Polymerisable mixtures and the use thereof in liquid crystal displays

Patent metadata

Field	Value
Publication number	US-9556382-B2
Application number	US-201113810769-A
Country	US
Kind code	B2
Filing date	Jun 30, 2011
Priority date	Jul 21, 2010
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

The present invention relates to polymerizable mixtures and to the use thereof for optical, electro-optical and electronic purposes, in particular in liquid-crystal (LC) media and LC displays, especially in LC displays of the PS (“polymer sustained”) or PSA (“polymer sustained alignment”) type.

First claim

The invention claimed is:

1. Polymerisable mixture comprising at least one first polymerisable compound and at least one second polymerisable compound, where the first polymerisable compound initiates and/or accelerates the polymerisation of the second polymerisable compound,
wherein the first polymerisable compound is selected from the group consisting of the following formulae:

 wherein
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,
r denotes 0, 1, 2, 3 or 4,
s denotes 0, 1, 2 or 3,
t denotes 0, 1 or 2,

P on each occurrence, identically or differently, denotes a polymerisable radical selected from the group consisting of:
CH 2 ═CW 1 —CO—O—,

CH 2 ═CH—O—,

(CH 2 ═CH) 2 CH—O—CO—,

(CH 2 ═CH) 2 CH—O—,

in which
W 1 denotes H, F, Cl, CN, CF 3 , phenyl or alkyl having 1 to 5 C atoms, W 2 denotes H or alkyl having 1 to 5 C atoms, and k1 denotes 0 or 1, Sp on each occurrence, identically or differently, denotes a spacer group or a single bond, R, R a each denote P-Sp; and
wherein the second polymerisable compound contains a ring system which is different from the first polymerisable compound, containing one or more carbo- or heterocyclic radicals and two or more than two polymerisable radicals, which are connected to the ring system directly or via a spacer group and
wherein the polymerisable radicals are selected from the group consisting of:
CH 2 ═CW 1 —CO—O—,

CH 2 ═CH—O—,

(CH 2 ═CH) 2 CH—O—CO—,

(CH 2 ═CH) 2 CH—O—,

in which
W 1 denotes H, F, Cl, CN, CF 3 , phenyl or alkyl having 1 to 5 C atoms,
W 2 denotes H or alkyl having 1 to 5 C atoms, and
k1 denotes 0 or 1.

2. Polymerisable mixture according to claim 1 , characterised in that the second polymerisable compound is selected from the group consisting of the following formulae:

in which P, Sp, R, L and r have the meanings indicated in claim 1 ,
Z 1 denotes —O—, —CO—, —CO—O—, —O—CO—, —C(R y R z )— or —CF 2 CF 2 —,
R y and R z each, independently of one another, denote H, F, CH 3 or CF 3 ,
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 —, where n is 2, 3 or 4,
L′ and L″ each, independently of one another, denote H, F or Cl, and
x denotes 0 or 1.

3. A LC medium comprising a polymerisable mixture according to claim 1 .

4. A LC medium, comprising
a polymerisable component A) comprising the polymerisable mixture according to claim 1 , and
a liquid-crystalline component B) comprising one or more low-molecular-weight compounds.

5. A LC medium comprising a polymer which is obtainable by polymerisation of a polymerisable mixture according to claim 1 , and one or more additional compounds other than the first polymerisable compound and second polymerisable compound of said polymerisable mixture according to claim 1 .

6. A LC medium comprising a polymerisable mixture comprising at least one first polymerisable compound and at least one second polymerisable compound, where the first polymerisable compound initiates and/or accelerates the polymerisation of the second polymerisable compound,
wherein the first polymerisable compound contains a ring system containing a divalent radical and two or more than two polymerisable radicals, which are connected to the ring system directly or via a spacer group, and the second polymerisable compound contains a ring system which is different from the first polymerisable compound, containing one or more carbo- or heterocyclic radicals and two or more than two polymerisable radicals, which are connected to the ring system directly or via a spacer group and
wherein the polymerisable radicals are selected from the group consisting of:
CH 2 ═CW 1 —CO—O—,

CH 2 ═CH—O—,

(CH 2 ═CH) 2 CH—O—CO—,

(CH 2 ═CH) 2 CH—O—,

in which
W 1 denotes H, F, Cl, CN, CF 3 , phenyl or alkyl having 1 to 5 C atoms,
W 2 denotes H or alkyl having 1 to 5 C atoms, and
k1 denotes 0 or 1 and
wherein the first polymerisable compound contains a divalent radical selected from the group consisting of the formulae A, B, C and D:

in which the individual radicals have the following meanings:
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,
r denotes 0, 1, 2, 3 or 4,
s denotes 0, 1, 2 or 3, and

t denotes 0, 1 or 2, which
additionally comprises 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,

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 .

7. A LC medium according to claim 3 , characterised in that it additionally comprises one or more compounds of the following formula:

in which the individual radicals have the following meanings:

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 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF— or a single bond.

8. A LC display of the PS or PSA type comprising a polymerisable mixture comprising at least one first polymerisable compound and at least one second polymerisable compound, where the first polymerisable compound initiates and/or accelerates the polymerisation of the second polymerisable compound,
wherein the first polymerisable compound contains a ring system containing a divalent radical and two or more than two polymerisable radicals, which are connected to the ring system directly or via a spacer group, and the second polymerisable compound cont

Assignees

• Goetz Achim
• Laut Sven Christian
• Taugerbeck Andreas
• Merck Patent Gmbh

Inventors

• Goetz Achim
• Laut Sven Christian
• Taugerbeck Andreas

Classifications

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• C08J2300/206

  Star polymers · CPC title

• G02F1/133365

  Cells in which the active layer comprises a liquid crystalline polymer · CPC title

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C09K2019/3425

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