# US 8,540,888 B1 · Methods of patterning layered-material and forming imprinting mold

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- Number: US 8,540,888 B1
- Document ID: US8540888B1
- Status: Granted
- Kind: B1
- Application number: 13/609,854
- Filed: 2012-09-11
- Published: 2013-09-26
- Granted: 2013-09-24
- Earliest claimed: 2012-03-20
- Assignees: Industrial Technology Research Institute
- Applicants: Chin-Tien Yang; Ming-Chia Li; Chung-Ta Cheng
- Inventors: Chin-Tien Yang; Ming-Chia Li; Chung-Ta Cheng
- Web page: https://patentgrep.com/patent/US8540888B1

## CPC

- G03F 7/027: Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence)
- B82Y 10/00: Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
- B82Y 40/00: Manufacture or treatment of nanostructures
- G03F 7/0002: {Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping}
- G03F 7/0042: {with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence)}
- 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)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES

## Abstract

Disclosed is a method of patterning a layered material. A layered material is provided, and a photoresist layer is formed thereon. The photoresist layer is patterned by a focused laser beam to expose a part of the layered material. The exposed layered material is etched to pattern the layered material.

## Claims

### Claim 1

A method of patterning a layered material, comprising:
providing a layered material;
forming a photoresist layer on the layered material;
patterning the photoresist layer by a focused laser beam to expose a part of the layered material; and
etching the exposed part of the layered material to pattern the layered material,
wherein the photoresist layer has a chemical structure as shown in Formula 1, 2, 3, 4, 5, 6, or 7, and the Formulae are as follows:
wherein each A independently represents a substituted or a non-substituted cyclic alkyl group;
R1 represents a CH2 group, an oxygen atom, or a SO2 group;
each R2 independently represents a hydrogen atom, an azo group, or a substituted or a non-substituted polymethine group;
each X1 independently represent an oxygen atom, a CH2 group, an alkyl group, or an N—R3 group, wherein R3 represents a hydrogen atom, a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 as carboxyl group, a substituted or a non-substituted C1-18 arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X2 independently represents an oxygen atom or a C(CN)2 group; and
each X3 independently represents an oxygen atom posing one negative charge, a hydroxyl group, or a C(CN)2 group;
wherein each B independently represents a substituted or a non-substituted aromatic hydrocarbon ring, a substituted or a non-substituted aromatic heterocyclic ring, or a substituted or a non-substituted condensed ring including an aromatic hydrocarbon ring;
each R4 independently represents a hydrogen atom, a C═S group, a substituted or non-substituted alkyl group, a substituted or non-substituted aryl group, a substituted or non-substituted aralkyl group, or a substituted or non-substituted heterocyclic group;
each X4 independently represents an oxygen atom, a substituted or non-substituted alkyl group, or an N—R5 group, wherein R5 represents a hydrogen atom, a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each R5 independently represents an oxygen atom, a C(CN)2 group, or a C═O group; and
M represents Fe, Co, Cu, Ni, or Zn;
wherein C represents a substituted or a non-substituted cyclic alkyl group;
each L independently represents a substituted or a non-substituted methine group;
each R6 independently represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X6 independently represents an oxygen atom, a CH2 group, or an N—R7 group, wherein R7 represents a substituted or a non-substituted C1-18 alkyl group;
each X7 independently represents an oxygen atom or a C(CN)2 group;
each X8 independently represents a substituted or a non-substituted alkylene group, or an a substituted or a non-substituted alkylene group containing an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
each m independently represents an integer of 0 or 1;
wherein each L′ independently represent a substituted or a non-substituted methine group;
each R8 independently represents a hydrogen atom, a substituted or a non-substituted alkyl group, a substituted or a non-substituted aryl group, a substituted or a non-substituted aralkyl group, a substituted or a non-substituted heterocyclic ring, or a ferrocenyl group;
R9 represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X9 independently represents an oxygen atom, a CH2 group, or an N—R10 group, wherein R10 represents a substituted or a non-substituted C1-18 alkyl group;
each X10 independently represents an oxygen atom or a C(CN)2 group;
X11 represents a substituted or a non-substituted alkylene group, or a substituted or a non-substituted alkylene group containing an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
n is an integer of 0 or 1;
wherein each L″ independently represent a substituted or a non-substituted methine group;
each R11 independently represents a hydrogen atom, a substituted or a non-substituted alkyl group, a substituted or a non-substituted aryl group, a substituted or a non-substituted aralkyl group, or a substituted or a non-substituted heterocyclic ring;
R12 represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X12 independently represents an oxygen atom, a CH2 group, or an N—R13 group, wherein R13 represents a substituted or a non-substituted C1-18 alkyl group;
each X13 independently represents an oxygen atom or a C(CN)2 group;
each X14 independently represents a substituted or a non-substituted alkylene group, or a substituted or a non-substituted alkylene group containing an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
each k independently represents an integer of 0 or 1;
wherein each L′ independently represent a substituted or a non-substituted methine group;
R14 represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X15 independently represents an oxygen atom, a sulfur atom, a CH2 group, or an N—R15 group, wherein R15 represents a hydrogen atom or a substituted or a non-substituted C1-18 alkyl group;
each X16 independently represents an oxygen atom, a sulfur atom, or a C(CN)2 group;
X17 represents a substituted or a non-substituted alkylene group, or a substituted or a non-substituted alkylene group containing an oxygen 125 atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
n is an integer of 0 or 1.

### Claim 2 (depends on 1)

The method as claimed in claim 1, wherein the photoresist layer has a thickness of 30 nm to 200 nm.

### Claim 3 (depends on 1)

The method as claimed in claim 1, wherein the layered material comprises a substrate, and the substrate comprises crystalline silicon, quartz, silicon oxide, sapphire, aluminum nitride, gallium nitride, glass, polymer, or metal.

### Claim 4 (depends on 1)

The method as claimed in claim 1, wherein the layered material comprises an intermediate layer disposed between the substrate and the photoresist layer, the substrate comprises crystalline silicon, quartz, silicon oxide, sapphire, aluminum nitride, gallium nitride, glass, polymer, or metal, and the intermediate layer comprises aluminum oxide, aluminum nitride, silicon carbide, silicon oxide, zinc sulfide-silicon oxide, polymer, or metal.

### Claim 5 (depends on 1)

The method as claimed in claim 1, wherein the focused laser beam has a wavelength of 200 nm to 530 nm.

### Claim 6 (depends on 1)

The method as claimed in claim 1, wherein the step of etching the exposed part of the layered material comprises dry etching, wet etching, or combinations thereof.

### Claim 7 (depends on 1)

The method as claimed in claim 1, after the step of etching the exposed part of the layered material to pattern the layered material, further comprising:
plating a metal layer on the patterned photoresist layer and the etched layered material; and
removing the patterned photoresist layer and the etched layered material from the metal layer to obtain an imprinting mold.

### Claim 8 (depends on 1)

The method as claimed in claim 1, after the step of etching the exposed part of the layered material to pattern the layered material, further comprising:
removing the patterned photoresist layer.

### Claim 9 (depends on 8)

The method as claimed in claim 8, after the step of removing the patterned photoresist layer, further comprising:
plating a metal layer on the etched layered material; and
removing the etched layered material from the metal layer to obtain an imprinting mold.

### Claim 10

A method of forming an imprinting mold, comprising:
providing a layered material;
forming a photoresist layer on the layered material;
patterning the photoresist layer by a focused laser beam to expose a part of the layered material;
plating a metal layer on the patterned photoresist layer and the exposed part of the layered material; and
removing the patterned photoresist layer and the layered material from the metal layer to obtain an imprinting mold,
wherein the photoresist layer has a chemical structure as shown in Formula 1, 2, 3, 4, 5, 6, or 7, and the Formulae are as follows:
wherein each A independently represents a substituted or a non-substituted cyclic alkyl group;
R1 represents a CH2 group, an oxygen atom, or a SO2 group;
each R2 independently represents a hydrogen atom, an azo group, or a substituted or a non-substituted polymethine group;
each X1 independently represent an oxygen atom, a CH2 group, an alkyl group, or an N—R3 group, wherein R3 represents a hydrogen atom, a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X2 independently represents an oxygen atom or a C(CN)2 group; and
each X3 independently represents an oxygen atom posing one negative charge, a hydroxyl group, or a C(CN)2 group;
wherein each B independently represents a substituted or a non-substituted aromatic hydrocarbon ring, a substituted or a non-substituted aromatic heterocyclic ring, or a substituted or a non-substituted condensed ring including an aromatic hydrocarbon ring;
each R4 independently represents a hydrogen atom, a C═S group, a substituted or non-substituted alkyl group, a substituted or non-substituted aryl group, a substituted or non-substituted aralkyl group, or a substituted or non-substituted heterocyclic group;
each X4 independently represents an oxygen atom, a substituted or non-substituted alkyl group, or an N—R5 group, wherein R5 represents a hydrogen atom, a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each R5 independently represents an oxygen atom, a C(CN)2 group, or a C═O group; and
M represents Fe, Co, Cu, Ni, or Zn;
wherein C represents a substituted or a non-substituted cyclic alkyl group;
each L independently represents a substituted or a non-substituted methine group;
each R6 independently represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X6 independently represents an oxygen atom, a CH2 group, or an N—R7 group, wherein R7 represents a substituted or a non-substituted C1-18 alkyl group;
each X7 independently represents an oxygen atom or a C(CN)2 group:
each X8 independently represents a substituted or a non-substituted alkylene group, or an a substituted or a non-substituted alkylene group containing an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
each m independently represents an integer of 0 or 1;
wherein each L′independently represent a substituted or a non-substituted methine group;
each R8 independently represents a hydrogen atom, a substituted or a non-substituted alkyl group, a substituted or a non-substituted aryl group, a substituted or a non-substituted aralkyl group, a substituted or a non-substituted heterocyclic ring, or a ferrocenyl group;
R9 represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X9 independently represents an oxygen atom, a CH2 group, or an N—R10 group, wherein R10 represents a substituted or a non-substituted C1-18 alkyl group;
each X10 independently represents an oxygen atom or a C(CN)2 group;
X11 represents a substituted or a non-substituted alkylene group, or a substituted or a non-substituted alkylene group containing an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
n is an integer of 0 or 1;
wherein each L″ independently represent a substituted or a non-substituted methine group:
each R11 independently represents a hydrogen atom, a substituted or a non-substituted alkyl group, a substituted or a non-substituted aryl group, a substituted or a non-substituted aralkyl group, or a substituted or a non-substituted heterocyclic ring;
R12 represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X12 independently represents an oxygen atom, a CH2 group, or an N—R13 group, wherein R13 represents a substituted or a non-substituted C1-18 alkyl group;
each X13 independently represents an oxygen atom or a C(CN)2 group;
each X14 independently represents a substituted or a non-substituted alkylene group, or a substituted or a non-substituted alkylene group containing an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
each k independently represents an integer of 0 or 1;
wherein each L′ independently represent a substituted or a non-substituted methine group;
R14 represents a substituted or a non-substituted C1-18 alkyl group, a substituted or a non-substituted C1-18 alkoxy group, a substituted or a non-substituted C1-18 carboxyl group, a substituted or a non-substituted C1-18 alkyl ester group, a substituted or a non-substituted arylester group, an adamantyl carbonyl group, an adamantyl group, or a substituted or a non-substituted aralkyl group;
each X15 independently represents an oxygen atom, a sulfur atom, a CH2 group, or an N—R15 group, wherein R15 represents a hydrogen atom or a substituted or a non-substituted C1-18 alkyl group;
each X16 independently represents an oxygen atom, a sulfur atom, or a C(CN)2 group;
X17 represents a substituted or a non-substituted alkylene group, or a substituted or a non-substituted alkylene group containing an oxygen atom, a sulfur atom, a selenium atom, or a nitrogen atom; and
n is an integer of 0 or 1.

### Claim 11 (depends on 10)

The method as claimed in claim 10, wherein the photoresist layer has a thickness of 30 nm to 200 nm.

### Claim 12 (depends on 10)

The method as claimed in claim 10, wherein the layered material comprises a substrate, and the substrate comprises crystalline silicon, quartz, silicon oxide, sapphire, aluminum nitride, gallium nitride, glass, polymer, or metal.

### Claim 13 (depends on 10)

The method as claimed in claim 10, wherein the layered material comprises an intermediate layer disposed between the substrate and the photoresist layer, the substrate comprises crystalline silicon, quartz, silicon oxide, sapphire, aluminum nitride, gallium nitride, glass, polymer, or metal, and the intermediate layer comprises aluminum oxide, aluminum nitride, silicon carbide, silicon oxide, zinc sulfide-silicon oxide, polymer, or metal.

### Claim 14 (depends on 10)

The method as claimed in claim 10, wherein the focused laser beam has a wavelength of 200 nm to 530 nm.