WO2017052002A1 - 2종의 평탄제를 포함하는 전해 구리 도금용 유기첨가제 및 이를 포함하는 전해 구리 도금액 - Google Patents

2종의 평탄제를 포함하는 전해 구리 도금용 유기첨가제 및 이를 포함하는 전해 구리 도금액 Download PDF

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Publication number
WO2017052002A1
WO2017052002A1 PCT/KR2016/000990 KR2016000990W WO2017052002A1 WO 2017052002 A1 WO2017052002 A1 WO 2017052002A1 KR 2016000990 W KR2016000990 W KR 2016000990W WO 2017052002 A1 WO2017052002 A1 WO 2017052002A1
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Prior art keywords
copper plating
electrolytic copper
acid
ether
mol
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PCT/KR2016/000990
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English (en)
French (fr)
Korean (ko)
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이민형
이운영
Original Assignee
한국생산기술연구원
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Priority to JP2018515665A priority Critical patent/JP6554608B2/ja
Priority to CN201680055727.7A priority patent/CN108026656B/zh
Publication of WO2017052002A1 publication Critical patent/WO2017052002A1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/62—Quaternary ammonium compounds
    • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
    • C25D3/00—Electroplating: Baths therefor
    • C25D3/02—Electroplating: Baths therefor from solutions
    • C25D3/38—Electroplating: Baths therefor from solutions of copper
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25D—PROCESSES FOR THE ELECTROLYTIC OR ELECTROPHORETIC PRODUCTION OF COATINGS; ELECTROFORMING; APPARATUS THEREFOR
    • C25D9/00—Electrolytic coating other than with metals
    • C25D9/02—Electrolytic coating other than with metals with organic materials

Definitions

  • the present invention relates to a plating composition, and more particularly, to an electrolytic copper plating composition capable of improving the flatness of a copper plating film on a substrate.
  • Electrolytic plating is a method of electrodepositing a metal or metal oxide using electrons supplied from the outside.
  • the electroplating system is composed of an electrode, an electrolyte, and a power supply for electrons in the same way as a general electrochemical system.
  • a substrate on which a pattern is formed is used as a cathode, and copper or an insoluble material containing phosphorus is used as an anode.
  • the electrolyte basically contains copper ions, sulfuric acid to lower the resistance of the electrolyte itself, and chlorine ions to improve the adsorption of copper ions and additives.
  • An object of the present invention is to provide an organic additive for electrolytic copper plating and an electrolytic copper plating solution to increase planarization of a pattern after plating when electrolytic copper plating on a substrate on which a pattern is formed.
  • these problems are exemplary, and the scope of the present invention is not limited thereby.
  • An organic additive for electrolytic copper plating according to one aspect of the present invention. It is added to a copper plating solution for forming a copper film on the substrate on which the pattern is formed by electroplating, and includes at least two planarizers to increase the uniformity and flatness of the copper film formed on the pattern.
  • the flattening agent may include a first flattening agent which makes the surface of the copper film convex, and a second flattening agent which makes the surface of the copper film concave.
  • the first flattening agent may include a compound having a structure represented by the following Chemical Formula 1.
  • (A comprises at least one of ether functionality, ester functionality and carbonyl functionality
  • T 1 and T 2 alone are hydrogen, or are linear alkyl having from 1 to 10 carbons containing ether functional groups, or from 5 to 20 carbons containing ether functional groups Branched alkyl,
  • T 3 and T 4 alone are hydrogen, linear alkyl having from 1 to 10 carbons, or branched alkyl having from 5 to 20 carbons,
  • n is an integer from 1 to 50
  • o is an integer from 1 to 100
  • X is one or more selected from the group of ions consisting of chlorine (Cl), bromine (Br), iodine (I), nitrate (NO 3 ), sulfate (SO 4 ), carbonate (CO 3 ) and hydroxyl group (OH) Included)
  • the second flattening agent may include a compound having a structure represented by the following Chemical Formula 2.
  • R 1 is alone hydrogen or linear alkyl having from 1 to 10 carbons, or branched alkyl having from 5 to 20 carbons,
  • R 2 is a substance consisting of glycidoxypropyltrimethoxysilane, butyl methacrylate, ethyl methacrylate, glycidyl methacrylate, glycidyl acrylate, glycidyl ester, glycidyl amine, glycidol Containing at least one of the counties.
  • R 3 and R 4 are unsaturated heterocyclic compounds containing one or two hetero atoms which are azirin, oxyline, thyrine, diazirine, azet, oxet, thiet, dioct, dietiate, pyrrole, Furan, thiophene, phosphol, imidazole, pyrazole, oxosol, isoxazole, thiazole, isothiazole, pyridine, pyran, thiopyran, phosphinine, diazine, oxazine, thiazine, dioxin, One or more selected from the group consisting of dityine, azepine, oxepin, thiedepine, diazepine, tiazine, and azocin,
  • X is one or more selected from the group of ions consisting of chlorine (Cl), bromine (Br), iodine (I), nitrate (NO 3 ), sulfate (SO 4 ), carbonate (CO 3 ) and hydroxyl group (OH) Included)
  • the organic additive for electrolytic copper plating may further include an inhibitor and an accelerator.
  • the inhibitor is Polyoxyalkylene glycol, Carboxymethylcellulose, N-nonylphenolpoly glycol ether, Octandiobis glycol ether, Oleic acid polyglycol ester, Polyethylene glycol, Polyethylene glycol dimethyl ether, Poly (ethylene glycol) -block- poly (propylene glycol) -block-poly (ethylene glycol), Polypropylene glycol, Poly vinyl alcohol, Stearyl alcoholpolyglycol ether, Stearic acidpolyglycol ester, 3-Methyl-l-butyne-3-ol, 3-Methyl-pentene-3-ol , L-ethynylcyclohexanol, phenyl-propynol, 3-Phenyl-l-butyne-3-ol, Propargyl alcohol, Methyl butynol-ethylene oxide, 2-Methyl-4-chloro-3-butyne-2-o
  • the accelerator is (O-Ethyldithiocarbonato) -S- (3-sulfopropyl) -ester, 3-[(Amino-iminomethyl) -thiol] -1-propanesulfonic acid, 3- (Benzothiazolyl-2-mercapto) -propyl-sulfonic acid, sodium bis- (sulfopropyl) -disulfide, N, N-Dimethyl-dithiocarbamyl propyl sulfonic acid, 3,3-Thiobis (1-propanesulfonic acid), 2-Hydroxy-3 -[tris (hydroxymethyl) methylamino] -1-propanesulfonic acid, sodium 2,3-dimercaptopropanesulfonate, 3-Mercapto-1-propanesulfonic acid, N, N-Bis (4-sulfobutyl) -3,5-dimethylani
  • An electrolytic copper plating solution is an electrolytic copper plating solution containing copper ions and an organic additive, wherein the organic additive is an accelerator, to increase the uniformity and flatness of the copper film formed on the substrate on which the pattern is formed.
  • the organic additive is an accelerator
  • the planarizing agent may include a first planarizing agent which makes the surface of the copper film convex, and a second planarizing agent which makes the surface of the copper film concave.
  • the molecular weight range of the first flattening agent is 100 g / mol to 500,000 g / mol, and may be added at a concentration of 0.1 mg to 1000 mg per liter of the electrolytic copper plating solution.
  • the second flattening agent may have a molecular weight ranging from 100 g / mol to 500,000 g / mol and may be added at a concentration ranging from 0.1 mg to 1000 mg per liter of the plating solution.
  • the inhibitor and the accelerator may have a molecular weight in the range of 100 g / mol to 100,000 g / mol, respectively, and may be added at a concentration in the range of 0.1 mg to 1000 mg per liter of the plating solution.
  • 1A is a scanning electron microscope (SEM) photograph showing the result of electrolytic copper plating performed on a substrate under the conditions of Experimental Example 1 according to the present invention.
  • FIG. 1B is a profile of a copper plated film scanned using a surface profiler for the resultant of FIG. 1A.
  • Figure 2a is a scanning electron microscope (SEM) photograph showing the result of the electrolytic copper plating on the substrate under the conditions of Experimental Example 2 according to the present invention.
  • FIG. 2B is a profile of a copper plated film scanned using a surface profiler for the resultant of FIG. 2A.
  • Figure 3a is a scanning electron microscope (SEM) photograph showing the result of the electrolytic copper plating on the substrate under the conditions of Experimental Example 3 according to the present invention.
  • FIG. 3B is a profile of a copper plated film scanned using a surface profiler for the resultant of FIG. 3A.
  • the electrolytic plating method may be distinguished from the electroless plating method in that electricity is applied.
  • electrolytic copper plating may refer to plating copper by an electrolytic plating method.
  • An organic additive for electrolytic copper plating may be added to a copper plating solution for forming a copper film by an electrolytic plating method.
  • the copper plating liquid basically includes an electrolyte containing copper ions, and may additionally include an additive added thereto.
  • the copper plating solution may include sulfuric acid for lowering the resistance to the electrolyte, chlorine ions for improving the adsorption of copper ions and additives.
  • the organic additive for electrolytic copper plating according to an embodiment of the present invention is added to a copper plating solution for forming a copper film by an electroplating method on a substrate on which a pattern is formed, and the uniformity and flatness of the copper film formed on the pattern At least two planarizers may be included to increase. In this manner, when the uniformity and flatness of the copper film are increased, the uniformity and flatness of the pattern after the copper film is formed are also increased.
  • such a planarizer may include a first planarizer that makes the surface of the copper film convex, and a second planarizer that makes the surface of the copper film concave.
  • the first flattening agent may include a compound having a structure represented by Formula 1 below.
  • (A comprises at least one of ether functionality, ester functionality and carbonyl functionality
  • T 1 and T 2 alone are hydrogen, or are linear alkyl having from 1 to 10 carbons containing ether functional groups, or from 5 to 20 carbons containing ether functional groups Branched alkyl,
  • T 3 and T 4 alone are hydrogen, linear alkyl having from 1 to 10 carbons, or branched alkyl having from 5 to 20 carbons,
  • n is an integer from 1 to 50
  • o is an integer from 1 to 100
  • X is one or more selected from the group of ions consisting of chlorine (Cl), bromine (Br), iodine (I), nitrate (NO 3 ), sulfate (SO 4 ), carbonate (CO 3 ) and hydroxyl group (OH) It may include.
  • the molecular weight range of the first planarizer is 100 g / mol to 500,000 g / mol, and may be added at a concentration of 0.1 mg to 1000 mg per liter of the electrolytic copper plating solution.
  • Such a first flattening agent is adsorbed to a plating film portion having a high current density in an electrolytic copper plating process for forming a copper film on a substrate having a pattern, thereby suppressing the reduction of copper ions, thereby providing uniformity and flatness of the copper plating film. As a result, the uniformity and flatness of the pattern after plating can be improved.
  • the second planarizer may include a compound having a structure represented by Formula 2 below.
  • R 1 is alone hydrogen or linear alkyl having from 1 to 10 carbons, or branched alkyl having from 5 to 20 carbons,
  • R 2 is a substance consisting of glycidoxypropyltrimethoxysilane, butyl methacrylate, ethyl methacrylate, glycidyl methacrylate, glycidyl acrylate, glycidyl ester, glycidyl amine, glycidol One or more selected from the group.
  • R 3 and R 4 are unsaturated heterocyclic compounds containing one or two heteroatoms (nitrogen, oxygen, sulfur, phosphorus, etc.), which are azirin, oxyline, thyrine, diazirin, azet, oxet, thiet , Dioct, dietite, pyrrole, furan, thiophene, phosphol, imidazole, pyrazole, oxosol, isoxazole, thiazole, isothiazole, pyridine, pyran, thiopyran, phosphinine, diazine At least one selected from the group consisting of oxazine, thiazine, dioxin, dityine, azepine, oxepin, tidepine, diazepine, thiazepine and azocin,
  • X is one or more selected from the group of ions consisting of chlorine (Cl), bromine (Br), iodine (I), nitrate (NO 3 ), sulfate (SO 4 ), carbonate (CO 3 ) and hydroxyl group (OH) It may include.
  • Such a second flattener has a molecular weight ranging from 100 g / mol to 500,000 g / mol and may be added at a concentration ranging from 0.1 mg to 1000 mg per liter of the plating liquid.
  • Such a second flattening agent is adsorbed to a plating film portion having a high current density in an electrolytic copper plating process for forming a copper film on a substrate having a pattern, thereby suppressing reduction of copper ions, thereby making uniformity and flatness of the copper plating film. As a result, the uniformity and flatness of the pattern after plating can be improved.
  • the organic additive for electrolytic copper plating according to some embodiments of the present invention may further include a suppressor and / or an accelerator.
  • the inhibitor may help to easily form a copper film on a substrate having a pattern by improving the wettability of the plating liquid while suppressing copper reduction in the electrolytic copper plating process.
  • the inhibitor may be polyoxyalkylene glycol, Carboxymethylcellulose, N-nonylphenolpoly glycol ether, Octandiobis glycol ether, Oleic acid polyglycol ester, Polyethylene glycol, Polyethylene glycol dimethyl ether, Poly (ethylene glycol) -block-poly (propylene glycol) -block-poly (ethylene glycol), Polypropylene glycol, Poly vinyl alcohol, Stearyl alcohol polyglycol ether, Stearic acid polyglycol ester, 3-Methyl-l-butyne-3-ol, 3-Methyl-pentene-3-ol, L-ethynylcyclohexanol, phenyl-propynol, 3-Phenyl-l-butyne-3-ol,
  • Such inhibitors have a molecular weight ranging from 100 g / mol to 100,000 g / mol and can be added at concentrations ranging from 0.1 mg to 1000 mg per liter of plating solution.
  • the accelerator may reduce the overvoltage of the plating solution in the electrolytic copper plating process to generate a high density of nuclei, and may accelerate the copper reduction reaction rate to increase nucleation and growth.
  • the accelerator is (O-Ethyldithiocarbonato) -S- (3-sulfopropyl) -ester, 3-[(Amino-iminomethyl) -thiol] -1-propanesulfonic acid, 3- (Benzothiazolyl-2-mercapto) -propyl -sulfonic acid, sodium bis- (sulfopropyl) -disulfide, N, N-Dimethyl-dithiocarbamyl propyl sulfonic acid, 3,3-Thiobis (1-propanesulfonic acid), 2-Hydroxy-3- [tris (hydroxymethyl) methylamino]- 1-propanesulfonic acid, Sodium 2,3-dimercaptopropanesulfonate
  • Such accelerators have a molecular weight ranging from 100 g / mol to 100,000 g / mol and may be added at concentrations ranging from 0.1 mg to 1000 mg per liter of plating liquid.
  • the electrolytic copper plating solution may include the aforementioned organic additive in an electrolyte containing copper ions.
  • the electrolytic copper plating solution may further include sulfuric acid for lowering the resistance of the electrolyte, chlorine ions for improving the adsorption property of the copper ions and the additive.
  • Such an electrolytic copper plating solution may be useful when a pattern is formed on a substrate, such as a semiconductor wafer, and selectively copper plating in such a pattern. Furthermore, such an electrolytic copper plating solution may be used in the formation of a passive device such as an inductor requiring a thick film copper plating, a power device, etc., as the plating speed is high and thick film plating is possible.
  • the electrolytic copper plating method may include forming a copper film by an electrolytic plating method using the electrolytic copper plating solution containing the aforementioned electrolytic copper plating organic additive.
  • Such an electrolytic copper plating method may be performed through a multi-step direct current application or pulse current application.
  • the substrate may use a structure in which a photoresist pattern is formed on a silicon wafer, and a copper film may be formed on the substrate by an electrolytic copper plating method.
  • a copper film may be thick film copper formed thickly on the pattern with a thickness of 10 ⁇ m or more, and in this case, may be used as a wiring of a passive device such as an inductor or a power device.
  • the thick film copper film may have a thickness of 10 ⁇ m to 50 ⁇ m for the inductor or the wiring.
  • the thickness of the copper film formed using the electrolytic copper plating additive or the electrolytic copper plating solution according to the present invention is not limited to this thickness.
  • Experimental Examples 1 to 3 a polyethylene oxide derivative containing an aromatic hydrocarbon as an inhibitor and 100 g of copper ions, 150 g of sulfate ions, 50 mg of chlorine ions and an inhibitor in common, and an accelerator, An organic compound containing a mercapto group was added.
  • Experimental Example 1 further added a first leveling agent as an organic additive
  • Experimental Example 2 further added a second leveling agent as an organic additive
  • Experimental Example 3 added the first leveling agent and the second leveling agent as an organic additive. More was added.
  • the first leveling agent and the second leveling agent were variously tested, and the following shows the conditions of the exemplary experimental example.
  • a of the first flattener is one of N-nitrosommethanamine, N'-hydroxyimidoformamide, diazenylmethanol, 3-diaziridinol.
  • T 1 of the first leveling agent alone contains hydrogen
  • T 2 of the first leveling agent is branched alkyl having 6 carbons containing an ether functional group.
  • the sum of m and n of a 1st planarizer is an integer of 5-10, and o of a 1st planarizer is an integer of 2-30.
  • X of the first planarizing agent is one of halogen ions.
  • R 1 of the second leveling agent is linear alkyl having three carbons
  • R 2 of the second leveling agent is one of butyl methacrylate, ethyl methacrylate, or glycidyl methacrylate.
  • R 3 and R 4 of the second leveling agent are unsaturated heterocyclic compounds, which are one of azirin, pyrrole, pyrazole, imidazole or thiazine.
  • the sum of q and r of the second leveling agent is an integer from 3 to 20, and X of the second leveling agent is one of halogen ions.
  • FIG. 1A is a scanning electron microscope (SEM) photograph showing a result of electrolytic copper plating performed on a substrate under the conditions of Experimental Example 1 according to the present invention.
  • FIG. 1B is a surface profiler of the resultant of FIG. 1A. It is the profile of the copper plating film scanned using.
  • the copper plating film according to Experimental Example 1 As shown in FIGS. 1A and 1B, in the case of the plating film according to Experimental Example 1, the copper plating film was formed in a convex shape at the center of the upper part of the pattern, and the thickness difference of the copper plating film on the upper part of the pattern was about 5.3 ⁇ m.
  • FIG. 2A is a scanning electron microscope (SEM) photograph showing a result of electrolytic copper plating performed on a substrate under the conditions of Experimental Example 2 according to the present invention.
  • FIG. 2B is a surface profiler of the resultant of FIG. 2A. It is the profile of the copper plating film scanned using.
  • the copper plating film according to Experimental Example 2 was formed in a concave shape at the center of the upper part of the pattern, and the difference in thickness of the copper plating film from the highest point to the lowest point of the upper part of the pattern was about 6.3 ⁇ m. appear.
  • FIG. 3A is a scanning electron microscope (SEM) photograph showing a result of electrolytic copper plating on a substrate under the conditions of Experimental Example 3 according to the present invention
  • FIG. 3B is a surface profiler of the resultant of FIG. 3A. It is the profile of the copper plating film scanned using.
  • the copper plating film was formed in a substantially flat shape in the center of the upper part of the pattern, and the difference in thickness of the lowest copper plating film at the highest point of the upper part of the pattern was about 1.7 ⁇ m. Appeared.
  • Experimental Example 3 can be seen that the flatness of the pattern surface is improved compared to Experimental Example 1 and Experimental Example 2.
  • the first flattening agent can make the surface of the copper film convex
  • the second flattening agent can make the surface of the copper film concave. It turns out that the uniformity and flatness of a copper plating film can be improved by mixing.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Electroplating And Plating Baths Therefor (AREA)
  • Electroplating Methods And Accessories (AREA)
PCT/KR2016/000990 2015-09-25 2016-01-29 2종의 평탄제를 포함하는 전해 구리 도금용 유기첨가제 및 이를 포함하는 전해 구리 도금액 WO2017052002A1 (ko)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2018515665A JP6554608B2 (ja) 2015-09-25 2016-01-29 ２種の平坦化剤を含む電解銅メッキ用有機添加剤及びその電解銅メッキ液
CN201680055727.7A CN108026656B (zh) 2015-09-25 2016-01-29 包含两种整平剂的电镀铜用有机添加剂以及包含该添加剂的电镀铜液

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KR10-2015-0136778 2015-09-25
KR1020150136778A KR101657675B1 (ko) 2015-09-25 2015-09-25 2종의 평탄제를 포함하는 전해 구리 도금용 유기첨가제 및 이를 포함하는 전해 구리 도금액

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KR101733141B1 (ko) * 2016-03-18 2017-05-08 한국생산기술연구원 고평탄 구리도금막 형성을 위한 전해 구리 도금용 유기첨가제 및 이를 포함하는 전해구리 도금액
KR102023363B1 (ko) * 2016-07-15 2019-09-24 한국생산기술연구원 니켈 도금용 평탄제 및 이를 포함하는 니켈 도금액
KR101818655B1 (ko) * 2016-10-20 2018-01-17 한국생산기술연구원 실리콘 관통전극의 무결함 충전방법 및 충전방법에 사용되는 구리 도금액
CN110158124B (zh) * 2019-05-24 2021-03-12 广东工业大学 一种电镀铜整平剂及其应用的电镀液
CN110938847B (zh) * 2019-10-30 2021-11-12 苏州清飙科技有限公司 电镀铜整平剂及其制备方法、以及电镀液
CN112553659A (zh) * 2020-11-09 2021-03-26 九江德福科技股份有限公司 一种高模量铜箔的制造方法
KR102339868B1 (ko) * 2021-07-30 2021-12-16 와이엠티 주식회사 레벨링제 및 이를 포함하는 비아홀 충진을 위한 전기도금 조성물
KR102372653B1 (ko) * 2021-09-06 2022-03-10 와이엠티 주식회사 레벨링제 및 이를 포함하는 범프 형성용 고속 전기 도금액
CN114875460B (zh) * 2022-04-08 2023-10-27 广州市慧科高新材料科技有限公司 一种超薄填孔镀铜整平剂的合成方法以及应用
CN117684222A (zh) * 2022-09-02 2024-03-12 宁波安集微电子科技有限公司 一种用于电解铜涂层的金属电镀组合物及其应用方法

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