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 semiconducting material selected from Formula (I) or Formula (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 is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, —NO 2 , and ethynylsilane;
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 1 to about 5; and
n is an integer and is at least 2.
2. The semiconducting material of claim 1 , wherein R 2 , R 3 , R 4 , and R 5 are hydrogen.
3. The semiconducting material of claim 1 , wherein at least one of R 2 , R 3 , R 4 , and R 5 is alkyl.
4. The semiconducting material of claim 1 , wherein the ethynylsilane is substituted with three alkyl groups.
5. The semiconducting material 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 .
6. The semiconducting material of claim 5 , wherein Ar and Ar′ are both
and
wherein a and b are each from 1 to about 5.
7. The semiconducting material of claim 5 , wherein Ar and Ar′ are both
wherein a and b are each from 1 to about 5.
8. The semiconducting material of claim 1 , wherein each X is sulfur.
9. The semiconducting material of claim 1 , having a weight average molecular weight of from about 2,000 to about 200,000.
10. A semiconducting material of Formula (I):
wherein X is independently selected from S and Se;
R 1 is independently selected from hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, halogen, —CN, —NO 2 , and ethynylsilane;
R 2 , R 3 , and R 4 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 1 to about 10; and
n is an integer and is at least 2.
11. The semiconducting material of claim 10 , 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 .
12. The semiconducting material of claim 11 , wherein Ar and Ar′ are both
and
wherein a and b are each from 1 to about 5.
13. The semiconducting material of claim 11 , wherein Ar and Ar′ are both
wherein a and b are each from 1 to about 5.
14. The semiconducting material of claim 10 , wherein each X is sulfur.