Dye-Doped Liquid-Crystal Medium Comprising Polymerizable Compounds

Patent metadata

Field	Value
Publication number	US-2022389321-A1
Application number	US-202217735165-A
Country	US
Kind code	A1
Filing date	May 3, 2022
Priority date	May 4, 2021
Publication date	Dec 8, 2022
Grant date	—

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

1 . An LC medium, comprising one or more polymerizable compounds of formula I
P-Sp-A a -(Z a -A b ) z -R b   I
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, 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—, 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, 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—, 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, 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—, 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 dye absorbing green light and/or at least one dye absorbing red light.

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, preferably selected from vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane and epoxy,
Sp 1 , Sp 2 , Sp 3 is a single bond or a spacer group, where, in addition, 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 , preferably —(CH 2 ) p1 —, —(CH 2 ) p1 —O—, —(CH 2 ) p1 —CO—O— or —(CH 2 ) p1 —O—CO—O—, wherein p1 is an integer from 1 to 12,
R aa is H, F, Cl, CN or straight-chain or branched alkyl having 1 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 O 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 -, particularly preferably straight-chain or branched, optionally mono- or polyfluorinated alkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms, where the alkenyl and alkynyl radicals have at least two C atoms and the branched radicals have at least three C atoms, 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, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
L′, L″ is H, F or Cl,
k is 0 or 1,
r is 0, 1, 2, 3 or 4,
s is 0, 1, 2 or 3,
t is 0, 1 or 2, and
x is 0 or 1.

3 . The LC medium according to claim 1 , comprising 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—, preferably Z 11 is —N═N— or —COO— and Z 12 is —OCO— or a single bond,
R 11 and R 12 denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy

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

• C09K19/12

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

• C09K2019/122

  Ph-Ph · CPC title

• G02F1/133514

  Colour filters · CPC title

• C09K19/601 Primary

  Azoic · CPC title