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

Patent metadata

Field	Value
Publication number	US-9688706-B2
Application number	US-201414891134-A
Country	US
Kind code	B2
Filing date	Jun 26, 2014
Priority date	Jun 27, 2013
Publication date	Jun 27, 2017
Grant date	Jun 27, 2017

Abstract

An electrochromic compound, represented by the following general formula (I);

where X 1 to X 4 are each a substituent represented by the following general formula (II), an alkyl group that may contain a functional group, an aromatic hydrocarbon group that may contain a functional group, or a hydrogen atom, and at least two selected from X 1 to X 4 are the substituents represented by the general formula (II);

where R 1 to R 8 are each independently a hydrogen atom, or a monovalent group that may contain a substituent; B is a substituted or unsubstituted monovalent group that may contain a functional group; A − is a monovalent anion; and m is any of 0 to 3, and R 1 to R 8 , B, and m may each independently be different when a plurality of the substituents represented by the general formula (II) are present.

First claim

The invention claimed is:

1. An electrochromic compound, represented by the following general formula (I):

where X 1 to X 4 are each a substituent represented by the following general formula (II), an alkyl group that may contain a functional group, an aromatic hydrocarbon group that may contain a functional group, or a hydrogen atom, and at least two selected from X 1 to X 4 are the substituents represented by the general formula (II):

where R 1 to R 8 are each independently a hydrogen atom, or a monovalent group that may contain a substituent; B is a substituted or unsubstituted monovalent group that may contain a functional group; A − is a monovalent anion; and m is any of 0 to 3, and R 1 to R 8 , B, and m may each independently be different when a plurality of the substituents represented by the general formula (II) are present.

2. The electrochromic compound according to claim 1 , wherein three selected from X 1 to X 4 in the general formula (I) are the substituents each represented by the general formula (II).

3. The electrochromic compound according to claim 1 , wherein any two selected from X 1 , X 2 , and X 4 are the substituents each represented by the general formula (II).

4. The electrochromic compound according to claim 1 , represented by the general formula (III):

where X 3 is a hydrogen atom, or a monovalent group that may contain a substituent; R 11 to R 31 are each independently a hydrogen atom, or a monovalent group that may contain a substituent; B 1 and B 2 are each independently a substituted or unsubstituted monovalent group that may contain a functional group; and A1 − and A2 − are each a monovalent anion.

5. The electrochromic compound according to claim 1 , represented by the following general formula (IV) or (V):

where X 3 is a hydrogen atom or a monovalent group that may contain a substituent; R 11 to R 31 are each independently a hydrogen atom or a monovalent group that may contain a substituent; B 1 and B 2 are each independently a substituted or unsubstituted aliphatic hydrocarbon group that may contain a functional group, or a substituted or unsubstituted aromatic hydrocarbon group that may contain a functional group; A1 − and A2 − are each a monovalent anion; m and n are each independently 1, 2, or 3; and Y is a bivalent organic group, which contains at least one methylene group, and may contain a substituted or unsubstituted aliphatic hydrocarbon group or a substituted or unsubstituted aromatic hydrocarbon group.

6. The electrochromic compound according to claim 1 , wherein at least one selected from all B present, or B1, or B2, or both contain a functional group capable of directly or indirectly bonding to a hydroxyl group.

7. The electrochromic compound according to claim 6 , wherein at least one selected from X 1 to X 4 in the general formula (I) contains a functional group capable of directly or indirectly bonding to a hydroxyl group.

8. The electrochromic compound according to claim 6 , wherein the functional group capable of directly or indirectly bonding to a hydroxyl group is a phosphonic acid group, a phosphoric acid group, a carboxylic acid group, a silyl group, or a silanol group.

9. An electrochromic composition, comprising:
the electrochromic compound according to claim 1 ; and
an electroconductive or semiconductive nanostructure, to which the electrochromic compound is bonded or adsorbed.

10. A display element, comprising:
a display electrode;
a counter electrode facing the display electrode with a space therebetween; and
an electrolyte provided between the display electrode and the counter electrode,
wherein the electrochromic compound according to claim 1 is provided on a surface of the display electrode.

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

12. An electrochromic compound, represented by the following general formula (Ia):

where at least two selected from X 1 , X 2 , and X 3 each have a structure represented by the general formula (IIa), and when two selected from X 1 , X 2 , and X 3 each have the structure represented by the general formula (IIa), the rest is an aliphatic hydrocarbon group that may contain a functional group, an aromatic hydrocarbon group that may contain a functional group, or a hydrogen atom; Y 1 to Y 8 are each independently a hydrogen atom, or a monovalent group that may contain a substituent; R is a substituted or unsubstituted monovalent group that may contain a functional group; and m is any of 0 to 3; A − is a monovalent anion, and Y 1 to Y 8 , m, and A − of the general formula (IIa) in X 1 , X 2 , or X 3 of the general formula (Ia) may be independently different.

13. The electrochromic compound according to claim 12 , wherein two selected from X 1 , X 2 , and X 3 of the general formula (Ia) each have a structure represented by the general formula (IIa).

14. The electrochromic compound according to claim 12 , wherein at least one of all R of the general formula (IIa) present contains a functional group capable of directly or indirectly bonding to a hydroxyl group.

15. The electrochromic compound according to claim 14 , wherein the functional group capable of directly or indirectly bonding to a hydroxyl group is a phosphonic acid group, a phosphoric acid group, a carboxylic acid group, a silyl group, or a silanol group.

16. The electrochromic compound according to claim 12 , wherein at least one selected from X 1 to X 3 of the general formula (Ia) contains a functional group capable of directly or indirectly bonding to a hydroxyl group.

Assignees

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

Inventors

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

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title

• G02F1/15

  based on an electrochromic effect · CPC title

• C09K9/02

  Organic tenebrescent materials · CPC title

• C07F7/1836

  Chemistry & Metallurgy · mapped topic