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

Patent metadata

Field	Value
Publication number	US-9776952-B2
Application number	US-201615016885-A
Country	US
Kind code	B2
Filing date	Feb 5, 2016
Priority date	Mar 9, 2010
Publication date	Oct 3, 2017
Grant date	Oct 3, 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. Compounds of the formula I
P a -(Sp a ) s1 -A 2 -CH 2 CH 2 -A 1 -CH 2 C 2 -A 3 -(Sp b ) s2 -P b   I

wherein 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 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, in addition, 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, preferably 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,

where, in addition, 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, F denotes, 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 preferably denote H, F, Cl, CN, OCF 3 or CF 3 ,
and in which one or more of the radicals A 1 , A 2 and A 3 are selected from the group d) 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, preferably in which one or more of the radicals A 1 , A 2 and A 3 are 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,

where, in addition, 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.

2. Compounds of the formula IA
G-O-(Sp a ) s1 -A 2 -CH 2 CH 2 -A 1 -CH 2 CH 2 -A 3 -(Sp b ) s2 -O-G′  IA

wherein Sp a , Sp b , A 1 , A 2 , A 3 , s1 and s2 have the following meaning,
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 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, in addition, 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, preferably 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,

where, in addition, 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, and

G and G′ each, independently of one another, denote an H atom or a protecting group.

3. The compounds of formula I of claim 1 wherein, A 1 is selected from a group consisting of:

4. The compounds of formula IA of claim 2 wherein, A 1 is selected from a group consisting of:

Assignees

• Merk Patent Ges Mit Beschrankter Haftung
• Merck Patent Gmbh

Inventors

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

Classifications

• C09K2019/3408

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

• C09K19/542

  Macromolecular compounds · CPC title

• C09K2019/2042

  Ph-Ph-COO-Ph · CPC title

• C09K2019/3422

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

• C09K19/46

  containing esters · CPC title