IP Library Granted Patent US 7,651,885
Granted Patent B2
US 7,651,885 · App. 11/303,535 · Granted Jan 26, 2010

Electronic device fabrication process

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Quick Facts
Patent No.
US 7,651,885
App. No.
11/303,535
Granted
Jan 26, 2010
Kind
B2
Abstract

A process for fabricating an electronic device including: (a) forming a liquid composition using starting ingredients comprising an organic semiconductor and a stabilizer, wherein the stabilizer comprises a strong electron donor compound or a strong electron acceptor compound, wherein the organic semiconductor exhibits a high oxygen sensitivity in a comparison solution without the stabilizer but a lower oxygen sensitivity in the liquid composition; (b) liquid depositing the liquid composition; and (c) drying the liquid composition to form a layer of the electronic device, wherein the layer comprises the organic semiconductor.

Claims (28)

1. A process for fabricating an electronic device comprising:

(a) forming a liquid composition using starting ingredients comprising an n-type organic semiconductor selected from the group consisting of α,ω-di(perfluoroalkyl)substituted oligothiophenes, α,ω-diacyl substituted oligothiophenes, and metal perfluorophthalocyanines, and mixtures thereof and a stabilizer, wherein the stabilizer comprises a strong electron donor compound selected from the group consisting optionally substituted triarylamines, tetrathiafulvalene and its derivatives, optionally substituted polythiophenes, poly(3,4-ethylenedioxythiophene), 4,4′-bis(carbazol-9-yl)-biphenyl, poly(N-vinylcarbazole), polyaniline, and mixtures thereof, wherein the organic semiconductor exhibits a high oxygen sensitivity in a comparison solution without the stabilizer but a lower oxygen sensitivity in the liquid composition;

(b) liquid depositing the liquid composition; and

(c) drying the liquid composition to form a layer of the electronic device, wherein the layer comprises the organic semiconductor.

2. The process of claim 1 , wherein the strong electron donor compound has an ionization potential ranging from about 3.5 eV to about 7 eV.

3. The process of claim 1 , wherein the strong electron acceptor compound has an electron affinity ranging from about 0.4 eV to about 4 eV.

4. The process of claim 1 , wherein the high oxygen sensitivity is defined by a half-life time of less than 200 minutes and the lower oxygen sensitivity is defined by a half-life time of more than 200 minutes.

5. The process of claim 1 , wherein the n-type organic semiconductor is present in an amount from about 0.5 percent to about 80 percent by weight of the liquid composition, and the strong electron donor compound is present in an amount from about 0.5 percent to about 99.5 percent by weight of the liquid composition.

6. The process of claim 1 , wherein the n-type organic semiconductor is selected from the group consisting of α,ω-diperfluorohexylquaterthiophene, α,ω-diperfluorohexylquinquethiophene, α,ω-diperfluorohexylsexithiophene, α,ω-diheptanoylquaterthiophene, α,ω-diperfluorohexylcarbonylquaterthiophene, perylenetetracarboxylic diimide, copper (II) perfluorophthalocyanine, and mixtures thereof.

7. The process of claim 1 , wherein the organic semiconductor ranges from about 1 percent to about 50 percent by weight of the liquid composition and the stabilizer ranges from about 0.5 percent to about 98 percent by weight of the liquid composition.

8. The process of claim 1 , wherein the liquid depositing is accomplished by a method selected from the group consisting of spin coating, dip coating, blade coating, jet printing, screen printing, stencil printing, microcontact printing, stamping, gravure printing, and flexography.

9. A process for fabricating an electronic device comprising:

(a) forming a liquid composition using starting ingredients comprising a p-type organic semiconductor and a strong electron acceptor compound, wherein the p-type organic semiconductor comprises a 6,13 substituted pentacene selected from the group consisting of 6,13-dihexylpentacene, 6,13-dioctylpentacene, 6,13-didodecylpentacene, 6,13-diphenylpentacene, 6,13-bis(4-butylphenyl)pentacene, 6,13-bis(4-hexylphenyl)pentacene, 6,13-bis(4-octylphenyl)pentacene and exhibits a high oxygen sensitivity in a comparison solution without the strong electron acceptor compound but a lower oxygen sensitivity in the liquid composition;

(b) liquid-depositing the liquid composition; and

(c) drying the liquid composition to form a layer of the electronic device, wherein the layer comprises the p-type organic semiconductor.

10. The process of claim 9 , wherein the strong electron acceptor compound has an electron affinity ranging from about 0.4 eV to about 4 eV.

11. The process of claim 9 , wherein the high oxygen sensitivity is defined by a half-life time of less than 200 minutes and the lower oxygen sensitivity is defined by a half-life time of more than 200 minutes.

12. The process of claim 9 ,

wherein the strong electron acceptor compound is selected from the group consisting of nitrobenzene, fluoronitrobenzene, difluoronitrobenzene, trifluoronitrobenzene, chloronitrobenzene, chlorofluorobenzene, dichloronitrobenzene, nitrotrifluoromethylbenzene, ethylnitrobenzene, dimethylnitrobenzene, dinitrobenzene, chloronitrotoluene, nitrotoluene, fluoronitrotoluene, dinitrotoluene, nitrobenzonitrile, tetracyanoethylene, 7,7,8,8-tetracyanoquinodimethane, phthalic anhydride, nitrobenzaldehyde, and mixtures thereof.

13. The process of claim 9 , wherein the p-type organic semiconductor ranges from about 2 percent to about 50 percent by weight of the liquid composition and the strong electron acceptor compound ranges from about 50 percent to about 98 percent by weight of the liquid composition.

14. The process of claim 9 , wherein the liquid depositing is accomplished by a method selected from the group consisting of spin coating, dip coating, blade coating, jet printing, screen printing, stencil printing, microcontact printing, stamping, gravure printing, and flexography.

15. A process for fabricating a semiconductor layer of a thin film transistor comprising:

(a) forming a liquid composition using starting ingredients comprising a p-type organic semiconductor and a strong electron acceptor compound, wherein the p-type organic semiconductor comprises a 6,13 substituted pentacene selected from the group consisting of 6,13-dihexylpentacene, 6,13-dioctylpentacene, 6,13-didodecylpentacene, 6,13-diphenylpentacene, 6,13-bis(4-butylphenyl)pentacene, 6,13-bis(4-hexylphenyl)pentacene, 6,13-bis(4-octylphenyl)pentacene and exhibits a high oxygen sensitivity in a comparison solution without the stabilizer but a lower oxygen sensitivity in the liquid composition;

(b) liquid depositing the liquid composition; and

(c) drying the liquid composition to form the semiconductor layer of the thin film transistor, wherein the semiconductor layer comprises the p-type organic semiconductor.

16. The process of claim 15 , wherein the strong electron acceptor compound has an electron affinity ranging from about 0.4 eV to about 4 eV.

17. The process of claim 15 , wherein the high oxygen sensitivity is defined by a half-life time of less than 200 minutes and the lower oxygen sensitivity is defined by a half-life time of more than about 200 minutes.

18. The process of claim 15 , wherein the strong electron acceptor compound is selected from the group consisting of nitrobenzene, fluoronitrobenzene, difluoronitrobenzene, trifluoronitrobenzene, chloronitrobenzene, chlorofluorobenzene, dichloronitrobenzene, nitrotrifluoromethylbenzene, ethylnitrobenzene, dimethylnitrobenzene, dinitrobenzene, chloronitrotoluene, nitrotoluene, fluoronitrotoluene, dinitrotoluene, nitrobenzonitrile, tetracyanoethylene, 7,7,8,8-tetracyanoquinodimethane, phthalic anhydride, nitrobenzaldehyde, and mixtures thereof.

Assignments (9)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2005
From: LI, YUNING; ONG, BENG S.; WU, YILIANG
To: XEROX CORPORATION
Reel/Frame 017386/0971 →