Anti-reflective coating cleaning and post-etch residue removal composition having metal, dielectric and nitride compatibility

• US 10,460,954 B2
• Filed: 06/02/2015
• Issued: 10/29/2019
• Est. Priority Date: 06/04/2014
• Status: Active Grant

• Current Assignee: Entegris Incorporated
• Original Assignee: Entegris Incorporated
• Inventors: Cooper, Emanuel I., Lippy, Steven, Song, Lingyan
• Primary Examiner(s): Tran, Binh X
• Application Number:
  US15/316,358
• Publication Number:
  US 20170200619A1
• Time in Patent Office: 1,610 Days
• Field of Search: 252 791, 252 793, 252 794
• CPC Class Codes: C09K 13/08 containing a fluorine compound
• CPC Class Codes: C09K 13/10 containing a boron compound
• CPC Class Codes: C11D 2111/22 Electronic devices, e.g. PCBs or semiconductors
• CPC Class Codes: C11D 7/08 Acids
• CPC Class Codes: C11D 7/14 Silicates
• CPC Class Codes: C11D 7/22 Organic compounds
• CPC Class Codes: C11D 7/265 Carboxylic acids or salts thereof
• CPC Class Codes: C11D 7/28 containing halogen
• CPC Class Codes: C11D 7/3263 Amides or imides
• CPC Class Codes: C11D 7/3281 Heterocyclic compounds
• CPC Class Codes: C11D 7/34 containing sulfur
• CPC Class Codes: C11D 7/36 containing phosphorus
• CPC Class Codes: C11D 7/5022 containing oxygen
• CPC Class Codes: C23F 1/26 for etching refractory metals
• CPC Class Codes: H01L 21/02063 the processing being the formation of vias or contact holes
• CPC Class Codes: H01L 21/02071 the processing being a delineation, e.g. RIE, of conductive layers
• CPC Class Codes: H01L 21/0276 using an anti-reflective coating anti-reflective coating for lithography in general G03F7/09
• CPC Class Codes: H01L 21/31111 by chemical means
• CPC Class Codes: H01L 21/31133 by chemical means

Abstract

A liquid removal composition and process for removing anti-reflective coating (ARC) material and/or post-etch residue from a substrate having same thereon. The composition achieves at least partial removal of ARC material and/or post-etch residue in the manufacture of integrated circuitry with minimal etching of metal species on the substrate, such as aluminum, copper and cobalt alloys, and without damage to low-k dielectric and nitride-containing materials employed in the semiconductor architecture.

Claims

1. A liquid removal composition, comprising about 0.01 to about 25wt % of at least one fluoride-containing compound, about 0.01 wt % to about 99.9 wt % of at least one organic solvent, about 0.01 wt % to about 10 wt % water, about 0.01 wt % to about 20 wt % of at least one corrosion inhibitor, and about 0.01 wt % to about 2 wt % of at least one of a dielectric passivating agent and/or a silicon-containing compound, the dielectric passivating agent comprising a species selected from the group consisting of boric acid, ammonium biborate, ammonium pentaborate, sodium tetraborate, ammonium biborate, 3-hydroxy-2-naphthoic acid, iminodiacetic acid, and combinations thereof, wherein the composition is free of oxidizing agents and wherein said liquid removal composition is useful for removing anti-reflective coating (ARC) materials and/or post-etch residue from a microelectronic device having such materials and/or residue thereon.

2. The liquid removal composition of claim 1, wherein the corrosion inhibitor comprises a species selected from the group consisting of benzotriazole (BTA), 1,2,4-triazole (TAZ), 5-aminotetrazole (ATA), 1-hydroxybenzotriazole, 5-amino-1,3,4-thiadiazol-2-thiol, 3-amino-1H-1,2,4 triazole, 3,5-diamino-1,2,4-triazole, tolyltriazole, 5-phenyl-benzotriazole, 5-nitro-benzotriazole, 3-amino-5-mercapto-1,2,4-triazole, 1-amino-1,2,4-triazole, 2-(5-amino-pentyl)-benzotriazole, 1-amino-1,2,3-triazole, 1-amino-5-methyl-1,2,3-triazole, 3-mercapto-1,2,4-triazole, 3-isopropyl-1,2,4-triazole, 5-phenylthiolbenzotriazole,halo-benzotriazoles (halo=F, Cl, Br or I), naphthotriazole, 1H-tetrazole-5-acetic acid, 2-mercaptobenzothiazole (2-MBT), 1-phenyl-2-tetrazoline-5-thione, 2-mercaptobenzimidazole (MBI), 4-methyl-2-phenylimidazole, 2-mercaptothiazoline, 2,4-diamino-6-methyl-1,3,5-triazine, thiazole, imidazole, benzimidazole, triazine,methyltetrazole, Bismuthiol I, 1,3-dimethyl-2-imidazolidinone, 1,5-pentamethylenetetrazole, 1-phenyl-5-mercaptotetrazole, diaminomethyltriazine, imidazoline thione, 4-methyl-4H-1,2,4-triazole-3-thiol, 5-amino-1,3,4-thiadiazole-2-thiol, benzothiazole, tritolyl phosphate, indazole, DNA bases, pyrazoles, propanethiol, ascorbic acid, thiourea, 1,1,3,3-tetramethylurea, urea, urea derivatives, uric acid, potassium ethylxanthate, glycine, dodecylbenzenesulfonic acid (DDBSA), tartaric acid, N,N-dimethylacetoacetamide, 1-nitroso-2-napthol, polysorbate 80, dodecylphosphonic acid (DDPA), ethylenediaminetetraacetic acid (EDTA), (1,2-cyclohexylenedinitrilo)tetraacetic acid (CDTA), diethylenetriamine pentaacetic acid (DTPA), 2-phosphonobutane-1,2,4-tricarboxylic acid (PBTCA), ethylendiamine disuccinic acid, propylenediamine tetraacetic acid;

phosphonic acid;

hydroxyethylidene diphosphonic acid (HEDP), 1-hydroxyethane-1,1-diphosphonic acid, nitrilo-tris(methylenephosphonic acid) (NTMP), amino tri (methylene phosphonic acid), diethylenetriamine penta(methylenephosphonic acid), ethylenediamine tetra(methylene phosphonic acid) (EDTMPA), and combinations thereof.

3. The liquid removal composition of claim 1, comprising about 0.01wt % to about 2 wt % of at least one silicon-containing compound, wherein the silicon-containing compound comprises a species selected from the group consisting of methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane (TEOS), N-propyltrimethoxysilane, N-propyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, ammonium hexaflurorosilicate, sodium silicate, potassium silicate, tetramethyl ammonium silicate (TMAS), tetraacetoxysilane, di-t-butoxydiacetoxysilane, acetoxymethyltriethoxysilane, and combinations thereof.

4. The liquid removal composition of claim 1, wherein the at least one organic solvent comprises a compound selected from the group consisting of tetramethylene sulfone, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, t-butanol, 1-pentanol, hexanol, cyclohexanol, 2-ethyl-1-hexanol, benzyl alcohol, furfuryl alcohol, ethylene glycol, diethylene glycol, propylene glycol (1,2-propanediol), tetramethylene glycol (1,4-butanediol), 2,3-butanediol, 1,3-butanediol, neopentyl glycol, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, diethylene glycol monoethyl ether, triethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, triethylene glycol monobutyl ether, propylene glycol methyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, propylene glycol n-propyl ether, dipropylene glycol n-propyl ether, tripropylene glycol n-propyl ether, propylene glycol n-butyl ether, dipropylene glycol n-butyl ether, and tripropylene glycol n-butyl ether, dimethylacetamide, formamide, dimethylformamide, 1-methyl-2- pyrrolidinone, dimethyl sulfoxide, tetrahydrofurfuryl alcohol (THFA), and combinations thereof.

5. The liquid removal composition of claim 1, wherein at least one organic solvent comprises a compound selected from the group consisting of ethylene glycol, propylene glycol, 2-propanol, 1-propanol, 1-butanol, 1,4-butanediol, 1-pentanol, and combinations thereof.

6. The liquid removal composition of claim 1, wherein the at least one organic solvent comprises a compound selected from the group consisting of 1-butanol, 1,4-butanediol, and combinations thereof.

7. The liquid removal composition of claim 1, comprising about 0.01wt % to about 2 wt % of at least one dielectric passivating agent and about 0.01 wt % to about 2wt % of at least one silicon-containing compound.

8. The liquid removal composition of claim 1, wherein the composition comprises water and wherein water is present in an amount from about 0.01 wt % to about 1wt %, based on the total weight of the composition.

9. The liquid removal composition of claim 1, wherein the at least one fluoride-containing compound comprises a species selected from the group consisting of hydrogen fluoride, ammonium fluoride, fluoroboric acid, tetramethylammonium fluoride (TMAF), triethanolamine hydrofluoric acid salt, ammonium bifluoride ((NH4)HF2), tetraalkylammonium bifluorides ((R)4NHF2), and combinations thereof.

10. The liquid removal composition of claim 1, wherein the pH of the composition in a range from about 1 to about 5.

11. The liquid removal composition of claim 1, wherein the composition removes greater than 95% of the ARC material and/or post-etch residue and has a cobalt etch rate less than about 5 Å

min-1 at 40°

C.

12. The liquid removal composition of claim 1, further comprising residue material selected from the group consisting of ARC residue, post-etch residue, and combinations thereof.

13. A method of removing ARC material and/or post-etch residue from a microelectronic device having said material and residue thereon, said method comprising contacting the microelectronic device with a liquid removal composition for sufficient time to at least partially remove said material and residue from the microelectronic device, wherein the liquid removal composition comprises about 0.01 wt % to about 25 wt % of at least one fluoride-containing compound, about 0.01 wt % to about 99.9 wt % of at least one organic solvent, about 0.01 wt % to about 10 wt % water, about 0.01 wt % to about 20 wt % of at least one corrosion inhibitor, and about 0.01 wt % to about 2 wt % of at least one of a dielectric passivating agent and/or a one silicon-containing compound, wherein the dielectric passivating agent comprises a species selected from the group consisting of boric acid, ammonium biborate, ammonium pentaborate, sodium tetraborate, ammonium biborate, 3-hydroxy-2-naphthoic acid, iminodiacetic acid, and combinations thereof and wherein the composition is free of oxidizing agents.

14. The method of claim 13, wherein the microelectronic device is of an article selected from the group consisting of semiconductor substrates, flat panel displays, and microelectromechanical systems (MEMS).

15. The method of claim 13, wherein said contacting is carried out for a time of from about 1 minute to about 60 minutes.

16. The method of claim 13, wherein said contacting is carried out at temperature in a range of from about 20°

C. to about 80°

C.

17. The method of claim 13, wherein the corrosion inhibitor comprises a species selected from the group consisting of benzotriazole (BTA), 1,2,4-triazole (TAZ), 5-aminotetrazole (ATA), 1-hydroxybenzotriazole, 5-amino-1,3,4-thiadiazol-2-thiol, 3-amino-1H-1,2,4 triazole, 3,5-diamino-1,2,4-triazole, tolyltriazole, 5-phenyl-benzotriazole, 5-nitro-benzotriazole, 3-amino-5-mercapto-1,2,4-triazole, 1-amino-1,2,4-triazole, 2-(5-amino-pentyl) -benzotriazole, 1-amino-1,2,3-triazole, 1-amino-5-methyl-1,2,3-triazole, 3-mercapto-1,2,4-triazole, 3-isopropyl-1,2,4-triazole, 5-phenylthiolbenzotriazole,halo-benzotriazoles (halo=F, Cl, Br or I), naphthotriazole, 1H-tetrazole-5-acetic acid, 2-mercaptobenzothiazole (2-MBT), 1-phenyl-2-tetrazoline-5-thione, 2-mercaptobenzimidazole (MBI), 4-methyl-2-phenylimidazole, 2-mercaptothiazoline, 2,4-diamino-6-methyl-1,3,5-triazine, thiazole, imidazole, benzimidazole, triazine,methyltetrazole, Bismuthiol I, 1,3-dimethyl-2-imidazolidinone, 1,5-pentamethylenetetrazole, 1-phenyl-5-mercaptotetrazole, diaminomethyltriazine, imidazoline thione, 4-methyl-4H-1,2,4-triazole-3-thiol, 5-amino-1,3,4-thiadiazole-2-thiol, benzothiazole, tritolyl phosphate, indazole, DNA bases, pyrazoles, propanethiol, ascorbic acid, thiourea, 1,1,3,3-tetramethylurea, urea, urea derivatives, uric acid, potassium ethylxanthate, glycine, dodecylbenzenesulfonic acid (DDB SA), tartaric acid, N,N-dimethylacetoacetamide, 1-nitroso-2-napthol, polysorbate 80, dodecylphosphonic acid (DDPA), ethylenediaminetetraacetic acid (EDTA), (1,2-cyclohexylenedinitrilo)tetraacetic acid (CDTA), diethylenetriamine pentaacetic acid (DTPA), 2-phosphonobutane-1,2,4-tricarboxylic acid (PBTCA), ethylendiamine disuccinic acid, propylenediamine tetraacetic acid;

phosphonic acid;

hydroxyethylidene diphosphonic acid (HEDP), 1-hydroxyethane-1,1-diphosphonic acid, nitrilo-tris(methylenephosphonic acid) (NTMP), amino tri (methylene phosphonic acid), diethylenetriamine penta(methylenephosphonic acid), ethylenediamine tetra(methylene phosphonic acid) (EDTMPA), and combinations thereof.

18. The method of claim 13, wherein the liquid removal composition comprises about 0.01 wt % to about 2 wt % of at least one silicon-containing compound, wherein the silicon-containing compound comprises a species selected from the group consisting of methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane (TEOS), N-propyltrimethoxysilane, Npropyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, ammonium hexaflurorosilicate, sodium silicate, potassium silicate, tetramethyl ammonium silicate (TMAS), tetraacetoxysilane, di-tbutoxydiacetoxysilane, acetoxymethyltriethoxysilane, and combinations thereof.