF 3 ,
X 1 , X 2 and X 3 each, independently of one another, denote —CO—O—, —O—CO— or a single bond,
Z 1 denotes —O—, —CO—, —C(R y R z )— or —CF 2 CF 2 —,
Z 2 and Z 3 each, independently of one another, denote —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 — or —(CH 2 ) n —,
n is 2, 3 or 4,
L on each occurrence, identically or differently, denotes F, Cl, CN or straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
L′ and L″ each, independently of one another, denote H, F or Cl,
r denotes 0, 1, 2, 3 or 4,
s denotes 0, 1, 2 or 3,
t denotes 0, 1 or 2, and
x denotes 0 or 1.

10. The LC medium according to claim 9 , wherein the one or more polymerisable compounds that are different from formula I are of formula M2.

11. The LC medium according to claim 1 , which further comprises one or more compounds selected from the formulae CY and PY:

in which the individual radicals have the following meanings:
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, in which 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, and
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 .

12. The LC medium according to claim 1 , which

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Haas Helga
• Kodek Thorsten
• Kirsch Peer
• Brocke Constanze
• Baron Eveline
• Marten Christoph

Classifications

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C09K2019/122

  Ph-Ph · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K19/322

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

• C09K19/44 Primary

  containing compounds with benzene rings directly linked · CPC title