# US 2013/0157196 A1 · Composition for forming a developable bottom antireflective coating

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

- Number: US 2013/0157196 A1
- Document ID: US20130157196A1
- Status: Published application
- Kind: A1
- Application number: 13/327,030
- Filed: 2011-12-15
- Published: 2013-06-20
- Earliest claimed: 2011-12-15
- Assignees: AZ Electronic Materials USA Corp.
- Inventors: Shigemasa Nakasugi; Kazuma Yamamoto; Yasushi Akiyama; Shinji Miyazaki; Munirathna Padmanaban; Srinivasan Chakrapani
- Web page: https://patentgrep.com/patent/US20130157196A1

## CPC

- G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- C09D 135/00: Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least another carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Coating compositions based on derivatives of such polymers
- G03C 1/73: containing organic compounds
- G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement}
- C08K 5/1535: Five-membered rings
- C08K 5/3415: Five-membered rings
- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- G03F 7/095: having more than one photosensitive layer (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)
- 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)
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

The present invention provides a composition for forming a bottom anti-reflective coating, and also provides a photoresist pattern formation method employing that composition. The composition gives a bottom anti-reflective coating used in a lithographic process for manufacturing semiconductor devices, and the coating can be developed with a developing solution for photoresist. The composition contains a solvent, a polymer having a condensed polycyclic aromatic group, and a compound having a maleimide derivative or a maleic anhydride derivative. The composition may further contain a photo acid generator or a crosslinking agent.

## Claims

### Claim 1

A composition for forming a bottom anti-reflective coating, comprising
a solvent,
a polymer represented by the following formula (1):
-Am-Bn- (1)
in which
A and B are repeating units represented by the following formulas (A) and (B), respectively:
wherein
each of R11 and R12 is independently hydrogen or an alkyl group;
L′1 is a single bond, COO or a straight- or branched chain alkylene containing one or more carbon atoms;
Y is a condensed polycyclic aromatic group containing two or more benzene rings; and
Z is a group selected from the group consisting of R3COOR4 and R3OR4, provided that R3 is a single bond, oxygen or a straight- or branched chain alkylene which may have a fluorine atom and which contains one or more carbon atoms and also provided that R4 is hydrogen or a substituted or non-substituted hydrocarbon group; each of m and n is a number indicating the polymerization degree provided that m is not less than 10 and n is not less than 0;
and,
a compound comprising a maleimide or anhydride.

### Claim 2 (depends on 1)

The composition according to claim 1, where Y is a condensed polycyclic aromatic group containing two or more benzene rings provided that one of the benzene rings is replaced with a quinine ring and that the condensed polycyclic aromatic group may optionally have a substituent selected from the group consisting of alkyl, aryl, halogen, alkoxy, nitro, aldehyde, cyano, amido, dialkylamino, sulfonamido, imido, carboxy, carboxylic acid ester, sulfo, sulfonic acid ester, alkylamino, and arylamino.

### Claim 3 (depends on 1)

The composition according to claim 1, where the compound is represented by any of the following formulas (2) to (4):
in which each of R21, R22 and R23 is independently a group selected from the group consisting of hydrogen, alkyl, aryl, halogen atom, alkoxy, nitro, aldehyde, cyano, amido, dialkylamino, sulfonamido, imido, carboxylic acid, carboxylic acid ester, sulfonic acid, sulfonic acid ester, alkylamino, and arylamino;
in which each of R31 to R36 is independently a group selected from the group consisting of hydrogen, alkyl, aryl, halogen, alkoxy, nitro, aldehyde, cyano, amido, dialkylamino, sulfonamido, imido, carboxylic acid, carboxylic acid ester, sulfonic acid, sulfonic acid ester, alkylamino, and arylamino; and L31 is an alykylene or an arylene;
and
in which each of R41 and R42 is independently a group selected from the group consisting of hydrogen, alkyl, aryl, halogen atom, alkoxy, nitro, aldehyde, cyano, amido, dialkylamino, sulfonamido, imido, carboxylic acid, carboxylic acid ester, sulfonic acid, sulfonic acid ester, alkylamino, and arylamino.

### Claim 4 (depends on 2)

The composition according to claim 2, comprising the compound represented by the formula (3).

### Claim 5 (depends on 1)

The composition according to claim 1, further comprising a photo acid generator.

### Claim 6 (depends on 1)

The composition according to claim 1, further comprising a crosslinking agent.

### Claim 7 (depends on 1)

The composition according to claim 1,
wherein
each of R11 and R12 is independently hydrogen or methyl,
L11 is COO, and
Z is R3COOR4, provided that R3 is a single bond or a straight chain alkylene group having 1 to 6 carbon atoms and that R4 is hydrogen or a branched chain alkyl group having 1 to 10 carbon atoms.

### Claim 8 (depends on 2)

A bottom anti-reflective coating formed on a substrate the composition of claim 2 and then heating for forming a bottom anti-reflective coating.

### Claim 9 (depends on 8)

The bottom anti-reflective coating according to claim 8, formed by a heat-induced Diels-Alder reaction between the polymer represented by the formula (1) and the compound represented by any of the formulas (2) to (4).

### Claim 10 (depends on 1)

A pattern formation method comprising the steps of:
spreading the composition according to claim 1 for forming a bottom anti-reflective coating on a semiconductor substrate and then baking, to form a bottom anti-reflective coating;
forming a photoresist layer on the bottom anti-reflective coating;
exposing to light the semiconductor substrate covered with the bottom anti-reflective coating and the photoresist layer; and after the exposure,
developing them by use of a developing solution selected from the group consisting of alkaline developing solution and organic solvent, thereby forming a pattern in the photoresist and the antireflective coating.

### Claim 11 (depends on 10)

The pattern formation method according to claim 10, wherein the photoresist layer is a positive-working photoresist, R4 is hydrogen, and the developing solution is an alkaline aqueous solution.

### Claim 12 (depends on 10)

The pattern formation method according to claim 10, wherein the photoresist layer is made of a positive-working photoresist, R4 is a substituted or non-substituted hydrocarbon group, and the developing solution is an alkaline aqueous solution.

### Claim 13 (depends on 12)

The pattern formation method according to claim 12, wherein the composition for forming a bottom anti-reflective coating further contains a photo acid generator.

### Claim 14 (depends on 10)

The pattern formation method according to claim 10, wherein the photoresist layer is a negative-working photoresist, R4 is hydrogen, and the developing solution is an alkaline aqueous solution.

### Claim 15 (depends on 14)

The pattern formation method according to claim 14, wherein the composition for forming a bottom anti-reflective coating further contains a photo acid generator.

### Claim 16 (depends on 14)

The pattern formation method according to claim 14, wherein the composition for forming a bottom anti-reflective coating further contains a crosslinking agent.

### Claim 17 (depends on 10)

The pattern formation method according to claim 10, wherein the photoresist layer is a positive-working photoresist, R4 is a substituted or non-substituted hydrocarbon group, and the developing solution is an organic solvent.

### Claim 18 (depends on 17)

The pattern formation method according to claim 17, wherein the composition for forming a bottom anti-reflective coating further contains a photo acid generator.

### Claim 19 (depends on 10)

The pattern formation method according to claim 10, wherein the exposure is carried out by use of light in the wavelength range of 13.5 to 248 nm.

### Claim 20 (depends on 1)

A pattern formation method comprising the steps of:
spreading the composition according to claim 1 for forming a bottom anti-reflective coating on a semiconductor substrate and then baking, to form a bottom anti-reflective coating;
forming a photoresist layer on the bottom anti-reflective coating;
exposing to light the semiconductor substrate covered with the bottom anti-reflective coating and the photoresist layer; and
after the exposure,
developing them by use of a developing solution selected from the group consisting of alkaline developing solutions and organic solvents, thereby forming a pattern in the photoresist and not in the antireflective coating.