# US 10,372,040 B2 · Resist underlayer film forming composition for lithography containing hydrolyzable silane having halogen-containing carboxylic acid amide group

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- Number: US 10,372,040 B2
- Document ID: US10372040B2
- Status: Granted
- Kind: B2
- Application number: 15/533,237
- Filed: 2015-12-04
- Published: 2017-11-09
- Granted: 2019-08-06
- Earliest claimed: 2014-12-08
- Assignees: Nissan Chemical Industries, Ltd.
- Applicants: Nissan Chemical Industries, Ltd.
- Inventors: Wataru Shibayama; Kenji Takase; Rikimaru Sakamoto
- Web page: https://patentgrep.com/patent/US10372040B2

## CPC

- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- C08G 16/00: Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 (with polynitriles C08G69/38)
- C08L 83/04: Polysiloxanes
- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C09D 161/00: Coating compositions based on condensation polymers of aldehydes or ketones (with polyalcohols C09D159/00; with polynitriles C09D177/00); Coating compositions based on derivatives of such polymers
- C09D 165/00: Coating compositions based on macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain (C09D107/00 - C09D157/00, C09D161/00 take precedence); Coating compositions based on derivatives of such polymers
- C09D 183/04: Polysiloxanes
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- C09D 183/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- 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 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- G03F 7/0752: {in non photosensitive layers or as additives, e.g. for dry lithography}
- G03F 7/168: {Finishing the coated layer, e.g. drying, baking, soaking}
- G03F 7/2004: {characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light}
- G03F 7/26: Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence)
- G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- H10P 50/287: {by chemical means}
- H10P 50/692: {characterised by their composition, e.g. multilayer masks or materials}
- H10P 50/695: {characterised by the process involved to create the mask, e.g. lift-off masks or sidewalls or to modify the mask}
- H10P 50/73: {using masks for insulating materials}
- H10P 76/2041: {Photolithographic processes}
- C08G 73/0672: {with only one nitrogen atom in the ring}
- C08G 77/24: halogen-containing groups
- C08G 77/26: nitrogen-containing groups
- C08G 2261/135: Cross-linked structures
- C08G 2261/3142: fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene
- C08G 2261/3241: containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
- C08G 2261/76: crosslinking
- G03F 7/162: {Coating on a rotating support, e.g. using a whirler or a spinner}
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON 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

A resist underlayer film forming composition for lithography that can be used as a hard mask. The composition can improve pattern resolution due to having a trihalogenoacetamide skeleton. A resist underlayer film forming composition for lithography comprising a hydrolyzable silane, a hydrolysis product thereof, a hydrolysis condensate thereof, or a combination thereof as a silane, wherein the hydrolyzable silane comprises a silane having a halogen-containing carboxylic acid amide group.

## Claims

### Claim 1

A resist underlayer film forming composition for lithography comprising: a hydrolyzable silane, a hydrolysis product thereof, a hydrolysis condensate thereof, or a combination thereof as a silane, wherein
the hydrolyzable silane comprises a hydrolyzable silane having a trifluoroacetamide group.

### Claim 2 (depends on 1)

The resist underlayer film forming composition according to claim 1, wherein the hydrolyzable silane having a trifluoroacetamide group is a hydrolyzable silane of Formula (1):
R1aR2bSi(R3)4−(a+b) Formula (1)
in Formula (1),
R1 is an organic group of Formula (2):
in Formula (2),
R4 is an organic group optionally having an amide group, an amino group, an ether group, or a sulfonyl group and the organic group is a C1-10 alkylene group, an arylene group, or a combination thereof,
R5 is a hydrogen atom, and
R6 is a trifluoromethyl group,
and is bonded to a silicon atom through a Si—C bond;
R2 is an organic group having an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkoxyaryl group, an alkenyl group, or an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, an amino group, or a cyano group and is bonded to a silicon atom through a Si—C bond;
R3 is an alkoxy group, an acyloxy group, or a halogen group; and
a is an integer of 1, b is an integer of 0 to 2, and a+b is an integer of 1 to 3.

### Claim 3 (depends on 1)

The resist underlayer film forming composition according to claim 1, wherein the hydrolyzable silane is a combination of the hydrolyzable silane of Formula (1) and other hydrolyzable silane, and the other hydrolyzable silane is at least one hydrolyzable silane selected from the group consisting of
a hydrolyzable silane of Formula (3):
R7cSi(R8)4−c Formula (3)
in Formula (3), R7 is an organic group having an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkoxyaryl group, an alkenyl group, or an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, or a cyano group and is bonded to a silicon atom through a Si—C bond; R8 is an alkoxy group, an acyloxy group, or a halogen group; and c is an integer of 0 to 3, and
a hydrolyzable silane of Formula (4):
R9dSi(R10)3−d2Ye Formula (4)
in Formula (4), R9 is an alkyl group and is bonded to a silicon atom through a Si—C bond; R10 is an alkoxy group, an acyloxy group, or a halogen group; Y is an alkylene group or an arylene group; d is an integer of 0 or 1; and e is an integer of 0 or 1.

### Claim 4 (depends on 1)

The resist underlayer film forming composition according to claim 1, wherein the resist underlayer film forming composition comprises a hydrolysis condensate of a hydrolyzable silane made of a combination of the hydrolyzable silane of Formula (1)
R1aR2bSi(R3)4−(a+b) Formula (1)
in Formula (1), R1 is an organic group of Formula (2), and the hydrolyzable silane of Formula (3)
R7cSi(R8)4−c Formula (3)
in Formula (3), R7 is an organic group having an alkyl group, an aryl group, a halogenated alkyl group, a halogenated aryl group, an alkoxyaryl group, an alkenyl group, or an epoxy group, an acryloyl group, a methacryloyl group, a mercapto group, or a cyano group and is bonded to a silicon atom through a Si—C bond; R8 is an alkoxy group, an acyloxy group, or a halogen group; and c is an integer of 0 to 3,
as a polymer.

### Claim 5 (depends on 1)

The resist underlayer film forming composition according to claim 1, further comprising an acid.

### Claim 6 (depends on 1)

The resist underlayer film forming composition according to claim 1, further comprising water.

### Claim 7 (depends on 1)

The resist underlayer film forming composition according to claim 1, further comprising an organic polymer compound having a weight average molecular weight of 10,000 to 100,000.

### Claim 8 (depends on 7)

The resist underlayer film forming composition according to claim 7, wherein the organic polymer compound is one or more polymers selected from the group consisting of polyesters, polystyrenes, polyimides, acrylic polymers, methacrylic polymers, polyvinyl ethers, phenol novolacs, naphthol novolacs, polyether, polyamides, and polycarbonates.

### Claim 9 (depends on 7)

The resist underlayer film forming composition according to claim 7, wherein the organic polymer compound comprises an aromatic ring structure selected from the group consisting of a benzene ring, a naphthalene ring, an anthracene ring, a triazine ring, a quinoline ring, and a quinoxaline ring.

### Claim 10 (depends on 7)

The resist underlayer film forming composition according to claim 7, wherein the organic polymer compound comprises hydroxy groups.

### Claim 11 (depends on 1)

A resist underlayer film formed on a semiconductor substrate and made of a cured product of the resist underlayer film forming composition as claimed in claim 1.

### Claim 12 (depends on 1)

A method for manufacturing a semiconductor device, the method comprising:
applying the resist underlayer film forming composition as claimed in claim 1 onto a semiconductor substrate and baking the applied composition to form a resist underlayer film;
applying a resist composition onto the resist underlayer film to form a resist film;
exposing the resist film to light;
developing the resist film after exposure to obtain a resist pattern;
etching the resist underlayer film using the resist pattern; and
processing the semiconductor substrate using the patterned resist film and resist underlayer film.

### Claim 13 (depends on 1)

A method for manufacturing a semiconductor device, the method comprising:
forming an organic underlayer film on a semiconductor substrate;
applying a resist underlayer film forming composition according to claim 1 onto the organic underlayer film and baking the applied composition to form a resist underlayer film;
applying a resist composition onto the resist underlayer film to form a resist film;
exposing the resist film to light;
developing the resist film after exposure to obtain a resist pattern;
etching the resist underlayer film using the resist pattern;
etching the organic underlayer film using the patterned resist underlayer film; and
processing the semiconductor substrate using the patterned organic underlayer film.