# US 2023/0056437 A1 · Azo dye

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- Number: US 2023/0056437 A1
- Document ID: US20230056437A1
- Status: Published application
- Kind: A1
- Application number: 17/278,953
- Filed: 2019-09-23
- Published: 2023-02-23
- Earliest claimed: 2018-09-25
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Peer KIRSCH; Kerstin ALTENBURG; René LUTZ; Susann GUNST; Michael JUNGE; Ursula PATWAL
- Web page: https://patentgrep.com/patent/US20230056437A1

## CPC

- C09K 19/601: {Azoic}
- C09K 19/3003: {Compounds containing at least two rings in which the different rings are directly linked (covalent bond)}
- C09K 19/3068: {chain containing -COO- or -OCO- groups}
- C09K 19/3402: {having oxygen as hetero atom (sugars C09K19/0422)}
- C09K 19/60: Pleochroic dyes
- C09K 2019/0466: {the linking chain being a -CF2O- chain}
- C09K 2019/122: {Ph-Ph}
- C09K 2019/123: {Ph-Ph-Ph}
- C09K 2019/2035: {Ph-COO-Ph}
- C09K 2019/3004: {Cy-Cy}
- C09K 2019/3006: {Cy-Cy-Cy}
- C09K 2019/3009: {Cy-Ph}
- C09K 2019/301: {Cy-Cy-Ph}
- C09K 2019/3016: {Cy-Ph-Ph}
- C09K 2019/3021: {Cy-Ph-Ph-Cy}
- C09K 2019/3025: {Cy-Ph-Ph-Ph}
- C09K 2019/3027: {Compounds comprising 1,4-cyclohexylene and 2,3-difluoro-1,4-phenylene}
- C09K 2019/3037: {Cy-Cy-C2H4-Ph}
- C09K 2019/3071: {Cy-Cy-COO-Cy}
- C09K 2019/3078: {Cy-Cy-COO-Ph-Cy}
- C09K 2019/3408: {Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems}
- C09K 2019/3422: {the heterocyclic ring being a six-membered ring}
- Y02E 10/549: Organic PV cells
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

The present invention relates to azo dye of formula I defined in claim 1, to a liquid crystalline medium comprising said azo dye, the use of said medium for optical, electrooptical and electronic purposes, in particular in devices for regulating the passage of energy from an outside space into an inside space, for example in windows. The invention further relates to a device containing the liquid crystalline medium according to the invention.

## Claims

### Claim 1

Compound of formula I
in which
W11, W12 identically or differently, denote O, S or Se,
on each occurrence, identically or differently, denotes
R11, R12, identically or differently, denote H, F, straight-chain or branched alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may each be replaced, independently of one another, by —C(Rz)═C(Rz)—, —C≡C—, —N(Rz)—, —O—, —S—, —CO—,
—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, in addition, one or more H atoms may be replaced by F, Cl, Br, I or CN,
Rz on each occurrence, identically or differently, denotes H, halogen, straight-chain, branched or cyclic alkyl having 1 to 25 C atoms, in which, in addition, one or more non-adjacent CH2 groups may be replaced by —O—, —S—, —CO—, —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, in addition, one or more H atoms may be replaced by F or Cl,
A11, A12 each, independently of one another, denote an aryl or heteroaryl group, which may be substituted by one or more radicals L,
A21, A22 are each, independently of one another, defined like A11 or denote a cyclic alkyl group having 3 to 10 C atoms, in which 1 to 4 CH2 groups may be replaced by O in such a way that no two O atoms are adjacent,
L on each occurrence, identically or differently, denotes OH, CH2OH, F, Cl, Br, I, —CN, —NO2, SF5, —NCO, —NCS, —OCN, —SCN, —C(═O)N(Rz)2, —C(═O)Rz, —N(Rz)2, optionally substituted silyl, optionally substituted aryl having 6 to 20 C atoms, or straight-chain or branched alkyl, 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, an aryl or heteroaryl group, which may be substituted by one or more radicals L, and alternatively two adjacent groups L together also denote a straight-chain or branched alkylene group having 2 to 10 C atoms, in which one, several or all H atoms may be replaced by F and in which one or more —CH2CH2— groups can be replaced by —CH═CH—,
Z10, Z11, Z12 on each occurrence, identically or differently, denote a single bond, —N═N—, —CH═N—, —N═CH—, —N═N(O)—, —N(O)═N—, —CRx1═CRx2—, —(CRx1═CRx2)2—, —C≡C—, —C(═O)—, —CH═CH—C(═O)—, —C(═O)—CH═CH—, —CH═CH—COO— or —OCO—CH═CH—,
Z21, Z22 on each occurrence, identically or differently, have one of the meanings of Z10 or denote —O—, —S—, —CRy1Ry2—, —CF2O—, —OCF2—, —C(O)—O—, —O—C(O)—, —O—C(O)—O—, —OCH2—, —CH2O—, —SCH2—, —CH2S—, —CF2S—, —SCF2—, —(CH2)n1—, —CF2CH2—, —CH2CF2—, or —(CF2)n1—,
Rx1, Rx2, independently of one another, denote H, F, Cl, CN or alkyl having 1-12 C atoms,
Ry1, Ry2 each, independently of one another, denote H or alkyl having 1-12 C atoms,
Rx11, Rx12,
Rx13, Rx14 independently of one another, denote H, F, Cl, CN, alkyl, alkenyl, alkoxy or alkenyloxy having 1-12 C atoms,
r and t, independently of one another, denote 0, 1 or 2,
s 0 or 1, and
n1 denotes 1, 2, 3 or 4,
and wherein one or more of Z10, Z11, Z12, Z21, Z22, denote —N═N—.

### Claim 2 (depends on 1)

Compound according to claim 1, wherein W11 and W12 denote S.

### Claim 3 (depends on 1)

Compound according to claim 1, wherein the compound is selected from the group of compounds of the following sub-formulae,
in which R11, R12, A11, A12, A21, A22, Z11, Z12 and Z22 have the meanings defined in claim 1.

### Claim 4 (depends on 1)

Compound according to claim 1, wherein A11 and A12, identically or differently, denote 1,4-phenylene, 1,4-naphthylene, 2,6-naphthylene, thiazole-2,5-diyl, thiophene-2,5-diyl, or thienothiophene-2,5-diyl, wherein one or more H atoms are optionally replaced by a group L as defined in claim 1.

### Claim 5 (depends on 1)

Compound according to claim 1, wherein
denotes
in which
Rx11, Rx12,
Rx13, Rx14 independently of one another, denote H, F, Cl, CN, alkyl, alkenyl, alkoxy or alkenyloxy each having 1-12 C atoms.

### Claim 6 (depends on 1)

Compound according to claim 1, wherein Z11, Z12, Z22, identically or differently, denote a single bond, —CRx1═CRx2— or —C≡C—, in which Rx1 and Rx2 have the meanings given in claim 1.

### Claim 7 (depends on 1)

Compound according to claim 1, wherein R11 and R12, independently of one another, denote a branched alkyl group having 3 to 25 C atoms, in which one or more H atoms can be replaced by F, one or more CH2 groups can be replaced by O and/or NH and one or more CH groups can be replaced by N.

### Claim 8 (depends on 1)

LC medium, characterised in that the medium comprises
a dye component A) comprising one or more compounds of the formula I according to claim 1 and optionally further dichroic dyes, and
a liquid-crystalline component B), also referred to as “LC host mixture”, comprising one or more mesogenic compounds.

### Claim 9 (depends on 8)

LC medium according to claim 8, wherein the medium comprises an LC host mixture with negative dielectric anisotropy comprising one or more compounds selected from the group of compounds of the formulae CY, PY and AC
in which
denotes
denote
denotes
R1, R2,
RAC1,RAC2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH2 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,
Zx, Zy, ZAC each, independently of one another, denote —CH2CH2—, —CH═CH—, —CF2O—, —OCF2—, —CH2O—, —OCH2—, —CO—O—, —O—CO—, —C2F4—, —CF═CF—, —CH═CH—CH2O— or a single bond,
L1-4 each, independently of one another, denote F, Cl, CN, OCF3, CF3, CH3, CH2F, CHF2,
a is 1 or 2,
b is 0 or 1,
c is 0, 1 or 2,
d is 0 or 1.

### Claim 10 (depends on 8)

LC medium according to claim 8, wherein the medium comprises an LC host mixture with positive dielectric anisotropy comprising one or more compounds selected from the group of compounds of formulae II to VIII
in which
each, independently of one another, denote
R20 each, identically or differently, denote a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF2O—, —CH═CH—,
—O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
X20 each, identically or differently, denote F, Cl, CN, SF5, SCN, NCS, a halogenated alkyl radical, a halogenated alkenyl radical, a halogenated alkoxy radical or a halogenated alkenyloxy radical, each having up to 6 C atoms, and
Y20-24 each, identically or differently, denote H or F;
Z20 denotes —C2H4—, —(CH2)4—, —CH═CH—, —CF═CF—, —C2F4—, —CH2CF2—, —CF2CH2—, —CH2O—, —OCH2—, —COO— or —OCF2—, in formulae V and VI also a single bond, in formulae V and VIII also —CF2O—,
r denotes 0 or 1, and
s denotes 0 or 1.

### Claim 11 (depends on 8)

LC medium according to claim 8, wherein the medium comprises one or more compounds selected from the group of compounds of formulae DK and O
in which
R5, R6, RO1
and RO2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH2 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,
denotes
denotes
denotes
denotes
ZO1 denotes —CH2CH2—, —CF2CF2—, —C═C— or a single bond,
ZO2 denotes CH2O, —C(O)O—, —CH2CH2—, —CF2CF2—, or a single bond,
o is 1 or 2,
e is 1 or 2.

### Claim 12 (depends on 11)

LC medium according to claim 11, characterised in that it comprises one or more compounds of formula O, selected from the group of compounds of the sub-formulae O3 to O5
in which
RO1 and RO2, identically or differently, denote straight-chain alkyl having 1 to 6 C atoms or straight-chain alkenyl having 2 to 6 C atoms.

### Claim 13 (depends on 11)

LC medium according to claim 11, characterised in that it comprises one or more compounds of formula DK selected from the group of compounds of the sub-formulae DK1 to DK12:
in which alkyl and alkyl* each, independently of one another, denote a straight-chain alkyl radical having 1-6 C atoms, and alkenyl denotes a straight-chain alkenyl radical having 2-6 C atoms.

### Claim 14 (depends on 1)

A device or composition selected from electro-optical displays, devices for regulating the passage of energy from an outside space into an inside space, electrical semiconductors, organic field-effect transistors (OFETs), printed circuits, radio frequency identification elements (RFIDs), organic light-emitting diodes (OLEDs), lighting elements, photovoltaic devices, optical sensors, effect pigments, decorative elements or dyes for colouring polymers, which comprises a compound according to claim 1.

### Claim 15 (depends on 8)

Device for regulating the passage of energy from an outside space into an inside space, wherein the device contains a switching layer comprising an LC medium according to claim 8.

### Claim 16 (depends on 15)

Window containing a device according to claim 15.