Disordered organic electronic materials based on non-benzenoid 1,6-methano[10]annulene rings
Conjugated polymers and small molecules including the nonplanar aromatic 1,6-methano[10]annulene ring structure along with aromatic subunits, such as diketopyrrolopyrrole, and 2,1,3-benzothiadiazole, substituted with alkyl chains in a “Tail In,” “Tail Out,” or “No Tail” regiochemistry are disclosed.
1. A compound of Formula (I) or Formula (II):
wherein:
n is an integer selected from the group consisting of 1 to 150; and
R 1 , R 2 , and, R 3 are each independently selected from the group consisting of H and C 6 -C 20 linear or branched alkyl.
2. The compound of claim 1 , wherein R 3 is C 8 H 17 and the compound of Formula (I) is selected from the group consisting of:
3. The compound of claim 1 , wherein the compound of Formula (II) is selected from the group consisting of:
4. The compound of claim 1 , wherein n is selected from the group consisting of 2, 3, 4, and 5.
5. A monomer of a compound of Formula (II), wherein the monomer is a compound of Formula (III):
6. The monomer of claim 5 , wherein the compound of Formula (III) is selected from the group consisting of:
7. A film comprising a compound of Formula (I) or Formula (II):
wherein:
n is an integer selected from the group consisting of 1 to 150; and
R 1 , R 2 , and, R 3 are each independently selected from the group consisting of H and C 6 -C 20 linear or branched alkyl.
8. The film of claim 7 , further comprising a blend of a compound of Formula (I) or Formula (II) and one or more of an electron donating material and an electron accepting material.
9. The film of claim 8 , wherein the electron accepting material comprises a fullerene.
10. The film of claim 9 , wherein the fullerene comprises [6,6]-phenyl-C 61 -butyric acid methyl ester (PCBM).
11. The film of claim 8 , wherein the electron donating material is selected from the group consisting of poly(3-hexyl thiophene) (P3HT) and 2-methoxy-5-(2′-ethylhexyloxy)-p-phenylene vinylene (MEH-PPV).
12. A device comprising the film of claim 7 .
13. The device of claim 12 , wherein the device comprises a bulk heterojunction organic photovoltaic (BHJ-OPV) device.
14. The device of claim 12 , wherein the device comprises a layered device in which at least one of a p-channel layer and an n-channel layer comprises a compound of Formula (I) or Formula (II).
15. A device comprising a compound of Formula (I) or Formula (II):
wherein:
n is an integer selected from the group consisting of 1 to 150; and
R 1 , R 2 , and, R 3 are each independently selected from the group consisting of H and C 6 -C 20 linear or branched alkyl.
16. The device of claim 15 , wherein the device comprises an organic semiconductor.
17. The device of claim 15 , wherein the device is selected from the group consisting of a thermoelectric device and an organic photovoltaic device.
18. The device of claim 15 , wherein the device comprises a field-effect transistor.
19. The device of claim 15 , wherein the field-effect transistor comprises a p-type field-effect transistor.
20. The device of claim 18 , wherein the field-effect transistor comprises a device selected from the group consisting of a display element, an electronic tag, an electromagnetic sensor, and a pressure sensor.