Polymerizable compounds and their use in liquid crystal media and liquid crystal displays

Patent metadata

Field	Value
Publication number	US-9315729-B2
Application number	US-201214122333-A
Country	US
Kind code	B2
Filing date	May 15, 2012
Priority date	May 27, 2011
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

The present invention relates to polymerizable compounds, liquid-crystalline media comprising the compounds, in particular liquid-crystal (LC) media and LC displays having a polymer-stabilised blue phase, and LC media for LC displays of the PS or PSA type (“polymer sustained” or “polymer sustained alignment”) type.

First claim

The invention claimed is:

1. A compounds of formula I
P a -(Sp a ) s1 -(A 1 -Z 1 ) n1 -A 2 -Q 1 -A 3 -(Z 4 -A 4 ) n2 -(Sp b ) s2 -P b   I

in which the individual radicals have the following meanings:
P a denotes a polymerisable group,
P b denotes a polymerisable group, H or F,
Sp a , Sp b each, independently of one another, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
n1 denotes 0 or 1,
n2 denotes 0,
Q 1 denotes —CF 2 O—,
Z 1 , Z 4 each, independendently of one another, denote a single bond, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CO)O—, —O(CO)—, —(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—, —O—, —CH 2 —, —(CH 2 ) 3 —, or —CF 2 —,
where Z 1 and Q 1 or Z 4 and Q 1 do not simultaneously denote —CF 2 O—,

A 2 denotes

A 3 denotes

and
A 1 , A 4
each, independently of one another, denotes a radical selected from the following groups:
a) the group consisting of 1,4-phenylene and 1,3-phenylene, in which, in addition, one or two CH groups may each be replaced by N and in which, in addition, one or more H atoms may each be replaced by L,
b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexenylene and 1,4′-bicyclohexylene, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced by —O— or —S— and in which, in addition, one or more H atoms may each be replaced by F or Cl,
c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-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, and
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,
where, in addition, one or more H atoms in these radicals may each be replaced by L, and/or one or more double bonds may each be replaced by single bonds, and/or one or more CH groups may each 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 up to 12 C atoms.

2. A compound according to claim 1 , wherein said compound is of formula I*
P a -(Sp a ) s1 -(A 1 ) n1 -A 2 -Q 1 -A 3 -(Sp b ) s2 -P b   I*

in which P a , P b , Sp a , Sp b , A 1 , A 2 , A 3 , Q 1 , s1, s2 and n1 are as defined in claim 1 .

3. A compound according to claim 1 , wherein said compound is of the formula

in which P a , P b , Sp a , Sp b , s1, s2 are as defined in claim 1 ,
and L 3 and L 4 , independently of one another, denote H or F.

4. A liquid crystal medium comprising one or more compounds of formula I
P a -(Sp a ) s1 -(A 1 -Z 1 ) n1 -A 2 -Q 1 -A 3 -(Z 4 -A 4 ) n2 -(Sp b ) s2 -P b   I

in which the individual radicals have the following meanings:
P a , P b each, independently of one another, denote a polymerizable 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,
n1 denotes 0 or 1,
n2 denotes 0,
Q 1 denotes —CF 2 O—,
Z 1 , Z 4 each independently of one another, denote a single bond, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —(CO)O—, —O(CO)—, —(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—, —O—, —CH 2 —, —(CH 2 ) 3 —, or —CF 2 —,
where Z 1 and Q 1 or Z 4 and Q 1 do not simultaneously denote —CF 2 O—,

A 2 denotes

A 3 denotes

and
A 1 , A 4
each, independently of one another, denotes a radical selected from the following groups:
a) the group consisting of 1,4-phenylene and 1,3-phenylene, in which, in addition, one or two CH groups may each be replaced by N and in which, in addition, one or more H atoms may each be replaced by L,
b) the group consisting of trans-1,4-cyclohexylene, 1,4-cyclohexylene and 1,4′-bicyclohexenylene, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced by —O— or —S— and in which, in addition, one or more H atoms may each be replaced by F or Cl,
c) the group consisting of tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-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, and
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,
where, in addition, one or more H atoms in these radicals may each be replaced by L, and/or one or more double bonds may each 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 up to 12 C atoms,
or a polymer obtainable by polymerization of one or more compounds of the formula I.

5. The liquid crystal medium according to claim 4 , wherein said medium further comprises one or more other polymerizable compounds and/or one more unpolymerizable liquid-crystalline compounds.

6. The liquid crystal medium according to claim 4 , wherein said medium comprises the following components:
a polymerizable component A comprising one or more compounds of formula I,
a liquid-crystalline component B comprising one or more compounds of formulla II

in which the individual radicals have the following meanings:
R 22 denotes H, F, Cl 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 in which, in addition, 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—, —O—CO—O—, —S—CO—, —CO—S—, —CY 01 ═CY 02 — 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, one of the radicals Y 01 and Y 02 also denotes 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 on each occurrence, identically or differently, denotes a single bond, —(CH 2 ) 4 —, —CH 2 CH 2 —, —CF 2 —CF 2 —, —CF 2 —CH 2 —, —CH 2 —CF 2 —, —CH═CH—,

Assignees

• Wittek Michael
• Tanaka Norihiko
• Taugerbeck Andreas
• Merck Patent Gmbh

Inventors

• Wittek Michael
• Tanaka Norihiko
• Taugerbeck Andreas

Classifications

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title

• C07C25/13

  containing fluorine · CPC title

• C07C25/18

  Polycyclic aromatic halogenated hydrocarbons · CPC title

• C09K2019/2042

  Ph-Ph-COO-Ph · CPC title

• C09K19/542 Primary

  Macromolecular compounds · CPC title