WO2009145526A2 - Protective film composition for wafer dicing - Google Patents

Protective film composition for wafer dicing Download PDF

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Publication number
WO2009145526A2
WO2009145526A2 PCT/KR2009/002727 KR2009002727W WO2009145526A2 WO 2009145526 A2 WO2009145526 A2 WO 2009145526A2 KR 2009002727 W KR2009002727 W KR 2009002727W WO 2009145526 A2 WO2009145526 A2 WO 2009145526A2
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WO
WIPO (PCT)
Prior art keywords
protective film
water
film composition
group
polyethyloxazoline
Prior art date
Application number
PCT/KR2009/002727
Other languages
French (fr)
Other versions
WO2009145526A3 (en
Inventor
Kyong-Ho Lee
Gi-Jin Kwun
Shi-Jin Sung
Original Assignee
Dongwoo Fine-Chem. Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020080050260A external-priority patent/KR101539762B1/en
Priority claimed from KR1020080050261A external-priority patent/KR101539763B1/en
Application filed by Dongwoo Fine-Chem. Co., Ltd. filed Critical Dongwoo Fine-Chem. Co., Ltd.
Priority to JP2011511503A priority Critical patent/JP5511799B2/en
Priority to CN200980125936.4A priority patent/CN102077326B/en
Publication of WO2009145526A2 publication Critical patent/WO2009145526A2/en
Publication of WO2009145526A3 publication Critical patent/WO2009145526A3/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L37/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L39/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions of derivatives of such polymers
    • C08L39/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
    • C08L39/06—Homopolymers or copolymers of N-vinyl-pyrrolidones
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
    • H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
    • H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
    • H01L21/6836—Wafer tapes, e.g. grinding or dicing support tapes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2221/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof covered by H01L21/00
    • H01L2221/67—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere
    • H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
    • H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
    • H01L2221/68327—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support used during dicing or grinding

Definitions

  • the present invention relates to a protective film composition having superior thermal stability, which is used for a semiconductor dicing process.
  • a wafer dicing process follows a semiconductor lamination process so that devices which are respectively arranged are separated by cutting the wafer along the boundary region called a street therebetween. After the cutting process, a chip manufacturing process is performed, thus completing a semiconductor product.
  • polyimide which is the main material in an insulating film at the uppermost location of the laminate may be broken or damaged in the course of the wafer dicing process.
  • the wafer dicing process is changed from cutting of the wafer using a blade toward perforation of the wafer using a laser and then cutting thereof using a blade.
  • a process of cutting the wafer using only a laser may be employed.
  • fumes may be generated and may scatter due to the heat of the laser, thereby causing a problem that the upper surface of the wafer is contaminated.
  • Disclosed as known techniques for solving this problem is a process method including applying a water-soluble resin such as polyvinyl alcohol, polyethylene glycol or cellulose on the upper surface of a wafer to thus form a protective film and then radiating laser light.
  • a water-soluble resin such as polyvinyl alcohol, polyethylene glycol or cellulose
  • silicon gas may be generated from the cut surface of the wafer due to the heat of laser light, undesirably delaminating the protective film of the wafer.
  • fumes may be generated along with the silicon gas and thus may accumulate between the protective film in a delaminated state and the upper surface of the wafer. When the protective film of the wafer is subsequently washed with water, such fume deposits are not removed but remain as defects.
  • the water-soluble resin has poor thermal stability.
  • internal heat may be generated, and the water-soluble resin such as polyvinyl alcohol may be pyrolyzed by such heat.
  • a crosslinking reaction may take place, and the resultant crosslinked material is not removed even by water washing after the laser wafer dicing process, but remains on the upper surface of the wafer.
  • the laser wafer dicing process typically includes perforating the wafer using a laser and then cutting the wafer using a blade.
  • the protective film of the wafer may break, and thereby impurities occurring upon cutting of the wafer may infiltrate interstices of the broken film. Because such impurities which are water-insoluble adhere to the upper surface of the wafer, they are not washed off with water and become defects.
  • an object of the present invention is to provide a protective film composition for wafer dicing, which has high thermal stability to thus prevent the production of a pyrolyzed crosslinked material due to irradiation of a laser in a dicing process, exhibits high adhesive force to a wafer to thus prevent the delamination of a protective film in a laser wafer dicing process, and forms a protective film having appropriate hardness so that the protective film is not broken even when the wafer is perforated by a laser and then cut using a blade.
  • the present invention provides a protective film composition for wafer dicing, including at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer, and a solvent, such as water or a mixture of water and an organic solvent.
  • the protective film composition for wafer dicing has high thermal stability to thus prevent the production of a pyrolyzed crosslinked material due to irradiation of laser in a dicing process, and exhibits high adhesive force to a wafer to thus prevent the delamination of a protective film in a laser wafer dicing process.
  • a protective film having appropriate hardness can be formed using the protective film composition, thus causing no problem related to the breakage of the protective film upon cutting of the wafer.
  • the protective film composition has superior applicability on the wafer, it can be widely utilized in the dicing process during the fabrication of semiconductor devices having an increased degree of integration.
  • the present invention is directed to a protective film composition for wafer dicing, including at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer, and a solvent, such as water or a mixture of water and an organic solvent.
  • a protective film composition for wafer dicing including at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer, and a solvent, such as water or a mixture of water and an organic solvent.
  • At least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, and at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer may be contained at a weight ratio of 1:9 ⁇ 7:3, and the solvent may be contained in a range in which total viscosity of the composition is set to 10 ⁇ 100 cP.
  • the protective film composition for wafer dicing may further include 10 ⁇ 80 ppm of a water-soluble surfactant based on the total weight of the resin component of the composition.
  • Examples of a resin component used for a general protective film composition for wafer dicing include resin such as polyvinyl alcohol (PVA), polyethylene glycol (PEG) and cellulose, and water-soluble resin, such as polyacrylic acid (PAA) and so on.
  • resin such as polyvinyl alcohol (PVA), polyethylene glycol (PEG) and cellulose
  • water-soluble resin such as polyacrylic acid (PAA) and so on.
  • PAA polyacrylic acid
  • the water-soluble resin having a hydroxyl group or a carboxylic group is problematic in that it is weak to heat or may produce a crosslinked by-product upon pyrolysis.
  • polyethyloxazoline and polyvinylpyrrolidone have superior thermal stability and high water solubility.
  • the protective film composition according to the present invention comprises polyethyloxazoline or a mixture of polyethyloxazoline and polyvinylpyrrolidone as at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone.
  • polyethyloxazoline poly(2-ethyl-2-oxazoline) under the trade name of Aquazol, having high water solubility and superior thermal solubility.
  • TGA thermogravimetric analyzer
  • the weight reduction begins to occur at 350°C or higher and drastic decomposition occurs at about 380°C.
  • a crosslinked by-product is not produced in the course of decomposition, and thus defects insoluble in water are not formed.
  • polyvinylpyrrolidone has high water solubility and superior thermal stability.
  • weight reduction is measured using a TGA at a heating rate of 10 °C/min in a nitrogen atmosphere, the weight reduction begins to occur at about 300°C and drastic decomposition takes place at about 400°C.
  • a crosslinked by-product is not produced in the course of decomposition, and thus defects insoluble in water are not formed.
  • the protective film composition according to the present invention, at least one component selected from the group consisting of the water-soluble resin and the alcoholic monomer is used to enhance adhesiveness of the protective film to a substrate and adjust hardness of the protective film.
  • the water-soluble resin include polyvinyl alcohol, polyethylene glycol (PEG), polypropylene glycol (PPG), cellulose, polyacrylic acid (PAA) and so on
  • the alcoholic monomer include monoethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, cyclohexane diol, cyclohexane dimethanol, pentaerythritol, trimethylpropanol and so on.
  • polyvinyl alcohol which is the water-soluble resin
  • polyvinyl alcohol is highly soluble in water and has excellent adhesive force to a wafer.
  • adhesive force of the protective film composition for wafer dicing may be enhanced, thereby preventing the delamination of the protective film upon irradiation of a laser.
  • water solubility and storage stability after dissolution thereof vary depending on the degree of saponification and molecular weight thereof. In the case where the degree of saponification of polyvinyl alcohol is 100%, polyvinyl alcohol has poor water solubility and gels after being dissolved in water, and thus its viscosity increases over time.
  • polyvinyl alcohol having the degree of saponification of 87 ⁇ 90% may be used. Because polyvinyl alcohol having the degree of saponification of 87 ⁇ 90% does not change in viscosity over time, it may be used as a solution agent. Furthermore, solubility and stability over time of polyvinyl alcohol vary depending on the molecular weight thereof. When polyvinyl alcohol has the degree of polymerization of 500 ⁇ 2,000, solubility and storage stability are superior. Thus, in the present invention, the use of polyvinyl alcohol having the degree of saponification of 87 ⁇ 90% and the degree of polymerization of 500 ⁇ 2,000 is preferable.
  • polyvinyl alcohol has poor thermal stability, it is used in the form of a mixture with polyethyloxazoline and/or polyvinylpyrrolidone, having superior thermal stability, within a range that does not produce a crosslinked by-product which is insoluble in water, at 250°C or lower.
  • At least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone and at least one component selected from the group consisting of the water-soluble resin and the alcoholic monomer may be used at a weight ratio of 1:9 ⁇ 7:3, and preferably 3:7 ⁇ 7:3.
  • these components are used in the above range, thermal stability, adhesiveness to a wafer, and hardness of a protective film are manifested as desired.
  • the water-soluble surfactant plays a role in enhancing applicability of the composition and increasing storage stability.
  • the protective film generally used in the laser wafer dicing process may have a thickness of 1 ⁇ m or more. If the applicability of the protective film composition is poor, there occurs a difference in film thickness between the center of the wafer and the edge thereof, and thus process margin may be reduced. Thus, in the protective film composition according to the present invention, the water-soluble surfactant is added, thereby enhancing the applicability of the composition.
  • water-soluble surfactant examples include polyether modified alkylsiloxane, polyether modified polyalkylsiloxane, polyether modified polydimethylsiloxane having a hydroxyl group, polyether-polyester modified polyalkylsiloxane having a hydroxyl group, a non-ionic polyacrylic water-soluble surfactant, alcohol alkoxylate, and a polymeric fluorine-based water-soluble surfactant, which may be used alone or in combinations of two or more thereof.
  • the present inventors have found the fact that the water-soluble surfactant plays a role as a dispersant in the protective film composition such that the protective film composition does not gel over time.
  • the protective film composition according to the present invention has enhanced applicability and high storage stability, thanks to the use of the water-soluble surfactant.
  • the water-soluble surfactant may be used in an amount of 10 ⁇ 80 ppm based on the total weight of the resin component of the composition.
  • the properties of the protective film composition including applicability and storage stability become good, and also, thermal stability, adhesiveness to a wafer, and hardness of a protective film may be improved.
  • the solvent is water.
  • the solvent may be used in the form of a mixture of water and an organic solvent.
  • the organic solvent include isopropylalcohol, propyleneglycolmonomethylether acetate (PGMEA), propyleneglycolmonomethylether (PGME), and an alkyl carbonate such as butylene carbonate, propylene carbonate, glycerine carbonate or ethylene carbonate. These organic solvents may be used alone or in combinations of two or more thereof.
  • propyleneglycolmonomethylether has high miscibility in water enough to dissolve even at any mixing ratio with water.
  • propyleneglycolmonomethylether acetate has solubility of 16 g or less per 100 g of water and thus must be used in the above range.
  • alkyl carbonate such as butylene carbonate, propylene carbonate, glycerine carbonate or ethylene carbonate, having high polarity
  • storage stability and applicability may be favorably improved.
  • Ethylene carbonate is a solid at room temperature but dissolves well in water, and glycerine carbonate may be dissolved in water at any mixing ratio.
  • butylene carbonate and propylene carbonate have water solubilities of 10% and 25% or less respectively at room temperature, and thus must be used in the above ranges.
  • the solvent is added so that the total viscosity of the composition is set to 10 ⁇ 100 cP. If the viscosity of the protective film composition falls within the above range, superior applicability may be exhibited, and adhesiveness to a wafer and hardness of a protective film may be obtained as desired.
  • the protective film composition according to the present invention may further include at least one additive known in the art in order to improve performance.
  • the protective film composition for wafer dicing may further include a defoaming agent for inhibiting foaming of a solution agent, and examples of the defoaming agent include polysiloxane, polyalkylsiloxane, a fluorosilicone polymer and so on.
  • the present invention is directed to a semiconductor device manufactured using the protective film composition for wafer dicing.
  • the semiconductor device according to the present invention can be completely protected by the protective film even when the wafer is diced using a laser or a blade, and can be manufactured to have no defects thanks to ease of washing of the protective film.
  • ⁇ between 800 and less than 1000 nm/s
  • ⁇ between 500 and less than 800 nm/s
  • ⁇ number of detached lattices (between 1 and less than 5)
  • ⁇ number of detached lattices (between 5 and less than 10)

Abstract

Disclosed is a protective film composition for wafer dicing, comprising at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer, and a solvent, such as water or a mixture of water and an organic solvent.

Description

PROTECTIVE FILM COMPOSITION FOR WAFER DICING
The present invention relates to a protective film composition having superior thermal stability, which is used for a semiconductor dicing process.
In the fabrication of a semiconductor device, a wafer dicing process follows a semiconductor lamination process so that devices which are respectively arranged are separated by cutting the wafer along the boundary region called a street therebetween. After the cutting process, a chip manufacturing process is performed, thus completing a semiconductor product.
As the degree of integration of semiconductor devices increases, the width of the street is becoming narrower and also mechanical properties of a laminate are becoming poorer. So, the wafer dicing process is being changed to solve the above problems.
With an increase in the degree of integration of the devices, polyimide which is the main material in an insulating film at the uppermost location of the laminate may be broken or damaged in the course of the wafer dicing process. Thus, the wafer dicing process is changed from cutting of the wafer using a blade toward perforation of the wafer using a laser and then cutting thereof using a blade. Also, a process of cutting the wafer using only a laser may be employed. However, in the laser dicing process using a laser, fumes may be generated and may scatter due to the heat of the laser, thereby causing a problem that the upper surface of the wafer is contaminated.
Disclosed as known techniques for solving this problem is a process method including applying a water-soluble resin such as polyvinyl alcohol, polyethylene glycol or cellulose on the upper surface of a wafer to thus form a protective film and then radiating laser light.
However, even though such a method is used, silicon gas may be generated from the cut surface of the wafer due to the heat of laser light, undesirably delaminating the protective film of the wafer. Furthermore, fumes may be generated along with the silicon gas and thus may accumulate between the protective film in a delaminated state and the upper surface of the wafer. When the protective film of the wafer is subsequently washed with water, such fume deposits are not removed but remain as defects.
The water-soluble resin has poor thermal stability. Thus, upon irradiation of a laser in the laser wafer dicing process, internal heat may be generated, and the water-soluble resin such as polyvinyl alcohol may be pyrolyzed by such heat. Furthermore, during the pyrolysis, a crosslinking reaction may take place, and the resultant crosslinked material is not removed even by water washing after the laser wafer dicing process, but remains on the upper surface of the wafer.
Currently, the laser wafer dicing process typically includes perforating the wafer using a laser and then cutting the wafer using a blade. Upon cutting of the wafer using a blade, in the case where the protective film of the wafer has high hardness, it may break, and thereby impurities occurring upon cutting of the wafer may infiltrate interstices of the broken film. Because such impurities which are water-insoluble adhere to the upper surface of the wafer, they are not washed off with water and become defects.
Accordingly, the present invention has been made keeping in mind the above problems encountered in the related art, and an object of the present invention is to provide a protective film composition for wafer dicing, which has high thermal stability to thus prevent the production of a pyrolyzed crosslinked material due to irradiation of a laser in a dicing process, exhibits high adhesive force to a wafer to thus prevent the delamination of a protective film in a laser wafer dicing process, and forms a protective film having appropriate hardness so that the protective film is not broken even when the wafer is perforated by a laser and then cut using a blade.
The present invention provides a protective film composition for wafer dicing, including at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer, and a solvent, such as water or a mixture of water and an organic solvent.
According to the present invention, the protective film composition for wafer dicing has high thermal stability to thus prevent the production of a pyrolyzed crosslinked material due to irradiation of laser in a dicing process, and exhibits high adhesive force to a wafer to thus prevent the delamination of a protective film in a laser wafer dicing process. Also, a protective film having appropriate hardness can be formed using the protective film composition, thus causing no problem related to the breakage of the protective film upon cutting of the wafer. Furthermore, because the protective film composition has superior applicability on the wafer, it can be widely utilized in the dicing process during the fabrication of semiconductor devices having an increased degree of integration.
The present invention is directed to a protective film composition for wafer dicing, including at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer, and a solvent, such as water or a mixture of water and an organic solvent.
In the protective film composition according to the present invention, at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone, and at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer may be contained at a weight ratio of 1:9~7:3, and the solvent may be contained in a range in which total viscosity of the composition is set to 10~100 cP.
The protective film composition for wafer dicing may further include 10~80 ppm of a water-soluble surfactant based on the total weight of the resin component of the composition.
Examples of a resin component used for a general protective film composition for wafer dicing include resin such as polyvinyl alcohol (PVA), polyethylene glycol (PEG) and cellulose, and water-soluble resin, such as polyacrylic acid (PAA) and so on. Among them, the water-soluble resin having a hydroxyl group or a carboxylic group is problematic in that it is weak to heat or may produce a crosslinked by-product upon pyrolysis. However, as the water-soluble resin used in the composition according to the present invention, polyethyloxazoline and polyvinylpyrrolidone have superior thermal stability and high water solubility.
It is preferable that the protective film composition according to the present invention comprises polyethyloxazoline or a mixture of polyethyloxazoline and polyvinylpyrrolidone as at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone.
Known as an example of polyethyloxazoline is poly(2-ethyl-2-oxazoline) under the trade name of Aquazol, having high water solubility and superior thermal solubility. When weight reduction is measured using a thermogravimetric analyzer (TGA) at a heating rate of 10 ℃/min in a nitrogen atmosphere, the weight reduction begins to occur at 350℃ or higher and drastic decomposition occurs at about 380℃. However, a crosslinked by-product is not produced in the course of decomposition, and thus defects insoluble in water are not formed.
Also, polyvinylpyrrolidone has high water solubility and superior thermal stability. When weight reduction is measured using a TGA at a heating rate of 10 ℃/min in a nitrogen atmosphere, the weight reduction begins to occur at about 300℃ and drastic decomposition takes place at about 400℃. However, a crosslinked by-product is not produced in the course of decomposition, and thus defects insoluble in water are not formed.
In the protective film composition according to the present invention, at least one component selected from the group consisting of the water-soluble resin and the alcoholic monomer is used to enhance adhesiveness of the protective film to a substrate and adjust hardness of the protective film. Examples of the water-soluble resin include polyvinyl alcohol, polyethylene glycol (PEG), polypropylene glycol (PPG), cellulose, polyacrylic acid (PAA) and so on, and examples of the alcoholic monomer include monoethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, cyclohexane diol, cyclohexane dimethanol, pentaerythritol, trimethylpropanol and so on.
As such, polyvinyl alcohol, which is the water-soluble resin, is highly soluble in water and has excellent adhesive force to a wafer. Thus, when polyvinyl alcohol is used, adhesive force of the protective film composition for wafer dicing may be enhanced, thereby preventing the delamination of the protective film upon irradiation of a laser. Furthermore, as for polyvinyl alcohol, water solubility and storage stability after dissolution thereof vary depending on the degree of saponification and molecular weight thereof. In the case where the degree of saponification of polyvinyl alcohol is 100%, polyvinyl alcohol has poor water solubility and gels after being dissolved in water, and thus its viscosity increases over time. Hence, polyvinyl alcohol having the degree of saponification of 87~90% may be used. Because polyvinyl alcohol having the degree of saponification of 87~90% does not change in viscosity over time, it may be used as a solution agent. Furthermore, solubility and stability over time of polyvinyl alcohol vary depending on the molecular weight thereof. When polyvinyl alcohol has the degree of polymerization of 500~2,000, solubility and storage stability are superior. Thus, in the present invention, the use of polyvinyl alcohol having the degree of saponification of 87~90% and the degree of polymerization of 500~2,000 is preferable.
However, because polyvinyl alcohol has poor thermal stability, it is used in the form of a mixture with polyethyloxazoline and/or polyvinylpyrrolidone, having superior thermal stability, within a range that does not produce a crosslinked by-product which is insoluble in water, at 250℃ or lower.
In the protective film composition according to the present invention, at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone and at least one component selected from the group consisting of the water-soluble resin and the alcoholic monomer may be used at a weight ratio of 1:9~7:3, and preferably 3:7~7:3. When these components are used in the above range, thermal stability, adhesiveness to a wafer, and hardness of a protective film are manifested as desired.
In the protective film composition according to the present invention, the water-soluble surfactant plays a role in enhancing applicability of the composition and increasing storage stability.
The protective film generally used in the laser wafer dicing process may have a thickness of 1 ㎛ or more. If the applicability of the protective film composition is poor, there occurs a difference in film thickness between the center of the wafer and the edge thereof, and thus process margin may be reduced. Thus, in the protective film composition according to the present invention, the water-soluble surfactant is added, thereby enhancing the applicability of the composition. Examples of the water-soluble surfactant include polyether modified alkylsiloxane, polyether modified polyalkylsiloxane, polyether modified polydimethylsiloxane having a hydroxyl group, polyether-polyester modified polyalkylsiloxane having a hydroxyl group, a non-ionic polyacrylic water-soluble surfactant, alcohol alkoxylate, and a polymeric fluorine-based water-soluble surfactant, which may be used alone or in combinations of two or more thereof.
Also, the present inventors have found the fact that the water-soluble surfactant plays a role as a dispersant in the protective film composition such that the protective film composition does not gel over time. Hence, the protective film composition according to the present invention has enhanced applicability and high storage stability, thanks to the use of the water-soluble surfactant.
In the protective film composition according to the present invention, the water-soluble surfactant may be used in an amount of 10~80 ppm based on the total weight of the resin component of the composition. When the water-soluble surfactant is used in the above range, the properties of the protective film composition including applicability and storage stability become good, and also, thermal stability, adhesiveness to a wafer, and hardness of a protective film may be improved.
In the protective film composition according to the present invention, the solvent is water. Alternatively, in order to increase the film thickness of the protective film composition or enhance applicability thereof, the solvent may be used in the form of a mixture of water and an organic solvent. Examples of the organic solvent include isopropylalcohol, propyleneglycolmonomethylether acetate (PGMEA), propyleneglycolmonomethylether (PGME), and an alkyl carbonate such as butylene carbonate, propylene carbonate, glycerine carbonate or ethylene carbonate. These organic solvents may be used alone or in combinations of two or more thereof.
As such, propyleneglycolmonomethylether has high miscibility in water enough to dissolve even at any mixing ratio with water. However, propyleneglycolmonomethylether acetate has solubility of 16 g or less per 100 g of water and thus must be used in the above range.
In particular, in the case where the alkyl carbonate such as butylene carbonate, propylene carbonate, glycerine carbonate or ethylene carbonate, having high polarity, is used as organic solvents, storage stability and applicability may be favorably improved.
Ethylene carbonate is a solid at room temperature but dissolves well in water, and glycerine carbonate may be dissolved in water at any mixing ratio. However, butylene carbonate and propylene carbonate have water solubilities of 10% and 25% or less respectively at room temperature, and thus must be used in the above ranges.
In the protective film composition according to the present invention, the solvent is added so that the total viscosity of the composition is set to 10~100 cP. If the viscosity of the protective film composition falls within the above range, superior applicability may be exhibited, and adhesiveness to a wafer and hardness of a protective film may be obtained as desired.
The protective film composition according to the present invention may further include at least one additive known in the art in order to improve performance.
Especially, the protective film composition for wafer dicing may further include a defoaming agent for inhibiting foaming of a solution agent, and examples of the defoaming agent include polysiloxane, polyalkylsiloxane, a fluorosilicone polymer and so on.
In addition, the present invention is directed to a semiconductor device manufactured using the protective film composition for wafer dicing. The semiconductor device according to the present invention can be completely protected by the protective film even when the wafer is diced using a laser or a blade, and can be manufactured to have no defects thanks to ease of washing of the protective film.
A better understanding of the present invention may be obtained through the following examples which are set forth to illustrate, but are not to be construed as limiting the present invention.
EXAMPLES 1~10 and COMPARATIVE EXAMPLES 1~6: Preparation of Protective Film Composition for Wafer Dicing
EXAMPLE 1
Into a mixer equipped with a stirrer, 5 g of polyethyloxazoline (Aquazol, degree of polymerization (DP): 50) and 5 g of polyvinyl alcohol (PVA) (DP: 500, degree of saponification (DS): 87~90%) were added, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 2
Into a mixer equipped with a stirrer, 3 g of polyethyloxazoline (Aquazol, DP: 50), 3 g of polyvinylpyrrolidone (DP: 1200) and 4 g of PVA (DP: 1700, DS: 87~90%) were added, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 3
Into a mixer equipped with a stirrer, 3 g of polyethyloxazoline (Aquazol, DP: 50), 3 g of polyvinylpyrrolidone (DP: 1200) and 4 g of PVA (DP: 1700, DS: 87~90%) were added, and a mixture of water and propyleneglycolmonomethylether (PGME) at a ratio of 70/30 (w/w) was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 4
Into a mixer equipped with a stirrer, 7 g of polyethyloxazoline (Aquazol, DP: 500) and 3 g of PVA (DP: 500, DS: 87~90%) were added, and a mixture of water and PGME at a ratio of 70/30 (w/w) was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 5
Into a mixer equipped with a stirrer, 3 g of polyethyloxazoline (Aquazol, DP: 500) and 7 g of PVA (DP: 1700, DS: 87~90%) were added, and a mixture of water and PGME at a ratio of 70/30 (w/w) was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 6
Into a mixer equipped with a stirrer, 5 g of polyethyloxazoline (Aquazol, DP: 50) and 5 g of PVA (DP: 500, DS: 87~90%) were added, a surfactant (BYK-337, available from BYK) and a defoaming agent (BYK-025, available from BYK) were respectively added in an amount of 30 ppm based on the total weight of polyethyloxazoline and PVA, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 7
Into a mixer equipped with a stirrer, 3 g of polyethyloxazoline (Aquazol, DP: 50), 3 g of polyvinylpyrrolidone (DP: 1200) and 4 g of PVA (DP: 1700, DS: 87~90%) were added, a surfactant (BYK-337, available from BYK) and a defoaming agent (BYK-025, available from BYK) were respectively added in an amount of 30 ppm based on the total weight of polyethyloxazoline, polyvinylpyrrolidone and PVA, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 8
Into a mixer equipped with a stirrer, 2 g of polyethyloxazoline (Aquazol, DP: 50), 2 g of polyvinylpyrrolidone (DP: 1200) and 6 g of PVA (DP: 1700, DS: 87~90%) were added, a surfactant (BYK-337, available from BYK) and a defoaming agent (BYK-025, available from BYK) were respectively added in an amount of 30 ppm based on the total weight of polyethyloxazoline, polyvinylpyrrolidone and PVA, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 9
Into a mixer equipped with a stirrer, 7 g of polyethyloxazoline (Aquazol, DP: 500) and 3 g of PVA (DP: 500, DS: 87~90%) were added, a surfactant (BYK-337, available from BYK) and a defoaming agent (BYK-025, available from BYK) were respectively added in an amount of 30 ppm based on the total weight of polyethyloxazoline and PVA, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
EXAMPLE 10
Into a mixer equipped with a stirrer, 3 g of polyethyloxazoline (Aquazol, DP: 500), 7 g of PVA (DP: 1700, DS: 87~90%), 1 g of triethyleneglycol (TEG) and 0.3 g of butylene carbonate were added, a surfactant (BYK-337, available from BYK) and a defoaming agent (BYK-025, available from BYK) were respectively added in an amount of 30 ppm based on the total weight of polyethyloxazoline and PVA, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
COMPARATIVE EXAMPLE 1
Into a mixer equipped with a stirrer, 10 g of PVA (DP: 1700, DS: 87~90%) was added, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
COMPARATIVE EXAMPLE 2
Into a mixer equipped with a stirrer, 9 g of PVA (DP: 1700, DS: 87~90%) and 1 g of polyethyleneglycol (PEG) (weight average molecular weight: 700) were added, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
COMPARATIVE EXAMPLE 3
Into a mixer equipped with a stirrer, 9 g of PVA (DP: 1700, DS: 87~90%) and 1 g of pentaerythritol were added, and a mixture of water and PGME at a ratio of 70/30 (w/w) was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
COMPARATIVE EXAMPLE 4
Into a mixer equipped with a stirrer, 8 g of PVA (DP: 1700, DS: 87~90%), 1 g of PEG (weight average molecular weight: 700) and 1 g of pentaerythritol were added, and a mixture of water and PGME at a ratio of 70/30 (w/w) was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
COMPARATIVE EXAMPLE 5
Into a mixer equipped with a stirrer, 9 g of PVA (DP: 1700, DS: 87~90%) and 1 g of PEG (weight average molecular weight: 700) were added, a surfactant (BYK-337, available from BYK) was added in an amount of 300 ppm based on the total weight of PVA and PEG, and water was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
COMPARATIVE EXAMPLE 6
Into a mixer equipped with a stirrer, 9 g of PVA (DP: 1700, DS: 87~90%) and 1 g of pentaerythritol were added, a surfactant (BYK-337, available from BYK) was added in an amount of 300 ppm based on the total weight of PVA and pentaerythritol, and a mixture of water and PGME at a ratio of 70/30 (w/w) was added as a solvent so that the viscosity of the solution is 60 cP, after which stirring was performed at room temperature and 500 rpm for 1 hour, thus preparing a protective film composition for wafer dicing.
TEST EXAMPLE 1: Measurement of Strip Rate
A sample of each of the examples and comparative examples was applied through spin coating on a silicon oxide substrate having a size of 4 inches while adjusting the spin rate (rpm) such that a resulting film had a thickness of 1 ㎛ after being dried at 110℃ for 15 min, thus forming a protective film. The rate of stripping the protective film in water was measured using a DRM. The measurement unit is represented by the film thickness removed per second. The test results are shown in Table 1 below.
◎: 1000 nm/s or more
○: between 800 and less than 1000 nm/s
△: between 500 and less than 800 nm/s
×: less than 500 nm/s
TEST EXAMPLE 2: Measurement of Applicability
A sample of each of the examples and comparative examples was applied through spin coating on a silicon oxide substrate having a size of 4 inches while adjusting the spin rate (rpm) such that a resulting film had a thickness of 1 ㎛ after being dried at 110℃ for 15 min, thus forming a protective film. Thereafter, film thickness was measured at the center of the wafer and locations spaced apart from the center of the wafer at a distance of 2 cm and 4 cm in all directions, and the standard deviation thereof was determined, thus evaluating the applicability of the protective film composition. The test results are shown in Table 1 below.
◎: 1% or less
○: exceeding 1% but not more than 2%
△: exceeding 2% but not more than 4%
×: exceeding 4%
TEST EXAMPLE 3; Measurement of Pencil Hardness
A sample of each of the examples and comparative examples was applied through spin coating on a silicon oxide substrate having a size of 4 inches while adjusting the spin rate (rpm) such that a resulting film had a thickness of 1 ㎛ after being dried at 110℃ for 15 min, thus forming a protective film. Thereafter, the hardness of the protective film to pencil was measured according to JID D 0202. The test results are shown in Table 1 below.
TEST EXAMPLE 4: Measurement of Adhesiveness
A sample of each of the examples and comparative examples was applied through spin coating on a silicon oxide substrate having a size of 4 inches while adjusting the spin rate (rpm) such that a resulting film had a thickness of 1 ㎛ after being dried at 110℃ for 15 min, thus forming a protective film. Thereafter, a cross-cut test (taping test) was performed according to JIS K5600-5-6. The test results are shown in Table 1 below.
◎: number of detached lattices (0)
○: number of detached lattices (between 1 and less than 5)
△: number of detached lattices (between 5 and less than 10)
×: number of detached lattices (10 or more)
TEST EXAMPLE 5: Measurement of Thermal Stability
A sample of each of the examples and comparative examples was applied through spin coating on a silicon oxide substrate having a size of 4 inches while adjusting the spin rate (rpm) such that a resulting film had a thickness of 1 ㎛ after being dried at 110℃ for 15 min, thus forming a protective film. Thereafter, the protective film was allowed to stand in a hot air oven at 250℃ for 10 min, and then whether it was washed off with water was checked, in order to confirm whether a pyrolyzed crosslinked material insoluble in water was produced by heat. The test results are shown in Table 1 below.
◎: completely stripped state
○: presence of fine particles
△: presence of a large amount of non-stripped portions
×: non-stripped state
TEST EXAMPLE 6: Measurement of Storage Stability
While the samples of the examples and comparative examples were stored at room temperature, the viscosity and applicability were measured every week, thereby checking whether the properties changed over time. The test results are shown in Table 1 below.
◎: stable for 36 weeks or longer
○: stable for 18 weeks or longer
△: stable for 8 weeks or longer
×: stable for less than 8 weeks
Table 1
Figure PCTKR2009002727-appb-T000001

Claims (11)

  1. A protective film composition for wafer dicing, comprising at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone; at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer; and a solvent including water or a mixture of water and an organic solvent.
  2. The protective film composition according to claim 1, wherein the at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone and the at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer are used at a weight ratio of 1:9~7:3, and the solvent is used so that a total viscosity of the composition is 10~100 cP.
  3. The protective film composition according to claim 1, further comprising a water-soluble surfactant which is used in an amount of 10~80 ppm based on a total weight of a resin component of the composition.
  4. The protective film composition according to claim 1, wherein the at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone is polyethyloxazoline.
  5. The protective film composition according to claim 1, wherein the water-soluble resin is selected from the group consisting of polyvinyl alcohol, polyethylene glycol (PEG), polypropylene glycol (PPG), cellulose and polyacrylic acid (PAA), and the alcoholic monomer is selected from the group consisting of monoethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, propylene glycol, cyclohexane diol, cyclohexane dimethanol, pentaerythritol and trimethylpropanol.
  6. The protective film composition according to claim 1, wherein the at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer is polyvinyl alcohol which has a degree of saponification of 87~90% and a degree of polymerization of 500~2,000.
  7. The protective film composition according to claim 1, wherein the at least one resin selected from the group consisting of polyethyloxazoline and polyvinylpyrrolidone is polyethyloxazoline, and the at least one component selected from the group consisting of a water-soluble resin and an alcoholic monomer is polyvinyl alcohol which has a degree of saponification of 87~90% and a degree of polymerization of 500~2,000.
  8. The protective film composition according to claim 3, wherein the water-soluble surfactant is one or more selected from the group consisting of polyether modified alkylsiloxane, polyether modified polyalkylsiloxane, polyether modified polydimethylsiloxane having a hydroxyl group, polyether-polyester modified polyalkylsiloxane having a hydroxyl group, a non-ionic polyacrylic water-soluble surfactant, alcohol alkoxylate, and a polymeric fluorine-based water-soluble surfactant.
  9. The protective film composition according to claim 1, wherein the solvent is the mixture of water and the organic solvent, and the organic solvent is one or more selected from the group consisting of isopropylalcohol, propyleneglycolmonomethylether acetate (PGMEA), propyleneglycolmonomethylether (PGME), butylene carbonate, propylene carbonate, glycerine carbonate, and ethylene carbonate.
  10. The protective film composition according to claim 9, wherein the organic solvent is one or more selected from the group consisting of butylene carbonate, propylene carbonate, glycerine carbonate, and ethylene carbonate.
  11. A semiconductor device, manufactured using the protective film composition of any one of claims 1 to 10.
PCT/KR2009/002727 2008-05-29 2009-05-22 Protective film composition for wafer dicing WO2009145526A2 (en)

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