Naphthalene-based semiconductor materials and methods of preparing and use thereof
View Patent ↗Provided are mono- and diimide naphthalene compounds for use in the fabrication of various device structures. In some embodiments, the naphthalene core of these compounds are mono-, di-, or tetra-substituted with cyano group(s) or other electron-withdrawing substituents or moieties. Such mono- and diimide naphthalene compounds also can be optionally N-substituted.
1. A compound of formula I or formula II:
wherein:
R 1 and R 2 independently are selected from a) H, b) a C 1-20 alkyl group, c) a C 1-20 haloalkyl group, d) a C 2-20 alkenyl group, e) a C 2-20 alkynyl group, f) a C 3-10 cycloalkyl group, g) a C 6-14 aryl group, h) a 3-14 membered cycloheteroalkyl group, and i) a 5-14 membered heteroaryl group, wherein each of the C 1-20 alkyl group, the C 2-20 alkenyl group, the C 2-20 alkynyl group, the C 3-10 cycloalkyl group, the C 6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-5 R a groups;
R a, at each occurrence, is independently selected from a) a halogen, b) —CN, c) —NO 2 , d) —N + (R b ) 3, e) —S(O) m R b , f) —S(O) m OR b , g) —C(O)R b , h) —C(O)OR b , i) —(CH 2 CH 2 O) n CH 2 CH 2 OH, and j) a C 1-20 haloalkyl group;
R b , at each occurrence, is independently selected from a) H, b) a C 1-20 alkyl group, c) a C 1-20 haloalkyl group, d) a C 6-14 aryl group, e) a —(C 1-20 alkyl)—C 6-14 aryl group, and f) a —(C 1-20 haloalkyl)—C 6-14 aryl group;
m is 0, 1 or 2; and
n is 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.
2. The compound of claim 1 , wherein the compound is of formula I, and at least one of R 1 and R 2 is a C 1-20 alkyl group.
3. The compound of claim 2 , wherein the compound is of formula I, and R 1 and R 2 are straight-chain C 3-16 alkyl groups.
4. The compound of claim 1 , wherein the compound is of formula I, and at least one of R 1 and R 2 is a straight-chain C 1-20 fluoroalkyl group.
5. The compound of claim 1 , wherein the compound is of formula I, and at least one of R 1 and R 2 is a C 3-10 cycloalkyl group.
6. The compound of claim 1 selected from N,N′-bis(n-octyl)-2-cyanonaphthalene-1,4,5,8-bis(dicarboximide) and N,N′-bis(n-octyl)-2,6-dicyanonaphthalene-1,4,5,8-bis(dicarboximide).
7. A thin film semiconductor comprising one or more compounds of claim 1 .
8. A composite comprising a substrate and the thin film semiconductor of claim 7 deposited on the substrate.
9. A transistor device comprising the composite of claim 8 .
10. A transparent organic transistor device comprising the composite of claim 8 .
11. The compound of claim 1 , wherein the compound is of formula I.
12. A thin film semiconductor comprising one or more compounds of claim 11 .
13. A thin film semiconductor comprising one or more compounds of claim 2 .
14. A thin film semiconductor comprising one or more compounds of claim 3 .
15. A thin film semiconductor comprising one or more compounds of claim 4 .
16. A thin film semiconductor comprising one or more compounds of claim 5 .
17. A thin film semiconductor comprising a compound of claim 6 , wherein the compound is N,N′-bis(n-octyl)-2-cyanonaphthalene-1,4,5,8-bis(dicarboximide).
18. A transistor device comprising the thin film semiconductor of claim 17 .
19. A thin film semiconductor comprising a compound of claim 6 , wherein the compound is N,N′-bis(n-octyl)-2,6-dicyanonaphthalene-1,4,5,8-bis(dicarboximide).
20. A transistor device comprising the thin film semiconductor of claim 19 .