Method for the preparation of a liquid crystal polymer film

Patent metadata

Field	Value
Publication number	US-11718790-B2
Application number	US-202017424563-A
Country	US
Kind code	B2
Filing date	Jan 20, 2020
Priority date	Jan 22, 2019
Publication date	Aug 8, 2023
Grant date	Aug 8, 2023

Abstract

The present invention relates to a method for the preparation of a homogeneous aligned liquid crystal polymer film, a polymer film obtainable from the corresponding method of production, and to the use of such polymer film for optical components and electro-optical decorative, as well as to components and devices comprising such polymer film.

First claim

The invention claimed is:

1. A method for manufacturing a homogeneous aligned polymer film comprising at least the steps of:
providing a polymerizable liquid crystal mixture, comprising one or more polymerizable liquid crystal molecules, wherein the total concentration of the one or more polymerizable liquid crystal molecules in the liquid crystal mixture is 85 to 99.9%, and one or more self assembling photoalignment agents, on a substrate;
irradiating the liquid crystal mixture with linearly polarised light causing photoalignment of the polymerizable liquid crystal mixture;
optionally curing the polymerizable liquid crystal compounds by irradiation with ultraviolet light,
wherein said homogeneous aligned polymer film is manufactured.

2. The method according to claim 1 , wherein the one or more self assembling photoalignment agents are compounds of formula S,

wherein
L s each, identically or differently, denote F, Cl, CN, SCN, SF 5 or a straight-chain, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, or a branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 12 C atoms, (Sp s ) r1 -G, Y, or (Sp s ) r1 -PS
P s each, independently of one another, denote a polymerisable group,
Sp s on each occurrence, identically or differently, denote a spacer group,
Y denotes (R b ) 2 N- or, RC(O)O—,
G denotes —OH or Si(OR a ) 3 ,
R a , R b , R c each denote, identically or differently, H, a straight chain alkyl with 1 to 6 C atoms, or a branched alkyl with 3 to 6 C atoms,
r1 denotes 0 or 1,
t1, t2 denotes, each independently, 1, 2, 3, 4 or 5, and
Z s denotes —N═N—, —CH═CH—, —CH═CH—COO—, —OCO—CH═— CH—, —CO—CH═CH—, or —CH═CH—CO—, wherein one or more H are optionally replaced by halogen.

3. The method according to claim 1 , wherein the one or more self assemble photoalignment agents are compounds of formula S1,

wherein
Y denotes (R b ) 2 N—, R c C(O)O—, or a group Ls,
Sp denotes a spacer group,
G denotes —OH or Si(OR a ) 3 ,
R a , R b , R c each denote, identically or differently, a straight chain or branched alkyl with 1 to 6 C atoms, or branched alkyl with 3 to 6 C atoms, LS each, identically or differently, denote P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 00 R 000 , —C(═O)OR 00 , —C(═O)R 00 , —NR 00 R 000 , —OH, —SF 5 , optionally substituted silyl, or aryl or heteroaryl with 3 to 12 C atoms, or a straight chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 12 C atoms, or a branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 3 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl,
R 00 and R 000 each, independently of one another, denote H, F or a straight-chain or branched alkyl having 1 to 12 C atoms, or a branched alkyl having 3 to 12 C atoms, wherein one or more H atoms are optionally replaced by F,
t1, t2 denotes 0, 1, 2, 3 or 4.

4. The method according to claim 1 , wherein the total concentration of the one or more self assembling photoalignment agents in the liquid crystal mixture is 1 to 15%.

5. The method according to claim 1 , wherein the one or more polymerizable liquid crystal molecules are compounds of formula DRM,
P 1 -Sp 1 -MG-Sp 2 -P 2   DRM

wherein
P 1 and P 2 independently of each other denote a polymerizable group,
Sp 1 and Sp 2 independently of each other are a spacer group or a single bond, and
MG is a rod-shaped mesogenic group.

6. The method according to claim 1 , wherein the one or more polymerizable liquid crystal molecules are selected from compounds of the following formulae,

wherein
P 0 is, in case of multiple occurrence independently of one another, an acryl, methacryl, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether or styrene group,
L is P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 00 R 000 , —C(═O)OR 00 , —C(═O)R 00 , —NR 00 R 000 , —OH, —SF 5 , optionally substituted silyl, or aryl or heteroaryl with 3 to 12 C atoms, a straight chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 12 C atoms, or a branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 3 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl,
R 00 and R 000 each, independently of one another, denote H, F or a straight-chain alkyl having 1 to 12 C atoms, or branched alkyl having 3 to 12 C atoms, wherein one or more H atoms are optionally replaced by F,
r is 0, 1, 2, 3 or 4,
x and y are independently of each other 0 or identical or different integers from 1 to 12,
Z is, each independently, 0 or 1, with z being 0 if the adjacent x or y is 0.

7. The method according to claim 1 , wherein the one or more polymerizable liquid crystal molecules are of formula MRM,
P 1 -Sp 1 -MG-R  MRM

wherein
P 1 denotes a polymerizable group,
Sp 1 is a spacer group or a single bond,
MG is a rod-shaped mesogenic group,
R is F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NRXRY, —C(═O)X, —C(═O)ORX, —C(═O)RY, —NR*RY, —OH, —SF 5 , optionally substituted silyl, or a straight chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 12 C atoms, or a branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 3 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl,
X is halogen, and
R x and R y are independently of each other H or alkyl with 1 to 12 C-atoms.

8. The method according to claim 1 , wherein the one or more polymerizable liquid crystal molecules are selected from the following formulae,

wherein P 0 is, in case of multiple occurrence independently of one another, an acryl, methacryl, oxetane, epoxy, vinyl, heptadiene, vinyloxy, propenyl ether or styrene group,
L is P-Sp-, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR 00 R 2000 , —C(═O)OR 00 , —C(═O)R 00 , —NR 200000 , —OH, —SF 5 , optionally substituted silyl, or aryl or heteroaryl with 3 to 12 C atoms, or a straight chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 12 C atoms, or a branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 3 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl,
R 00 and R 000 each, independently of one another, denote H, F or a straight-chain or branched alkyl having 1 to 12 C atoms, or a branched alkyl having 3 to 12 C atoms, wherein one or more H atoms are optionally replaced by F,
r is 0, 1, 2, 3 or 4,
x and y are independently of each other 0 or identical or different integers from 1 to 12,
Z is, each independently, 0 or 1, with z being 0 if the adjacent x or y is 0, R 0 is an alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 or more C atoms or denotes Y 0 ,
Y 0 is F, Cl, CN, NO 2 , OCH 3 , OCN, SCN, SF 5 , or a mono- oligo- or

Assignees

• Merck Patent Gmbh

Inventors

• Mulcahy Stephen
• Beltran Gracia Eduardo
• Parri Owain
• Poole Vicki
• Allen James
• Adlem Kevin
• Arasi Hassan

Classifications

• C09K19/3857 Primary

  containing at least one asymmetric carbon atom · CPC title

• C08F222/1025

  of aromatic dialcohols · CPC title

• C09K19/56 Primary

  Aligning agents · CPC title

• G02F1/133726

  made of a mesogenic material · CPC title

• G02F1/133738

  for homogeneous alignment · CPC title