Polymerisable liquid crystal material and polymerised liquid crystal film

Patent metadata

Field	Value
Publication number	US-12187946-B2
Application number	US-202117529519-A
Country	US
Kind code	B2
Filing date	Nov 18, 2021
Priority date	Nov 20, 2020
Publication date	Jan 7, 2025
Grant date	Jan 7, 2025

Abstract

A polymerisable LC material comprising one or more di- or multireactive mesogenic compounds and one or more compounds of formula UVI,and one or more compounds of formula UVII,Further, a method for its preparation, a polymer film with improved thermal durability and UV stability obtainable from a corresponding polymerisable LC material, a method of preparation of such polymer film, and the use of such polymer film and said polymerisable LC material for optical, electro-optical, decorative or security devices.

First claim

The invention claimed is:

1. A polymerizable LC material, comprising at least one di- or multireactive mesogenic compound and one or more compounds of formula UVII,

wherein the individual radicals have the following meanings:
R 1 to R 5 are each independently selected from the group consisting of H, alkyl, —OH, alkylaryl, alkylheteroaryl, cycloalkyl, cycloheteroalkyl, alkenyl, aryl and —SO 3 H, and
R 6 and R 7 denote each and independently a hydrogen atom, a hydroxy group, or a halogen atom; and
one or more compounds of formula UVI-a:

2. The polymerisable LC material according to claim 1 , further comprising one or more compounds of formula UVI,

in which
R 11 on each occurrence, independently of one another, denotes H, F, or a straight-chain alkyl having 1-20 C atoms or branched alkyl having 3-20 C atoms, in which one —CH 2 — group or, if present, a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, and one or, if present, a plurality of —CH 2 — groups may be replaced by —CH═CH— or —C≡C—, and in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 ,
R 12 on each occurrence, independently of one another, denotes a straight-chain alkyl having 1-20 C atoms or branched alkyl having 3-20 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, a hydrocarbon radical which contains a cycloalkyl or alkylcycloalkyl unit and in which one —CH 2 —group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, and in which one H atom or a plurality of H atoms may be replaced by OR 13 , N(R 13 )(R 14 ) or R 15 , or an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 ,
R 13 on each occurrence, independently of one another, denotes a straight-chain alkyl or acyl group having 1 to 10 C atoms or branched alkyl or acyl group having 3 to 10 C atoms or an aromatic hydrocarbon or carboxylic acid radical having 6-12 C atoms,
R 14 on each occurrence, independently of one another, denotes a straight-chain alkyl or acyl group having 1 to 10 C atoms or branched alkyl or acyl group having 3 to 10 C atoms or an aromatic hydrocarbon or carboxylic acid radical having 6 to 12 C atoms,
R 15 on each occurrence, independently of one another, denotes a straight-chain alkyl group having 1 to 10 C atoms or branched alkyl group having 3 to 10 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—,
S 11 and S 12 on each occurrence, independently of one another, denote a straight-chain alkylene group having 1 to 20 C atoms or a branched alkylene group having 3 to 20 C atoms, in which one —CH 2 — group or, if present, a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, and one or, if present, a plurality of —CH 2 — groups may be replaced by —CH═CH— or —C≡C— and in which one H atom or a plurality of H atoms may be replaced by F, OR 13 , N(R 13 )(R 14 ) or R 15 , or denote a single bond,
X 11 denotes C,
Y 11 to Y 14 each, independently of one another, denote methyl or ethyl,
Z 11 to Z 14 on each occurrence, independently of one another, denote —O—, —(C═O)—, —O—(C═O)—, —(C═O)—O—, —O—(C═O)—O—, —(N—R 13 )—, —N—R 13 —(C═O)— or a single bond if S 11 is a single bond, but both Z 11 and Z 12 do not simultaneously denote —O—, and, however, if S 12 is a single bond, both Z 13 and Z 14 do not simultaneously denote —O—, and, however, if —X 11 [—R 11 ] o — is a single bond, both Z 12 and Z 13 do not simultaneously denote —O—,
p denotes 1 o 2,
o denotes (3-p),
n*p denotes an integer from 3 to 10,
in the case where p=1,
m denotes (10-n),
and in the case where p=2,
n denotes an integer from 2 to 4, and
m denotes (4-n),

 denotes an organic radical having (m+n) bonding sites,
and, in the case where p=1, —X 11 [—R 11 ] o — may alternatively also denote a single bond.

3. The polymerisable LC material according to claim 1 , wherein the one or more compounds of formula UVII are selected from the group of compounds of the following subformulae

4. The polymerisable LC material according to claim 1 , wherein the at least one di- or multireactive mesogenic compound is selected 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 polymerisable 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, which is preferably selected of formula MG
(A 1 -Z 1 ) n -A 2 -  MG

wherein
A 1 and A 2 denote, in case of multiple occurrence independently of one another, an aromatic or alicyclic group, which optionally contains one or more heteroatoms selected from N, O and S, and is optionally mono- or polysubstituted by L 1 ,
L 1 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, aryl or heteroaryl with 1 to 12 C atoms, straight chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 to 12 C atoms or 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 independently of each other denote H or alkyl with 1 to 12 C-atoms,
Z 1 denotes, in case of multiple occurrence independently of one another, —O—, —S—, —CO—, —COO—, —OCO—, —S—CO—, —CO—S—, —O—COO—, —CO—NR 00 —, —NR 00 —CO—, —NR 00 —CO—NR 000 , —NR 00 —CO—O—, —O—CO—NR 00 —, —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 ) n1 , —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═N—, —N═CH—, —N═N—, —CH═CR 00 —, —CY 1 ═CY 2 —, —C≡C—, —CH═CH—COO—, —OCO—CH═CH— or a single bond,
Y 1 and Y 2 independently of each other denote H, F, Cl or CN,
n is 1, 2, 3 or 4, and
n1 is an integer from 1 to 10.

5. The polymerisable LC material according to claim 1 , wherein at least one direactive mesogenic compound is 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 has on each occurrence identically or differently one of the meanings given for L 1 in formula DRM,
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

Assignees

• Merck Patent Gmbh

Inventors

• Park Jin-Soon
• Lee Hoo-Yong
• Yoon Hyun-Jin
• Jin Heui-Seok

Classifications

• C09K2019/0448

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

• C09K2019/0414

  containing a heterocyclic ring · CPC title

• C09K19/348

  containing at least two nitrogen atoms · CPC title

• C09K19/0403

  the structure containing one or more specific, optionally substituted ring or ring systems · CPC title

• G02B5/3016

  involving passive liquid crystal elements (optical properties of liquid crystals G02F1/0063; polarising elements associated with active liquid crystal devices G02F1/133528) · CPC title