Azo compound, ink containing azo compound, and display and electronic paper containing the ink

Patent metadata

Field	Value
Publication number	US-9732226-B2
Application number	US-201514610412-A
Country	US
Kind code	B2
Filing date	Jan 30, 2015
Priority date	Aug 1, 2012
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

An azo compound excellent in solubility in solvent and having a high absorbance coefficient is disclosed, as well as an ink containing the azo compound. Such an ink contains a solvent having a relative permittivity at 22° C. and at a measurement frequency of 1 kHz of 3 or less and having a solubility in water at 25° C. of 20 mg/L or less, and an azo compound.

First claim

The invention claimed is:

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

wherein:
R 1 and R 2 each independently represent a hydrocarbon group optionally having a substituent, wherein at least one of R 1 and R 2 is a branched alkyl group having from 6 to 20 carbon atoms; and
X 1 , X 11 and A 1 each independently represent a hydrogen atom or a substituent.

2. The ink of claim 1 , wherein the solvent comprises at least one solvent selected from a group consisting of a hydrocarbon solvent, a silicone oil and a fluorocarbon solvent.

3. The ink of claim 1 , wherein a product εC of a molar absorbance coefficient ε(L·mol −1 ·cm −1 ) at absorption maximum wavelength of an n-decane solution of the azo compound, and a saturation solubility C (mol·L −1 ) of the solution at 5° C. is 1000 cm −1 or more.

4. The ink of claim 1 , further comprising:
at least one compound selected from a group consisting of a heterocyclic compound, a cyanovinyl compound and an anthraquinone compound.

5. The ink of claim 4 , wherein the heterocyclic compound is at least one compound selected from a group consisting of formulae (2) to (5):

wherein:
R 101 and R 102 each independently represent a hydrogen atom or an arbitrary substituent:
D 3 and D 4 each independently represent an arbitrary substituent,
e represents an integer of from 0 to 5, and when e is 2 or more, 2 or more D 3 s existing in one molecule may be the same or different;
g represents an integer of from 0 to 4, and when g is 2 or more, 2 or more D 4 s existing in one molecule may be the same or different,

wherein:
R 201 to R 208 each independently represent a hydrogen atom or a substituent;
Z represents a nitrogen atom or a methine group optionally having a substituent,

wherein:
R 301 , R 302 , D 5 and D 6 each independently represent a substituent;
l represents an integer of from 0 to 4, and when l is 2 or more, 2 or more D 5 s existing in one molecule may be the same or different;
j represents an integer of from 0 to 4, and when j is 2 or more, 2 or more D 6 s existing in one molecule may be the same or different, and

wherein:
R 601 , R 602 , D 9 and D 10 each independently represent a substituent;
A 3 represents a hydrogen atom or a substituent;
p represents an integer of from 0 to 5, and when p is 2 or more, 2 or more D 9 s existing in one molecule may be the same or different;
q represents an integer of from 0 to 4, and when q is 2 or more, 2 or more D 10 s existing in one molecule may be the same or different;
X 3 represents a nitrogen atom, or a methine group having a halogen atom, a cyano group or a group —COOR 605 as a substituent;
R 605 represents a hydrogen atom, an alkyl group having a carbon number of from 1 to 20 and optionally having a substituent, an aryl group having a carbon number of from 6 to 20 and optionally having a substituent, or a heteroaryl group having a carbon number of from 2 to 20 and optionally having a substituent.

6. The ink of claim 4 , comprising an anthraquinone compound represented by formula (7):

wherein:
D 8 represents a substituent;
t represents an integer of from 0 to 8, and when t is 2 or more, 2 or more D 8 s existing in one molecule may be the same or different.

7. The ink of claim 1 , which is adapted to function in displays or optical shutters.

8. A display, comprising a display area comprising the ink of claim 1 , and which displays an image by controlling a voltage application to the display area.

9. The display of claim 8 , wherein the display area further comprises at least either one of electrophoretic particles and an aqueous medium.

10. The display of claim 8 , which displays an image by changing the coloration state through control of voltage application.

11. The display of claim 8 , which displays an image according to an electrowetting system or an electrophoretic system.

12. An electronic paper, comprising the display of claim 8 .

13. An azo compound represented by formula (8):

wherein:
R 3 and R 4 each independently represent an alkyl group having a carbon number of from 1 to 20 and optionally having a substituent, wherein at least one of R 3 and R 4 is a branched alkyl group having from 6 to 20 carbon atoms;
R 5 represents an alkyl group having a branched chain and having a carbon number of from 4 to 20 and optionally having a substituent;
X 2 and X 12 each independently represent a hydrogen atom or a substituent.

14. The ink of claim 1 , wherein R 1 and R 2 are each independently a branched alkyl group having from 6 to 20 carbon atoms, X 11 is hydrogen, and X 1 is an acylamino group having from 1 to 20 carbon atoms and optionally having a branched chain and a cyclic structure.

15. The azo compound of claim 13 , wherein R 3 and R 4 are each independently a branched alkyl group having from 6 to 20 carbon atoms, X 12 is hydrogen, and X 2 is an acylamino group having from 1 to 20 carbon atoms and optionally having a branched chain and a cyclic structure.

Assignees

• Mitsubishi Chem Corp

Inventors

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

Classifications

• G02F1/167

  by electrophoresis · CPC title

• C07C311/08

  having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring · CPC title

• C09B29/081

  unsubstituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino, aralkylamino or arylamino · CPC title

• C09B29/0823

  substituted by CN · CPC title

• C07C255/59

  the carbon skeleton being further substituted by singly-bound oxygen atoms · CPC title