Tetrahydrotetraazapentacenes in thin-film transistors
Compounds of Formula (I) are disclosed: wherein R 1 -R 14 , x, y, and z are as defined herein. The compounds are useful as semiconducting materials for electronic devices such as thin-film transistors.
1. A compound of Formula (I):
wherein each R 1 , R 2 , R 3 , R 4 , R 6 , R 8 , R 9 , R 10 , R 11 , and R 13 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, aryl, substituted aryl, and halogen; each R 5 , R 7 , R 12 , and R 14 is independently selected from hydrogen, alkyl, substituted alkyl, aryl, and substituted aryl; x is an integer from 1 to 3; y is an integer from 1 to 4; and z is an integer from 1 to 3.
2. The compound of claim 1 , wherein x, y, and z are 1 and R 1 -R 14 are hydrogen.
3. The compound of claim 1 , wherein R 2 and R 3 are identical to each other, R 9 and R 10 are identical to each other, and R 2 is different from R 9 .
4. The compound of claim 1 , wherein R 2 , R 3 , R 9 , and R 10 are not hydrogen.
5. The compound of claim 4 , wherein R 2 , R 3 , R 9 , and R 10 are the same.
6. The compound of claim 1 , wherein the compound is of Formula (II):
wherein R 2 , R 3 , R 9 , and R 10 , are independently selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, aryl, substituted aryl, and halogen; wherein R 5 , R 7 , R 12 , and R 14 are independently selected from hydrogen, alkyl, substituted alkyl, aryl, and substituted aryl; and wherein at least one of R 2 , R 3 , R 5 , R 7 , R 9 , R 10 , R 12 , or R 14 is not hydrogen.
7. The compound of claim 1 , wherein the compound is of Formula (III):
wherein R 2 , R 3 , R 9 , and R 10 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, aryl, substituted aryl, and halogen; and wherein at least one of R 2 , R 3 , R 9 , or R 10 is not hydrogen.
8. The compound of claim 7 , wherein R 2 and R 3 are identical to each other, R 9 and R 10 are identical to each other, and R 2 is different from R 9 .
9. The compound of claim 1 , wherein the compound is of Formula (IV):
wherein R 5 , R 7 , R 12 , and R 14 are independently selected from alkyl, substituted alkyl, aryl, and substituted aryl.
10. The compound of claim 9 , wherein R 5 , R 7 , R 12 , and R 14 are the same.
11. The compound of claim 9 , wherein R 5 and R 14 are identical to each other; R 7 and R 12 are identical to each other; and R 5 is different from R 7 .
12. A thin film transistor, comprising:
a substrate; and
a semiconducting layer on the substrate, the semiconducting layer comprising a tetrahydrotetraazaacene of Formula (I):
wherein each R 1 , R 2 , R 3 , R 4 , R 6 , R 8 , R 9 , R 10 , R 11 , and R 13 is independently selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, aryl, substituted aryl, and halogen; each R 5 , R 7 , R 12 , and R 14 is independently selected from hydrogen, alkyl, substituted alkyl, aryl, and substituted aryl; x is an integer from 1 to 3; y is an integer from 1 to 4; and z is an integer from 1 to 3.
13. The transistor of claim 12 , wherein x, y, and z are 1 and R 1 -R 14 are hydrogen.
14. The transistor of claim 12 , wherein x and z are equal to each other.
15. The transistor of claim 12 , wherein y is from 2 to 4.
16. The transistor of claim 12 , wherein R 5 , R 7 , R 12 , and R 14 are the same.
17. The transistor of claim 12 , wherein R 2 and R 3 are identical to each other, R 9 and R 10 are identical to each other, and R 2 is different from R 9 .
18. The transistor of claim 12 , wherein the tetrahydrotetraazaacene is of Formula (II):
wherein R 2 , R 3 , R 9 , and R 10 , are independently selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, aryl, substituted aryl, and halogen; wherein R 5 , R 7 , R 12 , and R 14 are independently selected from hydrogen, alkyl, substituted alkyl, aryl, and substituted aryl; and wherein at least one of R 2 , R 3 , R 5 , R 7 , R 9 , R 10 , R 12 , or R 14 is not hydrogen.
19. The transistor of claim 12 , wherein the tetrahydrotetraazaacene is of Formula (III):
wherein R 2 , R 3 , R 9 , and R 10 are independently selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, substituted alkenyl, substituted alkynyl, aryl, and substituted aryl; and wherein at least one of R 2 , R 3 , R 9 , or R 10 is not hydrogen.
20. The transistor of claim 12 , wherein the tetrahydrotetraazaacene is of Formula (IV):
wherein R 5 , R 7 , R 12 , and R 14 are independently selected from alkyl, substituted alkyl, aryl, and substituted aryl.