Organic thin-film transistors
A thin-film transistor comprises a semiconducting layer comprising a semiconducting material selected from Formula (I) or (II): wherein X, R 1 , R 2 , R 3 , R 4 , R 5 a, b, and n are as described herein. Semiconducting compositions of Formula (I) or (II) are also described.
1. A thin-film transistor comprising a semiconducting layer, wherein the semiconducting layer comprises a semiconducting material selected from Formula (I) or (II):
wherein X is independently selected from S and Se in Formula (I) and X is independently selected from S, Se, and O in Formula (II);
R 1 , R 2 , R 3 , R 4 , and R 5 are independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, and —NO 2 ;
Ar and Ar′ are independently a conjugated divalent moiety;
a and b are integers of from 0 to 10; and
n is an integer and is at least 2.
2. The transistor of claim 1 , wherein R 2 , R 3 , R 4 , and R 5 are hydrogen.
3. The transistor of claim 1 , wherein at least one of R 2 , R 3 , R 4 , and R 5 is alkyl.
4. The transistor of claim 1 , wherein R 1 of Formula (I) is an ethynylsilane.
5. The transistor of claim 4 , wherein the ethynylsilane is substituted with three alkyl groups.
6. The transistor of claim 1 , wherein Ar and Ar′ independently comprise a moiety selected from
and combinations thereof, wherein R′ is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, and —NO 2 .
7. The transistor of claim 6 , wherein Ar and Ar′ are both
and a and b are each from 1 to 5.
8. The transistor of claim 6 , wherein Ar and A′ are both
and a and b are each from 1 to 5.
9. The transistor of claim 1 , wherein each X is sulfur.
10. The transistor of claim 1 , wherein the semiconducting material has a weight average molecular weight of from about 2,000 to about 200,000.
11. A semiconducting composition comprising a compound of Formula (I) or (II):
wherein X is independently selected from S and Se in Formula (I) and X is independently selected from S, Se, and O in Formula (II);
R 1 , R 2 , R 3 , R 4 , and R 5 are independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, and —NO 2 ;
Ar and Ar′ are independently a conjugated divalent moiety;
a and b are integers of from 0 to 10; and
n is an integer and is at least 2.
12. The composition of claim 11 , wherein R 2 , R 3 , R 4 , and R 5 are hydrogen.
13. The composition of claim 11 , wherein at least one of R 2 , R 3 , R 4 , and R 5 is alkyl.
14. The composition of claim 11 , wherein R 1 of Formula (I) is an ethynylsilane.
15. The composition of claim 14 , wherein the ethynylsilane is substituted with three alkyl groups.
16. The composition of claim 11 , wherein Ar and Ar′ independently comprise a moiety selected from
and combinations thereof, wherein R′ is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, and —NO 2 .
17. The composition of claim 16 , wherein Ar and Ar′ are both
and a and b are each from 1 to 5.
18. The composition of claim 16 , wherein Ar and Ar′ are both
and a and b are each from 1 to 5.
19. The composition of claim 11 , wherein each X is sulfur.
20. The composition of claim 11 , wherein the semiconducting material has a weight average molecular weight of from about 2,000 to about 200,000.
21. A semiconducting composition comprising compound of Formula (I) or (II):
wherein X is sulfur;
R 1 , R 2 , R 3 , R 4 , and R 5 are independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, and —NO 2 ;
Ar and Ar′ are
a and b are each an integer from 1 to 5; and
n is an integer and is at least 2.