# US 9,040,225 B2 · Developable bottom antireflective coating composition and pattern forming method using thereof

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 9,040,225 B2
- Document ID: US9040225B2
- Status: Granted
- Kind: B2
- Application number: 14/527,813
- Filed: 2014-10-30
- Published: 2015-02-19
- Granted: 2015-05-26
- Earliest claimed: 2012-06-29
- Assignees: International Business Machines Corporation
- Applicants: International Business Machines Corporation
- Inventors: Kuang-Jung Chen; Steven J. Holmes; Wu-Song Huang; Ranee W. Kwong; Sen Liu
- Web page: https://patentgrep.com/patent/US9040225B2

## CPC

- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- C08F 220/26: Esters containing oxygen in addition to the carboxy oxygen
- C08L 33/066: {containing -OH groups}
- C08L 33/16: Homopolymers or copolymers of esters containing halogen atoms
- C09D 133/066: {containing -OH groups}
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/038: Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021)
- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement}
- G03F 7/30: Imagewise removal using liquid means
- G03F 7/322: {Aqueous alkaline compositions}
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- H10P 30/20: into semiconductor materials, e.g. for doping
- H10P 76/2041: {Photolithographic processes}
- H10P 76/2043: {using an anti-reflective coating}
- C08L 2312/00: Crosslinking
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

The present invention relates to a developable bottom antireflective coating (BARC) composition and a pattern forming method using the BARC composition. The BARC composition includes a first polymer having a first carboxylic acid moiety, a hydroxy-containing alicyclic moiety, and a first chromophore moiety; a second polymer having a second carboxylic acid moiety, a hydroxy-containing acyclic moiety, and a second chromophore moiety; a crosslinking agent; and a radiation sensitive acid generator. The first and second chromophore moieties each absorb light at a wavelength from 100 nm to 400 nm. In the patterning forming method, a photoresist layer is formed over a BARC layer of the BARC composition. After exposure, unexposed regions of the photoresist layer and the BARC layer are selectively removed by a developer to form a patterned structure in the photoresist layer. The BARC composition and the pattern forming method are especially useful for implanting levels.

## Claims

### Claim 1

A method of forming a patterned material structure on a substrate, the method comprising:
providing a substrate with a layer of the material;
applying a BARC composition to the substrate to form a BARC layer over the material layer, the BARC composition comprising: a first polymer comprising a first carboxylic acid moiety, a hydroxy-containing alicyclic moiety, and a first chromophore moiety which absorbs light at a wavelength selected from a range from 100 nm to 400 nm; a second polymer comprising a second carboxylic acid moiety, a hydroxy-containing acyclic moiety, and a second chromophore moiety which absorbs light at a wavelength selected from a range from 100 nm to 400 nm; a crosslinking agent; joining the first polymer and the second polymer and a radiation sensitive acid generator;
forming a photoresist layer over the BARC layer;
patternwise exposing the photoresist layer to radiation; and
developing the substrate with a developer, whereby unexposed portions of the photoresist layer and the BARC layer are selectively removed by the developer to form a patterned structure in the photoresist layer.

### Claim 2 (depends on 1)

The method of claim 1, wherein the first carboxylic acid moiety and the second carboxylic acid moiety are each independently selected from the group consisting of an acrylic acid monomer unit, a methacrylic acid monomer unit, a 4-vinylbenzoic acid monomer unit, a 2-carboxyethyl acrylate monomer unit, a 2-carboxyethyl methacrylate monomer unit, a mono-2-(methacryloyloxy)ethyl succinate monomer unit, and a mono-2-(acryloyloxy)ethyl succinate monomer unit.

### Claim 3 (depends on 1)

The method of claim 1, wherein the hydroxy-containing alicyclic moiety includes an adamantyl group.

### Claim 4 (depends on 1)

The method of claim 1, wherein the hydroxy-containing acyclic moiety is a monomer unit derived from a monomer selected from the group consisting of the following structures:
wherein s represents a positive integer from 1 to 30; R is a saturated carbon chain having a total number of carbon atoms from 1 to 30.

### Claim 5 (depends on 1)

The method of claim 1, wherein the first chromophore moiety and the second chromophore moiety each includes an aromatic group.

### Claim 6 (depends on 1)

The method of claim 1, further comprising at least one of a solvent, a quencher, and a surfactant.

### Claim 7 (depends on 6)

The method of claim 6, wherein the BARC composition comprises:
about 0.1 to about 29 wt. % of the first polymer;
about 0.1 to about 29 wt. % of the second polymer;
about 0.1 to about 30 wt. % of the crosslinking agent, based on the total weight of the first and second polymers;
about 0.1 to about 30 wt. % of the radiation sensitive acid generator, based on the total weight of the first and second polymers; and
about 70 to about 99.9 wt. % of the solvent.

### Claim 8 (depends on 7)

The method of claim 7, wherein the weight percentage of the first polymer is higher than the weight percentage of the second polymer.

### Claim 9 (depends on 1)

The method of claim 1, wherein the photoresist layer is a negative photoresist.

### Claim 10 (depends on 9)

The method of claim 9, wherein the developer is an aqueous alkaline developer.

### Claim 11 (depends on 1)

The method of claim 1, further comprising:
transferring the patterned structure to the material layer.

### Claim 12 (depends on 11)

The method of claim 11, wherein the patterned structure is transferred by ion implantation to form a pattern of ion implanted material in the material layer.