# US 10,503,074 B2 · Photolithographic patterning of devices

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- Number: US 10,503,074 B2
- Document ID: US10503074B2
- Status: Granted
- Kind: B2
- Application number: 15/501,116
- Filed: 2015-07-31
- Published: 2017-08-03
- Granted: 2019-12-10
- Earliest claimed: 2014-08-01
- Assignees: Orthogonal, Inc.
- Applicants: Orthogonal, Inc.
- Inventors: John Andrew Defranco; Charles Warren Wright; Douglas Robert Robello; Frank Xavier Byrne; Diane Carol Freeman; Terrence Robert O'Toole
- Web page: https://patentgrep.com/patent/US10503074B2

## CPC

- G03F 7/40: Treatment after imagewise removal, e.g. baking
- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- G03F 7/42: Stripping or agents therefor
- H10K 71/16: using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K 71/233: {by photolithographic etching}
- H10K 71/40: Thermal treatment, e.g. annealing in the presence of a solvent vapour
- H10P 76/202: {for lift-off processes}
- H10P 76/2041: {Photolithographic processes}
- H10K 71/221: {by lift-off techniques}
- Y02E 10/549: Organic PV cells
- Y02P 70/50: Manufacturing or production processes characterised by the final manufactured product
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A method of making a device includes providing a fluorinated material layer over the device substrate having one or more target areas for patterning. One or more lift-off structures are formed at least in part by developing a first pattern of one or more open areas in the fluorinated material layer in alignment with the one or more target areas by contact with a developing agent including a fluorinated solvent which dissolves the fluorinated material at a first rate. After patterning, the lift-off structures are removed by contact with a lift-off agent including a fluorinated solvent wherein the lift-off agent dissolves the fluorinated material at a second rate that is at least 150 nm/sec and higher than the first rate.

## Claims

### Claim 1

A method of making a device comprising:
a) providing a device substrate having one or more target areas for patterning;
b) providing a fluorinated material layer over the device substrate;
c) forming one or more lift-off structures at least in part by developing a first pattern of one or more open areas in the fluorinated material layer in alignment with the one or more target areas by contact with a developing agent comprising a fluorinated solvent, wherein the developing agent dissolves the fluorinated material at a first rate;
d) patterning the device substrate by
i) etching at least a portion of the one or more target areas using the one or more lift-off structures as an etch mask, or
ii) depositing one or more active material layers through the first pattern of open areas and onto the one or more target areas, or
both i) and ii); and
e) removing the one or more lift-off structures by contact, at a temperature that is at least 10° C. higher than contact with the developing agent, with a lift-off agent comprising a fluorinated solvent wherein the lift-off agent dissolves the fluorinated material at a second rate that is at least 150 nm/sec and higher than the first rate.

### Claim 2 (depends on 1)

The method of claim 1 wherein contact with the developing agent is conducted at a temperature in a range of 15° C. to 25° C. and contact with the lift-off agent is conducted in a range of 35° C. to 65° C.

### Claim 3 (depends on 1)

The method of claim 1 wherein the composition of the lift-off agent includes a different fluorinated solvent than the developing agent.

### Claim 4 (depends on 1)

The method of claim 1 wherein the developing agent comprises a mixture of first and second fluorinated solvents and the lift-off agent comprises at least one of the first and second fluorinated solvents at a different concentration than in the developing agent.

### Claim 5 (depends on 1)

The method of claim 1 wherein the lift-off agent comprises a mixture of first and second fluorinated solvents and the developing agent comprises at least one of the first and second fluorinated solvents at a different concentration than in the lift-off agent.

### Claim 6 (depends on 1)

The method of claim 1 wherein the fluorinated material layer includes a copolymer comprising at least two distinct repeating units including a first repeating unit having a fluorine-containing group and a second repeating unit having a non-photoactive functional group that does not include a protic substituent, wherein the copolymer has a total fluorine content of at least 45% by weight.

### Claim 7 (depends on 6)

The method according to claim 6 wherein the functional group includes an aliphatic hydrocarbon that does not include a protic substituent.

### Claim 8 (depends on 7)

The method according to claim 7 wherein the copolymer has a total fluorine content in a range of 46 to 53% by weight.

### Claim 9 (depends on 6)

The method according to claim 6 wherein the functional group includes an aromatic hydrocarbon that does not include a protic substituent.

### Claim 10 (depends on 1)

The method of claim 1 wherein the fluorinated material layer is substantially not directly photopatternable by exposure to radiation having a wavelength of 365 nm or above.

### Claim 11 (depends on 1)

The method according to of claim 1 wherein the one or more lift-off structures further includes a patterned resist provided over the fluorinated material layer, wherein the patterned resist acts as an etch mask for the developing of the first pattern of open areas in the fluorinated material layer.

### Claim 12 (depends on 11)

The method according to claim 11 wherein the patterned resist is provided by printing a resist material.

### Claim 13 (depends on 12)

The method according to claim 12 wherein the printing includes ink jet printing, flexographic printing, gravure printing, screen printing, electrophotographic printing, or laser or thermal transfer of the resist material from a donor sheet.

### Claim 14 (depends on 11)

The method according to claim 11 wherein the patterned resist is provided by photoimaging a photoresist material.

### Claim 15 (depends on 14)

The method according to claim 14 wherein the photoresist material is provided from a composition comprising a non-fluorinated solvent.

### Claim 16 (depends on 15)

The method according to claim 15 wherein the non-fluorinated solvent is water or an alcohol.

### Claim 17 (depends on 15)

The method according to claim 15 wherein the non-fluorinated solvent is a non-protic, non-aromatic organic solvent having an ether group, an ester group, a ketone group or a combination thereof, or a non-protic aromatic organic solvent.

### Claim 18 (depends on 14)

The method according to claim 14 wherein the photoresist material is a fluorinated photoresist material provided from a composition comprising a fluorinated solvent selected not to dissolve a substantial portion of the underlying fluorinated material layer.

### Claim 19 (depends on 1)

The method of claim 1 wherein the deposition of the one or more active material layers includes vapor deposition.

### Claim 20 (depends on 1)

The method of claim 1 wherein the deposition of the one or more active material layers includes deposition from a liquid comprising at least one of the active materials.

### Claim 21 (depends on 1)

The method of claim 1 wherein the one or more lift-off structures has a thickness in a range of 0.2 to 5.0 μm.

### Claim 22 (depends on 1)

The method of claim 1 wherein the active material is an active organic material.

### Claim 23 (depends on 1)

The method of claim 1 wherein the device is a display device, a touch-sensitive device, an OLED device, an OTFT device, a photovoltaic device, a bioelectronic device, a medical device, a MEMS device or an integrated circuit chip.

### Claim 24 (depends on 1)

The method of claim 1 wherein the substrate comprises a substrate layer having an active organic material and at least one lift-off structure covers at least a portion of the substrate layer having the active organic material.