Organic photovoltaic devices comprising fullerenes and derivatives thereof
View Patent ↗Photovoltaic cells comprising an active layer comprising, as p-type material, conjugated polymers such as polythiophene and regioregular polythiophene, and as n-type material at least one fullerene derivative. The fullerene derivative can be C60, C70, or C84. The fullerene also can be functionalized with indene groups. Improved efficiency can be achieved.
1. A composition comprising at least one n-type material, wherein the n-type material comprises a fullerene derivative represented by:
F*-(R) n
and solvates, salts, and mixtures thereof,
wherein n is 1 or 2,
F* comprises a fullerene having a surface which comprises six-membered and five-membered rings; and
R is optionally substituted o-quinodimethane which is covalently bonded to the fullerene by two bonds; and
wherein the composition further comprises at least one p-type material mixed with said n-type material, wherein said p-type material is poly(3-hexylthiophene).
2. The composition of claim 1 , wherein R is unsubstituted o-quinodimethane.
3. The composition of claim 1 , wherein R is substituted with at least one substituent selected from the group consisting of hydroxy, acyl, acylamino, acyloxy, alkyl, substituted alkyl, alkoxy, substituted alkoxy, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, amino, substituted amino, aminoacyl, aryl, substituted aryl, aryloxy, substituted aryloxy, cycloalkoxy, substituted cycloalkoxy, carboxyl, carboxyl esters, cyano, thiol, thioalkyl, substituted thioalkyl, thioaryl, substituted thioaryl, thioheteroaryl, substituted thioheteroaryl, thiocycloalkyl, substituted thiocycloalkyl, thioheterocyclic, substituted thioheterocyclic, cycloalkyl, substituted cycloalkyl, halo, nitro, heteroaryl, substituted heteroaryl, heterocyclic, substituted heterocyclic, heteroaryloxy, substituted heteroaryloxy, heterocyclyloxy, or substituted heterocyclyloxy, and combination thereof.
4. The composition of claim 1 , wherein R is covalently bonded to the fullerene by [4+2]cycloaddition.
5. The composition of claim 1 , wherein R is covalently bonded to at least one fullerene [6,6] bonding site by two carbon-carbon bonds.
6. The composition of claim 1 , wherein the fullerene comprises a C60, C70, or C84 fullerene, or a combination thereof.
7. The composition of claim 1 , wherein the fullerene derivative comprises at least one derivative group bonded to the fullerene besides R.
8. The composition of claim 1 , wherein the composition further comprises at least one solvent.
9. The composition of claim 1 , wherein n is 2.
10. The composition of claim 1 , wherein n is 1.
11. A photovoltaic device comprising at least one anode, at least one cathode, and at least one active layer, wherein the active layer comprises the composition of claim 1 .
12. The photovoltaic device of claim 11 , wherein the power conversion efficiency of the device is at least 4%.
13. The photovoltaic device of claim 11 , wherein the device demonstrates an increase of efficiency of at least 15% compared to a substantially analogous device comprising an active layer of P3HT-PCBM.
14. The photovoltaic device of claim 11 , further comprising at least one hole injection layer or hole transport layer which comprises polythiophene.