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

Patent metadata

Field	Value
Publication number	US-9347000-B2
Application number	US-201414469084-A
Country	US
Kind code	B2
Filing date	Aug 26, 2014
Priority date	Apr 26, 2010
Publication date	May 24, 2016
Grant date	May 24, 2016

Abstract

The present invention relates to polymerisable 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-stabilised blue phase, and in LC media for LC displays of the PS or PSA (“polymer sustained” or “polymer sustained alignment”) type, and to LC media and LC displays comprising these compounds.

First claim

The invention claimed is:

1. A compound of formula I
P a -(Sp a ) s1 -A 2 -Q 1 -A 1 -Q 2 -A 3 -(Sp b ) s2 -P b   I

in which
P a , P b each, independently of one another, denote an acrylate group,
Sp a , Sp b each, independently of one another, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
Q 1 , Q 2 each, independently of one another, denote —CF 2 O— or —OCF 2 —,
A 1 denotes

 in which the individual rings are optionally mono- or polysubstituted by L,
A 2 , A 3 each, independently of one another, denote
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4′-bicyclohexylene, in which optionally one or more non-adjacent CH 2 groups are replaced by —O— and/or —S—, and in which one or more H atoms are optionally replaced by F,
b) 1,4-phenylene or 1,3-phenylene, in which optionally one or two CH groups are replaced by N and in which one or more H atoms are optionally replaced by L,
c) 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 or selenophene-2,5-diyl, each of which is optionally mono- or polysubstituted by L,
d) a saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radical having 5 to 20 cyclic C atoms, one or more of which are optionally replaced by heteroatoms,

and wherein one of the following provisos A, B or C is satisfied
A) one or more of the radicals A 2 and A 3 are 1,3-phenylene, in which one or two CH groups are optionally replaced by N and in which optionally one or more H atoms are optionally replaced by L, or
B) one or more of the radicals A 2 and A 3 are a saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radical having 5 to 20 cyclic C atoms, one or more of which may also be replaced by heteroatoms, or
C) A 1 denotes

in which the individual rings are optionally mono- or polysubstituted by L,
L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 or a straight-chain or branched, in each case optionally fluorinated alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms.

2. A LC medium comprising one or more compounds of formula I according to claim 1 and one or more further liquid-crystalline compounds.

3. A LC display containing one or more compounds of formula I according to claim 1 .

4. A compound according to claim 1 , wherein
A 2 , A 3 each, independently of one another, denote
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4′-bicyclohexylene, in which optionally one or more non-adjacent CH 2 groups are replaced by —O— and/or —S—, and in which one or more H atoms are optionally replaced by F,
b) 1,4-phenylene or 1,3-phenylene, in which optionally one or two CH groups are replaced by N and in which one or more H atoms are optionally replaced by L,
c) 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 or selenophene-2,5-diyl, each of which is optionally mono- or polysubstituted by L,
d) 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 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 are optionally replaced by N,

L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 or a 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 a straight-chain or branched alkyl having 1 to 12 C atoms, in which one or more H atoms are optionally replaced by F,
M denotes —O—, —S—, —CH 2 —, —CHY 1 — or —CY 1 Y 2 —, and
Y 1 and Y 2 each, independently of one another, denote H, F, OCF 3 , Cl, CN or a straight-chain or branched alkyl having 1 to 12 C atoms, in which one or more H atoms are optionally replaced by F.

5. A compound according to claim 4 , wherein
Y 1 and Y 2 each, independently of one another, denote H, F, Cl, CN, OCF 3 or CF 3 , wherein only one of Y 1 and Y 2 may be OCF 3 .

6. A compound according to claim 1 , wherein
Sp a , Sp b each, independently of one another, denote alkylene having 1 to 20, which is optionally mono- or polysubstituted by F, Cl, Br, I or CN, and in which one or more non-adjacent CH 2 groups are optionally each replaced, independently of one another, by —O—, —S—, —NH—, —Si(R 00 *R 000 *)—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —S—CO—, —CO—S—, —N(R 00 *)—CO—O—, —O—CO—N(R 00 *)—, or —N(R 00 *)—CO—N(R 00 *)—, in such a way that O and/or S atoms are not linked directly to one another, and
R 00 * and R 000 * each, independently of one another, denote H or alkyl having 1 to 12 C atoms.

7. A compound according to claim 1 , to which proviso A) applies, and A 1 denotes

in which the individual rings are optionally mono- or polysubstituted by L, and wherein L is not CF 2 H or CF 3 for A 1 .

8. A compound according to claim 1 , to which proviso B) applies, and A 1 denotes

in which the individual rings are optionally mono- or polysubstituted by L, and wherein L is not CF 2 H or CF 3 for A 1 .

9. A compound according to claim 1 , wherein the spacer is an alkylene group.

10. A LC display having a blue phase, comprising a compound of formula I or a polymer obtainable by polymerization of said compound
P a -(Sp a ) s1 -A 2 -A 2 -Q 1 -A 1 Q 2 -A 3 -(Sp b ) s2 -P b   I

in which
P a , P b each, independently of one another, denote an acrylate group,
Sp a , Sp b each, independently of one another, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
Q 1 , Q 2 each, independently of one another, denote —CF 2 O— or —OCF 2 —,
A 1 , A 2 , A 3 each, independently of one another, denote
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4′-bicyclohexylene, in which optionally one or more non-adjacent CH 2 groups are replaced by —O— and/or —S—, and in which one or more H atoms are optionally replaced by F,
b) 1,4-phenylene or 1,3-phenylene, in which optionally one or two CH groups are replaced by N and in which one or more H atoms are optionally replaced by L,
c) 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 or selenophene-2,5-diyl, each of which is optionally mono- or polysubstituted by L,
d) a saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radical having 5 to 20 cyclic C atoms, one or more of which may also be replaced by heteroatoms,

and in which one or more of the radicals A 1 , A 2 and A 3 satisfies one of the following provisos A or B
A) 1,3-phenylene, in which one or two CH groups are optionally replaced by N and in which one or more H atoms are optionally replaced by L, or
B) a saturated, partially unsatura

Assignees

• Merck Patent Gmbh

Inventors

• Jansen Axel
• Taugerbeck Andreas
• Haensel Helmut
• Goetz Achim

Classifications

• C09K2019/3422

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

• C09K19/42

  Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 · CPC title

• C09K19/0275 Primary

  Blue phase · CPC title

• C09K19/46

  containing esters · CPC title

• C09K2019/0481

  Phenylene substituted in meta position · CPC title