WO2019203572A1 - Composition adhésive pour connexion de circuit à semi-conducteurs et film adhésif contenant celle-ci - Google Patents

Composition adhésive pour connexion de circuit à semi-conducteurs et film adhésif contenant celle-ci Download PDF

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Publication number
WO2019203572A1
WO2019203572A1 PCT/KR2019/004651 KR2019004651W WO2019203572A1 WO 2019203572 A1 WO2019203572 A1 WO 2019203572A1 KR 2019004651 W KR2019004651 W KR 2019004651W WO 2019203572 A1 WO2019203572 A1 WO 2019203572A1
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Prior art keywords
resin
group
adhesive film
formula
adhesive
Prior art date
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PCT/KR2019/004651
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English (en)
Korean (ko)
Inventor
김주현
김정학
남승희
이광주
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020190043931A external-priority patent/KR102204964B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201980006175.4A priority Critical patent/CN111448276B/zh
Priority to EP19789001.5A priority patent/EP3693434A4/fr
Priority to JP2020526595A priority patent/JP6983461B2/ja
Priority to US16/769,786 priority patent/US11834415B2/en
Publication of WO2019203572A1 publication Critical patent/WO2019203572A1/fr

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    • 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
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • 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
    • C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
    • C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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
    • C09J7/00—Adhesives in the form of films or foils

Definitions

  • This invention relates to the adhesive composition for semiconductor circuit connections, and the adhesive film for semiconductors.
  • thermocompression bonding technology is mainly applied for such bump bonding, wherein the heat curing property of the adhesive in the thermocompression bonding technology affects the package manufacturing processability and the package reliability.
  • Non-conductive paste (NCP) in the form of paste was developed as an adhesive to fill each TSV layer, but the bumps became narrower and the filling became more difficult. , is being developed by a non-conductive, film (Non-conduct ive Fi lm, NCF) implemented in the form of a film in order to overcome them.
  • NCF Non-conduct ive Fi lm
  • thermocompression bonding for bump bonding the adhesive should be rapidly cured at high temperature, and at room temperature, the adhesive should be cured to have good storage stability.
  • catalysts play an important role in the control of the degree of cure, and a reform of thermal latent catalyst is being made. 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • the present invention is to provide an adhesive composition for semiconductor circuit connection that can be cured and cured in a short time under high temperature during thermocompression bonding and has excellent storage stability at room temperature.
  • this invention is providing the adhesive film containing the said adhesive composition for semiconductor circuit connections.
  • thermoplastic resin In the present specification, a thermoplastic resin; Thermosetting resins; Curing agent; And a compound of the following Chemical Formula 1, a resin composition for semiconductor bonding is provided.
  • 3 ⁇ 4 is hydrogen, an alkyl group having 1 to 1 carbon atoms, or an aryl group having 6 to 20 carbon atoms (size 1), 3 ⁇ 4 is an organic functional group including a hydrogen bondable functional group, and 3 ⁇ 4 is hydrogen or halogen Or an alkyl group having 1 to 10 carbon atoms, or an aryl group having 0 to 20 carbon atoms (0111). It is 1-4 in substitution numbers.
  • 3 ⁇ 4 is hydrogen or benzene group
  • 3 ⁇ 4 may be a hydroxyl group, carboxyl group, carbonyl group, formyl group, or amine group.
  • the resin composition for semiconductor bonding is the thermoplastic resin; Thermosetting resin; Curing agent; And 0.1 to 15 parts by weight of the compound of Formula 1 relative to 100 parts by weight of the total compound of Formula 1.
  • thermoplastic resin is polyimide, polyether imide, polyester imide, polyamide, polyether sulfone, polyether ketone, polyolefin, polyvinyl chloride, phenoxy, reactive butadiene acrylonitrile copolymer rubber and (meth) acrylate At least one polymer selected from the group consisting of resins It may contain a resin.
  • the thermosetting resin may include at least one selected from the group consisting of a solid epoxy resin and a liquid epoxy resin.
  • the adhesive film for semiconductors containing the resin composition for semiconductor adhesives mentioned above is provided.
  • an adhesive composition for a semiconductor circuit connection and an electrodeposition film for a semiconductor which can be cured for a short time under high temperature during thermocompression bonding and have excellent storage stability at room temperature, can be provided.
  • thermoplastic resin Thermosetting resins
  • Curing agent a resin composition for semiconductor bonding comprising a compound of formula (1).
  • 3 ⁇ 4 is hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms
  • R 2 is an organic functional group including a hydrogen bondable functional group
  • 3 ⁇ 4 is hydrogen, halogen, or carbon number. It is an alkyl group of 1 to 10, or an aryl group having 6 to 20 carbon atoms
  • n is 1 to 4 in the number of substitution of 3 ⁇ 4. 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • the present inventors have conducted a study on the components that can be used in the adhesion or packaging of semiconductor devices, the composition or adhesive film containing the compound of the formula (1) is applied as a material for the semiconductor circuit connection, high temperature during thermocompression bonding It was confirmed through experiments that it can be cured within a short time under excellent storage stability at room temperature, and completed the invention.
  • the compound of Formula 1 may include an organic functional group including a hydrogen bondable functional group at 3 ⁇ 4 to delay the curing reaction through deactivation of the catalyst at room temperature at which hydrogen bonding is applied, and at a curing temperature or higher during thermocompression bonding. The hydrogen bond is broken and the catalyst can be activated.
  • the resin composition for semiconductor bonding of the embodiment may have a property of curing at a high speed at a high speed and long-term storage stability at room temperature.
  • 3 ⁇ 4 is hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms (group # 0111),
  • An organic functional group including a hydrogen bondable functional group 3 ⁇ 4 is hydrogen, a halogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms (group #A! And II may be 1 to 4 with a substitution number of 3 ⁇ 4.
  • 3 ⁇ 4 is hydrogen or benzene group
  • 3 ⁇ 4 may be a hydroxyl group carboxyl group, carbonyl group, formyl group, or amine group.
  • the said resin composition for semiconductor bonding is the said thermoplastic resin; Thermosetting resin; Curing agent; And 0.1 to 15 parts by weight of the compound of Formula 1, or 0.5 to 10 parts by weight, based on 100 parts by weight of the total compound of Formula 1.
  • thermoplastic resin Thermosetting resins; Curing agent; And when the weight of the compound of Formula 1 is too low relative to the total 100 parts by weight of the compound of Formula 1, the curing reaction is difficult to proceed and the degree of curing is not secured, or the reaction temperature section is wide, which causes rapid curing at a specific temperature. Can lose.
  • thermoplastic resin Thermosetting resins; Curing agent; And when the weight of the compound of Formula 1 is too high relative to the total amount of the compound of Formula 1 100 parts by weight, at room temperature: even some of the catalyst may be activated and the reaction may proceed, so the storage stability of the film may not be secured. 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • the adhesive composition for a semiconductor circuit connection in addition to the compound of Formula 1 described above may further comprise a thermoplastic value, a thermosetting resin and an inorganic filler.
  • the adhesive composition for a semiconductor circuit connection may include, in addition to the compound of the formula (1), a thermosetting resin, a thermoplastic resin, a curing agent, and an inorganic filler.
  • thermosetting resin As the thermosetting resin, the thermoplastic resin, and the curing agent included in the resin composition for semiconductor bonding of the embodiment, components commonly known in the field of adhesive compositions for semiconductor circuit connections may be applied.
  • thermosetting resin examples are not particularly limited, and for example, an epoxy resin may be preferably applied as the thermosetting resin.
  • the epoxy resin is a bisphenol epoxy resin, biphenyl epoxy resin, naphthalene epoxy resin, floren epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, trishydroxyphenylmethane epoxy It may be at least one selected from the group consisting of a resin, a tetraphenylmethane epoxy resin, a dicyclopentadiene type epoxy resin, and a dicyclopentadiene modified phenol type epoxy resin.
  • the bisphenol epoxy resin, bisphenol concave epoxy resin, bisphenol epoxy resin, bisphenol £ epoxy resin, hydrogenated bisphenol show epoxy resin, bisphenol new epoxy resin and the like.
  • thermosetting resin 10 to 35 10 to 35 with epoxy resin which is liquid under
  • the epoxy resin which is a solid phase can be used by mixing in a weight ratio of 1: 1.1 to 1: 5.
  • the content of the solid epoxy resin when the content of the solid epoxy resin is less than 0.1 weight ratio with respect to the liquid epoxy resin, the resin may excessively flow out during the die attach process, causing contamination, and the adhesiveness of the adhesive layer is strong, so that pickup characteristics are remarkably increased.
  • the content of the solid epoxy resin exceeds 5.0 weight ratio with respect to the liquid epoxy resin, it may be disadvantageous in terms of compatibility with the thermoplastic resin, reactivity. 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • the epoxy resin is a cresol novolak type epoxy resin having a softening point of 100 kkyeot with a biphenyl-type epoxy resin having a softening point of 50 ° to 100 0 ⁇ ⁇ It may further comprise at least one epoxy resin selected from the group consisting of bisphenol-show epoxy resin having a softening point of to 100 °C. At this time, the epoxy resin is To biphenyl epoxy resin having a softening point of from 1001 to 1001.
  • 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 type of the thermoplastic resin is also not particularly limited, and for example, polyimide, polyether imide, polyester imide, polyamide, polyether sulfone, polyether ketone, polyolefin, polyvinyl chloride, phenoxy, reactive It may include at least one polymer resin selected from the group consisting of butadiene acrylonitrile copolymer rubber and (meth) acrylate resin.
  • the thermoplastic resin has a glass transition temperature of -10 to 30 I: and a weight average molecular weight thereof of 200, 000 to 1,000, 000.
  • the acrylic resin is an epoxy group-containing acrylic copolymer, which may include 1 to 25% by weight, or 2 to 20% by weight, or 2.5 to 15% by weight of glycidyl acrylate or glycidyl methacrylate in the total weight. .
  • the content of the epoxy group in the (meth) acrylate resin is less than 1% by weight, the compatibility with the epoxy resin and the adhesive strength are not sufficient, and when the content exceeds 25% by weight 3 ⁇ 4 '', the rate of increase in viscosity due to curing is too fast. In the thermocompression process, solder bumps may not be sufficiently bonded and buried.
  • thermoplastic resin is used to control the flow of the composition, etc. 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • the curing agent may include at least one compound selected from the group consisting of an amine curing agent, and an acid anhydride curing agent.
  • a novolac phenol resin may be preferably applied as the curing agent.
  • the novolac phenolic resin has a chemical structure in which a ring is located between reactive functional groups. Due to these structural characteristics, the novolac-based phenolic resin can lower the hygroscopicity of the adhesive composition and can further improve the stability in the high temperature reflow process, thereby preventing the peeling phenomenon of the adhesive film or reflow cracking. Can play a role.
  • novolak-based phenol resins include novolak phenol resins, xylox novolak phenol resins, cresol novolak phenol resins, biphenyl novolak phenol resins, bisphenol yonovolak phenol resins, and bisphenol F novolak phenol resins. 1 or more types chosen from the group which consists of these.
  • the novolac phenol resin is To 150 ° (:, or 105 to 1501 :, or 70 ° 0 to 120 Having a softening point can work preferably.
  • the novolak-based phenol resin having the above softening point may have sufficient heat resistance, strength and adhesion after curing of the adhesive composition. However, if the softening point of the novolak-based phenolic resin is too high, the fluidity of the adhesive composition is lowered, so that an empty space (0 ′ (1)) is generated inside the adhesive in the actual semiconductor manufacturing process, thereby greatly reducing the reliability or quality of the final product.
  • the novolac phenol resin is To 300 It is preferable to have a hydroxyl equivalent and a softening point of -1501 :.
  • the content of the curing agent may be appropriately selected in consideration of physical properties of the adhesive film to be finally produced.
  • the curing agent may be used in 10 to 700 parts by weight or 30 to 300 parts by weight based on 100 parts by weight of the thermosetting resin. 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • 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 and the like can be used without great limitation.
  • the curing catalyst may be one or more selected from the group consisting of phosphorus compounds, boron compounds, phosphorus rod compounds, and imidazole compounds.
  • the amount of the curing catalyst used may be appropriately selected in consideration of physical properties of the adhesive film to be finally produced.
  • the resin composition for semiconductor bonding of the embodiment may further include an inorganic filler.
  • the inorganic filler includes at least one member selected from the group consisting of alumina, silica, barium sulfate, magnesium hydroxide, magnesium carbonate, magnesium silicate, magnesium oxide, calcium silicate, calcium carbonate, calcium oxide, aluminum hydroxide, aluminum nitride, and aluminum borate Inorganic particles may be applied.
  • Ion binders capable of improving reliance by ionic impurities may also be used as inorganic fillers.
  • the ion adsorbent includes magnesium hydroxide, magnesium carbonate, magnesium silicate, magnesium oxide such as magnesium oxide, calcium silicate, calcium carbonate, calcium oxide, alumina, aluminum hydroxide, aluminum nitride, aluminum borate whisker, zirconium mineral, and antimony bismuth mineral.
  • One or more inorganic particles selected from the group consisting of can be applied.
  • the inorganic heavy material is 0.01 to 10 Or 0.02 to 5.0 111, or 0.03 to 2.0, having an average particle diameter (based on the maximum outer diameter) can be preferably applied. If the particle diameter of the inorganic filler is too small, it can be easily aggregated in the adhesive composition. On the other hand, if the particle diameter of the inorganic filler is too large, damage to the semiconductor circuit and deterioration of adhesion of the adhesive film may be caused by the inorganic filler.
  • the content of the inorganic filler is 10 to 300 parts by weight or 15 to 250 parts by weight based on a total of 100 parts by weight of the thermosetting resin and the thermoplastic resin. 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • the adhesive composition for a semiconductor circuit connection may include 10 to 90 parts by weight of an organic solvent based on 100 parts by weight of the total of the thermosetting resin, the thermoplastic resin, and the inorganic filler.
  • the content of the organic solvent may be determined in consideration of the physical properties or the manufacturing process of the adhesive composition and the finally produced adhesive film.
  • the organic solvent may be at least one compound selected from the group consisting of esters, ethers, ketones, aromatic hydrocarbons, and sulfoxides.
  • the ester solvent is ethyl acetate, acetic acid-II-butyl, isobutyl acetate, formic acid amyl, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyrate, butyrate, methyl lactate, and ethyl lactate.
  • Gamma-butyrolactone, epsilon-caprolactone, delta_valerolactone alkyl oxyacetate e.g.
  • methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate e.g. methyl methoxyacetate, ethyl methoxyacetate, meth
  • 3 -oxypropionate alkyl esters for example, methyl 3-oxapropionate, ethyl 3-oxypropionate, etc.
  • the ether solvent is diethylene glycol dimethyl ether / tetrahydro-fu tube, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether methyl cellosolve acetate, 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • Ethyl cellosolve acetate diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol mono Methyl ether acetate, propylene glycol monoethyl ether acetate,
  • the ketone solvent may be methyl ethyl ketone, cyclonucleic acid temperature, cyclopentanone, 2-heptanone, 3-heptanone, methyl-2-pyrrolidone, or the like.
  • the aromatic hydrocarbon solvent may be toluene, xylene, anisole, limonene, or the like.
  • the sulfoxide solvent may be dimethyl sulfoxide or the like.
  • the adhesive composition for semiconductor circuit connection may contain a coupling agent.
  • the kind in particular of the said coupling agent is not restrict
  • the adhesive film for semiconductor circuit connection includes the adhesive composition for semiconductor circuit connection of the above-described embodiment, while exhibiting excellent storage stability at room temperature, it may exhibit a property that can be cured within a short time under high temperature during thermocompression bonding.
  • the adhesive film may have a melt viscosity of 3, 000 to 6,000 Pa ⁇ s £ l at a shear rate of 5 rad / s.
  • the melt viscosity may be defined as the lowest viscosity that can be obtained in the entire section of the adhesive film, not the viscosity at a specific temperature, for example, 5 rad / s using TA's advanced rheometric expansion system (ARES).
  • the viscosity value of the lowest value of the measured value by applying a temperature increase rate of 10 ° C / min at the shear rate of can be determined as the melt viscosity.
  • Melt viscosity may vary depending on the type of resin, the content of the acrylic resin, the type and content of the filler, the adhesive film is compared with the conventional adhesive film as it includes the adhesive composition for the semiconductor circuit connection of the above-described embodiment It may have a relatively low melt latency value.
  • the adhesive composition includes the compound of Formula 1 capable of hydrogen bonding in the molecular structure, and the compound of Formula 1 includes an organic functional group including a hydrogen bondable functional group to delay the temperature at which the reaction is initiated. As a result, the initiation point of the reaction setnset point is moved together, thereby having a relatively low melt viscosity compared to the conventional adhesive film. If the molecular structure does not include the catalyst of Formula 1 capable of hydrogen bonding, since there is no delay effect of the reaction, the reaction is started at a lower temperature and the melt viscosity is increased accordingly, resulting in a relatively high melt viscosity. It will have a value.
  • melt viscosity may affect the properties of the entire film, such as the possibility of bonding with the non-conductive film (NCF), the possibility of energization.
  • NCF non-conductive film
  • the adhesive film is left for 4 weeks at 25 ° C compared to the initial reaction peak after the change amount (AH) of the reaction peak after 20 weeks at 25 ° C compared to the initial melt viscosity at a shear rate of less than 20% or 5 rad / s
  • the amount of change in the melt viscosity may be 50% or less.
  • the AH peak change amount can be calculated by the change in the reaction peak value measured using a differential thermal analyzer (DSC), the change in the melt viscosity is the change in the melt viscosity value measured using the above-described minimum melt viscosity measurement method Can be calculated as
  • a support base material for supporting the film a resin film excellent in heat resistance and chemical resistance; A crosslinked film obtained by crosslinking a resin constituting the resin film; Alternatively, a film obtained by applying a silicone resin or the like to the surface of the resin film and performing a peeling treatment may be used.
  • polyolefin such as polyester, polyethylene, polypropylene, polybutene, polybutadiene, vinyl chloride, ethylene-methacrylic acid copolymer, ethylene vinyl acetate copolymer, polyester, polyimide, polyethylene Terephthalate, polyamide, polyurethane, etc. can be used.
  • the thickness of the supporting substrate is not particularly limited, but is 3 to 400 or 5 to 200. Or from 10 to 150.
  • the adhesive layer is made of the adhesive composition described above.
  • the content regarding the adhesive composition is as described above.
  • the adhesive layer may be interposed between the support substrate and the adhesive layer.
  • the adhesive layer those known in the art may be applied without particular limitation.
  • the kind of the protective film is not particularly limited, and a plastic film known in the art may be applied.
  • the protective film is 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 (1) 01 , 61; 1 ⁇ 6 6116), ethylene_vinyl acetate copolymer, ethylene-methacrylic acid copolymer, ethylene-methyl methacrylate copolymer, ethylten-ionomer copolymer, ethylten-vinyl alcohol copolymer, poly It may be a plastic film containing a resin such as a copolymer of butene and stilten.
  • the adhesive film for semiconductor circuit connection after mixing the adhesive composition and the component, and coating it on a support substrate to a predetermined thickness to form an adhesive layer 2019/203572 1 »(: 1 ⁇ 1 ⁇ 2019/004651
  • It may be prepared by a method of forming and drying the adhesive layer.
  • the adhesive film may be prepared by forming an adhesive layer on the support substrate and then laminating a protective film on the adhesive layer.
  • the adhesive film may be prepared by a method of sequentially forming an adhesive layer and a protective film on the adhesive layer after forming an adhesive layer on the support substrate.
  • the method for forming an adhesive layer on the support substrate is applied to the support substrate or the release film by a known means such as a comma coater, gravure coater, die coater, reverse coater by diluting the adhesive composition as it is or in an appropriate organic solvent. After, 60 To 200 A method of drying for 10 seconds to 30 minutes at temperature can be used.
  • an aging process for advancing a sufficient crosslinking reaction of the adhesive layer may be further performed.
  • the thickness of the adhesive layer may be appropriately adjusted in the range of 1 to 500 _, or 5 to 100 m or 5 to 50 _.
  • the invention and specific embodiments 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.
  • Phenolic resin as a curing agent for epoxy resins (Large-6021, 1) 1 : Co., Ltd., bisphenol-show novolak resin, hydroxyl equivalent 121. Softening point: 133 ° 0 40 ⁇ ; High viscosity liquid epox resin (-3103, Japanese gunpowder Product , Bisphenol Shoepoxy resin, Epoxy equivalent 180 g. 40 Thermoplastic acrylate resin ⁇ -3015 (3 ⁇ 41 ⁇ 2: 900,000 , Glass transition temperature:
  • the adhesive layer of the adhesive film was positioned on the bump surface of the wafer, and vacuum lamination was carried out at 50 ° (:), and each chip was individualized.
  • the individualized bump chips were thermocompressed bonded to a 6ä X 8ä base chip with a 50 II pitch connection pad using a thermocompression bonder.
  • the conditions at that time were temporarily inducted at 10 for 2 seconds at a head temperature of 100 ° (:) and allowed to stand for 10 minutes at 1001 :, and then the head temperature was raised to 26010 for 10 seconds to perform thermocompression bonding at 10 for 4 seconds.
  • the adhesive composition for a semiconductor circuit connection and the adhesive film applied thereto were prepared in the same manner as in Example 1, and a semiconductor device was manufactured using the same.
  • Phenolic resin 0) 1 (:, hydroxyl equivalent: 121 for softening point 133 ° 0) * 1 -31: epoxy resin (Japanese gunpowder, epoxy equivalent for 180 ° C)
  • KBM-403 Coupling Agent (Epoxy, 3-glycidoxypropyl tr imethoxys ilne, Shin-Etsu Chemi cal Co., Ltd.)
  • the adhesive layers obtained in Examples and Comparative Examples, respectively, were laminated by overlapping until the thickness was 320 / mi, and then laminated using a roll laminator at 60 ° C. Then, after each specimen was molded into a circular shape of 8 mm in diameter, a temperature rise rate of 10 ° C / min was applied at a shear rate of 5 rad / s using TA's advanced rheometr ic expansion system (ARES). The viscosity value of the lowest value was judged as melt viscosity.
  • RATS advanced rheometr ic expansion system
  • the differential thermal analyzer was used to measure the temperature at 10 ° C / min in the range of 30 to 300 ° C. The temperature at which the initial reaction peak began to be formed and the basel ine were extrapolated to meet onset It was.
  • the area of the voids between the bump chip and the base chip is 1% or less through Scanning Acous it ic Tomography (SAT). Was evaluated as fail (X).
  • the daisy chain connection could be confirmed as pass (0) and the daisy chain connection could not be confirmed as pass (X).
  • connection section for the semiconductor devices obtained in Examples and Comparative Examples, respectively Polished and exposed and observed under an optical microscope.
  • the adhesive composition trapping was not seen in the connection portion, and the solder was sufficiently wet with the wiring, and the pass ((1)) and the others were evaluated as fail (X).
  • the adhesive films obtained in Examples and Comparative Examples were left at 25 ° C., and then differentially analyzed using differential thermal analysis gears). The change amount was calculated, and the change amount of the lowest melt viscosity was calculated through the lowest melt viscosity measuring method. In the case of s1 ⁇ , it was determined that there was a change over time when the change rate was 20% or more and the minimum melt viscosity was changed by 50% or more. If there was no change over time after 4 weeks (pass), and if there was a change over time within 4 weeks, it was evaluated as fail (X).
  • the adhesive film for semiconductors provided in Examples 1 to 3 had a relatively low melt viscosity and high DSC onset temperature. This seems to be due to the composition of Examples 1 to 3 having a high DSC onset temperature, which results in substantially no microreaction in the temperature range of the drying process upon coating and thus can have a relatively low viscosity. Accordingly, in the semiconductor device to which the adhesive films of Examples 1 to 3 are applied, the voids do not remain substantially, and the change in AH peak is low during the time left for 10 minutes after the temporary welding at KXTC, and thus no change occurs over time. It was also confirmed that no connection failure occurred.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

La présente invention concerne une composition de résine pour l'adhérence de semi-conducteurs, comprenant une résine thermoplastique, une résine thermodurcissable, un agent de durcissement et un composé ayant une structure spécifique ; et un film adhésif semi-conducteur fabriqué à l'aide de celle-ci.
PCT/KR2019/004651 2018-04-17 2019-04-17 Composition adhésive pour connexion de circuit à semi-conducteurs et film adhésif contenant celle-ci WO2019203572A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN201980006175.4A CN111448276B (zh) 2018-04-17 2019-04-17 用于半导体电路连接的粘合剂组合物和包含其的粘合剂膜
EP19789001.5A EP3693434A4 (fr) 2018-04-17 2019-04-17 Composition adhésive pour connexion de circuit à semi-conducteurs et film adhésif contenant celle-ci
JP2020526595A JP6983461B2 (ja) 2018-04-17 2019-04-17 半導体回路接続用接着剤組成物およびこれを含む接着フィルム
US16/769,786 US11834415B2 (en) 2018-04-17 2019-04-17 Adhesive composition for semiconductor circuit connection and adhesive film including the same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2018-0044654 2018-04-17
KR20180044654 2018-04-17
KR1020190043931A KR102204964B1 (ko) 2018-04-17 2019-04-15 반도체 회로 접속용 접착제 조성물 및 이를 포함한 접착 필름
KR10-2019-0043931 2019-04-15

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WO2019203572A1 true WO2019203572A1 (fr) 2019-10-24

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