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

Patent metadata

Field	Value
Publication number	US-11609498-B2
Application number	US-201816956733-A
Country	US
Kind code	B2
Filing date	Dec 17, 2018
Priority date	Dec 20, 2017
Publication date	Mar 21, 2023
Grant date	Mar 21, 2023

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.

First claim

The invention claimed is:

1. A polymer comprising unit A and unit B, wherein unit A is represented by Formula (1)′,

Cyclic Cy 2 is cyclopentane,
Ph 3 and Ph 4 are each independently C 6-10 aromatic hydrocarbon rings,
Ph 5 and Ph 6 are each independently C 6-10 aromatic hydrocarbon rings, which individually compose adjacent 2 carbons in cyclic Cy 2 ,
R 1 is hydrogen, halogen, cyano, unsubstituted C 1-6 alkyl, C 1-6 alkyl substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano, unsubstituted C 3-20 aromatic ring, or C 3-20 aromatic ring substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano,
R 2 and R 3 are each independently hydrogen, halogen, cyano, unsubstituted C 1-6 alkyl, C 1-6 alkyl substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano, unsubstituted C 3-20 aromatic ring, or C 3-20 aromatic ring substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano,
unit B is represented by Formula (2),

Cyclic Cy 1 is a C 5-6 alicyclic compound,
Ph 1 and Ph 2 are each independently C 6-10 aromatic hydrocarbon rings, which individually compose adjacent 2 carbons in cyclic Cy 1 ,
R 5 and R 6 are each independently hydrogen, halogen, cyano, unsubstituted C 1-6 alkyl, or C 1-6 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 polymer,
R 7 , R 8 and R 9 are each independently hydrogen, unsubstituted C 1-6 alkyl, C 1-6 alkyl substituted with at least one substituent selected from halogen or cyano, unsubstituted C 6-16 aromatic hydrocarbon, C 6-16 aromatic hydrocarbon substituted with at least one substituent selected from halogen or cyano, unsubstituted C 1-6 alkylene linking to the other portion of the ethynyl derived composite, C 1-6 alkylene substituted with at least one substituent selected from halogen or cyano linking to the other portion of the polymer, or a direct bond bonding to the other portion of the polymer,
n 3 and n 4 are each independently 0, 1, 2, 3 or 4, and
n 5 is 0 or 1 and
where the mol ratio of unit A and unit B in the polymer is 60:40-40:60.

2. The polymer according to claim 1 , wherein Ph 1 and Ph 2 are each independently phenyl or naphthyl, and n 3 and n 4 are 0.

3. The polymer according to claim 1 , wherein Ar is phenyl, naphthyl, fluorene, phenanthrene, perylene, or 9,9-diphenylfluorene,
R 1 , R 2 and R 3 is hydrogen,
n 1 is 1 or 2, and
n 2 is 0.

4. A composition comprising a polymer comprising unit A and unit B, wherein unit A is represented by Formula (1)′,

Cyclic Cy 2 is cyclopentane,
Ph 3 and Ph 4 are each independently C 6-10 aromatic hydrocarbon rings,
Ph 5 and Ph 6 are each independently C 6-10 aromatic hydrocarbon rings, which individually compose adjacent 2 carbons in cyclic Cy 2 ,
R 1 is hydrogen, halogen, cyano, unsubstituted C 1-6 alkyl, C 1-6 alkyl substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano, unsubstituted C 3-20 aromatic ring, or C 3-20 aromatic ring substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano,
R 2 and R 3 are each independently hydrogen, halogen, cyano, unsubstituted C 1-6 alkyl, C 1-6 alkyl substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano, unsubstituted C 3-20 aromatic ring, or C 3-20 aromatic ring substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano,
unit B is represented by Formula (2),

Cyclic Cy 1 is a C 5-6 alicyclic compound,
Ph 1 and Ph 2 are each independently C 6-10 aromatic-hydrocarbon rings, which individually compose adjacent 2 carbons in cyclic Cy 1 ,
R 5 and R 6 are each independently hydrogen, halogen, cyano, unsubstituted C 1-6 alkyl, or C 1-6 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 polymer,
R 7 , R 8 and R 9 are each independently hydrogen, unsubstituted C 1-6 alkyl, C 1-6 alkyl substituted with at least one substituent selected from halogen or cyano, unsubstituted C 6-16 aromatic hydrocarbon, C 6-16 aromatic hydrocarbon substituted with at least one substituent selected from halogen or cyano, unsubstituted C 1-6 alkylene linking to the other portion of the ethynyl derived composite, C 1-6 alkylene substituted with at least one substituent selected from halogen or cyano linking to the other portion of the polymer, or a direct bond bonding to the other portion of the polymer,
n 3 and n 4 are each independently 0, 1, 2, 3 or 4, and
n 5 is 0 or 1 and

where the mol ratio of unit A and unit B in the polymer is 60:40-40:60, and a solvent.

5. The composition according to claim 4 , 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.

6. The composition according to claim 4 , wherein the amount of the polymer is 2-60 mass % relative to the total amount of the composition and the amount of the organic solvents is 60-98 mass % relative to the total amount of the composition.

7. The composition according to claim 4 , 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.

8. The composition according to claim 4 , 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.

9. The composition according to claim 4 , 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, a radical generator in a concentration of 0-50,000 ppm and surfactant in the amount 0-5 mass % relative to the total amount of the composition.

10. A resist underlayer forming composition consisting of the composition according to claim 4 .

11. A method for manufacturing a coating, comprising:
applying a layer of the composition according to claim 4 above a substrate; and
curing the layer to form the coating.

12. The method for manufacturing a coating according to claim 11 , wherein the conditions for curing the composition comprise irradiation with ultraviolet radiations having a wavelength of 10-380 nm.

Assignees

• Merck Patent Gmbh

Inventors

• Nakasugi Shigemasa
• Hama Yusuke
• Yanagita Hiroshi
• Sekito Takashi
• Matsuura Yuriko

Classifications

• H10P76/2041

  Photolithographic processes · CPC title

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C08G8/30 Primary

  by unsaturated compounds, e.g. terpenes · CPC title

• C08G8/02

  of ketones · CPC title

• G03F7/00

  Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor (using photoresist structures for special production processes, see the relevant places, e.g. B44C, H10P76/00, H05K) · CPC title