Polymerisable compounds and the use thereof in liquid-crystal media and liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-9567285-B2
Application number	US-201113583435-A
Country	US
Kind code	B2
Filing date	Feb 24, 2011
Priority date	Mar 9, 2010
Publication date	Feb 14, 2017
Grant date	Feb 14, 2017

Abstract

The present invention relates to polymerizable compounds, to processes and intermediates for the preparation thereof, to the use thereof for optical, electro-optical and electronic purposes, in particular in liquid-crystal (LC) media and LC displays having a polymer-stabilized blue phase, and in LC media for LC displays of the PS or PSA type (“polymer sustained” or “polymer sustained alignment”), and to LC media and LC displays comprising these compounds.

First claim

The invention claimed is:

1. A liquid crystal display containing one or more compounds of the formula I
P a -(Sp a ) s1 -A 2 -CH 2 CH 2 -A 1 -CH 2 CH 2 -A 3 -(Sp b ) s2 -P b   I

in which the individual radicals have the following meaning
P a P b each, independently of one another, denote a polymerisable group,
Sp a , Sp b on each occurrence, identically or differently, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
A 1 , A 2 , A 3 each, independently of one another, denote a radical selected from the following groups
a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and 4,4′-bicyclohexylene, wherein one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S—, and wherein, one or more H atoms may be replaced by F,
b) the group consisting of 1,4-phenylene wherein one or two CH groups may be replaced by N wherein one of more H atoms are replaced by L and 1,3-phenylene, wherein one or two CH groups may be replaced by N and wherein, one or more H atoms may be replaced by L,
c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobut-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may be mono- or polysubstituted by L,
d) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may also be replaced by heteroatoms, selected from the group consisting of bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]-octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl,

wherein one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N,

L on each occurrence, identically or differently, denotes, F, Cl, CN, SCN, SF 5 or straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
R 0 , R 00 each, independently of one another, denote H, F or straight-chain or branched alkyl having 1 to 12 C atoms, wherein, one or more H atoms may be replaced by F,
M denotes —O—, —S—, —CH 2 —, —CHY— or —CY 1 Y 2 —,
Y and Y 1 each, independently of one another, have one of the meanings indicated above for R 0 , or denote Cl or CN,
or a polymer obtainable by polymerisation of one or more compounds of the formula I and
wherein the liquid crystal display exhibits a blue phase.

2. A liquid-crystal (LC) medium comprising one or more compounds of formula I, and optionally additionally one or more polymerisable compounds and/or one or more liquid-crystalline compounds, or comprising a polymer obtainable by polymerisation of one or more compounds according to formula I
P a -(Sp a ) s1 -A 2 -CH 2 CH 2 -A 1 -CH 2 CH 2 -A 3 -(Sp b ) s2 -P b   I

in which the individual radicals have the following meaning
P a P b each, independently of one another, denote a polymerisable group,
Sp a , Sp b on each occurrence, identically or differently, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
A 1 , A 2 , A 3 each, independently of one another, denote a radical selected from the following groups
a) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and 4,4′-bicyclohexylene, wherein one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and wherein one or more H atoms may be replaced by F,
b) the group consisting of 1,4-phenylene wherein one or two CH groups may be replaced by N in which one of more H atoms are replaced by L, and 1,3-phenylene, wherein one or two CH groups may be replaced by N and wherein one or more H atoms may be replaced by L,
c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobut-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl and selenophene-2,5-diyl, each of which may, be mono- or polysubstituted by L,
d) the group consisting of saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may also be replaced by heteroatoms, selected from the group consisting of bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]-octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl,

wherein one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N,

L on each occurrence, identically or differently, denotes, F, Cl, CN, SCN, SF 5 or straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms,
R 0 , R 00 each, independently of one another, denote H, F or straight-chain or branched alkyl having 1 to 12 C atoms, wherein one or more H atoms may be replaced by F,
M denotes —O—, —S—, —CH 2 —, —CHY— or —CY 1 Y 2 —,
Y and Y 1 each, independently of one another, have one of the meanings indicated above for R 0 , or denote Cl or CN, and
wherein the medium exhibits a blue phase.

3. LC medium according to claim 2 , characterised in that it comprises the following components
a polymerisable component A comprising one or more compounds according to formula I, and
a liquid-crystalline component B comprising one or more compounds of the formula II

in which the individual radicals have the following meaning
R 22 denotes H, F, Cl, CN, NCS, SF 5 , SO 2 CF 3 or straight-chain or branched alkyl having 1 to 20 C atoms, which is unsubstituted or mono- or polysubstituted by F, Cl or CN, and wherein one or more non-adjacent CH 2 groups may also each be replaced, independently of one another, by —O—, —S—, —NH—, —NR 01 —, —SiR 01 R 02 —, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S—, —CY 01 ═CY 01 — or —C≡C— in such a way that O and/or S atoms are not linked directly to one another,
Y 01 , Y 02 each, independently of one another, denote F, Cl or CN, the radicals Y 01 and Y 02 also denote H,
R 01 , R 02 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
A 21 , A 22 , A 23 each, independently of one another and on each occurrence identically or differently denote

Z 21 , Z 22 each, independently of one another and on each occurrence identically or differently, denote a single bond, —(CH 2 ) 4 )—, —CH 2 CH 2 —, —CF 2 —CF 2 —, —CF 2 —CH 2 —, —CH 2 —CF 2 —, —CH═CH—, —CF═CF—, —CF═CH—, —(CH 2 ) 3 O—, —O(CH 2 ) 3 —, —CH═CF—, —C≡C—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —CO—O— or —O—CO—,
X 22 denotes F, Cl, —CN, —NCS, —SF 5 , —SO 2 CF 3 , or alkyl, alkenyl, alkenyloxy, alkylalkoxy or alkoxy having 1 to 3 C atoms, which is mono- or polysubstituted by F, Cl or CN,
L 21 , L 22 each independently of one another, denote H or F,
m denotes 0, 1 or 2,
n denotes 0, 1, 2 or 3,
o denotes 0, 1 or 2, where
m+n+o denotes 0, 1, 2 or 3,
optionally

Assignees

• Jansen Axel
• Kodek Thorsten
• Haensel Helmut
• Durmaz Erdal
• Merck Patent Gmbh

Inventors

• Jansen Axel
• Kodek Thorsten
• Haensel Helmut
• Durmaz Erdal

Classifications

• C09K19/16

  the chain containing carbon-to-carbon double bonds, e.g. stilbenes · CPC title

• C09K2019/3425

  Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title

• C09K2019/3408

  Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems · CPC title

• C09K19/542

  Macromolecular compounds · CPC title

• C09K2019/3422

  the heterocyclic ring being a six-membered ring · CPC title