Dichroic dye composition

Patent metadata

Field	Value
Publication number	US-11939512-B2
Application number	US-201917295913-A
Country	US
Kind code	B2
Filing date	Nov 21, 2019
Priority date	Nov 23, 2018
Publication date	Mar 26, 2024
Grant date	Mar 26, 2024

Abstract

The present invention relates to compositions comprising a combination of benzothiadiazole and thiadiazoloquinoxaline derivatives, to liquid-crystalline media containing the compositions, and to the use of the compositions and the media in optical, electronic and electro-optical devices, in particular in devices for regulating the passage of energy from an outside space into an inside space, for example in switchable windows.

First claim

The invention claimed is:

1. A liquid-crystalline medium comprising:
two or more compounds of formula I

and two or more compounds of formula II

wherein
R 1 on each occurrence, identically or differently, denotes H, F, CN, N(R z ) 2 , Si(R z ) 3 , or a straight-chain having 1 to 20 C atoms or branched alkyl or alkoxy having 3 to 20 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may each be replaced, independently of one another, by —C(R z )═C(R z )—, —C≡C—,

—N(R z )—, —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 each be replaced by F or CN,
X on each occurrence, identically or differently, denotes CR a or N,
R a on each occurrence, identically or differently, denotes H, straight-chain alkyl having 1 to 12 C atoms, branched alkyl having 3 to 12 C atoms, F, Cl, N(R z ) 2 or CN,
R 2 and R z on each occurrence, identically or differently, denote H, halogen, or straight-chain alkyl having 1 to 12 C atoms, branched alkyl having 3 to 12 C atoms, or cyclic alkyl having 3 to 12 C atoms, in which, in addition, one or more non-adjacent CH 2 groups may each 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 each be replaced by F or Cl,
Ar 1 and Ar 2 on each occurrence, identically or differently, denote an aryl or heteroaryl group, which may be substituted by one or more radicals L,
L on each occurrence, identically or differently, denotes F, Cl, CN, OH, SCN, SF 5 , N(R z ) 2 , straight-chain, optionally fluorinated, alkyl or alkoxy having 1 to 12 C atoms, branched, optionally fluorinated, alkyl or alkoxy having 3 to 12 C atoms, straight-chain alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, optionally fluorinated, having 2 to 12 C atoms, or branched alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy or alkoxycarbonyloxy, optionally fluorinated, having 4 to 12 C atoms
Z 1 on each occurrence, identically or differently, denotes a single bond, —O—, —S—, —C(O)—, —CR y1 R y2 —, —CF 2 O—, —OCF 2 —, —C(O)—O—, —O—C(O)—, —OCH 2 —, —CH 2 O—, —CR x1 ═CR x2 —, —C≡C—, —CR x1 ═CR x2 —CO—, —CO—CR x1 ═CR x2 —, —CR x1 ═CR x2 —COO—, —OCO—CR x1 ═CR x2 — or —N═N—,
Z 2 on each occurrence, identically or differently, denotes a single bond, —CF 2 O—, —OCF 2 — or —C≡C—,
a, b, c and d independently of one another, denote 0 or 1,
R x1 , R x2 independently of one another, denote H, F, Cl, CN or alkyl having 1 to 12 C atoms,
R y1 denotes H or alkyl having 1 to 12 C atoms, and
R y2 denotes alkyl having 1 to 12 C atoms, and
one or more mesogenic compounds,
wherein the composition comprises at least one purple dye, at least one blue dye, at least one yellow dye, at least one red dye and at least one near-infrared dye.

2. The liquid-crystalline medium according to claim 1 , wherein Ar 1 and Ar 2 denote, independently of one another, 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 may be replaced by the group L as defined in claim 1 .

3. The liquid-crystalline medium according to claim 1 , wherein at least one of Ar 1 is thiophene-2,5-diyl or thienothiophene-2,5-diyl.

4. The liquid-crystalline medium according to claim 1 , wherein
R 1 identically or differently, denotes a straight-chain alkyl or alkoxy having 1 to 15 C atoms, branched alkyl or alkoxy having 3 to 15 C atoms, or N(R b ) 2 ,
R b is, independently of one another, a straight-chain alkyl having 1 to 9 C atoms, R 2 identically or differently, denotes a straight-chain alkyl having 1 to 9 C atoms,
a, b, c, and d each denote 1,
Z 1 is a single bond, and
Z 2 is a single bond.

5. The liquid-crystalline medium according to claim 1 , wherein at least one of said two or more compounds of formula I is selected from the compounds of formulae I-1, I-2, I-3, and I-4

and at least one of said two or more compounds of formula II

is selected from the compounds of formulae II-1, II-2, II-3, II-4, and II-5

6. The liquid-crystalline medium according to claim 1 , wherein the medium comprises one or more compounds selected from the group of compounds of formulae CY, PY, and AC

wherein

denotes

denote

denotes

R 1 , R 2 ,
R AC1 , R AC2 each, independently of one another, denote alkyl having 1 to 12 C atoms, where, in addition, one or two non-adjacent CH 2 groups may each be replaced by —O—, —CH═CH—, —CO—, —OCO— or —COO— in such a way that O atoms are not linked directly to one another,
Z x , Z y , Z AC each, independently of one another, denote —CH 2 CH 2 —, —CH═CH—, —CF 2 O—, —OCF 2 —, —CH 2 O—, —OCH 2 —, —CO—O—, —O—CO—, —C 2 F 4 —, —CF═CF—, —CH═CH—CH 2 O— or a single bond,
L 1 , L 2 , L 3 , L 4 each, independently of one another, denote F, Cl, CN, OCF 3 , CF 3 , CH 3 , CH 2 F, or CHF 2 ,
a is 1 or 2,
b is 0 or 1,
c is 0, 1 or 2, and
d is 0 or 1.

7. The liquid-crystalline medium according to claim 1 , wherein the medium comprises one or more compounds selected from the group of compounds of formulae IIA to VIII

wherein

each, independently of one another, denote

identically or differently, denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH 2 groups in these radicals may each be replaced, independently of one another, by —C≡C—, —CF 2 O—, —CH═CH—,

—O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
X 20 identically or differently, denotes F, Cl, CN, SF 5 , SCN, NCS, a halogenated alkyl radical having 1 to 6 C atoms, a halogenated alkenyl radical having 2 to 6 C atoms, a halogenated alkoxy radical having 1 to 6 C atoms, or a halogenated alkenyloxy radical having 2 to 6

Assignees

• Merck Patent Gmbh

Inventors

• Junge Michael
• Ptak Ewa
• Wetzel Christoph

Classifications

• C09K19/608 Primary

  Quinoxaline dyes · CPC title

• C09K19/30

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

• C09K19/3003

  Compounds containing at least two rings in which the different rings are directly linked (covalent bond) · CPC title

• C09K19/3068

  chain containing -COO- or -OCO- groups · CPC title

• C09K19/3402

  having oxygen as hetero atom (sugars C09K19/0422) · CPC title