IP Library Granted Patent US 9,500,952
Granted Patent B2
US 9,500,952 · App. 14/966,570 · Granted Nov 22, 2016

Orthogonal processing of organic materials used in electronic and electrical devices

Inventors: Christopher K. Ober (Ithaca, NY); George Malliaras (Ithaca, NY); Jin-Kyun Lee (Incheon, KR); Alexander Zakhidov (McKinney, TX); Margarita Chatzichristidi (Athens, GR); Priscilla Dodson (Berkeley, CA)
Assignee: Cornell University
G03F7/20G03F7/0046G03F7/0048G03F7/0392G03F7/16G03F7/30G03F7/325G03F7/40H01L51/0018Y02E10/549Y10T428/24802
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Quick Facts
Patent No.
US 9,500,952
App. No.
14/966,570
Granted
Nov 22, 2016
Kind
B2
Abstract

An orthogonal process for photolithographic patterning organic structures is disclosed. The disclosed process utilizes fluorinated solvents or supercritical CO 2 as the solvent so that the performance of the organic conductors and semiconductors would not be adversely affected by other aggressive solvent. One disclosed method may also utilize a fluorinated photoresist together with the HFE solvent, but other fluorinated solvents can be used. In one embodiment, the fluorinated photoresist is a resorcinarene, but various fluorinated polymer photoresists and fluorinated molecular glass photoresists can be used as well. For example, a copolymer perfluorodecyl methacrylate (FDMA) and 2-nitrobenzyl methacrylate (NBMA) is a suitable orthogonal fluorinated photoresist for use with fluorinated solvents and supercritical carbon dioxide in a photolithography process. The combination of the fluorinated photoresist and the fluorinated solvent provides a robust, orthogonal process that is yet to be achieved by methods or devices known in the art.

Claims (26)

1. A method for patterning a device, the method comprising:

coating a substrate with a layer of fluorinated photoresist material;

selectively exposing portions of the layer of fluorinated photoresist material to radiation;

contacting the layer of fluorinated photoresist material with a first fluorinated solvent to develop a patterned fluorinated photoresist; and

removing the patterned fluorinated photoresist with a second fluorinated solvent that is the same as or different from the first fluorinated solvent.

2. The method of claim 1 , wherein the first fluorinated solvent comprises a hydrofluoroether.

3. The method of claim 1 , wherein the second fluorinated solvent comprises a hydrofluoroether.

4. The method of claim 1 , wherein both the first and second fluorinated solvents comprise a hydrofluoroether.

5. The method of claim 1 , wherein the device is at least part of an organic thin film transistor, an organic light-emitting diode, an organic photovoltaic, or an organic sensor.

6. The method of claim 1 , wherein the layer of fluorinated photoresist material is coated from a composition comprising a fluorinated coating solvent.

7. The method of claim 6 , wherein the fluorinated coating solvent comprises at least one hydrofluoroether.

8. The method of claim 1 , wherein the fluorinated photoresist material comprises a photo-acid generator.

9. The method of claim 8 , wherein the photo-acid generator is non-ionic.

10. The method of claim 1 , wherein the fluorinated photoresist material is configured to form a negative tone image.

11. A method for patterning a device, the method comprising:

coating a substrate with a layer of fluorinated photoresist material, wherein the substrate comprises one or more layers comprising one or more thin films of at least one active organic electronic material;

selectively exposing portions of the layer of fluorinated photoresist material to radiation; and

contacting the layer of fluorinated photoresist material with a fluorinated solvent to develop a patterned fluorinated photoresist.

12. The method of claim 11 , wherein at least one of the active organic electronic material comprises a semiconducting polymer or a small molecule.

13. The method of claim 11 , wherein the fluorinated solvent comprises a hydrofluoroether.

14. The method of claim 11 , wherein the device is at least part of an organic thin film transistor, an organic light-emitting diode, an organic photovoltaic, or an organic sensor.

15. The method of claim 11 , wherein the layer of fluorinated photoresist material is coated from a composition comprising a fluorinated coating solvent.

16. The method of claim 15 , wherein the fluorinated coating solvent comprises at least one hydrofluoroether.

17. The method of claim 11 , wherein the fluorinated photoresist material comprises a photo-acid generator.

18. The method of claim 17 , wherein the photo-acid generator is non-ionic.

19. The method of claim 11 , wherein the fluorinated photoresist material is configured to form a negative tone image.

Assignments (2)
CONFIRMATORY LICENSE Recorded Feb 1, 2017
From: CORNELL UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 041588/0879 →
CONFIRMATORY LICENSE Recorded Mar 31, 2016
From: CORNELL UNIVERSITY
To: NATIONAL SCIENCE FOUNDATION
Reel/Frame 038311/0797 →
Continuity (5)
Continuation 14471095 · Aug 28, 2014
Continuation 12994353
Provisional Application 61140420 · Dec 23, 2008
Provisional Application 61055798 · May 23, 2008
Related Publication 20160097977A1 · Apr 7, 2016