Dye compounds

• US 10,202,508 B2
• Filed: 11/19/2014
• Issued: 02/12/2019
• Est. Priority Date: 12/19/2013
• Status: Active Grant

• Current Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Original Assignee: Merck Patent GmbH (Merck & Co., Inc.)
• Inventors: Tong, Qiong, Kirsch, Peer, Junge, Michael, Patwal, Ursula, Beyer, Andreas
• Primary Examiner(s): Robinson, Chanceity N
• Assistant Examiner(s): Malloy, Anna
• Application Number:
  US15/106,631
• Publication Number:
  US 20170002203A1
• Time in Patent Office: 1,546 Days
• CPC Class Codes: C09B 57/004 Diketopyrrolopyrrole dyes
• CPC Class Codes: C09K 19/60 Pleochroic dyes
• CPC Class Codes: G02F 1/1337 Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers

Abstract

Mixtures containing at least one dye compound having a diketopyrrolopyrrole structure and at least one further liquid-crystalline compound are suitable for use in devices for regulating the entry of light into a space.

Claims

1. A mixture comprising one or more compounds selected from compounds (5), (6), (7), (8), (11), and (13):

2. The mixture according to claim 1, wherein the degree of anisotropy R of said one or more compounds selected from compounds (5), (6), (7), (8), (11), and (13) is greater than 0.6.

3. The mixture according to claim 1, wherein said mixture comprises precisely one, two, three or four different compounds selected from compounds (5), (6), (7), (8), (11), and (13).

4. The mixture according to claim 1, wherein said mixture is a thermotropic liquid-crystalline material.

5. The mixture according to claim 1, wherein said 3 to 25 different liquid-crystalline compounds are selected from liquid-crystalline compounds containing two, three or four structural elements, wherein each of said structural elements contains a 1,4-phenylene and/or 1,4-cyclohexylene group.

6. The mixture according to claim 1, wherein said mixture additionally contains one or more dye compounds having a different structure than compounds (5), (6), (7), (8), (11), and (13).

7. The mixture according to claim 6, the one or more additional dye compounds having a different structure than compounds (5), (6), (7), (8), (11), and (13) are selected from perylenes, terrylenes, benzothiadiazoles and azo dyes.

8. A method for regulating the entry of light from one space into another space comprising passing said light through a device containing a switching layer wherein said switching layer contains a mixture according to claim 1.

9. A device for regulating the entry of light into a space, comprising a mixture according to claim 1.

10. The device according to claim 9, wherein said device comprises the following layer sequence, where further layers may additionally be present:

a first substrate layer,

a first electrically conductive transparent layer,

a first alignment layer,

a switching layer comprising said mixture,

a second alignment layer,

a second electrically conductive transparent layer, and

a second substrate layer.

11. A window containing a device according to claim 9.

15. The mixture according to claim 1, wherein each individual compound selected from the compounds (5), (6), (7), (8), (11), and (13) is present in said mixture in a proportion of 0.01 to 10% by weight.

16. The mixture according to claim 1, wherein said mixture has an optical anisotropy (Δ

n) of 0.01 to 0.3.

17. The mixture according to claim 1, wherein said mixture comprises one or more chiral dopants in a total concentration of 0.01 to 3% by weight.

12. A mixture comprising at least one compound of formula (I-1-5)

13. The mixture according to claim 12, wherein

U is equal to C(R⁴)₂;

Z² is on each occurrence, identically or differently, a single bond or a group selected from O, S, C(R³)₂, —

C(R³)₂O—

, —

OC(R³)₂—

, —

CR³═

CR³— and

—

C≡

C—

;

R¹ is on each occurrence, identically or differently, F or a straight-chain alkyl or alkoxy group having 3 to 12 C atoms, which may be substituted by one or more radicals R⁵, or a branched alkyl or alkoxy group having 3 to 12 C atoms, which may be substituted by one or more radicals R⁵, or a cyclic alkyl group having 6 C atoms, which may be substituted by one or more radicals R⁵, where one or more CH₂ groups in the alkyl and alkoxy groups may be replaced by —

O—

or —

S—

;

R² is on each occurrence, identically or differently, an alkyl group having 1 to 12 C atoms, which may be substituted by one or more radicals R⁵, particularly preferably a branched alkyl group having 3 to 12 C atoms, which may be substituted by one or more radicals R⁵.

14. The mixture according to claim 12, wherein said compounds of formula (I-1-5) are selected from the following compounds: