Search

US-12624285-B2 - Etching composition, method of etching metal-containing film by using the same, and method of preparing semiconductor device by using the same

US12624285B2US 12624285 B2US12624285 B2US 12624285B2US-12624285-B2

Abstract

Provided are an etching composition including an oxidizing agent, an ammonium salt, an aqueous solvent, and an accelerator, a method of preparing a metal-containing film etching by using the same, and a method of manufacturing a semiconductor device by using the same.

Inventors

  • Kyuyoung HWANG
  • Byungjoon Kang
  • Daihyun Kim
  • Hwang Suk KIM
  • Mihyun PARK
  • Jungmin Oh
  • Hyosan Lee
  • Byoungki CHOI
  • Cheol Ham

Assignees

  • SAMSUNG ELECTRONICS CO., LTD.

Dates

Publication Date
20260512
Application Date
20230403
Priority Date
20220404

Claims (20)

  1. 1 . An etching composition consisting essentially of: an oxidizing agent; an ammonium salt; an aqueous solvent; and an accelerator, wherein the oxidizing agent includes hydrogen peroxide, and an amount of the oxidizing agent is 15 wt % to 25 wt % based on 100 wt % of the etching composition, the ammonium salt includes an ammonium cation and an organic anion, and the accelerator includes a compound represented by Formula 1-1, a compound represented by Formula 1-2, a compound represented by Formula 1-3, a compound represented by Formula 1-4, a compound represented by Formula 1-5, a compound represented by Formula 1-6, or any combination thereof, wherein, in Formulae 1-1 to 1-6, Ar 1 is a C 3 -C 20 unsaturated cyclic group, X 1 and X 3 are each independently C or N, X 2 in Formulae 1-1, 1-2 and 1-6 is C(R 2 ), N(R 2 ), N(H), *—N═*′, *═N—*′, O or S, X 2 in Formula 1-3 is C(R 2 ) or N(R 2 ), X 2 in Formulae 1-4 and 1-5 is N(H), *—N═*′, *═N—*′, O or S, X 1 and X 2 are linked to each other via a single bond or a double bond, X 2 and X 3 are linked to each other via a single bond or a double bond, Y 1 is C(Z 3 )(Z 4 ), N(Z 3 ), C(═O) or C(═S), T 1 is *—OH, *—SH, or*—NH 2 , T 1a is O or S, R 2 is *—O(Z 5 ), *—S(Z 5 ), or *—N(Z 5 )(Z 6 ), Z 1 , Z 3 to Z 6 , Z 11 , and Z 12 are each independently, hydrogen, deuterium, *—F, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH 2 , *—C(═O)H, *—C(═S)H, *—C(═O)—OH, *—C(═S)—OH, *—C(═O)—SH, *—C(═S)—SH, *—C(═O)—(NH 2 ), *—C(═S)—(NH 2 ), *—NH—C(═O)—(NH 2 ), *—NH—C(═S)—(NH 2 ), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(═O)—C(═S)—SH, *—C(═S)—C(═S)—SH, or*—C(═O)—ONH 4 ; or a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group, unsubstituted or substituted with deuterium, *—F, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH 2 , *—C(═O)H, *—C(═S)H, *—C(═O)—OH, *—C(═S)—OH, *—C(═O)—SH, *—C(═S)—SH, *—C(═O)—(NH 2 ), *—C(═S)—(NH 2 ), *—NH—C(═O)—(NH 2 ), *—NH—C(═S)—(NH 2 ), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(═O)—C(═S)—SH, *—C(═S)—C(═S)—SH, *—C(═O)—ONH 4 , or any combination thereof, a1 is an integer from 0 to 5, A 1 is, hydrogen or deuterium; or a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group, unsubstituted or substituted with deuterium, *—F, *—Cl, *—Br, *—I, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, or any combination thereof, and * and *′ each indicate a binding site to a neighboring atom.
  2. 2 . The etching composition of claim 1 , wherein the etching composition consists of the oxidizing agent, the ammonium salt, the aqueous solvent, and the accelerator.
  3. 3 . The etching composition of claim 1 , wherein Ar 1 is i) a 5-membered ring, ii) a 6-membered ring, iii) a condensed ring in which two or more 5-membered rings are condensed with each other, iv) a condensed ring in which two or more 6-membered rings are condensed with each other, or v) a condensed ring in which one or more 5-membered ring and one or more 6-membered ring are condensed to each other.
  4. 4 . The etching composition of claim 1 , wherein Ar 1 is a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, an imidazole group, a pyrazole group, a triazole group, a 4H-pyran-4-one group, a carbazole group, a dibenzofuran group or a dibenzothiophene group.
  5. 5 . The etching composition of claim 1 , wherein Z 1 , Z 3 to Z 6 , Z 11 , and Z 12 are each independently, hydrogen, deuterium, *—F, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH 2 , *—C(═O) H, *—C(═S) H, *—C(═O)—OH, *—C(═S)—OH, *—C(═O)—SH, *—C(═S)—SH, *—C(═O)—(NH 2 ), *—C(═S)—(NH 2 ), *—NH—C(═O)—(NH 2 ), *—NH—C(═S)—(NH 2 ), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(═O)—C(═S)—SH, *—C(═S)—C(═S)—SH, or*—C(═O)—ONH 4 ; or a C 1 -C 20 alkyl group unsubstituted or substituted with deuterium, *—F, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH 2 , *—C(═O) H, *—C(═S) H, *—C(═O)—OH, *—C(═S)—OH, *—C(═O)—SH, *—C(═S)—SH, *—C(═O)—(NH 2 ), *—C(═S)—(NH 2 ), *—NH—C(═O)—(NH 2 ), *—NH—C(═S)—(NH 2 ), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(═O)—C(═S)—SH, *—C(═S)—C(═S)—SH, *—C(═O)—ONH 4 , or any combination thereof.
  6. 6 . The etching composition of claim 1 , wherein the accelerator includes a compound represented by Formula 1-1, a compound represented by Formula 1-2, a compound represented by Formula 1-6, or any combination thereof.
  7. 7 . The etching composition of claim 1 , wherein the accelerator includes a compound represented by Formula 1-3.
  8. 8 . The etching composition of claim 1 , wherein the accelerator includes a compound represented by Formula 1-4, a compound represented by Formula 1-5, or a combination thereof.
  9. 9 . The etching composition of claim 1 , wherein the accelerator comprises at least one of Compounds E1 to E15:
  10. 10 . The etching composition of claim 1 , wherein an amount of the ammonium salt is in a range of about 0.5 wt % to about 20 wt % based on 100 wt % of the etching composition.
  11. 11 . The etching composition of claim 1 , wherein an amount of the accelerator is in a range of about 0.001 wt % to about 20 wt % based on 100 wt % of the etching composition.
  12. 12 . The etching composition of claim 1 , wherein the etching composition has a pH in a range of about 3.0 to about 8.3.
  13. 13 . A method of etching a metal-containing film, the method comprising: preparing a substrate provided with a metal-containing film; and removing at least a portion of the metal-containing film by performing an etching process using the etching composition of claim 1 to the metal-containing film.
  14. 14 . The method of claim 13 , wherein the metal-containing film comprises indium (In), titanium (Ti), aluminum (Al), lanthanum (La), scandium (Sc), gallium (Ga), zinc (Zn), hafnium (Hf), or any combination thereof.
  15. 15 . The method of claim 13 , wherein the metal-containing film comprises a metal nitride, a metal oxide, a metal oxynitride, or a combination thereof.
  16. 16 . The method of claim 15 , wherein the metal-containing film comprises a first region and a second region, a second etching speed that the etching composition etches the second region is greater than a first etching speed that the etching composition etches the first region, and the etching process is performed by contacting the etching composition with at least a portion of the first region and at least a portion of the second region.
  17. 17 . The method of claim 16 , wherein the first region substantially has an etching resistance to the etching composition and comprises the metal oxide, a silicon oxide, or any combination thereof, and at least a portion of the second region in the metal-containing film is removed by the etching process and comprises the metal nitride, the metal oxynitride, or a combination thereof.
  18. 18 . The method of claim 16 , wherein the second region comprises i) a titanium nitride, ii) a titanium nitride that further includes In, Al, La, Sc, Ga, Zn, Hf, or any combination thereof, or iii) a combination thereof.
  19. 19 . A method of manufacturing a semiconductor device, the method comprising: preparing a substrate provided with a metal-containing film; and removing at least a portion of the metal-containing film by performing an etching process using the etching composition of claim 1 to the metal-containing film.
  20. 20 . An etching composition comprising: an oxidizing agent; an ammonium salt; an aqueous solvent; and an accelerator, wherein the oxidizing agent includes hydrogen peroxide, and an amount of the oxidizing agent is 15 wt % to 25 wt % based on 100 wt % of the etching composition, the ammonium salt includes an ammonium cation and an organic anion, the etching composition does not substantially include a fluorine-containing compound, and the accelerator includes a compound represented by Formula 1-1, a compound represented by Formula 1-2, a compound represented by Formula 1-3, a compound represented by Formula 1-4, a compound represented by Formula 1-5, a compound represented by Formula 1-6, or any combination thereof, wherein, in Formulae 1-1 to 1-6, Ar 1 is a C 3 -C 20 unsaturated cyclic group, X 1 and X 3 are each independently C or N, X 2 in Formulae 1-1, 1-2 and 1-6 is C(R 2 ), N(R 2 ), N(H), *—N═*′, *═N—*′, O or S, X 2 in Formula 1-3 is C(R 2 ) or N(R 2 ), X 2 in Formulae 1-4 and 1-5 is N(H), *—N═*‘, *═N—*’, O or S, X 1 and X 2 are linked to each other via a single bond or a double bond, X 2 and X 3 are linked to each other via a single bond or a double bond, Y 1 is C(Z 3 ) (Z 4 ), N(Z 3 ), C(═O) or C(═S), T 1 is*—OH, *—SH, or*—NH 2 , T 1a is O or S, R 2 is*—O(Z 5 ), *—S(Z 5 ), or*—N(Z 5 ) (Z 6 ), Z 1 , Z 3 to Z 6 , Z 11 , and Z 12 are each independently, hydrogen, deuterium, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH 2 , *—C(═O) H, *—C(═S) H, *—C(═O)—OH, *—C(═S)—OH, *—C(—O)—SH, *—C(═S)—SH, *—C(═O)—(NH 2 ), *—C(═S)—(NH 2 ), *—NH—C(═O)—(NH 2 ), *—NH—C(═S)—(NH 2 ), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(—O)—C(═S)—SH, *—C(═S)—C(═S)—SH, or*—C(═O)—ONH 4 ; or a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group, unsubstituted or substituted with deuterium, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH 2 , *—C(═O) H, *—C(═S) H, *—C(═O)—OH, *—C(═S)—OH, *—C(═O)—SH, *—C(═S)—SH, *—C(═O)—(NH 2 ), *—C(═S)—(NH 2 ), *—NH—C(═O)—(NH 2 ), *—NH—C(═S)—(NH 2 ), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(═O)—C(═S)—SH, *—C(═S)—C(═S)—SH, *—C(═O)—ONH 4 , or any combination thereof, a1 is an integer from 0 to 5, A 1 is, hydrogen or deuterium; or a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 1 -C 20 alkoxy group, a C 6 -C 20 aryl group, or a C 2 -C 20 heteroaryl group, unsubstituted or substituted with deuterium, *—Cl, *—Br, *—I, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, or any combination thereof, and * and *′ each indicate a binding site to a neighboring atom.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS This application is based on and claims priority under 35 U.S.C. § 119 to Korean Patent Application No. 10-2022-0041912, filed on Apr. 4, 2022, 10-2022-0168160, filed on Dec. 5, 2022, and 10-2023-0042150, filed on Mar. 30, 2023, in the Korean Intellectual Property Office, the disclosures of which are incorporated by reference herein in their entirety. BACKGROUND 1. Field The present disclosure relates to an etching composition, a method of etching a metal-containing film by using the same, and a method of manufacturing a semiconductor device by using the same. 2. Description of the Related Art To satisfy excellent performance and low price demanded by consumers, an increase in the degree of integration and improvement in reliability of semiconductor devices are required. As the degree of integration of the semiconductor devices increases, damage to components of the semiconductor devices during a process of manufacturing the semiconductor devices has a greater effect on reliability and electrical characteristics of semiconductor memory devices. In particular, in the process of manufacturing the semiconductor devices, various etching processes may be performed on a predetermined film (e.g., a metal-containing film). However, to perform an effective etching process, the need for an etching composition capable of providing an excellent etching speed, excellent etching selectivity for adjacent films, the absence of surface residues after etching, excellent storage stability, and the like has been continuously demanded. SUMMARY Provided is an etching composition having a high etching speed for a metal-containing film, which is a target film to be etched, and excellent etching selectivity for adjacent films composition, with substantially leaving no surface residue on a surface of a target etching film after the etching. Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments of the disclosure. According to an embodiment, an etching composition may include an oxidizing agent, an ammonium salt, an aqueous solvent, and an accelerator. The ammonium salt may include an ammonium cation and an organic anion. The accelerator may include a compound represented by Formula 1-1, a compound represented by Formula 1-2, a compound represented by Formula 1-3, a compound represented by Formula 1-4, a compound represented by Formula 1-5, a compound represented by Formula 1-6, or any combination thereof: In Formulae 1-1 to 1-6, Ar1 is a C3-C20 unsaturated cyclic group,X1 and X3 are each independently C or N,X2 in Formulae 1-1, 1-2 and 1-6 is C(R2), N(R2), N(H), *—N═*′, *═N—*′, O or S,X2 in Formula 1-3 is C(R2) or N(R2),X2 in Formulae 1-4 and 1-5 is N(H), *—N═*′, *═N—*′, O or S,X1 and X2 are linked to each other via a single bond or a double bond,X2 and X3 are linked to each other via a single bond or a double bond,Y1 is C(Z3)(Z4), N(Z3), C(═O) or C(═S),T1 is *—OH, *—SH, or *—NH2,T1a is O or S,R2 is *—O(Z5), *—S(Z5), or *—N(Z5)(Z6),Z1, Z3 to Z6, Z11, and Z12 are each independently,hydrogen, deuterium, *—F, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH2, *—C(═O)H, *—C(═S)H, *—C(═O)—OH, *—C(═S)—OH, *—C(═O)—SH, *—C(═S)—SH, *—C(═O)—(NH2), *—C(═S)—(NH2), *—NH—C(═O)—(NH2), *—NH—C(═S)—(NH2), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(═O)—C(═S)—SH, *—C(═S)—C(═S)—SH, or *—C(═O)—ONH4; ora C1-C20 alkyl group, a C2-C20 alkenyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, or a C2-C20 heteroaryl group, unsubstituted or substituted with deuterium, *—F, *—Cl, *—Br, *—I, *—OH, *—SH, *—NH2, *—C(═O)H, *—C(═S)H, *—C(═O)—OH, *—C(═S)—OH, *—C(═O)—SH, *—C(═S)—SH, *—C(═O)—(NH2), *—C(═S)—(NH2), *—NH—C(═O)—(NH2), *—NH—C(═S)—(NH2), *—C(OH)—C(═O)—OH, *—C(SH)—C(═O)—OH, *—C(OH)—C(═S)—OH, *—C(OH)—C(═O)—SH, *—C(SH)—C(═S)—OH, *—C(SH)—C(═O)—SH, *—C(OH)—C(═S)—SH, *—C(SH)—C(═S)—SH, *—C(═O)—C(═O)—OH, *—C(═S)—C(═O)—OH, *—C(═O)—C(═S)—OH, *—C(═O)—C(═O)—SH, *—C(═S)—C(═S)—OH, *—C(═S)—C(═O)—SH, *—C(═O)—C(═S)—SH, *—C(═S)—C(═S)—SH, *—C(═O)—ONH4, or any combination thereof,a1 is an integer from 0 to 5,A1 is,hydrogen or deuterium; ora C1-C20 alkyl group, a C2-C20 alkenyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, or a C2-C20 heteroaryl group, unsubstituted or substituted with deuterium, *—F, *—Cl, *—Br, *—I, a C1-C20 alkyl group, a C1-C20 alkoxy group, or any combination thereof, and* and *′ each indicate a binding site to a neighboring atom. In some embodiments, in Formulae 1-1 to 1-6, Ar1 may be i) a 5-membered ring, ii) a 6-membered ring, iii) a condensed ring in which two or more 5-membered rings are condensed with each other, iv) a condensed ring in which two or more 6-membered rings are cond