WO2016105134A1 - Composition de résine adhésive pour semi-conducteur, film adhésif, film de découpage en puces/fixation de puces, et dispositif semi-conducteur - Google Patents

Composition de résine adhésive pour semi-conducteur, film adhésif, film de découpage en puces/fixation de puces, et dispositif semi-conducteur Download PDF

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Publication number
WO2016105134A1
WO2016105134A1 PCT/KR2015/014199 KR2015014199W WO2016105134A1 WO 2016105134 A1 WO2016105134 A1 WO 2016105134A1 KR 2015014199 W KR2015014199 W KR 2015014199W WO 2016105134 A1 WO2016105134 A1 WO 2016105134A1
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WO
WIPO (PCT)
Prior art keywords
resin
semiconductor
adhesive
epoxy resin
film
Prior art date
Application number
PCT/KR2015/014199
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English (en)
Korean (ko)
Inventor
김희정
김정학
이광주
김세라
김영국
남승희
한지호
Original Assignee
주식회사 엘지화학
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 KR1020150184155A external-priority patent/KR101799499B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201580005577.4A priority Critical patent/CN106414641B/zh
Priority to JP2016549579A priority patent/JP6348981B2/ja
Publication of WO2016105134A1 publication Critical patent/WO2016105134A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds

Definitions

  • the present invention relates to a resin composition for semiconductor bonding, an adhesive film, a dicing die bonding film, and a semiconductor device.
  • a step of heating at a high temperature is applied.
  • a method of heating and mounting the entire package by infrared refluorination, vapor phase reflow, solder thickening, or the like is used.
  • the heating step of this Ko Un because it exposes the entire semiconductor package in more than 200 ° C
  • the silver, water present in the semiconductor package may cause it and "package crack or reflow crack by this vaporized explosively vaporized.
  • the content of the curing agent and the epoxy may be increased to decrease the hygroscopicity of the cured product.
  • the modulus of the adhesive after curing increases, making it difficult to relieve the stress.
  • the content of the thermosetting resin in the adhesive is excessively increased or the content of the curing agent is lowered in order to alleviate the strength of the semiconductor, it is difficult to give proper adhesion to the substrate after curing, and in this case, delaminat ion due to low adhesion Will result.
  • Patent Document 1 Korean Patent Publication No. 2013-0016123
  • Patent Document 2 Korean Registered Patent No. 0889101
  • the present invention has excellent mechanical properties such as physical properties, heat resistance and impact resistance suitable for a package of a multi-layered laminate structure of a semiconductor chip, and has high adhesive strength, and can prevent peeling phenomenon or reflow cracking of a dicing die-bonding film. It is for providing a resin composition for semiconductor bonding.
  • the present invention has excellent mechanical properties such as high mechanical properties, heat resistance and layer resistance, and high adhesion, and prevents peeling phenomenon or ripple crack between substrate, semiconductor wafer and / or dicing die-bonding film, and thus higher lamination. It is to provide a dicing die-bonding film that can implement the structure.
  • the present invention has excellent mechanical properties, such as physical properties, heat resistance and impact resistance suitable for the package of the multi-stage laminated structure of the semiconductor chip, high adhesion, and can prevent peeling phenomenon, reflow cracking, etc. of the dicing die-bonding film.
  • the present invention also provides an adhesive film for a semiconductor that does not substantially generate voids even when exposed to high temperature conditions applied during a semiconductor manufacturing process for a long time.
  • this invention is providing the semiconductor device containing the said adhesive film for semiconductors.
  • thermoplastic resin having a moisture absorption of 165 hours exposure at 85 ° C and 853 ⁇ 4RH conditions or less;
  • a curing agent including a phenol resin wherein the content of the biphenyl-based epoxy resin in solid content is 5 wt% to 25 wt%, and a resin composition for semiconductor bonding is provided.
  • Solid content of the resin composition for semiconductor bonding means a solid component except for water or other solvents that may be optionally included in the resin composition.
  • the biphenyl epoxy resin means an epoxy resin having a biphenyl structure as a repeating unit, and specifically, the biphenyl epoxy
  • the resin may comprise a biphenyl novolac epoxy resin.
  • the biphenyl novolac epoxy resin may have a weight average molecular weight of 1,000 or more and 10,000, and may also have a softening point of 5 (rc to ioo ° c).
  • the epoxy resin may include a general resin in addition to the biphenyl-based epoxy resin described above.
  • the epoxy resin is bisphenol A epoxy resin, bisphenol F epoxy resin, cresol novolac epoxy resin, phenol noblock epoxy resin, tetrafunctional epoxy resin, triphenol methane type epoxy resin, alkyl modified triphenol methane type epoxy resin, naphthalene type epoxy It may further include at least one resin selected from the group consisting of a resin, a dicyclopentadiene type epoxy resin and a dicyclopentadiene modified phenol type epoxy resin.
  • the softening point of the epoxy resin may be 50 ° C to 100 ° C.
  • the epoxy resin may have an average epoxy equivalent of 100 to 5,000.
  • the average epoxy equivalent may be obtained based on the weight ratio and epoxy equivalent of each epoxy resin included in the epoxy resin.
  • the phenolic resin may have a hydroxyl equivalent of 80 g / eq ⁇ 300 g / eq and a softening point of 50 ° C to 150 ° C.
  • the thermoplastic resin is polyimide, polyether imide, polyester imide, polyamide, polyether sulfone, polyether ketone, polyolefin, polyvinyl chloride, phenoxy, semi-butadiene acrylonitrile copolymer rubber and (meth) It may include one or more polymer resins selected from the group consisting of acrylate resins.
  • the (meth) acrylate-based resin may be a (meth) acrylate-based resin including a (meth) acrylate-based repeating unit including an epoxy-based functional group and having a glass transition temperature of ⁇ 10 ° C. to 20 ° C.
  • the (meth) acrylate-based resin may include 0.1 wt% to 10 wt% of a (meth) acrylate-based repeating unit including an epoxy-based functional group.
  • the resin composition for semiconductor bonding may include 50 to 1,000 parts by weight of the thermoplastic resin and 30 to 700 parts by weight of the curing agent relative to 100 parts by weight of the epoxy resin.
  • the curing agent may further include at least one compound selected from the group consisting of an amine curing agent, and an acid anhydride curing agent.
  • the semiconductor adhesive resin composition may further include at least one curing catalyst selected from the group consisting of phosphorus compounds, boron compounds, phosphorus-boron compounds and imidazole compounds.
  • the semiconductor adhesive resin composition may further include at least one additive selected from the group consisting of a coupling agent and an inorganic layer release agent.
  • the semiconductor adhesive resin composition may further include 10 to 90% by weight of an organic solvent.
  • the content of the biphenyl-based epoxy resin in the solid content of the resin composition for semiconductor bonding may be 5% by weight to 25% by weight.
  • cured material of the said resin composition for semiconductor bonding is provided.
  • the moisture absorption rate of the adhesive film at 165 hours exposure at 85 ° C. and 85% RH conditions may be less than or equal to 1.5 wt%.
  • the adhesive film may have a thickness of 1 to 50 kPa.
  • a base film An adhesive layer formed on the base film; And an adhesive worm formed on the adhesive layer and including the resin composition for semiconductor bonding.
  • the hygroscopicity of the adhesive layer at 165 hours exposure at 85 ° C. and 85% RH conditions may be less than 1.5% by weight.
  • the tackifier may include an ultraviolet curable pressure sensitive adhesive or a heat curable pressure sensitive adhesive.
  • the base film has a thickness of 10 to 200, the adhesive layer is
  • the adhesive film has a thickness of 10 im to 500, and the adhesive film has a thickness of 1 to 50 m.
  • a semiconductor device including a structure in which the first semiconductor element and the adherend are bonded through an adhesive film may be provided. When the semiconductor device is cured at 10CTC to 200 ° C, or 120 to 180t, the area where the adhesive film and the first semiconductor element are in contact with each other or the void area generated inside the adhesive film may be less than or equal to.
  • the semiconductor device when the semiconductor device is cured at 100 ° C. to 200 ° C., or at 120 ° to 180 ° C. for at least 30 minutes, or 30 minutes to 5 hours, the surface where the adhesive film and the crab semiconductor device contact each other, or the inside of the adhesive film.
  • the area of the void (void) generated in the may be less than 1%.
  • the adherend may be a substrate, an insulating layer, or a second semiconductor device.
  • the present invention has excellent mechanical properties such as physical properties, heat resistance and impact resistance suitable for a package of a multi-layered laminate structure of a semiconductor chip, and has high adhesive strength, and can prevent peeling phenomenon or reflow cracking of a dicing die-bonding film.
  • a resin composition for semiconductor bonding can be provided.
  • the present invention has excellent mechanical properties such as high mechanical properties, heat resistance and layer resistance, and high adhesion, and prevents peeling phenomenon or repullow cracking between the substrate, semiconductor wafer and / or dicing die-bonding film, Dicing die-bonding film capable of realizing a laminated structure, excellent mechanical properties such as physical properties, heat resistance and layer toughness, suitable for the package of the multi-stacked structure of the semiconductor chip, and has high adhesive strength.
  • thermoplastic resin having a moisture absorption of 165 hours exposure at 85 ° C and 853 ⁇ 4RH conditions or less; Biphenyl epoxy Epoxy resins containing resins; And a curing agent including a phenol resin; wherein the content of the biphenyl epoxy resin in solids is 5% by weight to 25% by weight, and a resin composition for semiconductor bonding is provided.
  • the present inventors conducted a study to solve the problem that the dicing die-bonding film is broken or peeled off due to the vapor pressure during the reflow mounting, the reflow crack occurs, the biphenyl-based together with a thermoplastic resin having a low moisture absorption rate
  • a curing agent including an epoxy resin and a phenol resin containing an epoxy resin in a specific content is mixed, it has excellent mechanical properties such as high mechanical properties, heat resistance and layer resistance, and has high adhesive strength. It was confirmed through experiments that the resin composition for semiconductor bonding which can prevent etc. was completed and completed invention.
  • the resin composition for semiconductor bonding of the embodiment may have low moisture absorption even after long-term exposure to high temperature and high humidity conditions after a high temperature curing process. As a result, the peeling phenomenon between the substrate and the adhesive may be prevented after the reflow process of the semiconductor manufacturing process.
  • the measured moisture absorption may be 1.5 weight 3 ⁇ 4> or less.
  • Curing in the silver may be carried out for at least 30 minutes, or 30 minutes to 5 hours.
  • the content of the biphenyl-based epoxy resin in the solid content of the resin composition for semiconductor bonding of the embodiment may be 5% by weight to 25% by weight.
  • the biphenyl-based epoxy resin is contained in a specific content, it controls the degree of curing and other physical properties while maintaining the low hygroscopic properties of the resin composition for semiconductor bonding of the embodiment and serves to relieve the strength of the final adhesive film In this way, it is possible to prevent a delaminat phenomenon between the substrate and the adhesive in the reflow process after moisture absorption in the semiconductor packaging process.
  • the content of the biphenyl-based epoxy resin in the solid content of the resin composition for semiconductor bonding of the embodiment is less than 5% by weight, it is not possible to sufficiently reduce the moisture absorption rate of the resin composition for semiconductor bonding of the embodiment, between the substrate and the adhesive film It may be difficult to prevent delamination or reflow cracking.
  • the hardened structure is not dense, it is not possible to impart the layered heat resistance and strength to the final adhesive or adhesive layer This may cause low adhesion with the substrate, which may cause peeling phenomenon or reflow cracking between the substrate and the adhesive film.
  • the content of the solid content increase biphenyl-based epoxy resin of the resin composition for semiconductor bonding of the embodiment is more than 25% by weight of the adhesive film prepared from the composition for a long time at high temperature exposure of the inside of the adhesive film or the adhesive film and the adherend
  • a large number of voids at the interface can significantly reduce the reliability of the manufacturing process and the quality of the final product.
  • the content of the biphenyl-based epoxy resin in the solid content of the resin composition for semiconductor bonding of the embodiment is more than 25% by weight, 100 ° C to 200 ° C in the state that the adhesive film prepared from the composition is included in the semiconductor device
  • a large number of voids may occur in the contact surface between the adhesive film and the semiconductor device or inside the adhesive film.
  • the biphenyl epoxy resin may include a biphenyl novolac epoxy resin.
  • the softening point of the biphenyl-based epoxy resin may be 5 (rc to i (xrc). If the softening point of the epoxy resin is too low, the adhesive strength of the resin composition for semiconductor adhesion may be increased, thereby reducing chip pick-up after dicing. When the softening point of the epoxy resin is too high, the fluidity of the semiconductor adhesive resin composition may be lowered and the adhesive force of the adhesive film manufactured from the semiconductor adhesive resin composition may be lowered.
  • the said resin composition for semiconductor bonding In order to increase the epoxy resin, bisphenol A epoxy resin, bisphenol F epoxy resin, cresol novolac epoxy resin, phenol novolac epoxy resin, tetrafunctional epoxy resin, triphenol methane type epoxy resin, alkyl, together with the biphenyl epoxy resin It may further include at least one resin selected from the group consisting of a modified triphenol methane type epoxy resin, a naphthalene type epoxy resin, a dicyclopentadiene type epoxy resin and a dicyclopentadiene modified phenol type epoxy resin.
  • the softening point of the epoxy resin further included may also be 50 ° C to 100 ° C.
  • the epoxy resin may have an average epoxy equivalent of 100 to 1,000.
  • the average epoxy equivalent may be obtained based on the weight ratio and epoxy equivalent of each epoxy resin included in the epoxy resin.
  • the resin composition for semiconductor bonding may include a phenol resin having a softening point of 60 ° C. or higher, or 60 ° C. to 150 ° C., or 90 ° C. to 120 ° C. as a curing agent.
  • the phenol resin having a softening point of 6 rc or more is used, the semiconductor adhesive resin composition may have sufficient heat resistance, strength, and adhesiveness after curing. If the softening point of the phenol resin is too low, the semiconductor adhesive resin composition is cured. In addition, if the softening point of the phenolic resin is too high, the fluidity of the semiconductor adhesive resin composition may be increased, thereby creating voids inside the adhesive in the actual semiconductor manufacturing process. It can greatly reduce the reliability and quality of the product.
  • the phenol resin may have a hydroxyl equivalent of 80 g / eq to 300 g / eq.
  • the resin composition for the implementation of the semiconductor adhesive may comprise a thermoplastic resin moisture absorption rate is not more than 1.5% by weight during 165 hours of exposure at 85 ° C and 85% RH condition. The moisture absorption rate can be determined by the ratio of the weight before exposure for 165 hours under the 851 and 85% RH conditions.
  • the resin composition for semiconductor bonding of the embodiment may have a lower moisture absorption as a whole, The amount of water to be included is insignificant, and peeling phenomenon, reflow cracking, etc. of the dicing die-bonding film can be prevented.
  • thermoplastic resin examples are not limited, but for example, polyimide, polyether imide, polyester imide, polyamide, polyether sulfone, polyether keron, polyolefin, polyvinyl chloride, phenoxy, reactive butadiene acryl Nitrile copolymer rubber, (meth) acrylate type resin, 2 or more types of these mixtures, or these 2 or more types of copolymers are mentioned.
  • the (meth) acrylate-based resin is a (meth) acrylate-based resin containing a (meth) acrylate-based repeating unit including an epoxy-based functional group and having a glass transition temperature of ⁇ 10 ° C to 20 ° C. Can be.
  • the resin for semiconductor bonding of the above embodiment according to the (meth) acrylate-based resin comprising a (meth) acrylate-based repeating unit including the epoxy-based functional group and having a glass transition temperature of -io ° C to 2 (rc)
  • the composition can be used for bonding semiconductors, bonding components contained in semiconductors, or for semiconductor packages, and can secure high impact resistance when multi-stage stacking of ultrathin wafers, and can improve electrical properties after semiconductor manufacturing.
  • An adhesive film or an adhesive film for a semiconductor package may be provided
  • the epoxy-based functional group may be substituted with one or more repeating units forming a main chain of the (meth) acrylate-based resin.
  • the epoxy-based functional group may include an epoxy group or a glycidyl group. (Meth) acrylate-based repeating unit containing the epoxy-based functional group
  • (Meta) acrylate-based resin containing more than 14% by weight may have a glass transition temperature of -10 ° C to 20 ° C, or -5 ° C to 15 ° C.
  • the semiconductor adhesive resin composition may have sufficient fluidity, the final adhesive film can secure a high adhesive force, the resin for semiconductor bonding It is easy to manufacture in the form of a thin film using a composition.
  • the resin composition for semiconductor bonding of the embodiment may include 50 to 1,000 parts by weight of the thermoplastic resin and 30 to 700 parts by weight of the curing agent relative to 100 parts by weight of the epoxy resin. If the content of the thermoplastic resin is too small compared to the epoxy resin, the modulus after curing of the resin composition rises rapidly, and thus it is difficult to expect a stress relaxation effect between the substrate and the wafer. In addition, if the content of the thermoplastic resin is too high compared to the epoxy resin, the viscosity of the composition increases at B-st age, resulting in poor adhesion to the substrate during the die attach process, and difficulty in removing voids during the curing process. Can be degraded. If the content of the curing agent including the phenol resin is too small compared to the epoxy resin it may be difficult to ensure a layered heat resistance.
  • the content of the curing agent including the phenolic resin is too high compared to the epoxy resin, even if the curing is completed, the unreacted phenol group may remain and increase the hygroscopicity. Accordingly, the substrate and the adhesive may be absorbed in the reflowing process after the absorption in the semiconductor packaging process. It may cause peeling of the liver.
  • the content of the epoxy resin including the biphenyl-based epoxy resin in the semiconductor adhesive resin composition may be determined according to the final product, for example, 3 to 30 weight 3 ⁇ 4>, or 5 to 25 of the solid content of the total composition Weight percent.
  • the curing agent may further include at least one compound selected from the group consisting of an amine curing agent and an acid anhydride curing agent.
  • the amount of the curing agent may be appropriately selected in consideration of physical properties of the adhesive film to be finally manufactured, for example, 10 to 700 parts by weight, or 30 to 300 parts by weight based on 100 parts by weight of the epoxy resin.
  • the semiconductor adhesive resin composition may further include a curing catalyst.
  • the curing catalyst plays a role of promoting the action of the curing agent and curing of the resin composition for semiconductor bonding, and a curing catalyst known to be used in the manufacture of a semiconductor adhesive film or the like can be used without great limitation.
  • the curing catalyst may be one or more selected from the group consisting of a phosphorus compound boron compound, a phosphorus-boron compound and an imidazole compound.
  • the amount of the curing catalyst used may be appropriately selected in consideration of the physical properties of the final adhesive film, for example, based on a total of 100 parts by weight of the total of the epoxy resin, the (meth) acrylate resin, and the phenol resin. 0.5 to 10 parts by weight can be used.
  • the semiconductor adhesive resin composition may further include 10 to 90% by weight of an organic solvent.
  • the content of the organic solvent may be determined in consideration of the physical properties of the resin composition for semiconductor bonding or the physical properties or manufacturing processes of the final adhesive film.
  • the semiconductor adhesive resin composition may further include at least one additive selected from the group consisting of a coupling agent and an inorganic layer release agent.
  • a coupling agent and an inorganic layering agent are not limited, and any component known to be used in an adhesive for semiconductor packaging may be used without great limitation.
  • the adhesive film containing the cured product of the above-mentioned resin composition for semiconductor bonding could be provided.
  • the cured product of the resin composition for semiconductor bonding may be prepared into an adhesive film by curing (drying) at a high temperature, for example, 50 ° C. or higher, or 70 ° C. or higher, or 70 ° C. to 25C C.
  • the adhesive film may be used in a semiconductor device.
  • the adhesive film has excellent mechanical properties such as physical properties, heat resistance, and layer resistance suitable for a package of a multilayer structure of a semiconductor chip, and has high adhesive strength. It is possible to prevent the delamination phenomenon, reflow cracks, and the like, and may not substantially generate voids even when exposed to high temperature conditions applied during the semiconductor manufacturing process for a long time.
  • the adhesive film is a thermoplastic resin having a moisture absorption of 1.5% by weight or less when exposed to 165 hours at 85 ° C and 85% RH conditions; An epoxy resin containing a biphenyl epoxy resin; And a curing agent including a phenol resin, wherein the content of the biphenyl-based epoxy resin in the adhesive film is 5 wt% to
  • thermoplastic resin Epoxy resin containing biphenyl-type epoxy resin
  • a curing agent including a phenol resin may be present in the adhesive film in a crosslinked state with each other.
  • Hygroscopicity may be less than 1.5 weight 3 ⁇ 4.
  • the adhesive film may have a thickness of 1 to 50.
  • the base film An adhesive layer formed on the base film; And an adhesive layer formed on the adhesive layer and including the above-described resin composition for semiconductor adhesion.
  • the dicing die-bonding film may have excellent mechanical properties such as high mechanical properties, heat resistance, and layer resistance, and high adhesion, and exhibit low moisture absorption. The peeling phenomenon, reflow crack, etc. of the dicing die-bonding film by vaporization of water can be prevented.
  • the type of the base film included in the dicing die-bonding film is not particularly limited, for example, a plastic film or metal foil known in the art can be used.
  • the base film may be low density polyethylene, linear polyethylene, medium density polyethylene, high density polyethylene, ultra low density polyethylene, random copolymer of polypropylene, block copolymer of polypropylene, homopolypropylene, polymethylpentene , Ethylene-vinyl acetate copolymer, ethylene-methacrylic acid copolymer, ethylene-methyl methacrylate copolymer, ethylene-ionomer copolymer, ethylene-vinyl alcohol copolymer, polybutene, copolymer of styrene, or two thereof And mixtures of species or more.
  • the meaning of the base film including a mixture of two or more polymers in the above means that a film having a structure in which two or more layers of films including each of the aforementioned polymers are stacked or a single layer containing two or more of the aforementioned polymers includes both films. do.
  • the thickness of the base film is not particularly limited, usually 10 kPa 200 im, preferably 50 / m to 180 im thick. If the thickness is less than 10, there is a risk of unstable control of the cut depth in the dicing process, if the thickness exceeds 200 / zm, a large amount of burrs in the dicing process or elongation is lowered There is a fear that the expansion process may not be performed correctly.
  • the base film may be subjected to conventional physical or chemical treatments such as matt treatment, corona discharge treatment, primer treatment or crosslinking treatment, as necessary.
  • the pressure-sensitive adhesive layer may include an ultraviolet curable pressure sensitive adhesive or a heat curable pressure sensitive adhesive.
  • ultraviolet curable pressure sensitive adhesive ultraviolet rays are irradiated from the base film side to raise the cohesion force and the glass transition temperature of the pressure sensitive adhesive, and in the case of the heat curable pressure sensitive adhesive, the adhesive force is lowered by applying a temperature.
  • the ultraviolet curable pressure sensitive adhesive may include a (meth) acrylate resin, an ultraviolet curable compound, a photoinitiator, and a crosslinking agent.
  • the weight average molecular weight may be 100,000 to 1.5 million, preferably 200,000 to 1 million. If the weight average molecular weight is less than 100,000, the coating property or the coarsening force is lowered, and residues may remain on the adherend during peeling, or adhesive breakage may occur. In addition, when the weight average molecular weight exceeds 1.5 million, the base resin interferes with reaction of the ultraviolet curable compound, and there is a concern that the peeling force may not be reduced efficiently.
  • Such (meth) acrylate-based resins are, for example,
  • (meth) acrylic acid ester monomer may be a copolymer of a (meth) acrylic acid ester monomer and a crosslinkable functional group-containing monomer.
  • examples of the (meth) acrylic acid ester monomer include alkyl (meth) acrylate, and more specifically, monomers having an alkyl group having 1 to 12 carbon atoms, pentyl (meth) acrylate, n-butyl
  • examples of the crosslinkable functional group-containing monomer include one or more kinds of hydroxy group-containing monomers, carboxyl group-containing monomers, or nitrogen-containing monomers.
  • examples of the compound containing a hydroxyl group at this time include 2-hydroxyethyl (meth) acrylate or 2—hydroxypropyl.
  • (Meth) acrylate etc. are mentioned, As an example of a carboxyl group containing compound, (meth) acrylic acid etc. are mentioned, As an example of a nitrogen containing monomer, (meth) acrylonitrile, N-vinyl pyridone, or N Vinyl caprolactam and the like, but is not limited thereto.
  • the (meth) acrylate resin may further include vinyl acetate, styrene or an acrylonitrile carbon-carbon double bond-containing low molecular weight compound and the like from the viewpoint of improving other functionalities such as compatibility.
  • the type of the UV-curable compound is not particularly limited, and for example, a polyfunctional compound having a weight average molecular weight of about 500 to 300, 000 (ex. Polyfunctional urethane acrylate, polyfunctional acrylate monomer or oligomer, etc.) Can be used.
  • a polyfunctional compound having a weight average molecular weight of about 500 to 300, 000 ex. Polyfunctional urethane acrylate, polyfunctional acrylate monomer or oligomer, etc.
  • the average person skilled in the art can easily select the appropriate compound according to the intended use.
  • the content of the ultraviolet curable compound may be 5 parts by weight to 400 parts by weight, preferably 10 parts by weight to 200 parts by weight, based on 100 parts by weight of the base resin described above. If the content of the UV-curable compound is less than 5 parts by weight, there is a risk that the lowering of the adhesive strength after curing, the pick-up properties may be reduced, if the content exceeds 400 parts by weight, the cohesive strength of the adhesive before UV irradiation is insufficient, or peeling with the release film or the like There is a possibility that it may not be easily performed.
  • the type of the photoinitiator is also not particularly limited, it is possible to use a general initiator known in the art, the content may be from 0.05 parts to 20 parts by weight based on 100 parts by weight of the ultraviolet curable compound.
  • the content of the photoinitiator is less than 0.05 part by weight, curing reaction by ultraviolet irradiation There is a possibility that the pick-up property is deteriorated due to the lack of, and when exceeding 20 parts by weight, the crosslinking reaction occurs in a short unit during the curing process, or an uncured UV-curable compound is generated, which causes residue on the surface of the adherend, or peeling force after curing There exists a possibility that it may become low too much and pick-up property may fall.
  • the type of crosslinking agent included in the adhesive portion for imparting the adhesive force and the compaction force is not particularly limited, and conventional compounds such as an isocyanate compound, an aziridine compound, an epoxy compound, or a metal chelate compound may be used.
  • the crosslinking agent may be included in an amount of 2 parts by weight to 40 parts by weight, preferably 2 parts by weight to 20 parts by weight, based on 100 parts by weight of the base resin. If the content is less than 2 parts by weight, there is a fear that the cohesive force of the pressure-sensitive adhesive is insufficient, if it exceeds 20 parts by weight, the adhesive strength before ultraviolet irradiation is insufficient, there is a fear that chip scattering and the like.
  • the adhesive layer may further include a tackifier such as a rosin resin, a terpene resin, a phenol resin, a styrene resin, an aliphatic petroleum resin, an aromatic petroleum resin, or an aliphatic aromatic copolymerized petroleum resin.
  • a tackifier such as a rosin resin, a terpene resin, a phenol resin, a styrene resin, an aliphatic petroleum resin, an aromatic petroleum resin, or an aliphatic aromatic copolymerized petroleum resin.
  • the method for forming the pressure-sensitive adhesive layer containing the above components on the base film is not particularly limited, and for example, a method of forming the pressure-sensitive adhesive layer by applying the pressure-sensitive adhesive composition of the present invention directly on the base film or on a peelable base material.
  • the pressure-sensitive adhesive composition may be applied to a pressure-sensitive adhesive layer once to produce a pressure-sensitive adhesive layer, and the method may be used to transfer the pressure-sensitive adhesive layer onto a base film using the peelable base material.
  • the method of applying and drying the pressure-sensitive adhesive composition is not particularly limited, and for example, a composition including each of the above components, as it is, or diluted in a suitable organic solvent, such as a comma coater, gravure coater, die coater or river coater
  • a suitable organic solvent such as a comma coater, gravure coater, die coater or river coater
  • a method of drying the solvent for 10 seconds to 30 minutes at a silver temperature of 6 (C to 200 ° C. It can also be used. aging) may be further performed.
  • the thickness of the adhesive layer is not particularly limited, but may be, for example, in the range of 10 to 500.
  • the adhesive layer is formed on the adhesive layer It may include an adhesive film for a semiconductor of the above-described embodiment.
  • the content of the adhesive film for semiconductor includes all the above-mentioned matters.
  • the thickness of the adhesive layer is not particularly limited, but may be, for example, in the range of 1 m to 100 ⁇ , or 3 ⁇ to 50.
  • the dicing die-bonding film may further include a release film formed on the adhesive.
  • the release film that can be used include one or more kinds of polyethylene terephthalate film, polytetrafluoroethylene film, polyethylene film, polypropylene film, polybutene film, polybutadiene film, vinyl chloride copolymer film or polyimide film and the like.
  • the surface of the release film as described above may be a release treatment of one kind or two or more kinds of alkylide, silicone, fluorine, unsaturated ester, polyolefin, wax or the like, of which the alkyd, silicon or fluorine, etc. Release agent of is preferable.
  • the release film may be generally formed in a thickness of about 10 to 500 ⁇ , preferably about 20 kPa to about 200, but is not limited thereto.
  • the method for producing the above-mentioned dicing die-bonding film is not particularly limited, and for example, a method of sequentially forming an adhesive part, an adhesive part and a release film on a base film, or a dicing film (base film + adhesive part) And after separately manufacturing a release film formed with a die-bonding film or an adhesive portion, a method for laminating it may be used.
  • the lamination method is not particularly limited, hot lamination or lamination press method can be used, and the hot lamination method is preferable in view of the possibility of double continuous process and efficiency.
  • the hot laminating method is from 0.1 Kgf / cuf to ⁇ in the silver io ° c to ioo ° c
  • Kgf / cirf may be carried out at a pressure, but is not limited thereto.
  • the die-die die-bonding film On the other hand, according to another embodiment of the invention, the die-die die-bonding film; And a wafer stacked on at least one surface of the dicing die-bonding film; a pre-processing step of partially or partially dividing the semiconductor wafer. Irradiating ultraviolet rays to the base film of the pretreated semiconductor wafer, A method of dicing a semiconductor wafer can be provided, comprising picking up individual chips separated by the division of the semiconductor wafer.
  • the dicing method of the semiconductor wafer may further include expanding the semiconductor wafer after the pretreatment step. In this case, a process of irradiating ultraviolet rays to the base film of the expanded semiconductor wafer and picking up individual chips separated by the division of the semiconductor wafer is followed.
  • a semiconductor device including a spherical coupling between the first semiconductor element and the adherend through the adhesive film of the above embodiment can be provided.
  • the adhesive film of the above-described embodiment has excellent mechanical properties such as physical properties, heat resistance, and impact resistance suitable for the package of the multi-layered structure of the semiconductor chip, and has high adhesive strength, and the peeling phenomenon or ripple of the dicing die-bonding film Low cracking and the like may be prevented, and voids may not be substantially generated even when exposed to high temperature conditions applied in the semiconductor manufacturing process for a long time.
  • the adhesive film of the above-described embodiment it is possible to manufacture a semiconductor device having a more stable and robust multi-stage structure, and to secure a strong bond between the first semiconductor element and the adherend even in a multi-stage laminated structure process.
  • the semiconductor device is cured at 100 ° C. to 200 ° C., or 120 to 180 ° C., the area where the adhesive film and the first semiconductor element contact each other or the area of voids generated inside the adhesive film is It may be less than 1%.
  • voids may not substantially occur in the contact surface of the adhesive film and the semiconductor element or inside the adhesive film, and occur in the contact surface of the adhesive film and the first semiconductor element or in the adhesive film.
  • the area of the void (void) can be less than 1%.
  • the first semiconductor device may be the first semiconductor device immediately neighboring the substrate in the semiconductor packaging process.
  • the adherend may be a substrate, an insulating layer, or a second semiconductor device.
  • the substrate includes a substrate or a lead frame, and specifically, a conventionally known substrate such as a printed wiring board can be used as the substrate.
  • a metal lead frame or glass epoxy such as a Cu lead frame or a 42Al loy lead frame can be used.
  • an organic substrate comprising BT (bismaleimide-triazine), polyimide, or the like can be used.
  • the fresh semiconductor device may further include a second semiconductor device of the same type or different type as the first semiconductor device in addition to the first semiconductor device and the adherend bonded through the adhesive film.
  • the lamination may generally proceed to a process of manufacturing a package, and the lamination and wire bonding may be performed by the required number of layers. After laminating
  • Specific embodiments of the invention are described in more detail in the following examples. However, the following examples are merely to illustrate specific embodiments of the invention, the content of the present invention is not limited by the following examples. [Examples and Comparative Examples: Production of Resin Composition for Semiconductor Adhesion and Adhesive Film for Semiconductor]
  • biphenyl novolak epoxy resin (NC-3000-H, Nippon Chemical Co., Ltd., epoxy equivalent: 288 g / eq, softening point: 65 50 g, bisphenol A novolak epoxy resin (MF8080EK80, JSI Japan, epoxy equivalent: 218) g / eq, softening point: 65 ° C) 50 g, phenolic resin KPH-3075 (Kotong emulsification, hydroxyl equivalent: 180 g / eq, softening point 65 ° C), thermoplastic acrylate resin KG-3015 (85 ° C and 85% Hygroscopicity at 165 hours exposure under RH conditions: 1.2 wt%) 482 g, curing accelerator 2-phenyl-4-methyl-5-dihydroxymethyl imidazole (2P4MHZ, Shikoku Kasei) 0.5 g, coupling agent gamma-glycidoxy 2 g of cipropyl trimethoxy silane (K
  • the resin composition solution for semiconductor bonding prepared above was applied onto a polyethylene terephthalate film (thickness 38) and dried at 130 ° C. for 3 minutes to obtain an adhesive film having a thickness of 20 / t.
  • Examples 2-5 The resin composition solution for semiconductor bonding prepared above was applied onto a polyethylene terephthalate film (thickness 38) and dried at 130 ° C. for 3 minutes to obtain an adhesive film having a thickness of 20 / t. Examples 2-5
  • a semiconductor adhesive film was prepared in the same manner as in Example 1, except that a resin composition solution for preparing a semiconductor adhesive (concentration of 20% by weight of methyl ethyl ketone) was prepared using the components and contents shown in Table 1 below. Comparative Examples 1 to 3
  • a semiconductor adhesive film was prepared in the same manner as in Example 1, except that a resin composition solution for a semiconductor adhesive (concentration of 20% by weight of methyl ethyl ketone) was prepared using the components and contents shown in Table 1 below.
  • a resin composition solution for a semiconductor adhesive concentration of 20% by weight of methyl ethyl ketone
  • KPH-3075 Xyloc A novolac phenolic resin (Kotong emulsification, hydroxyl equivalent: 180 g / eq, softening point 65 ° C)
  • SHB-1101 Bisphenol A novolac phenolic resin (Shin A T & C, hydroxyl equivalent: 118g / eq, softening point: 110 ° C)
  • NC-3000-H biphenyl novolac epoxy resin (epoxy equivalent 180 g / eq, softening point 65 ° C)
  • MF8080EK20 bisphenol A epoxy resin (epoxy equivalent 218 g / eq, softening point 60 ° C)
  • KG-3015 Acrylate resin (3% by weight of glycidylmethacrylic repeating unit; Glass transition temperature: Moisture absorption rate at 165 hours exposure at 10 ° C, 85 ° C and 85% RH conditions: 1.2 wt. )
  • acrylate-based resin (3% by weight of glycidylmethacrylic repeating unit; glass transition temperature: moisture absorption at 165 hours exposure at 30 ° C, 85 ° C and 85% RH conditions: 1.7 wt% )
  • KG-3060 acrylate-based resin (2% by weight of glycidylmethacrylic repeating unit, glass transition degree: moisture absorption at exposure time of 165 hours at 5 ° C, 85 ° C and 85% RH conditions: 0.8 wt)
  • thermosetting product was cut to prepare a specimen of a cube having a length of 20 mm 3 and a width of 4 mm 3.
  • the ultraviolet curable pressure-sensitive adhesive composition was applied on a polyester film having a thickness of 38 ⁇ m after the release treatment so as to have a thickness of 100 ⁇ m after drying, and dried at 1 KTC for 3 minutes.
  • the dried adhesive layer was laminated on a polyolefin film having a thickness of 100 to prepare a dicing film.
  • An adhesive film having a multilayer structure for dicing die bonding was prepared by laminating the adhesive layer obtained in the above process and the adhesive films obtained in the examples and the comparative examples, respectively.
  • a wafer having a thickness of 80 ⁇ coated with a dioxide film was cut into a size of 6 (laminated under rc conditions, 10 ⁇ * 10 ⁇ (horizontal * vertical)) together with a dicing die-bonding film prepared by the method described in Experimental Example 2 above. The specimen was prepared.
  • a wafer of thickness 80 coated with a dioxide film was laminated at 60 ° C with a dicing die-bonding film prepared by the method described in Experimental Example 2, and cut into 10 mm * 10 mm (horizontal * vertical) specimens. was prepared.
  • each specimen is SAT (Scan Acoust ic) Tomograph) was used to measure the number of specimens in which the void area in the adhesive layer was observed to be greater than 13 ⁇ 4. Observation of the voids was based on the results of imaging the specimen measured in transmission mode using soni fer in the state of immersing the specimen in distilled water.
  • the adhesive film prepared in Examples 1 to 5 has a moisture absorption rate of 1.40 wt% or less even after exposure to 165 hours at 85 ° C and 85% RH conditions, and reflowed after high temperature curing and moisture absorption. It was confirmed that no peeling phenomenon occurred between the substrate and the adhesive during the process.
  • the adhesive film prepared in Examples 1 to 5 is the substrate and the adhesive layer even when exposed to high temperature conditions of 100 ° C or more, for example, 125 ° C to 175 ° C for a long time that can be actually applied in the multi-stage lamination process of the semiconductor It was confirmed that voids did not occur in the interface between the liver or inside the adhesive layer.
  • the adhesive film of Comparative Example 1 was found to contain an acrylate-based resin having a low moisture absorption rate and a moisture absorption rate of 1.64 wt% after 165 hours of exposure at 851: and 85% RH conditions, and after high temperature curing and moisture absorption. It was confirmed that the peeling phenomenon occurred between the substrate and the adhesive during the reflow process. This may be due to the fact that the adhesive film of Comparative Example 1 contains a biphenyl novolac epoxy resin that can adjust the adhesive hygroscopicity in a low content, for example, less than about 3 weight 3 ⁇ 4.
  • the adhesive film of Comparative Example 2 includes an acrylate-based resin having a relatively high moisture absorption and does not include a biphenyl novolac epoxy resin as an epoxy resin, after 165 hours of exposure at 85 ° C. and 853 ⁇ 4 conditions.
  • the moisture absorption rate was 1.80 3 ⁇ 4, and it was confirmed that the peeling phenomenon between the substrate and the adhesive occurred greatly during the reflow process after high temperature curing and moisture absorption.
  • the adhesive film of Comparative Example 2 generated a large number of voids in the interface between the substrate and the adhesive layer or inside the adhesive layer when exposed to a high temperature condition of Kxrc or higher, which can be actually applied in the multi-stage lamination process.
  • the adhesive film of Comparative Example 3 contained a biphenyl novolak epoxy resin, but has a relatively high moisture absorption .
  • the moisture absorption rate is 1.63 wt3 ⁇ 4> after 165 hours exposure at 85 ° C. and 85% RH, and the peeling phenomenon between the substrate and the adhesive occurs during the reflow process after high temperature curing and moisture absorption. Confirmed.
  • the adhesive film of Comparative Example 4 contains more than 25% biphenyl novolac epoxy resin, the moisture absorption rate after 165 hours exposure at 85 ° C and 85% RH conditions Although it was 1.22, it was confirmed that the peeling phenomenon occurred between the substrate and the adhesive in the reflow process after the high temperature curing and moisture absorption /
  • the composition of the adhesive film of Comparative Example 4 was not divided into the components that play the role of the complete material, and the moisture absorption rate was Although it is lowered, it has a high modulus after curing, and it does not seem to realize the effect of relaxation of the stress between the substrate and the chip.
  • the adhesive film of Comparative Example 4 generated a large number of voids (vo id) in the interface between the substrate and the adhesive layer or inside the adhesive layer when exposed to a high temperature condition of locrc or more that can be actually applied in the multi-stage lamination process.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Die Bonding (AREA)

Abstract

La présente invention concerne une composition de résine adhésive pour semi-conducteur, la composition contenant : une résine thermoplastique ayant un faible taux d'absorption d'humidité; une résine époxyde comprenant une résine époxyde à base de biphényle; et un durcisseur comprenant une résine phénol, la teneur de la résine époxyde à base de biphényle dans les matières solides étant de 5 % en poids à 25 % en poids, un film adhésif comprenant un matériau durci de la composition de résine adhésive pour semi-conducteur, un film de découpage en puces/fixation de puces comprenant un film de base, une couche adhésive formée sur le film de base, et une couche de liaison formée sur la couche adhésive et contenant la composition de résine adhésive pour semi-conducteur, et un dispositif semi-conducteur comprenant le film adhésif.
PCT/KR2015/014199 2014-12-24 2015-12-23 Composition de résine adhésive pour semi-conducteur, film adhésif, film de découpage en puces/fixation de puces, et dispositif semi-conducteur WO2016105134A1 (fr)

Priority Applications (2)

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CN201580005577.4A CN106414641B (zh) 2014-12-24 2015-12-23 用于接合半导体的粘合性树脂组合物、粘合膜、切割晶片接合膜以及半导体装置
JP2016549579A JP6348981B2 (ja) 2014-12-24 2015-12-23 半導体接着用樹脂組成物、接着フィルム、ダイシングダイボンディングフィルムおよび半導体装置

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KR10-2014-0188717 2014-12-24
KR20140188717 2014-12-24
KR10-2015-0184155 2015-12-22
KR1020150184155A KR101799499B1 (ko) 2014-12-24 2015-12-22 반도체 접착용 수지 조성물, 접착 필름, 다이싱 다이본딩 필름 및 반도체 장치

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KR20040048364A (ko) * 2002-12-02 2004-06-09 닛토덴코 가부시키가이샤 접착제 조성물, 접착 필름 및 이를 사용하는 반도체 장치
KR20080009699A (ko) * 2006-03-31 2008-01-29 신닛뽄세이테쯔 카부시키카이샤 고강도 스프링용 열처리 강
KR20090113204A (ko) * 2008-04-25 2009-10-29 주식회사 엘지화학 에폭시계 조성물, 접착 필름, 다이싱 다이본딩 필름 및 반도체 장치
KR20100034726A (ko) * 2008-09-24 2010-04-01 주식회사 엘지화학 접착제 조성물, 접착 필름, 다이싱 다이본딩 필름, 반도체 웨이퍼 및 반도체 장치

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Publication number Priority date Publication date Assignee Title
KR20020075426A (ko) * 2000-02-15 2002-10-04 히다치 가세고교 가부시끼가이샤 접착제 조성물, 그 제조 방법, 이것을 이용한 접착 필름,반도체 탑재용 기판 및 반도체 장치
KR20040048364A (ko) * 2002-12-02 2004-06-09 닛토덴코 가부시키가이샤 접착제 조성물, 접착 필름 및 이를 사용하는 반도체 장치
KR20080009699A (ko) * 2006-03-31 2008-01-29 신닛뽄세이테쯔 카부시키카이샤 고강도 스프링용 열처리 강
KR20090113204A (ko) * 2008-04-25 2009-10-29 주식회사 엘지화학 에폭시계 조성물, 접착 필름, 다이싱 다이본딩 필름 및 반도체 장치
KR20100034726A (ko) * 2008-09-24 2010-04-01 주식회사 엘지화학 접착제 조성물, 접착 필름, 다이싱 다이본딩 필름, 반도체 웨이퍼 및 반도체 장치

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