Polymerizable compounds and the use thereof in liquid-crystal displays

Patent metadata

Field	Value
Publication number	US-10344215-B2
Application number	US-201615175634-A
Country	US
Kind code	B2
Filing date	Jun 7, 2016
Priority date	Jun 9, 2015
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

Abstract

The present invention relates to polymerizable compounds, to processes and intermediates for the preparation thereof, to liquid-crystal media comprising them, and to the use of the polymerizable compounds and liquid crystalline media for optical, electro-optical and electronic purposes, in particular in liquid crystalline displays, especially in liquid crystalline displays of the polymer sustained alignment type.

First claim

The invention claimed is:

1. A compound of formula I
P-Sp-Ar-R  I

wherein
Ar is

which is substituted by at least one group L a and optionally substituted by one or more groups L,
L a is an alkoxy group with 1 to 12 C atoms that is straight-chain or branched and is optionally fluorinated,
L is on each occurrence identically or differently F, Cl, —CN, P-Sp-, or 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 each optionally replaced by F or Cl, or L has the meaning of L a ,
P is a polymerizable vinyloxy, acrylate, methacrylate, fluoroacrylate, chloroacrylate, oxetane or epoxide group,
Sp is a spacer group that is a single bond —(CH 2 ) p2 —, —(CH 2 ) p2 —O—, —(CH 2 ) p2 —CO—O—, or —(CH 2 ) p2 —O—CO—, wherein p2 is 2, 3, 4, 5 or 6, and the O—atom or the CO—group, respectively, is connected to the aromatic ring, or is a spacer group substituted by polymerizable groups Sp(P) 2 , having the following formulae:
—X-alkyl-CHPP  S1

—X-alkyl-CH((CH 2 ) aa P)((CH 2 ) bb P)  S2

—CO—NH((CH 2 ) aa P)((CH 2 ) bb P)  S3

—X-alkyl-CHP—CH 2 —CH 2 P  S4

—X-alkyl-C(CH 2 P)(CH 2 P)—C aa H 2aa+1   S5

—X-alkyl-CHP—CH 2 P  S6

—X-alkyl-CPP—C aa H 2aa+1   S7 or

—X-alkyl-CHPCHP—C aa H 2aa+1   S8

in which
alkyl denotes a single bond or straight-chain or branched alkylene having 1 to 12 C atoms which is unsubstituted or mono- or poly-substituted by F, Cl or CN and in which one or more non-adjacent CH 2 groups may each, independently of one another, be replaced by —C(R 0 )═C(R 0 )—, —C≡C—, —N(R 0 )—, —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, where R 0 is alkyl with 1-20 C atoms,
aa, bb each, independently of one another, denote 0, 1, 2, 3, 4, 5 or 6, and
X is O, O—CO—, CO—O or a single bond,
R is -Sp-P, H or has one of the meanings given for L,
wherein, if Ar is Ar4, all groups P that are present in the compound have the same meaning.

2. The compound of claim 1 , wherein all groups P that are present in the compound have the same meaning.

3. The compound of claim 1 , of the following subformulae:

r1, are independently of each other 0, 1, 2 or 3,
r2 is 0, 1, 2, 3 or 4,
r4, is 0, 1 or 2,
with r1+r2+r3≥1, r1+r3+r4≥1, and
wherein the compounds contain at least one substituent L that denotes L a as defined in formula I.

4. The compound according to any one of claim 3 , of the following sub-formulae

5. The compound according to claim 1 , of the following subformulae

wherein L′ has one of the meanings given for L.

6. The compound according to claim 1 , wherein P denotes acrylate or methacrylate.

7. A liquid crystalline medium comprising one or more polymerizable compounds formula I as defined in claim 1 .

8. The liquid crystalline medium of claim 7 , comprising
a polymerizable component A) comprising one or more polymerizable compounds of formula I, and
a liquid-crystalline component B) comprising one or more mesogenic or liquid-crystalline compounds.

9. The liquid crystalline medium of claim 7 , comprising 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,

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, CHF 2 .

10. The liquid crystalline medium according to claim 7 comprising one or more compounds of the following formulae:

in which the individual radicals, on each occurrence identically or differently, each, independently of one another, have the following meaning:

R A1 is alkenyl having 2 to 9 C atoms or, if at least one of the rings X, Y and Z denotes cyclohexenyl, also one of the meanings of R A2 ,
R A2 is 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—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another,
Z x is —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O—, or a single bond,
L 1-4 each, independently of one another, are H, F, Cl, OCF 3 , CF 3 , CH 3 , CH 2 F or CHF 2 H,
x is 1 or 2,
z is 0 or 1.

11. The liquid crystalline medium according to claim 7 , comprising one or more compounds of the following formula:

in which the individual radicals have the following meanings:

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.

12. The liquid crystalline medium according to claim 7 , wherein the polymerizable compounds of

Assignees

• Merck Patent Gmbh

Inventors

• Tong qiong
• Schwebel Nico
• Brocke Constanze
• DEING Kaja Christina
• Vogt Julian
• Meyer Elisabeth

Classifications

• C09K2019/123

  Ph-Ph-Ph · CPC title

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C09K2019/301

  Cy-Cy-Ph · CPC title

• C07C235/60

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C09K2019/3027

  Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene · CPC title