US 9,809,594 B2
Non-fullerene electron acceptors for organic photovoltaic devices
Samson A. Jenekhe, Seattle, WA (US); Haiyan Li, Seattle, WA (US); Taeshik Earmme, Seattle, WA (US); and Guoqiang Ren, Seattle, WA (US)
Assigned to UNIVERSITY OF WASHINGTON THROUGH ITS CENTER FOR COMMERCIALIZATION, Seattle, WA (US)
Appl. No. 14/917,553
Filed by University of Washington Through its Center for Commercialization, Seattle, WA (US)
PCT Filed Sep. 10, 2014, PCT No. PCT/US2014/055030
§ 371(c)(1), (2) Date Mar. 8, 2016,
PCT Pub. No. WO2015/038671, PCT Pub. Date Mar. 19, 2015.
Claims priority of provisional application 61/876,055, filed on Sep. 10, 2013.
Prior Publication US 2017/0057962 A1, Mar. 2, 2017
Int. Cl. C07D 471/22 (2006.01); H01L 51/00 (2006.01); C09B 5/62 (2006.01); C09B 57/00 (2006.01); H01L 51/05 (2006.01); H01L 51/42 (2006.01)
CPC C07D 471/22 (2013.01) [C09B 5/62 (2013.01); C09B 57/00 (2013.01); H01L 51/0053 (2013.01); H01L 51/0072 (2013.01); H01L 51/0541 (2013.01); H01L 51/4253 (2013.01); Y02E 10/549 (2013.01)] 19 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Drawing
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, NO2, 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, C1-50 alkyl, C2-50 alkenyl, C2-50 alkynyl, CN, NO2, and OH;
W′ is independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO2, 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, C1-50 alkyl, C2-50 alkenyl, C2-50 alkynyl, C2-50 alkoxy, CN, NO2, and OH; and
m is 0, 1, or 2;
E is independently selected from

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing

OG Complex Work Unit Drawing
wherein R2 is each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO2, 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, C1-50 alkyl, C2-50 alkenyl, C2-50 alkynyl, C2-50 alkoxy, CN, NO2, and OH;
Ar1 is a π-conjugated linker;
R1 is each independently selected from H, halo, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, CN, NO2, 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, C1-50 alkyl, C2-50 alkenyl, C2-50 alkynyl, C2-50 alkoxy, CN, NO2, and OH;
x is 1 or 2.