Device for regulating the passage of energy

Patent metadata

Field	Value
Publication number	US-10364356-B2
Application number	US-201515534009-A
Country	US
Kind code	B2
Filing date	Nov 11, 2015
Priority date	Dec 9, 2014
Publication date	Jul 30, 2019
Grant date	Jul 30, 2019

Abstract

The present application relates to novel compounds and to devices which contain these compounds. The application also relates to a device for regulating the passage of energy from an outside space into an inside space, to a window containing the said device, and to uses of the said devices and compounds.

First claim

The invention claimed is:

1. Compound of the formula (I):

where:
X is equal to S or Se;
Z 1 is, independently of one another, a single bond, —CR 3 ═CR 3 — or —C≡C—; or two, three, four or five groups combined with one another, selected from the groups —CR 3 ═CR 3 — and —C≡C—;
Z 2 is, independently of one another, a single bond, O, S, C(R 3 ) 2 , —CR 3 ═CR 3 — or —C≡C—; or two, three, four or five groups combined with one another, selected from the groups O, S, C(R 3 ) 2 , —CR 3 ═CR 3 — and —C≡C—;
Ar 1 is, independently of one another, an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 4 ;
R 1 is, independently of one another, H, D, F, CN, N(R 5 ) 2 , or an alkyl, alkoxy or thioalkoxy group having 1 to 20 C atoms, which may be substituted by one or more radicals R 5 , where one or more CH 2 groups in the alkyl, alkoxy or thioalkoxy groups may be replaced by —R 5 C═CR 5 —, —C≡C—, C═O, C═S, —C(═O)O—, —OC(═O)—, Si(R 5 ) 2 , NR 5 , —O— or —S—;
R 3 , R 4 are, independently of one another, H, D, F, Cl, CN, or an alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms, which may be substituted by one or more radicals R 5 , where one or more CH 2 groups in the alkyl, alkoxy or thioalkoxy groups may be replaced by —R 5 C≡CR 5 —, —C≡C—, C═O, C═S, —C(═O)O—, —OC(═O)—, Si(R 5 ) 2 , NR 5 , —O— or —S—;
R 5 is, independently of one another, H, D, F, Cl, CN, N(R 6 ) 2 , an alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms or an alkenyl or alkynyl group having 2 to 20 C atoms, where the above-mentioned groups may each be substituted by one or more radicals R 6 and where one or more CH 2 groups in the above-mentioned groups may be replaced by —R 6 C═CR 6 —, —C≡C—, C═O, C═S, —C(═O)O—, —O(C═O)—, Si(R 6 ) 2 , NR 6 , —O— or —S—, or an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may in each case be substituted by one or more radicals R 6 ;
R 6 is, independently of one another, H, F or an aliphatic organic radical having 1 to 20 C atoms, in which one or more H atoms may be replaced by F, or an aryl or heteroaryl group having 5 to 20 C atoms, in which one or more H atoms may be replaced by F; and
i is, independently of one another, equal to 0, 1, 2, 3, 4 or 5.

2. Compound according to claim 1 , characterised in that X is equal to S and/or in that Z 1 is a single bond.

3. Compound according to claim 1 , characterised in that Z 2 stands, independently of one another, for a single bond, —C(R 3 ) 2 C(R 3 ) 2 —, —CR 3 ═CR 3 , —C≡C—, —OC(R 3 ) 2 — or —C(R 3 ) 2 O—.

4. Compound according to claim 1 , characterised in that Z 1 and Z 2 stand for a single bond.

5. Compound according to claim 1 , characterised in that Ar 1 represents, independently of one another, an aryl group having 6 to 15 C atoms or a heteroaryl group having 5 to 15 C atoms, which may be substituted by one or more radicals R 4 .

6. Compound according to claim 1 , characterised in that Ar 1 is selected on each occurrence from benzene, fluorene, naphthalene, pyridine, pyrimidine, pyrazine, triazine, thiophene, thiophene with condensed-on 1,4-dioxane ring, benzothiophene, dibenzothiophene, benzodithiophene, cyclopentadithiophene, thienothiophene, indenothiophene, dithienopyrrole, silolodithiophene, selenophene, benzoselenophene, dibenzoselenophene, furan, benzofuran, dibenzofuran and quinoline, each of which is optionally substituted by radicals R 4 .

7. Compound according to claim 1 , characterised in that at least one Ar 1 is selected from a sulfur-containing heteroaryl group, which may be substituted by one or more radicals R 4 .

8. Compound according to claim 1 , characterised in that R 1 is selected, independently of one another, from H, F, or a straight-chain alkyl or alkoxy group having 3 to 20 C atoms, which may be substituted by one or more radicals R 5 , or a branched alkyl or alkoxy group having 3 to 20 C atoms, which may be substituted by one or more radicals R 5 , or a cyclic alkyl group having 6 C atoms, which may be substituted by one or more radicals R 5 , where one or more CH 2 groups in the alkyl and alkoxy groups may be replaced by —O—, —S— or —R 5 C═CR 5 —, or a siloxanyl group having 1 to 6 Si atoms, which may be substituted by one or more radicals R 5 .

9. Compound according to claim 1 , characterised in that R 1 is, independently of one another, a branched alkyl group having 4 to 15 C atoms.

10. Compound according to claim 1 , characterised in that the index i is equal to 1 or 2.

11. Compound according to claim 1 , characterised in that the degree of anisotropy R of the compound of the formula (I) is greater than 0.4.

12. A device for regulating the passage of energy from an outside space into an inside space which is a window or switchable window where the device contains a switching layer, where the switching layer comprises one or more compounds of the formula (I).

13. A device according to claim 12 , characterised in that, besides the compound of the formula (I), a liquid-crystalline medium comprising one or more different compounds is present in the switching layer.

14. A device according to claim 12 , characterised in that it is electrically switchable.

15. A device according to claim 12 , characterised in that it is connected to a solar cell or another device for conversion of light and/or heat energy into electrical energy.

Assignees

• Merck Patent Gmbh

Inventors

• Kirsch Peer
• Gunst Susann
• Junge Michael
• Beyer Andreas
• Patwal Ursula

Classifications

• F24S20/63

  in the form of windows · CPC title

• C09K2219/13

  used in the technical field of thermotropic switches · CPC title

• C09K19/60

  Pleochroic dyes · CPC title

• C09K19/3497 Primary

  the heterocyclic ring containing sulfur and nitrogen atoms · CPC title

• C09B57/00 Primary

  Other synthetic dyes of known constitution · CPC title