# US 10,871,712 B2 · Stepped substrate-coating composition containing polyether resin having photocrosslinkable group

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- Number: US 10,871,712 B2
- Document ID: US10871712B2
- Status: Granted
- Kind: B2
- Application number: 16/500,626
- Filed: 2018-03-30
- Published: 2020-09-24
- Granted: 2020-12-22
- Earliest claimed: 2017-04-03
- Assignees: Nissan Chemical Corporation
- Applicants: Nissan Chemical Corporation
- Inventors: Hikaru Tokunaga; Takafumi Endo; Keisuke Hashimoto; Rikimaru Sakamoto
- Web page: https://patentgrep.com/patent/US10871712B2

## CPC

- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- C08F 290/14: Polymers provided for in subclass C08G
- C08G 65/4043: {(I) or (II) containing oxygen other than as phenol or carbonyl group}
- C09D 171/12: Polyphenylene oxides
- G03F 7/0388: {with ethylenic or acetylenic bands in the side chains of the photopolymer}
- G03F 7/162: {Coating on a rotating support, e.g. using a whirler or a spinner}
- G03F 7/168: {Finishing the coated layer, e.g. drying, baking, soaking}
- G03F 7/2037: {Exposure with X-ray radiation or corpuscular radiation, through a mask with a pattern opaque to that radiation}
- G03F 7/26: Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence)
- H10P 50/692: {characterised by their composition, e.g. multilayer masks or materials}
- H10P 76/2041: {Photolithographic processes}
- H10P 76/405: {characterised by their composition, e.g. multilayer masks}
- H10P 76/20: of masks comprising organic materials
- 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
- 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)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

A stepped substrate-coating composition having high properties of filling a pattern and capable of forming on a substrate a coating film that can be formed by photocuring, has flattening properties, and has high heat resistance after irradiation with light. A photocurable composition for coating a stepped substrate, the photocurable composition containing a polymer containing a unit structure of Formula (1): wherein A1, A2, and A3 are each independently an aromatic C6-100 ring optionally containing a heteroatom or a hydrocarbon group containing an aromatic C6-100 ring optionally containing a heteroatom, B1, B2, and B3 are each independently Formula (2): wherein R1 is a C1-10 alkylene group, a C1-10 alkenylene group, a C1-10 alkynylene group, a C6-40 arylene group, an oxygen atom, a carbonyl group, a sulfur atom, —C(O)—O—, —C(O)—NRa—, —NRb—, or a group including a combination thereof, R2 is a hydrogen atom or a C1-10 alkyl group.

## Claims

### Claim 1

A photocurable composition for coating a stepped substrate, the photocurable composition containing a polymer containing a unit structure of Formula (1):
[wherein A1, A2, and A3 are each independently an aromatic C6-100 ring optionally containing a heteroatom or a hydrocarbon group containing an aromatic C6-100 ring optionally containing a heteroatom, B1, B2, and B3 are each independently Formula (2):
(wherein R1 is a C1-10 alkylene group, a C1-10 alkenylene group, a C1-10 alkynylene group, a C6-40 arylene group (the alkylene group, the alkenylene group, the alkynylene group, and the arylene group are optionally substituted with one or two or more cyano groups and/or one or two or more hydroxyl groups), an oxygen atom, a carbonyl group, a sulfur atom, —C(O)—O—, —C(O)—NRa—, —NRb—, or a group including a combination thereof, Ra is a hydrogen atom or a C1-10 alkyl group, Rb is a hydrogen atom, a C1-10 alkyl group, or a C2-10 alkylcarbonyl group, R2 is a hydrogen atom or a C1-10 alkyl group, and a dotted line is a bond with A1, A2, or A3), X is a carbonyl group, a sulfonyl group, a —CR22— group, or a —C(CF3)2—group, n1 is an integer of 1 or more and 4 or less, n2 is an integer of 0 or more and 4 or less, n3 is an integer of 0 or more and 4 or less, and n1+n2+n3 is an integer of 1 to 12].

### Claim 2 (depends on 1)

The photocurable composition for coating a stepped substrate according to claim 1, wherein A1 is a polynuclear phenol of Formula (1-1) or (1-2):
(in Formulae (1-1) and (1-2), T1s are each independently a halogen group, a C1-10 alkyl group, a C6-18 aryl group, a C7-28 arylalkyl group, a C2-10 alkylcarbonyl group, a C2-10 alkylcarbonyloxy group, a C2-10 alkylcarbonylamino group, a C7-28 aryloxyalkyl group, a C1-6 alkoxy group, or an organic group including a combination thereof, q is an integer of 2 to 6, when q is 2, T2 is a single bond or a divalent C1-10 hydrocarbon group optionally having a hydroxyl group or a divalent C7-28 arylalkyl group optionally having a hydroxyl group, or when q is 3 to 6, T2 is a trivalent to hexavalent C1-10 hydrocarbon group optionally having a hydroxyl group or a trivalent to hexavalent C7-28 arylalkyl group optionally having a hydroxyl group, m is an integer of 1 to 7, n is an integer of 0 or more and 7-m or less, two T2s in Formula (1-2) optionally form a ring together, and p is an integer of 0 or 1), in which two hydroxyl groups among m×q hydroxyl groups are replaced by two bonds between A1 and two O atoms, and the rest of the m×q hydroxyl groups and/or a hydrogen atom in T2 are replaced by bonds between A1 and B1, provided that the total number of the bonds with B1 is n1.

### Claim 3 (depends on 1)

The photocurable composition for coating a stepped substrate according to claim 1, wherein A1 is a group derived from tri(hydroxyphenyl)methane, a group derived from tetrakis(hydroxyphenyl)ethane, or a group derived from tetrakis(hydroxyphenyl)-p-xylene, and A2 and A3 are a group derived from a benzene ring or a naphthalene ring.

### Claim 4 (depends on 1)

The photocurable composition for coating a stepped substrate according to claim 1, wherein X is a carbonyl group.

### Claim 5 (depends on 1)

The photocurable composition for coating a stepped substrate according to claim 1, wherein the photocurable composition is a polymer containing the unit structure of Formula (1), wherein n1 is 1 or 2 and n2 and n3 are 0.

### Claim 6 (depends on 1)

The photocurable composition for coating a stepped substrate according to claim 1, wherein the polymer containing the unit structure of Formula (1) further contains a unit structure of Formula (3):
(wherein A4 and A5 are each an aromatic C6-48 ring optionally containing a heteroatom or a hydrocarbon group containing an aromatic C6-48 ring optionally containing a heteroatom, B4 and B5 are the same groups as B1, B2, and B3 in Formula (2) described above, n4 is an integer of 1 or more and 4 or less, n5 is an integer of 0 or more and 4 or less, and n4+n5 is an integer of 1 to 8).

### Claim 7 (depends on 1)

The photocurable composition for coating a stepped substrate according to claim 1, wherein the polymer containing the unit structure of Formula (1) or the unit structures of Formulae (1) and (3) further contains a unit structure of Formula (1′), wherein in Formula (1), n1 is 0, n2 is 0, and n3 is 0.

### Claim 8 (depends on 1)

The photocurable composition for coating a stepped substrate according to claim 1, which is a resist underlayer film-forming composition used in a lithography process in manufacturing of a semiconductor device.

### Claim 9 (depends on 1)

A method for manufacturing a coating substrate comprising a step (i) of applying the photocurable composition for coating a stepped substrate according to claim 1 to a stepped substrate, and a step (ii) of exposing the photocurable composition for coating a stepped substrate.

### Claim 10 (depends on 9)

The method for manufacturing a coating substrate according to claim 9, further comprising a step (ia) of heating the substrate at a temperature of 70 to 400° C. for 10 seconds to 5 minutes after the photocurable composition for coating a stepped substrate is applied in the step (i).

### Claim 11 (depends on 9)

The method for manufacturing a coating substrate according to claim 9, wherein a wavelength of exposure light in the step (ii) is 150 nm to 248 nm.

### Claim 12 (depends on 9)

The method for manufacturing a coating substrate according to claim 9, wherein an exposure dose in the step (ii) is 10 mJ/cm2 to 3,000 mJ/cm2.

### Claim 13 (depends on 9)

The method for manufacturing a coating substrate according to claim 9, wherein the substrate has an open area (unpatterned area) and a pattern area including dense (DENCE) and crude (ISO) patterns, and an aspect ratio of the patterns is 0.1 to 10.

### Claim 14 (depends on 13)

The method for manufacturing a coating substrate according to claim 13, wherein a difference in level of coating (Bias) between the open area and the pattern area is 1 to 50 nm.

### Claim 15 (depends on 1)

A method for manufacturing a semiconductor device comprising the steps of forming an underlayer film from the composition for coating a stepped substrate according to claim 1 on a stepped substrate, forming a resist film on the underlayer film, irradiating the resist film with light or an electron beam, followed by development, to form a resist pattern, etching the underlayer film through the resist pattern, and processing a semiconductor substrate through the patterned underlayer film.

### Claim 16 (depends on 1)

A method for manufacturing a semiconductor device comprising the steps of forming an underlayer film from the photocurable composition for coating a stepped substrate according to claim 1 on a stepped substrate, forming a hard mask on the underlayer film, forming a resist film on the hard mask, irradiating the resist film with light or an electron beam, followed by development, to form a resist pattern, etching the hard mask through the resist pattern, etching the underlayer film through the patterned hard mask, and processing a semiconductor substrate through the patterned underlayer film.