Asymmetric non-fullerene acceptor and organic photovoltaic device comprising the same

1. A compound of formula (1) or a stereoisomer thereof:

wherein R 10 -R 17 are each independently selected from the group consisting of hydrogen, deuterium, C 1 -C 6 alkyl, halogen, CO 2 R 114 , OR 115 , C 3 -C 6 cycloalkyl, C 2 -C 4 alkynyl, C 2 -C 4 -alkenyl, alkoxy, alkylthio, aryl, C 1 -C 6 heteroalkyl, C 3 -C 6 heterocycyl, C 3 -C 6 heteroaryl, amido, amino, cyano, and combinations thereof;

wherein R 11 and R 12 are the same; and R 15 and R 16 are the same;

R 18 , R 19 , R 110 , and R 111 are each independently an electron withdrawing group selected from the group consisting of: halogen, C(═O)R 116 , SO 3 R 117 , cyano, nitro, C(R 118 ) 3 , and combinations thereof;

R 114 -R 117 are each independently selected from the group consisting of hydrogen and C 1 -C 20 alkyl;

R 118 is a halogen selected from the group consisting of F, Cl, Br, and I;

R 112 , R 113 , and Y 1 -Y 4 are each independently selected from the group consisting of substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 10 aryl, and substituted or unsubstituted C 6 -C 10 heteroaryl;

X 1 -X 4 are each independently selected from the group consisting of S, O, NR, CRR′, SiRR′, and Se; and

R and R′ are each independently selected from the group consisting of hydrogen, C 1 -C 20 alkyl, C 6 -C 10 aryl, C 6 -C 10 heteroaryl, and combinations thereof;

wherein the compound of formula (1) is asymmetric.

2. The compound of claim 1 , wherein each of X 1 -X 4 are S.

3. The compound of claim 1 , wherein R 10 -R 13 , R 14 , and R 17 are each hydrogen; and

R 15 and R 16 are each independently a halogen selected from the group consisting of: F, Cl, Br, and I.

4. The compound of claim 3 , wherein R 15 and R 16 are each Cl.

5. The compound of claim 1 , wherein R 18 , R 19 , R 110 , and R 111 are each cyano.

6. The compound of claim 1 , wherein Y 1 -Y 4 are each independently selected from the group consisting of:

7. The compound of claim 1 , wherein Y 1 -Y 4 are each

8. The compound of claim 1 , wherein R 112 and R 113 are each independently selected from the group consisting of:

9. The compound of claim 1 , wherein R 112 and R 113 are each independently

10. The compound of claim 1 , wherein the compound of formula (1) is selected from the group consisting of:

11. An organic photovoltaic device comprising:

an anode,

a cathode, and

an active layer between the anode and the cathode, wherein the active layer comprises a compound of formula (1) or a stereoisomer thereof:

wherein R 10 -R 17 are each independently selected from the group consisting of hydrogen, deuterium, C 1 -C 6 alkyl, halogen, CO 2 R 114 , OR 115 , C 3 -C 6 cycloalkyl, C 2 -C 4 alkynyl, C 2 -C 4 alkenyl, alkoxy, alkylthio, aryl, C 1 -C 6 heteroalkyl, C 3 -C 6 heterocycyl, C 3 -C 6 heteroaryl, amido, amino, cyano, and combinations thereof;

wherein R 11 and R 12 are the same; and R 15 and R 16 are the same;

R 18 , R 19 , R 110 , and R 111 are each independently an electron withdrawing group selected from the group consisting of: halogen, C(═O)R 116 , SO 3 R 117 , cyano, nitro, C(R 118 ) 3 , and combinations thereof;

R 114 -R 117 are each independently selected from the group consisting of hydrogen and C 1 -C 20 alkyl;

R 118 is a halogen selected from the group consisting of F, Cl, Br, and I;

R 112 , R 113 , and Y 1 -Y 4 are each independently selected from the group consisting of substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 10 aryl, and substituted or unsubstituted C 6 -C 10 heteroaryl;

X 1 -X 4 are each independently selected from the group consisting of S, O, NR, CRR′, SiRR′, and Se; and

R and R′ are each independently selected from the group consisting of hydrogen, C 1 -C 20 alkyl, C 6 -C 10 aryl, C 6 -C 10 heteroaryl, and combinations thereof;

wherein the compound of formula (1) is asymmetric.

12. The organic photovoltaic device of claim 11 , wherein the active layer further comprises a polymer selected from the group consisting of:

and derivatives thereof;

wherein each R is independently a C 1 -C 20 alkyl; and n is the degree of polymerization.

13. The organic photovoltaic device of claim 12 , wherein the polymer comprises

wherein each R is independently a C 1 -C 20 alkyl; and n is the degree of polymerization.

14. The organic photovoltaic device of claim 13 , wherein each R represents 2-ethylhexyl.

15. The organic photovoltaic device of claim 11 , wherein in the acceptor represented by formula (1) is selected from the group consisting of:

16. The organic photovoltaic device of claim 11 , wherein the device has an open circuit voltage of between about 0.5 V and 1 V; or

wherein the device has a fill factor between about 55% and 75%.

17. The organic photovoltaic device of claim 11 , wherein the device has a short circuit current of between about 15 mA/cm 2 and 25 mA/cm 2 .

18. The organic photovoltaic device of claim 11 , wherein the device has an external quantum efficiency of between about 65% and 80%.

19. A formulation comprising a compound of formula (1) or a stereoisomer thereof:

wherein R 10 -R 17 are each independently selected from the group consisting of hydrogen, deuterium, C 1 -C 6 alkyl, halogen, CO 2 R 114 , OR 115 , C 3 -C 6 cycloalkyl, C 2 -C 4 alkynyl, C 2 -C 4 alkenyl, alkoxy, alkylthio, aryl, C 1 -C 6 heteroalkyl, C 3 -C 6 heterocycyl, C 3 -C 6 heteroaryl, amido, amino, cyano, and combinations thereof;

wherein R 11 and R 12 are the same; and R 15 and R 16 are the same;

R 18 , R 19 , R 110 , and R 111 are each independently an electron withdrawing group selected from the group consisting of: halogen, C(═O)R 116 , SO 3 R 117 , cyano, nitro, C(R 118 ) 3 , and combinations thereof;

R 114 -R 117 are each independently selected from the group consisting of hydrogen and C 1 -C 20 alkyl;

R 118 is a halogen selected from the group consisting of F, Cl, Br, and I;

R 112 , R 113 , and Y 1 -Y 4 are each independently selected from the group consisting of substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 6 -C 10 aryl, and substituted or unsubstituted C 6 -C 10 heteroaryl;

X 1 -X 4 are each independently selected from the group consisting of S, O, NR, CRR′, SiRR′, and Se; and

R and R′ are each independently selected from the group consisting of hydrogen, C 1 -C 20 alkyl, C 6 -C 10 aryl, C 6 -C 10 heteroaryl, and combinations thereof;

wherein the compound of formula (1) is asymmetric.