Liquid crystal displays and liquid crystalline media with homeotropic alignment

Patent metadata

Field	Value
Publication number	US-11015121-B2
Application number	US-201916397782-A
Country	US
Kind code	B2
Filing date	Apr 29, 2019
Priority date	Sep 25, 2010
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

The present invention relates to liquid-crystalline media (LC media) having negative or positive dielectric anisotropy comprising self-aligning mesogens (SAMs) which effect homeotropic (vertical) alignment of the LC media at a surface or the cell walls of a liquid-crystal display (LC display). The invention therefore also encompasses LC displays having homeotropic alignment of the liquid-crystalline medium (LC medium) without conventional imide alignment layers. The LC media may be supplemented by a polymerisable or polymerised component, which serves for stabilisation of the alignment, for adjustment of the tilt angle and/or as passivation layer.

First claim

The invention claimed is:

1. A LC medium comprising a low-molecular-weight liquid-crystalline component and at least one organic compound, where the at least one organic compound contains at least one polar anchor group and at least one ring group, the polar anchor group of the organic compound contains at least one OH structure or an N atom in a primary or secondary or tertiary amino group,
said LC medium being nematic, and wherein the at least one organic compound encompasses a compound of the formula MES-R 2 ,

in which
MES denotes a mesogenic group containing at least one ring system, and
R 2 denotes a polar anchor group encompassing a group of sub-formula (A1)
-Sp-[X 2 -Z 3 -]kX 1   (A1)

in which
Sp denotes a spacer group,
X 1 denotes a group —NH 2 , —NHR 11 , —NR 11 2 , —OR 11 , —OH, —(CO)OH or a group of the formula

R 0 denotes H or alkyl having 1 to 12 C atoms,
X 2 in each case independently denotes —NH—, —NR 11 —, —O— or a single bond,
Z 3 in each case independently denotes an alkylene group having 1-15 C atoms, carbocyclic rings having 5 or 6 C atoms, or combinations of one or more rings and alkylene groups, in each of which hydrogen may be replaced by —OH, —OR 11 , —(CO)OH, —NH 2 , —NHR 11 , —NR 11 2 or halogen,
R 11 in each case independently denotes a halogenated or unsubstituted alkyl radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in this radical may each be replaced, independently of one another, by —CC—, —CH═CH—, —(CO)O—, —O(CO)—, —(CO)— or —O— in such a way that O atoms are not linked directly to one another, and where two radicals R 11 may be linked to one another to form a ring, and
k denotes 0, 1, 2 or 3.

2. The LC medium according to claim 1 , additionally comprising a polymerizable or polymerized component, where the polymerized component is obtainable by polymerization of a polymerizable component.

3. The LC medium according to claim 1 , wherein the organic compound has a relative molar mass of greater than 100 g/mol.

4. The LC medium according to claim 1 , comprising the at least one organic compound in a concentration of less than 10% by weight.

5. The LC medium according to claim 1 , comprising one or more polymerizable compounds of the formula M or a polymerized component which comprises one or more compounds of the formula M in polymerized form:
P a -(Sp a ) s1 -A 2 -(Z 1 -A 1 ) n -(Sp b ) s2 -P b   M

in which the individual radicals have the following meanings:
P a , P b each, independently of one another, denote a polymerizable group,
Sp a , Sp b on each occurrence, identically or differently, denote a spacer group,
s1, s2 each, independently of one another, denote 0 or 1,
A 1 , A 2 each, independently of one another, denote a radical of (a), (b), (c) or (d):
a) trans-1,4-cyclohexylene, 1,4-cyclohexenylene or 4,4″-bicyclohexylene, in which, in addition, one or more non-adjacent CH 2 groups may be replaced by —O— and/or —S— and in which, in addition, one or more H atoms may be replaced by F,
b) 1,4-phenylene or 1,3-phenylene, in which, in addition, one or two CH groups may be replaced by N and in which, in addition, one or more H atoms may be replaced by L,
c) tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrofuran-2,5-diyl, cyclobutane-1,3-diyl, piperidine-1,4-diyl, thiophene-2,5-diyl or selenophene-2,5-diyl, each of which may also be mono- or polysubstituted by L,
d) saturated, partially unsaturated or fully unsaturated, and optionally substituted, polycyclic radicals having 5 to 20 cyclic C atoms, one or more of which may, in addition, be replaced by heteroatoms,
n denotes 0, 1, 2 or 3,
Z 1 in each case, independently of one another, denotes —CO—O—, —O—CO—, —CH 2 O—, —OCH 2 —, —CF 2 O—, —OCF 2 —, or —(CH 2 ) n —, where n is 2, 3 or 4, —O—, —CO—, —C(R y R z )—, —CH 2 CF 2 —, —CF 2 CF 2 — or a single bond,
L on each occurrence, identically or differently, denotes F, Cl, CN, SCN, SF 5 or straight-chain or branched, in each case optionally fluorinated, alkyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy having 1 to 12 C atoms.

6. The LC medium according to claim 1 , wherein the at least one organic compound contains one or more polymerizable groups.

7. A LC display comprising an LC cell having two substrates and at least two electrodes, where at least one substrate is transparent to light and at least one substrate has one or two electrodes, and a layer of an LC medium according to claim 1 located between the substrates,
where the at least one organic compound is suitable for effecting homeotropic alignment of the LC medium with respect to the substrate surfaces.

8. The LC display according to claim 7 , wherein the substrates have no alignment layers for homeotropic alignment.

9. The LC display according to claim 7 , wherein the substrates have unrubbed alignment layers on one or both sides.

10. The LC display according to claim 7 , that is a VA display containing an LC medium having negative dielectric anisotropy and electrodes arranged on opposite substrates.

11. The LC display according to claim 7 , that is a VA-IPS display containing an LC medium having positive dielectric anisotropy and interdigital electrodes arranged on at least one substrate.

12. A process for the preparation of an LC medium according to claim 1 , comprising mixing one or more organic compounds containing at least one polar anchor group and at least one ring group with a low-molecular-weight liquid-crystalline component, and one or more polymerizable compounds and/or additives are optionally added.

13. A process for the production of an LC display comprising an LC cell having two substrates and at least two electrodes, where at least one substrate is transparent to light and at least one substrate has one or two electrodes, comprising:
filling of the cell with an LC medium comprising a low-molecular-weight liquid-crystalline component, a polymerizable component and an organic compound containing at least one polar anchor group according to claim 1 which is suitable for effecting homeotropic (vertical) alignment of the LC medium with respect to the substrate surfaces, and optionally
polymerization of the polymerizable component, optionally with application of a voltage to the cell or under the action of an electric field.

14. The LC medium according to claim 5 , wherein the polycyclic radicals having 5 to 20 cyclic C atoms are bicyclo[1.1.1]pentane-1,3-diyl, bicyclo[2.2.2]octane-1,4-diyl, spiro[3.3]heptane-2,6-diyl,

where, in addition, one or more H atoms in these radicals may be replaced by L, and/or one or more double bonds may be replaced by single bonds, and/or one or more CH groups may be replaced by N,
M denotes —O—, —S—, —CH 2 —, —CHY 1 — or —CY 1 Y 2 —,
R 00 is H, F, straight-chain or branched alkyl having 1 to 12 C atoms in which one or more H atoms are optionally replaced by F, and
Y 1 and Y 2 each, independently of one another, are H, F or straight-chain or branched alkyl having 1 to 12 C atoms, in which, in addition, one or more H atoms may be replaced by F, or denote Cl or CN.

15. The liquid crystalline medium according to claim 1 , further comprising one or more compounds of the formula A, B or C,

Assignees

• Merck Patent Gmbh

Inventors

• Graziano Archetti
• Taugerbeck Andreas

Classifications

• C09K19/42 Primary

  Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 · CPC title

• C09K2019/0425

  characterized by a specific unit that results in a functional effect · CPC title

• C09K19/12 Primary

  at least two benzene rings directly linked, e.g. biphenyls · CPC title

• C09K19/32

  containing condensed ring systems, i.e. fused, bridged or spiro ring systems · CPC title

• G02F1/133711

  by organic films, e.g. polymeric films · CPC title