Azo compound, ink containing azo compound, display including said ink and electronic paper

Patent metadata

Field	Value
Publication number	US-9708498-B2
Application number	US-201514723256-A
Country	US
Kind code	B2
Filing date	May 27, 2015
Priority date	Nov 28, 2012
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

Abstract

The present invention relates to an ink comprising: a solvent having a relative permittivity, measured at a frequency of 1 kHz and a temperature of 22° C., of 3 or less and a solubility in water at 25° C. of 20 mg/L or less; and a specific azo compound.

First claim

The invention claimed is:

1. An ink comprising: a solvent having a relative permittivity, measured at a frequency of 1 kHz and a temperature of 22° C., of 3 or less and a solubility in water at 25° C. of 20 mg/L or less; and an azo compound represented by the following general formula (1):

wherein in the general formula (1),
R 1 represents any substituent,
R 2 represents a hydrogen atom or any substituent,
R 3 and R 4 each independently represent an alkyl group which may have a substituent, ring A represents general formula (2),
X represents a nitrogen atom, a methine group, or a methine group having a substituent, and general formula (2) is represented by the following formula:

wherein in the general formula (2),
R 5 represents a hydrogen atom or any substituent

2. The ink according to claim 1 , wherein the solvent comprises at least one member selected from the group consisting of hydrocarbon-based solvents, silicone oils, and fluorocarbon-based solvents.

3. The ink according to claim 1 , wherein a product εC of a molar extinction coefficient ε (Lmol −1 cm −1 ) at an absorption maximum wavelength in an n-decane solution of the azo compound and a saturation concentration C (molL −1 ) at 5° C. of the solution is 1,000 cm −1 or larger.

4. The ink according to claim 1 , which further comprises at least one member selected from the group consisting of heterocyclic compounds, cyanovinyl compounds, and anthraquinone compounds.

5. The ink according to claim 4 , wherein the heterocyclic compounds are at least one compound selected from the group consisting of the following general formulae (4) to (7):

wherein in the general formula (4),
R 101 and R 102 each independently represent a hydrogen atom or any substituent,
D 3 and D 4 each independently represent any substituent, e represents an integer of 0-5, and when e is 2 or larger, the two or more D 3 s present in the molecule may be the same or different, and
g represents an integer of 0-4, and when g is 2 or larger, the two or more D 4 s present in the molecule may be the same or different;

wherein in the general formula (5), R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , and R 208 each independently represent a hydrogen atom or any substituent, and
Z represents a nitrogen atom, a methine group or a methine group having a substituent;

wherein in the general formula (6),
R 301 , R 302 , D 5 , and D 6 each independently represent any substituent,
l represents an integer of 0-4, and when 1 is 2 or larger, the two or more D 5 s present in the molecule may be the same or different, and
j represents an integer of 0-4, and when j is 2 or larger, the two or more D 6 s present in the molecule may be the same or different;

wherein in the general formula (7), R 601 , R 602 , D 9 , or D 10 each independently represents any substituent,
A 1 represents a hydrogen atom or any substituent,
p represents an integer of 0-5, and when p is 2 or larger, the two or more D 9 s present in the molecule may be the same or different,
q represents an integer of 0-4, and when q is 2 or larger, the two or more D 10 s present in the molecule may be the same or different,
X 1 represents a nitrogen atom, a methine group, or a methine group having a halogen atom, a cyano group, or a —COOR 605 group as a substituent, and
R 605 represents a hydrogen atom, an alkyl group which has 1-20 carbon atoms and may have a substituent, an aryl group which has 6-20 carbon atoms and may have a substituent, or a heteroaryl group which has 2-20 carbon atoms and may have a substituent.

6. The ink according to claim 4 , wherein the anthraquinone compounds are represented by the following general formula (8):

wherein in the general formula (8),
D 8 represents any substituent, and
t represents an integer of 0-8, and when t is 2 or larger, the two or more D 8 s present in the molecule may be the same or different.

7. The ink according to claim 1 , which is for displays or for optical shutters.

8. A display which comprises a display part including the ink according to claim 1 , wherein an image is displayed by controlling voltage application to the display part.

9. The display according to claim 8 , wherein the display part includes electrophoretic particles or an aqueous medium.

10. The display according to claim 8 , wherein an image is displayed by causing a change in the coloration state by the voltage application.

11. The display according to claim 8 , wherein an image is displayed in an electrowetting mode or an electrophoresis mode.

12. An electronic paper which comprises the display according to claim 8 .

13. An azo compound represented by the following general formula (10):

wherein in the general formula (10),
R 21 represents any substituent,
R 22 and R 23 each independently represent a hydrogen atom or any substituent,
R 24 and R 25 each independently represent an alkyl group which may have a substituent,
X 2 represents a nitrogen atom or a methine group which may have a substituent, and
n′ represents an integer of 0-5.

Assignees

• Mitsubishi Chem Corp

Inventors

• Shiga Yasushi
• Kadowaki Tomoko
• Tanaka Yuki
• AOBA Mitsuya
• Ishida Mio

Classifications

• C09B31/14

  Heterocyclic components · CPC title

• C09D11/033

  characterised by the solvent · CPC title

• G02F2001/1678

  characterised by the composition or particle type · CPC title

• C09D11/52 Primary

  Electrically conductive inks · CPC title

• C09B31/043

  Amino-benzenes · CPC title