Polymerisable Compounds and the Use thereof in Liquid-Crystal Displays

Patent metadata

Field	Value
Publication number	US-2021348056-A1
Application number	US-201917273824-A
Country	US
Kind code	A1
Filing date	Sep 3, 2019
Priority date	Sep 6, 2018
Publication date	Nov 11, 2021
Grant date	—

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 type.

First claim

1 . A compound of formula I
P-Sp-A 1 -(Z 1 -A 2 ) z -R b   I
wherein the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings P a polymerisable group, Sp a spacer group which is optionally substituted by P, or a single bond, A 1 , A 2 benzene or naphthalene, which are optionally substituted by one or more groups L, L 9 , L 10 or P-Sp-, Z 1 —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 H or alkyl having 1 to 12 C atoms, R b F, Cl, —CN, P-Sp- or straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —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, L 9 F or Cl, L 10 —CH 2 —O-A, A alkyl with 1 to 6 C atoms, L F, Cl, —CN, P-Sp- or straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —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, n11, 2, 3 or 4, characterized in that the compounds contain at least one group A 1 or A 2 that is substituted by at least one group L 9 , and at least group A 1 or A 2 that is substituted by at least one group L 10 , wherein the groups L 9 and L 10 may be attached to the same or different rings A 1 or A 2 .

2 . The compound according to claim 1 , characterized in that -A1-(Z 1 -A 2 ) z - is selected from the following subformulae

wherein at least one benzene ring is substituted by at least one group L 9 and at least one benzene ring is substituted by at least one group L 10 , and the benzene rings are optionally further substituted by one or more groups L, L 9 , L 10 or P-Sp- as defined in claim 1 .

3 . The compound according to claim 1 , characterized in that it is selected from the following subformulae:

wherein the individual radicals, independently of each other, and on each occurrence identically or differently, have the following meanings
A, P, Sp, R b one of the meanings given in claim 1 ,
L 11 , L 12 , L 13 F, Cl or —CH 2 —O-A,
L 14 , L 15 , L 16 L 11 , F, Cl, —CN, P-Sp- or straight chain, branched or cyclic alkyl having 1 to 6, C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —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,
r1, r2, r30, 1 or 2, wherein r1+r2+r3≥2,
r4, r5, r60, 1 or 2,
r7, r80, 1 or 2,
r9, r100, 1 or 2,
wherein r7+r9≤3, r8+r10≤3, in formula I3 r7+r8≥2, and in formula I4a and I4b r1+r7+r8≥2, and
wherein the compounds contain at least group L 11 , L 12 or L 13 that is F or Cl and at least one group L 11 , L 12 or L 13 that is —CH 2 —O-A.

4 . The compound according to claim 3 , which is selected from the following subformulae:

wherein Sp(P) 2 denotes a spacer group Sp that is substituted by two polymerisable groups P at identical or different positions, wherein r7+r9≤3, r8+r10≤3, in formula I3 r7+r8≥2, and in formula I4A to I4E r1+r7+r8≥2, and wherein the compounds contain at least group L 11 , L 12 or L 13 that is F or Cl, preferably F, and at least one group L 11 , L 12 or L 13 that is —CH 2 —O-A.

5 . The compound according to claim 4 , which is selected from the following subformulae:

wherein L has one of the meanings given for L 14 and r is 0, 1 or 2.

6 . The compound according to claim 4 characterized in that it is selected from the following subformulae:

wherein Sp′ and Sp″ have one of the meanings given for Sp, and L x is H, F, —CH 2 —O—C 2 H 5 or —CH 2 —O—CH 3 .

7 . The compound according to claim 1 , characterized in that it is selected from the following subformulae:

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Bremer Matthias
• Becker Patricia
• Kietzke Elizabeth Lekha
• Schmidt Marcel

Classifications

• C09K2019/3009

  Cy-Ph · CPC title

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title

• C09K19/322

  Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring · CPC title

• C09K2019/0448

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

• C09K19/04 Primary

  characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} · CPC title