Key materials for organic photovoltaics reliability

1. An acceptor for an organic photovoltaic cell, the acceptor comprising one of the Formulae (I)-(III):

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 A 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 acceptor of claim 1 , wherein each A 1 , each Ar 3 or each A 1 and Ar 3 is:

3. The acceptor of claim 1 , wherein A or B is:

4. The acceptor of claim 1 , wherein Ar 4 is:

5. The acceptor of claim 1 , wherein A or B is:

6. The acceptor of claim 1 , wherein at least one of M 1 -M 4 is chloride.

7. The acceptor of claim 1 , wherein each R is selected from the group consisting of:

8. The acceptor of claim 1 , wherein each R is 2-ethylhexyl.

9. The acceptor of claim 1 , wherein each Y is:

10. The acceptor of claim 1 , wherein the acceptor 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 acceptor of claim 10 , wherein the acceptor 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 an acceptor according to claim 1 .

13. 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 electron transporting layer, an anode buffer, and a cathode buffer.

14. The organic photovoltaic device of claim 13 , 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 M1-M4 is a halogen; and

each R is independently a C1-C20 hydrocarbon or an aromatic hydrocarbon.

15. The organic photovoltaic device of claim 14 , wherein each R is independently selected from the group consisting of

16. The organic photovoltaic device of claim 14 , wherein the cathode buffer comprises a material selected from the group consisting of:

wherein 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.

17. The organic photovoltaic device of claim 14 , wherein the anode buffer comprises a material selected from the group consisting of:

18. An organic photovoltaic device comprising:

an anode;

a cathode;

at least one selected from an anode buffer and a cathode buffer; and

an organic layer, disposed between the anode and the cathode, comprising an acceptor comprising 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 X A is individually selected from the group consisting of CRR, O, S, Se and NR;

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;

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.

19. A formulation comprising the acceptor of claim 1 .

20. A composition comprising an acceptor of 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 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;

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 -MD 4 is a halogen; and

each R is independently a C 1 -C 20 hydrocarbon or an aromatic hydrocarbon.