IP Library Granted Patent US 7,563,860
Granted Patent B2
US 7,563,860 · App. 11/399,141 · Granted Jul 21, 2009

Semiconductors and electronic devices generated therefrom

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Quick Facts
Patent No.
US 7,563,860
App. No.
11/399,141
Granted
Jul 21, 2009
Kind
B2
Abstract

An electronic device containing a polymer of Formula (I), Formula (II), or mixtures, or isomers thereof wherein each R 1 through R 10 is independently hydrogen, alkyl, aryl, alkoxy, halogen, arylalkyl, cyano, or nitro providing that R 1 and R 2 exclude halogen, nitro and cyano; a and b represent the number of rings; and n represents the number of repeating groups or moieties.

Claims (39)

1. An electronic device comprising a semiconductor selected from the group consisting of at least one of Formula (I), Formula (II), or mixtures thereof

wherein each R 1 through R 10 is independently hydrogen, alkyl, aryl, alkoxy, halogen, arylalkyl, cyano, or nitro providing that R 1 and R 2 exclude halogen, nitro and cyano; a and b represent the number of rings; and n represents the number of repeating groups or moieties.

2. A device in accordance with claim 1 wherein n represents a number of from about 2 to about 5,000, or from 2 to about 2,000.

3. A device in accordance with claim 1 wherein n represents a number of from about 100 to about 1,000.

4. A device in accordance with claim 1 wherein n represents a number of from 2 to about 50.

5. A device in accordance with claim 1 wherein at least one of R 1 to R 10 is alkyl.

6. A device in accordance with claim 1 wherein at least one of R 1 to R 10 is aryl.

7. A device in accordance with claim 1 wherein at least one of R 3 to R 10 is halogen.

8. A device in accordance with claim 1 wherein at least one of R 3 to R 10 is cyano or nitro.

9. A device in accordance with claim 1 wherein R 1 and R 2 are independently dodecyl, pentylphenyl, or octylphenyl.

10. A device in accordance with claim 1 wherein said semiconductor is a p-type semiconductor generated from monomers containing two tertiary amines and two thieno groups, and which p-type semiconductor is one of the following formulas (1)-(4):

wherein at least one of R 1 to R 6 is alkyl or aryl, and n is a number of from 2 to about 100.

11. A device in accordance with claim 1 wherein each R is aryl containing from 6 to about 36 carbon atoms.

12. A device in accordance with claim 1 wherein alkyl and alkoxy contain from 1 to about 25 carbon atoms, and halogen is chloride, fluoride, iodide, or bromide.

13. A device in accordance with claim 1 wherein alkyl or alkoxy contains from about 1 to about 12 carbon atoms.

14. A device in accordance with claim 1 wherein n is a number of from about 10 to about 200, or from about 20 to about 100.

15. A device in accordance with claim 1 wherein n is about 50.

16. A device in accordance with claim 1 wherein aryl contains from 6 to about 48 carbon atoms.

17. A device in accordance with claim 1 wherein aryl contains from 6 to about 18 carbon atoms.

18. A device in accordance with claim 1 wherein said semiconductor is of Formula I.

19. A device in accordance with claim 1 wherein said semiconductor is of Formula II.

20. A thin film transistor comprised of a substrate, a gate electrode, a gate dielectric layer, a source electrode and a drain electrode, and in contact with the source/drain electrodes and the gate dielectric layer a semiconductor layer comprised of at least one semiconducting component having one of the following formulas:

wherein each R 1 through R 10 is independently hydrogen, alkyl, aryl, alkoxy, halogen, arylalkyl, cyano, or nitro providing that R 1 and R 2 exclude halogen, nitro and cyano; a and b represent the number of rings; and n represents the number of repeating groups or moieties.

21. A device in accordance with claim 20 wherein alkyl is butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, or eicosanyl.

22. A device in accordance with claim 20 wherein said semiconducting component is one of the following formulas (1)-(4):

wherein at least one of R 1 to R 6 is alkyl, aryl, or arylalkyl, and n is a number of from 2 to about 200.

23. A device in accordance with claim 20 wherein said semiconducting component is one of the following formulas (5)-(8):

wherein n is from 2 to about 100.

24. A device in accordance with claim 20 wherein said substrate is a plastic sheet of a polyester, a polycarbonate, or a polyimide; said gate source and drain electrodes are each independently comprised of silver, gold, nickel, aluminum, chromium, platinum, or indium titanium oxide, or a conductive polymer; and said gate dielectric layer is comprised of inorganic nitrides or oxides, or organic polymers, silicon nitride, silicon oxide.

25. A device in accordance with claim 20 wherein said semiconductor layer is deposited by solution processes of spin coating, stamp printing, screen printing, or jet printing.

26. An electronic device comprising a semiconductive component and wherein said device is a thin film transistor, and said component is selected from the group consisting of Formula (I), Formula (II), and mixtures thereof

wherein at least one of R 1 to R 10 is a suitable hydrocarbon; a and b represent the number of rings; and n represents the number of repeating units.

27. A device in accordance with claim 1 wherein said arylalkyl contains from 7 to about 37 carbon atoms.

28. A device in accordance with claim 1 wherein said R 1 to R 10 is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosanyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyheptyl, hydroxyoctyl, hydroxynonyl, hydroxydecyl, hydroxyundecyl, hydroxydodecyl, methoxyethyl, methoxypropyl, methoxybutyl, methoxypentyl, methoxyoctyl, trifluoromethyl, perfluoroethyl, perfluoropropyl, pertluorobutyl, perfluoropentyl, perfluorohexyl, perfluoroheptyl, perfluorooctyl, perfluorononyl, perfluorodecyl, perfluoroundecyl, or perfluorodecyl.

29. A device in accordance with claim 1 wherein said aryl or arylalkyl is phenyl, methylphenyl, ethylphenyl, propylphenyl, butylphenyl, pentylphenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, undecylphenyl, dodecylphenyl, tridecylphenyl, tetradecylphenyl, pentadecylphenyl, hexadecylphenyl, heptadecylphenyl, or octadecylphenyl.

30. A device in accordance with claim 1 wherein a is a number of from zero to about 15.

31. A device in accordance with claim 1 wherein b is a number of from zero to about 15.

32. A device in accordance with claim 1 wherein each a and b is a number of from about 1 to about 4.

33. A device in accordance with claim 1 wherein at least one of R 3 to R 10 is alkyl with from 1 to about 12 carbon atoms, alkoxy with from 1 to about 12 carbon atoms, or aryl with from 6 to about 42 carbon atoms.

Assignments (8)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2025
From: XEROX CORPORATION
To: GENESEE VALLEY INNOVATIONS, LLC
Reel/Frame 073842/0479 →
SECOND LIEN NOTES PATENT SECURITY AGREEMENT Recorded Jul 2, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 071785/0550 →
FIRST LIEN NOTES PATENT SECURITY AGREEMENT Recorded Apr 11, 2025
From: XEROX CORPORATION
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 070824/0001 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT RF 064760/0389 Recorded Feb 13, 2024
From: CITIBANK, N.A., AS COLLATERAL AGENT
To: XEROX CORPORATION
Reel/Frame 068261/0001 →
SECURITY INTEREST Recorded Nov 20, 2023
From: XEROX CORPORATION
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 065628/0019 →
SECURITY INTEREST Recorded Jun 22, 2023
From: XEROX CORPORATION
To: CITIBANK, N.A., AS COLLATERAL AGENT
Reel/Frame 064760/0389 →
RELEASE OF SECURITY INTEREST IN PATENTS AT R/F 062740/0214 Recorded May 18, 2023
From: CITIBANK, N.A., AS AGENT
To: XEROX CORPORATION
Reel/Frame 063694/0122 →
SECURITY INTEREST Recorded Nov 10, 2022
From: XEROX CORPORATION
To: CITIBANK, N.A., AS AGENT
Reel/Frame 062740/0214 →