Polymerisable liquid crystal material and polymerised liquid crystal film

Patent metadata

Field	Value
Publication number	US-10106742-B2
Application number	US-201414917669-A
Country	US
Kind code	B2
Filing date	Jul 31, 2014
Priority date	Sep 13, 2013
Publication date	Oct 23, 2018
Grant date	Oct 23, 2018

Abstract

The invention relates to a polymer film comprising a polymerized liquid crystal (LC) material with improved adhesion to a substrate, to methods for preparing such a polymer film, to a polymerizable LC material used for the preparation of such a polymer film, and to the use of the polymer film and said polymerizable LC material for optical, electrooptical, decorative or security uses and devices.

First claim

The invention claimed is:

1. Polymerisable liquid crystal (LC) material comprising a mixture of:
one or more polymerisable mesogenic compounds including one or more mono-, di- or multi-reactive compound of the formula II:
P-Sp-MG-R 0   II

wherein
P is a polymerisable group,
Sp is a spacer group or a single bond,
MG is a rod-shaped mesogenic group,
R 0 is H, alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms more, or is Y 0 or -Sp-P, and
Y 0 is F, Cl, CN, NO 2 , OCH 3 , OCN, SCN, optionally fluorinated alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 4 C atoms, or mono- oligo- or polyfluorinated alkyl or alkoxy with 1 to 4 C atoms;
and at least one adhesion promoter, wherein the at least one adhesion promoter is selected from a (meth)acrylic side chain polymer comprising at least one subunit of formula I,

wherein
R 1 denotes —H or —C m H 2m+1 ,
m denotes an integer of 1 to 15,
R 2 denotes each and independently and in each occurrence, a linear alkylene group having 1 to 4 carbon atoms, and

n denotes an integer from 2 to 10.

2. Polymerisable LC material according to claim 1 , wherein the adhesion promoter is selected from a (meth)acrylic polymer comprising a recurring unit of formula I, wherein R 2 denotes methylene or ethylene.

3. Polymerisable LC material according to claim 1 , wherein the adhesion promoter has an amine hydrogen equivalent weight in the range from 300 to 2000 g/eq.

4. Polymerisable LC material according to claim 1 , wherein the adhesion promoter has an amine value in the range from 0.1 to 3.0 mmol/g.

5. Polymerisable LC material according to claim 1 , wherein the one or more polymerisable mesogenic compounds are selected from one or more mono-, di- and/or multireactive polymerisable mesogenic compounds.

6. A polymer film comprising the polymerisable LC material according to claim 1 .

7. Polymer film according to claim 6 , wherein the polymerisable LC material is homeotropically aligned.

8. Polymer film according to claim 6 , wherein the polymer film is obtained by the following steps
providing a layer of the polymerisable LC material onto a substrate,
polymerising the LC material, and
optionally, removing the polymerised LC material from the substrate and/or optionally providing it the polymerised LC material onto another substrate.

9. An optical, electrooptical, information storage, decorative or security application, liquid crystal display, 3D display, projection system, polariser, compensator, alignment layer, circular polariser, colour filter, decorative image, liquid crystal pigment, reflective film with spatially varying reflection colours, multicolour image, non-forgeable document, identity or credit card or banknote, which comprises a polymerizable LC material wherein the polymerizable LC material is according to claim 1 .

10. A component or device which is: an optical component or device, polariser, patterned retarder, compensator, alignment layer, circular polariser, colour filter, decorative image, liquid crystal lens, liquid crystal pigment, reflective film with spatially varying reflection colours or multicolour image for decorative or information storage, comprising at least one polymer film, wherein the at least one polymer film is according to claim 6 .

11. Liquid crystal display comprising a polymerizable LC material wherein the polymerizable LC material is according to claim 1 .

12. Authentification, verification or security marking, coloured or multicolour image for security use, or non-forgeable object or document of value, comprising at least one polymer film, wherein the at least one polymer film is according to claim 6 .

13. An optical, electrooptical, information storage, decorative or security application, liquid crystal display, 3D display, projection system, polariser, compensator, alignment layer, circular polariser, colour filter, decorative image, liquid crystal pigment, reflective film with spatially varying reflection colours, multicolour image, non-forgeable document, identity card, credit card or banknote, which comprises a polymer film, wherein the polymer film is according to claim 6 .

14. Optical component or device, polariser, patterned retarder, compensator, alignment layer, circular polariser, colour filter, decorative image, liquid crystal lens, liquid crystal pigment, reflective film with spatially varying reflection colours or multicolour image for decorative or information storage, comprising at least one polymerisable LC material wherein the at least one polymerizable LC material is according to claim 1 .

15. Liquid crystal display comprising a polymer film, wherein the polymer film is according to claim 6 .

16. Authentification, verification or security marking, coloured or multicolour image for security use, or non-forgeable object or document of value, comprising a polymerizable LC material wherein the polymerizable LC material is according to claim 1 .

17. Authentification, verification or security marking, coloured or multicolour image for security use, or non-forgeable object or document of value, comprising a component or device according to claim 10 .

18. A non-forgeable object or document of value, which is an identity card, a credit card or a banknote, comprising at least one polymer film, wherein the at least one polymer film is according to claim 6 .

19. Polymerisable LC material according to claim 1 , wherein, in formula I,
R 1 denotes —H or -methyl,
R 2 denotes each and independently and in each occurrence, methylene or ethylene, and
n denotes 2.

20. Polymerisable LC material according to claim 1 , wherein, in formula II:
P is an acryl, methacryl, vinyl, vinyloxy, propenyl ether, epoxy, oxetane or styrene polymerisable group,
MG is of formula M,
M is -(A 21 -Z 21 ) k -A 22 -(Z 22 -A 23 ) l -,
wherein
A 21 to A 23 are in each occurrence independently of one another an aryl-, heteroaryl-, heterocyclic- or alicyclic group optionally being substituted by one or more identical or different groups L, preferably 1,4-cyclohexylene or 1,4-phenylene, 1,4 pyridine, 1,4-pyrimidine, 2,5-thiophene, 2,6-dithieno[3,2-b:2′,3′-d]thiophene, 2,7-fluorine, 2,6-naphtalene, 2,7-phenanthrene optionally being substituted by one or more identical or different groups L,
Z 21 and Z 22 are in each occurrence independently from each other, —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—COO—, —CO—NR 01 -, —NR 01 —CO—, —NR 01 —CO—NR 02 , —NR 01 —CO—O—, —O—CO—NR 01 —, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH 2 CH 2 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═N—, —N═CH—, —N═N—, —CH═CR 01 —, —CY 01 ═CY 02 —, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, or a single bond,
R 0 is alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 20 C atoms, which are optionally fluorinated, or is Y 0 or -Sp-P,
Y 0 is F, Cl, CN, NO 2 , OCH 3 , OCN, SCN, optionally fluorinated alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 4 C atoms, or mono- oligo- or polyfluorinated alkyl or alkoxy with 1 to 4 C atoms, preferably F, Cl, CN, NO 2 , OCH 3 , or mono- oligo- or polyfluorinated alkyl or alkoxy with 1 to 4 C atoms
Y 01 and Y 02 have each and independently the meani

Assignees

• Merck Patent Gmbh

Inventors

• Yoon Hyun-Jin
• Yun Yong-Kuk
• Jin Heui-Seok
• Choi Yong-Hyun

Classifications

• C09K19/52 Primary

  characterised by components which are not liquid crystals, e.g. additives {with special physical aspect: solvents, solid particles} · CPC title

• C09K19/542 Primary

  Macromolecular compounds · CPC title

• C09K2019/0448

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

• G02F1/137

  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