Compounds for the homeotropic alignment of liquid-crystalline media

Patent metadata

Field	Value
Publication number	US-11274254-B2
Application number	US-201916267530-A
Country	US
Kind code	B2
Filing date	Feb 5, 2019
Priority date	Feb 5, 2018
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

Liquid-crystalline media (LC media) comprising self-aligning mesogens (self-alignment additives) which effect homeotropic (vertical) alignment of the LC media at a surface or the cell walls of a liquid-crystal display (LC display). The self-alignment additives contain five-ring systems. LC displays having homeotropic alignment of the liquid-crystalline medium (LC medium) without conventional alignment layers are provided.

First claim

The invention claimed is:

1. A compound of the formula I-A

in which

independently denote a ring of the formula

p1 denotes 2,
r1 denotes 0, 1 or 2,
r2 denotes 1,
r3 denotes 1,
r4 denotes 0 or 1, and
r5 denotes 0 or 1
L in each case, independently of one another, denotes unbranched alkyl, alkenyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, branched alkyl, alkenyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, or denotes F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R 0 R 00 or cycloalkyl having 3 to 6 C atoms,
P denotes a polymerisable methacrylate group,
Sp denotes a spacer group or a single bond,
R 0 in each case, independently of one another, denotes alkyl having 1 to 12 C atoms,
R 00 in each case, independently of one another, denotes H or alkyl having 1 to 12 C atoms,
R 1 denotes an alkyl radical having 1 to 25 C atoms, where, in addition, one or more CH 2 groups in this radical may each be replaced, independently of one another, by —CH═CH—, —C≡C—, —CF 2 O—, —OCF 2 —

—O—, —S—, —CO—, —CO—O— or —O—CO— in such a way that O/S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl, or denotes H, or a group -Sp-P,
R a denotes an anchor group of the formula

p denotes 1 or 2,
q denotes 2 or 3,
B denotes a substituted or unsubstituted ring system or condensed ring system,
denotes 1,
X 1 , independently of one another, denotes OH, SH, NH 2 , NHR 11 , NR 11 2 , C(O)OH or —CHO,
R 11 denotes alkyl having 1 to 12 C atoms, when linear or 3 to 12 C atoms when branched, and in which H may be substituted by fluorine or alkoxy having 1 to 8 C atoms,
Sp a , Sp c , Sp d in each case, independently of one another, denote a spacer group or a single bond, and
Sp b denotes a tri- or tetravalent group.

2. A compound according to claim 1 , wherein

denotes a ring of the formula

denotes a ring of the formula

3. A compound according to claim 1 , wherein
Sp a denotes an unbranched alkylene chain having 1 to 8 C atoms or branched alkylene chain having 3 to 8 C atoms, in which, in each case, one or more CH 2 groups may be replaced by —O—, —NH—, —NR 3 —, —S— or —(CO)—, so that O/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 or —OH,
or a single bond.

4. A compound according to claim 1 , wherein in the group R a ,
Sp b denotes —CH or —CR 3 (for p=1) or C (for p=2),
in which R 3 is an unbranched alkyl radical having 1 to 10 C atoms or branched alkyl radical having 3 to 10 C atoms,
and

Sp c denotes an unbranched alkylene chain having 1 to 8 C atoms or branched alkylene chain having 3 to 8 C atoms, in which one or more CH 2 groups may be replaced by —O—, and in which, in addition, one or more H atoms may be replaced by F, Cl or —OH,
or a single bond.

5. A compound selected from the following formulae:

in which
R 1 denotes an alkyl radical having 1 to 25 C atoms, where, in addition, one or more CH 2 groups in this radical may each be replaced, independently of one another, by —CH═CH—, —C≡C—, —CF 2 O—, —OCF 2 —,

—O—, —S—, —CO—, —CO—O— or —O—CO— in such a way that O/S atoms are not linked directly to one another, and in which, in addition, one or more H atoms may be replaced by F or Cl, or denotes H,
or a group -Sp-P, wherein P denotes a polymerisable group and Sp denotes a spacer group or a single bond,
L denotes in each case, independently of one another, denotes unbranched alkyl, alkenyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, or branched alkyl, alkenyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 25 C atoms, in which, in addition, one or more H atoms may be replaced by F or Cl, or denotes F, Cl, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R 0 R 00 or cycloalkyl having 3 to 6 C atoms, wherein R 0 in each case, independently of one another, denotes alkyl having 1 to 12 C atoms, and R 00 in each case, independently of one another, denotes H or alkyl having 1 to 12 C atoms,
and
R a denotes an anchor group of the formula

p denotes 1 or 2,
q denotes 2 or 3,
B denotes a substituted or unsubstituted ring system or condensed ring system,
denotes 0 or 1,
X 1 , independently of one another, denotes OH, SH, NH 2 , NHR 11 , NR 11 2 , C(O)OH or —CHO,
R 11 denotes alkyl having 1 to 12 C atoms when linear or 3 to 12 C atoms when branched, and in which H may be substituted by fluorine or alkoxy having 1 to 8 C atoms,
Sp a , Sp c , Sp d in each case, independently of one another, denote a spacer group or a single bond, and
Sp b denotes a tri- or tetravalent group.

6. A compound according to claim 5 , wherein
L denotes F, Cl, CH 3 , ethyl, propyl, cyclopropyl or isopropyl.

7. A compound according to claim 5 , wherein the group R a denotes a group selected from the sub-formulae

Assignees

• Merck Patent Gmbh

Inventors

• Klasen-Memmer Melanie
• Plummer Edward
• Fortte Rocco
• Haensel Helmut
• Uebel Timo
• Lehmann Tamara

Classifications

• C09K2019/0448

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

• C09K19/56 Primary

  Aligning agents · CPC title

• G02F1/1337

  Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers · CPC title

• C09K19/02 Primary

  characterised by optical, electrical or physical properties of the components, in general · CPC title

• C09K19/3852

  Poly(meth)acrylate derivatives · CPC title