Polymerizable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-2016159763-A1
Application number	US-201615014890-A
Country	US
Kind code	A1
Filing date	Feb 3, 2016
Priority date	Jan 20, 2011
Publication date	Jun 9, 2016
Grant date	—

Abstract

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

First claim

1 . (canceled)

2 . (canceled)

3 . A compound of formula I according to claim 15 of sub-formulae:

4 . A compound of formula I according to claim 15 of the following sub-formulae:

in which Sp′ has one of the meanings given for Sp, and is identical to or different from Sp, R′ has one of the meanings indicated for R b which is different from H, P— and P-Sp-, and the phenylene and naphthalene groups are optionally substituted with one, two, three of four F atoms.

5 . (canceled)

6 . (canceled)

7 . (canceled)

8 . (canceled)

9 . (canceled)

10 . (canceled)

11 . (canceled)

12 . (canceled)

13 . (canceled)

14 . (canceled)

15 . A compound of formula I

wherein
G denotes —CM=CR c —CO—, —CO—CR c =CM-, —CR c =CM-CO— or —CO—CM=CR c -
M denotes —X 2 -A 4 -(Z 2 -A 3 ) n2 -R b ,
A 1-4 each, independently of one another, and on each occurrence identically or differently, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably having 4 to 25 C atoms, which may also contain fused rings, and which is optionally mono- or polysubstituted by L, and A 2 and A 4 may also denote a single bond,
X 1 and X 2 each, independently of one another, and on each occurrence identically or differently, denote —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or a single bond,
Z 1 and Z 2 each, independently of one another, and on each occurrence identically or differently, denote —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n3 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n3 —, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —CH≡CH—CO—O—, —O—CO—CH═CH—, —CH 2 —CH 2 —CO—O—, —O—CO—CH 2 —CH 2 —, —CR 0 R 00 — or a single bond,
R a-c each, independently of one another, and on each occurrence identically or differently, denote P, P-Sp-, H, OH, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, SF 5 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 000 )—, —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, Br, I, CN or P-Sp-,
wherein at least two of the radicals R a denote or contain a group P or P-Sp-,

P denotes on each occurrence, identically or differently, a polymerisable group,
Sp denotes on each occurrence, identically or differently, a spacer group or a single bond,
R 00 and R 000 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
L denotes on each occurrence, identically or differently, P-Sp-, H, OH, CH 2 OH, halogen, SF 5 , NO 2 , a carbon group or hydrocarbon group,
n1 and n2 each, independently of one another, denote 0, 1, 2 or 3,
n3 denotes 1, 2, 3 or 4,
x denotes 2, 3 or 4,
wherein at least one of (a)-(c) is satisfied:
(a) at least one of X 1 or X 2 is a single bond,
(b) at least one of n1 and n2 is different from 0,
(c) at least one of A 2 and A 4 is not a single bond.

16 . A compound of formula I*

G denotes —CM=CR c —CO—, —CO—CR c =CM-, —CR c =CM-CO— or —CO—CM=CR c —
M denotes —X 2 -A 4 -(Z 2 -A 3 ) n2 -R b ,
A 1-4 each, independently of one another, and on each occurrence identically or differently, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, preferably having 4 to 25 C atoms, which may also contain fused rings, and which is optionally mono- or polysubstituted by L, and A 2 and A 4 may also denote a single bond,
X 1 and X 2 each, independently of one another, and on each occurrence identically or differently, denote —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O— or a single bond,
Z 1 and Z 2 each, independently of one another, and on each occurrence identically or differently, denote —O—, —S—, —CO—, —CO—O—, —O—CO—, —O—CO—O—, —OCH 2 —, —CH 2 O—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —(CH 2 ) n3 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n3 —, —CH═CH—, —CF═CF—, —CH═CF—, —CF═CH—, —C≡C—, —CH═CH—CO—O—, —O—CO—CH═CH—, —CH 2 —CH 2 —CO—O—, —O—CO—CH 2 —CH 2 —, —CR 0 R 00 — or a single bond,
R c each, independently of one another, and on each occurrence identically or differently, denote P, P-Sp-, H, OH, F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, SF 5 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 000 )—, —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, Br, I, CN or P-Sp-,
wherein at least two of the radicals R a denote or contain a group P or P-Sp-,

P denotes on each occurrence, identically or differently, a polymerisable group,
Sp denotes on each occurrence, identically or differently, a spacer group or a single bond,
R 00 and R 000 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
L denotes on each occurrence, identically or differently, P-Sp-, H, OH CH 2 OH, halogen, SF 5 , NO 2 , a carbon group or hydrocarbon group,
n1 and n2 each, independently of one another, denote 0, 1, 2 or 3,
n3 denotes 1, 2, 3 or 4,
x denotes 2, 3 or 4,
wherein at least one of (a)-(c) is satisfied:
(a) at least one of X 1 or X 2 is a single bond,
(b) at least one of n1 and n2 is different from 0,
(c) at least one of A 2 and A 4 is not a single bond,
R a and R b denote -Sp-O—Sg, and
Sg denotes an H atom or a protecting group.

17 . A compound according to claim 16 , of sub-formulae:

wherein each Sp′ independently has one of the meanings of Sp.

18 . A process for the preparation of a compound according to claim 15 by esterification or etherification of a compound of formula I*

G denotes —CM=CR

Assignees

• Merck Patent Gmbh

Inventors

• Taugerbeck Andreas
• Goetz Achim
• Hahn Alexander
• Engel Martin

Classifications

• C09K2019/3004

  Cy-Cy · CPC title

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C09K2019/3016

  Cy-Ph-Ph · CPC title

• C09K19/44 Primary

  containing compounds with benzene rings directly linked · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title