Granted Patent B1

US 8,158,744 · App. 13/037,466 · Granted Apr 17, 2012

Abstract

Claims (73)

1. A polymer of Formula (I):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl; p and q are the number of Ar 1 and Ar 2 units and are independently from 1 to about 25; wherein n is the number of repeating units and is from 2 to about 5,000; and

wherein each Ar 1 and Ar 2 unit is independently selected from the group consisting of:

and combinations thereof, wherein R′ is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 .

2. The polymer of claim 1 , wherein R 1 and R 2 are alkyl.

3. The polymer of claim 1 , having the structure of Formula (II):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, heteroaryl, substituted aryl, or substituted heteroaryl;

X 1 and X 2 are independently S, Se, O, or NR″, wherein each R″ can independently be hydrogen or alkyl;

each Z 1 and Z 2 is independently alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ;

M is a conjugated moiety;

a, c, and d are independently at least 1;

b is 0;

e and f are independently from 0 to 2; and

n is from 2 to about 5,000.

4. The polymer of claim 3 , wherein R 1 and R 2 are alkyl.

5. A semiconductor composition comprising a semiconductor polymer of Formula (I):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl; p and q are the number of Ar 1 and Ar 2 units and are independently from 1 to about 25; wherein n is the number of repeating units and is from 2 to about 5,000; and

wherein each Ar 1 and Ar 2 unit is independently selected from the group consisting of:

and combinations thereof, wherein R′ is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 .

6. The semiconductor composition of claim 5 , wherein R 1 and R 2 are the same.

7. An electronic device comprising a semiconducting layer, the semiconducting layer comprising a polymer of Formula (I):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl; p and q are the number of Ar 1 and Ar 2 units and are independently from 1 to about 25; wherein n is the number of repeating units and is from 2 to about 5,000; and

wherein each Ar 1 and Ar 2 unit is independently selected from the group consisting of:

and combinations thereof, wherein R′ is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 .

8. The electronic device of claim 7 , wherein R 1 and R 2 are the same.

9. The polymer of claim 3 , wherein the polymer has the structure of one of Formulas (2), (3), (7), (8), (11), or (12):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

10. The polymer of claim 3 , wherein the polymer has the structure of one of Formulas (4), (6), (14), or (17):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

11. The polymer of claim 3 , wherein the polymer has the structure of one of Formulas (9), (10), or (20):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

12. The polymer of claim 3 , wherein the polymer has the structure of one of Formulas (15), (16), or (19):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

13. The semiconductor composition of claim 5 , wherein the semiconductor polymer has the structure of one of Formulas (2), (3), (7), (8), (11), or (12):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

14. The semiconductor composition of claim 5 , wherein the semiconductor polymer has the structure of one of Formulas (4), (6), (14), or (17):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

15. The semiconductor composition of claim 5 , wherein the semiconductor polymer has the structure of one of Formulas (9), (10), or (20):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

16. The semiconductor composition of claim 5 , wherein the semiconductor polymer has the structure of one of Formulas (15), (16), or (19):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

17. The electronic device of claim 7 , wherein the polymer has the structure of one of Formulas (2), (3), (7), (8), (11), or (12):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

18. The electronic device of claim 7 , wherein the polymer has the structure of one of Formulas (4), (6), (14), or (17):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

19. The electronic device of claim 7 , wherein the polymer has the structure of one of Formulas (9), (10), or (20):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

20. The electronic device of claim 7 , wherein the polymer has the structure of one of Formulas (15), (16), or (19):

wherein R 1 and R 2 are independently hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl;

R 3 , R 4 , R 5 , and R 6 are independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, halogen, alkoxy, alkylthio, trialkylsilyl, —CN, or —NO 2 ; and

n is from 2 to about 5,000.

Assignments (10)