Polymerisable compound, polymerisable LC material and polymer film

Patent metadata

Field	Value
Publication number	US-12570900-B2
Application number	US-202218698640-A
Country	US
Kind code	B2
Filing date	Oct 10, 2022
Priority date	Oct 11, 2021
Publication date	Mar 10, 2026
Grant date	Mar 10, 2026

Abstract

A polymerisable liquid crystal (LC) compound, a corresponding polymerizable LC material, a polymer film with flat, negative, or positive optical dispersion obtainable from such a material, and the use of the polymerisable LC, polymerisable LC material and/or polymer film in optical, electro optical, electronic, semiconducting, or luminescent components or devices.

First claim

The invention claimed is:

1 . A polymerisable LC material comprising
i) a compound of formula T,
R T1 -(A T1 -Z T1 ) m1 -G T1 -(Z T2 -A T2 ) m2 -R T2   T

wherein R T1 and R T2 each and independently from another denote H or a hydrocarbon group having 1 to 20 carbon atoms, wherein the group may have a substituent group, and any carbon atom of the group may be substituted with a heteroatom, and at least one of R T1 and R T2 denotes P-SP-, P denotes a polymerizable group, Sp denotes a spacer group, A T1 and A T2 each and independently and in each occurrence denote a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, whereby these groups may be unsubstituted or may be substituted with one or more of substituent groups L, L denotes each and independently in each occurrence F, Cl, Br, I, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 —or two or more non-adjacent —CH 2 —may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, -CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and any hydrogen atom in the alkyl group may be substituted by F, or L may denote a group represented by P-Sp-, Z T1 and Z T2 each and independently denotes —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, -CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO —CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO —CH 2 —, —OCO —CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, G T1 denotes a group

Ch each and independently denotes a chalcogen,
R 0 and R 00 each independently represent a hydrogen atom, F, Cl, Br, I, or a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 —or two or more non-adjacent —CH 2 —may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, -CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and any hydrogen atom in the alkyl group may be substituted with F or Cl,
m1 and m2 each independently represent an integer of 1 to 6, and
W 1 and/or W 2 each independently denotes a group
-(Z T3 -A T3 -) m3 -A T4 -Y
wherein
Z T3 denotes —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO —CH 2 CH 2 —, —OCO —CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO —CH 2 —, —OCO —CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond,
A T3 and A T4 independently and in each occurrence denote a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, whereby each of these groups may optionally be unsubstituted or may optionally be substituted with one or more of substituent groups L,
m3 denotes 0, 1, or 2, and
Y denotes F, Cl, Br, I, a pentafluoro-sulfuranyl group, a nitro group, a Y cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 —or two or more non-adjacent —CH 2 —are each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, -CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and in which any hydrogen atom in the alkyl group may optionally be substituted with F, or Y may represent a group represented by P-Sp-, and
ii) one or more monoreactive mesogenic compounds selected from the following formulae:

wherein
P 0 denotes, in case of multiple occurrences independently of one another, a polymerisable group (P),
L denotes each and independently in each occurrence F, Cl, Br, I, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 —or two or more non-adjacent —CH 2 —are each optionally and independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, -CO—S—, —S—CO—, —O—CO-O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and in which any hydrogen atom in the alkyl group may optionally be substituted by F, or L may denote a group represented by P-Sp—
r denotes 0, 1, 2, 3, or 4,
x and y independently of each other, denote 0 or identical or different integers from 1 to 12,
z each and independently, denotes 0 or 1, with z being 0 if the adjacent x or y is 0,
R 0 denotes alkyl, alkoxy, thioalkyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy with 1 or more C atoms or denotes Y 0 ,
Y 0 denotes F, Cl, CN, NO 2 , OCH 3 , OCN, SCN, SF 5 , or mono-, oligo-or polyfluorinated alkyl or alkoxy with 1 to 4 C atoms,
Z 0 denotes —COO—, —OCO—, —CH 2 CH 2 —, —CF 2 O—, —OCF 2 —, —CH═CH—, —OCO—CH═CH—, —CH═CH—COO—, or a single bond,
A 0 denotes, in case of multiple occurrences independently of one another, 1,4-phenylene that is unsubstituted or substituted with 1, 2, 3, or 4 groups L, or trans-1,4-cyclohexylene,
u and v independently of each other denote 0, 1, or 2,
w denotes 0 or 1, and
wherein the benzene and naphthalene rings can additionally be substituted with one or more identical or different substituent groups L.

2 . The polymerisable LC material according to claim 1 , wherein A T1 to A T4 in formula T each independently and in each occurrence denote a group selected from formulae A-1 to A-11,

wherein,
L denotes each and independently in each occurrence F, Cl, Br, I, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto g

Assignees

• Merck Patent Gmbh

Inventors

• Adlem Kevin
• Heeney Martin
• Allen James

Classifications

• C09K2019/0448

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

• C09K19/38

  Polymers · CPC title

• C09K19/3491 Primary

  having sulfur as hetero atom · CPC title