Semiconducting polymers
View Patent ↗A semiconducting polymer of Formula (I): wherein X is independently selected from S, Se, O, and NR, wherein R is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, and —CN; Ar is independently a conjugated divalent moiety; a is an integer from 1 to about 10; and n is an integer from 2 to about 5,000. The resulting semiconducting polymer is suitable for use in organic thin film transistors.
1. A semiconducting polymer of Formula (I):
wherein X is independently selected from S, Se, O, and NR, wherein R is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, and —CN;
a is an integer from 1 to about 10;
n is an integer from 2 to about 5,000; and
each Ar is a conjugated divalent moiety selected from:
and combinations thereof, wherein R′ is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, or —CN; and the divalent moiety may be substituted peripherally with alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, or —NO 2 .
2. The semiconducting polymer of claim 1 , wherein X is independently selected from S and O.
3. The semiconducting polymer of claim 1 , wherein each X is O.
4. The semiconducting polymer of claim 1 , wherein the semiconducting polymer has a LUMO of 3.5 eV or less.
5. The semiconducting polymer of claim 1 , wherein the semiconducting polymer has a LUMO of 4.0 eV or less.
6. The semiconducting polymer of claim 1 , wherein the semiconducting polymer has a LUMO of 4.5 eV or less.
7. The semiconducting polymer of claim 1 , wherein the semiconducting polymer is an n-type semiconductor.
8. The semiconducting polymer of claim 1 , wherein the semiconducting polymer is both an n-type and a p-type semiconductor.
9. The semiconducting polymer of claim 1 , wherein the semiconducting polymer has a weight average molecular weight of from about 1,000 to about 1,000,000.
10. The semiconducting polymer of claim 1 , wherein the semiconducting polymer has a weight average molecular weight of from 5,000 to about 100,000.
11. A semiconducting polymer of Formula (I):
wherein X is independently selected from S, Se, O, and NR, wherein R is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, and —CN;
each Ar moiety is independently selected from:
a is an integer from 1 to about 10; and
n is an integer from 2 to about 5,000.
12. The semiconducting polymer of claim 11 , wherein X is independently selected from S and O.
13. The semiconducting polymer of claim 11 , wherein the semiconducting polymer has a LUMO of 4.5 eV or less.
14. A semiconducting polymer of Formula (1):
wherein R 1 is an alkyl group having 1 to about 20 carbon atoms, or an aryl or a heteroaryl group having from about 5 to about 20 carbon atoms.
15. The semiconducting polymer of claim 14 , wherein the semiconducting polymer is Formula (1):
wherein R 1 is alkyl having about 4 to about 20 carbon atoms.
16. A semiconducting polymer, wherein the semiconducting polymer is selected from the group consisting of formulas (1), (3), (4), (6) through (9), (11) through (17), (19) through (25), and (27) through (32):
wherein R, R′, R 1 , and R 2 are independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, —CN, or mixtures thereof.