End-group-directed self-assembly of organic compounds useful for photovoltaic applications
The present invention provides for an organic compound comprising electron deficient unit covalently linked to two or more electron rich units. The present invention also provides for a device comprising the organic compound, such as a light-emitting diode, thin-film transistor, chemical biosensor, non-emissive electrochromic, memory device, photovoltaic cells, or the like.
1. An organic compound comprising the following structure: α-γ n -X-γ n -α; wherein X consists of
wherein R1 and R2 each independently comprise a straight or branched alkyl chain; each γ is independently a thiophene, furan, or pyrrole; each n is independently an integer from 1 to 20; and, each α comprises a multi-ring aromatic structure which are each capable of π-stacking with the α of a second organic compound, wherein the organic compound and second organic compound can have identical or different chemical structures; wherein (a) the γ n at both ends of X comprise of one or more furans, (b) α has at least one line of symmetry, or at least a 2-fold rotational symmetry, or (c) α comprises an acenaphthene, acenaphthylene, anthanthrene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzopyrene, chrysene, coronene, corannulene, dibenz(a,h)anthracene, fluoranthene, hexabenzocoronene, indeno(1,2,3-cd)pyrene, naphthalene, ovalene, pentacene, pentaphene, perylene, phenanthrene, pyrene, tetracene, tetraphene, triphenylene,
2. The organic compound of claim 1 , wherein (a) α has at least one line of symmetry, or at least a 2-fold rotational symmetry, or (b) α comprises an acenaphthene, acenaphthylene, anthanthrene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzopyrene, chrysene, coronene, corannulene, dibenz(a,h)anthracene, fluoranthene, hexabenzocoronene, indeno(1,2,3-cd)pyrene, naphthalene, ovalene, pentacene, pentaphene, perylene, phenanthrene, pyrene, tetracene, tetraphene, triphenylene,
and each γ is independently
wherein Z is —S—, —O—, or —NH—.
3. The organic compound of claim 1 , wherein (a) α has at least one line of symmetry, or at least a 2-fold rotational symmetry, or (b) α comprises an acenaphthene, acenaphthylene, anthanthrene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzopyrene, chrysene, coronene, corannulene, dibenz(a,h)anthracene, fluoranthene, hexabenzocoronene, indeno(1,2,3-cd)pyrene, naphthalene, ovalene, pentacene, pentaphene, perylene, phenanthrene, pyrene, tetracene, tetraphene, triphenylene,
and γ n -X-γ n has one of the following structure:
4. The organic compound of claim 1 , wherein the γ n at both ends of X are identical.
5. The organic compound of claim 1 , wherein the γ n at both ends of X comprise of one or more thiophenes.
6. The organic compound of claim 5 , wherein (a) α has at least one line of symmetry, or at least a 2-fold rotational symmetry, or (b) α comprises an acenaphthene, acenaphthylene, anthanthrene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzopyrene, chrysene, coronene, corannulene, dibenz(a,h)anthracene, fluoranthene, hexabenzocoronene, indeno(1,2,3-cd)pyrene, naphthalene, ovalene, pentacene, pentaphene, perylene, phenanthrene, pyrene, tetracene, tetraphene, triphenylene,
and the γ n at both ends of X consist of only thiophene(s).
7. The organic compound of claim 1 , wherein the γ n at both ends of X comprise of one or more furans.
8. The organic compound of claim 7 , wherein the γ n at both ends of X consist of only furan(s).
9. The organic compound of claim 1 , wherein R1 and R2 independently have at least about 4 carbon atoms.
10. The organic compound of claim 1 , wherein R1 and R2 independently have from about 4 to 40 carbon atoms.
11. The organic compound of claim 1 , wherein R1 and R2 independently comprise at least 1 or 2 branch chains comprising from about 1 to 16 carbon atoms.
12. The organic compound of claim 1 , wherein R1 and R2 independently are 2-ethylhexyl, 2-butyloctyl, 2-hexylddecyl, or 2-octyldodecyl.
13. The organic compound of claim 1 , wherein R1 and R2 are identical.
14. The organic compound of claim 1 , wherein α has at least one line of symmetry, or at least a 2-fold rotational symmetry.
15. The organic compound of claim 1 , wherein the γ n at both ends of X comprise of one or more furans and α comprises from about one to eight benzenes.
16. The organic compound of claim 15 , wherein α comprises from about one to four benzenes.
17. The organic compound of claim 1 , α comprises one or more heteroatoms.
18. The organic compound of claim 1 , wherein α comprises a polycyclic aromatic or partially aromatic hydrocarbon (PAH).
19. The organic compound of claim 1 , wherein α comprises an acenaphthene, acenaphthylene, anthanthrene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzopyrene, chrysene, coronene, corannulene, dibenz(a,h)anthracene, fluoranthene, hexabenzocoronene, indeno(1,2,3-cd)pyrene, naphthalene, ovalene, pentacene, pentaphene, perylene, phenanthrene, pyrene, tetracene, tetraphene, and triphenylene.
20. The organic compound of claim 1 , wherein α comprises a
21. A plurality of the organic compound of claim 1 , wherein each organic compound is π-stacked with at least one other organic compound.
22. A device comprising the organic compound of claim 1 .
23. The device of claim 22 , wherein the device is a light-emitting diode, thin-film transistor, chemical biosensor, non-emissive electrochromic, memory device, or photovoltaic cell.
24. The device of claim 23 , wherein the device comprises (a) the organic compound as a p-type component, and (b) a suitable n-type component.
25. A photovoltaic device comprising a photoactive layer comprising the organic compound of claim 1 disposed between a first electrode and a second electrode.
26. The photovoltaic device of claim 25 , wherein the first electrode is ITO.
27. The photovoltaic device of claim 25 , wherein the second electrode is LiF/Al.
28. The photovoltaic device of claim 25 , wherein the photoactive layer, the first electrode, and the second electrode are thin films.
29. The photovoltaic device of claim 28 , wherein the device further comprises a substrate, wherein the thin films are disposed on the substrate.
30. The photovoltaic device of claim 29 , wherein the substrate comprises glass.
31. The organic compound of claim 1 , wherein the organic compound is:
wherein R is 2-octyldodecyl, 2-hexyldecyl, 2-butyloctyl, or 2-ethylhexyl.
32. An organic compound comprising the following structure: α-γ n -X-γ n -α; wherein X comprises a multi-ring organic structure comprising at least one benzene, imide, pyrrole, furan, or thiophene; each γ is independently a thiophene, furan, or pyrrole; each n is independently an integer from 1 to 20; and, each α comprises a multi-ring aromatic structure which are each capable of π-stacking with the α of a second organic compound, wherein the organic compound and second organic compound can have identical or different chemical structures; wherein (a) the γ n at both ends of X comprise of one or more furans, or (b) α comprises an acenaphthene, acenaphthylene, anthanthrene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzopyrene, chrysene, coronene, corannulene, dibenz(a,h)anthracene, fluoranthene, hexabenzocoronene, indeno(1,2,3-cd)pyrene, naphthalene, ovalene, pentacene, pentaphene, perylene, phenanthrene, pyrene, tetracene, tetraphene, triphenylene,
33. The organic compound of claim 32 , wherein the γ n at both ends of X comprise of one or more furans.
34. The organic compound of claim 33 , wherein the γ n at both ends of X consist of only furan(s).
35. The organic compound of claim 32 , wherein α comprises from about one to eight benzenes.
36. The organic compound of claim 35 , wherein α comprises from about one to four benzenes.
37. The organic compound of claim 32 , wherein α comprises a polycyclic aromatic or partially aromatic hydrocarbon (PAH).
38. The organic compound of claim 32 , wherein α comprises an acenaphthene, acenaphthylene, anthanthrene, anthracene, benz[a]anthracene, benzo[a]pyrene, benzo[e]pyrene, benzo[b]fluoranthene, benzo[ghi]perylene, benzo[j]fluoranthene, benzo[k]fluoranthene, benzopyrene, chrysene, coronene, corannulene, dibenz(a,h)anthracene, fluoranthene, hexabenzocoronene, indeno(1,2,3-cd)pyrene, naphthalene, ovalene, pentacene, pentaphene, perylene, phenanthrene, pyrene, tetracene, tetraphene, and triphenylene.
39. The organic compound of claim 32 , wherein α comprises a