Electrochromic compound, electrochromic composition, display element, and dimming element

Patent metadata

Field	Value
Publication number	US-9932522-B2
Application number	US-201515315103-A
Country	US
Kind code	B2
Filing date	Jun 17, 2015
Priority date	Jul 3, 2014
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

To provide an electrochromic compound, represented by the following general formula (I), where Ar 1 is a pyridinium ring having a structure represented by the following general formula (IIa), (IIb), or (IIc), where Ar 2 is a monovalent heterocyclic ring which may have a substituent, but Ar 2 is not a pyridinium ring; R 1 to R 8 are each independently a monovalent group which may have a functional group, where the monovalent group may have a substituent; A is a monovalent group which may have a functional group, where the monovalent group may have a substituent; and B − is a monovalent anion.

First claim

The invention claimed is:

1. An electrochromic compound represented by formula (I):

wherein:
Ar 1 is a pyridinium ring having a structure represented by formula (IIa), (IIb), or (IIc):

Ar 2 is a monovalent heterocyclic ring optionally containing a substituent, with the proviso that Ar 2 is not a pyridinium ring;
R 1 to R 8 are each independently a monovalent group optionally containing a functional group, and optionally containing a substituent;
A is a monovalent group optionally containing a functional group, and optionally containing a substituent; and
B − is a monovalent anion.

2. The electrochromic compound according to claim 1 , wherein Ar 2 is a C2-C20 heterocyclic ring containing a nitrogen atom, a sulfur atom, an oxygen atom, a selenium atom, a silicon atom, or any combination thereof.

3. The electrochromic compound according to claim 1 , wherein the monovalent group A has a functional group capable of binding to a hydroxyl group.

4. The electrochromic compound according to claim 3 , wherein the functional group capable of binding to a hydroxyl group is a phosphonic acid group, a phosphoric acid group, a carboxylic acid group, a silyl group, or a silanol group.

5. The electrochromic compound according to claim 4 , wherein the functional group capable of binding to a hydroxyl group is a phosphonic acid group.

6. The electrochromic compound according to claim 1 , wherein B − is a Br ion (Br − ), a Cl ion (Cl − ), a I ion (I − ), a OTf (triflate) ion (OTf − ), a ClO 4 ion (ClO 4 − ), a PF 6 ion (PF 6 − ), a BF 4 ion (BF 4 − ), or any combination thereof.

7. A dimming element, comprising:
a display electrode;
a counter electrode provided to face the display electrode with a space between the display electrode and the counter electrode; and
an electrolyte provided between the display electrode and the counter electrode,
wherein:
the electrochromic compound according to claim 1 is provided at a surface of the display electrode; and
the display electrode, the counter electrode, and the electrolyte are transparent.

8. An electrochromic composition, comprising:
an electrochromatic compound represented by formula (I):

 and
an electrically conductive or semiconductive nanostructure, wherein:
Ar 1 is a pyridinium ring having a structure represented by formula (IIa), (IIb), or (IIc):

Ar 2 is a monovalent heterocyclic ring optionally containing a substituent, with the proviso that Ar 2 is not a pyridinium ring;
R 1 to R 8 are each independently a monovalent group optionally containing a functional group, and optionally containing a substituent;
A is a monovalent group optionally containing a functional group, and optionally containing a substituent;
B − is a monovalent anion; and
the electrochromic compound is bonded to, or adsorbed on the electrically conductive or semiconductive nanostructure.

9. The electrochromic composition according to claim 8 , wherein the electrically conductive or semiconductive nanostructure comprises titanium oxide particles.

10. A display element, comprising:
a display electrode;
a counter electrode provided to face the display electrode with a space between the display electrode and the counter electrode; and
an electrolyte provided between the display electrode and the counter electrode,
wherein a display layer comprising the electrochromic composition according to claim 8 is provided at a surface of the display electrode.

11. A dimming element, comprising:
a display electrode;
a counter electrode provided to face the display electrode with a space between the display electrode and the counter electrode; and
an electrolyte provided between the display electrode and the counter electrode,
wherein:
the electrochromic composition according to claim 7 is provided at a surface of the display electrode; and
the display electrode, the counter electrode, and the electrolyte are transparent.

12. A display element, comprising:
a display electrode;
a counter electrode provided to face the display electrode with a space between the display electrode and the counter electrode; and
an electrolyte provided between the display electrode and the counter electrode,
wherein:
a display layer comprising an electrochromatic compound represented by formula (I) is provided at a surface of the display electrode:

Ar 1 is a pyridinium ring having a structure represented by formula (IIa), (IIb), or (IIc):

Ar 2 is a monovalent heterocyclic ring optionally containing a substituent, with the proviso that Ar 2 is not a pyridinium ring;
R 1 to R 8 are each independently a monovalent group optionally containing a functional group, and optionally containing a substituent;
A is a monovalent group optionally containing a functional group, and optionally containing a substituent; and
B − is a monovalent anion.

Assignees

• Goto Daisuke
• Sagisaka Toshiya
• Hirano Shigenobu
• Yamamoto Satoshi
• Inoue Mamiko
• Yashiro Tohru
• Takahashi Hiroyuki
• Fujimura Koh
• Horiuchi Tamotsu
• Yutani Keiichiroh
• Naijo Yoshihisa
• Okada Yoshinori
• Tsuji Kazuaki
• Kim Sukchan
• Takauji Keigo
• Ricoh Co Ltd

Inventors

• Goto Daisuke
• Sagisaka Toshiya
• Hirano Shigenobu
• Yamamoto Satoshi
• Inoue Mamiko
• Yashiro Tohru
• Takahashi Hiroyuki
• Fujimura Koh
• Horiuchi Tamotsu
• Yutani Keiichiroh
• Naijo Yoshihisa
• Okada Yoshinori
• Tsuji Kazuaki
• Kim Sukchan
• Takauji Keigo

Classifications

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09K9/02 Primary

  Organic tenebrescent materials · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1074

  containing more than three nitrogen atoms as heteroatoms · CPC title