# US 2021/0277310 A1 · Liquid-crystalline medium

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- Number: US 2021/0277310 A1
- Document ID: US20210277310A1
- Status: Published application
- Kind: A1
- Application number: 17/314,642
- Filed: 2021-05-07
- Published: 2021-09-09
- Earliest claimed: 2011-03-29
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Melanie KLASEN-MEMMER; Achim GOETZ; Georg BERNATZ
- Web page: https://patentgrep.com/patent/US20210277310A1

## CPC

- C09K 19/3066: {in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers}
- C09K 19/062: {containing one non-condensed benzene ring}
- C09K 19/3001: {Cyclohexane rings}
- C09K 19/3098: {Unsaturated non-aromatic rings, e.g. cyclohexene rings}
- C09K 19/32: containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C09K 19/44: containing compounds with benzene rings directly linked
- C09K 2019/0448: {the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate}
- C09K 2019/122: {Ph-Ph}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/301: {Cy-Cy-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3027: {Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- C09K 2019/3425: {Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems}
- C09K 2019/548: {stabilizing the alignment; Polymer stabilized alignment}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

## Abstract

The invention relates to a liquid-crystalline medium which comprises at least one compound of the formula I, in which R1, R1*, rings A and B, Z1, L1, L2, a and b have the meanings indicated in Claim 1, and to the use thereof for an active-matrix display, in particular based on the VA, PSA, PS-VA, PALC, FFS, PS-FFS, IPS or PS-IPS effect.

## Claims

### Claim 1

An electro-optical display, wherein the electro-optical display: is a polymer-stabilized, vertically-aligned (PS-VA) display or polymer-sustained, vertically-aligned (PSA-VA) display,
comprises a layer of liquid-crystalline medium and at least one transparent electrode,
wherein the liquid-crystalline medium has negative dielectric anisotropy,
wherein the liquid-crystalline medium comprises a polymerizable or polymerized mesogenic compound and
wherein the liquid-crystalline medium comprises a mixture of polar compounds, including:
at least one compound of the formula I,
in which
R1 and R1* each, independently of one another, denote an alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are optionally replaced, independently of one another, by —C≡C—, —CF2O—, —CH═CH—,
—O—, —CO—O—, —O—CO— in such a way that O atoms are not linked directly to one another, and in which, in addition, one or more H atoms are optionally replaced by halogen,
Z1 denotes —CH2O— or —OCH2—
a denotes 0 or 1,
b denotes 1,
each denote
and
L1 and L2 each denote F; and
one or more compounds selected from the compounds of formula IIB,
in which
R2B denotes H, an alkyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals may be replaced by —O—, —S—,
—C≡C—, —CF2O—, —OCF2—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
L3 and L4 each denote F,
Z2 and Z2′ each, independently of one another, denote a single bond, —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —COO—, —OCO—, —C2F4—, —CF═CF—, —CH═CHCH2O—,
q denotes 0 or 1,
(O) denotes an optional —O—, and
v denotes 1 to 6.

### Claim 2 (depends on 1)

The electro-optical display of claim 1, wherein the compound of formula IIB is a compound of the formulae IIB-11,
in which alkyl is propyl and alkyl* is ethyl.

### Claim 3 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium comprises no photoinitiator.

### Claim 4 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium comprises one or more compounds of the formula I which are of the formula I-1 and/or the formula I-73:
wherein alkyl denotes a straight-chain alkyl radical having 1-6 C atoms and alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms.

### Claim 5 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium comprises a compound of the formula I-1 wherein alkyl is propyl and alkoxy is ethoxy and/or a compound of the formula I-73 wherein alkyl is propyl and alkoxy is ethoxy.

### Claim 6 (depends on 5)

The electro-optical display of claim 5, wherein the compound of formula IIB is a compound of the formulae IIB-11,
in which alkyl is propyl and alkyl* is ethyl.

### Claim 7 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium additionally comprises one or more compounds of the formula III,
in which
R31 and R32 each, independently of one another, denote a straight-chain alkyl, alkoxyalkyl or alkoxy radical having 1 to 12 C atoms, and
denotes
Z3 denotes a single bond, —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —COO—, —OCO—, —C2F4—, —C4H8—, or —CF═CF—.

### Claim 8 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium additionally comprises one or more compounds of the formulae L-1 to L-11,
in which
R, R1 and R2 each, independently of one another, denote H, an alkyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals are optionally replaced by —O—, —S—,
—C≡C—, —CF2O—, —OCF2—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another, alkyl denotes an alkyl radical having 1-6 C atoms, and
s denotes 1 or 2.

### Claim 9 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium additionally comprises one or more terphenyls of the formulae T-1 to T-21,
in which
R denotes a straight-chain alkyl or alkoxy radical having 1-7 C atoms,
n denotes 1-4, and
m denotes 1-6.

### Claim 10 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium additionally comprises one or more compounds of the formulae O-1 to O-16,
in which
R1 and R2 each, independently of one another, denote H, an alkyl radical having up to 15 C atoms which is unsubstituted, monosubstituted by CN or CF3 or at least monosubstituted by halogen, where, in addition, one or more CH2 groups in these radicals are optionally replaced by —O—, —S—,
—C≡C—, —CF2O—, —OCF2—, —OC—O— or —O—CO— in such a way that O atoms are not linked directly to one another.

### Claim 11 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium additionally comprises one or more indane compounds of the formula In,
in which
R11, R12, R13 denote a straight-chain alkyl, alkoxy, alkoxyalkyl or alkenyl radical having 1-5 C atoms,
R12 and R13 additionally also denote halogen or hydrogen,
denotes
and
i denotes 0, 1 or 2.

### Claim 12 (depends on 1)

The electro-optical display of claim 1, wherein, in the liquid-crystalline medium, the proportion of compounds of the formula I in the mixture as a whole is ≥1% by weight.

### Claim 13 (depends on 1)

The electro-optical display of claim 1, wherein, in the liquid-crystalline medium, the concentration of the polymerized or polymerizable mesogenic compound(s), based on the medium, is 0.01-5% by weight.

### Claim 14 (depends on 1)

The electro-optical display of claim 1, wherein, in the liquid-crystalline medium, the polymerized or polymerizable mesogenic compound(s) is (are) selected from compounds of the formula I*
Ra-A1-(Z1-A2)m-Rb I*
in which the individual radicals have the following meanings:
Ra and Rb each, independently of one another, denote P, P-Sp-, H, halogen, SF5, NO2, a carbon group or hydrocarbon group, where at least one of the radicals Ra and Rb denotes or contains a group P or P-Sp-,
P on each occurrence, identically or differently, denotes a polymerisable group,
Sp on each occurrence, identically or differently, denotes a spacer group or a single bond,
A1 and A2 each, independently of one another, denote an aromatic, heteroaromatic, alicyclic or heterocyclic group, which may also contain fused rings, and which may also be mono- or polysubstituted by L,
L denotes P-Sp-, H, OH, CH2OH, halogen, SF5, NO2, a carbon group or hydrocarbon group,
Z1 on each occurrence, identically or differently, denotes —O—, —S—, —CO—, —CO—O—, —OCO—, —O—CO—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2O—, —OCF2—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, —(CF2)n1—, —CH═CH—, —CF═CF—, —OC—, —CH═CH—COO—, —OCO—CH═CH—, CR0R00 or a single bond,
R0 and R00 each, independently of one another, denote H or alkyl having 1 to 12 C atoms,
m denotes 0, 1, 2, 3 or 4, and
n1 denotes 1, 2, 3 or 4.

### Claim 15 (depends on 1)

The electro-optical display of claim 1, wherein the display has active-matrix addressing, contains an cell comprising two substrates and two electrodes, where at least one substrate is transparent to light and at least one substrate has one or two electrodes, and a layer, located between the substrates, of the liquid-crystalline medium.

### Claim 16 (depends on 4)

The electro-optical display of claim 4, wherein the liquid-crystalline medium comprises at least one compound of the formulae I-1.

### Claim 17 (depends on 4)

The electro-optical display of claim 4, wherein the liquid-crystalline medium comprises at least one compound of the formulae I-73.

### Claim 18 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium further comprises at least one stabilizer compound selected from the following compounds:

### Claim 19 (depends on 1)

The electro-optical display of claim 1, wherein the liquid-crystalline medium further comprises one or more compounds of the formulae B-1 to B-4,
in which
alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, and
alkoxy denotes a straight-chain alkoxy radical having 1-6 C atoms,
alkenyl and alkenyl* each, independently of one another, denote a straight-chain alkenyl radical having 2-6 C atoms.