Resist topcoat composition, and method of forming patterns using the composition

Patent metadata

Field	Value
Publication number	US-12554199-B2
Application number	US-202217734772-A
Country	US
Kind code	B2
Filing date	May 2, 2022
Priority date	Jul 1, 2021
Publication date	Feb 17, 2026
Grant date	Feb 17, 2026

Abstract

A resist topcoat composition and a method of forming patterns utilizing the resist topcoat composition are disclosed. The resist topcoat composition includes an acrylic polymer comprising a structural unit comprising a hydroxy group and a fluorine; a mixture comprising a first acid compound comprising at least one fluorine; and a second acid compound different from the first acid compound and comprising at least one fluorine, the first acid compound and the second acid compound are each independently selected from a sulfonic acid compound and a sulfonimide compound, the first acid compound and the second acid compound being in a weight ratio of about 1:0.1 to about 1:50; and a solvent.

First claim

What is claimed is:

1 . A resist topcoat composition, comprising
an acrylic polymer comprising a structural unit comprising a hydroxy group and a fluorine; a mixture comprising:
a first acid compound comprising at least one fluorine; and
a second acid compound different from the first acid compound and comprising at least one fluorine,
the first acid compound and the second acid compound are each independently selected from compounds represented by Chemical Formula 3 to Chemical Formula 5, the first acid compound and the second acid compound being in a weight ratio of about 1:0.1 to about 1:50; and a solvent:

and
wherein in Chemical Formula 3 to Chemical Formula 5,
R 7 to R 8 are each independently a fluorine, a C1 to C20 alkyl group substituted with at least one fluorine, and
L 3 is a C1 to C10 alkylene group substituted with at least one fluorine, a C3 to C20 cycloalkylene group substituted with at least one fluorine, a C6 to C20 arylene group substituted with at least one fluorine, or a C1 to C20 heteroarylene group substituted with at least one fluorine.

2 . The resist topcoat composition of claim 1 , wherein the acrylic polymer and the mixture are included in a weight ratio of about 3:1 to about 30:1.

3 . The resist topcoat composition of claim 1 , wherein a total weight of the acrylic polymer and the mixture is about 0.1 wt % to about 10 wt % based on a total weight of the resist topcoat composition.

4 . The resist topcoat composition of claim 1 , wherein the structural unit comprised in the acrylic polymer is represented by Chemical Formula 1:

and
wherein, in Chemical Formula 1,
R 1 is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
R 2 is hydrogen, a fluorine, a hydroxy group, or a substituted or unsubstituted C1 to C20 alkyl group,
L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C1 to C10 alkylene group,
X 1 is a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, —(CO)O—, —O(CO), —O(CO)O—, or —NR′—, wherein R′ is hydrogen, deuterium, or a C1 to C10 alkyl group,
R 2 , L 1 , and L 2 together comprises a fluorine and a hydroxy group, and
* is a linking point.

5 . The resist topcoat composition of claim 1 , wherein the structural unit of the acrylic polymer is represented by Chemical Formula 2:

and
wherein, in Chemical Formula 2,
R 1 is hydrogen or a substituted or unsubstituted C1 to C10 alkyl group,
R a , R b , R c , R d , and R 2 are each independently hydrogen, a fluorine, a hydroxy group, or a substituted or unsubstituted C1 to C20 alkyl group,
m1 and m2 are each independently an integer from 1 to 10,
X 1 is a single bond, —O—, —S—, —S(O)—, —S(O) 2 —, —C(O)—, —(CO)O—, —O(CO), —O(CO)O—, or —NR′—, wherein R′ is hydrogen, deuterium, or a C1 to C10 alkyl group,
R a , R b , R c , R d , and R 2 together comprises a fluorine and a hydroxy group, and
* is a linking point.

6 . The resist topcoat composition of claim 1 , wherein the structural unit comprising the hydroxy group and fluorine is selected from Group I:

and
wherein, in Group I,
R 3 to R 6 are each independently hydrogen or a methyl group, and
* is a linking point.

7 . The resist topcoat composition of claim 1 , wherein a weight average molecular weight of the acrylic polymer is about 1,000 g/mol to about 50,000 g/mol.

8 . The resist topcoat composition of claim 1 , wherein the first and second acid compounds are each independently selected from compounds represented by the chemical formulas of Group II:

and
wherein, in Group II,
R 10 to R 15 are each independently hydrogen, a fluorine, or a substituted or unsubstituted C1 to C10 alkyl group,
n1 and n2 are each independently an integer of 1 to 10, and
m is an integer from 0 to 10.

9 . The resist topcoat composition of claim 1 , wherein the first and second acid compounds are each independently selected from the compounds of Group II-1:

10 . The resist topcoat composition of claim 1 , wherein the solvent is an ether-based solvent represented by Chemical Formula 7:

and
wherein, in Chemical Formula 7,
R 16 and R 17 are each independently a substituted or unsubstituted C3 to C20 alkyl group.

11 . The resist topcoat composition of claim 10 , wherein the ether-based solvent is selected from diisopropyl ether, dipropyl ether, diisoamyl ether, diamyl ether, dibutyl ether, diisobutyl ether, di-sec-butyl ether, dihexyl ether, bis(2-ethylhexyl) ether, didecyl ether, diundecyl ether, didodecyl ether, ditetradecyl ether, hexadecyl ether, butyl methyl ether, butyl ethyl ether, butyl propyl ether, tert-butyl methyl ether, tert-butyl ethyl ether, tert-butylpropyl ether, di-tert-butyl ether, cyclopentylmethyl ether, cyclohexylmethyl ether, cyclopentylethyl ether, cyclohexylethyl ether, cyclopentylpropyl ether, cyclopentyl-2-propyl ether, cyclohexylpropyl ether, cyclohexyl-2-propyl ether, cyclopentylbutyl ether, cyclopentyl-tert-butyl ether, cyclohexylbutyl ether, cyclohexyl-tert-butyl ether, 2-octanone, 4-heptanone, and combinations thereof.

12 . A method of forming a pattern, the method comprising
forming a photoresist pattern on a substrate, coating the resist topcoat composition of claim 1 on the photoresist pattern, drying and heating the substrate on which the resist topcoat composition is coated to form a topcoat, and spraying a rinse solution on the substrate coated with the topcoat to remove the topcoat.

13 . The method of claim 12 , wherein the heating of the substrate coated with the resist topcoat composition is performed at a temperature of about 100° C. to about 500° C.

Assignees

• Samsung Sdi Co Ltd
• Samsung Electronics Co Ltd

Inventors

• Namgung Ran
• Park Hyeon
• Kim Minsoo
• Song Daeseok
• Chon Minki
• Kim Jun Soo
• Kim Hyun-Woo
• Song Hyun-Ji
• Choi Young Joo
• Hong Suk-Koo

Classifications

• H10P50/696

  Process specially adapted to improve the resolution of the mask · CPC title

• C08F220/282

  and containing two or more oxygen atoms · CPC title

• C09D133/16

  Homopolymers or copolymers of esters containing halogen atoms · CPC title

• G03F7/40

  Treatment after imagewise removal, e.g. baking · CPC title

• G03F7/426

  containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides · CPC title