Polymerisable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-10995273-B2
Application number	US-201715834518-A
Country	US
Kind code	B2
Filing date	Dec 7, 2017
Priority date	Dec 8, 2016
Publication date	May 4, 2021
Grant date	May 4, 2021

Abstract

Polymerisable compounds, processes and intermediates for the preparation thereof, liquid-crystal (LC) media comprising them, and 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

The invention claimed is:

1. A liquid crystal (LC) medium comprising:
one or more compounds of the formula I:

wherein the individual radicals, independently of each other, and on each occurrence identically or differently, have the following meanings
P is a methacrylate group or an acrylate group, wherein both groups P have the same meaning,
Sp is a single bond or —(CH 2 ) p1 —, —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 —, or —CO—O—(CH 2 ) p1 —, wherein p1 is 2, 3, 4, 5 or 6, and, if Sp is —O—(CH 2 ) p1 —, —O—CO—(CH 2 ) p1 — or —CO—O—(CH 2 ) p1 — the O-atom or CO-group, respectively, is linked to the benzene ring,
L 11 , L 12 are F, Cl or OR,
R is straight-chain or branched alkyl with 1 to 4 C atoms that is optionally fluorinated,
L 13 , L 14 are F, Cl, —CN 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 F or Cl,
r1, r2 are 0, 1, 2, 3 or 4, wherein r1+r2≥2,
r3, r4 are 0, 1, 2, 3 or 4, wherein r1+r3≤4 and r2+r4≤4,
wherein the compounds contain at least one group L 11 or L 12 that is F or Cl, and at least one group L 11 or L 12 that is OR, and
with the proviso that the following compounds are excluded

wherein P, Sp, L 11 and L 12 are as defined above;

one or more compounds of the formulae CY and/or PY:

in which the individual radicals have the following meanings:
a denotes 1 or 2,
b denotes 0 or 1,

 denotes

R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another,
Z x denotes —CH═CH—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —O—, —CH 2 —, —CH 2 CH 2 — or a single bond,
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F, CHF 2 ;

one or more compounds of the formula ZK

in which the individual radicals have the following meanings:

 denotes

 denotes

R 3 and R 4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another,
Z y denotes —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF— or a single bond; and

provided that the medium comprises at least one compound selected from compounds of the following formulae CY1, CY2, CY9, CY10, PY1, PY2, PY9, PY10, ZK1, AN1 and T2:

wherein
alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms,
alkenyl denotes a straight-chain alkenyl radical having 2-7 C atoms,
R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms,
(O) denotes an oxygen atom or a single bond, and
m denotes an integer from 1 to 6.

2. The LC medium of claim 1 , wherein the compound of formula I is selected from the following subformulae:

wherein P, Sp, R, L 11 , L 12 , L 13 , L 14 , r2, r3, r4 have the meanings given in claim 1 , r5 is 0, 1, 2 or 3, r3+r5≤3, and r2+r5 is ≥1.

3. The LC medium of claim 1 , wherein the compound of formula I is selected from the following subformulae:

wherein P, Sp and R have the meanings given in claim 1 and L′ is F or Cl.

4. The LC medium of claim 1 , wherein the compound of formula I is selected from the following subformulae:

wherein P and R have the meanings given in claim 1 , L′ is F or Cl and Sp has one of the meanings given in claim 1 which is different from a single bond.

5. The LC medium of claim 1 , wherein the compound of formula I is selected from the following subformulae:

6. The LC medium according to claim 3 , wherein, in the formulae, R is CH 3 and L′ is F.

7. The LC medium according to claim 1 , which further comprises one or more compounds selected from the following formulae:

in which the individual radicals, on each occurrence identically or differently, each, independently of one another, have the following meaning:

R A1 alkenyl having 2 to 9 C atoms or, if at least one of the rings X, Y and Z denotes cyclohexenyl, also one of the meanings of R A2 ,
R A2 alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another,
Z x —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —CF═CF—, —CH═CH—CH 2 O—, or a single bond
L 1-4 each, independently of one another, H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 H,
x 1 or 2,
z 0 or 1.

8. The LC medium according to claim 1 , wherein the compounds of formula I are polymerised.

Assignees

• Merck Patent Gmbh

Inventors

• Ushakov Dmitry
• DEING Kaja Christina

Classifications

• G02F2202/022

  polymeric · CPC title

• G02F1/137

  characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering · CPC title

• G02F1/13471

  in which all the liquid crystal cells or layers remain transparent, e.g. FLC, ECB, DAP, HAN, TN, STN, SBE-LC cells (G02F1/13475 takes precedence) · CPC title

• C09K19/44

  containing compounds with benzene rings directly linked · CPC title

• C09K19/12 Primary

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