Polymerisable liquid crystal material and polymerised liquid crystal film

Patent metadata

Field	Value
Publication number	US-11118112-B2
Application number	US-201615740870-A
Country	US
Kind code	B2
Filing date	Jun 6, 2016
Priority date	Jun 30, 2015
Publication date	Sep 14, 2021
Grant date	Sep 14, 2021

Abstract

Compounds of formula I,

(R 11 O) s Si(CH 3 ) 3−s -Sp 11 -NR 12 -Sp 12 -C(OR 13 ) t H 3−t   I

wherein the variable groups are as defined herein are useful as adhesion promotors in polymerizable liquid crystal (LC) material.

First claim

The invention claimed is:

1. A polymerizable liquid crystal material comprising one or more polymerizable mesogenic compounds and at least one compound of formula I,
(R 11 O) s Si(CH 3 ) 3−s -Sp 11 -NR 12 -Sp 12 -C(OR 13 ) t H 3−t   I

wherein
R 11 is, in each case independently, methyl or ethyl;
R 12 is H or straight-chain alkylene having 1 to 12 C atoms or branched alkylene having 3 to 12 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently of one another by —CH═CH—, —C≡C—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO— 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 may each be replaced by F, Cl or CN;
R 13 is, in each case independently, methyl or ethyl;
Sp 11 is a single bond or straight-chain alkylene having 1 to 12 C atoms or branched alkylene having 3 to 12 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —CH═CH—, —C≡C—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO— 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 may each be replaced by F, Cl or CN;
Sp 12 is a single bond or straight-chain alkylene having 1 to 12 C atoms or branched alkylene having 3 to 12 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently from one another, by —CH═CH—, —C≡C—, —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 may each be replaced by F, Cl or CN;
s is an integer from 0 to 3; and
t is 1.

2. The polymerizable liquid crystal material according to claim 1 , wherein said compound is a compound of formula I-A
(R 11 O) 3 Si-Sp 11 -NR 12 -Sp 12 -C(OR 13 ) t H 3−t   I-A

wherein R 11 to R 13 , Sp 11 , Sp 12 and t have the meanings given in claim 1 .

3. The polymerizable liquid crystal material according to claim 1 , in which R 11 is methyl.

4. The polymerizable liquid crystal material according to claim 1 , in which R 13 is methyl.

5. The polymerizable liquid crystal material according to claim 1 , in which Sp 12 is methylene or ethylene.

6. The polymerizable liquid crystal material according to claim 1 , in which Sp 11 denotes a methylene, ethylene, propylene, or butylene.

7. The polymerizable liquid crystal material according to claim 1 , in which the polymerizable mesogenic compounds are selected from one or more monoreactive polymerizable mesogenic compounds.

8. A polymer film obtainable from a polymerizable liquid crystal material according to claim 1 , by a process comprising:
providing a layer of the polymerizable liquid crystal material onto a substrate,
polymerizing the polymerizable liquid crystal material, and
optionally, removing the polymerized liquid crystal material from the substrate and/or optionally providing the polymerized liquid crystal material onto another substrate.

9. The polymer film according to claim 8 , wherein the polymerized liquid crystal material is homeotropically aligned.

10. A method of increasing the adhesion of a polymer film, obtained from a polymerizable liquid crystal material, to a substrate, film or surface, by adding at least one compound of the following formula I to the polymerizable liquid crystal material before polymerization,
(R 11 O) s Si(CH 3 ) 3−s -Sp 11 -NR 12 -Sp 12 -C(OR 13 ) t H 3−t   I

wherein
R 11 is, in each case independently, methyl or ethyl;
R 12 is H or straight-chain alkylene having 1 to 12 C atoms or branched alkylene having 3 to 12 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently of one another by —CH═CH—, —C≡C—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO— 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 may each be replaced by F, Cl or CN;
R 13 is, in each case independently, methyl or ethyl;
Sp 11 is a single bond or straight-chain alkylene having 1 to 12 C atoms or branched alkylene having 3 to 12 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —CH═CH—, —C≡C—, —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 may each be replaced by F, Cl or CN;
Sp 12 is a single bond or straight-chain alkylene having 1 to 12 C atoms or branched alkylene having 3 to 12 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently from one another, by —CH═CH—, —C≡C—, —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 may each be replaced by F, Cl or CN;
s is an integer from 0 to 3; and
t is 1.

11. The method according to claim 10 , wherein the substrate is selected from TAC and COP substrates or is a color filter.

12. A liquid crystal display, 3D display, projection system, polarizer, compensator, alignment layer, circular polarizer, color filter, decorative image, liquid crystal pigments, reflective film with spatially varying reflection color, multicolor image, or non-forgeable documents comprising a polymerized material obtained by polymerizing the polymerizable liquid crystal material according to claim 1 .

13. An optical component or device, polarizer, patterned retarder, compensator, alignment layer, circular polarizer, color filter, decorative image, liquid crystal lens, liquid crystal pigment, reflective film with spatially varying reflection color, multicolor image for decorative or information storage, comprising a polymerizable liquid crystal material according to claim 1 .

14. The polymerizable liquid crystal material according to claim 1 , wherein
Sp 12 is methylene or ethylene,
Sp 11 denotes a methylene, ethylene, propylene, or butylene spacer, and
R 12 denotes H or an alkylene or alkoxy radical.

15. The polymerizable liquid crystal material according to claim 1 , wherein
R 11 denotes in each case a methyl radical,
R 13 denotes in each case a methyl radical,
Sp 12 is ethylene,
Sp 11 denotes straight n-propylene or branched sec-butylene, and
R 12 denotes H.

16. The polymerizable liquid crystal material according to claim 1 , wherein said compound is selected from the following compounds:

17. The polymerizable liquid crystal material according to claim 1 , wherein the polymerizable mesogenic compounds are selected from compounds of formula II:
P-Sp-MG-R 0   II

wherein
P is a polymerizable group,
Sp is a spacer group or a single bond,
MG is a rod-shaped mesogenic group,
R 0 is H, alkyl, alkoxy or thioalkyl with 1 to 20 C atoms or alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 2 to 20 C atoms more, which are optionally fluorinated, or is Y 0 or P-Sp-, and
Y 0 is F, Cl, CN, NO 2 , OCH 3 , OCN, SCN, optionally fluorinated alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 2 to 4 C atoms, or mono- oligo- or polyfluorinated alkyl or alkoxy with 1 to 4 C atoms.

18. The polymerizable liquid crystal material according to claim 17 , wherein
P is an acryl, methacryl, vinyl, vinyloxy, propenyl ether, epoxy, oxetane or styrene group,

Assignees

• Merck Patent Gmbh

Inventors

• Adlem Kevin
• Gardiner Iain
• Bradford Jack
• Mulcahy Stephen
• Allen James

Classifications

• C09K19/52 Primary

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

• C09K2219/03

  in the form of films, e.g. films after polymerisation of LC precursor · CPC title

• C09K19/54 Primary

  Additives having no specific mesophase {characterised by their chemical composition} · CPC title

• C09K2019/0448

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

• C09K19/3838

  Polyesters; Polyester derivatives · CPC title