Dye-doped liquid-crystal medium comprising polymerizable compounds

Patent metadata

Field	Value
Publication number	US-12227688-B2
Application number	US-202217735165-A
Country	US
Kind code	B2
Filing date	May 3, 2022
Priority date	May 4, 2021
Publication date	Feb 18, 2025
Grant date	Feb 18, 2025

Abstract

A liquid-crystal (LC) medium containing one or more dyes and one or more polymerizable compounds, its use for optical, electro-optical and electronic purposes, in particular in LC displays, especially in colour LC displays of the PSA (polymer sustained alignment) or SA (self-aligning) mode containing a quantum dot colour filter (QDCF), an LC display of the PSA or SA mode containing the LC medium and containing a QDCF, and to a process of manufacturing the LC display.

First claim

The invention claimed is:

1. An LC medium, comprising
0.01 to 3.0% by weight of one or more polymerizable compounds of formula I
P-Sp-A a -(Z a -A b ) z -R b
wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
R b is P-Sp- or R,
R is F, Cl, —CN or a straight chain alkyl having 1 to 25 C atoms or branched or 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—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—

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 or P-Sp-,

P is a polymerizable group,
Sp is a spacer group which is optionally substituted by P, or is a single bond,
A a , A b is an alicyclic, heterocyclic, aromatic or heteroaromatic group with 4 to 20 ring atoms, which is monocyclic or polycyclic and which is optionally substituted by one or more groups L or P-Sp-,
Z a 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 is H or alkyl having 1 to 12 C atoms,
L is F, Cl, —CN, P-Sp- or a straight chain alkyl having 1 to 25 C atoms or branched or 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—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—

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 is 0, 1, 2, 3 or 4,
n1 is 1, 2, 3 or 4,
and further comprising one or more compounds of formula II

wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings
R 1 , R 2 is H or a straight chain alkyl having 1 to 25 C atoms or branched or 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—, —O—CO—O—, CR 0 ═CR 00 —, —C≡C—,

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 CN, CF 3 , F or Cl,

A 1 , A 2 is selected from the following formulae

Z 1 , Z 2 is —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O— or a single bond,
L 1 , L 2 , L 3 , L 4 is F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 ,
Y H, F, Cl, CF 3 , CHF 2 or CH 3 ,
L C CH 3 or OCH 3 ,
a1 0, 1 or 2, and
a2 0 or 1,
and further comprising at least one dichroic dye absorbing green light and/or at least one dichroic dye absorbing red light,
wherein the LC comprises one or more dichroic dyes of formulae I*

wherein each of the individual radicals, independently of each other and on each occurrence identically or differently, have the following meanings

are independently of each other

and, in case i is 2 or more, the terminal

may also be

and, in case j is 2 or more, the terminal

may also be

Z 11 and Z 12 denote a single bond, —N═N—, —OCO— or —COO—,
R 11 and R 12 denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy with 1 to 20 C-atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl with 2 to 20 C-atoms, or alkylaminyl, dialkylaminyl, alkylcarbonyl, alkyloxycarbonyl, alkylcarbonyloxy or alkyloxycarbonyloxy with 3 to 20 C-atoms, or alkylcyclohexylalkyl with 8 to 25 C-atoms,
i and j are independently of each other 1, 2, 3 or 4.

2. The LC medium according to claim 1 , comprising one or more polymerizable compounds of formula I selected from the following formulae:

in which each of the individual radicals, on each occurrence identically or differently, and each, independently of one another, have the following meaning:
P 1 , P 2 , P 3 is a polymerizable group,
Sp 1 , Sp 2 , Sp 3 is a single bond or a spacer group, where one or more of the radicals P 1 -Sp 1 -, P 2 -Sp 2 - and P 3 -Sp 3 - may denote R aa , with the proviso that at least one of the radicals P 1 -Sp 1 -, P 2 -Sp 2 and P 3 -Sp 3 -present is different from R aa ,
R aa is H, F, Cl, CN or straight-chain alkyl having 1 to 25 C atoms or branched alkyl having 3 to 25 C atoms, in which one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 0 )═C(R 00 )—, —C≡C—, —N(R 0 )—, —O—, —S—, —CO—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that 0 and/or S atoms are not linked directly to one another, and in which one or more H atoms may be replaced by F, Cl, CN or P 1 -Sp 1 -, and wherein R aa does not denote or contain a group P 1 , P 2 or P 3 ,
R 0 , R 00 is H or alkyl having 1 to 12 C atoms,
R y , R z is H, F, CH 3 or CF 3 ,
Z M1 is —O—, —CO—, —C(R y R z )— or —CF 2 CF 2 —,
Z M2 , Z M3 is —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 — or —(CH 2 ) n —, where n is 2, 3 or 4,
L is F, Cl, CN or a straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, or a straight-chain, optionally mono- or polyfluorinated alkenyl or alkynyl having 2 to 12 C atoms, or a branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 12 C atoms,
L′, L″ is H, F or Cl,
k is 0 or 1,
r is 0, 1

Assignees

• Merck Patent Gmbh

Inventors

• Bae Hyun-Woo
• Lee Jung-Min
• Yoon Hyun-Jin
• Yun Yong-Kuk

Classifications

• G02F2202/36

  Micro- or nanomaterials · CPC title

• G02F1/1341

  Filling or closing of cells · CPC title

• G02F1/133617

  Illumination with ultraviolet light; Luminescent elements or materials associated to the cell · CPC title

• G02F1/133365

  Cells in which the active layer comprises a liquid crystalline polymer · CPC title

• C09K2019/0448

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