Polymerisable liquid crystal material and polymerised liquid crystal film

Patent metadata

Field	Value
Publication number	US-11873439-B2
Application number	US-201917299210-A
Country	US
Kind code	B2
Filing date	Nov 29, 2019
Priority date	Dec 3, 2018
Publication date	Jan 16, 2024
Grant date	Jan 16, 2024

Abstract

The invention relates to a polymerisable LC material comprising one or more di- or multireactive mesogenic compounds and one or more compounds of formula UVI,

wherein the individual radicals have one of the meaning as given in the claims. Furthermore, the present invention relates also to a method for its preparation, a polymer film with improved thermal durability and UV stability obtainable from a corresponding polymerisable LC material, to a method of preparation of such polymer film, and to 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 multireactive mesogenic compound, one or more compounds of formula UVI, and optionally at least one monoreactive mesogenic compound,

wherein
R 1 and R 6 each and independently from another denote, H, halogen, —OH, —SH, —NR xx R yy —, —CO—R xx —, —COOR xx , —OCOR xx , —OCO—OR xx , —S—COR xx , —CO—SR xx , —NR xx —CO—OR yy , —O—CO—NR xx R yy , —NR xx —CO—NR xx R yy , whereby one of R 1 or R 6 in formula UVI denotes —OH
R 2 and R 5 each and independently from another denote, H, halogen, —OH, —SH, —NR xx R yy —, —CO—R xx —, —COOR xx , —OCOR xx , —OCO—OR xx , —S—COR xx , —CO—SR xx , —NR xx —CO—OR yy , —O—CO—NR xx R yy , —NR xx —CO—NR xx R yy ,
R 3 and R 4 each represent a hydrogen atom, a hydroxy group, or a halogen atom,
R xx and R yy each, independently of one another, denotes H, alkyl having 1 to 12 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —O—, —S—, —NH—, —NR xx —, —SiR xx R yy —, —CO—, —COO—, —OCO—, —OCO—O—, —S—O—, —CO—S—, —NR xx —CO—O—, —O—CO—NR xx —, —NR xx —CO—NR yy —, —CH═CH— or —C≡C— in such a way that O and/or S atoms are not linked directly to one another,
having a content of multireactive mesogenic compounds plus any optional monoreactive mesogenic compounds of 30-99.9% based on the material.

2. A polymerizable LC material according to claim 1 , wherein at least one multireactive mesogenic compound has 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.

3. The polymerizable LC material according to claim 1 , wherein at least one multireactive mesogenic compound has 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, C 3-12 -aryl or heteroaryl, C 1-12 -straight chain or C 3-12 -branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, wherein one or more H atoms are optionally replaced by F or Cl,
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 and independently, 0 or 1, with z being 0 if the adjacent x or y is 0.

4. The polymerizable LC material according to claim 1 , comprising at least one monoreactive mesogenic compound, of formula MRM,
P 1 -Sp 1 -MG-R  MRM

wherein P 1 , Sp 1 and MG have the meanings as given in formula DRM,
R is F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)NR x R y , —C(═O)X, —C(═O)OR x , —C(═O)R y , —NR x R y , —OH, —SF 5 , optionally substituted silyl, C 1-12 -straight chain or C 3-12 -branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, 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.

5. The polymerizable LC material according to claim 4 , wherein at least one monoreactive mesogenic compound has 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, C 3-12 -aryl or heteroaryl, C 1-12 -straight chain or C 3-12 -branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, 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,
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 and independently, 0 or 1, with z being 0 if the adjacent x or y is 0
R 0 is 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 mono- oligo- or polyfluorinated alkyl or alkoxy with 1 to 4 C atoms,
Z 0 is —COO—, —OCO—, —CH 2 CH 2 —, —CF 2 O—, —OCF 2 —, —CH═CH—, —OCO—CH═CH—, —CH═CH—COO—, or a single bond,
A 0 is, in case of multiple occurrence independently of one another, 1,4-phenylene that is unsubstituted or substituted with 1, 2, 3 or 4 groups L, or trans-1,4-cyclohexylene,
u and v are independently of each other 0, 1 or 2,
w is 0 or 1, and
wherein the benzene and naphthalene rings can additionally be substituted with one or more identical or different groups L.

6. The polymerizable LC material according to claim 1 , comprising one or more compounds of formula ND,

wherein
U 1,2 are independently of each other

including their mirror images, wherein the rings U 1 and U 2 are each bonded to the group -(B) q - via the axial bond, and one or two non-adjacent CH 2 groups in these rings are optionally replaced by O and/or S, and the rings U 1 and U 2 are optionally substituted by one or more groups L,
L is, on each occurrence identically or differently, F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , C(CH 3 ) 3 , CH(CH 3 ) 2 , CH 2 CH(CH 3 )C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 , COC 2 H 5 , COOCH 3 , COOC 2 H 5 , CF 3 , OCF 3 , OCHF 2 , OC 2 F 5 or P-Sp-,
Q 1,2 are independently of each other CH or SiH,
Q 3 is C or Si,
B is in each occurrence independently of one another —C≡C—, —CY 1 ═CY 2 — or an optionally substituted aromatic or heteroaromatic group,
Y 1,2 are independently of each other H, F, Cl, CN or R 0 ,
q is an integer from 1 to 10,
A 1-4 are independently of each other non-aromatic, aromatic or heteroaromatic carbocyclic or heterocyclic groups, which are optionally substituted by one or more groups R 5 , and wherein each of -(A 1 -Z 1 ) m -U 1 -(Z 2 -A 2 ) n - and -(A 3 -Z 3 ) o -U 2 -(Z 4 -A 4 ) p - does not contain more aromatic groups than non-aromatic groups,
Z 1-4 are independently of each other —O—, —S—, —CO—, —COO—, —OCO—, —O—COO—, —CO—NR 0 —, —NR 0 —CO—, —NR 0 —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 ) 3 —, —(CH 2 ) 4 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —CF 2 CF 2 —, —CH═CH—, —CY 1 ═CY 2 —, —CH═N—, —N═CH—, —N═N—, —CH═CR 0 —, —C≡C—, —CH═CH—COO—, —OCO—CH═CH—, CR 0 R 00 or a singl

Assignees

• Merck Patent Gmbh

Inventors

• Choi Yong-Hyun
• Kang Jae-Hyun
• Yoon Hyun-Jin

Classifications

• C09K19/3857 Primary

  containing at least one asymmetric carbon atom · CPC title

• C08F222/26

  of unsaturated alcohols {(C08F222/1006 takes precedence)} · CPC title

• C08F2800/20

  as weight or mass percentages · CPC title

• C09K2019/0448

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

• C09K19/54 Primary

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