# US 2020/0401046 A1 · An ethynyl derived composite, a composition comprising thereof, a method for manufacturing a coating by it, and a method for manufacturing a device comprising the coating

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- Number: US 2020/0401046 A1
- Document ID: US20200401046A1
- Status: Published application
- Kind: A1
- Application number: 16/956,733
- Filed: 2018-12-17
- Published: 2020-12-24
- Earliest claimed: 2017-12-20
- Assignees: Merck Patent GmbH
- Applicants: Merck Patent GmbH
- Inventors: Shigemasa NAKASUGI; Yusuke HAMA; Hiroshi YANAGITA; Takashi SEKITO; Yuriko MATSUURA
- Web page: https://patentgrep.com/patent/US20200401046A1

## CPC

- G03F 7/094: {Multilayer resist systems, e.g. planarising layers}
- C08G 8/02: of ketones
- C08G 8/30: by unsaturated compounds, e.g. terpenes
- C09D 161/16: of ketones with phenols
- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take 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)
- 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)

## Abstract

[Problem to be Solved] An object is to provide a compound with good heat resistance. And another object is to provide a coating made exhibits less film shrinkage, good gap filling property and good planarization. [Solution] The present invention provides an ethynyl derived composite and a composition comprising thereof. And the present invention provides a method for manufacturing a coating by it, and a method for manufacturing a device.

## Claims

### Claim at position 1

-15. (canceled)

### Claim 16

An ethynyl derived composite comprising unit A and unit B, wherein unit A is represented by Formula (1),
Ar is C6-41 aromatic hydrocarbon ring
R1 is hydrogen, halogen, cyano, unsubstituted C1-6 alkyl, C1-6 alkyl substituted with at least one substituent selected from the group consisting of C1-6 alkyl, halogen and cyano, unsubstituted C3-20 aromatic ring, or C3-20 aromatic ring substituted with at least one substituent selected from the group consisting of C1-6 alkyl, halogen and cyano,
R2 and R3 are each independently hydrogen, halogen, cyano, unsubstituted C1-6 alkyl, C1-6 alkyl substituted with at least one substituent selected from the group consisting of C1-6 alkyl, halogen and cyano, unsubstituted C3-20 aromatic ring, or C3-20 aromatic ring substituted with at least one substituent selected from the group consisting of C1-6 alkyl, halogen and cyano,
R4 is C1-6 alkyl, halogen or cyano,
n1 is an integer, n1≥1,
n2 is 0, 1, 2, 3 or 4,
unit B is represented by Formula (2),
Cyclic Cy1 is a C5-6 alicyclic compound,
Ph1 and Ph2 are each independently C6-10 aromatic hydro carbon rings, which individually compose adjacent 2 carbons in cyclic Cy1,
R5 and R6 are each independently hydrogen, halogen, cyano, unsubstituted C1-6 alkyl, or C1-6 alkyl substituted with at least one substituent selected from halogen and cyano, the broken straight line is a direct bond bonding to the other portion of the ethynyl derived composite,
R7, R8 and R9 are each independently hydrogen, unsubstituted C1-6 alkyl, C1-6 alkyl substituted with at least one substituent selected from halogen or cyano, unsubstituted C6-16 aromatic hydro carbon, C6-16 aromatic hydro carbon substituted with at least one substituent selected from halogen or cyano, unsubstituted C1-6 alkylene linking to the other portion of the ethynyl derived composite, C1-6 alkylene substituted with at least one substituent selected from halogen or cyano linking to the other portion of the ethynyl derived composite, or a direct bond bonding to the other portion of the ethynyl derived composite,
n3 and n4 are each independently 0, 1, 2, 3 or 4, and
n5 is 0 or 1.

### Claim 17 (depends on 16)

The ethynyl derived composite according to claim 16, wherein P1 and P2 are each independently phenyl or naphthyl, and n3 and n4 are 0.

### Claim 18 (depends on 16)

The ethynyl derived composite according to claim 16, wherein
Ar is phenyl, naphthyl, fluorene, phenanthrene, perylene, or 9,9-diphenylfluorene,
R1, R2 and R3 is hydrogen,
n1 is 1 or 2, and
n2 is 0.

### Claim 19 (depends on 16)

A composition comprising the ethynyl derived composite according to claim 16, and a solvent.

### Claim 20 (depends on 19)

The composition according to claim 19, wherein the solvent comprises at least one solvent selected from the group consisting of water, hydrocarbon solvent, ether solvent, ester solvent, alcohol solvent, and ketone solvent.

### Claim 21 (depends on 19)

The composition according to claim 19, wherein the amount of the ethynyl derived composite is 2-60 mass % relative to the total amount of the composition.

### Claim 22 (depends on 19)

The composition according to claim 19, wherein a single or a plurality of solid components in the composition satisfy below Formula (3),
1.5≤{total number of atoms/(number of C−number of O)}≤3.5 Formula (3),
the number of C is the number of carbon atoms, and
the number of O is the number of oxygen atoms.

### Claim 23 (depends on 19)

The composition according to claim 19, further comprising at least one additive selected from the group consisting of a surfactant, a crosslinking agent, an acid generator, a radical generator, a high-carbon material, a photopolymerization initiator, and an agent for enhancing adhesion to substrates.

### Claim 24 (depends on 19)

The composition according to claim 19, further comprising at least one selected from the group consisting of a crosslinking agent in a concentration of 0-300,000 ppm, a photopolymerization initiator in a concentration of 0-100,000 ppm, an acid generator in a concentration of 0-50,000 ppm, and a radical generator in a concentration of 0-50,000 ppm.

### Claim 25 (depends on 19)

A resist underlayer forming composition consisting of the composition according to claim 19.

### Claim 26 (depends on 19)

A method for manufacturing a coating, comprising:
applying a layer of the composition according to claim 19 above a substrate; and
curing the layer to form the coating.

### Claim 27 (depends on 26)

The method for manufacturing a coating according to claim 26, wherein the conditions for curing the composition comprise irradiation with ultraviolet radiations having a wavelength of 10-380 nm.

### Claim 28 (depends on 26)

The method for manufacturing a coating according to claim 26, wherein the conditions for curing the composition comprise heating at 200-600 Celsius degree for 30-180 seconds.

### Claim 29 (depends on 26)

A method for manufacturing a device, comprising:
forming a coating by the method according to claim 26,
forming a layer of a photoresist composition above the coating;
curing the photoresist composition to form a photoresist layer;
exposing the substrate coated with the photoresist layer;
developing the exposed substrate to form a resist pattern;
etching with the resist pattern as a mask; and
processing the substrate.

### Claim 30 (depends on 29)

The method for manufacturing a device according to claim 29, further comprising forming wiring in the processed substrate.