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-11914296-B2
Application number	US-202318113089-A
Country	US
Kind code	B2
Filing date	Feb 23, 2023
Priority date	Dec 20, 2017
Publication date	Feb 27, 2024
Grant date	Feb 27, 2024

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 synthesis method of an ethynyl derived composite comprising;
Reacting components

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;
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 hydro carbon, C 6-16 aromatic hydro carbon 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 ethynyl derived composite, or a direct bond bonding to the other portion of the ethynyl derived composite;
n 3 and n 4 are each independently 0, 1, 2, 3 or 4;
n 5 is 0 or 1;
Ar is each independently C 6-41 aromatic hydrocarbon ring;
R 4 is each independently C 1-6 alkyl, halogen or cyano;
n 1 is 1, 2, 3 or 4; and
n 2 is 0, 1, 2, 3 or 4;
and obtain a precursor, and
Replacing hydroxyl group with a group derived from ethynyl;
where the synthesized ethynyl derived composite is a polymer.

2. The synthesis method according to claim 1 , where the ethynyl composite is described as below formula

wherein
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;
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 hydro carbon, C 6-16 aromatic hydro carbon 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 ethynyl derived composite, or a direct bond bonding to the other portion of the ethynyl derived composite;
n 3 and n 4 are each independently 0, 1, 2, 3 or 4;
n 5 is 0 or 1;
Ar is each independently C 6-41 aromatic hydrocarbon ring;
R 4 is each independently C 1-6 alkyl, halogen or cyano;
n 1 is 1, 2, 3 or 4;
n 2 is 0, 1, 2, 3 or 4;
R 1 is 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;
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; and
the broken straight line is a direct bond bonding to the other portion of the ethynyl derived composite.

3. The synthesis method according to claim 1 ; where the group derived from ethynyl to replace hydroxyl is represented by below formula;

wherein R 1 is 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;
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 3-2 u aromatic ring substituted with at least one substituent selected from the group consisting of C 1-6 alkyl, halogen and cyano.

4. The synthesis method according to claim 2 ; where
Ph 1 and Ph 2 are each independently phenyl or naphthyl;
n 3 and n 4 are 0;
Ph 3 , Ph 4 , Ph 5 and Ph 6 are each independently phenyl or naphthyl; or
R 1 , R 2 and R 3 are hydrogen.

5. The synthesis method according to claim 1 , where the main chain of the synthesized polymer has none or few secondary carbon and the tertiary carbon.

6. The synthesis method according to claim 1 , wherein when synthesizing the polymer an aldehyde derivative is optionally used and the amount of the aldehyde derivative is 0-30 mol percent based on all the components to be used for the synthesis.

7. The synthesized method according to claim 1 , where Mw of the synthesized polymer is 959 to 1,250 Da.

8. A method of manufacturing a composition, where the composition comprises a ethynyl derived composite according to claim 1 and solvent.

9. The method of manufacturing a composition according to claim 8 ,
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.

10. The method of manufacturing a composition according to claim 8 ,
wherein the solvent comprises at least one solvent selected from the group consisting of water, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol 1-monomethyl ether 2-acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, gamma-butyrolactone, ethyl lactate, or any mixture of any of these.

11. The method of manufacturing a composition according to claim 8 , wherein the amount of the ethynyl derived composite is 2-60 mass percent relative to the total amount of the composition;
optionally the amount of the organic solvents is 60-98 mass percent relative to the total amount of the composition.

12. The method of manufacturing a composition according to claim 8 , 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.

13. The method of manufacturing a composition according to claim 8 , wherein

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