Device for controlling the passage of energy, containing a dichroic dye compound

Patent metadata

Field	Value
Publication number	US-10344217-B2
Application number	US-201414893618-A
Country	US
Kind code	B2
Filing date	Apr 29, 2014
Priority date	May 24, 2013
Publication date	Jul 9, 2019
Grant date	Jul 9, 2019

Abstract

The present application relates to a device for regulating the passage of energy from an outside space into an inside space, where the device comprises a switching layer comprising one or more dichroic dyes of a formula (I) or formula (II).

First claim

The invention claimed is:

1. A device for regulating the passage of energy in the form of light emitted by the sun from the environment into an inside space, where the device comprises a switching layer comprising one or more dichroic dyes of formula (I)

or formula (II)

where:
X is on each occurrence, identically or differently, CR 2 or N;
Y is equal to S or Se;
Z 1 is on each occurrence, identically or differently, a single bond, —CR 3 ═CR 3 —or —C≡C—;
Z 2 is on each occurrence, identically or differently, a single bond, O, S, C(R 3 ) 2 , —CR 3 ═CR 3 — or —C≡C—;
Ar 1 is on each occurrence, identically or differently, 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 on each occurrence, identically or differently, N(R 5 ) 2 or a straight-chain or branched alkyl or alkoxy having 3 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 or alkoxy groups may each be replaced by —O—, —S—, —R 5 C═CR 5 —, or a siloxanyl group having 1 to 10 Si atoms, which may be substituted by one or more radicals R 5 ;
R 2 is on each occurrence, identically or differently, H, D, F, Cl, CN, —(C═O)OR 5 , —O(C═O)R 5 , 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 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 3 , R 4 are on each occurrence, identically or differently, 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 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 on each occurrence, identically or differently, 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 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 on each occurrence, identically or differently, 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 each be replaced by F;
i is equal to 0, 1, 2, 3, 4 or 5; and
wherein said switching layer further comprises a liquid-crystalline medium having a clearing point in the temperature range from 90° C. to 170° C., wherein said medium comprises one or more different compounds,
wherein said device is capable of regulating the passage of energy in the form of light emitted by the sun from the environment into an inside space, and
wherein said device is
(a)electrically switchable from a state having relatively low light transmissivity into a state having higher light transmissivity; or
(b) electrically switchable from a state having relatively high light transmissivity into a state having lower light transmissivity.

2. The device according to claim 1 , wherein X is CR 2 .

3. The device according to claim 1 , wherein Y is S.

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

5. The device according to claim 1 , wherein Z 2 stands on each occurrence, identically or differently, 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—.

6. The device according to claim 1 , wherein Ar 1 represents on each occurrence, identically or differently, 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 .

7. The device according to claim 1 , wherein Ar 1 is on each occurrence, identically or differently, benzene, fluorene, naphthalene, pyridine, pyrimidine, pyrazine, triazine, thiophene, thiophene with condensed-on 1,4-dioxane ring, benzothiophene, dibenzothiophene, benzodithiophene, cyclopenta-dithiophene, thienothiophene, indenothiophene, dithienopyrrole, silolodithiophene, selenophene, benzoselenophene, dibenzoselenophene, furan, benzofuran, dibenzofuran, or quinoline, each of which is optionally substituted by radicals R 4 .

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

9. The device according to claim 1 , wherein R 1 is on each occurrence, identically or differently, a straight-chain or branched alkyl or alkoxy group having 3 to 8 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 each 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 .

10. The device according to claim 1 , wherein i is 1 or 2.

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

12. 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.

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

14. The device according to claim 1 , wherein said one or more compounds of formula (I) or formula (II) are selected from compounds of formula (I).

15. The device according to claim 1 , wherein said one or more or more dichroic dyes are selected from formula (IIa)

where:
Z 1 is on each occurrence, identically or differently, a single bond, —CR 3 ═CR 3 — or —C≡C—;
Z 2 is on each occurrence, identically or differently, a single bond, O, S, C(R 3 ) 2 , —CR 3 ═CR 3 — or —C≡C—;
Ar 1 is on each occurrence, identically or differently, 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 on each occurrence, identically or differently, H, D, F, CN, N(R 5 ) 2 , 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 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 2 is on each occurrence, identically or differently, N(R 5 ) 2 or a straight-chain or branched alkyl or alkoxy having 3 to 10 H 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 each be replaced by —O—, —S—, —R 5 C═CR 5 —, or a siloxanyl group having 1 to 10 Si atoms, which may be substituted by one or more radicals R 5 ;
R 3 , R 4 are on each occurrence, identically or differently, H, D, F, Cl, CN, or an alkyl, alkoxy or thioalkoxy group having 1 to 10 C atoms, which

Assignees

• Merck Patent Gmbh

Inventors

• Kirsch Peer
• Hahn Alexander
• Ruhl Andreas
• Beck Susann
• Pan Junyou
• Junge Michael
• Beyer Andreas
• Patwal Ursula

Classifications

• C09K19/60 Primary

  Pleochroic dyes · CPC title

• C07D417/14

  containing three or more hetero rings · CPC title

• C09B23/105

  two >CH- groups · CPC title

• C07D285/14

  condensed with carbocyclic rings or ring systems · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title