# US 2023/0056958 A1 · Photoresist developer and methods of use

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- Number: US 2023/0056958 A1
- Document ID: US20230056958A1
- Status: Published application
- Kind: A1
- Application number: 17/584,173
- Filed: 2022-01-25
- Published: 2023-02-23
- Earliest claimed: 2021-08-06
- Assignees: Taiwan Semiconductor Manufacturing Company, Ltd.
- Applicants: Taiwan Semiconductor Manufacturing Co., Ltd.
- Inventors: Tzu-Yang LIN; Chen-Yu LIU; Ching-Yu CHANG; Chin-Hsiang LIN
- Web page: https://patentgrep.com/patent/US20230056958A1

## CPC

- G03F 7/325: {Non-aqueous compositions}
- G03F 7/405: {Treatment with inorganic or organometallic reagents after imagewise removal}
- G03F 7/0048: {characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents}
- H10P 76/2041: {Photolithographic processes}
- 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)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

Novel photoresist developing compositions including a deprotonation agent, such as a nitrogen containing organic base capable of deprotonating a surface of portions of a photoresist layer exposed to radiation.

## Claims

### Claim 1

A lithography method, comprising:
forming a resist layer over a workpiece;
exposing the resist layer to radiation; and
exposing the resist layer to a developer that removes a portion of the resist layer, thereby forming a patterned resist layer, wherein the developer includes an organic solvent and a deprotonation agent.

### Claim 2 (depends on 1)

The lithography method of claim 1, further comprising deprotonating a proton containing group of the exposed resist layer.

### Claim 3 (depends on 2)

The lithography method of claim 2, wherein the deprotonation agent has a pKa between 5 and 20.

### Claim 4 (depends on 3)

The lithography method of claim 3, wherein the deprotonation agent is a nitrogen containing organic base.

### Claim 5 (depends on 4)

The lithography method of claim 4, wherein the deprotonation agent is pyridine, imidazole, benzimidazole, methylamine, histidine or methylethyl amine.

### Claim 6 (depends on 1)

The lithography method of claim 1, wherein the developer includes 10 wt % or more of the deprotonation agent.

### Claim 7 (depends on 1)

The lithography method of claim 1, wherein the exposing the resist layer to a developer is carried out at a temperature between 20° C. to 30° C.

### Claim 8 (depends on 1)

The lithography method of claim 1, wherein the exposing the resist layer to a developer is carried out for 5 to 300 seconds.

### Claim 9

A lithography method, comprising:
forming a resist layer over a workpiece;
exposing the resist layer to extreme ultraviolet radiation; and
altering a surface of a portion of the resist layer exposed to EUV radiation by contacting portions of the resist layer exposed to EUV radiation with a developer including an organic solvent and a nitrogen containing organic base; and
removing portions of the resist layer not exposed to EUV radiation.

### Claim 10 (depends on 9)

The lithography method of claim 9, wherein the resist layer has a thickness of 20 to 100 nm.

### Claim 11 (depends on 9)

The lithography method of claim 9, wherein the nitrogen containing organic base has a pKa between 5 and 20.

### Claim 12 (depends on 9)

The lithography method of claim 9, wherein the altering a surface of the resist layer exposed to EUV radiation includes converting a —COOH group at the surface of the resist layer exposed to the EUV radiation to a COO− group.

### Claim 13 (depends on 9)

The lithography method of claim 9, further comprising performing a baking process on the resist layer after the exposing.

### Claim 14 (depends on 9)

The lithography method of claim 9, further comprising processing the workpiece using the patterned resist layer as a mask.

### Claim 15 (depends on 9)

The lithography method of claim 9, wherein the nitrogen containing organic base is pyridine, imidazole, benzimidazole, methylamine, histidine or methylethyl amine.

### Claim 16 (depends on 9)

The lithography method of claim 9, wherein a pitch between exposed portions of the resist layer is less than 60 nm.

### Claim 17

A lithography developing composition including an organic solvent and a deprotonation agent which, when contacted with a resist layer which has been exposed to an electromagnetic radiation, causes solubility of the exposed resist layer in the lithography developing composition to decrease.

### Claim 18 (depends on 17)

The lithography developing composition of claim 17, wherein the deprotonation agent is a nitrogen containing organic base having a pKa between 5 and 20.

### Claim 19 (depends on 18)

The lithography developing composition of claim 18, the deprotonation agent is pyridine, imidazole, benzimidazole, methylamine, histidine or methylethyl amine.

### Claim 20 (depends on 17)

The lithography developing composition of claim 17, wherein the deprotonation agent is soluble in the organic solvent.