Photoresist composition including a chrysene compound, method of forming a pattern using the same, and method of fabricating 6-nitrochrysene

Patent metadata

Field	Value
Publication number	US-12516014-B2
Application number	US-202318119388-A
Country	US
Kind code	B2
Filing date	Mar 9, 2023
Priority date	May 4, 2022
Publication date	Jan 6, 2026
Grant date	Jan 6, 2026

Abstract

A photoresist composition, a method of forming a pattern, and a method of synthesizing 6-nitrochrysene, the photoresist composition includes a polymer resin; a photo acid generator; a quencher; an organic solvent; and an etching resistance enhancer, wherein the etching resistance enhancer is represented by the following Chemical Formula 1,

First claim

What is claimed is:

1 . A photoresist composition, comprising:
a polymer resin; a photo acid generator; a quencher; an organic solvent; and an etching resistance enhancer, wherein: the etching resistance enhancer is represented by the following Chemical Formula 1,

in Chemical Formula 1, R is a nitro group, a nitrile group, a trifluoromethyl group, an acetate group, or a triisopropylsilyl group.

2 . The photoresist composition as claimed in claim 1 , wherein:
R is a nitro group, and the etching resistance enhancer is represented by the following Chemical Formula 2,

3 . The photoresist composition as claimed in claim 1 , wherein the photoresist composition includes the etching resistance enhancer in an amount of 0.1 wt % to 1 wt %, based on a total weight of the photoresist composition.

4 . The photoresist composition as claimed in claim 3 , wherein the photoresist composition includes:
3 wt % to 20 wt % of the polymer resin, 0.5 wt % to 10 wt % of the photo acid generator, 0.1 wt % to 5 wt % of the quencher, and 64 wt % to 96.3 wt % of the organic solvent, all wt % being based on the total weight of the photoresist composition.

5 . The photoresist composition as claimed in claim 1 , wherein the polymer resin includes polymethylmethacrylate, poly(t-butylmethacrylate), poly(methacrylic acid), or poly(norbornylmethacrylate).

6 . The photoresist composition as claimed in claim 1 , wherein the photo acid generator includes an aryldiazonium salt, a diaryliodonium salt, a triarylsulfonium salt, a triarylphosphonium salt, a carboxylic acid, a sulfonic acid, a phosphoric acid, or a hydrogen halide.

7 . The photoresist composition as claimed in claim 1 , wherein the quencher includes hydrogen chloride, an ethyl ester, an alcohol, water, a fluorine compound, a cyanide compound, a ketone compound, a bromide compound, an iodide compound, an amine compound, an aldehyde compound, a phenol compound, a nitro compound, or a triarylsulfonium salt.

8 . The photoresist composition as claimed in claim 1 , wherein the organic solvent includes propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 2-hydroxyisobutyric acid methyl ester, ethyl lactate, ethyl lactate, cyclohexanone, heptanone, or lactone.

9 . A method of forming a pattern, the method comprising:
forming an etching target layer on a substrate; coating the etching target layer with a photoresist composition to form a photoresist layer; performing an exposure process on the photoresist layer; performing a developing process on the photoresist layer to form a photoresist pattern; and etching the etching target layer using the photoresist pattern as an etch mask to form a mask pattern, wherein: the photoresist composition includes:
a polymer resin;
a photo acid generator;
a quencher;
an organic solvent; and
an etching resistance enhancer, and
the etching resistance enhancer is represented by the following Chemical Formula 1,

in Chemical Formula 1, R is a nitro group, a nitrile group, a trifluoromethyl group, an acetate group, or a triisopropylsilyl group.

10 . The method as claimed in claim 9 , wherein the etching resistance enhancer represented by Chemical Formula 1 is represented by the following Chemical Formula 2,

11 . A method of synthesizing 6-nitrochrysene, the method comprising:
dissolving 1-(chloromethyl)naphthalene in a first solvent to prepare a first solution, adding triphenylphosphine into the first solution, and stirring the first solution to obtain a first product; filtering the first product and washing the first product with a first detergent; dissolving the first product in a second solvent to prepare a second solution, and adding tetrabutylammoniumhydroxide and benzaldehyde into the second solution and stirring the second solution to obtain a second product; separating and purifying the second product using a column chromatography; dissolving the second product in a third solvent to prepare a third solution, and adding iodine into the third solution and irradiating ultraviolet rays to the third solution while stirring the third solution; removing iodine from the third solution by using an aqueous sodium thiosulfate solution and performing a first extraction process by using water and toluene to obtain a first organic layer; removing toluene from the first organic layer and washing the first organic layer using a second detergent to obtain a third product; dissolving the third product in a fourth solvent to prepare a fourth solution; and adding a nitric acid solution into the fourth solution and reacting the third product with the nitric acid solution.

12 . The method as claimed in claim 11 , wherein:
the first solvent is toluene, and the first detergent is diethyl ether.

13 . The method as claimed in claim 11 , wherein:
the second solvent is dichloromethane, and the third solvent is toluene.

14 . The method as claimed in claim 11 , further comprising:
adding sodium bicarbonate aqueous solution into the fourth solution to neutralize the fourth solution, and performing a second extraction process using water and dichloromethane to obtain a second organic layer; and separating and purifying the second organic layer using a column chromatography and washing the second organic layer.

15 . The method as claimed in claim 14 , wherein the fourth solvent is dichloromethane.

16 . The method as claimed in claim 11 , wherein stirring the first solution to obtain a first product is carried out at 100° C. to 120° C. for 10 hours to 14 hours.

17 . The method as claimed in claim 11 , wherein the 1-(chloromethyl)naphthalene and the triphenylphosphine are added into the first solution in a molar ratio of 1:3.

18 . The method as claimed in claim 11 , wherein the stirring the second solution to obtain a second product is carried out at 10 to 40° C. for 10 to 14 hours.

19 . The method as claimed in claim 11 , wherein the stirring the third solution is carried out for 20 to 28 hours.

20 . The method as claimed in claim 11 , wherein:
the first product is

the second product is

and
the third product is chrysene.

Assignees

• Samsung Electronics Co Ltd
• Seoul Nat Univ R&Db Foundation

Inventors

• Kim Jonghoon
• Hong Suk Koo
• Kim Young Gyu
• Song Jooyoung
• Yang Hae Min
• Jeon Gumhye
• Kim Juhee
• Lee Sunah
• Lee Ahhyun
• Lee Hong Won

Classifications

• G03F7/0382

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• G03F7/029 Primary

  Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur · CPC title

• C07C5/41

  Catalytic processes · CPC title

• C07C2527/08

  Halides (C07C2527/122 - C07C2527/138 take precedence) · CPC title