Polymerisable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-11739266-B2
Application number	US-201917299975-A
Country	US
Kind code	B2
Filing date	Dec 4, 2019
Priority date	Dec 7, 2018
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

The present invention relates to polymerisable compounds, to processes and intermediates for the preparation thereof, to liquid-crystal (LC) media comprising them, and to the use of the polymerisable compounds and LC media for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the polymer sustained alignment (PS, PSA) and self-aligning (SA) type.

First claim

The invention claimed is:

1. A compound of formula I
P-Sp-A 1 -(Z 1 -A 2 ) z -R b   I

wherein
R b is P-Sp- or R,
R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms or a branched alkyl or a cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by -O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by F or Cl,
P is a polymerisable group,
Sp is a spacer group which is optionally substituted by P, or is a single bond,
A 1 , A 2 each independently denotes benzene, naphthalene, phenanthrene, anthracene, dibenzofuran or dibenzothiophene, all of which are optionally substituted by one or more groups A, L or P-Sp-, and wherein at least one group A 1 or A 2 is substituted by at least one group A,
Z 1 is —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—CO—O—, —O—CO—, —CH═CH—, —CH 2 —CH 2 —CO—O—, —O—CO—CH 2 —CH 2 —, —CR 0 R 00 —, or a single bond,
R 0 , R 00 each independently denotes H or alkyl having 1 to 12 C atoms,
A is alkenyl with 3 to 7 C-atoms,

L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or a branched alkyl or a cyclic alkyl having 3 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are each optionally replaced by P-Sp-, F or Cl,
z 0, 1, 2 or 3, and
n1 1, 2, 3 or 4.

2. The compound according to claim 1 , wherein A is —CH═CH 2 , —CH 2 —CH═CH 2 , —CH═CH—CH 3 , —CH═CH—CH═CH 2 or —C(CH 3 )═CH 2 .

3. The compound according to claim 1 , wherein -A 1 -(Z 1 -A 2 ) z - denotes benzene, biphenylene, p-terphenylene (1,4-diphenylbenzene), m-terphenylene (1,3-diphenylbenzene), naphthylene, 2-phenyl-naphthylene, phenanthrene or anthracene, dibenzofuran or dibenzothiophene, all of which are optionally substituted by one or more groups A, L or P-Sp- and are at least monosubstituted by A.

4. The compound according to claim 1 , wherein -A 1 -(Z 1 -A 2 ) z - is selected from the following formulae

wherein the rings are optionally further substituted by one or more groups A, L or P-Sp- as defined for formula I, and at least one ring is substituted by at least one group A.

5. The compound according to claim 1 , which is selected from the following formulae

wherein
A, P, Sp, R b each have one of the meanings given for formula I,
L 11 , L 12 , L 13 each independently denotes L or A,
r1, r2, r3 0, 1, 2, 3 or 4, wherein r1+r2+r3≥1,
r4, r5 0, 1, 2 or 3, wherein in formula I3 r4+r5 ≥1 and in formula I4a and I4b r1+r4+r5≥1,
wherein the compound I1, I2, I3, I4a, I4b or I5 contain at least group L 11 , L 12 or L 13 that is A.

6. The compound according to claim 5 , which is selected from the following formulae

wherein
Sp, L 11-13 and r1-r5 each independently have the meanings given for formula I,
Sp(P) 2 denotes a spacer group Sp that is substituted by two polymerisable groups P at identical or different positions,
wherein r1+r2+r3≥1, in formula I3 r4+r5≥1, and in formula I4A to I4E r1+r4+r5≥1, and
wherein the compounds contain at least group L 11 , L 12 or L 13 that is A.

7. The compound according to claim 1 , which is selected from the following formulae

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Fortte Rocco
• Haensel Helmut
• Plummer Edward
• Uebel Timo
• Heppert Oliver

Classifications

• C09K19/12 Primary

  at least two benzene rings directly linked, e.g. biphenyls · CPC title

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• C09K2019/0448

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

• C09K2019/122

  Ph-Ph · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title