Electrochromic device comprising electrochromic compound and manufacturing method therefor

Patent metadata

Field	Value
Publication number	US-11422425-B2
Application number	US-201816607237-A
Country	US
Kind code	B2
Filing date	Jul 4, 2018
Priority date	Jul 10, 2017
Publication date	Aug 23, 2022
Grant date	Aug 23, 2022

Abstract

The present application relates to an electrochromic device comprising a compound for electrochromism represented by Chemical Formula 1, and a method for manufacturing same.

First claim

What is claimed is:

1. An electrochromic device comprising:
a substrate;
a first electrode on the substrate;
a second electrode on the first electrode;
an electrolyte layer between the first electrode and the second electrode; and
an electrochromic layer comprising one or more layers between the electrolyte layer and the second electrode,
wherein the one or more layers of the electrochromic layer comprise a compound for electrochromism of Chemical Formula 1:

wherein:
Ra and Rb are the same as or different from each other, and each is independently a group functioning as an electron acceptor;
Y1 to Y5 are the same as or different from each other, and each is independently CRR′, NR, O, SiRR′, PR, S, GeRR′, Se or Te;
Y6 and Y7 are different from each other, and each is independently a direct bond, CRR′, NR, O, SiRR′, PR, S, GeRR′, Se or Te;
a is 0 or 1;
when a is 0, Y6 is a direct bond, and Y7 is CRR′, NR, O, SiRR′, PR, S, GeRR′, Se or Te;
when a is 1, Y7 is a direct bond, and Y6 is CRR′, NR, O, SiRR′, PR, S, GeRR′, Se or Te;
n and m are each an integer of 0 to 5;
when n and m are 2 or greater, structures in the parentheses are the same as or different from each other;
Z1 to Z4 are the same as or different from each other, and each is independently CRR′R″, NRR′, OR, SiRR′R″, PRR′, SR, GeRR′R″, SeR or TeR; and
R1, R2, R, R′ and R″ are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, an imide group, an amide group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

2. The electrochromic device of claim 1 , wherein the compound of Chemical Formula 1 is a compound of Chemical Formula 2 or 3:

wherein:
Ra and Rb are the same as or different from each other, and each is independently a group functioning as an electron acceptor;
Y1 to Y7 are the same as or different from each other, and each is independently CRR′, NR, O, SiRR′, PR, S, GeRR′, Se or Te;
n and m are each an integer of 0 to 5;
when n and m are 2 or greater, structures in the parentheses are the same as or different from each other;
Z1 to Z4 are the same as or different from each other, and each is independently CRR′R″, NRR′, OR, SiRR′R″, PRR′, SR, GeRR′R″, SeR or TeR; and
R1, R2, R, R′ and R″ are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, an imide group, an amide group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

3. The electrochromic device of claim 2 , wherein the compound of Chemical Formula 3 is a compound of Chemical Formula 1-1 or 1-2:

wherein:
Ra and Rb are the same as or different from each other, and each is independently a group functioning as an electron acceptor;
Y1 to Y6 are the same as or different from each other, and each is independently CRR′, NR, O, SiRR′, PR, S, GeRR′, Se or Te;
Z1 to Z4 are the same as or different from each other, and each is independently CRR′R″, NRR′, OR, SiRR′R″, PRR′, SR, GeRR′R″, SeR or TeR; and
R1, R2, R, R′ and R″ are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, an imide group, an amide group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

4. The electrochromic device of claim 1 , wherein Ra and Rb are the same as or different from each other, and each is any one of the following structures:

wherein:
c is an integer of 1 to 4;
when c is 2 or greater, structures in the two or more parentheses are the same as or different from each other; and
R10 to R13 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, an imide group, an amide group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthioxy group, a substituted or unsubstituted arylthioxy group, a substituted or unsubstituted alkylsulfoxy group, a substituted or unsubstituted arylsulfoxy group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted boron group, a substituted or unsubstituted alkylamine group, a substituted or unsubstituted aralkylamine group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

5. The electrochromic device of claim 4 , wherein R10 to R13 are the same as or different from each other, and each is independently hydrogen or a substituted or unsubstituted alkyl group.

6. The electrochromic device of claim 5 , wh

Assignees

• Lg Chemical Ltd

Inventors

• Lim Bogyu
• Lee Jiyoung
• Kim Ji Hoon

Classifications

• C07D495/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K9/02 Primary

  Organic tenebrescent materials · CPC title

• G02F1/1516 Primary

  comprising organic material · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title