Liquid-crystalline media having homeotropic alignment

Patent metadata

Field	Value
Publication number	US-11072742-B2
Application number	US-201816225694-A
Country	US
Kind code	B2
Filing date	Dec 19, 2018
Priority date	Dec 20, 2017
Publication date	Jul 27, 2021
Grant date	Jul 27, 2021

Abstract

A liquid-crystalline media (LC media) containing a low-molecular-weight, non-polymer component, and a combination of self-alignment additives for vertical alignment of two or more of the specified kinds (formulae IA to IM). The combination of two or more self-alignment additives affect homeotropic (vertical) alignment of the LC media at a surface or the cell surfaces of a liquid-crystal display (LC display).

First claim

The invention claimed is:

1. A liquid-crystal (LC) medium comprising
a low-molecular-weight, non-polymerizable liquid-crystalline component and
a combination of self-alignment additives for vertical alignment selected from the group consisting of formulae IG and IL

combined with one or more compounds selected from the group consisting of formulae IE, IF, IJ and IK

in which
A 4 , A 5 , A 6 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which optionally contains fused rings, and which is optionally mono-or polysubstituted by a group L or -Sp-P,
A 7 , A 8 , A 9 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which optionally contains fused rings, and which is optionally mono-or polysubstituted by a group L or -Sp-P,
P denotes a polymerizable group,
Sp denotes a spacer group or a single bond,
wherein formulae IE, IF and IG independently comprise one polymerizable group P each, and
wherein formulae IJ, IK and IL independently comprise two or more polymerizable groups P each,
L in each case, independently of one another, denotes H, F, CI, Br, I, —CN, —NO 2 , —NCO, —NCS, —OCN, —SCN, —C(═O)N(R 0 ) 2 , —C(═O)R 0 , optionally substituted silyl, optionally substituted aryl or cycloalkyl having 3 to 20 C atoms, or straight-chain alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 25 C atoms, or branched alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 3 to 25 C atoms, in which one or more H atoms are each optionally replaced by F or CI,
Z 2 , Z 3 in each case, independently of one another, denotes a single bond, —O—, —S—, —CO—, —CO—O—, —OCO—, —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 ) n1 —, —CF 2 CH 2 —, —CH 2 CF 2 —, —(CF 2 ) n1 —, —CH═CH—, —CF═CF—, —C═C—, —CH═CH—COO—, —OCO—CH═CH—, —(CR 0 R 00 ) n1 —, —CH(—Sp-P)—, —CH 2 CH(—Sp-P)—, or —CH(—Sp-P)CH(—Sp-P)—,
n1 denotes 1, 2, 3 or 4,
m denotes 0, 1, 2, 3, 4, 5 or 6,
n denotes 0 or 1,
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 H, halogen, straight-chain alkyl having 1 to 25 C atoms, or branched or cyclic alkyl having 3 to 25 C atoms, in which one or more non-adjacent CH 2 groups are each optionally replaced by —O—, —S—, —CO—, —CH═CH—, —C≡C—, —CO—O—, —O—CO—, or —O—CO—O— in such a way that O and/or S atoms are not linked directly to one another and in which one or more H atoms are each optionally replaced by F or Cl,
or denotes a group -Sp-P,

X 1 each, independently of one another, denotes —OH, —SH, or —NH 2 ,
R 22 denotes alkyl having 1 to 12 C atoms, and
Sp a , Sp c each, independently of one another, denotes a spacer group or a single bond.

2. The liquid-crystal (LC) medium according to claim 1 comprising any of the following combinations of a first and a second self-alignment additive of formulae:
IE and IG,
IF and IG,
IJ and IG,
IJ and IL,
IK and IL,
IE and IL,
IG and IK, or
IF and IL.

3. The liquid-crystal (LC) medium according to claim 1 , wherein said two or more alignment additives each comprise one, two or more polymerizable groups.

4. The liquid-crystal (LC) medium according to claim 1 , comprising one or more self-alignment additives selected from the group consisting of formulae IE and IJ and one or more self-alignment additives selected from the group consisting of formulae IG and IL.

5. The liquid-crystal (LC) medium according to claim 1 , comprising one or more self-alignment additives of formula IJ and one or more compounds of formula IL.

6. The LC medium according to claim 1 , further comprising a polymerizable or polymerized compound other than compounds of formulae IG, IL, IE, IF, IJ and IK, where the polymerized component is obtainable by polymerization of a polymerizable component.

7. The medium according to claim 1 , wherein, in any of formulae IG, IL, IE, IF, IJ and IK,
A 4 , A 5 , A 6 , A 7 , A 8 , A 9 ,
each, independently of one another, denote 1,4-phenylene, naphthalene-1,4-diyl or naphthalene-2,6-diyl, in which one or more CH groups are each optionally replaced by N, cyclohexane-1,4-diyl, in which one or more non-adjacent CH 2 groups are each optionally replaced by O or S, 3,3′-bicyclobutylidene, 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, decahydro-naphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, indane-2,5-diyl, octahydro-4,7-methanoindane-2,5-diyl, or perhydrocyclopenta[a]phenanthrene-3,17-diyl, where any of which is unsubstituted or mono- or polysubstituted by a group L,
and A 4 to A 6 is optionally substituted by a group -Sp-P,
and A 7 to A 9 is optionally substituted by one, two or three groups -Sp-P.

8. The medium according to claim 1 , wherein the compound of formula IJ is a compound of formula IJ1,

in which
R 1 , A 7 , A 8 , A 9 , Z 2 , Z 3 , m, n, L, Sp a , X 1 , Sp and P independently are defined as for the compound of formula IJ,
p1 is 2, and
r1, r2, r3 independently are 0, 1, 2 or 3.

9. The medium according to claim 1 , wherein the compound of formula IK is a compound of formula IK1,

in which
R 1 , A 7 , A 8 , A 9 , Z 2 , Z 3 , m, n, L, Sp a , Sp c , X 1 , Sp and P independently are defined as for the compound of formula IK,
P 1 is 2, and
r1, r2, r3 independently are 0, 1, 2 or 3.

10. The medium according to claim 1 , wherein the one or more compounds of formula IJ are compounds of formulae IJ1-1 to IJ1-9:

in which R 1 , Z 2 , Z 3 , L, Sp and P independently are as defined as for the compound of formula IJ, and
x is 0 or 1,
n is 1, 2, 3, 4, 5, 6, 7 or 8,
p1 is 2, and
r1, r2, r3, r3″ independently denote 0, 1, 2 or 3.

11. The medium according to claim 1 , wherein the one or more compounds of formula IK are compounds of formulae IK1-1 to IK1-9:

in which R 1 , Z 2 , Z 3 , L, Sp, Spy and P independently are as defined as for the compound of formula IK, and
x is 0 or 1,
n is 1, 2, 3, 4, 5, 6, 7 or 8,
p1 is 2, and
r1, r2, r3, r3″ independently denote 0, 1, 2 or 3.

12. The medium according to claim 1 , wherein the compound of formula IJ is a compound of formula IJ1,

in which
R 1 , A 7 , A 8 , A 9 , Z 2 , Z 3 , m, n, L, Sp a , X 1 , Sp and P independently are defined as for the compound of formula IJ,
p1 is 2,
r1, r3 independently are 0, 1, 2 or 3, and
r2 is 2,
or
wherein the compound of formula IK is a compound of formula IK1,

Assignees

• Merck Patent Gmbh

Inventors

• Archetti Graziano
• Saito Izumi
• Fortte Rocco
• Plummer Edward
• Ushakov Dmitry
• Haensel Helmut
• Klasen-Memmer Melanie

Classifications

• C09K19/54 Primary

  Additives having no specific mesophase {characterised by their chemical composition} · CPC title

• C09K19/30

  containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings · CPC title

• C09K19/04 Primary

  characterised by the chemical structure of the liquid crystal components {, e.g. by a specific unit} · CPC title

• G02F1/13

  based on liquid crystals, e.g. single liquid crystal display cells · CPC title

• C09K19/542

  Macromolecular compounds · CPC title