Polymerisable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-10550327-B2
Application number	US-201313861851-A
Country	US
Kind code	B2
Filing date	Apr 12, 2013
Priority date	Nov 21, 2012
Publication date	Feb 4, 2020
Grant date	Feb 4, 2020

Abstract

Polymerisable compounds and processes and intermediates for the preparation thereof. Also liquid-crystal (LC) media comprising the polymerisable compounds, and the use of the polymerisable compounds and LC media for optical, electro-optical and electronic purposes, in particular in LC displays, especially in LC displays of the PSA (“polymer sustained alignment”) type.

First claim

The invention claimed is:

1. A liquid-crystal (LC) medium or a LC display comprising a compound of formula I
P 1 -Sp 1 -(A 1 -Z 1 ) n -A 2 -Sp 4 -CH(Sp 2 -P 2 )(Sp 3 -P 3 )  I

in which the individual radicals have the following meanings:
P 1 , P 2 , P 3 independently of each other denote a polymerisable group,
Sp 1 is a spacer group or a single bond,
Sp 2 and Sp 3 denote —(CH 2 ) p2 —, in which p2 is an integer from 1 to 6,
Sp 4 is —(CH 2 ) p4 —, in which p4 is an integer from 1 to 6,
A 1 , A 2 independently of each other, and on each occurrence identically or differently, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group having 4 to 25 C atoms, which may also contain fused rings, and which is optionally mono- or polysubstituted by L,
Z 1 is selected from the group consisting of —O—, —CO—O—, —OCO—, —OCH 2 —, —CH 2 O—, —CF 2 O—, —OCF 2 —, —CH 2 CH 2 —, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, and a single bond,
L denotes P 1 —, P 1 -Sp 1 -, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R x ) 2 , —C(═O)Y 1 , —C(═O)R x , —N(R x ) 2 , optionally substituted silyl, optionally substituted aryl or heteroaryl having 5 to 20 ring atoms, or straight-chain or branched alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R 00 )═C(R 00 )—, —C≡C—, —N(R 00 )—, —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F, Cl, CN, P 1 — or P 1 -Sp 1 -,
R 00 and R 000 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
Y 1 is halogen,
R x denotes P 1 —, P 1 -Sp 1 -, H, halogen, straight chain, branched or cyclic alkyl having 1 to 25 C atoms, wherein one or more non-adjacent CH 2 -groups are optionally replaced by —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— in such a manner that O- and/or S-atoms are not directly connected with each other, and wherein one or more H atoms are optionally replaced by F, Cl, P 1 — or P 1 -Sp 1 -, optionally substituted aryl, aryloxy, heteroaryl or heteroaryloxy having 5 to 20 ring atoms,
n is 1, 2, 3 or 4.

2. The medium or display according to claim 1 , where, in the compounds of formula I, A 1 , A 2 each, independently of one another, denote 1,4-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl, where one or more CH groups in these groups are optionally replaced by N, cyclohexane-1,4-diyl, in which, in addition, one or more non-adjacent CH 2 groups are optionally replaced by O and/or S, 1,4-cyclohexenylene, bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl, piperidine-1,4-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indane-2,5-diyl, octahydro-4,7-methanoindane-2,5-diyl, anthracene-2,7-diyl, fluorene-2,7-diyl, phenanthrene-2,7-diyl or 9,10-dihydro-phenanthrene-2,7-diyl, where all these groups are unsubstituted or mono- or polysubstituted by L as defined in claim 1 .

3. The medium or display according to claim 1 , where, in the compounds of formula I, Sp 1 is a single bond; or Sp 1 is —(CH 2 ) p2 — or —(CH 2 ) p1 —O—, in which p1 is 1, 2 or 3, Sp 2 and Sp 3 denote —(CH 2 ) p2 —, in which p2 is 1, 2 or 3, and Sp 4 is —(CH 2 ) p4 —, in which p4 is 1, 2 or 3.

4. The medium or display according to claim 1 , where, in the compounds of formula I, P 1 , P 2 and P 3 independently of each other denote a vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane or epoxide group.

5. The medium or display according to claim 1 , wherein the compounds of formula I are selected from the group consisting of compounds of the following sub-formulae:

wherein P 1 , P 2 , P 3 and L are as defined in claim 1 and r is 0, 1, 2, 3 or 4.

6. The medium or display according to claim 1 , wherein the LC display is a PSA (polymer sustained alignment) type display.

7. The medium or display according to claim 1 , wherein the LC medium comprises
a polymerisable component A) comprising one or more polymerisable compounds of formula I as defined in claim 1 , and
an LC component B) comprising one or more low-molecular-weight compounds.

8. The medium or display according to claim 7 , wherein the LC component B comprises one or more compounds of the formulae CY and/or PY:

in which the individual radicals have the following meanings:
a denotes 1 or 2,
b denotes 0 or 1,

denotes

R 1 and R 2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another,
Z x denotes —CH═CH—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, —O—, —CH 2 —, —CH 2 CH 2 — or a single bond,
L 1-4 each, independently of one another, denote F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 .

9. The medium or display according to claim 7 , wherein the LC component B comprises one or more compounds of the following formula:

in which the individual radicals have the following meanings:

denotes

denotes

R 3 and R 4 each, independently of one another, denote alkyl having 1 to 12 C atoms, in which, in addition, one or two non-adjacent CH 2 groups may be replaced by —O—, —CH═CH—, —CO—, —O—CO— or —CO—O— in such a way that O atoms are not linked directly to one another,
Z y denotes —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —COO—, —OCO—, —C 2 F 4 —, —CF═CF— or a single bond.

10. The medium or display according to claim 7 , wherein the LC component B comprises one or more compounds comprising an alkenyl group, which is stable to a polymerisation reaction under the conditions used for the polymerisation of the polymerisable compounds of formula I.

11. An LC medium comprising one or more compounds of formula I as defined in claim 1 .

12. The LC medium according to claim 1 , wherein the compounds of formula I are polymerised.

13. An LC display comprising one or more compounds of formula I as defined in claim 1 .

14. The LC display according to claim 13 , which is a PSA type display.

15. The LC display according to claim 14 , which is a PSA-VA, PSA-OCB, PSA-IPS, PS-FFS, PSA-posi-VA or PSA-TN display.

16. The LC display according to claim 13 , which contains an LC cell having two substrates and two electrodes, where at least one substrate is transparent to light and at least one substrate has one or two electrodes, and a layer, located between the substrates, of an LC medium comprising a polymerised component and a low-molecular-weight compo

Assignees

• Merck Patent Gmbh

Inventors

• Engel Martin
• Taugerbeck Andreas
• Brocke Constanze
• Haensel Helmut
• Derow Stephan
• Vogt Julian

Classifications

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K19/44 Primary

  containing compounds with benzene rings directly linked · CPC title

• C09K2019/3009

  Cy-Ph · CPC title

• C09K2019/0448

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

• C09K2019/3016

  Cy-Ph-Ph · CPC title