Electronic device fabrication process

• US 20070141747A1
• Filed: 12/16/2005
• Published: 06/21/2007
• Est. Priority Date: 12/16/2005
• Status: Active Grant

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Wu, Yiliang, Li, Yuning, Ong, Beng
• Granted Patent: US 7,651,885 B2
• Time in Patent Office: Days
• US Class Current: 438/99
• CPC Class Codes: H10K 10/464 Lateral top-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 10/466 Lateral bottom-gate IGFETs comprising only a single gate
• CPC Class Codes: H10K 71/15 characterised by the solvent used
• CPC Class Codes: H10K 71/30 Doping active layers, e.g. electron transporting layers
• CPC Class Codes: H10K 85/622 containing four rings, e.g. pyrene

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

1. A process for fabricating an electronic device comprising:

(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.

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 liquid composition comprises an n-type organic semiconductor and a strong electron donor compound.

6. The process of claim 5, wherein the n-type organic semiconductor is selected from the group consisting of α

,ω

-di(perfluoroalkyl)substituted oligothiophenes, α

,ω

-diacyl substituted oligothiophenes, substituted arylenetetracarboxylic diimides, and metal perfluorophthalocyanines, and mixtures thereof, 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.

7. The process of claim 5, 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, naphthalenetetracarboxylic diimide, perylenetetracarboxylic diimide, copper (II) perfluorophthalocyanine, and mixtures thereof, and the strong electron donor compound is selected from the group consisting optionally substituted triarylamines, tetrathiafulvalene and its derivatives, optionally substituted oligothiophenes, optionally substituted polythiophenes, poly(3,4-ethylenedioxythiophene), 4,4′

-bis(carbazol-9-yl)-biphenyl, poly(N-vinylcarbazole), polyaniline, and mixtures thereof.

8. 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.

9. 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.

10. 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 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.

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

12. The process of claim 10, 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.

13. The process of claim 10, wherein the p-type organic semiconductor is selected from the group consisting of substituted naphthacene, substituted pentacene, optionally substituted oligothiophenes, and optionally substituted polythiophenes, and a mixture thereof, in an amount from about 0.5 percent to about 80 percent by weight of the liquid composition, and the strong electron acceptor compound is present in an amount from about 0.5 percent to about 99.5 percent by weight of the liquid composition.

14. The process of claim 10, wherein the p-type organic semiconductor is selected from the group consisting of 5,6,11,12-tetraethylnaphthacene, 5,6,11,12-tetrapropylnaphthacene, 5,6,11,12-tetrabutylnaphthacene, 5,6,11,12-tetrapentylnaphthacene, 5,6,11,12-tetrahexylnaphthacene, 5,6,11,12-tetraheptylnaphthacene, 5,6,11,12-tetrahexylnaphthacene, 5,6,11,12-tetraphenylnaphthacene (rubrene), 5,6,11,12-tetratolylnaphthacene, 5,6,11,12-tetra(ethylphenyl)naphthacene, 5,6,11,12-tetra(propylphenyl)naphthacene, 5,6,11,12-tetra(butylphenyl)naphthacene, 5,6,11,12-tetra(bromophenyl)naphthacene, 5,6,11,12-tetra(chlorophenyl)naphthacene, 5,6,11,12-tetra(fluorophenyl)naphthacene, 5,12-dimethoxy-6,11-diphenylnaphthacene, 5,12-dimethoxy-6,11 -ditolylnaphthacene, 5,12-dimethoxy-6,11-di(ethylphenyl)naphthacene, 5,12-dimethoxy-6,11-di(propylphenyl)naphthacene, 5,12-dimethoxy-6,11-di(butylphenyl)naphthacene, 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, 1,4,8,11-tetramethylpentacene, 2,9-dihexylpentacene, 2,10-dihexylpentacene, 2,9-dinonylpentacene, 2,10-dinonylpentacene, 2,9-didodecylpentacene, 2,10-didodecylpentacene, 2,9-di-sec-butylpentacene, 2,10-di-sec-butylpentacene, 2,9-di-3,5,5-trimethylhexylpentacene, 2,10-di-3,5,5-trimethylhexylpentacene, 2,9-di-2-ethylhexylpentacene, 2,10-di-2-ethylhexylpentacene);

and 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.

15. The process of claim 10, 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.

16. The process of claim 10, 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.

17. 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 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.

18. The process of claim 17, wherein the strong electron acceptor compound has an electron affinity ranging from about 0.4 eV to about 4 eV.

19. The process of claim 17, 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.

20. The process of claim 17, wherein the p-type organic semiconductor is selected from the group consisting of substituted naphthacene, substituted pentacene, optionally substituted oligothiophenes, and optionally substituted polythiophenes, and a mixture thereof, in an amount from about 0.5 percent to about 80 percent by weight of the liquid composition, and the strong electron acceptor compound is present in an amount from about 0.5 percent to about 99.5 percent by weight of the liquid composition.