Non-fullerene electron acceptors for organic photovoltaic devices

Patent metadata

Field	Value
Publication number	US-9809594-B2
Application number	US-201414917553-A
Country	US
Kind code	B2
Filing date	Sep 10, 2014
Priority date	Sep 10, 2013
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

Non-fullerene electron acceptors for highly efficient organic photovoltaic devices are described. The non-fullerene electron acceptors have an extended, rigid, π-conjugated electron-deficient framework that can facilitate exciton and charge derealization. The non-fullerene electron acceptors can physically mix with a donor polymer and facilitate improved electron transport. The non-fullerene electron acceptors can be incorporated into organic electronic devices, such as photovoltaic cells.

First claim

What is claimed is:

1. A compound of Formula (I)

wherein:
EG and EG′ are each independently (W) m —W′,
wherein W is independently selected from arylene, heteroarylene, alkenylene, and alkynylene, each optionally substituted by 1, 2, 3, or 4 substituents independently selected from halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, CN, NO 2 , and OH;
W′ is independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, C 2-50 alkoxy, CN, NO 2 , and OH; and
m is 0, 1, or 2;

E is independently selected from

wherein R 2 is each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, C 2-50 alkoxy, CN, NO 2 , and OH;
Ar 1 is a π-conjugated linker;
R 1 is each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, C 2-50 alkoxy, CN, NO 2 , and OH;
x is 1 or 2.

2. The compound of claim 1 , having a weight average molecular weight of less than 5,000.

3. The compound of claim 1 , wherein E is

4. The compound of claim 1 , wherein R 1 is alkyl optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, and C 2-50 alkynyl.

5. The compound of claim 1 , wherein R 1 is

wherein R 7a and R 8a are each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, C 2-50 alkoxy, CN, NO 2 , and OH, wherein n′ and n″ are each 0 to 50.

6. The compound of claim 1 , wherein R 1 and R 2 are each independently selected from H, halo, alkyl, alkenyl, alkynyl, and alkoxy, wherein said alkyl, alkenyl, alkynyl, or alkoxy is optionally substituted with 1, 2, 3, 4, or 5 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, and C 2-50 alkynyl.

7. The compound of claim 1 , wherein W is independently selected from:

wherein Y is independently selected from O, S, SO 2 , Se, Te, N(R 3a ), C(R 3a ) 2 , Si(R 3a ) 2 , and Ge(R 3a ) 2 ;
X is independently selected from CR 6a and N; and
R 3a , R 4a , R 5a , and R 6a are each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, C 2-50 alkoxy, CN, NO 2 , and OH.

8. The compound of claim 7 , wherein W′ is independently selected from

wherein Y′ is independently selected from O, S, SO 2 , Se, Te, N(R 3b ), C(R 3b ) 2 , Si(R 3b ) 2 , and Ge(R 3b ) 2 ;
X′ is independently selected from CR 6b and N; and
R 3b , R 4b , R 5b , and R 6b are each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, C 2-50 alkoxy, CN, NO 2 , and OH.

9. The compound of claim 1 , wherein EG and EG′ are each independently selected from

10. The compound of claim 1 , provided that EG and EG′ are not both H, or both halo, and provided that when one of EG and EG′ is H, the other is not halo.

11. The compound of claim 8 , wherein Ar 1 is independently selected from

wherein Y″ is independently selected from O, S, SO 2 , Se, Te, N(R 3c ), C(R 3c ) 2 , Si(R 3c ) 2 , and Ge(R 3c ) 2 ;
X″ is independently selected from CR 6c and N; and
R 3c , R 4c , R 5c , and R 6c are each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO 2 , and OH, wherein said alkyl, alkenyl, alkynyl, alkoxy, aryl, heteroaryl, cycloalkyl, or heterocycloalkyl is optionally substituted with 1, 2, 3, or 4 substituents independently selected from halo, C 1-50 alkyl, C 2-50 alkenyl, C 2-50 alkynyl, C 2-50 alkoxy, CN, NO 2 , and OH.

12. The compound of claim 11 , wherein Ar 1 is selected from

13. The compound of claim 11 , wherein R 3a , R 4a , R 5a , R 6a , R

Assignees

• Univ Washington Through Its Center For Commercialization

Inventors

• Jenekhe Samson A
• Li Haiyan
• Earmme Taeshik
• Ren Guoqiang

Classifications

• H01L51/0053

  Electricity · mapped topic

• C07D471/22 Primary

  in which the condensed systems contains four or more hetero rings · CPC title

• C09B5/62

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title

• H01L51/0541

  Electricity · mapped topic

• C09B57/00

  Other synthetic dyes of known constitution · CPC title