EP0507074A1
Expired / Lapsed
EP
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Cleaning agents comprising beta-diketone and beta-ketoimine ligands and a process for using the same
Assignee: Air Products and Chemicals Inc
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Filing: 1992-02-25
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Granted: —
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Expires: 2012-02-25
Abstract
Abstract This invention is a residue-free cleaning process for removing metal-containing contaminants from a surface of a substrate of the type used in manufacturing semi-conductor devices. The process comprises contacting the substrate with an effective amount of a cleaning agent comprising a β-diketone or β-ketoimine dispersed in an atmosphere capable of oxidizing the metal-contaminants at a temperature sufficient to form volatile metal-ligand complexes on the surface of the substrate. The volatile metal-ligand complexes are sublimed from the surface of the substrate leaving essentially no residue.
Inventors
- 👤 David Allen Roberts
- 👤 John Christopher Ivankovits
- 👤 John Anthony Thomas Norman
- 👤 David Arthur Bohling
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-24 08:56
CPC Classifications
C; C11; C11D; C11D3/00; C11D3/16; C11D3/26; C11D3/30; H; H10; H10P; H10P70/00; H10P70/10; H10P70/12; B; B23; B23K; B23K35/00; B23K35/22; B23K35/36; B23K35/3612; B23K35/3615; B23K35/38; C11D7/00; C11D7/22; C11D7/26; C11D7/264; C11D7/28; C11D7/32; C11D7/3236; C23; C23F; C23F1/00; C23F1/10; C23F1/12; H10P70/125; H05; H05K; H05K3/00; H05K3/30; H05K3/32; H05K3/34; H05K3/3489
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
220 words
A cleaning agent for removing metal-containing contaminants from a surface of a substrate wherein the substrate is not capable of reacting with the cleaning agent comprising a β-diketone or β-ketoimine ligand represented by the formula: wherein: R₁ and R₃ are independently selected from a linear or branched non-fluorinated, partially-fluorinated or fully fluorinated alkyl, alkenyl or aryl group having from 1 to about 8 carbon atoms; R₂ is a hydrogen atom, a fluorine atom or a linear or branched non-fluorinated, partially-fluorinated or fully fluorinated alkyl or alkenyl group having from 1 to about 8 carbon atoms; and Y is selected from an oxygen atom; N-R₄ wherein R₄ is selected from a non-fluorinated, partially fluorinated, or fully fluorinated alkyl, aryl, aralkyl or hydroxyalkyl group having from 1 to about 10 carbon atoms, or Y is wherein: R₅. R₆ and R₇ are independently selected from a hydrogen atom, a fluorine atom or a linear or branched non-fluorinated, partially fluorinated or fully fluorinated alkyl or alkenyl group having from 1 to about 8 carbon atoms; and R₈ is a linear or branched non-fluorinated, partially fluorinated or fully fluorinated alkylene, alkenylene, phenylene, alkylphenylene or hydroxyalkylene group having from 1 to about 8 carbon atoms. wherein the ligand is dispersed in an atmosphere capable of oxidizing the metal-containing contaminants residing on the surface of the substrate.
Claim 2
Dependent Claim
21 words
The cleaning agent according to Claim 2 wherein the oxidizing atmosphere is selected from oxygen, air, HLl, Br₂, Cl₂ or HF.
Claim 3
Dependent Claim
115 words
A cleaning agent for removing metal-containing contaminants from a surface of a substrate wherein the substrate is not capable of reacting with the cleaning agent comprising a β-diketone ligand represented by the formula: wherein: R₁ and R₃ are independently selected from a linear or branched non-fluorinated, partially-fluorinated or fully fluorinated alkyl, alkenyl or aryl group having from 1 to about 8 carbon atoms; and R₂ is a hydrogen atom, a fluorine atom or a linear or branched non-fluorinated, partially-fluorinated or fully fluorinated alkyl or alkenyl group having from 1 to about 8 carbon atoms; wherein the ligand is dispersed in an atmosphere capable of oxidizing the metal-containing contaminants residing on the surface of the substrate.
Claim 4
Dependent Claim
21 words
The cleaning agent according to Claim 3 wherein the oxidizing atmosphere is selected from oxygen, air, HCl, Br₂, Cl₂ or HF.
Claim 5
Dependent Claim
41 words
The cleaning agent according to Claim 4 wherein R₁ and R₃ are independently selected from a fully fluorinated linear or branched alkyl group having from 1 to about 4 carbon atoms and R₂ is a hydrogen atom or a fluorine atom.
Claim 6
Dependent Claim
19 words
The cleaning agent according to Claim 4 wherein the ligand is selected from 1,1,1,5,5,5-hexafluoro-2,4-pentanedione, 1,1,1-trifluoro-2,4- pentanedione, 2,2,6,6-tetramethyl-3,5-heptanedione and 1,1,1,5,5,6,6,7,7,7-decafluoro-2,4-heptanedione.
Claim 7
Dependent Claim
12 words
The cleaning agent according to Claim 4 wherein the ligand is 1,1,1,5,5,5-hexafluoro-2,4-pentanedione.
Claim 8
Dependent Claim
139 words
A cleaning agent for removing metal-containing contaminants from a surface of a substrate wherein the substrate is not capable of reacting with the cleaning agent comprising a β-ketoimine ligand represented by the formula: wherein: R₁ and R₃ are independently selected from a linear or branched non-fluorinated, partially-fluorinated or fully fluorinated alkyl, alkenyl or aryl group having from 1 to about 8 carbon atoms; R₂ is a hydrogen atom, a fluorine atom or a linear or branched non-fluorlnated, partially-fluorinated or fully fluorinated alkyl or alkenyl group having from 1 to about 8 carbon atoms; and R₄ is selected from a non-fluorinated, partially fluorinated or fully fluorinated alkyl, aralkyl or hydroxyalkyl group having from 1 to about 10 carbon atoms; wherein the ligand is dispersed in an atmosphere capable of oxidizing the metal-containing contaminants residing on the surface of the substrate.
Claim 9
Dependent Claim
21 words
The cleaning agent according to Claim 8 wherein the oxidizing atmosphere is selected from oxygen, air, HCl, Br₂, Cl₂ or HF.
Claim 10
Dependent Claim
41 words
The cleaning agent according to Claim 9 wherein R₁ and R₃ are independently selected from a fully fluorinated linear or branched alkyl group having from 1 to about 4 carbon atoms and R₂ is a hydrogen atom or a fluorine atom.
Claim 11
Dependent Claim
18 words
The cleaning agent according to Claim 9 wherein the ligand is selected from 4-(2,2,2-trifluoroethyl)imino-1,1,1,5,5,5-hexafluoro-2-pentanone, 5-(2,2,2-trifluoroethyl)imino-1,1,1,2,2,6,6,6-octafluoro-3-hexanone, 6-(2,2,2-trifluoroethyl)imino-1,1,1,2,2,3,3,7,7,7-decafluoro-4-heptanone and 4-(phenyl)imino-1,1,1,5,5,5-hexafluoro-2-pentanone.
Claim 12
Dependent Claim
176 words
A cleaning agent for removing metal-containing contaminants from a surface of a substrate wherein the substrate is not capable of reacting with the cleaning agent comprising a β-ketoimine ligand represented by the formula: wherein: R₁ and R₃ are independently selected from a linear or branched non-fluorinated, partially-fluorinated or fully fluorinated alkyl, alkenyl or aryl group having from 1 to about 8 carbon atoms; R₂ is a hydrogen atom, a fluorine atom or a linear or branched non-fluorinated, partially-fluorinated or fully fluorinated alkyl or alkenyl group having from 1 to about 8 carbon atoms; R₅, R₆ and R₇ are independently selected from a hydrogen atom, a fluorine atom or a non-fluorinated, partially fluorinated or fully fluorinated alkyl or alkenyl group having from 1 to about 8 carbon atoms; and R₈ is a non-fluorinated, partially fluorinated or fully fluorinated linear or branched alkylene, alkenylene, phenylene, alkylphenylene or hydroxyalkylene group having from 1 to about 8 carbon atoms; wherein the ligand is dispersed in an atmosphere capable of oxidizing the metal-containing contaminants residing on the surface of the substrate.
Claim 13
Dependent Claim
21 words
The cleaning agent according to Claim 12 wherein the oxidizing atmosphere is selected from oxygen, air, HCl, Br₂, Cl₂ or HF.
Claim 14
Dependent Claim
41 words
The cleaning agent according to Claim 13 wherein R₁ and R₃ are independently selected from a fully fluorinated linear or branched alkyl group having from 1 to about 4 carbon atoms and R₂ is a hydrogen atom or a fluorine atom.
Claim 15
Dependent Claim
18 words
The cleaning agent according to Claim 12 wherein the ligand is selected from 1,2-di[4-imino-1,1,1,5,5,5-hexafluoro-2-pentanone]ethane, 1,2-di[5-imino-1,1,1,2,2,6,6,6-octafluoro-3-hexanone]ethane, 1,2-di-[6-imino-1,1,1,2,2,3,3,7,7,7-decafluoro-4-heptanone]ethane and Bis[4-methylene)imino-1,1,1,5,5,5-hexafluoro-2-pentanone]methane.
Claim 16
Dependent Claim
69 words
A process for cleaning metal-containing contaminants from a surface of a substrate of the type used in manufacturing semi-conductor devices comprising contacting a portion of the substrate to be cleaned with an effective amount of the cleaning agent according to Claim 2 at a temperature sufficient to form a volatile metal-ligand complex on the surface of the substrate and subliming the metal-ligand complex from the surface of the substrate.
Claim 17
Dependent Claim
22 words
The process according to Claim 16 wherein the substrate is selected from silicon, silicon oxide, borophosphosilicate glass, phosphosilicate glass and strontium titanate.
Claim 18
Dependent Claim
26 words
The process according to Claim 17 wherein the metal-containing contaminants comprise at least one metal oxide represented by the formulae MO, MO₂, MO₃, M₂O and M₂O₃.
Claim 19
Dependent Claim
41 words
The process according to Claim 17 wherein the metal-containing contaminants comprise at least one metal halide represented by the formula M +n (X) -n , wherein n is 1, 2 or 3 and X is a chlorine, bromine or iodine atom.
Claim 20
Dependent Claim
69 words
A process for cleaning metal-containing contaminants from a surface of a substrate of the type used in manufacturing semi-conductor devices comprising contacting a portion of the substrate to be cleaned with an effective amount of the cleaning agent according to Claim 4 at a temperature sufficient to form a volatile metal-ligand complex on the surface of the substrate and subliming the metal-ligand complex from the surface of the substrate.
Claim 21
Dependent Claim
22 words
The process according to Claim 20 wherein the substrate is selected from silicon, silicon oxide, borophosphosilicate glass, phosphosilicate glass and strontium titanate.
Claim 22
Dependent Claim
26 words
The process according to Claim 21 wherein the metal-containing contaminants comprise at least one metal oxide represented by the formulae MO, MO₂, MO₃, M₂O and M₂O₃.
Claim 23
Dependent Claim
41 words
The process according to Claim 21 wherein the metal-containing contaminant comprises at least one metal halide represented by the formula M +n (X) -n , wherein n is 1, 2 or 3 and X is a chlorine, bromine or iodine atom.
Claim 24
Dependent Claim
17 words
The process according to Claim 20 wherein the ligand is selected from 1,1,1,5,5,5-hexafluoro-2,4-pentanedione, 1,1,1-trifluoro-2,4-pentanedione, 2,2,6,6-tetramethyl-3,5-heptanedione and 1,1,1,5,5,6,6,7,7,7-decafluoro-2,4-heptanedione.
Claim 25
Dependent Claim
11 words
The process according to Claim 21 wherein the ligand is 1,1,1,5,5,5-hexafluoro-2,4-pentanedione.
Claim 26
Dependent Claim
69 words
A process for cleaning metal-containing contaminants from a surface of a substrate of the type used in manufacturing semi-conductor devices comprising contacting a portion of the substrate to be cleaned with an effective amount of a cleaning agent according to Claim 9 at a temperature sufficient to form a volatile metal-ligand complex on the surface of the substrate and subliming the metal-ligand complex from the surface of the substrate.
Claim 27
Dependent Claim
22 words
The process according to Claim 26 wherein the substrate is selected from silicon, silicon oxide, borophosphosilicate glass, phosphosilicate glass and strontium titanate.
Claim 28
Dependent Claim
26 words
The process according to Claim 26 wherein the metal-containing contaminants comprise at least one metal oxide represented by the formulae MO, MO₂, MO₃, M₂O and M₂O₃.
Claim 29
Dependent Claim
41 words
The process according to Claim 26 wherein the metal-containing contaminants comprises at least one metal halide represented by the formula M +n (X) -n , wherein n is 1, 2 or 3 and X is a chlorine, bromine or iodine atom.
Claim 30
Dependent Claim
17 words
The process according to Claim 26 wherein the ligand is selected from 4-(2,2,2-trifluoroethyl)imino-1,1,1,5,5,5-hexafluoro-2-pentanone, 5-(2,2,2-trifluoroethyl)imino-1,1,1,2,2,6,6,6-octafluoro-3-hexanone, 6-(2,2,2-trifluoroethyl)imino-1,1,1,2,2,3,3,7,7,7,-decafluoro-4-heptanone and 4-(phenyl)imino-1,1,1,5,5,5-hexafluoro-2-pentanone.
Claim 31
Dependent Claim
69 words
A process for cleaning metal-containing contaminants from a surface of a substrate of the type used in manufacturing semi-conductor devices comprising contacting a portion of the substrate to be cleaned with an effective amount of the cleaning agent according to Claim 13 at a temperature sufficient to form a volatile metal-ligand complex on the surface of the substrate and subliming the metal-ligand complex from the surface of the substrate.
Claim 32
Dependent Claim
22 words
The process according to Claim 31 wherein the substrate is selected from silicon, silicon oxide, borophosphosilicate glass, phosphosilicate glass and strontium titanate.
Claim 33
Dependent Claim
26 words
The process according to Claim 31 wherein the metal-containing contaminants comprise at least one metal oxide represented by the formulae MO, MO₂, MO₃, M₂O and M₂O₃.
Claim 34
Dependent Claim
41 words
The process according to Claim 31 wherein the metal-containing species comprises at least one metal halide represented by the formula M +n (X) -n , wherein n is 1, 2 or 3 and X is a chlorine, bromine or iodine atom.
Claim 35
Dependent Claim
17 words
The process according to Claim 31 wherein the ligand is selected from 1,2-di[4-imino-1,1,1,5,5,5-hexafluoro-2-pentanone]ethane, 1,2-di[5-imino-1,1,1,2,2,6,6,6-octafluoro-3-hexanone]ethane, 1,2-di-[6-imino-1,1,1,2,2,3,3,7,7,7-decafluoro-4-heptanone]lethane and Bis[4-methylene)imino-1,1,1,5,5,5-hexafluoro-2-pentanone]methane.
References Cited (Backward Citations)
US5028724A
Cited
US5062902A
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