# US 2013/0280655 A1 · Aromatic hydrocarbon resin, underlayer film forming composition for lithography, and method for forming multilayer resist pattern

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- Number: US 2013/0280655 A1
- Document ID: US20130280655A1
- Status: Published application
- Kind: A1
- Application number: 13/976,611
- Filed: 2011-12-14
- Published: 2013-10-24
- Earliest claimed: 2010-12-28
- Assignees: Mitsubishi Gas Chemical Company, Inc.
- Inventors: Go Higashihara; Naoya Uchiyama; Masatoshi Echigo
- Web page: https://patentgrep.com/patent/US20130280655A1

## CPC

- C08G 8/10: with phenol
- C08G 8/00: Condensation polymers of aldehydes or ketones with phenols only
- C08G 14/04: with phenols
- C09D 161/34: Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09D161/04, C09D161/18 and C09D161/20
- G03F 7/004: Photosensitive materials (G03F7/12, G03F7/14 take precedence)
- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement}
- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- H10P 76/2043: {using an anti-reflective coating}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)
- 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

Provided is an aromatic hydrocarbon resin with a high carbon concentration and a low oxygen concentration that can be used as a coating agent or a resist resin for semiconductors, as well as a composition for forming an underlayer film for photolithography with excellent etching resistance as an underlayer film for a multilayer resist process, an underlayer film formed from the composition, and a method for forming a pattern using the underlayer film. An aromatic hydrocarbon, an aromatic aldehyde, and a phenol derivative are reacted in the presence of an acidic catalyst to yield an aromatic hydrocarbon resin with a high carbon concentration of 90 to 99.9 mass % and a solubility in propylene glycol monomethyl ether acetate of 10 mass % or more.

## Claims

### Claim 1

An aromatic hydrocarbon resin obtained by reacting an aromatic hydrocarbon represented by formula (1), an aldehyde represented by formula (2), and a phenol derivative represented by formula (3) in the presence of an acidic catalyst:
wherein in formula (1), R represents hydrogen or an alkyl group having 1 to 4 carbon atoms; 1 and m each represent a number from 1 to 3; A represents a number from 0 to 2; and plural groups represented by R are the same or different from each other;
wherein in formula (2), X represents hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, a cyclohexyl group, a hydroxyl group, a formyl group, or a carbonyl group; p and q each represent a number from 1 to 3; B represents a number from 0 to 2; and plural groups represented by X are the same or different from each other; and
wherein in formula (3), Y and Z represent hydrogen, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, or a cyclohexyl group; r and s each represent a number from 1 to 10; C represents a number from 0 to 2; and plural groups represented by Y and Z are the same or different from each other.

### Claim 2 (depends on 1)

The aromatic hydrocarbon resin according to claim 1, wherein the aromatic hydrocarbon represented by formula (1) is at least one selected from the group consisting of benzene, toluene, xylene, trimethylbenzene, naphthalene, methylnaphthalene, dimethylnaphthalene, and anthracene.

### Claim 3 (depends on 1)

The aromatic hydrocarbon resin according to claim 1, wherein the aldehyde represented by formula (2) is at least one selected from the group consisting of benzaldehyde, methylbenzaldehyde, ethylbenzaldehyde, propylbenzaldehyde, butylbenzaldehyde, cyclohexylbenzaldehyde, biphenylaldehyde, hydroxybenzaldehyde, dihydroxybenzaldehyde, naphthaldehyde, hydroxynaphthaldehyde, and anthracenealdehyde.

### Claim 4 (depends on 1)

The aromatic hydrocarbon resin according to claim 1, wherein the phenol derivative represented by formula (3) is at least one selected from the group consisting of phenol, catechol, resorcinol, hydroquinone, cresol, ethylphenol, propylphenol, butylphenol, methylcatechol, methylresorcinol, methylhydroquinone, anisole, naphthol, methylnaphthol, dihydroxynaphthalene, methyldihydroxynaphthalene, methoxynaphthalene, anthracenemonool, anthracenediol, anthracenetriol, and anthracenetetrol.

### Claim 5 (depends on 1)

The aromatic hydrocarbon resin according to claim 1, wherein the acidic catalyst is at least one selected from the group consisting of hydrochloric acid, sulfuric acid, phosphoric acid, oxalic acid, citric acid, formic acid, p-toluenesulfonic acid, methanesulfonic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, naphthalenesulfonic acid, naphthalenedisulfonic acid, zinc chloride, aluminum chloride, ferric chloride, borontrifluoride, silicotungstic acid, phosphotungstic acid, silicomolybdic acid, and phosphomolybdic acid.

### Claim 6 (depends on 1)

The aromatic hydrocarbon resin according to claim 1, comprising the structure represented by formula (4):
wherein in formula (4), R, X, Z, l, m, p, q, r, s, A, B, and C are all the same as in formulae (1), (2), and (3), and Y′ is the same as Y in formula (3) or is a single bond forming a direct bond with R, X, Y, Z, or an aromatic ring in the resin.

### Claim 7 (depends on 1)

The aromatic hydrocarbon resin according to claim 1, wherein the carbon concentration is from 80 to 99.9 mass %.

### Claim 8 (depends on 1)

The aromatic hydrocarbon resin according to claim 1, wherein the solubility in propylene glycol monomethyl ether acetate is 10 mass % or more.

### Claim 9 (depends on 1)

An underlayer film forming composition for lithography, the composition being for forming an underlayer film between a substrate and a resist layer and comprising at least the aromatic hydrocarbon resin according to claim 1 and an organic solvent.

### Claim 10 (depends on 9)

The underlayer film forming composition for lithography according to claim 9, further comprising an acid generator blended therein.

### Claim 11 (depends on 9)

The underlayer film forming composition for lithography according to claim 9, further comprising a crosslinking agent blended therein.

### Claim 12 (depends on 9)

An underlayer film for lithography formed from the underlayer film forming composition for lithography according to claim 9.

### Claim 13 (depends on 9)

A method for forming a multilayer resist pattern comprising the steps of forming an underlayer film on a substrate using the underlayer film forming composition according to claim 9, forming at least one photoresist layer on the underlayer film, subsequently forming a resist pattern by irradiating a predetermined region of the photoresist layer and developing the photoresist layer with an alkali, and subsequently transferring the resist pattern to the underlayer film by etching the underlayer film with plasma including at least oxygen gas while using the resist pattern as a mask.