# US 2019/0171107 A1 · Bottom antireflective coating forming composition

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- Number: US 2019/0171107 A1
- Document ID: US20190171107A1
- Status: Published application
- Kind: A1
- Application number: 16/324,299
- Filed: 2017-08-02
- Published: 2019-06-06
- Earliest claimed: 2016-08-09
- Assignees: Az Electronic Materials (Luxembourg) S.A.R.L.
- Applicants: AZ Electronic Materials (Luxembourg) S.a.r.l.
- Inventors: Hiroshi HITOKAWA; Tetsumasa TAKAICHI; Shunji KAWATO; Tomohide KATAYAMA
- Web page: https://patentgrep.com/patent/US20190171107A1

## CPC

- G03F 7/091: {characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement}
- C09D 125/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- G03F 7/16: Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74)
- G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G03F 7/30: Imagewise removal using liquid means
- 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)

## Abstract

[Problem to be Solved] To provide a bottom antireflective coating forming composition which can show high etching resistance and can be crosslinked even at a relatively low temperature. Further, to provide a resist pattern manufacturing method and a device manufacturing method using the same. [Solution] The bottom antireflective coating forming composition comprises: a polymer A comprising specific repeating units; a low molecular crosslinking agent having a molecular weight of 1 00 to 3,000; and a solvent. The resist pattern manufacturing method and the device manufacturing method using the same are also provided.

## Claims

### Claim at position 1

-14. (canceled)

### Claim 15

A bottom antireflective coating forming composition, comprising:
a polymer A comprising a repeating unit represented by formula (I) and a repeating unit represented by formula (II):
wherein
R1 is hydrogen, C1-6 alkyl, halogen, or cyano,
R2 is C1-6 alkyl, hydroxy, halogen, or cyano,
p is 0, 1, 2, 3, or 4,
R3 is hydrogen, C1-6 alkyl, halogen, or cyano,
R4 is C1-6 alkyl, halogen, or cyano, and
q is 0, 1, 2, 3, 4, or 5;
a low molecular crosslinking agent having a molecular weight of 100 to 3,000; and
a solvent.

### Claim 16 (depends on 15)

The bottom antireflective coating forming composition according to claim 15, wherein R1 is hydrogen, R2 is methyl or hydroxy, p is 0 or 1, R3 is hydrogen, R4 is methyl, and q is 0 or 1.

### Claim 17 (depends on 15)

The bottom antireflective coating forming composition according to claim 15, wherein in all the repeating units in the polymer A, the ratio of the repeating unit represented by formula (I) is 70 to 95 mol %, and the ratio of the repeating unit represented by formula (II) is 5 to 30 mol %.

### Claim 18 (depends on 16)

The bottom antireflective coating forming composition according to claim 16, wherein in all the repeating units in the polymer A, the ratio of the repeating unit represented by formula (I) is 70 to 95 mol %, and the ratio of the repeating unit represented by formula (II) is 5 to 30 mol %.

### Claim 19 (depends on 15)

The bottom antireflective coating forming composition according to claim 15, wherein the molecular weight of the low molecular crosslinking agent is 300 to 1,000.

### Claim 20 (depends on 18)

The bottom antireflective coating forming composition according to claim 18, wherein the molecular weight of the low molecular crosslinking agent is 300 to 1,000.

### Claim 21 (depends on 15)

The bottom antireflective coating forming composition according to claim 15, wherein in addition to the polymer A, the composition further comprises a polymer B comprising a repeating unit comprising an aromatic hydrocarbon ring in the main chain or the side chain.

### Claim 22 (depends on 20)

The bottom antireflective coating forming composition according to claim 20, wherein in addition to the polymer A, the composition further comprises a polymer B comprising a repeating unit comprising an aromatic hydrocarbon ring in the main chain or the side chain.

### Claim 23 (depends on 21)

The bottom antireflective coating forming composition according to claim 21, wherein the repeating unit of the polymer B is represented by formula (III), formula (IV), or formula (V):
wherein
Ar1 is a direct bond, C1-6 alkyl, or C6-14 aryl,
Ar2 is C6-14 aryl,
R5 and R6 are each independently C1-6 alkyl, hydroxy, halogen, or cyano,
r and s are each independently 0, 1, 2, 3, 4, or 5,
at least one of the C1, C2, and C3 rings each surrounded by the broken line is an aromatic hydrocarbon ring fused with the adjacent aromatic hydrocarbon ring P1, and
at least one of the C4, C5, and C6 rings each surrounded by the broken line is an aromatic hydrocarbon ring fused with the adjacent aromatic hydrocarbon ring P2;
wherein
X is a direct bond or C1-6 alkyl,
R7, R8, and R9 are each independently hydrogen, C1-6 alkyl, halogen, or cyano,
R10 is C1-6 alkyl, hydroxy, halogen, or cyano, and
t is 0, 1, 2, 3, 4, or 5;
wherein
Ar3 is unsubstituted or substituted C6-14 aryl, the substituent being C1-6 alkyl, hydroxyl, or carboxyl,
Ar4 is unsubstituted or substituted C6-14 aryl, the substituent being C1-6 alkyl, hydroxyl, or carboxyl, and
L1 and L2 are each independently a direct bond or C1-6 alkyl.

### Claim 24 (depends on 21)

The bottom antireflective coating forming composition according claim 21, wherein the weight average molecular weight (Mw) of the polymer A is 2,000 to 5,000, and the weight average molecular weight (Mw) of the polymer B is 800 to 12,000.

### Claim 25 (depends on 21)

The bottom antireflective coating forming composition according to claim 21, wherein the content of the polymer B and the content of the low molecular crosslinking agent are 0 to 200% by mass and 5 to 50% by mass, respectively, relative to the mass of the polymer A in the composition.

### Claim 26 (depends on 22)

The bottom antireflective coating forming composition according to claim 22, wherein the content of the polymer B and the content of the low molecular crosslinking agent are 0 to 200% by mass and 5 to 50% by mass, respectively, relative to the mass of the polymer A in the composition and the weight average molecular weight (Mw) of the polymer A is 2,000 to 5,000, and the weight average molecular weight (Mw) of the polymer B is 800 to 12,000.

### Claim 27 (depends on 15)

The bottom antireflective coating forming composition according to claim 15, wherein the solvent comprises ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, or a mixture thereof.

### Claim 28 (depends on 26)

The bottom antireflective coating forming composition according to claim 26, wherein the solvent comprises ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, or a mixture thereof.

### Claim 29 (depends on 15)

The bottom antireflective coating forming composition according to claim 15, wherein the composition further comprises a surfactant.

### Claim 30 (depends on 28)

The bottom antireflective coating forming composition according to claim 28, wherein the composition further comprises a surfactant.

### Claim 31 (depends on 15)

A resist pattern manufacturing method, comprising:
forming, on a substrate, a bottom antireflective coating from a bottom antireflective coating forming composition according to claim 15;
forming a photoresist coating on the bottom antireflective coating; and
exposing and developing the photoresist coating to form a resist pattern.

### Claim 32 (depends on 15)

A device manufacturing method, comprising:
forming, on a substrate, a bottom antireflective coating from a bottom antireflective coating forming composition according to claim 15;
forming a photoresist coating on the bottom antireflective coating;
exposing and developing the photoresist coating to form a resist pattern; and
forming a gap in the substrate or the layer on the substrate using the resist pattern as a mask.

### Claim 33 (depends on 31)

The device manufacturing method according to claim 31, wherein after forming the gap, the method further comprises contacting the resist pattern with water, a liquid mixture of a water-soluble organic solvent and water, or an alkali aqueous solution to thereby remove the resist pattern.

### Claim 34 (depends on 31)

The device manufacturing method according to claim 31, wherein the method further comprises forming wiring in the gap.