Device for regulating the passage of energy

Patent metadata

Field	Value
Publication number	US-10370592-B2
Application number	US-201515505975-A
Country	US
Kind code	B2
Filing date	Aug 10, 2015
Priority date	Aug 25, 2014
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

A device for regulating the passage of energy from an outside space into an inside space includes a switching layer, where the switching layer comprises one or more compounds of the formula:

wherein R 1 , Z 1 , Z 2 , Ar 1 and X are defined herein.

First claim

The invention claimed is:

1. A device for regulating the passage of energy from an outside space into an inside space, said device comprising a switching layer, where the switching layer comprises a liquid-crystalline medium containing one or more compounds of formula (I) and one or more different compounds:

where:
X is S;
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 —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 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 is unsubstituted or substituted by one or more radicals R 4 ;
R 1 is, independently of one another, a straight-chain or branched chain alkyl or group having 3 to 10 C atoms;
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 is unsubstituted or substituted by one or more radicals R 5 , where one or more CH 2 groups in the alkyl, alkoxy or thioalkoxy groups may each 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 are each unsubstituted or substituted by one or more radicals R 6 and where one or more CH 2 groups in the above-mentioned groups may each 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 each be replaced by F, or an aryl or heteroaryl group having 5 to 20 C atoms, in which one or more H atoms may each be replaced by F; and
i is, independently of one another, equal to 1, 2, 3, 4 or 5.

2. The device according to claim 1 , wherein Z 1 is a single bond.

3. The device according to claim 1 , wherein Z 2 is in each case, independently of one another, 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. The device according to claim 1 , wherein Ar 1 is in each case, independently of one another, an aryl group having 6 to 15 C atoms or a heteroaryl group having 5 to 15 C atoms, which in each case is unsubstituted or substituted by one or more radicals R 4 .

5. The device according to claim 1 , wherein Ar 1 is in each case 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, or quinoline, which in each case is optionally substituted by radicals R 4 .

6. The device according to claim 1 , wherein at least one Ar 1 is a sulfur-containing heteroaryl group, which is unsubstituted or substituted by one or more radicals R 4 .

7. The device according to claim 1 , wherein R 1 is in each case, independently of one another, a straight-chain alkyl having 3 to 10 C atoms.

8. The device according to claim 1 , index i is 1 or 2.

9. The device according to claim 1 , wherein the degree of anisotropy R of the compound of formula (I) is greater than 0.4.

10. The device according to claim 1 , wherein said device is electrically switchable.

11. The device according to claim 1 , wherein said device is connected to a solar cell or another device for conversion of light and/or heat energy into electrical energy.

12. A window comprising a device according to claim 1 .

13. An electrochemical device comprising a compound according to formula (I):

where:
X is S;
Z 1 is, independently of one another, a single bond, —CR 3 ═CR 3 — or —C≡C—; or two, three, four or five Z 1 groups combined with one another, are selected —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 Z 2 groups combined with one another, are selected from 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 is unsubstituted or substituted by one or more radicals R 4 ;
R 1 is, independently of one another, a straight-chain or branched chain alkyl or alkoxy group having 3 to 10 C atoms;
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 is unsubstituted or substituted by one or more radicals R 5 , where one or more CH 2 groups in the alkyl, alkoxy or thioalkoxy groups may each 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 are in each case unsubstituted or substituted by one or more radicals R 6 and where one or more CH 2 groups in the above-mentioned groups may each 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 in each case is unsubstituted or 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 each be replaced by F, or an aryl or heteroaryl group having 5 to 20 C atoms, in which one or more H atoms each be replaced by F; and
i is, independently of one another, equal to 1, 2, 3, 4 or 5.

14. A window, organic solar cell, or organic electronic component comprising a liquid-crystalline mixture comprising at least one compound according to formula (I):

where:
X is S;
Z 1 is, independently of one another, a single bond, —CR 3 ═CR 3 — or —C≡C—; or two, three, four or five Z 1 groups combined with one another, are selected —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 Z 2 groups combined with one another, are selected from 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 is unsubstituted or substituted by one or more radicals R 4 ;
R 1 is, independently of one another, a straight-chain or branched chain alkyl or alkoxy group having 3 to 10 C atoms;
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 is unsubstituted or substituted by one or more radicals R 5 , where on

Assignees

• Merck Patent Gmbh
• Merch Patent Gmbh

Inventors

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

Classifications

• C09K2219/13

  used in the technical field of thermotropic switches · CPC title

• C09K19/60 Primary

  Pleochroic dyes · CPC title

• C09B5/62

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title

• C09K19/3497

  the heterocyclic ring containing sulfur and nitrogen atoms · CPC title

• C09K19/601

  Azoic · CPC title