IP Library › Granted Patent US 7,671,202

Granted Patent B2

US 7,671,202 · App. 11/043,814 · Granted Mar 2, 2010

Perylene n-type semiconductors and related devices

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Quick Facts

Patent No.: US 7,671,202
App. No.: 11/043,814
Granted: Mar 2, 2010
Kind: B2

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Abstract

Mono- and diimide perylene and naphthalene compounds, N- and core-substituted with electron-withdrawing groups, for use in the fabrication of various device structures.

Claims (82)

1. An n-type semiconductor compound having formula I:

wherein:

each of R 1 -R 8 independently is selected from H, —NO 2 , —CN, halide, —SO 3 H, —N + H 3 , —N + H 2 (alkyl), —N + H(alkyl) 2 , —N + (alkyl) 3 , —C(O)R, —CO 2 R, an alkyl moiety, a substituted alkyl moiety, a cycloalkyl moiety, a substituted cycloalkyl moiety, an aryl moiety, a substituted aryl moiety, a polycyclic aryl moiety, and a substituted polycyclic aryl moiety,

wherein each of the alkyl moiety, the substituted alkyl moiety, the cycloalkyl moiety, the substituted cycloalkyl moiety, the aryl moiety, the substituted aryl moiety, the polycyclic aryl moiety, and the substituted polycyclic aryl moiety comprises at least one of —NO 2 , —CN, halide, —SO 3 H, —N + H 3 , —N + H 2 (alkyl), —N + H(alkyl) 2 , —N + (alkyl) 3 , —C(O)R, and —CO 2 R, and

at least one of R 1 , R 4 , R 5 , and R 8 is —CN;

R 9 and R 10 independently are selected from H, an alkyl moiety, a substituted alkyl moiety, a cycloalkyl moiety, a substituted cycloalkyl moiety, an aryl moiety, and a substituted aryl moiety,

wherein each of the alkyl moiety, the substituted alkyl moiety, the cycloalkyl moiety, the substituted cycloalkyl moiety, the aryl moiety, and the substituted aryl moiety optionally comprises —NO 2 , —CN, halide, —SO 3 H, —N + H 3 , —N + H 2 (alkyl), —N + H(alkyl) 2 , —N + (alkyl) 3 , —C(O)R, or —CO 2 R,

each methylene (—CH 2 —) in the alkyl moiety or the substituted alkyl moiety optionally is replaced with a heteroatom selected from O and N, and

each methene (—CH═) in the aryl moiety or the substituted aryl moiety optionally is replaced with a heteroatom selected from O and N; and

R, at each occurrence, is H, an alkyl moiety, or phenyl.

2. The compound of claim 1 , wherein at least one of R 9 and R 10 is selected from an alkyl moiety, a substituted alkyl moiety, and a cycloalkyl moiety.

3. The compound of claim 2 , wherein at least one of R 9 and R 10 is a halo substituted alkyl moiety.

4. The compound of claim 3 , wherein the halo substituted alkyl moiety comprises F or Cl.

5. The compound of claim 1 , wherein each of R 1 and R 4 or each of R 5 and R 8 is —CN.

6. The compound of claim 5 , wherein each of R 2 , R 3 , R 6 , and R 7 is H, whichever of R 1 , R 4 , R 5 , and R 8 that is not —CN is H, and R 9 and R 10 independently are an alkyl moiety, a substituted alkyl moiety, or a cycloalkyl moiety.

7. The compound of claim 1 , wherein each of R 1 and R 5 or each of R 4 and R 8 is —CN.

8. The compound of claim 7 , wherein each of R 2 , R 3 , R 6 , and R 7 is H, whichever of R 1 , R 4 , R 5 , and R 8 that is not —CN is H, and R 9 and R 10 independently are an alkyl moiety, a substituted alkyl moiety, or a cycloalkyl moiety.

9. The compound of claim 1 , wherein each of R 1 , R 4 , R 5 , and R 8 is —CN.

10. An n-type semiconductor compound selected from:

N,N′-bis(cyclohexyl)-1,7-dicyano-perylene-3,4:9,10-bis(dicarboximide);

N,N′-bis(cyclohexyl)-1,6-dicyano-perylene-3,4:9,10-bis(dicarboximide);

N,N′-bis(1H,1H-perfluorobutyl)-1,7-dicyano-perylene-3,4:9,10-bis(dicarboximide);

N,N′-bis(1H,1H-perfluorobutyl)-1,6-dicyano-perylene-3,4:9,10-bis(dicarboximide);

N,N′-bis(n-octyl)-1,7-dicyano-perylene-3,4:9,10-bis(dicarboximide);

N,N′-bis(n-octyl)-1,6-dicyano-perylene-3,4:9,10-bis(dicarboximide);

N,N′-bis(n-octyl)-1-cyano-7-bromo-perylene-3,4:9,10-bis(dicarboximide); and

N,N′-bis(n-octyl)-1-cyano-6-bromo-perylene-3,4:9,10-bis(dicarboximide).

11. An n-type semiconductor compound having formula III:

wherein:

two of R 1 -R 4 are —CN and the other two of R 1 -R 4 are H;

R 9 and R 10 independently are selected from H, an alkyl moiety, a substituted alkyl moiety, a cycloalkyl moiety, a substituted cycloalkyl moiety, an aryl moiety, and a aryl moiety, wherein at least one of R 9 and R 10 is a halo substituted alkyl moiety,

each methylene (—CH 2 —) in the alkyl moiety or the substituted alkyl moiety optionally is replaced with a heteroatom selected from O and N, and

each methene (—CH═) in the aryl moiety or the substituted aryl moiety optionally is replaced with a heteroatom selected from O and N; and

R, at each occurrence, is H, an alkyl moiety, or phenyl.

12. The compound of claim 11 , wherein each of R 1 and R 4 or each of R 2 and R 3 is —CN.

13. The compound of claim 11 , wherein each of R 1 and R 3 or each of R 2 and R 4 is —CN.

14. A composite comprising a substrate and a semiconductor component thereon, said semiconductor component comprising a compound of formula I′:

wherein:

R 1 , R 4 , R 5 , and R 8 independently are selected from H and —CN,

wherein at least one of R 1 , R 4 , R 5 , and R 8 is —CN;

R 9 and R 10 independently are selected from H, an alkyl moiety, a substituted alkyl moiety, a cycloalkyl moiety, a substituted cycloalkyl moiety, an aryl moiety, and a substituted aryl moiety,

each methylene (—CH 2 —) in the alkyl moiety or the substituted alkyl moiety optionally is replaced with a heteroatom selected from O and N, and

each methene (—CH═) in the aryl moiety or the substituted aryl moiety optionally is replaced with a heteroatom selected from O and N; and

R, at each occurrence, is H, an alkyl moiety, or phenyl.

15. The composite of claim 14 , wherein R 9 and R 10 independently are selected from an alkyl moiety, a substituted alkyl moiety, a cycloalkyl moiety, and a substituted aryl moiety.

16. The composite of claim 15 , wherein at least one of R 9 and R 10 is a halo substituted alkyl moiety.

17. The composite of claim 16 , wherein the halo substituted alkyl moiety comprises F or Cl.

18. The composite of claim 14 , wherein each of R 1 and R 4 or each of R 5 and R 8 is —CN.

19. The composite of claim 18 , wherein R 9 and R 10 independently are an alkyl moiety, a substituted alkyl moiety, or a cycloalkyl moiety.

20. The composite of claim 14 , wherein each of R 1 and R 5 or each of R 4 and R 8 is —CN.

21. The composite of claim 20 , wherein, R 9 and R 10 independently are an alkyl moiety, a substituted alkyl moiety, or a cycloalkyl moiety.

22. The composite of claim 14 , wherein the compound is selected from: