# US 11,906,901 B2 · Alternating copolymer chain scission photoresists

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- Number: US 11,906,901 B2
- Document ID: US11906901B2
- Status: Granted
- Kind: B2
- Application number: 17/340,300
- Filed: 2021-06-07
- Published: 2022-12-08
- Granted: 2024-02-20
- Earliest claimed: 2021-06-07
- Assignees: International Business Machines Corporation
- Applicants: International Business Machines Corporation
- Inventors: Dario Goldfarb; Ekmini Anuja De Silva; Jing Guo; Jennifer Church; Luciana Meli
- Web page: https://patentgrep.com/patent/US11906901B2

## CPC

- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- C07F 7/2224: {Compounds having one or more tin-oxygen linkages}
- G03F 7/0042: {with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence)}
- G03F 7/0043: {Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof (G03F7/0044 takes precedence)}
- G03F 7/2004: {characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light}
- 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)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Alternating copolymers having hydrocarbon-substituted terminal units and repeat units each containing two different monomer units with extreme ultraviolet (EUV)-absorbing elements are disclosed. Alternating copolymers having organic terminal units and repeat units each containing a monomer unit with an EUV-absorbing element and an organic monomer unit are also disclosed. A process of forming a polymer resist, which includes providing an alternating copolymer having repeat units with at least one EUV-absorbing monomer unit and replacing end groups of the alternating copolymer with unreactive terminal units, is disclosed as well.

## Claims

### Claim 1

A process of forming a polymer resist, comprising:
providing an alternating copolymer having repeat units each comprising an ultraviolet (EUV)-absorbing element A; and
reacting end groups of the alternating copolymer with monofunctional monomers selected from the group consisting of trimethyltin hydride, triethyltin hydride, tripropyltin hydride, tributyltin hydride, triphenyltin hydride, trimethyltin diethylamide, triethyltin diethylamide, tripropyltin diethylamide, tri-n-butyltin diethylamide, tri-t-butyltin diethylamide, trimethyltellurium iodide, tetraphenylantimony bromide, tetra-m-tolylbismuth iodide, and tetramethylbismuth chloride to form a polymer having the following structure:
wherein:
n is an integer greater than 1
x=2 or 3; and
R, R′, R″, and R′″ are each hydrocarbon ligands.

### Claim 2 (depends on 1)

The process of claim 1, wherein the providing comprises a polymerization reaction between two different species of difunctional EUV-absorbing monomers.

### Claim 3 (depends on 1)

The process of claim 1, further comprising:
applying the polymer resist on a substrate; and
lithographically patterning the polymer resist.

### Claim 4 (depends on 1)

The process of claim 1, wherein R is not the same species of hydrocarbon as R′.

### Claim 5 (depends on 1)

The process of claim 1, wherein A is selected from the group consisting of Sn, Te, Bi, and Sb.

### Claim 6 (depends on 1)

The process of claim 1, wherein the R″ is the same species of hydrocarbon as the R′.

### Claim 7 (depends on 1)

The process of claim 1, wherein the R is the same species of hydrocarbon as the R′″.

### Claim 8 (depends on 1)

The process of claim 1, wherein the R″ is the same species of hydrocarbon as the R′″.

### Claim 9 (depends on 1)

The process of claim 1, wherein a chain length of the polymer is controlled by the reacting the end groups with the monofunctional monomers.