Key materials for organic photovoltaics reliability
View Patent ↗Organic photovoltaic cells (OPVs) and their compositions are described herein. one or more embodiments, the acceptor with an active layer of an OPV includes is a non-fullerene acceptor. Such non-fullerene acceptors may provide improved OPV performance characteristics such as improved power conversion efficiency, open circuit voltage, fill factor, short circuit current, and/or external quantum efficiency.
1. A compound having a structure represented by one of the Formulae (I)-(VI):
wherein:
A and B are individually selected from the group consisting of:
each Ar 1 is individually selected from the group consisting of:
each Ar 2 is individually selected from the group consisting of:
each Ar 3 is individually selected from the group consisting of:
each Ar 4 is individually selected from the group consisting of:
M 1 -M 4 are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, astatine, and a cyano group, wherein at least one of M 1 -M 4 is a halogen;
each X is individually selected from the group consisting of S, NR, Se, Te, and O;
each R is individually a C 1 -C 20 hydrocarbon or an aromatic hydrocarbon;
each Y is individually selected from the group consisting of:
each m is an integer from 0 to 10; and
each n is an integer from 0 to 10.
2. The compound of claim 1 , wherein each Ar 1 , each Ar 3 or each Ar 1 and Ar 3 is:
3. The compound of claim 1 , wherein A or B is:
4. The compound of claim 1 , wherein Ar 4 is:
5. The compound of claim 1 , wherein A or B is:
6. The compound of claim 1 , wherein at least one of M 1 -M 4 is chloride.
7. The compound of claim 1 , wherein each R is selected from the group consisting of:
8. The compound of claim 1 , wherein each R is 2-ethylhexyl.
9. The compound of claim 1 , wherein each Y is:
10. The compound of claim 1 , wherein the compound has one of formulae (Ia), (Ib), (IIIa) and (IIIb):
wherein:
each X is independently selected from the group consisting of S, NR, Se, Te, and O;
each R is independently selected from a C 1 -C 20 hydrocarbon, an aromatic hydrocarbon wherein the hydrocarbon, and aromatic hydrocarbon are each optionally substituted;
each R′ is independently a halogen; and
each p is independently an integer from 0-4.
11. The compound of claim 1 , wherein the compound is selected from the group consisting of:
12. An organic photovoltaic device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound having a structure represented by one of the Formulae (I)-(VI):
wherein:
A and B are individually selected from the group consisting of:
each Ar 1 is individually selected from the group consisting of:
each Ar 2 is individually selected from the group consisting of:
each Ar 3 is individually selected from the group consisting of:
each Ar 4 is individually selected from the group consisting of:
M 1 -M 4 are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, astatine, and a cyano group, wherein at least one of M 1 -M 4 is a halogen;
each X is individually selected from the group consisting of S, NR, Se, Te, and O;
each R is individually a Ci-Cao hydrocarbon or an aromatic hydrocarbon;
each Y is individually selected from the group consisting of:
each m is an integer from 0 to 10; and
each n is an integer from 0 to 10.
13. The organic photovoltaic device of claim 12 , wherein each R is independently selected from the group consisting of
14. The organic photovoltaic device of claim 12 , wherein the device further comprises at least one selected from the group consisting of hole transporting layer, an electrode transporting layer, an anode buffer, and a cathode buffer.
15. The organic photovoltaic device of claim 14 , wherein the cathode buffer comprises a material selected from the group consisting of:
wherein each X is individually selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium, and nitrogen;
each Y is individually selected from the group consisting of:
each Ar 1 is independently selected from the group consisting of:
M 1 -M 4 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, astatine, and a cyano group, wherein at least one of M 1 -M 4 is a halogen; and
each R is independently a C 1 -C 20 hydrocarbon or an aromatic hydrocarbon.
16. The organic photovoltaic device of claim 14 , wherein the cathode buffer comprises a material selected from the group consisting of:
wherein each AO is independently selected from the group consisting of:
M 1 -M 4 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, astatine, and a cyano group, wherein at least one of M 1 -M 4 is a halogen; and
each R is independently a C 1 -C 20 hydrocarbon or an aromatic hydrocarbon.
17. The organic photovoltaic device of claim 14 , wherein the anode buffer comprises a material selected from the group consisting of:
18. A formulation comprising the compound of claim 1 .
19. A composition comprising a compound represented by one of formulae (I)-(VI) and at least one of a cathode buffer and an anode buffer:
wherein:
A and B are individually selected from the group consisting of:
each Ar 1 is individually selected from the group consisting of:
each Ar 2 is individually selected from the group consisting of:
each Ar 3 is individually selected from the group consisting of:
each Ar 4 is individually selected from the group consisting of:
M 1 -M 4 are individually selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, astatine, and a cyano group, wherein at least one of M 1 -M 4 is a halogen;
each X is individually selected from the group consisting of S, NR, Se, Te, and O;
each X A is individually selected from the group consisting of CRR, O, S, Se and NR;
each R is individually a Ci-Cao hydrocarbon or an aromatic hydrocarbon;
each Y is individually selected from the group consisting of:
each m is an integer from 0 to 10; and
each n is an integer from 0 to 10;
the anode buffer comprises a material selected from the group consisting of:
and
the cathode buffer comprises a material selected from the group consisting of:
wherein each X is individually selected from the group consisting of oxygen, carbon, hydrogen, sulfur, selenium, and nitrogen;
each Y is individually selected from the group consisting of:
each Ar 1 is independently selected from the group consisting of:
M 1 -M 4 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, astatine, and a cyano group, wherein at least one of M 1 -M 4 is a halogen; and
each R is independently a C 1 -C 20 hydrocarbon or an aromatic hydrocarbon; or
wherein the cathode buffer comprises a material selected from the group consisting of:
each Ar 1 is independently selected from the group consisting of:
M 1 -M 4 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, astatine, and a cyano group, wherein at least one of M 1 -M 4 is a halogen; and
each R is independently a C 1 -C 20 hydrocarbon or an aromatic hydrocarbon.