Organic photosensitive devices comprising aryl squaraines and methods of making the same

Patent metadata

Field	Value
Publication number	US-11944007-B2
Application number	US-201916449881-A
Country	US
Kind code	B2
Filing date	Jun 24, 2019
Priority date	Feb 9, 2011
Publication date	Mar 26, 2024
Grant date	Mar 26, 2024

Abstract

There is disclosed squaraine compounds of formula I:wherein each of Y1 and Y2 is independently chosen from an optionally substituted amino group and an optionally substituted aryl group. Also described are organic optoelectronic devices comprising a Donor-Acceptor heterojunction that is formed from one or more of the squaraine compounds. A method of making the disclosed device, which may include one or more sublimation step for depositing said squaraine compound, is also disclosed.

First claim

What is claimed is:

1. A squaraine compound of formula I:

wherein,
Y 1 and Y 2 are independently chosen from —NR 3 R 4 and a group of formula II

wherein X for each occurrence is independently chosen from hydrogen and hydroxyl;
R 1 and R 2 are taken together with any intervening atoms to form a group chosen from optionally substituted heteroaryl and optionally substituted heterocyclyl;
wherein one of Y 1 or Y 2 is —NR 3 R 4 ;
R 3 and R 4 are taken together with any intervening atoms to form a group chosen from optionally substituted heteroaryl and optionally substituted heterocyclyl, and the optionally substituted heteroaryl and the optionally substituted heterocyclyl are independently chosen from monocyclic and multicyclic groups.

2. The compound of claim 1 , wherein Y 1 is —NR 3 R 4 .

3. The compound of claim 1 , wherein Y 2 is chosen from a group of formula II

4. The compound of claim 3 , wherein Y 1 is —NR 3 R 4 and the optionally substituted heteroaryl and the optionally substituted heterocyclyl are independently chosen from monocyclic and multicyclic groups.

5. A squaraine compound of the formula:

{2-[4-(N,N-diisobutylamino)-2,6-dihydroxyphenyl]-4-diphenylamino} squaraine (USSQ).

6. The compound of claim 3 , wherein the group of formula II is chosen from a group of formula III:

wherein
W is chosen from S, O, Se, and Te;
n is an integer chosen from 0 and 1; and
R 5 and R 6 are independently chosen from optionally substituted amino, cyano, halo, mercapto, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkyl, optionally substituted aryl, and optionally substituted heteroaryl, optionally substituted heterocyclyl, and optionally substituted carbocyclyl, or
R 5 and R 6 attached to adjacent atoms are taken together with any intervening atoms to form a group chosen from optionally substituted aryl, optionally substituted heteroaryl, optionally substituted carbocyclyl, and optionally substituted heterocyclyl.

7. The compound of claim 1 , wherein Y 2 is —NR 3 R 4 .

8. An organic photosensitive optoelectronic device comprising at least one compound of claim 1 , wherein the device comprises at least one donor-acceptor heterojunction.

9. A squaraine compound of the formula:

{2-[4-(N,N-diphenylamino)-2,6-dihydroxyphenyl]-4-diphenylamino} squaraine (DPUSQ).

Assignees

• Univ Michigan Regents
• Univ Southern California

Inventors

• Thompson Mark E
• Forrest Stephen R
• Wei Guodan
• Wang Siyi
• Hall Lincoln
• Diev Viacheslav V
• Xiao Xin

Classifications

• H10K30/50

  Photovoltaic [PV] devices · CPC title

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• Y02E10/542

  Dye sensitized solar cells · CPC title

• C07C2601/04

  with a four-membered ring · CPC title