Conjugated polymers and their use in optoelectronic devices
View Patent ↗Disclosed are certain polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic, and/or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors, and field effect transistors. The disclosed compounds can provide improved device performance, for example, as measured by power conversion efficiency, fill factor, open circuit voltage, field-effect mobility, on/off current ratios, and/or air stability when used in photovoltaic cells or transistors. The disclosed compounds can have good solubility in common solvents enabling device fabrication via solution processes.
1. An electronic, optical or optoelectronic device comprising:
a first electrode,
a second electrode, and
a semiconductor component disposed between the first electrode and the second electrode, the semiconductor component comprising a random copolymer having the formula:
wherein
M is an optionally substituted 2,1,3-benzothiadiazole-4,7-diyl group;
each of R 1 and R 2 is a branched C 6-20 alkyl group, a branched C 6-20 alkoxy group, or an organic group comprising a cyclic moiety;
R 7 is a linear C 6-20 alkyl group; and
x and y are real numbers representing mole fractions, wherein 0.1≦x≦0.9, 0.1≦y≦0.9, and the sum of x and y is about 1.
2. The device of claim 1 , wherein the random copolymer has the formula:
wherein M, R 1 , R 2 , R 7 , x and y are as defined in claim 1 .
3. The device of claim 1 , wherein M is
wherein R 5 and R 6 independently are H or -L-R, wherein L, at each occurrence, independently is selected from the group consisting of O, S, and a covalent bond; and R, at each occurrence, independently is a C 1-40 alkyl group.
4. The device of claim 1 , wherein
wherein p is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
5. The device of claim 1 , wherein 0.2≦x≦0.8, 0.2≦y≦0.8, and the sum of x and y is about 1.
6. The device of claim 1 , wherein 0.3≦x≦0.7, 0.3≦y≦0.7, and the sum of x and y is about 1.
7. The device of claim 1 , wherein the random copolymer has a degree of polymerization (n) in the range from 10 to about 10,000.
8. The device of claim 1 configured as an organic photovoltaic device comprising an anode, a cathode, and in between the anode and the cathode the semiconductor component according to claim 1 .
9. The device of claim 8 , wherein the organic photovoltaic device is a bulk heterojunction photovoltaic device.
10. The device of claim 9 , wherein the semiconductor component is photoactive and comprises a blend material, wherein the copolymer in the blend material functions as an electron-donor and the blend material further comprises an electron-acceptor compound.
11. The device of claim 10 , wherein the electron-acceptor compound is a fullerene compound.
12. The device of claim 11 , wherein the fullerene compound is [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM).
13. The device of claim 11 , wherein the fullerene compound is [6,6]-phenyl-C 71 -butyric acid methyl ester (C 70 PCBM).
14. The device of claim 8 , wherein the power conversion efficiency is at least about 4%.
15. The device of claim 8 , wherein the power conversion efficiency is at least about 5%.
16. The device of claim 8 , wherein the power conversion efficiency is at least about 6%.
17. The device of claim 1 , wherein each of R 1 and R 2 is a branched C 6-20 alkyl group.
18. The device of claim 1 , wherein each of R 1 and R 2 is a branched C 6-20 alkoxy group.
19. The device of claim 1 , wherein each of R 1 and R 2 is an organic group comprising a cyclic moiety.
20. The device of claim 1 , wherein each of R 1 and R 2 is selected from a -L′-C 3-10 cycloalkyl group, a -L′-C 6-14 aryl group, a -L′-C 6-14 haloaryl group, a -L′-3-12 membered cycloheteroalkyl group, and a -L′-5-14 membered heteroaryl group, wherein L′ is selected from a divalent C 1-20 alkyl group, a divalent C 1-20 haloalkyl group, and a covalent bond, and each of the C 3-10 cycloalkyl group, the C 6-14 aryl group, the C 6-14 haloaryl group, the 3-12 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted.